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Sample records for cyathane diterpenoid natural

  1. Laxitextines A and B, Cyathane Xylosides from the Tropical Fungus Laxitextum incrustatum.

    PubMed

    Mudalungu, Cynthia M; Richter, Christian; Wittstein, Kathrin; Abdalla, Muna Ali; Matasyoh, Josphat C; Stadler, Marc; Süssmuth, Roderich D

    2016-04-22

    Bioassay-guided fractionation of the mycelial extract of a basidiomycete culture collected in Kenya led to the isolation of two new cyathane diterpenoids named laxitextines A (1) and B (2). The producer strain was characterized by detailed taxonomic studies based on rDNA using the 5.8S gene region, the internal transcribed spacer 2 (ITS2), and part of the large subunit that identified the fungus as Laxitextum incrustatum. The structures of 1 and 2 were elucidated by NMR spectroscopic and mass spectrometric analyses. Both compounds exhibited moderate activities against Gram-positive bacteria Bacillus subtilis (DSM 10), Staphylococcus aureus (DSM 346), and methicillin-resistant Staph. aureus (DSM 1182). The two compounds also showed variable antiproliferative activities against mouse fibroblast (L929) and selected human cell lines (breast cancer MCF-7, epidermoid carcinoma A431, and umbilical vein endothelial HUVEC). The IC50 values with respect to the MCF-7 cell line for compounds 1 and 2 were 2.3 and 2.0 μM, respectively. PMID:27043217

  2. Ingenane Diterpenoids.

    PubMed

    Appendino, Giovanni

    2016-01-01

    Despite a more recent isolation and chemical characterization when compared to phorbol, along with its chemical instability, limited distribution in Nature, and scarce availability, ingenol is the only Euphorbia diterpenoid that has undergone successful pharmaceutical development, with ingenol 3-angelate (ingenol mebutate, Picato(®)) entering the pharmaceutical market in 2012 for the treatment of actinic keratosis. The phytochemical, chemical, and biological literature on members of the ingenane class of diterpenoids is reviewed from their first isolation in 1968 through 2015, highlighting unresolved issues both common to phorboids (biogenesis, relationship between molecular targets, and in vivo activity) and specific to ingenol derivatives (two-dimensional representation, in-out stereoisomerism, versatility of binding mode to PKC, and inconsistencies in the structural elucidation of some classes of derivatives). The biogenesis of ingenol is discussed in the light of the Jakupovic proposal of a dissection between the formation of the macrocyclic Euphorbia diterpenoids and the phorboids, and the clinical development of ingenol mebutate is chronicled in the light of its "reverse-pharmacology" focus. PMID:27380406

  3. A natural diterpenoid kamebacetal A with anti-tumor activity: Theoretical and experimental study

    NASA Astrophysics Data System (ADS)

    Wang, Tao; Tang, Fu-ming; Zhang, Yi-Heng; Chen, Zhong

    2010-06-01

    Kamebacetal A ( 1) is an ent-kaurane diterpenoid isolated from Isodon racemosa (Hemsl) Hara. This natural product exhibits significant cytotoxicity against human Bel-7402 and HO-8910 tumor cells. The geometrical conformation of 1 has been optimized at the B3LYP/6-311+G(d) level of theory. The results indicated that the calculated geometric parameters are close to the X-ray crystal structure. The theoretical 13C NMR chemical shifts of 1 were also calculated at the GIAO-B3LYP level of theory with different basis sets. The calculated NMR chemical shifts are in closer agreement with the experimental results. A molecular electrostatic potential (MEP) map was used in an attempt to identify key features of the kamebacetal A to account for its anti-tumor activity. MEP investigations reveal that compound 1, which shows anti-tumor activity, possesses electron-rich regions that extend over the hydroxyl and carbonyl groups of compound 1. The data generated in this study is valuable as it provides an insight into kamebacetal A molecular and structure-activity relationships.

  4. Anti-tumour activity of longikaurin A (LK-A), a novel natural diterpenoid, in nasopharyngeal carcinoma

    PubMed Central

    2013-01-01

    Background Longikaurin A is a natural ent-kaurene diterpenoid isolated from Isodon genus. The ent-kaurene diterpenoids isolated from medicinal plants have been shown to have anti-disease effects. The present study was designed to examine the anti-tumour effects of longikaurin A (LK-A) in nasopharyngeal carcinoma in vitro and in vivo. Methods Apoptosis and cell cycle arrest were determined by flow cytometry analysis of the cells treated with Longikaurin A. The proteins of apoptosis signaling pathway were detected by western blotting analysis. Finally, we examined whether LK-A exhibits anti-tumour activity in xenograft models. Results Longikaurin A inhibited the cell growth by inducing apoptosis and cell cycle arrest. At low concentrations, longikaurin A induced S phase arrest and at higher concentrations, longikaurin A induced caspase-dependent apoptosis by regulating apoptotic molecules. Finally, longikaurin A significantly inhibited the tumour growth of CNE2 xenografts in vivo and showed no obvious effect on the body weights of the mice. Conclusion Our results suggest that Longikaurin A exhibited anti-tumour activity in nasopharyngeal carcinoma in vitro and in vivo. PMID:23985029

  5. Diterpenoids from Fagonia mollis.

    PubMed

    Sallam, Amal; Nugroho, Alfarius Eko; Hirasawa, Yusuke; Chin-Piow, Wong; Kaneda, Toshio; Shirota, Osamu; Gedara, Sahar R; Morita, Hiroshi

    2014-09-01

    A new acyclic diterpenoid (1) and a new erythroxan diterpenoid (2), together with 4 erythroxan diterpenoids and 3 triterpenoids, have been isolated from the aerial parts of Fagonia mollis. Their structures were elucidated on the basis of 1D and 2D NMR data. The cytotoxic activity of the isolated compounds was investigated against HL-60 cancer cells. PMID:25918782

  6. New clerodane diterpenoids from Croton crassifolius.

    PubMed

    Qiu, Maosong; Cao, Di; Gao, Youheng; Li, Shuhua; Zhu, Jinping; Yang, Bao; Zhou, Lian; Zhou, Yuan; Jin, Jing; Zhao, Zhongxiang

    2016-01-01

    Two new clerodane diterpenoids (1-2), one new clerodane diterpenoid alkaloid (3), as well as thirteen known compounds were isolated from Croton crassifolius. The structures of new compounds were established by a combination of spectroscopic methods, including HRMS, (1)H NMR, (13)C NMR, (1)H (1)H COSY, HSQC, HMBC, NOESY and X-ray crystallographic analysis. Compound 3 is firstly reported as the clerodane-type diterpenoid alkaloid in natural products. All of the compounds were evaluated for in vitro cytotoxic activities against CT26.WT cell using the MTT method.

  7. Diterpenoids from Leaves of Rubus chingii.

    PubMed

    Shu, Jicheng; Huang, Yingzheng; Cui, Hangqing; Peng, Caiying; Liu, Jianqun; Huang, Huilian

    2016-03-01

    The leaves of Rubus chingii were examined for their phytochemical composition and anti-yeast activity. In the process, seven diterpenoids (compounds 1-7), including a new natural compound (14β, 16-epoxy-7-pimarene-3α, 15β-diol, 1), were isolated and elucidated. Compound 1 exhibited moderate anti-Candida activity.

  8. Diterpenoids from Leaves of Rubus chingii.

    PubMed

    Shu, Jicheng; Huang, Yingzheng; Cui, Hangqing; Peng, Caiying; Liu, Jianqun; Huang, Huilian

    2016-03-01

    The leaves of Rubus chingii were examined for their phytochemical composition and anti-yeast activity. In the process, seven diterpenoids (compounds 1-7), including a new natural compound (14β, 16-epoxy-7-pimarene-3α, 15β-diol, 1), were isolated and elucidated. Compound 1 exhibited moderate anti-Candida activity. PMID:27169185

  9. NMR spectroscopicsearch module for Spektraris, an online resource for plant natural product identification – taxane diterpenoids from Taxus × media cell suspension cultures as a case study

    PubMed Central

    Fischedick, Justin T.; Johnson, Sean R.; Ketchum, Raymond E.B.; Croteau, Rodney B.; Lange, B. Markus

    2014-01-01

    Development and testing of Spektraris-NMR an online spectral resource, is reported for the NMR-based structural identification of plant natural products (PNPs). Spektraris-NMRallows users to search with multiple spectra at once and returns a table with alist of hits arranged according to the goodness of fit between query data and database entries. For each hit, a link to a tabulated alignment of 1H-NMR and 13C-NMR spectroscopic peaks (query versus database entry) is provided. Furthermore, full spectroscopic records and experimental meta information about each database entry can be accessed online. To test the utility of Spektraris-NMR for PNP identification, the database was populated with NMR data (total of 466 spectra) for ∼250 taxanes, which are structurally complex diterpenoids (including the anticancer drug taxol) commonly found in the genus Taxus. NMR data generated used was then generated with metabolites purified from Taxus cell suspension cultures to search Spektraris-NMR, and were able to identify eight taxanes with high confidence. A ninth isolated metabolite could be assigned, based on spectral searches, to a taxane skeletal class, but no high confidence hit was produced. Using various spectroscopic methods, this metabolite was characterized as the taxane 2-deacetylbaccatin IV, a novel taxane. These results indicate that Spektraris-NMR is a valuable resource for rapid and reliable identification of known metabolites and has the potential to contribute to de-replication efforts in the search for novel PNPs. PMID:25534952

  10. Evaluation of Aconitum diterpenoid alkaloids as antiproliferative agents.

    PubMed

    Wada, Koji; Ohkoshi, Emika; Zhao, Yu; Goto, Masuo; Morris-Natschke, Susan L; Lee, Kuo-Hsiung

    2015-04-01

    Little information has been reported on the antitumor effects of the diterpenoid alkaloid constituents of Aconitum plants, used in the herbal drug 'bushi'. This study was aimed at determining the antitumor activities of Aconitum C19-and C20-diterpenoid alkaloids and synthetic derivatives against lung (A549), prostate (DU145), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) cancer cell lines. Newly synthesized C20-diterpenoid alkaloid derivatives showed substantial suppressive effects against all human tumor cell lines tested. In contrast, natural and derivatized C19-diterpenoid alkaloids showed only a slight or no effect. Most of the active compounds were hetisine-type C20-diterpenoid alkaloids, specifically kobusine and pseudokobusine analogs with two different substitution patterns, C-11 and C-11,15. Notably, several C20-diterpenoid alkaloids were more potent against multidrug-resistant KB subline KB-VIN cells. Pseudokobusine 11-3'-trifluoromethylbenzoate (94) is a possible promising new lead meriting additional evaluation against multidrug-resistant tumors.

  11. The isolation and synthesis of neodolastane diterpenoids.

    PubMed

    Marković, Dean; Kolympadi, Maria; Deguin, Brigitte; Porée, François-Hugues; Turks, Māris

    2015-02-01

    The neodolastane diterpenoids comprise a group of 44 compounds including guanacastepenes, heptemerones, plicatilisins, radianspenes, 2,15-epoxy-5,13-dihydroxyneodolast-3-en-14-one and sphaerostanol. These fungal and marine natural products are characterized by a tricyclic neodolastane skeleton that consists of fused five-, seven- and six-membered rings. Their reported antibiotic activities against antibiotic-resistant bacteria together with strong antifungal and anticancer activities and their novel structures render these compounds interesting synthetic targets. The aim of this account is to summarise the progress in the isolation, characterisation and synthesis of these diterpenoids as well as to review their biogenetic origins and diverse biological activities since their discovery in 2000.

  12. Diterpenoids from Isodon sculponeatus.

    PubMed

    Jiang, Hua-Yi; Wang, Wei-Guang; Zhou, Min; Wu, Hai-Yan; Zhan, Rui; Li, Xiao-Nian; Du, Xue; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong

    2014-03-01

    Phytochemical investigation of the aerial parts of Isodon sculponeatus afforded six new 7,20-epoxy-ent-kauranoids, sculponins U-Z (1-6), and 11 known diterpenoids (7-17). The structures of these new compounds were elucidated primarily by means of extensive spectroscopic analysis, and the absolute configuration of 1 was determined by single crystal X-ray diffraction. Compound 5 exhibited weak cytotoxic activity against HL-60, SMMC-7721, MCF-7, and SW-480 cell lines, and it also inhibited NO production in LPS-stimulated RAW264.7 cells, with IC50 value of 13.8 μM. PMID:24418655

  13. Diterpenoid tetracyclic hydrocarbons of petroleum

    SciTech Connect

    Vorob'eva, N.S.; Zemskova, Z.K.; Pekh, T.I.; Petrov, A.A.

    1987-08-01

    Diterpenoid hydrocarbons are fairly widespread in various caustobioliths. However, if petroleums contain mainly acyclic diterpenoids (phytane, pristane and norpristane), cyclic diterpaenes such as fichtelite, pimarane, iosene (kaurane) and hibbane are often found in hydrocarbons isolated from coal and shale. Recent advances in the chemistry of diterpenoids isolated from caustobioliths, are described in a separate paper. Much less is known about petroleum polycyclic diterpenoid hydrocarbons, particularly those with four saturated rings. A series of tetracyclic hydrocarbons C/sub 19/H/sub 32/ (molar mass 260), found in a number of light petroleums and gas condensates from the Jura deposits of Central Kara-Kum (Turkmen S.S.R.), are examined here. These hydrocarbons are present in petroleums and condensates from the Davaly, Erden, Ortakak, Southern Beuideshik deposits, they are always identical and occur in the same ratios. The composition of the tretracyclanes isolated from the Ortakak gas condensates (well 17) will be examined in detail.

  14. Clerodane diterpenoids from Pulicaria wightiana.

    PubMed

    Das, Biswanath; Ravinder Reddy, M; Ramu, R; Ravindranath, N; Harish, H; Ramakrishna, K V S; Koteswar Rao, Y; Harakishore, K; Murthy, U S N

    2005-03-01

    Five clerodane diterpenoids have been isolated from the aerial parts of Pulicaria wightiana along with 3'5,6-trihydroxy-3,4',7-trimethoxyflavone and 2-methyl-5-hydroxy-chroman-4-one. The structures and stereochemistry of the compounds were established from spectral (mainly 1D and 2D NMR) studies. The last two compounds were not reported earlier from this plant. The antibacterial activity of the diterpenoids were studied.

  15. New bis-spirolabdane-type diterpenoids from Leonurus heterophyllus Sw.

    PubMed

    Giang, Phan Minh; Son, Phan Tong; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2005-11-01

    Twelve natural bis-spirolabdane-type diterpenoids, including eight new, named leoheteronones A-E, 15-epileoheteronones B, D, and E, and four known leopersin B, 15-epileopersin B, leopersin C, and 15-epileopersin C, together with hispanone and galeopsin were isolated from the aerial parts of the medicinal plant Leonurus heterophyllus SW. (Lamiaceae) grown in Vietnam. Their structures were determined by spectroscopic analyses. The current study emphasized the accumulation of C-15 oxygenated bis-spirolabdane-type diterpenoids of both 13R and 13S configurations in L. heterophyllus.

  16. New labdane-type diterpenoids from Leonurus heterophyllus SW.

    PubMed

    Giang, Phan Minh; Son, Phan Tong; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2005-08-01

    Five new natural labdane-type diterpenoids (5-9), designated leoheteronins A-E, together with four known diterpenoids (1-4), two phytosterols as a mixture of beta-sitosterol and stigmasterol, and the flavone genkwanin (10) were isolated from the aerial parts of Leonurus heterophyllus SW. (Lamiaceae) collected in northern Vietnam. Compound 1 was isolated for the first time from a Leonurus species, and 10 is considered to be a chemotaxonomic marker of the Leonurus genus. Their structures were determined using spectroscopic analyses.

  17. Ozonolytic transformations of labdane diterpenoids

    NASA Astrophysics Data System (ADS)

    Vlad, Pavel F.; Aryku, A. N.

    1992-07-01

    Information on the products of ozonolysis of labdane and ent-labdane diterpenoids is correlated. The effects of the ozonolysis conditions, the procedure for treating the products and the location of double bonds and other functional groups on the character of the resulting ozonolysis products are considered. The bibliography includes 91 references.

  18. Crotofolane diterpenoids from Croton caracasanus.

    PubMed

    Chávez, Katiuska; Compagnoneb, Reinaldo S; Riina, Ricarda; Briceño, Alexander; González, Teresa; Squitieri, Emilio; Landaetab, Carlos; Soscrún, Humberto; Suáreza, Alírica I

    2013-12-01

    Four new crotofolane-type diterpenoids, crotocarasin (A-D) (1-4), together with the known crotofolin E, were isolated from a dichloromethane extract of the stems of Croton caracasanus Pittier. The structures of the new compounds were determined by spectroscopic methods, and the structure of 3 was further confirmed by single-crystal X-ray data analyses.

  19. Spongian diterpenoids inhibit androgen receptor activity

    PubMed Central

    Yang, Yu Chi; Meimetis, Labros G; Tien, Amy H; Mawji, Nasrin R; Carr, Gavin; Wang, Jun; Andersen, Raymond J; Sadar, Marianne D

    2013-01-01

    Androgen receptor (AR) is a ligand-activated transcription factor and a validated drug target for all stages of prostate cancer. Antiandrogens compete with physiological ligands for AR ligand-binding domain (LBD). High-throughput screening of a marine natural product library for small molecules that inhibit AR transcriptional activity yielded the furanoditerpenoid spongia-13(16),-14-dien-19-oic acid, designated terpene 1 (T1). Characterization of T1 and the structurally related semi-synthetic analogues (T2 and T3) revealed that these diterpenoids have antiandrogen properties that include inhibition of both androgen-dependent proliferation and AR transcriptional activity by a mechanism that involved competing with androgen for AR LBD and blocking essential N/C interactions required for androgen-induced AR transcriptional activity. Structure activity relationship analyses revealed some chemical features of T1 that are associated with activity and yielded T3 as the most potent analogue. In vivo, T3 significantly reduced the weight of seminal vesicles, which are an androgen-dependent tissue, thereby confirming T3’s on-target activity. The ability to create analogues of diterpenoids that have varying antiandrogen activity represents a novel class of chemical compounds for the analysis of AR ligand-binding properties and therapeutic development. PMID:23443807

  20. Marine Diterpenoids as Potential Anti-Inflammatory Agents.

    PubMed

    González, Yisett; Torres-Mendoza, Daniel; Jones, Gillian E; Fernandez, Patricia L

    2015-01-01

    The inflammatory response is a highly regulated process, and its dysregulation can lead to the establishment of chronic inflammation and, in some cases, to death. Inflammation is the cause of several diseases, including rheumatoid arthritis, inflammatory bowel diseases, multiple sclerosis, and asthma. The search for agents inhibiting inflammation is a great challenge as the inflammatory response plays an important role in the defense of the host to infections. Marine invertebrates are exceptional sources of new natural products, and among those diterpenoids secondary metabolites exhibit notable anti-inflammatory properties. Novel anti-inflammatory diterpenoids, exclusively produced by marine organisms, have been identified and synthetic molecules based on those structures have been obtained. The anti-inflammatory activity of marine diterpenoids has been attributed to the inhibition of Nuclear Factor-κB activation and to the modulation of arachidonic acid metabolism. However, more research is necessary to describe the mechanisms of action of these secondary metabolites. This review is a compilation of marine diterpenoids, mainly isolated from corals, which have been described as potential anti-inflammatory molecules. PMID:26538822

  1. Marine Diterpenoids as Potential Anti-Inflammatory Agents

    PubMed Central

    González, Yisett; Torres-Mendoza, Daniel; Jones, Gillian E.; Fernandez, Patricia L.

    2015-01-01

    The inflammatory response is a highly regulated process, and its dysregulation can lead to the establishment of chronic inflammation and, in some cases, to death. Inflammation is the cause of several diseases, including rheumatoid arthritis, inflammatory bowel diseases, multiple sclerosis, and asthma. The search for agents inhibiting inflammation is a great challenge as the inflammatory response plays an important role in the defense of the host to infections. Marine invertebrates are exceptional sources of new natural products, and among those diterpenoids secondary metabolites exhibit notable anti-inflammatory properties. Novel anti-inflammatory diterpenoids, exclusively produced by marine organisms, have been identified and synthetic molecules based on those structures have been obtained. The anti-inflammatory activity of marine diterpenoids has been attributed to the inhibition of Nuclear Factor-κB activation and to the modulation of arachidonic acid metabolism. However, more research is necessary to describe the mechanisms of action of these secondary metabolites. This review is a compilation of marine diterpenoids, mainly isolated from corals, which have been described as potential anti-inflammatory molecules. PMID:26538822

  2. Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

    PubMed Central

    2015-01-01

    Summary This review describes strategies for the chemical synthesis of xenicane diterpenoids and structurally related metabolites. Selected members from the four different subclasses of the Xenia diterpenoid family, the xenicins, xeniolides, xeniaphyllanes and xeniaethers, are presented. The synthetic strategies are discussed with an emphasis on the individual key reactions for the construction of the uncommon nine-membered carbocycle which is the characteristic structural feature of these natural products. Additionally, the putative biosynthetic pathway of xenicanes is illustrated. PMID:26734099

  3. Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives.

    PubMed

    Timoshenko, Mariya A; Kharitonov, Yurii V; Shakirov, Makhmut M; Bagryanskaya, Irina Yu; Shults, Elvira E

    2016-02-01

    A selective synthesis of 7- or 14-nitrogen containing tricyclic diterpenoids was completed according to a strategy in which the key step was the catalyzed direct allylic amination of methyl 14α-hydroxy-15,16-dihydroisopimarate with a wide variety of nitrogenated nucleophiles. It was revealed that the selectivity of the reaction depends on the nature of nucleophile. The catalyzed reaction of the mentioned diterpenoid allylic alcohol with 3-nitroaniline, 3-(trifluoromethyl)aniline, and 4-(trifluoromethyl)aniline yield the subsequent 7α-, 7β- and 14αnitrogen-containing diterpenoids. The reaction with 2-nitroaniline, 4-nitro-2-chloroaniline, 4-methoxy-2-nitroaniline, phenylsulfamide, or tert-butyl carbamate proceeds with the formation of 7α-nitrogen-substituted diterpenoids as the main products. PMID:27308214

  4. Labdane Diterpenoids from Leonotis leonurus

    PubMed Central

    Wu, Hankui; Li, Jun; Fronczek, Frank R.; Ferreira, Daneel; Burandt, Charles L.; Setola, Vincent; Roth, Bryan L.; Zjawiony, Jordan K.

    2012-01-01

    Three known (leoleorins A-C) and eight new (leoleorins D-J and 16-epi-leoleorin F) labdane diterpenoids, were isolated from leaves of Leonotis leonurus. The absolute configurations of leoleorins A and D were established by X-ray crystallographic analyses. In competitive binding assay all isolated compounds showed inhibition in excess of 50% at various CNS receptors. Leoleorin C showed moderate binding affinity (Ki = 2.9 μM) for the Sigma 1 receptor. PMID:22445074

  5. Labdane diterpenoids from Leonurus sibiricus.

    PubMed

    Wu, Hankui; Fronczek, Frank R; Ferreira, Daneel; Burandt, Charles L; Zjawiony, Jordan K

    2011-04-25

    Six new labdane diterpenoids, preleosibirone A (1), 13-epi-preleosibirone A (2), isopreleosibirone A (3), leosibirone A (4), leosibirone B (5), and 15-epi-leosibirone B (6), were isolated from the leaves of Leonurus sibiricus. The absolute configurations of 1, 2, 5, and 6 were established by X-ray crystallographic analyses, and leosibirone A (4) was shown to be an artifact of the isolation process.

  6. Labdane Diterpenoids from Leonurus sibiricus

    PubMed Central

    Wu, Hankui; Fronczek, Frank R.; Ferreira, Daneel; Burandt, Charles L.; Zjawiony, Jordan K.

    2011-01-01

    Six new labdane diterpenoids, preleosibirone A (1), 13-epi-preleosibirone A (2), isopreleosibirone A (3), leosibirone A (4), leosibirone B (5), and 15-epi-leosibirone B (6), were isolated from the leaves of Leonurus sibiricus. The absolute configurations of 1, 2, 5, and 6 were established by X-ray crystallographic analyses, and leosibirone A (4) was shown to be an artifact of the isolation process. PMID:21375312

  7. Labdane diterpenoids from Leonotis leonurus.

    PubMed

    Wu, Hankui; Li, Jun; Fronczek, Frank R; Ferreira, Daneel; Burandt, Charles L; Setola, Vincent; Roth, Bryan L; Zjawiony, Jordan K

    2013-07-01

    Three known (leoleorins A-C) and eight hitherto unknown (leoleorins D-J and 16-epi-leoleorin F) labdane diterpenoids, were isolated from leaves of Leonotis leonurus. The absolute configurations of leoleorins A and D were established by X-ray crystallographic analyses. In a competitive binding assay, all isolated compounds showed inhibition in excess of 50% at various CNS receptors. Leoleorin C showed moderate binding affinity (Ki=2.9 μM) for the Sigma 1 receptor.

  8. A Novel Norclerodane Diterpenoid from the Roots of Croton crassifolius.

    PubMed

    Zhang, Zhan-Xin; Li, Hui-Hong; Fan, Gai-Xia; Li, Zheng-Yu; Dong, Le-Le; Li, Hong-Yu; Fei, Dong-Qing

    2015-11-01

    A chemical investigation of Croton crassifolius afforded a novel norclerodane diterpenoid (1) with an unprecedented six-membered oxygen ring between C-1 and C-12, together with three known compounds. The structure of the new compound was elucidated based on spectroscopic (IR, 1D, and 2D NMR) and HR-ESI-MS techniques. This report describes the first example of a natural norclerodane with a 4H-chromene ring system.

  9. Asymmetric synthesis and absolute stereochemistry of a labdane-type diterpenoid isolated from the rhizomes of Isodan yuennanensis.

    PubMed

    Deng, Heping; Cao, Wei; Zhang, Zhijiang; Liu, Bo

    2016-07-14

    The first synthesis of a labdane-type diterpenoid isolated from Isodon yuennanensis was achieved in fourteen steps from commercially available starting material, (+)-sclareolide. The synthesis features the Barton nitrite ester reaction to introduce an oxime at the angular methyl group and the Jones oxidation to construct the lactone segment. By comparison of the optical rotation of our synthetic sample and the natural sample, the absolute stereochemistry of the natural diterpenoid has been determined. PMID:27251032

  10. Identification of a new cyathane diterpene that induces mitochondrial and autophagy-dependent apoptosis and shows a potent in vivo anti-colorectal cancer activity.

    PubMed

    He, Luwei; Han, Junjie; Li, Baowei; Huang, Li; Ma, Ke; Chen, Quan; Liu, Xinzhong; Bao, Li; Liu, Hongwei

    2016-03-23

    Diterpenes has been reported to possess multiple bioactivities consisting of anti-microbial and anti-inflammatory properties. This study reveals a new cyathane-type diterpene (cyathin Q) from the culture of the fungus Cyathus africanus by bioactivity-guided separation. The structure of cyathin Q was determined based on spectroscopic measurements (NMR and MS). The bioactivity evaluation shows that cyathin Q has a strong anticancer activity against HCT116 cells and Bax-deficient HCT116 in vitro and in vivo. This compound induced hallmarks of apoptotic events in HCT116 cells, including caspase activation, cytochrome c release, poly (ADP-ribose) polymerase (PARP) cleavage, and depolarization of the mitochondrial inner transmembrane potential. This process is accompanied with the increased mitochondrial ROS, down-regulation of Bcl-2 protein, and up-regulation of Bim protein. We also observed the cleavage of autophagy-related protein ATG5 in cyathin Q-induced apoptosis. Taken together, our study identified a new fungal diterpene that exhibited anticancer activity via induction of mitochondria and autophagy-dependent apoptosis in HCT116 cells.

  11. Diterpenoid derivatives of Kenyan Croton sylvaticus.

    PubMed

    Ndunda, Beth; Langat, Moses K; Midiwo, Jacob O; Omosa, Leonidah K

    2015-04-01

    Kenyan Croton sylvaticus Hochst. ex Krauss gave four clerodane diterpenoids, the new ent-3,13E-clerodadiene-15-formate (1), the known 15-acetoxy-ent-3,13E-clerodadiene (2), ent-3,13E-clerodadien-15-ol (3) and hardwickiic acid (4), two known halimane diterpenoids, penduliflaworosin (5) and crotohalimaneic acid (6) and one labdane diterpenoid, labda-13E-ene-8a,15-diol (7). The compounds, when tested for their anti-microbial activities against Bacillus subtilis, Xanthomonas campestris and Candida albicans, were found to be inactive.

  12. Syntheses of Denudatine Diterpenoid Alkaloids: Cochlearenine, N-Ethyl-1α-hydroxy-17-veratroyldictyzine, and Paniculamine.

    PubMed

    Kou, Kevin G M; Li, Beryl X; Lee, Jack C; Gallego, Gary M; Lebold, Terry P; DiPasquale, Antonio G; Sarpong, Richmond

    2016-08-31

    The denudatine-type diterpenoid alkaloids cochlearenine, N-ethyl-1α-hydroxy-17-veratroyldictyzine, and paniculamine have been synthesized for the first time (25, 26, and 26 steps from 16, respectively). These syntheses take advantage of a common intermediate (8) that we have previously employed in preparing aconitine-type natural products. The syntheses reported herein complete the realization of a unified strategy for the preparation of C20, C19, and C18 diterpenoid alkaloids. PMID:27525345

  13. Total Synthesis and Biological Evaluation of an Antifungal Tricyclic o-Hydroxy-p-Quinone Methide Diterpenoid

    PubMed Central

    Huang, Jinhua; Foyle, Dylan; Lin, Xiaorong

    2013-01-01

    A convergent route has been developed to synthesize an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid and analogs. The Li/naphthalene mediated reductive alkylation was employed for coupling β-cyclocitral and the corresponding benzyl chloride while the BBr3–mediated one-pot bis-demethylation and intramolecular Friedel Crafts alkylation was used to assemble the tricyclic molecular skeleton. The structure-activity relationship of the diterpenoid was assessed based on anti-proliferation assays of the natural product and analogs against strains of pathogenic yeasts and filamentous fungi. PMID:23957833

  14. New norclerodane diterpenoids from the tubers of Dioscorea bulbifera.

    PubMed

    Tang, Ying; Xue, Yong-bo; Zhou, Lei; Zhang, Jin-wen; Yao, Guang-min; Luo, Zeng-wei; Du, Guang; Zhang, Yong-hui

    2014-01-01

    Phytochemical investigations of the tubers of Dioscorea bulbifera L. resulted in the isolation of nine norclerodane diterpenoids, including two new compounds, diosbulbins N (1) and P (3), a new naturally occurring compound, diosbulbin O (2), and six known ones, diosbulbins A-D, F and G (4-9). Their structures were established by spectroscopic and chemical methods. The absolute stereochemistry of 1 was determined by a modified Mosher's method, and the absolute configuration of 2 was determined by a single-crystal X-ray diffraction analysis with CuKα irradiation. Compounds 1-3 were evaluated for in vitro cytotoxicity against five human cancer cell lines.

  15. The nature and fate of natural resins in the geosphere. XII. Investigation of C-ring aromatic diterpenoids in Raritan amber by pyrolysis-GC-matrix isolation FTIR-MS

    PubMed Central

    Anderson, Ken B

    2006-01-01

    Upper Cretaceous amber from the Raritan Formation (Sayerville, New Jersey) has been investigated by Pyrolysis-GC-MS and Pyrolysis-GC-matrix isolation FTIR-MS. Results establish the existence of two distinct forms of amber in this deposit. Both forms are Class Ib ambers, but they are unambiguously differentiated on the basis of their (intact) diterpenoid composition. The presence of callitrisate in both forms, and cupraene in samples designated form 1, strongly suggest that both derive from related-but-distinct species within the Cupressaceae. In addition to callitrisate, dehydroabietate and analogous 17-nor-, 16,17-dinor- and 15,16,17-trinor- analogues of these compounds are also observed. The distributions of these products in multiple samples suggest that they are the result of biological emplacement, rather than diagenetic modification of the parent compounds. This indicates that the distributions of diterpenes observed in these samples are representative of the original bioterpenoids and, hence, are useful for chemotaxonomic analyses. PMID:16759406

  16. Cytotoxic diterpenoids from Rabdosia lophanthoides var. gerardianus.

    PubMed

    Lin, Chao-Zhan; Zhao, Wei; Feng, Xiu-Li; Liu, Fang-Le; Zhu, Chen-Chen

    2016-03-01

    Two new abietane diterpenoids, Gerardianin B (1) and Gerardianin C (2), one new lignan glycoside, Gerardianin D (3) and one new lupane-type triterpenoid, Gerardianol A (4), together with seven known abietane diterpenoids were isolated from the aerial parts of Rabdosia lophanthoides var. gerardianus. Their structures were determined by 1D and 2D NMR spectroscopic data. The cytotoxic activities of the nine diterpenoids were evaluated on human cancer cell lines. Compounds 6-11 exhibited significant cytotoxic activities against HepG2 cell lines with IC50 from 4.68 to 9.43μM and HCF-8 cell lines with IC50 from 9.12 to 13.53μM. PMID:26608401

  17. Diterpenoid Biopolymers: New Directions for Renewable Materials Engineering

    PubMed Central

    Hillwig, Matthew L.; Mann, Francis M.; Peters, Reuben J.

    2010-01-01

    Most types of ambers are naturally occurring, relatively hard, durable resinite polymers derived from the exudates of trees. This resource has been coveted for thousands of years due to its numerous useful properties in industrial processes, beauty, and purported medicinal properties. Labdane diterpenoid based ambers represent the most abundant and important resinites on earth. These resinites are a dwindling, non-renewable natural resource, so a new source of such materials needs to be established. Recent advances in sequencing technologies and biochemical engineering are rapidly accelerating the rate of identifying and assigning function to genes involved in terpenoid biosynthesis, as well as producing industrial-scale quantities of desired small-molecules in bacteria and yeast. This has provided new tools for engineering metabolic pathways capable of producing diterpenoid monomers that will enable the production of custom-tailored resinite-like polymers. Furthermore, this biosynthetic toolbox is continuously expanding, providing new possibilities for renewing dwindling stocks of naturally occurring resinite materials and engineering new materials for future applications. PMID:20857504

  18. Diterpenoids and triterpenoids from Euphorbia retusa.

    PubMed

    Haba, Hamada; Lavaud, Catherine; Magid, Abdulmagid Alabdul; Benkhaled, Mohammed

    2009-07-01

    Six new ent-abietane lactones (1-6), three new esterified tetracyclic triterpenes (7-9), and seven known diterpenoids and triterpenoids were isolated from the roots of Euphorbia retusa. Their structures were elucidated by means of spectroscopic studies including 1D and 2D NMR, mass spectrometry, chemical transformation, and comparison with literature data.

  19. [A diterpenoid quinone from Periploca forrestii].

    PubMed

    Wang, Yan; Sun, Lei; Qiao, Shanyi

    2010-06-01

    Tanshinone II A, which was known unique to the salvia, was separated and purified by silica gel column chromatography and recrystallisation from an ethyl acetate-soluble portion (the anti-inflammatory active portion) of ethanol extract of Periploca forrestii. The diterpenoid quinone was obtained from the Periploca for the first time. PMID:20815227

  20. Oridonin, a Promising ent-Kaurane Diterpenoid Lead Compound

    PubMed Central

    Li, Dahong; Han, Tong; Liao, Jie; Hu, Xu; Xu, Shengtao; Tian, Kangtao; Gu, Xiaoke; Cheng, Keguang; Li, Zhanlin; Hua, Huiming; Xu, Jinyi

    2016-01-01

    Oridonin belongs to ent-kaurane tetracyclic diterpenoid and was first isolated from Isodon species. It exhibits inhibitory activities against a variety of tumor cells, and pharmacological study shows that oridonin could inhibit cell proliferation, DNA, RNA and protein synthesis of cancer cells, induce apoptosis and exhibit an antimutagenic effect. In addition, the large amount of the commercially-available supply is also very important for the natural lead oridonin. Moreover, the good stability, suitable molecular weight and drug-like property guarantee its further generation of a natural-like compound library. Oridonin has become the hot molecule in recent years, and from the year 2010, more than 200 publications can be found. In this review, we summarize the synthetic medicinal chemistry work of oridonin from the first publication 40 years ago and share our research experience of oridonin for about 10 years, which may provide useful information to those who are interested in this research field. PMID:27563888

  1. Oridonin, a Promising ent-Kaurane Diterpenoid Lead Compound.

    PubMed

    Li, Dahong; Han, Tong; Liao, Jie; Hu, Xu; Xu, Shengtao; Tian, Kangtao; Gu, Xiaoke; Cheng, Keguang; Li, Zhanlin; Hua, Huiming; Xu, Jinyi

    2016-01-01

    Oridonin belongs to ent-kaurane tetracyclic diterpenoid and was first isolated from Isodon species. It exhibits inhibitory activities against a variety of tumor cells, and pharmacological study shows that oridonin could inhibit cell proliferation, DNA, RNA and protein synthesis of cancer cells, induce apoptosis and exhibit an antimutagenic effect. In addition, the large amount of the commercially-available supply is also very important for the natural lead oridonin. Moreover, the good stability, suitable molecular weight and drug-like property guarantee its further generation of a natural-like compound library. Oridonin has become the hot molecule in recent years, and from the year 2010, more than 200 publications can be found. In this review, we summarize the synthetic medicinal chemistry work of oridonin from the first publication 40 years ago and share our research experience of oridonin for about 10 years, which may provide useful information to those who are interested in this research field. PMID:27563888

  2. Euphorbesulins A-P, Structurally Diverse Diterpenoids from Euphorbia esula.

    PubMed

    Zhou, Bin; Wu, Yan; Dalal, Seema; Cassera, Maria B; Yue, Jian-Min

    2016-08-26

    Aqueous ethanol extracts of powdered twigs of Euphorbia esula afforded 16 new diterpenoids, named euphorbesulins A-P. These euphorbesulins included presegetane (1-3), jatrophane (4-14), paraliane (15), and isopimarane (16) diterpenoids as well as six known analogues. Compounds 1-3 represent a rare type of presegetane diterpenoid. Their structures were determined by analysis of the spectroscopic data, and the absolute configuration of 1 was established by X-ray crystallography. Diterpenoid 7 showed low nanomolar antimalarial activity, while the remaining compounds showed only moderate or no antimalarial activity. PMID:27447736

  3. A new kaurane diterpenoid from Isodon inflexus.

    PubMed

    Xu, Guang-Hua; Cai, Xing-Fu; Jin, Xuejun; Lee, Jung Joon

    2016-01-01

    A new 7,20-epoxy kaurane diterpenoid, 15-acetyldemethylkamebacetal A (1) and six known kaurane diterpenoids (2-7) were isolated from the aerial parts of Isodon inflexus in nuclear transcription factor-κB (NF-κB)-dependent reporter gene assay-guided fractionation. Their chemical structures were determined on the basis of extensive spectroscopic analysis (UV, IR, MS, 1D- and 2D-NMR) and comparison with literature data. The isolated compounds were evaluated for their inhibitory effects on TNF-α-induced NF-κB activation, and all compounds exhibited NF-κB inhibitory activities with IC50 values ranging from 1.91 to 20.15 μM. PMID:26461051

  4. Iridoid Glucosides and Diterpenoids from Caryopteris glutinosa.

    PubMed

    Luo, Guoyong; Ye, Qi; Du, Baowen; Wang, Fei; Zhang, Guo-Lin; Luo, Yinggang

    2016-04-22

    Five new iridoid glucoside derivatives (1-5), three new diterpenoids (7, 12, and 15), and 11 known compounds were isolated from the aqueous EtOH extract of Caryopteris glutinosa. Cell-based estrogen biosynthesis assays indicated that caryopteriside C (3) and caryopterisoid B (12) promote the biosynthesis of estrogen E2, with EC50 values of 11.1 and 8.0 μM, respectively, in human ovarian granulosa-like KGN cells via upregulating the expression of aromatase.

  5. Isolation of three diterpenoid acids from sunflowers, as oviposition stimulants for the banded sunflower moth, Cochylis hospes.

    PubMed

    Morris, Bruce D; Charlet, Laurence D; Foster, Stephen P

    2009-01-01

    The banded sunflower moth (BSFM), Cochylis hospes Walshingham (Lepidoptera: Cochylidae) is a specialist insect, the larvae of which feed on sunflowers, Helianthus spp., and a few other species of Compositae. It is one of the most important pests of sunflower in the USA. Previous work on H. annuus, the cultivated sunflower, revealed two diterpenoids that function as oviposition stimulants for female BSFM, and that other, more polar compounds also stimulated oviposition. Using a bioassay-guided approach, we isolated three additional diterpenoids, grandifloric acid (1), 15beta-hydroxy-ent-trachyloban-19-oic acid (2), and 17-hydroxy-16alpha-ent-kauran-19-oic acid (3), from polar fractions of pre-bloom sunflower head extracts. In laboratory bioassays, purified natural samples of each of these compounds stimulated oviposition by female BSFM. Structure-activity relationships of the five diterpenoids known to stimulate oviposition by female BSFM are discussed.

  6. New 3,4-seco-Grayanane Diterpenoids from the Flowers of Pieris japonica.

    PubMed

    Cao, Lang; Li, Yanping; Li, Hongmei; Liu, Dan; Li, Rongtao

    2016-01-01

    Three new 3,4-seco-grayanane diterpenoids, neopierisoids D-F (2-4), and a new natural one, neopierisoid C (1), were isolated from the flowers of Pieris japonica. Their structures were elucidated on the basis of extensive spectroscopic analysis, including one and two dimensional (1- and 2D)-NMR, as well as high resolution-electron ionization (HR-EI)-MS. PMID:27477663

  7. A Group of ent-Kaurane Diterpenoids Inhibit Hedgehog Signaling and Induce Cilia Elongation

    PubMed Central

    Jiang, Shiyou; Du, Jiacheng; Kong, Qinghua; Li, Chaocui; Li, Yan; Sun, Handong; Pu, Jianxin; Mao, Bingyu

    2015-01-01

    The Hedgehog (Hh) signaling pathway plays important roles in the tumorigenesis of multiple cancers and is a key target for drug discovery. In a screen of natural products extracted from Chinese herbs, we identified eight ent-Kaurane diterpenoids and two triterpene dilactones as novel Hh pathway antagonists. Epistatic analyses suggest that these compounds likely act at the level or downstream of Smoothened (Smo) and upstream of Suppressor of Fused (Sufu). The ent-Kauranoid-treated cells showed elongated cilia, suppressed Smo trafficking to cilia, and mitotic defects, while the triterpene dilactones had no effect on the cilia and ciliary Smo. These ent-Kaurane diterpenoids provide new prototypes of Hh inhibitors, and are valuable probes for deciphering the mechanisms of Smo ciliary transport and ciliogenesis. PMID:26439749

  8. Leonuketal, a Spiroketal Diterpenoid from Leonurus japonicus.

    PubMed

    Xiong, Liang; Zhou, Qin-Mei; Zou, Yike; Chen, Ming-Hua; Guo, Li; Hu, Guan-Ying; Liu, Zhao-Hua; Peng, Cheng

    2015-12-18

    An architecturally complex spiroketal diterpenoid, leonuketal (1), was isolated from the aerial parts of the plant Leonurus japonicus. This compound possessed an unprecedented tetracyclic skeleton that comprised a bridged spiroketal moiety fused with a ketal-γ-lactone unit. The structure and absolute configuration were determined by spectroscopic analyses, a modified Mosher's method, and ECD (electronic circular dichroism) calculations. Leonuketal (1) showed significant vasorelaxant activity against KCl-induced contraction of rat aorta, with the EC50 value of 2.32 μM.

  9. Briarane diterpenoids from the gorgonian Dichotella gemmacea.

    PubMed

    La, Ming-Ping; Li, Jiao; Li, Cui; Tang, Hua; Liu, Bao-Shu; Sun, Peng; Zhuang, Chun-Lin; Li, Tie-Jun; Zhang, Wen

    2014-12-01

    Seven new briarane diterpenoids, gemmacolides AS-AY (1-7), were isolated together with ten known analogues (8-17) from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data and comparison with reported data. The absolute configuration of compounds was determined based on electronic circular dichroism (ECD) experiments and genetic correlations as well. Compounds 15 and 16 were reported for the first time for the gorgonian. In the preliminary in vitro bioassays, compound 5 showed potential growth inhibitory activity against MG63 cells.

  10. Optimization of recombinant expression enables discovery of novel cytochrome P450 activity in rice diterpenoid biosynthesis

    PubMed Central

    Kitaoka, Naoki; Wu, Yisheng; Xu, Meimei; Peters, Reuben J.

    2015-01-01

    The oxygenation reactions catalyzed by cytochromes P450 (CYPs) play critical roles in plant natural products biosynthesis. At the same time, CYPs are one of most challenging enzymes to functionally characterize due to the difficulty of recombinantly expressing these membrane-associated monooxygenases. In the course of investigating rice diterpenoid biosynthesis we have developed a synthetic biology approach for functional expression of relevant CYPs in Escherichia coli. In certain cases activity was observed for only one of two closely related paralogs although it seems clear that related reactions are required for production of the known diterpenoids. Here we report that optimization of the recombinant expression system enabled characterization of not only these previously recalcitrant CYPs, but also discovery of additional activity relevant to rice diterpenoid biosynthesis. Of particular interest, CYP701A8 was found to catalyze 3β-hydroxylation of syn-pimaradiene, which is presumably relevant to momilactone biosynthesis, while CYP71Z6 & 7 were found to catalyze multiple reactions, with CYP71Z6 catalyzing the production of 2α,3α-dihydroxy-ent-isokaurene via 2α-hydroxy- ent-isokaurene, and CYP71Z7 catalyzing the production of 3α-hydroxy-ent-cassadien-2- one via 2α-hydroxy-ent-cassadiene and ent-cassadien-2-one, which may be relevant to oryzadione and phytocassane biosynthesis, respectively. PMID:25758958

  11. Bicyclic sesquiterpenoids and diterpenoids in Australian crude oils

    NASA Astrophysics Data System (ADS)

    Paul Philp, R.; Gilbert, Trevor D.; Friedrich, Jane

    1981-07-01

    Bicyclanes previously reported only in heavily biodegraded Texas Gulf Coast crudes have been found to be ubiquitous in Australian crude oils of non-marine origin from four different basins. The compounds are present in oils, thought to be derived from the same or similar sources, that have undergone varying degrees of biodegradation. They are also found to be present in oils of different geological age. In addition a series of tricyclic diterpenoid hydrocarbons was common to four oils from the Gippsland Basin. Four of these compounds had the molecular formula C 20H 34 and mass spectral fragmentation patterns suggested they were mono-unsaturated diterpenoids. The presence of unsaturated diterpenoids in crude oils appears to be a unique observation. It is proposed that the diterpenoids may be the source of the bicyclanes also observed in these oils.

  12. Two new diterpenoids from Leonotis leonurus R. Br.

    PubMed

    Narukawa, Yuji; Komori, Miyuki; Niimura, Akiko; Noguchi, Hitomi; Kiuchi, Fumiyuki

    2015-01-01

    Two new diterpenoids, 14α-hydroxy-9α,13α-epoxylabd-5(6)-en-7-on-16,15-olide (1) and 13ξ-hydroxylabd-5(6),8(9)-dien-7-on-16,15-olide (2) along with six known diterpenoids were isolated from the aerial parts of Leonotis leonurus R. Br. These structures were determined on the basis of spectroscopic analyses. Some of the isolated compounds showed weak to moderate estrogen sulfotransferase inhibitory activity.

  13. New ent-kaurane diterpenoid dimer from Pulicaria inuloides.

    PubMed

    Galala, Amal A; Sallam, Amal; Abdel-Halim, Osama B; Gedara, Sahar R

    2016-11-01

    A new naturally occurring ent-kaurane diterpenoid dimer, 15β, 15'β-oxybis (ent-kaur-16-en-19-oic acid) (1) along with six known compounds, 15β-hydroxy-ent-kaur-16-en-19-oic acid (2), 15β-hydroxy-ent-kaur-16-en-19-oate-β-d-glucopyranoside (3), 6-hydroxykaempferol-3, 7-dimethyl ether (4), quercetagetin 3, 7, 3'-trimethyl ether (5), β-sitosterol (6) and β-sitosterol glucoside (daucosterol) (7) were isolated from the aerial parts of Pulicaria inuloides DC. Compounds 2-5 were isolated for the first time from genus Pulicaria. The structures of compounds 1-7 were established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with ESI-MS. The antimicrobial activity of the isolated compounds was evaluated against Staphylococcus aureus, Escherichia coli and Candida albicans. Sulphorhodamine B cytotoxic assay against HepG2 (liver cancer) cell line and ABTS antioxidant assay were carried out.

  14. Eight new diterpenoids and two new nor-diterpenoids from the stems of Croton cascarilloides.

    PubMed

    Kawakami, Susumu; Toyoda, Hiroki; Harinantenaina, Liva; Matsunami, Katsuyoshi; Otsuka, Hideaki; Shinzato, Takakazu; Takeda, Yoshio; Kawahata, Masatoshi; Yamaguchi, Kentaro

    2013-01-01

    From the stems of Croton cascarilloides, eight new diterpenoids, named crotocascarins A-H (1-8), having a crotofolane skeleton were isolated along with two new nor-diterpenoids (9 and 10), named crotocascarins α and β, derived through rearrangement of the crotofolane skeleton. The structures of these compounds were elucidated by means of extensive one- and two-dimensional NMR spectroscopic analyses. The absolute structures of the diterpene moiety were determined by application of the circular dichroism (CD) rule for the γ-lactone ring. The relative structures of the two crotofolanes (1 and 2) and one rearranged compound (9) were confirmed by X-ray crystallographic analyses. Compounds 1, 2 and 9 possessed 2-methylbutyric acid in their molecules, the absolute configuration of which was found to be 2S by comparison of its HPLC behavior with that of an authentic sample. Therefore, the absolute structures of these crotocascarins (1, 2 and 9) were unambiguously determined. The absolute structures of crotofolanes are reported for the first time in this paper.

  15. Diterpenoids and triterpenoids from Euphorbia guyoniana.

    PubMed

    Haba, Hamada; Lavaud, Catherine; Harkat, Hassina; Alabdul Magid, Abdulmagid; Marcourt, Laurence; Benkhaled, Mohammed

    2007-05-01

    Two new compounds with tigliane and cycloartane skeletons: 4,12-dideoxy(4alpha)phorbol-13-hexadecanoate (1) and 24-methylenecycloartane-3,28-diol (2), respectively, in addition of four known diterpenoids and 13 triterpenoids: 3-benzoyloxy-5,15-diacetoxy-9,14-dioxojatropha-6(17),11-diene (4), ent-abieta-8(14),13(15)-dien-16,12-olide (5), ent-8alpha,14alpha-epoxyabieta-11,13(15)-dien-16,12-olide (6), ent-3-hydroxyatis-16(17)-ene-2,14-dione (7), 3beta-hydroxytaraxer-14-en-28-oic acid (8), beta-sitosteryl-3beta-glucopyranoside-6'-O-palmitate (9), multiflorenyl acetate (10), multiflorenyl palmitate (11), peplusol (12), 24-methylenecycloartanol (3), lanosterol (13), euferol (14), butyrospermol (15), cycloartenol (16), obtusifoliol (17), cycloeucalenol (18) and beta-sitosterol (19), were isolated from the roots of Euphorbia guyoniana. Their structures were established on the basis of physical and spectroscopic analysis, including 1D and 2D homo- and heteronuclear NMR experiments (COSY, HSQC, HMBC and NOESY) and by comparison with the literature data.

  16. Diterpenoids from Callicarpa kwangtungensis and their NO inhibitory effects.

    PubMed

    Xu, Jing; Li, Shen; Sun, Xiaocong; Ma, Jun; Liu, Feng; Tong, Ling; Lee, Dongho; Ohizumi, Yasushi; Tuerhong, Muhetaer; Guo, Yuanqiang

    2016-09-01

    A phytochemical investigation of the leaves of Callicarpa kwangtungensis led to the isolation of three new diterpenoids (1-3), callipenes A-C, and eleven known analogues (4-14). Their structures were established on the basis of extensive analysis of NMR spectroscopic data, X-ray diffraction data, and experimental and calculated electronic circular dichroism spectra. Compounds 1 and 2 are rare abietane diterpenoids possessing a peroxide bridge. All of the isolates were found to inhibit LPS-induced NO production in BV-2 cells. PMID:27491749

  17. Hepatoprotective diterpenoids from the roots of Salvia grandifolia.

    PubMed

    Kang, Jie; Zhang, Ting; Li, Li; Sun, Hua; Wang, Ding-Ding; Chen, Ruo-Yun

    2016-05-01

    One new diterpenoid, grandifolia G (1), together with a known diterpenoid (6,7,8,8a-tetrahydro-6,6-dimethyl-2-oxonaphtho[1,8-bc]furan-3-yl)-4-methylfuran-3-carboxylic acid (2), was isolated from 70% EtOH extract of root of Salvia grandifolia. Their structures were determined by UV, IR, HRESIMS, NMR spectra. Compounds 1 and 2 (10 μM) exhibited hepatoprotective activities (61 and 55%) against DL-galactosamine-induced cell damage in HL-7702 cells. PMID:27086714

  18. New cembrane diterpenoids from a Hainan soft coral Sinularia sp.

    PubMed

    Yang, Bin; Zhou, Xuefeng; Huang, Hui; Yang, Xian-Wen; Liu, Juan; Lin, Xiuping; Li, Xiubao; Peng, Yan; Liu, Yonghong

    2012-09-01

    Five new cembrane diterpenoids, named sinuflexibilins A-E (1-5), along with nine other known diterpenoids (6-14), have been isolated from the organic extract of a Hainan soft coral Sinularia sp. Their structures were determined on the basis of extensive spectroscopic analyses and by comparison of their spectral data with those of related metabolites. Compound 13, flexibilide, exhibited significant inhibitory activity of NF-κB activation using the cell-based HEK293 NF-κB luciferase reporter gene assay.

  19. Fimbriatols A-J, Highly Oxidized ent-Kaurane Diterpenoids from Traditional Chinese Plant Flickingeria fimbriata (B1.) Hawkes.

    PubMed

    Ding, Gang; Fei, Jiaodong; Wang, Jing; Xie, Yong; Li, Rongtao; Gong, Ningbo; Lv, Yang; Yu, Changyuan; Zou, Zhongmei

    2016-01-01

    Fimbriatols A-J (1-10), ten new ent-kaurane diterpenoids possessing differently highly oxidized sites, were isolated from Flickingeria fimbriata (B1.) Hawkes. The structures of these new compounds were determined by HRESI-MS, NMR, CD spectra and X-ray diffraction analysis. Compound 1 displayed moderately inhibitory ratio (48.5%) compared with the positive compound NSC-87877 (81.6%) at the concentration of 0.022 μg/mL. Compounds 7-10 possess 3, 4-seco-ent-kaurane skeleton containing a disaccharide moiety with an unusual linkage at C-2' to C-1'' instead of the common linkage at C-6' to C-1'', and this is the first report in 600 more ent-kauranes found in nature, which might be originated from ent-kaurane diterpenoids through post-modified reactions of Baeyer-Villiger oxygenation and glycosylation. PMID:27484744

  20. Fimbriatols A–J, Highly Oxidized ent-Kaurane Diterpenoids from Traditional Chinese Plant Flickingeria fimbriata (B1.) Hawkes

    PubMed Central

    Ding, Gang; Fei, Jiaodong; Wang, Jing; Xie, Yong; Li, Rongtao; Gong, Ningbo; Lv, Yang; Yu, Changyuan; Zou, Zhongmei

    2016-01-01

    Fimbriatols A–J (1–10), ten new ent-kaurane diterpenoids possessing differently highly oxidized sites, were isolated from Flickingeria fimbriata (B1.) Hawkes. The structures of these new compounds were determined by HRESI-MS, NMR, CD spectra and X-ray diffraction analysis. Compound 1 displayed moderately inhibitory ratio (48.5%) compared with the positive compound NSC-87877 (81.6%) at the concentration of 0.022 μg/mL. Compounds 7–10 possess 3, 4-seco-ent-kaurane skeleton containing a disaccharide moiety with an unusual linkage at C-2′ to C-1′′ instead of the common linkage at C-6′ to C-1′′, and this is the first report in 600 more ent-kauranes found in nature, which might be originated from ent-kaurane diterpenoids through post-modified reactions of Baeyer-Villiger oxygenation and glycosylation. PMID:27484744

  1. Biochemistry and toxicology of the diterpenoid glycoside atractyloside.

    PubMed

    Obatomi, D K; Bach, P H

    1998-04-01

    Atractyloside (Atr) is a diterpenoid glycoside that occurs naturally in plants (many of which are used in ethnomedicines) found in Europe, Africa, South America, Asia and the far East. It is also present in animal grazing forage. Atr (and its analogues) may be present at levels as high as 600 mg/kg dried plant material. Consumption of the plants containing Atr or carboxyatractyloside (carboxyAtr) has caused fatal renal proximal tubule necrosis and/or centrilobular hepatic necrosis in man and farm animals. Although pure Atr and crude plant extracts disrupt carbohydrate homeostasis and induce similar pathophysiological lesions in the kidney and liver, it is also possible that the toxicity of Atr may be confounded by the presence of other natural constituents in plants. Atr competitively inhibits the adenine nucleoside carrier in isolated mitochondria and thus blocks oxidative phosphorylation. This has been assumed to explain changes in carbohydrate metabolism and the toxic effects in liver and kidney. Although the acute toxicity of Atr is well described, many aspects of Atr toxicity (subchronic and chronic toxicity, reproductive toxicity, mutagenicity and carcinogenicity) have not been investigated and pharmacokinetic and metabolism data are limited. In vitro proximal tubular cells are selectively sensitive to Atr, whereas other renal cell types are quite resistant. There are also differences in the response of liver and renal tissue to Atr. Thus, not all of the clinical, biochemical and morphological changes caused by Atr can simply be explained on the basis of inhibition of mitochondrial phosphorylation. The relevance to a wider human risk is shown by the presence of Atr analogues in dried roasted Coffea arabica beans (17.5 32 mg/kg). There are no data to help identify the risk of low dose chronic exposure in human coffee consumers, nor is there information on the levels of Atr or its analogues in other commonly consumed human foodstuffs. PMID:9651051

  2. Antibacterial Labdane Diterpenoids from Vitex vestita.

    PubMed

    Corlay, Nina; Lecsö-Bornet, Marylin; Leborgne, Erell; Blanchard, Florent; Cachet, Xavier; Bignon, Jérôme; Roussi, Fanny; Butel, Marie-Jose; Awang, Khalijah; Litaudon, Marc

    2015-06-26

    A large-scale in vitro screening of tropical plants using an antibacterial assay permitted the selection of several species with significant antibacterial activities. Bioassay-guided purification of the dichloromethane extract of the leaves of the Malaysian species Vitex vestita, led to the isolation of six new labdane-type diterpenoids, namely, 12-epivitexolide A (2), vitexolides B and C (3 and 4), vitexolide E (8), and vitexolins A and B (5 and 6), along with six known compounds, vitexolides A (1) and D (7), acuminolide (9), 3β-hydroxyanticopalic acid (10), 8α-hydroxyanticopalic acid (11), and 6α-hydroxyanticopalic acid (12). Their structures were elucidated on the basis of 1D and 2D NMR analyses and HRMS experiments. Both variable-temperature NMR spectroscopic studies and chemical modifications were performed to investigate the dynamic epimerization of the γ-hydroxybutenolide moiety of compounds 1-4. Compounds were assayed against a panel of 46 Gram-positive strains. Vitexolide A (1) exhibited the most potent antibacterial activity with minimal inhibitory concentration values ranging from 6 to 96 μM, whereas compounds 2 and 6-9 showed moderate antibacterial activity. The presence of a β-hydroxyalkyl-γ-hydroxybutenolide subunit contributed significantly to antibacterial activity. Compounds 1-4 and 6-9 showed cytotoxic activities against the HCT-116 cancer cell line (1 < IC50s < 10 μM) and human fetal lung fibroblast MRC5 cell line (1 < IC50s < 10 μM for compounds 1, 2, 7, 8, and 9).

  3. Two new C19-diterpenoid alkaloids from Aconitum straminiflorum.

    PubMed

    Qi, Yan; Zhao, Da-Ke; Zi, Shu-Hui; Zhang, Li-Mei; Guo, Cheng-Xing; Li, Gui-Qiong; Xun, Jun-Ju; Shen, Yong

    2016-01-01

    Two new C19-diterpenoid alkaloids, straconitines A (1) and B (2), were isolated from the roots of Aconitum straminiflorum. Their structures were elucidated as 14-benzoylducloudine D (1) and 6-hydroxy-14-benzoylducloudine D (2) based on spectroscopic analysis, including IR, ESI-MS, HR-ESI-MS, 1D, and 2D NMR.

  4. Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B.

    PubMed

    Boukouvalas, John; Wang, Jian-Xin; Marion, Olivier; Ndzi, Bruno

    2006-08-18

    Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.

  5. Supression of inflammatory responses by labdane-type diterpenoids

    SciTech Connect

    Giron, Natalia; Rodriguez, Benjamin; Lopez-Fontal, Raquel; Bosca, Lisardo; Hortelano, Sonsoles Heras, Beatriz de las

    2008-04-15

    A series of 11 labdane-type diterpenoids (1-11) with various patterns of substitution were tested for potential anti-inflammatory activity. Of these compounds, 4 and 11 were selected to evaluate their influence on targets relevant to the regulation of the inflammatory response. These diterpenoids reduced the production of nitric oxide (NO), prostaglandin E2, and tumor necrosis factor-{alpha} in LPS-activated RAW 264.7 macrophages, with IC50 in the range 1-10 {mu}M. Inhibition of these inflammatory mediators was related to inhibition of the expression of nitric oxide synthase-2 (NOS-2) and cyclooxygenase-2 (COX-2) at the transcriptional level, as determined by western-blot and RT-PCR. Examination of the effects of these diterpenoids on nuclear factor {kappa}B signaling showed that both compounds inhibit the phosphorylation of I{kappa}B{alpha} and I{kappa}B{beta}, preventing their degradation and the nuclear translocation of the NF-{kappa}B p65 subunit. Inhibition of IKK activity was also observed. These derivatives displayed significant anti-inflammatory activity in vivo, suppressing mouse ear edema induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) and inhibiting myeloperoxidase activity, an index of neutrophil infiltration. The anti-inflammatory effects of these labdane diterpenoids, together with their low cell toxicity, suggest potential therapeutic applications in the regulation of the inflammatory response.

  6. New clerodane diterpenoids from the aerial parts of Pulicaria wightiana.

    PubMed

    Das, Biswanath; Ramu, Ravirala; Venkateswarlu, Katta; Rao, Yerra Koteswara; Reddy, Majjigapu Ravinder; Ramakrishna, Kallaganti Venkata Siva; Harakishore, Kankipati; Murty, Upadhayula Suryanarayana

    2006-02-01

    Two new ent-clerodane-type diterpenoids, compounds 1 and 2, were isolated from the aerial parts of Pulicaria wightiana, together with three known constituents. Their structures were established based on spectroscopic data, and their antibacterial activities were evaluated (Table 2).

  7. Hydrocarbon geochemistry of the Puget Sound region - II. Sedimentary diterpenoid, steroid and triterpenoid hydrocarbons

    NASA Astrophysics Data System (ADS)

    Barrick, Robert C.; Hedges, John I.

    1981-03-01

    Cyclic components of the 'aliphatic' hydrocarbon mixtures extracted from Puget Sound sediment cores include a suite of C 19 and C 20 diterpenoid hydrocarbons of which fichtelite. sandaracopimaradiene, and isopimaradiene have been identified. Although apparently also derived from vascular plants, these diterpenoid hydrocarbons have relative abundances distinctly different from the co-existing plant wax n-alkane suite. Five C 27, C 28 and C 29 diasteranes and four C 29, C 30 and C 31 17α(H), 21β(H) hopanes occur in relatively constant proportion as components of a highly weathered fossil hydrocarbon assemblage. These chromatographically resolved cycloalkanes. along with the strongly covarying unresolved complex mixture, have been introduced to Puget Sound sediments from adjacent urban centres at increasing levels over the last 100 yr in the absence of any major oil spill. Naturally-occurring triterpenoid hydrocarbons, including hop-22(29)-ene (diploptene), are also present. A new group of C 30 polyenes has been detected which contains compounds apparently structurally related to a co-existing bicyclic C 25 diene and to C 20 and C 25 acyclic multibranched hydrocarbons described in a previous paper ( BARRICK et al., 1980).

  8. Metabolic Engineering of Synechocystis sp. PCC 6803 for Production of the Plant Diterpenoid Manoyl Oxide.

    PubMed

    Englund, Elias; Andersen-Ranberg, Johan; Miao, Rui; Hamberger, Björn; Lindberg, Pia

    2015-12-18

    Forskolin is a high value diterpenoid with a broad range of pharmaceutical applications, naturally found in root bark of the plant Coleus forskohlii. Because of its complex molecular structure, chemical synthesis of forskolin is not commercially attractive. Hence, the labor and resource intensive extraction and purification from C. forskohlii plants remains the current source of the compound. We have engineered the unicellular cyanobacterium Synechocystis sp. PCC 6803 to produce the forskolin precursor 13R-manoyl oxide (13R-MO), paving the way for light driven biotechnological production of this high value compound. In the course of this work, a new series of integrative vectors for use in Synechocystis was developed and used to create stable lines expressing chromosomally integrated CfTPS2 and CfTPS3, the enzymes responsible for the formation of 13R-MO in C. forskohlii. The engineered strains yielded production titers of up to 0.24 mg g(-1) DCW 13R-MO. To increase the yield, 13R-MO producing strains were further engineered by introduction of selected enzymes from C. forskohlii, improving the titer to 0.45 mg g(-1) DCW. This work forms a basis for further development of production of complex plant diterpenoids in cyanobacteria.

  9. Pericolactines A–C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton

    PubMed Central

    Wu, Yue-Hua; Chen, Guo-Dong; He, Rong-Rong; Wang, Chuan-Xi; Hu, Dan; Wang, Gao-Qian; Guo, Liang-Dong; Yao, Xin-Sheng; Gao, Hao

    2015-01-01

    Fusicoccane diterpenoids usually possess a fused 5-8-5 tricyclic ring system, which are biogenetically generated from geranylgeranyl diphosphate (GGDP). In our report, three novel diterpenoid alkaloids with fusicoccane skeleton, pericolactines A–C (1–3), were isolated from Periconia sp.. Their structures with absolute configurations were determined by spectroscopic analyses and quantum chemical ECD calculation. Pericolactines A–C (1–3) are a new class of diterpenoid alkaloids with an unusual fused 5-5-8-5 tetracyclic ring system, which derive from a geranylgeranyl diphosphate (GGDP) and serine conjugated biosynthesis. They belong to the atypical diterpenoid alkaloids. PMID:26611465

  10. Pericolactines A-C, a New Class of Diterpenoid Alkaloids with Unusual Tetracyclic Skeleton.

    PubMed

    Wu, Yue-Hua; Chen, Guo-Dong; He, Rong-Rong; Wang, Chuan-Xi; Hu, Dan; Wang, Gao-Qian; Guo, Liang-Dong; Yao, Xin-Sheng; Gao, Hao

    2015-11-27

    Fusicoccane diterpenoids usually possess a fused 5-8-5 tricyclic ring system, which are biogenetically generated from geranylgeranyl diphosphate (GGDP). In our report, three novel diterpenoid alkaloids with fusicoccane skeleton, pericolactines A-C (1-3), were isolated from Periconia sp.. Their structures with absolute configurations were determined by spectroscopic analyses and quantum chemical ECD calculation. Pericolactines A-C (1-3) are a new class of diterpenoid alkaloids with an unusual fused 5-5-8-5 tetracyclic ring system, which derive from a geranylgeranyl diphosphate (GGDP) and serine conjugated biosynthesis. They belong to the atypical diterpenoid alkaloids.

  11. Cytotoxic diterpenoids from Jatropha curcas cv. nigroviensrugosus CY Yang Roots.

    PubMed

    Liu, JieQing; Yang, YuanFeng; Xia, JianJun; Li, XuYang; Li, ZhongRong; Zhou, Lin; Qiu, MingHua

    2015-09-01

    An investigation of phytochemicals from the roots of Jatropha curcas cv. nigroviensrugosus resulted in the isolation of twenty diterpenoids, including lathyranlactone, an unusual diterpenoid lactone possessing a 5/13/3 tricyclic skeleton, jatrocurcasenones A-E and jatrophodiones B-E, as well as 10 known analogues. All isolates were evaluated for cytotoxicity against the HL-60, SMMC-772, A-549, MCF-7 and SW480 human tumor cell lines using the MTS viability assay. Four of the known analogues showed cytotoxic activity in these cell lines, with IC50 values ranging from 2.0 to 23.0 μM. Moreover, the assessment of their cytotoxic structure-activity relationships showed the epoxy ring between C-5 and C-6 and the hydroxyl group at C-2 were the key functionalities for cytotoxicity. PMID:26209936

  12. Cassane Diterpenoids from the Pericarps of Caesalpinia bonduc.

    PubMed

    Zhang, Panpan; Tang, Chunping; Yao, Sheng; Ke, Changqiang; Lin, Ge; Hua, Hui-Ming; Ye, Yang

    2016-01-22

    Ten new cassane-type diterpenoids, caesalbonducins D-F (1-3), 6-deacetoxybonducellpin B (4), 3-acetoxy-α-caesalpin (5), 2(3)-en-α-caesalpin (6), 1α-hydroxycaesalpinin J (7), 1α-hydroxy-6-decaetoxysalpinin J (8), 6α-hydroxycaesall M (9), and 6α-hydroxy-14(17)-dehydrocaesalpin F (10), along with eight known compounds (11-18), were isolated from the pericarps of Caesalpinia bonduc. Compounds 1-3 and 11 are methyl-migrated cassane-type diterpenoids with a 19(4→3)-cassane skeleton. The structures of 1-10 were elucidated on the basis of 1D and 2D NMR methods and other spectroscopic analysis. The neuroprotective effects of the isolated compounds were evaluated. PMID:26756595

  13. Macrocyclic Diterpenoids from the Latex of Euphorbia helioscopia.

    PubMed

    Hua, Juan; Liu, Yan-Chun; Jing, Shu-Xi; Luo, Shi-Hong; Li, Sheng-Hong

    2015-12-01

    One new jatrophane diterpenoid, 7α,9β,15β-triacetoxy-3β-benzoyloxy-14β-hydroxyjatropha-5E,11E-diene (3), together with four known macrocyclic diterpenoids, euphoheliosnoid A (1), epieuphoscopin B (2), euphohelioscopin A (4) and euphoscopin C (5), were isolated from the stem latex of Euphorbia helioscopia. Their structures were established by spectroscopic analyses. In the anti-inflammatory assay, euphohelioscopin A (4) exhibited moderate inhibitory activity on the release of cytokine TNF-α (IC50 = 23.7 ± 1.7 μM), IL-6 (IC50 = 46.1 ± 1.1 μM) and chemokine MCP-1 (IC50 = 33.7 ± 3.8 μM) in lipopolysaccharide (LPS) induced RAW 264.7 macrophages without notable cytotoxicity (IC50 > 80 μM). PMID:26882659

  14. The Chemistry of Perfumes Based on Labdane Diterpenoids

    NASA Astrophysics Data System (ADS)

    Vlad, Pavel F.

    1982-07-01

    The advances in the synthesis of C14-C19 perfumes derived from bicyclic labdane diterpenoids and their enantiomers as well as data concerning the sources of the starting materials are presented. The dependence of the odour of the above compounds on their structure and stereochemistry and the questions arising in the manufacture of some of them and their practical applications are considered. The bibliography includes 242 references

  15. Bis-spirolabdane-type diterpenoids from Leonurus sibiricus.

    PubMed

    Moon, Hyun Teak; Jin, Qinglong; Shin, Ji Eun; Choi, Eun Jin; Han, Hyo-Kyung; Kim, Yeong Shik; Woo, Eun-Rhan

    2010-02-26

    Six new bis-spirolabdane-type diterpenoids, leosibirinone A (1), 3alpha-acetoxyleoheteronone C (2), leosibirinone B (3), 3alpha-hydroxyleoheteronone A (4), 3alpha-acetoxyleoheteronone E (5), and 3alpha-acetoxy-15-epileoheteronone E (6), were isolated from the aerial parts of Leonurus sibiricus. Their structures were identified on the basis of 1D and 2D NMR, including (1)H-(1)H COSY, HSQC, HMBC, and NOESY spectroscopic analyses.

  16. Anti-inflammatory diterpenoids from the root bark of Acanthopanax gracilistylus.

    PubMed

    Wu, Zhi-Yuan; Zhang, Yi-Bei; Zhu, Kong-Kai; Luo, Cheng; Zhang, Jing-Xian; Cheng, Chun-Ru; Feng, Rui-Hong; Yang, Wen-Zhi; Zeng, Feng; Wang, Yang; Xu, Ping-Ping; Guo, Ji-Ling; Liu, Xuan; Guan, Shu-Hong; Guo, De-An

    2014-11-26

    Five new ent-pimarane (1-3, 7, and 8) and three new ent-kaurane diterpenoids (4-6) and a new oleanane triterpene acid (9), together with 22 known compounds, were isolated from the root bark of the medicinal herb Acanthopanax gracilistylus. The structures of 1-9 were established based on the interpretation of high-resolution MS and 1D- and 2D-NMR data. The absolute configurations of 7 and 11 were determined by single-crystal X-ray diffraction and electronic circular dichroism analysis. Compounds 7 and 8 represent rare naturally occurring structures based on the devinyl ent-pimarane skeleton. Compounds 3, 10, 14, 16, and 17 exhibited potent inhibitory effects on the release of interleukin-1β (IL-1β), interleukin-8 (IL-8), and tumor necrosis factor (TNF-α) in lipopolysaccharide-stimulated peripheral blood mononuclear cells. PMID:25338180

  17. Labdane-type diterpenoids from Leonurus heterophyllus and their cholinesterase inhibitory activity.

    PubMed

    Hung, Tran Manh; Luan, Tran Cong; Vinh, Bui The; Cuong, To Dao; Min, Byung Sun

    2011-04-01

    In the course of screening plants used in natural medicines as memory enhancers, a 70% ethanol extract of the aerial parts of Leonurus heterophyllus showed significant AChE inhibitory activity. Bioassay-guided fractionation and repeated column chromatography led to the isolation of a new labdane-type diterpenoids (1), named leoheteronin F, and six known compounds (2-7). The chemical structures of isolated compounds were elucidated based on extensive 1D and 2D NMR spectroscopic data. The isolates 1-7 were investigated in vitro for their anticholinesterase activity using mouse cortex AChE enzyme. Leoheteronin A (5) and leopersin G (7), which possess a 15,16-epoxy group at the side chain, were found to be potent in the inhibition of AChE.

  18. Semisynthesis of the antiviral abietane diterpenoid jiadifenoic acid C from callitrisic acid (4-epidehydroabietic acid) isolated from sandarac resin.

    PubMed

    González, Miguel A; Zaragozá, Ramón J

    2014-09-26

    The semisynthesis of the antiviral abietane diterpenoid (+)-jiadifenoic acid C starting from the available methyl ester of callitrisic acid (4-epidehydroabietic acid) isolated from sandarac resin is reported. A protocol for the isolation of methyl callitrisate (methyl 4-epidehydroabietate) in gram quantities from sandarac resin is also described. Allylic C-17 oxygenation was introduced by regioselective dehydrogenation of the isopropyl group of methyl callitrisate with DDQ followed by selenium-catalyzed allylic oxidation. Ester hydrolysis afforded (+)-jiadifenoic acid C in 22% overall yield from methyl callitrisate. This semisynthetic route provides a convenient source of this anti-Coxsackie virus B natural product for further biological studies. PMID:25166492

  19. Phenolic Diterpenoid Derivatives as Anti-Influenza A Virus Agents

    PubMed Central

    2015-01-01

    A series of diterpenoid derivatives based on podocarpic acid were synthesized and evaluated as anti-influenza A virus agents. Several of the novel podocarpic acid derivatives exhibited nanomolar activities against an H1N1 influenza A virus (A/Puerto Rico/8/34) that was resistant to two anti-influenza drugs, oseltamivir and amantadine. This class of compounds inhibits the influenza virus by targeting the viral hemagglutinin-mediated membrane fusion. These results indicated that podocarpic acid derivatives may serve as potential drug candidates to fight drug-resistant influenza A virus infections. PMID:25815159

  20. Diterpenoids from Croton laui and their cytotoxic and antimicrobial activities.

    PubMed

    Liu, Cui-Ping; Xu, Jin-Biao; Zhao, Jin-Xin; Xu, Cheng-Hui; Dong, Lei; Ding, Jian; Yue, Jian-Min

    2014-04-25

    Fourteen new diterpenoids including clerodane (1-12), labdane (13), and norlabdane (14) types, as well as nine known analogues were isolated from the aerial parts of Croton laui. Their structures were established on the basis of spectroscopic analysis, and that of crotonolide H (11) was confirmed by single-crystal X-ray crystallography. Crotonolide A (1) exhibited moderate cytotoxicity against two tumor cell lines, HL-60 (human premyelocytic leukemia, IC50 9.42 μM) and P-388 (murine leukemia, IC50 7.45 μM), and crotonolide G (10) displayed significant antibacterial activity against a panel of Gram-positive bacteria.

  1. Cytotoxic ent-kaurane diterpenoids from Isodon nervosus.

    PubMed

    Gao, You-Heng; Wei, Zhi-Xiong; Cheng, Yi; Wang, Teng-Hua; Ni, Lin; Zhou, Xiao-Hong; Zhang, Li-Yuan

    2013-08-01

    Four new ent-kaurane diterpenoids, rabdonervosins G-J (1-4, resp.), were isolated from the leaves and stems of Isodon nervosus. Their structures were elucidated by extensive spectroscopic analyses, including 1D-, 2D-NMR and HR mass spectra. Compound 2 showed potent cytotoxicity against the HepG2 and PC-9/ZD cell lines with IC50 values of 2.36 and 6.07 μM, respectively, and compound 3 exhibited cytotoxicity against the HepG2 and CNE2 cell lines with IC50 values of 8.64 and 9.77 μM, respectively. PMID:23939796

  2. Bioactive ent-kaurane diterpenoids from Isodon rosthornii.

    PubMed

    Zhan, Rui; Li, Xiao-Nian; Du, Xue; Wang, Wei-Guang; Dong, Ke; Su, Jia; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong

    2013-07-26

    Isorosthin A (1), the first 20-nor-enmein-type diterpenoid, and 15 new ent-kauranoids, isorosthins B-P (2-16), along with 22 known analogues were isolated from the aerial parts of Isodon rosthornii. The structures of 1-16 were elucidated by means of spectroscopic analysis. The relative configuration of 2 and the absolute configuration of 3 were determined by single-crystal X-ray diffraction. Cytotoxicity evaluation against five human tumor lines showed inhibitory effects by several of the compounds tested. Furthermore, 12 of the isolates exhibited inhibitory activity against nitric oxide production in LPS-activated RAW264.7 macrophages. PMID:23819871

  3. Anti-inflammatory Labdane Diterpenoids from Leonurus macranthus.

    PubMed

    Huang, Zheng; Zhu, Zhi-Xiang; Li, Yue-Ting; Pang, Dao-Ran; Zheng, Jiao; Zhang, Qian; Zhao, Yun-Fang; Ferreira, Daneel; Zjawiony, Jordan K; Tu, Peng-Fei; Li, Jun

    2015-09-25

    Twenty new polyoxygenated labdane diterpenoids (1-20) were isolated from the aerial parts of Leonurus macranthus. Their structures were elucidated on the basis of spectroscopic and spectrometric data (1D and 2D NMR, IR, and HRESIMS). The absolute configurations of macranthin A (1) and 6-O-deacetylmacranthin A (2) were determined by single-crystal X-ray crystallographic analysis and a modified Mosher's method, respectively. Compounds 1-9, 12, 14, and 19 showed inhibition of nitric oxide production in lipopolysaccharide-activated BV-2 microglial cells with IC50 values of 10.0-63.7 μM.

  4. Antimicrobial diterpenoids from Eupatorium glutinosum (Asteraceae).

    PubMed

    El-Seedi, H R; Ohara, T; Sata, N; Nishiyama, S

    2002-07-01

    The antimicrobial properties of the hexane extract from the leaves and twigs of the Eupatorium glutinosum was tested against two Gram-negative and two Gram-positive bacteria. Bioassay guided fractionation leads characteristically to isolation and structure elucidation of two active compounds: 15-hydroxy-7-labden-17-oic acid and its acetate. These results validate the vernacular medicinal uses of the plant in folkloric medicine. Dammara-20, 24-dien-3-acetate, stigmasterol and epi-friedelanone have been also isolated in addition to the palmitate of nepehinol for the first time as naturally occurring. PMID:12065166

  5. Diterpenoids from the twigs and leaves of Croton caudatus var. tomentosus.

    PubMed

    Song, Jin-Tong; Han, Yang; Wang, Xiao-Ling; Shen, Tao; Lou, Hong-Xiang; Wang, Xiao-Ning

    2015-12-01

    One new 9,10-seco-abietane derivative, crotontomentosin A (1), four new abietane-type diterpenoids, crotontomentosins B-E (2-5), one new ent-halimane-type diterpenoid, crotontomentosin F (6), along with five known diterpenoids (7-11) and one known sesquiterpenoid (12) were obtained from the twigs and leaves of Croton caudatus Geisel. var. tomentosus Hook. The structures of the compounds were established on the basis of extensive spectroscopic data. Compounds 1-4 and 11 exhibited moderate to weak inhibitory activity against the proliferation of the Hela, Hep G2, MDA-MB-231, or A549 cell lines selectively.

  6. Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals

    PubMed Central

    Zhou, Ke; Xu, Meimei; Tiernan, Mollie; Xie, Qian; Toyomasu, Tomonobu; Sugawara, Chizu; Oku, Madoka; Usui, Masami; Mitsuhashi, Wataru; Chono, Makiko; Chandler, Peter M.; Peters, Reuben J.

    2012-01-01

    Wheat (Triticum aestivum) and rice (Oryza sativa) are two of the most agriculturally important cereal crop plants. Rice is known to produce numerous diterpenoid natural products that serve as phytoalexins and/or allelochemicals. Specifically, these are labdane-related diterpenoids, derived from a characteristic labdadienyl/copalyl diphosphate (CPP), whose biosynthetic relationship to gibberellin biosynthesis is evident from the relevant expanded and functionally diverse family of ent-kaurene synthase-like (KSL) genes found in rice (OsKSL). Here we report biochemical characterization of a similarly expansive family of KSL from wheat (the TaKSLs). In particular, beyond ent-kaurene synthases (KS), wheat also contains several biochemically diversified KSLs. These react either with the ent-CPP intermediate common to gibberellin biosynthesis or with the normal stereoisomer of CPP that also is found in wheat (as demonstrated by the accompanying description of wheat CPP synthases). Comparison with a barley (Hordeum vulgare) KS indicates conservation of monocot KS, with early and continued expansion and functional diversification of KSLs in at least the small grain cereals. In addition, some of the TaKSLs that utilize normal CPP also will react with syn-CPP, echoing previous findings with the OsKSL family, with such enzymatic promiscuity/plasticity providing insight into the continuing evolution of diterpenoid metabolism in the cereal crop plant family, as well as more generally, which is discussed here. PMID:23009879

  7. Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals.

    PubMed

    Zhou, Ke; Xu, Meimei; Tiernan, Mollie; Xie, Qian; Toyomasu, Tomonobu; Sugawara, Chizu; Oku, Madoka; Usui, Masami; Mitsuhashi, Wataru; Chono, Makiko; Chandler, Peter M; Peters, Reuben J

    2012-12-01

    Wheat (Triticum aestivum) and rice (Oryza sativa) are two of the most agriculturally important cereal crop plants. Rice is known to produce numerous diterpenoid natural products that serve as phytoalexins and/or allelochemicals. Specifically, these are labdane-related diterpenoids, derived from a characteristic labdadienyl/copalyl diphosphate (CPP), whose biosynthetic relationship to gibberellin biosynthesis is evident from the relevant expanded and functionally diverse family of ent-kaurene synthase-like (KSL) genes found in rice the (OsKSLs). Herein reported is the biochemical characterization of a similarly expansive family of KSL from wheat (the TaKSLs). In particular, beyond ent-kaurene synthases (KS), wheat also contains several biochemically diversified KSLs. These react either with the ent-CPP intermediate common to gibberellin biosynthesis or with the normal stereoisomer of CPP that also is found in wheat (as demonstrated by the accompanying paper describing the wheat CPP synthases). Comparison with a barley (Hordeum vulgare) KS indicates conservation of monocot KS, with early and continued expansion and functional diversification of KSLs in at least the small grain cereals. In addition, some of the TaKSLs that utilize normal CPP also will react with syn-CPP, echoing previous findings with the OsKSL family, with such enzymatic promiscuity/elasticity providing insight into the continuing evolution of diterpenoid metabolism in the cereal crop plant family, as well as more generally, which is discussed here.

  8. Rapid separation and characterization of diterpenoid alkaloids in processed roots of Aconitum carmichaeli using ultra high performance liquid chromatography coupled with hybrid linear ion trap-Orbitrap tandem mass spectrometry.

    PubMed

    Xu, Wen; Zhang, Jing; Zhu, Dayuan; Huang, Juan; Huang, Zhihai; Bai, Junqi; Qiu, Xiaohui

    2014-10-01

    The lateral root of Aconitum carmichaeli, a popular traditional Chinese medicine, has been widely used to treat rheumatic diseases. For decades, diterpenoid alkaloids have dominated the phytochemical and biomedical research on this plant. In this study, a rapid and sensitive method based on ultra high performance liquid chromatography coupled with linear ion trap-Orbitrap tandem mass spectrometry was developed to characterize the diterpenoid alkaloids in Aconitum carmichaeli. Based on an optimized chromatographic condition, more than 120 diterpenoid alkaloids were separated with good resolution. Using a systematic strategy that combines high resolution separation, highly accurate mass measurements and a good understanding of the diagnostic fragment-based fragmentation patterns, these diterpenoid alkaloids were identified or tentatively identified. The identification of these chemicals provided essential data for further phytochemical studies and toxicity research of Aconitum carmichaeli. Moreover, the ultra high performance liquid chromatography with linear ion trap-Orbitrap mass spectrometry platform was an effective and accurate tool for rapid qualitative analysis of secondary metabolite productions from natural resources.

  9. Diterpenoid compounds and other lipids in deep-sea sediments and their geochemical significance

    NASA Technical Reports Server (NTRS)

    Simoneit, B. R. T.

    1977-01-01

    Cyclic diterpenoid compounds have been found by various investigators in the geosphere (e.g., fossil resins, coals, soil, shale, and deep-sea sediments). These compounds occur in significant amounts only in higher plants and are therefore potential markers of terrigenous plant lipids. Diterpenoids with the abietane skeleton (mainly dehydroabietic acid) have been identified in the lipids of sediment samples from the northeast Pacific Ocean, Black Sea, and North Atlantic Ocean. The presence of these resin-derived compounds was correlated with the terrigenous clay components and with the presence of pollen. The presence of polycyclic diterpenoids was also correlated with the distribution patterns and inferred sources of other sediment lipid constituents. Potamic transport, followed by turbidite redistribution, is the probable input mechanism of these resin-derived compounds to the deep-sea sediments. These diterpenoids appear to be excellent biological markers of resinous higher plants.

  10. Hapmnioides A-C, Rearranged Labdane-Type Diterpenoids from the Chinese Liverwort Haplomitrium mnioides.

    PubMed

    Zhou, Jinchuan; Zhang, Jiaozhen; Li, Ruijuan; Liu, Jun; Fan, Peihong; Li, Yi; Ji, Mei; Dong, Yiwen; Yuan, Huiqing; Lou, Hongxiang

    2016-09-01

    Many exceptional labdane-type diterpenoids have been exclusively found in liverworts, which serve as taxonomic molecules or play important ecological roles in interactions among organisms. Three unprecedented labdane-type diterpenoids hapmnioides A (1), B (2), and C (3) formed through cascade rearrangement from the Chinese liverwort Haplomitrium mnioides are reported. Their structures were established by comprehensive spectroscopic analysis coupled with single-crystal X-ray diffraction, and their anti-inflammatory activities were also preliminarily tested. PMID:27513610

  11. Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans.

    PubMed

    Chu, Rui; Wan, Luo-Sheng; Peng, Xing-Rong; Yu, Mu-Yuan; Zhang, Zhi-Run; Zhou, Lin; Li, Zhong-Rong; Qiu, Ming-Hua

    2016-08-01

    Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

  12. Bis-spirolabdane diterpenoids from Leonurus japonicus and their anti-platelet aggregative activity.

    PubMed

    Xiong, Liang; Zhou, Qin-Mei; Peng, Cheng; Xie, Xiao-Fang; Liu, Lu-Si; Guo, Li; He, Ya-Cong; Yang, Lian; Liu, Zhao-Hua

    2015-01-01

    Six bis-spirolabdane diterpenoids along with four known analogues were isolated from the aerial parts of Leonurus japonicus. Their structures and absolute configurations were elucidated by spectroscopic analyses, single-crystal X-ray diffraction, and a modified Mosher's method. The inhibitory activity of the compounds against the abnormal increase in platelet aggregation induced by adenosine diphosphate was investigated. Only the (13R)-bis-spirolabdane diterpenoids exhibited a significant effect.

  13. New briarane-type diterpenoids from gorgonian Ellisella dollfusi from the South China Sea.

    PubMed

    Zhou, Yuan-Ming; Shao, Chang-Lun; Huang, Hui; Zhang, Xiu-Li; Wang, Chang-Yun

    2014-01-01

    Two new briarane-type diterpenoids, dollfusilin A (1) and dollfusilin B (2), along with five known briarane-type diterpenoids (3-7), were isolated from the gorgonian Ellisella dollfusi collected from the South China Sea. The structures of the two new compounds (1 and 2) were elucidated through a comprehensive analysis of spectroscopic data, especially 2D NMR. The bioactivities of the isolated compounds were evaluated using the zebrafish toxicity model.

  14. Further Studies on Structure-Cardiac Activity Relationships of Diterpenoid Alkaloids.

    PubMed

    Zhang, Zhong-Tang; Jian, Xi-Xian; Ding, Jia-Yu; Deng, Hong-Ying; Chao, Ruo-Bing; Chen, Qiao-Hong; Chen, Dong-Lin; Wang, Feng-Peng

    2015-12-01

    The cardiac effect of thirty-eight diterpenoid alkaloids was evaluated on the isolated bullfrog heart model. Among them, twelve compounds exhibited appreciable cardiac activity, with compounds 3 and 35 being more active than the reference drug lanatoside. The structure-cardiac activity relationships of the diterpenoid alkaloids were summarized based on our present and previous studies [2]: i) 1α-OMe or 1α-OH, 8-OH, 14-OH, and NH (or NMe) are key structural features important for the cardiac effect of the aconitine-type C19-diterpenoid alkaloids without any esters. C18-diterpenoid alkaloids, lycoctonine-type C19-diterpenoid alkaloids, and the veatchine- and denudatine-type C20-diterpenoid alkaloids did not show any cardiac activity; ii) the presence of 3α-OH is beneficial to the cardiac activity; iii) the effect on the cardiac action of 6α-OMe, 13-OH, 15α-OH, and 16-demethoxy or a double bond between C-15 and C-16 depends on the substituent pattern on the nitrogen atom.

  15. Two new labdane diterpenoids from the rhizomes of Isodon yuennanensis.

    PubMed

    Huang, Zhen-Yuan; Huang, Bo; Xiao, Chao-Jiang; Dong, Xiang; Jiang, Bei

    2015-01-01

    Two new labdane diterpenoids, s-trans-8(17),12E,14-labdatrien-20-oic acid (1), s-trans-12E,14-labdadien-20,8β-olide (2), along with 10 known compounds, hinokiol (3), ursonic acid (4), 2α,3α-dihydroxyolean-12-en-28-oic acid (5), 2α,3β,23-trihydroxyolean-12-en-28-oic acid (6), ethyl 3-(3,4-dihydroxyphenyl)lactate (7), ethyl rosmarinate (8), (Z,E)-2-(3,4-dihydroxyphenyl)ethenyl caffeic ester (9), tridecanoic acid (10), β-sitosterol (11) and daucosterol (12), were isolated from the 70% acetone extract of the rhizomes of Isodon yuennanensis. Their structures were elucidated based on the analyses of extensive spectroscopic data and physicochemical properties. PMID:25420949

  16. Cytotoxic ent-kaurane diterpenoids from Isodon wikstroemioides.

    PubMed

    Wu, Hai-Yan; Zhan, Rui; Wang, Wei-Guang; Jiang, Hua-Yi; Du, Xue; Li, Xiao-Nian; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong

    2014-04-25

    Phytochemical investigation of EtOAc extracts of the aerial parts of Isodon wikstroemioides afforded 18 new ent-kaurane diterpenoids (wikstroemioidins E-V, 1-18), along with 17 known analogues (19-35). The absolute configurations of 1 and 16 were confirmed by single-crystal X-ray diffraction analysis. The isolates were screened against five human tumor cell lines; compounds 3, 4, 9, 11-13, 23, 25-28, and 33 exhibited significant cytotoxic activity against all five, with IC50 values ranging from 0.4 to 5.1 μM. In addition, 17 of the isolates strongly inhibited nitric oxide production in LPS-activated RAW264.7 macrophages. PMID:24697496

  17. Minor ent-abietane diterpenoids from Euphorbia guyoniana.

    PubMed

    Haba, Hamada; Marcourt, Laurence; Benkhaled, Mohammed; Long, Christophe

    2013-11-01

    Three new abietane-type diterpenoids: ent-abieta-8,11,13-trien-16-ol (1), ent-abieta-8,11,13-trien-11,16-diol (2) and 11,12-dihydroxy-7-oxo-ent-abieta-8,11,13-trien-16-oic acid methyl ester (3), in addition to three known triterpenoids: euphol (4), 24,25-epoxycycloartanol (5) and beta-sitosterol O-beta-D-glucoside (6) were isolated from the chloroform extract of the roots of Euphorbia guyoniana. Structures of the isolated compounds were established on the basis of spectroscopic analyses, including 1D and 2D homo and heteronuclear NMR experiments and ESIMS, and comparison with literature data.

  18. Cytotoxic diterpenoid pseudodimers from the Korean sponge Phorbas gukhulensis.

    PubMed

    Jeon, Ju-eun; Liao, Lijuan; Kim, Heegyu; Sim, Chung J; Oh, Dong-Chan; Oh, Ki-Bong; Shin, Jongheon

    2013-09-27

    Four new cytotoxic diterpenoid pseudodimers (2-5), along with a previously reported one, gukulenin A (1), were isolated from the marine sponge Phorbas gukhulensis collected off the coast of Gagu-do, Korea. These novel compounds, designated gukulenins C-F (2-5), were determined by extensive spectroscopic analyses to be pseudodimers of the gagunins, like gukulenin A. The termini of the tropolone-containing side chains in gukulenins C-E (2-4) were found to have diverse modifications involving acetamides or taurine, whereas gukulenin F (5) was formed from 1 by the ring-opening of a cyclic hemiketal. The relative and absolute configurations were assigned by Murata's and modified Snatzke's methods using a HETLOC experiment and a CD measurement of a dimolybdenum complex, respectively. All of these compounds exhibited significant cytotoxicity against the K562 and A549 cell lines.

  19. Cytotoxic diterpenoid pseudodimers from the Korean sponge Phorbas gukhulensis.

    PubMed

    Jeon, Ju-eun; Liao, Lijuan; Kim, Heegyu; Sim, Chung J; Oh, Dong-Chan; Oh, Ki-Bong; Shin, Jongheon

    2013-09-27

    Four new cytotoxic diterpenoid pseudodimers (2-5), along with a previously reported one, gukulenin A (1), were isolated from the marine sponge Phorbas gukhulensis collected off the coast of Gagu-do, Korea. These novel compounds, designated gukulenins C-F (2-5), were determined by extensive spectroscopic analyses to be pseudodimers of the gagunins, like gukulenin A. The termini of the tropolone-containing side chains in gukulenins C-E (2-4) were found to have diverse modifications involving acetamides or taurine, whereas gukulenin F (5) was formed from 1 by the ring-opening of a cyclic hemiketal. The relative and absolute configurations were assigned by Murata's and modified Snatzke's methods using a HETLOC experiment and a CD measurement of a dimolybdenum complex, respectively. All of these compounds exhibited significant cytotoxicity against the K562 and A549 cell lines. PMID:24025124

  20. Diterpenoids from the branch and leaf of Abies fargesii.

    PubMed

    Wu, Wen-Ming; Liu, Ye; Chen, Xu; Jin, An; Zhou, Ming; Tian, Tian; Ruan, Han-Li

    2016-04-01

    Five new abietane diterpenoids, named abifadines A-E (1-5), and nine known ones (6-14), together with two known podocarpenes (15 and 16), were isolated from the branch and leaf of Abies fargesii. Their structures including the relative configurations were established on the basis of extensive spectroscopic analyses. The absolute configuration of 1 was determined through single-crystal X-ray diffraction analysis with Cu Kα irradiation. All the isolates were evaluated for their in vitro cytotoxicities. Only compounds 5 and 12 exhibited weak anti-proliferative effects against three cancer cell lines (B16, MCF7, and HepG2) with IC50 values range from 14.8 to 42.8 μM. The antimicrobial activities against Staphylococcus aureus, Escherichia coli and Monilia albicans of all compounds were also tested, but none of them showed significant activities. PMID:26969787

  1. Tetracyclic diterpenoid hydrocarbons in some Australian coals, sediments and crude oils

    NASA Astrophysics Data System (ADS)

    Noble, Rohinton A.; Alexander, Robert; Kagi, Robert Ian; Knox, John

    1985-10-01

    Tetracyclic diterpenoid hydrocarbons (diterpanes) based on the ent-beyerane, phyllocladane and ent-kaurane skeletons have been identified in the hydrocarbon extracts of some Australian coals, sediments and crude oils. Structures were assigned to the geological diterpanes by comparison with synthetically prepared reference compounds. Studies of a sample suite consisting of low-rank coals and sediments indicate that the ratios of C-16 epimers of phyllocladane and ent-kaurane are maturity dependent, and that the relative proportion of the thermodynamically preferred 16β (H)-compounds increases with increasing thermal maturity. Thermodynamic equilibrium for the interconversion reactions is attained in sediments before the onset of crude oil generation. The most likely natural product precursors for the tetracyclic diterpanes are considered to be the tetracyclic diterpene hydrocarbons which occur widely in the leaf resins of conifers. Tetracyclic diterpanes have been identified in sediments and coals of Permian age or younger, suggesting that these compounds are markers for both modern and extinct families of conifers. In particular, phyllocladane is proposed as a marker for the Podocarpaceae family of conifers.

  2. Abietane diterpenoids from Salvia sclarea transformed roots as growth inhibitors of pathogenic Acanthamoeba spp.

    PubMed

    Kuźma, Łukasz; Derda, Monika; Hadaś, Edward; Wysokińska, Halina

    2015-01-01

    Amoebae from the genus Acanthamoeba are known agents leading to various diseases such as granulomatous amoebic encephalitis (GAE), a chronic progressive disease of the central nervous system, amoebic keratitis (AK), chronic eye infection, amoebic pneumitis (AP), chronic lung infection, and skin infections. It is known that various synthetic anti-Acanthamoeba substances are ineffective. Therefore, other substances, e.g., natural plant compounds, are the focus of biological investigations regarding anti-parasite activity. In this work, the ability of four abietane diterpenoids (ferruginol, salvipisone, aethiopinone, and 1-oxo-aethiopinone) to inhibit Acanthamoeba growth is reported. All investigated compounds were active against Acanthamoeba growing in vitro. Among them, ferruginol demonstrated the highest activity against Acanthamoeba. This compound inhibited Acanthamoeba growth by about 72% in a 3-day exposure period (IC50 17.45 μM), while aethiopinone and 1-oxo-aethiopinone demonstrated this activity at the level of 55-56%. Salvipisone reduced the growth of Acanthamoeba in vitro culture by 39%. For this compound, the value of IC50 was 701.94 μM after 72 h of exposure.

  3. Antileishmanial and Cytotoxic Activity of Some Highly Oxidized Abietane Diterpenoids from the Bald Cypress, Taxodium distichum.

    PubMed

    Naman, C Benjamin; Gromovsky, Anthony D; Vela, Cory M; Fletcher, Joshua N; Gupta, Gaurav; Varikuti, Sanjay; Zhu, Xiaohua; Zywot, Emilia M; Chai, Heebyung; Werbovetz, Karl A; Satoskar, Abhay R; Kinghorn, A Douglas

    2016-03-25

    Two new compounds, namely, a para-benzoquinone ring-containing abietane (1) and a para-benzoquinone ring-containing 7,8-seco-abietane (2), and 14 other known highly oxidized abietane diterpenoids (3-16) were isolated from an extract prepared from the cones of Taxodium distichum, collected in central Ohio. The active subfraction from which all compounds isolated in this study were purified was tested in vivo using Leishmania donovani-infected mice and was found to dose-dependently reduce the parasite burden in the murine livers after iv administration of this crude mixture at 5.6 and 11.1 mg/kg. The structures of 1 and 2 were established by detailed 1D- and 2D-NMR experiments, HRESIMS data, and electronic circular dichroism studies. Compounds 3 and 4 were each fully characterized spectroscopically and also isolated from a natural source for the first time. Compounds 2-16 were tested in vitro against L. donovani promastigotes and L. amazonensis intracellular amastigotes. Compound 2 was the most active against L. amazonensis amastigotes (IC50 = 1.4 μM), and 10 was the most potent against L. donovani promastigotes (IC50 = 1.6 μM). These compounds may be suggested for further studies such as in vivo experimentation either alone or in combination with other Taxodium isolates. PMID:26905523

  4. New C20-diterpenoid alkaloids from Aconitum vilmorrianum and structural revision of 2-O-acetylorochrine and orochrine.

    PubMed

    Tang, Tian-Xing; Chen, Qi-Feng; Liu, Xiao-Yu; Jian, Xi-Xian; Wang, Feng-Peng

    2016-01-01

    Three new C20-diterpenoid alkaloids vilmorrianines E (1), F (2), and G (3) were isolated from the whole plants of Aconitum vilmorrianum, along with one artifact N-chloromethyl vilmorrianine E hydrochloride (4), as well as two known alkaloids hemsleyaconitines F (5) and G (6). The structures of 1-4 were established by HR-ESI-MS, 1D-, 2D-NMR (HMQC, HMBC, and NOESY), and single-crystal X-ray diffraction analysis. In addition, the structures of naturally occurring 2-O-acetylorochrine (7) and orochrine (8) were revised to be the known alkaloids heterophylloidine (9) and deacetyl heterophylloidine (10), respectively, on the basis of consideration of transannular effect and chemical correlations.

  5. A bicyclic diterpenoid with a new 15,16-dinorlabdane carbon skeleton from Leonurus japonicus and its coagulant bioactivity.

    PubMed

    Peng, Fu; Xiong, Liang; Zhao, Xiao-Mei

    2013-01-01

    A new 15,16-dinorlabdane diterpenoid 1 and a known labdane diterpenoid 2, together with three known ergosterols 3-5, were isolated from the EtOAc-soluble portion of the EtOH extract of Leonurus japonicus. Their structures were elucidated by physical and spectroscopic analysis. Compound 1 showed in vitro coagulant activity in the APTT, PT, TT, and FIB assays.

  6. Bioactive ent-kaurane diterpenoids from Isodon serra.

    PubMed

    Wan, Jun; Liu, Miao; Jiang, Hua-Yi; Yang, Jin; Du, Xue; Li, Xiao-Nian; Wang, Wei-Guang; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong

    2016-10-01

    Nine 7,20-epoxy-ent-kaurane diterpenoids (15-acetylmegathyrin B, serrin E, 14β-hydroxyrabdocoestin A, serrin F, serrin G, 11-epi-rabdocoestin A, serrin H, serrin I, and 15-acetylenanderianin N), along with seven known ones, were isolated from the aerial parts of Isodon serra. Their structures were elucidated by extensive spectroscopic analysis, and the absolute configuration of 15-acetylmegathyrin B was determined by signal-crystal X-ray diffraction. All of these compounds were evaluated for their cytotoxic activities against five human tumor cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480). Serrin F, rabdocoestin B and 1α,11β-dihydroxy-1α,11β-acetonide-7α,20-epoxy-ent-kaur-16-en-15-one showed cytotoxic activities against all cell lines, with IC50 values ranging from 0.7 to 4.6 μM; serrin F also strongly inhibited NO production in LPS-stimulated RAW264.7 cells. Otherwise, 14β-hydroxyrabdocoestin A, serrins H and I, as well as enanderianin N and megathyrin B, also exhibited inhibitory effects towards NO production, while no cytotoxicity against five cell lines was detected. PMID:27298277

  7. Clerodane-type diterpenoids from tuberous roots of Tinospora sagittata (Oliv.) Gagnep.

    PubMed

    Zhang, Geng; Ma, Haoran; Hu, Song; Xu, Hongfeng; Yang, Bo; Yang, Quanwei; Xue, Yongbo; Cheng, Lu; Jiang, Jie; Zhang, Jinwen; Wang, Fuqian; Zhang, Yonghui

    2016-04-01

    Three new clerodane type diterpenoids (2-4), together with one known analogues (1), were isolated from the tuberous roots of Tinospora sagittata (Oliv.) Gagnep. Compound 3 is an unusual clerodane diterpenoid with the carbonyl functionality at C-3, which represents the first example from this diterpenoid compounds class. The structures were established on the basis of spectroscopic data interpretation. The absolute configuration of 1 was determined for the first time by single-crystal X-ray diffraction analysis with CuKα irradiation. These isolates were evaluated for their cytotoxic activities against five human cancer cell lines and inhibitory activities on LPS-induced NO production in RAW264.7 cells. PMID:26924160

  8. Bioactive diterpenoids from Trigonostemon chinensis: Structures, NO inhibitory activities, and interactions with iNOS.

    PubMed

    Xu, Jing; Peng, Maoqin; Sun, Xiaocong; Liu, Xingyu; Tong, Ling; Su, Guochen; Ohizumi, Yasushi; Lee, Dongho; Guo, Yuanqiang

    2016-10-01

    A phytochemical investigation to obtain new NO inhibitors led to the isolation of two new (1 and 2) and four known (3-6) diterpenoids from Trigonostemon chinensis. Their structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analyses, and the absolute configurations of new compounds were established by experimental and calculated ECD spectra. The inhibitory activities on lipopolysaccharide-induced NO production in murine microglial BV-2 cells of these diterpenoids were evaluated, and all of the compounds showed inhibitory effects. The interactions of bioactive compounds with iNOS protein were also studied by molecular docking. PMID:27570243

  9. New clerodane diterpenoids from the twigs and leaves of Croton euryphyllus.

    PubMed

    Pan, Zhenghong; Ning, Desheng; Wu, Xingde; Huang, Sisi; Li, Dianpeng; Lv, Shihong

    2015-03-15

    Three new nor-clerodane diterpenoids, crotoeurins A-C (1-3), together with four known ones were isolated from the twigs and leaves of Croton euryphyllus. Among them, crotoeurin A (1) is a new nor-clerodane diterpenoid dimer with a unique cyclobutane ring via a [2+2] cycloaddition. Their structures were elucidated by spectroscopic analyses and the stereochemistry of 1 was confirmed by single-crystal X-ray diffraction analysis. Compounds 1-3 exhibited neurite outgrowth-promoting activity on NGF-mediated PC12 cells at concentration of 10μM.

  10. Eutypenoids A–C: Novel Pimarane Diterpenoids from the Arctic Fungus Eutypella sp. D-1

    PubMed Central

    Zhang, Liu-Qiang; Chen, Xiao-Chong; Chen, Zhao-Qiang; Wang, Gui-Min; Zhu, Shi-Guo; Yang, Yi-Fu; Chen, Kai-Xian; Liu, Xiao-Yu; Li, Yi-Ming

    2016-01-01

    Eutypenoids A–C (1–3), pimarane diterpenoid alkaloid and two ring A rearranged pimarane diterpenoids, were isolated from the culture of Eutypella sp. D-1 obtained from high-latitude soil of the Arctic. Their structures, including absolute configurations, were authenticated on the basis of the mass spectroscopy (MS), nuclear magnetic resonance (NMR), X-ray crystallography, and electronic circular dichroism (ECD) analysis. The immunosuppressive effects of eutypenoids A–C (1–3) were studied using a ConA-induced splenocyte proliferation model, which suggested that 2 exhibited potent immunosuppressive activities. PMID:26959036

  11. Characterization of diterpenoids from Caesalpinia decapetala and their anti-TMV activities.

    PubMed

    Xu, Jing; Cao, Xiangrong; Liu, Feng; Ma, Jun; Liu, Xingyu; Tong, Ling; Su, Guochen; Ohizumi, Yasushi; Lee, Dongho; Wang, Lizhong; Guo, Yuanqiang

    2016-09-01

    Caesalpinia decapetala is a versatile medicinal plant belonging to the Fabaceae plant family. In our survey on plant secondary metabolites to obtain bioactive substances for the development of new agricultural anti-TMV agents, the chemical constituents of C. decapetala were investigated. This investigation led to the isolation of three new and ten known diterpenoids. Their structures including absolute configurations were elucidated based on the extensive NMR spectroscopic data analyses and the time-dependent density functional theory calculations. The following biological screenings revealed that most of these diterpenoids possessed anti-TMV activities. PMID:27491755

  12. New diterpenoids with estrogen sulfotransferase inhibitory activity from Leonurus sibiricus L.

    PubMed

    Narukawa, Yuji; Niimura, Akiko; Noguchi, Hitomi; Tamura, Hiroomi; Kiuchi, Fumiyuki

    2014-01-01

    Four new diterpenoids (1-4), along with eight known diterpenoids (5-12) were isolated from the acetone extract of Leonurus herb (aerial parts of Leonurus sibiricus L.). The structures of the compounds were determined by spectroscopic methods. Among the isolated compounds, compounds 2, 3, 8, 9 and 10 showed inhibitory activity against human liver cytosol estrogen sulfotransferase (E-ST), which plays a key role in the maintenance of cellular estrogen levels. Compound 2 showed the strongest activity with an IC50 value of 7.9 μM, which is comparable to the activity of the positive control, meclofenamic acid (IC50 5.4 μM).

  13. Phytotoxic cis-clerodane diterpenoids from the Chinese liverwort Scapania stephanii.

    PubMed

    Li, Rui-Juan; Sun, Yi; Sun, Bin; Wang, Xiao-Ning; Liu, Shan-Shan; Zhou, Jin-Chuan; Ye, Jian-Ping; Zhao, Yu; Liu, Lei; Lee, Kuo-Hsiung; Lou, Hong-Xiang

    2014-09-01

    Five cis-clerodane diterpenoids, stephanialides A-E, along with seven known cis-clerodanes, scaparvins A-C, parvitexins B and C, 3-chloro-4-hydroxy-parvitexin A, and scapanialide B, were isolated from the Chinese liverwort Scapania stephanii. Their structures were established unequivocally on the basis of spectroscopic data. The absolute configuration of stephanialide A was determined by analysis of CD data using the octant rule. Phytotoxic activity evaluation showed that this type of diterpenoids can significantly inhibit root elongation of the seeds of Arabidopsis thaliana, Lepidium sativum and Brassica pekinensis.

  14. Cytotoxic C20 Diterpenoid Alkaloids from the Australian Endemic Rainforest Plant Anopterus macleayanus.

    PubMed

    Levrier, Claire; Sadowski, Martin C; Nelson, Colleen C; Davis, Rohan A

    2015-12-24

    In order to identify new anticancer compounds from nature, a prefractionated library derived from Australian endemic plants was generated and screened against the prostate cancer cell line LNCaP using a metabolic assay. Fractions from the seeds, leaves, and wood of Anopterus macleayanus showed cytotoxic activity and were subsequently investigated using a combination of bioassay-guided fractionation and mass-directed isolation. This led to the identification of four new diterpenoid alkaloids, 6α-acetoxyanopterine (1), 4'-hydroxy-6α-acetoxyanopterine (2), 4'-hydroxyanopterine (3), and 11α-benzoylanopterine (4), along with four known compounds, anopterine (5), 7β-hydroxyanopterine (6), 7β,4'-dihydroxyanopterine (7), and 7β-hydroxy-11α-benzoylanopterine (8); all compounds were purified as their trifluoroacetate salt. The chemical structures of 1-8 were elucidated after analysis of 1D/2D NMR and MS data. Compounds 1-8 were evaluated for cytotoxic activity against a panel of human prostate cancer cells (LNCaP, C4-2B, and DuCaP) and nonmalignant cell lines (BPH-1 and WPMY-1), using a live-cell imaging system and a metabolic assay. All compounds showed potent cytotoxicity with IC50 values of <400 nM; compound 1 was the most active natural product from this series, with an IC50 value of 3.1 nM toward the LNCaP cell line. The live-cell imaging assay on 1-8 showed a concentration- and time-dependent effect on the cell morphology and proliferation of LNCaP cells.

  15. Functional characterization of wheat copalyl diphosphate synthases sheds light on the early evolution of labdane-related diterpenoid metabolism in the cereals.

    PubMed

    Wu, Yisheng; Zhou, Ke; Toyomasu, Tomonobu; Sugawara, Chizu; Oku, Madoka; Abe, Shiho; Usui, Masami; Mitsuhashi, Wataru; Chono, Makiko; Chandler, Peter M; Peters, Reuben J

    2012-12-01

    Two of the most agriculturally important cereal crop plants are wheat (Triticum aestivum) and rice (Oryza sativa). Rice has been shown to produce a number of diterpenoid natural products as phytoalexins and/or allelochemicals--specifically, labdane-related diterpenoids, whose biosynthesis proceeds via formation of an eponymous labdadienyl/copalyl diphosphate (CPP) intermediate (e.g., the ent-CPP of gibberellin phytohormone biosynthesis). Similar to rice, wheat encodes a number of CPP synthases (CPS), and the three CPS characterized to date (TaCPS1-3) all have been suggested to produce ent-CPP. However, several of the downstream diterpene synthases will only react with CPP intermediate of normal or syn, but not ent, stereochemistry, as described in the accompanying report. Investigation of additional CPS did not resolve this issue, as the only other functional synthase (TaCPS4) also produced ent-CPP. Chiral product characterization of all the TaCPS then established that TaCPS2 uniquely produces normal, rather than ent-, CPP, thus, providing a suitable substrate source for the downstream diterpene synthases. Notably, TaCPS2 is most homologous to the similarly stereochemically differentiated syn-CPP synthase from rice (OsCPS4), while the non-inducible TaCPS3 and TaCPS4 cluster with the rice OsCPS1 required for gibberellin phytohormone biosynthesis, as well as with a barley (Hordeum vulgare) CPS (HvCPS1) that also is characterized here as similarly producing ent-CPP. These results suggest that diversification of labdane-related diterpenoid metabolism beyond the ancestral gibberellins occurred early in cereal evolution, and included the type of stereochemical variation demonstrated here.

  16. Functional characterization of wheat copalyl diphosphate synthases sheds light on the early evolution of labdane-related diterpenoid metabolism in the cereals

    PubMed Central

    Wu, Yisheng; Zhou, Ke; Toyomasu, Tomonobu; Sugawara, Chizu; Oku, Madoka; Abe, Shiho; Usui, Masami; Mitsuhashi, Wataru; Chono, Makiko; Chandler, Peter M.; Peters, Reuben J.

    2012-01-01

    Two of the most agriculturally important cereal crop plants are wheat (Triticum aestivum) and rice (Oryza sativa). Rice has been shown to produce a number of diterpenoid natural products as phytoalexins and/or allelochemicals – specifically, labdane-related diterpenoids, whose biosynthesis proceeds via formation of an eponymous labdadienyl/copalyl diphosphate (CPP) intermediate (e.g., the ent-CPP of gibberellin phytohormone biosynthesis). Similar to rice, wheat encodes a number of CPP synthases (CPS), and the three CPS characterized to date (TaCPS1,2,&3) all have been suggested to produce ent-CPP. However, several of the downstream diterpene synthases will only react with CPP intermediate of normal or syn, but not ent, stereochemistry, as described in the accompanying report. Investigation of additional CPS did not resolve this issue, as the only other functional synthase (TaCPS4) also produced ent-CPP. Chiral product characterization of all the TaCPS then revealed that TaCPS2 uniquely produces normal, rather than ent-, CPP; thus, providing a suitable substrate source for the downstream diterpene synthases. Notably, TaCPS2 is most homologous to the similarly stereochemically differentiated syn-CPP synthase from rice (OsCPS4), while the non-inducible TaCPS3 and TaCPS4 cluster with the rice OsCPS1 required for gibberellin phytohormone biosynthesis, as well as with a barley (Hordeum vulgare) CPS (HvCPS1) that also is characterized here as similarly producing ent-CPP. These results suggest that diversification of labdane-related diterpenoid metabolism beyond the ancestral gibberellins occurred early in cereal evolution, and included the type of stereochemical variation demonstrated here. PMID:23009878

  17. (+)-Podocarpic Acid as Chiral Template in the Synthesis of Aphidicolane, Stemodane and Stemarane Diterpenoids †.

    PubMed

    La Bella, Angela; Leonelli, Francesca; Migneco, Luisa Maria; Marini Bettolo, Rinaldo

    2016-01-01

    In this review the synthetic work in the field of aphidicolane, stemodane and stemarane diterpenoids, in which readily available (+)-podocarpic acid (4) was used as chiral template for the construction of their polycyclic structures, is described as it developed along the years. In the frame of this work (+)-podocarpic acid (4) was a very useful tool in a model study leading to the syntheses of tetracyclic ketones 7 and 8, models of key intermediates 5a and 6 in the syntheses of (+)-aphidicolin (1) and (+)-stemodin (2a), respectively. (+)-Podocarpic acid (4) was also converted into (+)-2-deoxystemodinone (2d), allowing confirmation of the stemodane diterpenoids absolute configuration, into (+)-aphidicol-15-ene (36) and into Stemodia chilensis tetracyclic diterpenoid (+)-19-acetoxystemodan-12-ol (2f), allowing confirmation of its structure. (+)-Podocarpic acid (4) was then extensively used in the work which led to the synthesis of (+)-stemar-13-ene (57) and (+)-18-deoxystemarin (3b). Finally, (+)-4 was converted into (+)-2-deoxyoryzalexin S (66), which made it possible to demonstrate that the structure of (+)-66 could not be attributed to a Chilean Calceolaria isolated diterpenoid to which this structure had been assigned. PMID:27617995

  18. In vitro antituberculosis activity of diterpenoids from the Vietnamese medicinal plant Croton tonkinensis.

    PubMed

    Jang, Woong Sik; Jyoti, Md Anirban; Kim, Sukyung; Nam, Kung-Woo; Ha, Thi Kim Quy; Oh, Won Keun; Song, Ho-Yeon

    2016-01-01

    Diterpenoids from the Vietnamese medicinal plant Croton tonkinensis are rich in ent-kaurane, kaurane and the grayanane class and are valuable intermediate plant metabolites with different bioactivities. In this study, we report the antituberculosis activity of these diterpenoids against both susceptible and resistant strains of M. tuberculosis for the first time. All of the ent-kaurane, kaurane and grayanane diterpenoids showed high to moderate activity against Mycobacterium. The highest antituberculosis activity was observed for ent-1β,7α,14β-triacetoxykaur-16-en-15-one (cpp604), with MIC values of 0.78, 1.56 and 3.12-12.5 µg/ml against H37Ra, H37Rv and all other resistant strains of Mycobacterium tuberculosis examined. In addition, other ent-kaurane-type diterpenoids also showed very high activities against mycobacterium, including cpp609 (1.56 µg/ml), cpp610 (1.56 µg/ml), cpp601 (3.12-6.25 µg/ml), cpp602 (3.12-6.25 µg/ml), cpp607 (3.12-6.25 µg/ml) and cpp608 (3.12-6.25 µg/ml). From the structure-activity relationship, functional groups R3 and R5 of the ent-kaurane skeleton were found to modulate the antimycobacterial activity.

  19. Polyacetylated labdane-type diterpenoids, ptychantins P-R from Chinese liverwort Ptychanthus striatus.

    PubMed

    Wu, Jing-Yi; Zhang, Jiao-Zhen; Kang, Ya-Qi; Wang, Xiao; Fan, Pei-Hong; Zhou, Jin-Chuan; Lou, Hong-Xiang

    2015-05-01

    Three new polyacetylated labdane diterpenoids ptychantins P-R (1-3) and four known compounds (4-7) were isolated from an EtOH extract of the Chinese liverwort Ptychanthus striatus (Lehm. & Lindenb.) Nees. Their structures were established by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D NMR, and 2D NMR). PMID:25677361

  20. Cembrane-type diterpenoids from the Chinese liverworts Chandonanthus hirtellus and C. birmensis.

    PubMed

    Li, Rui-Juan; Lin, Zhao-Min; Kang, Ya-Qi; Guo, Yan-Xia; Lv, Xin; Zhou, Jin-Chuan; Wang, Song; Lou, Hong-Xiang

    2014-02-28

    Six new cembrane-type diterpenoids (1-6) were isolated from two species of Chandonanthus: Chandonanones A, B, and D-F (1, 2, and 4-6) were isolated from C. hirtellus, and chandonanones B, C, E, and F (2, 3, 5, and 6) from C. birmensis. Five known diterpenoids, (8E)-4α-acetoxy-12α,13α-epoxycembra-1(15),8-diene (7), isochandonanthone (8), chandonanthone (9), anadensin (10), and 2,10,14-triacetoxy-7,8,18,19-diepoxydolabell-3(E)-ene (11), were also obtained. The structures of the new metabolites were established by analyses of their spectroscopic data (1D NMR, 2D NMR, HRESIMS, and IR). The absolute configurations of compounds 1 and 2 were unequivocally confirmed using single-crystal X-ray diffraction analysis with Cu Kα radiation. Cytotoxicity tests of the isolated diterpenoids against seven cancer cell lines (DU145, PC3, A549, PC12, NCI-H292, NCI-H1299, and A172) revealed that some of the diterpenoids had weak activity.

  1. A new diterpenoid from the south China sea soft coral Lobophytum sp.

    PubMed

    Chen, Si-Han; Huang, Hui; Guo, Yue-Wei

    2008-01-01

    A new cembrane-type diterpene, 11,12-epoxy-sarcophytoxide (1), along with five related diterpenoids (2, and 4-7), has been isolated from the soft coral Lobophytum sp. The structure of the new compound 1 was elucidated on the basis of detailed analysis of its spectroscopic data, and by comparing its NMR spectral data with those of the model compounds.

  2. Comparative Transcriptomics Unravel Biochemical Specialization of Leaf Tissues of Stevia for Diterpenoid Production.

    PubMed

    Kim, Mi Jung; Jin, Jingjing; Zheng, Junshi; Wong, Limsoon; Chua, Nam-Hai; Jang, In-Cheol

    2015-12-01

    Stevia (Stevia rebaudiana) produces not only a group of diterpenoid glycosides known as steviol glycosides (SGs), but also other labdane-type diterpenoids that may be spatially separated from SGs. However, their biosynthetic routes and spatial distribution in leaf tissues have not yet been elucidated. Here, we integrate metabolome and transcriptome analyses of Stevia to explore the biosynthetic capacity of leaf tissues for diterpenoid metabolism. Tissue-specific chemical analyses confirmed that SGs were accumulated in leaf cells but not in trichomes. On the other hand, Stevia leaf trichomes stored other labdane-type diterpenoids such as oxomanoyl oxide and agatholic acid. RNA sequencing analyses from two different tissues of Stevia provided a comprehensive overview of dynamic metabolic activities in trichomes and leaf without trichomes. These metabolite-guided transcriptomics and phylogenetic and gene expression analyses clearly identified specific gene members encoding enzymes involved in the 2-C-methyl-d-erythritol 4-phosphate pathway and the biosynthesis of steviol or other labdane-type diterpenoids. Additionally, our RNA sequencing analysis uncovered copalyl diphosphate synthase (SrCPS) and kaurene synthase1 (SrKS1) homologs, SrCPS2 and KS-like (SrKSL), which were specifically expressed in trichomes. In vitro and in planta assays showed that unlike SrCPS and SrKS1, SrCPS2 synthesized labda-13-en-8-ol diphosphate and successively catalyzed the formation of manoyl oxide and epi-manoyl oxide in combination with SrKSL. Our findings suggest that Stevia may have evolved to use distinct metabolic pathways to avoid metabolic interferences in leaf tissues for efficient production of diverse secondary metabolites. PMID:26438788

  3. A new mulinane diterpenoid from the cushion shrub Azorella compacta growing in Perú

    PubMed Central

    Salgado, Francisco; Areche, Carlos; Sepúlveda, Beatriz; Simirgiotis, Mario J.; Cáceres, Fátima; Quispe, Cristina; Quispe, Lina; Cano, Teresa

    2014-01-01

    Background: Azorella compacta is a rare yellow-green compact resinous cushion shrub growing from the high Andes of southern Perú to northwestern Argentina, and which is a producer of biologically active and unique diterpenoids. Objective: This study investigated the secondary metabolites present in a Peruvian sample of Azorella compacta and the evaluation of gastroprotective activity of the isolated compounds in a gastric- induced ulcer model in mice. Material and Methods: Six secondary metabolites (diterpenoids 1-6) present in the dichloromethane (DCM) extract of A. compacta growing in Perú were isolated by a combination of Sephadex LH-20 permeation and silica gel chromatography and their chemical structures were elucidated by spectroscopic methods (NMR) and molecular modeling. The gastroprotective activity of the new compound 1 was evaluated on the HCl/EtOH-induced gastric lesion model in mice and compared to the activity showed by the known compounds. Results: A new mulinane diterpene along with five known diterpenoids have been isolated from a Peruvian sample of A. compacta and the gastroprotective results show that compound 1 is less active than the other known mulinane diterpenoids isolated. Conclusions: A. compacta growing in Perú showed the presence of the new mulinane 1, which was poorly active in the HCl/EtOH-induced gastric lesion model in mice. Indeed, the activity was lower than other diterpenoids (2-6) showing an oxygenated function at C-16 or/and C-20, which confirm the role of an oxygenated group (OH or carboxylic acid) for the gastroprotective activity of mulinane compounds. PMID:25298672

  4. Comparative Transcriptomics Unravel Biochemical Specialization of Leaf Tissues of Stevia for Diterpenoid Production.

    PubMed

    Kim, Mi Jung; Jin, Jingjing; Zheng, Junshi; Wong, Limsoon; Chua, Nam-Hai; Jang, In-Cheol

    2015-12-01

    Stevia (Stevia rebaudiana) produces not only a group of diterpenoid glycosides known as steviol glycosides (SGs), but also other labdane-type diterpenoids that may be spatially separated from SGs. However, their biosynthetic routes and spatial distribution in leaf tissues have not yet been elucidated. Here, we integrate metabolome and transcriptome analyses of Stevia to explore the biosynthetic capacity of leaf tissues for diterpenoid metabolism. Tissue-specific chemical analyses confirmed that SGs were accumulated in leaf cells but not in trichomes. On the other hand, Stevia leaf trichomes stored other labdane-type diterpenoids such as oxomanoyl oxide and agatholic acid. RNA sequencing analyses from two different tissues of Stevia provided a comprehensive overview of dynamic metabolic activities in trichomes and leaf without trichomes. These metabolite-guided transcriptomics and phylogenetic and gene expression analyses clearly identified specific gene members encoding enzymes involved in the 2-C-methyl-d-erythritol 4-phosphate pathway and the biosynthesis of steviol or other labdane-type diterpenoids. Additionally, our RNA sequencing analysis uncovered copalyl diphosphate synthase (SrCPS) and kaurene synthase1 (SrKS1) homologs, SrCPS2 and KS-like (SrKSL), which were specifically expressed in trichomes. In vitro and in planta assays showed that unlike SrCPS and SrKS1, SrCPS2 synthesized labda-13-en-8-ol diphosphate and successively catalyzed the formation of manoyl oxide and epi-manoyl oxide in combination with SrKSL. Our findings suggest that Stevia may have evolved to use distinct metabolic pathways to avoid metabolic interferences in leaf tissues for efficient production of diverse secondary metabolites.

  5. Jaridonin, a novel ent-kaurene diterpenoid from Isodon rubescens, inducing apoptosis via production of reactive oxygen species in esophageal cancer cells.

    PubMed

    Ma, Yong-Cheng; Ke, Yu; Zi, Xiaolin; Zhao, Wen; Shi, Xiao-Jing; Liu, Hong-Min

    2013-07-01

    Isodon rubescens, a Chinese herb, has been used as a folk, botanical medicine in China for inflammatory diseases and cancer treatment for many years. Recently, we isolated a new ent-kaurene diterpenoid, named Jaridonin, from Isodon rubescens. The chemical structure of Jaridonin was verified by infrared (IR), nuclear magnetic resonance (NMR), and mass spectrum (MS) data as well as X-ray spectra. Jaridonin potently reduced viabilities of several esophageal cancer cell lines, including EC109, EC9706 and EC1. Jaridonin treatment resulted in typical apoptotic morphological characteristics, increased the number of annexin V-positive staining cells, as well as caused a G2/M arrest in cell cycle progression. Furthermore, Jaridonin resulted in a significant loss of mitochondrial membrane potential, release of cytochrome c into the cytosol, and then activation of Caspase-9 and -3, leading to activation of the mitochondria mediated apoptosis. Furthermore, these effects of Jaridonin were accompanied by marked reactive oxygen species (ROS) production and increased expression of p53, p21(waf1/Cip1) and Bax, whereas two ROS scavengers, N-acetyl-L-cysteine (LNAC) and Vitamin C, significantly attenuated the effects of Jaridonin on the mitochondrial membrane potential, DNA damage, expression of p53 and p21(waf1/Cip1) and reduction of cell viabilities. Taken together, our results suggest that a natural ent-kaurenoid diterpenoid, Jaridonin, is a novel apoptosis inducer and deserves further investigation as a new chemotherapeutic strategy for patients with esophageal cancer. PMID:23597192

  6. New clerodane diterpenoid glycosides from the aerial parts of Nannoglottis carpesioides.

    PubMed

    Meng, Xian-Hua; Zou, Chuan-Zong; Jin, Xiao-Jie; Huang, Guo-Du; Yang, Yong-Jin; Zou, Xi-Ying; Yao, Xiao-Jun; Zhu, Ying

    2014-03-01

    Three new clerodane diterpenoid glycosides with L-arabinose (1-3), together with ten known compounds including phytol-type diterpenes, cycloartane-type, ursane-type, and oleanane-type triterpenes, were isolated from the aerial parts of Nannoglottis carpesioides which a Chinese endemic genus. The structures of the new compounds 1-3 were identified based on chemical and spectroscopic studies, including one- and two-dimensional NMR, HRESIMS, UV, and IR results. Their absolute configurations were determined by the application of theory calculations of optical rotation, which were compared with the experimental data. New aglycone 1a and L-arabinose were obtained by acid hydrolysis of 1 and GC-MS analysis. The cytotoxicities of some isolated compounds against a panel of human cancer cell lines were evaluated by the MTT assay. Clerodane diterpenoides are the characteristic chemical constituents and may be used as chemical markers of the genus Nannoglottis.

  7. Diterpenoids from the roots of Croton crassifolius and their anti-angiogenic activity.

    PubMed

    Wang, Jia-Jian; Chung, Hau Yin; Zhang, Yu-Bo; Li, Guo-Qiang; Li, Yao-Lan; Huang, Wei-Huan; Wang, Guo-Cai

    2016-02-01

    Six diterpenoids [crassifolin J, K, L, M, N and O] along with eleven known ones were isolated from the supercritical fluid extract (SFE) of the roots of Croton crassifolius (Euphorbiaceae). Their structures were elucidated using spectroscopic methods (IR, UV, HRESIMS, 1D and 2D NMR). The structure and stereochemistry of crassifolin J was confirmed by single-crystal X-ray diffraction analysis, and the absolute configurations of crassifolin K-M were determined by CD spectra. Twenty-three diterpenoids from this plant were screened for their anti-angiogenic activity using a wild-type zebrafish in vivo model. Four of the known compounds were active, of which penduliflaworosin possessed the best activity relative to the positive control (SU5416). Further study demonstrated that penduliflaworosin could inhibit vessel formation on Tg(fli1a:EGFP)y1-type zebrafish embryos.

  8. Two new eunicellin diterpenoids from the South China Sea gorgonian Muricella sibogae and their bioactivities.

    PubMed

    Zhang, Xing-Wang; Tang, Xu-Li; Yuan, Hong-Rui; Feng, Dan-Qing; Su, Pei; Li, Ping-Lin; Li, Guo-Qiang

    2015-01-01

    A systematic re-study on gorgonian Muricella sibogae from South China Sea yielded 10 eunicellin-based diterpenoids including two new ones, sibogins C and D (1 and 2). Their structures were elucidated by extensive spectroscopic analyses (1D and 2D NMR, IR and MS) and by comparison with data reported in literatures. All the isolates were tested for cytotoxic and antifouling activities. Compounds 3 and 5 showed significant antifouling activity against the green mussel Perna viridis, and especially 3 was suggested as a potent low-toxic antifouling agent with a large LC50/EC50 value of 18.6. This was the first report on the antifouling activity of the eunicellin-type diterpenoids against the green mussel.

  9. Flexibilins A–C, New Cembrane-Type Diterpenoids from the Formosan Soft Coral, Sinularia flexibilis

    PubMed Central

    Hu, Li-Chung; Su, Jui-Hsin; Chiang, Michael Yen-Nan; Lu, Mei-Chin; Hwang, Tsong-Long; Chen, Yung-Husan; Hu, Wan-Ping; Lin, Nai-Cheng; Wang, Wei-Hsien; Fang, Lee-Shing; Kuo, Yueh-Hsiung; Sung, Ping-Jyun

    2013-01-01

    Three new cembrane-type diterpenoids, flexibilins A–C (1–3), along with a known cembrane, (−)-sandensolide (4), were isolated from the soft coral, Sinularia flexibilis. The structures of cembranes 1–4 were elucidated by spectroscopic methods. The structure of 4, including its absolute stereochemistry, was further confirmed by single-crystal X-ray diffraction analysis. Cembrane 2 displayed a moderate inhibitory effect on the release of elastase by human neutrophils. PMID:23752355

  10. New labdane diterpenoids from Croton laui and their anti-inflammatory activities.

    PubMed

    Yang, Li; Zhang, Yu-Bo; Chen, Li-Feng; Chen, Neng-Hua; Wu, Zhong-Nan; Jiang, Si-Qi; Jiang, Lin; Li, Guo-Qiang; Li, Yao-Lan; Wang, Guo-Cai

    2016-10-01

    Nine new labdane diterpenoids (1-9) were isolated from the aerial parts of Croton laui, along with eight known analogues (10-17). Their structures were identified on the basis of the spectral data (IR, UV, HRESIMS, 1D and 2D NMR), and the structure of 8 was confirmed by single crystal X-ray diffraction analyses. In addition, compounds 1, 4, 7, 8, and 14 showed weak anti-inflammatory activities in LPS-stimulated RAW 264.7 cells.

  11. ent-Atisane and ent-kaurane diterpenoids from Isodon rosthornii.

    PubMed

    Zhan, Rui; Li, Xiao-Nian; Du, Xue; Wang, Wei-Guang; Dong, Ke; Su, Jia; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong

    2013-07-01

    A new ent-atisanoid (1) and three new ent-kauranoids (2-4) belonging to different types, along with four known compounds were isolated from Isodon rosthornii. Their structures were established by means of extensive spectroscopic analysis. The absolute configuration of 1 was further determined by X-ray diffraction. Compounds 1 and 5 are the first example of atisane-type diterpenoid from this plant. PMID:23660245

  12. Briarenolides K and L, New Anti-Inflammatory Briarane Diterpenoids from an Octocoral Briareum sp. (Briareidae)

    PubMed Central

    Su, Yin-Di; Su, Tzu-Rong; Wen, Zhi-Hong; Hwang, Tsong-Long; Fang, Lee-Shing; Chen, Jih-Jung; Wu, Yang-Chang; Sheu, Jyh-Horng; Sung, Ping-Jyun

    2015-01-01

    Two new briarane-type diterpenoids, briarenolides K (1) and L (2), were isolated from an octocoral identified as Briareum sp. The structures of new briaranes 1 and 2 were elucidated by spectroscopic methods. In the in vitro anti-inflammatory effects test, briaranes 1 and 2 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. PMID:25689566

  13. New casbane diterpenoids from a South China Sea soft coral, Sinularia sp.

    PubMed

    Yin, Jian; Zhao, Min; Ma, Minshan; Xu, Yuping; Xiang, Zheng; Cai, Yuepiao; Dong, Jianyong; Lei, Xinxiang; Huang, Kexin; Yan, Pengcheng

    2013-02-01

    Six new casbane diterpenoids, named as sinularcasbanes A-F (1-6), along with six known analogues 7-12, were isolated from a South China Sea soft coral, Sinularia sp. The structures of the new compounds were elucidated by extensive spectroscopic analysis and by comparison with data reported in the literature. All compounds were evaluated for their cytotoxicity against selected cancer cell lines and the inhibition of lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse peritoneal macrophages.

  14. A new briarane-type diterpenoid from the South China Sea Gorgonian Dichotella gemmacea.

    PubMed

    Sun, Jian-Fan; Yang, Bin; Zhou, Xue-Feng; Yang, Xian-Wen; Wang, Lishu; Liu, Yonghong

    2015-01-01

    One new briarane-type diterpenoid, dichotellide V (1), along with four known analogues, gemmacolide N (2), dichotellide J (3), junceelin A (4) and junceellolide A (5), was isolated from the South China Sea gorgonian Dichotella gemmacea. All of the isolated compounds (1-5) were established by comprehensive analysis of the spectral data, especially 1D and 2D NMR (HMQC and HMBC) spectra. The cytotoxic activities of these compounds were evaluated.

  15. Enzymes for synthetic biology of ambroxide-related diterpenoid fragrance compounds.

    PubMed

    Zerbe, Philipp; Bohlmann, Jörg

    2015-01-01

    Ambrox and related ambroxides are highly priced in the fragrance industry, and valued for their delicate odor and fixative properties. Historically, ambrox was obtained from ambergris, a waxy excretion produced by sperm whales, now an endangered species. Synthetic ambroxides have replaced ambergris in perfume manufacture. Plant labdane diterpenoids can serve as starting material for ambroxide synthesis. Among these, the diterpene alcohol sclareol is the major industrial precursor obtained from cultivated clary sage (Salvia sclarea). In plants, a large family of diterpene synthase (diTPS) enzymes controls key reactions in diterpenoid biosynthesis. Advanced metabolite profiling and high-throughput sequencing of fragrant and medicinal plants have accelerated discovery of novel diTPS functions, providing a resource for combinatorial synthetic biology and metabolic engineering approaches. This chapter highlights recent progress on the discovery, characterization, and engineering of plant diTPSs with potential uses in ambroxide production. It features biosynthesis of sclareol, cis-abienol, and diterpene resin acids, as sources of genes and enzymes for diterpenoid bioproducts.

  16. Enzymes for synthetic biology of ambroxide-related diterpenoid fragrance compounds.

    PubMed

    Zerbe, Philipp; Bohlmann, Jörg

    2015-01-01

    Ambrox and related ambroxides are highly priced in the fragrance industry, and valued for their delicate odor and fixative properties. Historically, ambrox was obtained from ambergris, a waxy excretion produced by sperm whales, now an endangered species. Synthetic ambroxides have replaced ambergris in perfume manufacture. Plant labdane diterpenoids can serve as starting material for ambroxide synthesis. Among these, the diterpene alcohol sclareol is the major industrial precursor obtained from cultivated clary sage (Salvia sclarea). In plants, a large family of diterpene synthase (diTPS) enzymes controls key reactions in diterpenoid biosynthesis. Advanced metabolite profiling and high-throughput sequencing of fragrant and medicinal plants have accelerated discovery of novel diTPS functions, providing a resource for combinatorial synthetic biology and metabolic engineering approaches. This chapter highlights recent progress on the discovery, characterization, and engineering of plant diTPSs with potential uses in ambroxide production. It features biosynthesis of sclareol, cis-abienol, and diterpene resin acids, as sources of genes and enzymes for diterpenoid bioproducts. PMID:25846965

  17. In vitro anti-inflammatory effects of diterpenoids and sesquiterpenoids from traditional Chinese medicine Siegesbeckia pubescens.

    PubMed

    Wang, Rui; Liu, Ying-Qian; Ha, Wei; Shi, Yan-Ping; Hwang, Tsong-Long; Huang, Guan-Jhong; Wu, Tian-Shung; Lee, Kuo-Hsiung

    2014-08-15

    Oxidative stress imposed by reactive oxygen species plays a crucial role in pathophysiology of inflammatory diseases. In the present study, sesquiterpenoids and diterpenoids isolated from Siegesbeckia pubescens, a Chinese traditional medicine used to treat arthritis, were evaluated for inhibition of NO production in activated RAW 264.7 macrophages and FMLP/CB induced O2(·-) generation and elastase release in human neutrophils. In the former assay, sesquiterpenoids were more potent than diterpenoids. The C-4 carbonyl group in the carabrane-type sesquiterpenoid 3 and the C-9 ether linkage in the germacrane sesquiterpene 7 were associated with the enhanced potency. Also, for the active ent-kaurane type diterpenoids, esterification of 17-OH with isobutyric acid and acetylation of 18-OH affected the inhibition of O2(·-) generation and elastase release. This report is the first to describe the inhibitory effects on oxidative stress of secondary metabolites from S. pubescens. Its findings suggest that active terpenoids from the herb could be used as lead anti-inflammatory agents.

  18. Diterpenoid phytoalexin factor, a bHLH transcription factor, plays a central role in the biosynthesis of diterpenoid phytoalexins in rice.

    PubMed

    Yamamura, Chihiro; Mizutani, Emi; Okada, Kazunori; Nakagawa, Hitoshi; Fukushima, Setsuko; Tanaka, Atsunori; Maeda, Satoru; Kamakura, Takashi; Yamane, Hisakazu; Takatsuji, Hiroshi; Mori, Masaki

    2015-12-01

    Rice (Oryza sativa) produces diterpenoid phytoalexins (DPs), momilactones and phytocassanes as major phytoalexins. Accumulation of DPs is induced in rice by blast fungus infection, copper chloride or UV light. Here, we describe a rice transcription factor named diterpenoid phytoalexin factor (DPF), which is a basic helix-loop-helix (bHLH) transcription factor. The gene encoding DPF is expressed mainly in roots and panicles, and is inducible in leaves by blast infection, copper chloride or UV. Expression of all DP biosynthetic genes and accumulation of momilactones and phytocassanes were remarkably increased and decreased in DPF over-expressing and DPF knockdown rice, respectively. These results clearly demonstrated that DPF positively regulates DP accumulation via transcriptional regulation of DP biosynthetic genes, and plays a central role in the biosynthesis of DPs in rice. Furthermore, DPF activated the promoters of COPALYL DIPHOSPHATE SYNTHASE2 (CPS2) and CYTOCHROME P450 MONOOXYGENASE 99A2 (CYP99A2), whose products are implicated in the biosynthesis of phytocassanes and momilactones, respectively. Mutations in the N-boxes in the CPS2 upstream region, to which several animal bHLH transcription factors bind, decreased CPS2 transcription, indicating that DPF positively regulates CPS2 transcription through the N-boxes. In addition, DPF partly regulates CYP99A2 through the N-box. This study demonstrates that DPF acts as a master transcription factor in DP biosynthesis.

  19. Diterpenoid phytoalexin factor, a bHLH transcription factor, plays a central role in the biosynthesis of diterpenoid phytoalexins in rice.

    PubMed

    Yamamura, Chihiro; Mizutani, Emi; Okada, Kazunori; Nakagawa, Hitoshi; Fukushima, Setsuko; Tanaka, Atsunori; Maeda, Satoru; Kamakura, Takashi; Yamane, Hisakazu; Takatsuji, Hiroshi; Mori, Masaki

    2015-12-01

    Rice (Oryza sativa) produces diterpenoid phytoalexins (DPs), momilactones and phytocassanes as major phytoalexins. Accumulation of DPs is induced in rice by blast fungus infection, copper chloride or UV light. Here, we describe a rice transcription factor named diterpenoid phytoalexin factor (DPF), which is a basic helix-loop-helix (bHLH) transcription factor. The gene encoding DPF is expressed mainly in roots and panicles, and is inducible in leaves by blast infection, copper chloride or UV. Expression of all DP biosynthetic genes and accumulation of momilactones and phytocassanes were remarkably increased and decreased in DPF over-expressing and DPF knockdown rice, respectively. These results clearly demonstrated that DPF positively regulates DP accumulation via transcriptional regulation of DP biosynthetic genes, and plays a central role in the biosynthesis of DPs in rice. Furthermore, DPF activated the promoters of COPALYL DIPHOSPHATE SYNTHASE2 (CPS2) and CYTOCHROME P450 MONOOXYGENASE 99A2 (CYP99A2), whose products are implicated in the biosynthesis of phytocassanes and momilactones, respectively. Mutations in the N-boxes in the CPS2 upstream region, to which several animal bHLH transcription factors bind, decreased CPS2 transcription, indicating that DPF positively regulates CPS2 transcription through the N-boxes. In addition, DPF partly regulates CYP99A2 through the N-box. This study demonstrates that DPF acts as a master transcription factor in DP biosynthesis. PMID:26506081

  20. Molecular structure and vibrational bands and 13C chemical shift assignments of both enmein-type diterpenoids by DFT study

    NASA Astrophysics Data System (ADS)

    Wang, Tao; Wu, Yi fang; Wang, Xue liang

    2014-01-01

    We report here theoretical and experimental studies on the molecular structure and vibrational and NMR spectra of both natural enmein type diterpenoids molecule (6, 7-seco-ent-kaurenes enmein type), isolated from the leaves of Isodon japonica (Burm.f.) Hara var. galaucocalyx (maxin) Hara. The optimized geometry, total energy, NMR chemical shifts and vibrational wavenumbers of epinodosinol and epinodosin have been determined using B3LYP method with 6-311G (d,p) basis set. A complete vibrational assignment is provided for the observed IR spectra of studied compounds. The calculated wavenumbers and 13C c.s. are in an excellent agreement with the experimental values. Quantum chemical calculations at the B3LYP/6-311G (d,p) level of theory have been carried out on studied compounds to obtain a set of molecular electronic properties (MEP,HOMO, LUMO and gap energies ΔEg). Electrostatic potential surfaces have been mapped over the electron density isosurfaces to obtain information about the size, shape, charge density distribution and chemical reactivity of the molecules.

  1. Molecular structure and vibrational bands and 13C chemical shift assignments of both enmein-type diterpenoids by DFT study.

    PubMed

    Wang, Tao; Wu, Yi fang; Wang, Xue liang

    2014-01-01

    We report here theoretical and experimental studies on the molecular structure and vibrational and NMR spectra of both natural enmein type diterpenoids molecule (6, 7-seco-ent-kaurenes enmein type), isolated from the leaves of Isodon japonica (Burm.f.) Hara var. galaucocalyx (maxin) Hara. The optimized geometry, total energy, NMR chemical shifts and vibrational wavenumbers of epinodosinol and epinodosin have been determined using B3LYP method with 6-311G (d,p) basis set. A complete vibrational assignment is provided for the observed IR spectra of studied compounds. The calculated wavenumbers and 13C c.s. are in an excellent agreement with the experimental values. Quantum chemical calculations at the B3LYP/6-311G (d,p) level of theory have been carried out on studied compounds to obtain a set of molecular electronic properties (MEP,HOMO, LUMO and gap energies ΔEg). Electrostatic potential surfaces have been mapped over the electron density isosurfaces to obtain information about the size, shape, charge density distribution and chemical reactivity of the molecules. PMID:24013676

  2. Studies on C20-Diterpenoid Alkaloids: Synthesis of the Hetidine Framework and Its Application to the Synthesis of Dihydronavirine and the Atisine Skeleton

    PubMed Central

    2015-01-01

    The full details of a synthesis of the hetidine framework of the C20-diterpenoid alkaloids and its conversion to the atisine core structure are reported. The application of the hetidine framework to the synthesis of dihydronavirine, which is the formal reduction product of the natural product navirine, is also described. Key to the success of these studies is the use of a Ga(III)-catalyzed cycloisomerization reaction of alkynylindenes to prepare a [6–7–6] framework that was advanced to the hetidine skeleton. Furthermore, a Michael/aldol sequence was developed for the construction of the bicyclo[2.2.2] framework that is characteristic of the hetidines and atisines. PMID:25004408

  3. Antimutagenic activity of a secoisopimarane diterpenoid from Salvia cinnabarina M. Martens et Galeotti in the bacterial reverse mutation assay.

    PubMed

    Di Sotto, A; Mastrangelo, S; Romussi, G; Bisio, A; Mazzanti, G

    2009-08-01

    The effects of 3,4-secoisopimar-4(18),7,15-trien-3-oic acid, a diterpenoid isolated from Salvia cinnabarina, were evaluated in the Ames test on Salmonella typhimurium TA98 and TA100 and on Escherichia coli WP2uvrA, in presence and in absence of the metabolic activation system. The secoisopimarane diterpenoid not only showed to be devoid of mutagenic activity, but significantly inhibited the effect of some known mutagens, in all strains tested. The reduction of the number of chemically-induced revertant colonies reached the value of 92.2% against 2-aminoanthracene, 59.6% against 2-nitrofluorene, 50.9% against sodium azide and 39.9% against methyl methane sulfonate. It is hypothesized that the secoisopimarane diterpenoid acts by aspecific mechanisms, by alterating the cell permeability thus blocking the mutagen adsorption across the bacterial membrane, or by chemical or enzymatic inhibition of the mutagens. PMID:19497346

  4. Hormonal diterpenoids derived from ent-kaurenoic acid are involved in the blue-light avoidance response of Physcomitrella patens.

    PubMed

    Miyazaki, Sho; Nakajima, Masatoshi; Kawaide, Hiroshi

    2015-01-01

    Gibberellins (GAs) are diterpenoid hormones that regulate growth and development in flowering plants. The moss Physcomitrella patens has part of the GA biosynthetic pathway from geranylgeranyl diphosphate to ent-kaurenoic acid via ent-kaurene, but it does not produce GA. Disruption of the ent-kaurene synthase gene in P. patens suppressed caulonemal differentiation. Application of ent-kaurene or ent-kaurenoic acid restored differentiation, suggesting that derivative(s) of ent-kaurenoic acid, but not GAs, are endogenous regulator(s) of caulonemal cell differentiation. The protonemal growth of P. patens shows an avoidance response under unilateral blue light. Physiological studies using gene mutants involved in ent-kaurene biosynthesis confirmed that diterpenoid(s) regulate the blue-light response. Here, we discuss the implications of these findings, and provide data for the ent-kaurene oxidase gene-disrupted mutant.

  5. New ent-Clerodane and Abietane Diterpenoids from the Roots of Kenyan Croton megalocarpoides Friis & M. G. Gilbert.

    PubMed

    Ndunda, Beth; Langat, Moses K; Mulholland, Dulcie A; Eastman, Harry; Jacob, Melissa R; Khan, Shabana I; Walker, Larry A; Muhammad, Ilias; Kerubo, Leonidah O; Midiwo, Jacob O

    2016-07-01

    The roots of the endangered medicinal plant Croton megalocarpoides collected in Kenya were investigated and twenty-two compounds isolated. Among them were twelve new ent-clerodane (1-12) and a new abietane (13) diterpenoids, alongside the known crotocorylifuran (4 a), two known abietane and four known ent-trachylobane diterpenoids, and the triterpenoids, lupeol and acetyl aleurotolic acid. The structures of the compounds were determined using NMR, HRMS and ECD. The isolated compounds were evaluated against a series of microorganisms (fungal and bacteria) and also against Plasmodium falciparum, however no activity was observed.

  6. Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare.

    PubMed

    Zerbe, Philipp; Chiang, Angela; Dullat, Harpreet; O'Neil-Johnson, Mark; Starks, Courtney; Hamberger, Björn; Bohlmann, Jörg

    2014-09-01

    Marrubium vulgare (Lamiaceae) is a medicinal plant whose major bioactive compounds, marrubiin and other labdane-related furanoid diterpenoids, have potential applications as anti-diabetics, analgesics or vasorelaxants. Metabolite and transcriptome profiling of M. vulgare leaves identified five different candidate diterpene synthases (diTPSs) of the TPS-c and TPS-e/f clades. We describe the in vitro and in vivo functional characterization of the M. vulgare diTPS family. In addition to MvEKS ent-kaurene synthase of general metabolism, we identified three diTPSs of specialized metabolism: MvCPS3 (+)-copalyl diphosphate synthase, and the functional diTPS pair MvCPS1 and MvELS. In a sequential reaction, MvCPS1 and MvELS produce a unique oxygenated diterpene scaffold 9,13-epoxy-labd-14-ene en route to marrubiin and an array of related compounds. In contrast with previously known diTPSs that introduce a hydroxyl group at carbon C-8 of the labdane backbone, the MvCPS1-catalyzed reaction proceeds via oxygenation of an intermediate carbocation at C-9, yielding the bicyclic peregrinol diphosphate. MvELS belongs to a subgroup of the diTPS TPS-e/f clade with unusual βα-domain architecture. MvELS is active in vitro and in vivo with three different prenyl diphosphate substrates forming the marrubiin precursor 9,13-epoxy-labd-14-ene, as identified by nuclear magnetic resonance (NMR) analysis, manoyl oxide and miltiradiene. MvELS fills a central position in the biosynthetic system that forms the foundation for the diverse repertoire of Marrubium diterpenoids. Co-expression of MvCPS1 and MvELS in engineered E. coli and Nicotiana benthamiana offers opportunities for producing precursors for an array of biologically active diterpenoids.

  7. New labdane diterpenoids from Croton laui and their anti-inflammatory activities.

    PubMed

    Yang, Li; Zhang, Yu-Bo; Chen, Li-Feng; Chen, Neng-Hua; Wu, Zhong-Nan; Jiang, Si-Qi; Jiang, Lin; Li, Guo-Qiang; Li, Yao-Lan; Wang, Guo-Cai

    2016-10-01

    Nine new labdane diterpenoids (1-9) were isolated from the aerial parts of Croton laui, along with eight known analogues (10-17). Their structures were identified on the basis of the spectral data (IR, UV, HRESIMS, 1D and 2D NMR), and the structure of 8 was confirmed by single crystal X-ray diffraction analyses. In addition, compounds 1, 4, 7, 8, and 14 showed weak anti-inflammatory activities in LPS-stimulated RAW 264.7 cells. PMID:27575472

  8. A new ent-kaurane diterpenoid glycoside from Isodon japonica var. glaucocalyx.

    PubMed

    Xiang, Zhao-Bao; Wang, Guang-Li; Huang, Lan-Zhi; Heng, Lin-Sen; Li, Xiao-Hui

    2013-01-01

    A new ent-kaurane diterpenoid glycoside (1), named glaucocalyxin G, has been isolated from the n-butanol-soluble fraction of the dried whole plants of Isodon japonica var. glaucocalyx along with two known compounds, namely arjunglucoside (2) and kaempferol-3-O-rutinoside (3). The structures of the isolated compounds were assigned on the basis of their (1)H and (13)C NMR spectra including two-dimensional NMR techniques such as HMQC, HMBC, and NOESY experiments and comparison with the literature data. PMID:23614395

  9. Cytotoxic and anti-inflammatory ent-kaurane diterpenoids from Isodon wikstroemioides.

    PubMed

    Wu, Hai-Yan; Wang, Wei-Guang; Jiang, Hua-Yi; Du, Xue; Li, Xiao-Nian; Pu, Jian-Xin; Sun, Han-Dong

    2014-10-01

    Seven new ent-kaurane diterpenoids, isowikstroemins A-G (1-7), were isolated from EtOAc extracts of the aerial parts of Isodon wikstroemioides. Their structures were elucidated by extensive spectroscopic analysis. The isolates were evaluated for their cytotoxicity against five human tumor cell lines, and compounds 1-4 exhibited significant activity with IC50 values ranging from 0.9 to 7.0 μM. In addition, compounds 1, 2, 3, 4, and 7 exhibited inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages. PMID:25128423

  10. Hispidanins A-D: four new asymmetric dimeric diterpenoids from the rhizomes of Isodon hispida.

    PubMed

    Huang, Bo; Xiao, Chao-Jiang; Huang, Zhen-Yuan; Tian, Xin-Yan; Cheng, Xia; Dong, Xiang; Jiang, Bei

    2014-07-01

    Hispidanins A-D (1-4), four unprecedented asymmetric dimeric diterpenoids, were obtained from the rhizomes of Isodon hispida. Their structures were elucidated by extensive spectroscopic analysis (1D and 2D NMR, MS, UV, IR), as well as single-crystal X-ray diffraction analysis. Hispidanin B showed significant cytotoxicities against tumor cell lines SGC7901, SMMC7721, and K562, with IC50 values of 10.7, 9.8, and 13.7 μM, respectively. PMID:24956015

  11. Guanacastane-type diterpenoids from the insect-associated fungus Verticillium dahliae.

    PubMed

    Wu, Fa-Biao; Li, Tian-Xiao; Yang, Ming-Hua; Kong, Ling-Yi

    2016-01-01

    Four new guanacastane-type diterpenoids, namely dahlianes A (1), B (2), C (3), and D (4), were isolated from cultures of Verticillium dahliae. Their structures were elucidated on the basis of extensive spectroscopic data analysis. Their absolute configurations were determined by a combination of Mo2(OAc)4-induced electronic circular dichroism experiment and Mosher ester method. In cytotoxicity evaluation against human tumor cell lines, compounds 2 and 3 exhibited significant cytotoxicities against MCF-7 cell lines with IC50 values of 3.35 and 4.72 μM, respectively.

  12. Highly Rigid Labdane-Type Diterpenoids from a Chinese Liverwort and Light-Driven Structure Diversification.

    PubMed

    Zhou, Jinchuan; Zhang, Jiaozhen; Cheng, Aixia; Xiong, Yuanxin; Liu, Lei; Lou, Hongxiang

    2015-07-17

    Two unprecedented labdane-type diterpenoids haplomintrins A (1) and B (2) with six rings system were isolated from a Chinese liverwort Haplomitrium mnioides. Light-driven reaction of homologous haplomitrenonolides C (6), A (4), and D (3) afforded haplomintrins A-C (1, 2, and 7), respectively, while 4 was converted to more complex congeners haplomintrins D-G (8-11) through intramolecular cyclization. Formation of 1 and 2 from compounds 6 and 4, respectively, helps us to postulate that a photochemical reaction is involved in the biosynthetic pathway. These structure features can be used as molecular markers of H. mnioides, and their allelopathic effects are also preliminarily tested. PMID:26111119

  13. Euphorbia factor L8: a diterpenoid from the seeds of Euphorbia lathyris

    PubMed Central

    Jiao, Wei; Mao, Zhi-hua; Dong, Wei-wei; Deng, Mei-cai; Lu, Run-hua

    2008-01-01

    The title compound [systematic name: (2S*,3S*,4R*,5R*,9S*,11S*,15R*)-5,15-diacet­oxy-3-nicotino­yloxy-14-oxolathyra-6(17),12(E)-diene], C30H37NO7, was isolated from the seeds of Euphorbia lathyris. The tricyclic diterpenoid molecule contains an 11-membered ring, a five-membered ring exhibiting an envelope conformation and a three-membered ring. The 11-membered ring is cis-fused with the three-membered ring and trans-fused with the five-membered ring. PMID:21200892

  14. Antiviral chlorinated daphnane diterpenoid orthoesters from the bark and wood of Trigonostemon cherrieri.

    PubMed

    Allard, Pierre-Marie; Leyssen, Pieter; Martin, Marie-Thérèse; Bourjot, Mélanie; Dumontet, Vincent; Eydoux, Cécilia; Guillemot, Jean-Claude; Canard, Bruno; Poullain, Cyril; Guéritte, Françoise; Litaudon, Marc

    2012-12-01

    The chemical study of the bark and the wood of Trigonostemon cherrieri, a rare endemic plant of New Caledonia, led to the isolation of a series of highly oxygenated daphnane diterpenoid orthoesters (DDO) bearing an uncommon chlorinated moiety: trigocherrins A-F and trigocherriolides A-D. Herein, we describe the isolation and structure elucidation of the DDO (trigocherrins B-F and trigocherriolides A-D). We also report the antiviral activity of trigocherrins A, B and F (1, 2 and 6) and trigocherriolides A, B and C (7-9) against various emerging pathogens: chikungunya virus (CHIKV), Sindbis virus (SINV), Semliki forest virus (SFV) and dengue virus (DENV). PMID:22938995

  15. ent-Labdane Diterpenoids from the Aerial Parts of Eupatorium obtusissmum.

    PubMed

    Castillo, Quírico A; Triana, Jorge; Eiroa, José L; Calcul, Laurent; Rivera, Edwin; Wojtas, Lukasz; Padrón, José M; Boberieth, Lise; Keramane, Mehdi; Abel-Santos, Ernesto; Báez, Luis A; Germosén, Evelyn A

    2016-04-22

    Six new ent-labdane diterpenoids, uasdlabdanes A-F (1-6), were isolated from the aerial parts of Eupatorium obtusissmum. The new structures were elucidated through spectroscopic and spectrometric data analyses. The absolute configurations of compounds 1 and 2 were established by X-ray crystallography, and those of 3-6, by comparison of experimental and calculated electronic circular dichroism spectra. The antiproliferative activity of the compounds was studied in a panel of six representative human solid tumor cell lines and showed GI50 values ranging from 19 to >100 μM. PMID:27023255

  16. Bioactive briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

    PubMed

    Li, Cui; La, Ming-Ping; Tang, Hua; Pan, Wei-Hua; Sun, Peng; Krohn, Karsten; Yi, Yang-Hua; Li, Ling; Zhang, Wen

    2012-07-01

    Six new briarane diterpenoids, gemmacolides T-Y (1-6), were isolated together with three known analogs, juncenolide J (7), praelolide (8), and junceellolide C (9), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed spectroscopic analysis and comparison with reported data. The absolute configuration was suggested based on biosynthetic considerations. In an in vitro bioassay, compounds 3 and 6 showed potent growth inhibition towards tumor cell lines of A549 and MG63, being stronger than the positive control of adriamycin. These compounds also exhibited weak antimicrobial activity against the bacterium Escherichia coli and the fungi Microbotryum violaceum and Septoria tritici.

  17. Two new eunicellin-based diterpenoids from the South China Sea gorgonian Muricella sibogae Nutting.

    PubMed

    Zhou, Yuan-Ming; Chen, Min; Fu, Xiu-Mei; Fang, Yu-Chun; Wang, Chang-Yun

    2014-01-01

    Two new eunicellin-based diterpenoids, sibogins A (1) and B (2), along with one known analogue (3), and four known 9,10-secosteroids (4-7), were isolated from the gorgonian Muricella sibogae Nutting collected from the South China Sea. The structures of the new compounds were elucidated by comprehensive analysis of spectroscopic data, especially by using 2D NMR spectra. The antifouling activity on barnacle Balanus amphitrite and lethality towards brine shrimp Artemia salina of all the isolated compounds were evaluated.

  18. The furano norclerodane diterpenoid disobulbin-D induces apoptosis in normal human liver L-02 cells.

    PubMed

    Ma, Min; Jiang, Zhenzhou; Ruan, Jinlan; Tan, Xinqi; Liu, Jin; Wang, Cuifen; Zha, Xiao Ming; Zhang, Luyong

    2012-09-01

    Disobulbin-D (DBD), a hepatotoxic furano norclerodane diterpenoid, was isolated by bio-guided fractionation from the rhizome of Dioscorea bulbifera L. In working toward elucidating the cellular and molecular mechanisms of DBD toxicity, we treated normal human liver cell line L-02 cells with DBD in vitro and evaluated its toxicity in terms of cell viability, morphologic changes, induction of apoptosis/necrosis, and caspase 3 activity. The viability of L-02 cells was inhibited by DBD in a concentration and time-dependent manner. Apoptosis was supported by the Annexin V and propidium iodide assay, Hoechst 33258 staining, and the occurrence of a sub-G(1) peak. DBD can cause an increase in caspase 3 activity, and pretreatment with Ac-DEVD-CHO blocked cell death and attenuated the apoptosis, showing that DBD-induced L-02 cell apoptosis is caspase 3-dependent. These results suggest that the effects of DBD on the growth of normal human liver L-02 cells may be due to its induction of cell apoptosis, which may also explain the toxicity observed in the plants containing furano clerodane diterpenoids. PMID:21211949

  19. New biological potential of abietane diterpenoids isolated from Salvia austriaca against microbial virulence factors.

    PubMed

    Sadowska, Beata; Kuźma, Łukasz; Micota, Bartłomiej; Budzyńska, Aleksandra; Wysokińska, Halina; Kłys, Arkadiusz; Więckowska-Szakiel, Marzena; Różalska, Barbara

    2016-09-01

    The increasing importance of multi-resistant strains and microbial biofilms in the development of chronic infections has driven the search for more effective alternative therapy including plant-origin preparations. The present study evaluates the broadly-defined antimicrobial activity of two abietane diterpenoids isolated from Salvia austriaca transformed roots: taxodone and 15-deoxy-fuerstione. The direct biostatic/biocidal effect of these phytocompounds and their influence on Staphylococcus aureus and Candida albicans virulence factors/mechanisms (adhesion, biofilm formation, agglutination in human plasma, survival in the blood, germ tube and mycelium formation) were tested using in vitro assays. Both phytocompounds significantly inhibited microbial adhesion and biofilm formation when used at ½ and ¼ MIC. Additionally, taxodone was able to limit staphylococcal survival in human blood, as well as C. albicans germ tube formation and hyphal growth. The tested diterpenoids express significant anti-biofilm activity against both staphylococci and yeast, and adversely affect their virulence factors/mechanisms, which are relevant in the course of the infection in vivo. Therefore, they demonstrate considerable biomedical potential as complements for classic therapy with antibiotics. PMID:27417191

  20. Bioactive diterpenoids and flavonoids from the aerial parts of Scoparia dulcis.

    PubMed

    Liu, Qing; Yang, Qi-Ming; Hu, Hai-Jun; Yang, Li; Yang, Ying-Bo; Chou, Gui-Xin; Wang, Zheng-Tao

    2014-07-25

    Six new diterpenoids, 4-epi-7α-O-acetylscoparic acid A (1), 7α-hydroxyscopadiol (2), 7α-O-acetyl-8,17β-epoxyscoparic acid A (3), neo-dulcinol (4), dulcinodal-13-one (5), and 4-epi-7α-hydroxydulcinodal-13-one (6), and a new flavonoid, dillenetin 3-O-(6″-O-p-coumaroyl)-β-D-glucopyranoside (10), along with 12 known compounds, were isolated from the aerial parts of Scoparia dulcis. The 7S absolute configuration of the new diterpenoids 1-4 and 6 was deduced by comparing their NOESY spectra with that of a known compound, (7S)-4-epi-7-hydroxyscoparic acid A (7), which was determined by the modified Mosher's method. The flavonoids scutellarein (11), hispidulin (12), apigenin (15), and luteolin (16) and the terpenoids 4-epi-scopadulcic acid B (9) and betulinic acid (19) showed more potent α-glucosidase inhibitory effects (with IC50 values in the range 13.7-132.5 μM) than the positive control, acarbose. In addition, compounds 1, 11, 12, 15, 16, and acerosin (17) exhibited peroxisome proliferator-activated receptor gamma (PPAR-γ) agonistic activity, with EC50 values ranging from 0.9 to 24.9 μM. PMID:24955889

  1. Diterpenoids and aromatic compounds from the three New Zealand liverworts Jamesoniella kirkii, Balantiopsis rosea, and Radula species.

    PubMed

    Nagashima, Fumihiro; Kuba, Yoshiyuki; Asakawa, Yoshinori

    2006-06-01

    Three new aromatics were isolated from the New Zealand liverwort Balantiopsis rosea. A new bibenzyl was isolated from an unidentified Radula species, together with known bibenzyls. Jamesoniella kirkii yielded three known ent-isopimarane and two ent-kaurane diterpenoids. Their structures were confirmed by NMR techniques, chemical reaction, and X-ray crystallographic analysis.

  2. Sesqui- and diterpenoids from three New Zealand liverworts: Bazzania novae-zelandiae, Gackstroemia sp. and Dendromastigophora sp.

    PubMed

    Nagashima, Fumihiro; Kuba, Yoshiaki; Ogata, Atsushi; Asakawa, Yoshinori

    2010-01-01

    Two new sesquiterpenoids, 1 and 2, were isolated from the unidentified liverwort Gackstroemia species, and three known sesquiterpenoids, 3-5, and a known sesqui- (6) and diterpenoid (7) were isolated from Bazzania novae-zelandiae and the unidentified Dendromastigophora species, respectively. Their structures were determined by spectroscopic analysis.

  3. New sesquiterpenoids and a diterpenoid from Alpinia oxyphylla.

    PubMed

    Hou, Lei; Ding, Gang; Guo, Baolin; Huang, Wenhua; Zhang, Xiaojian; Sun, Zhiyong; Shi, Xiangfen

    2015-01-16

    The new compounds 2-methyl-6-isopropyl-7-hydroxymethyl naphthalene (1), oxyphyllenone H (2), epi-oxyphyllenone (6), (E)-labda-12,14-dien-15(16)-olide-17-oic acid (3), and two new natural products 4 and 5 were isolated from the ethyl acetate part of 95% ethanol extract of Alpinia oxyphylla, together with six known compounds 7-12. The inhibitory effects of compounds 1-12 on α-glucosidase were evaluated, and compounds 1, 3 and 6 showed moderate bioactive effect, with inhibitory rates of 10.3%, 10.0% and 11.5%, respectively, compared to the positive control acarbose (41.9%) at 20 µg/mL.

  4. Phytol a Natural Diterpenoid with Pharmacological Applications on Central Nervous System: A Review.

    PubMed

    Pereira Costa, Jessica; da Silva Oliveira, Johanssy; Mario Rezende Junior, Luis; de Freitas, Rivelilson Mendes

    2014-01-01

    Phytol (3,7,11,15-tetramethylhexadec-2-en-1-ol), a diterpene member of long and ramified chain of unsaturated acyclic alcohols. The objective of study was to conduct a systematic review of this diterpene and its pharmaceutical applications in Nervous System diseases in humans and/or rodents. Periodicals bases, such as ScienceDirect and PubMed, were used, as well as technological basis of European Patent Office, World Intellectual Property Organization, United States Patent and Trademark Office, Derwent Innovations Index(®), Latin American Bank of Patents and data base of Instituto Nacional de Propriedade Industrial (INPI-National Institute of Industrial Property). The software EndNote-X5 was utilized as reference with the keywords: phytol, anxiolytic, antidepressant and anticonvulsant and their correlations in English, Spanish and Portuguese from January 2003 to June 2014. There are many publications on phytol in international literature. However, there is a reduced number of articles related to pharmacological activities proposed here. In reference to technological bases, patents present a wide range of pharmacological and commercial applications as cosmetics, hypolipodemic, anxiolytic and antidepressant. Therefore, it is necessary to explore phytol molecules, which present high pharmacological potential from scientific and technological points of view, in search of transference of technologies to generate economical and industrial growth. PMID:27099143

  5. Phytol a Natural Diterpenoid with Pharmacological Applications on Central Nervous System: A Review.

    PubMed

    Pereira Costa, Jessica; da Silva Oliveira, Johanssy; Mario Rezende Junior, Luis; de Freitas, Rivelilson Mendes

    2014-01-01

    Phytol (3,7,11,15-tetramethylhexadec-2-en-1-ol), a diterpene member of long and ramified chain of unsaturated acyclic alcohols. The objective of study was to conduct a systematic review of this diterpene and its pharmaceutical applications in Nervous System diseases in humans and/or rodents. Periodicals bases, such as ScienceDirect and PubMed, were used, as well as technological basis of European Patent Office, World Intellectual Property Organization, United States Patent and Trademark Office, Derwent Innovations Index(®), Latin American Bank of Patents and data base of Instituto Nacional de Propriedade Industrial (INPI-National Institute of Industrial Property). The software EndNote-X5 was utilized as reference with the keywords: phytol, anxiolytic, antidepressant and anticonvulsant and their correlations in English, Spanish and Portuguese from January 2003 to June 2014. There are many publications on phytol in international literature. However, there is a reduced number of articles related to pharmacological activities proposed here. In reference to technological bases, patents present a wide range of pharmacological and commercial applications as cosmetics, hypolipodemic, anxiolytic and antidepressant. Therefore, it is necessary to explore phytol molecules, which present high pharmacological potential from scientific and technological points of view, in search of transference of technologies to generate economical and industrial growth.

  6. Jasmonoyl-l-isoleucine is required for the production of a flavonoid phytoalexin but not diterpenoid phytoalexins in ultraviolet-irradiated rice leaves.

    PubMed

    Miyamoto, Koji; Enda, Isami; Okada, Toshiki; Sato, Yumiko; Watanabe, Kohei; Sakazawa, Tomoko; Yumoto, Emi; Shibata, Kyomi; Asahina, Masashi; Iino, Moritoshi; Yokota, Takao; Okada, Kazunori; Yamane, Hisakazu

    2016-10-01

    Rice produces low-molecular-weight antimicrobial compounds known as phytoalexins, in response to not only pathogen attack but also abiotic stresses including ultraviolet (UV) irradiation. Rice phytoalexins are composed of diterpenoids and a flavonoid. Recent studies have indicated that endogenous jasmonyl-l-isoleucine (JA-Ile) is not necessarily required for the production of diterpenoid phytoalexins in blast-infected or CuCl2-treated rice leaves. However, JA-Ile is required for the accumulation of the flavonoid phytoalexin, sakuranetin. Here, we investigated the roles of JA-Ile in UV-induced phytoalexin production. We showed that UV-irradiation induces the biosynthesis of JA-Ile and its precursor jasmonic acid. We also showed that rice jasmonate biosynthesis mutants produced diterpenoid phytoalexins but not sakuranetin in response to UV, indicating that JA-Ile is required for the production of sakuranetin but not diterpenoid phytoalexins in UV-irradiated rice leaves. PMID:27240428

  7. Jasmonoyl-l-isoleucine is required for the production of a flavonoid phytoalexin but not diterpenoid phytoalexins in ultraviolet-irradiated rice leaves.

    PubMed

    Miyamoto, Koji; Enda, Isami; Okada, Toshiki; Sato, Yumiko; Watanabe, Kohei; Sakazawa, Tomoko; Yumoto, Emi; Shibata, Kyomi; Asahina, Masashi; Iino, Moritoshi; Yokota, Takao; Okada, Kazunori; Yamane, Hisakazu

    2016-10-01

    Rice produces low-molecular-weight antimicrobial compounds known as phytoalexins, in response to not only pathogen attack but also abiotic stresses including ultraviolet (UV) irradiation. Rice phytoalexins are composed of diterpenoids and a flavonoid. Recent studies have indicated that endogenous jasmonyl-l-isoleucine (JA-Ile) is not necessarily required for the production of diterpenoid phytoalexins in blast-infected or CuCl2-treated rice leaves. However, JA-Ile is required for the accumulation of the flavonoid phytoalexin, sakuranetin. Here, we investigated the roles of JA-Ile in UV-induced phytoalexin production. We showed that UV-irradiation induces the biosynthesis of JA-Ile and its precursor jasmonic acid. We also showed that rice jasmonate biosynthesis mutants produced diterpenoid phytoalexins but not sakuranetin in response to UV, indicating that JA-Ile is required for the production of sakuranetin but not diterpenoid phytoalexins in UV-irradiated rice leaves.

  8. ent-Kaurane Diterpenoids from Chinese Liverworts and Their Antitumor Activities through Michael Addition As Detected in Situ by a Fluorescence Probe.

    PubMed

    Lin, Zhaomin; Guo, Yanxia; Gao, Yanhui; Wang, Shuqi; Wang, Xiaoning; Xie, Zhiyu; Niu, Huanmin; Chang, Wenqiang; Liu, Lei; Yuan, Huiqing; Lou, Hongxiang

    2015-05-14

    It is generally accepted that the origin of the cytotoxicity of ent-kaurane diterpenoids is due to the formation of reactive oxygen species (ROS) and that the α,β-unsaturated carbonyl is a pivotal moiety. Herein we demonstrate the isolation of 32 new and 12 known ent-kaurane diterpenoids from two Chinese liverworts. These compounds and three semisynthesized derivatives were screened against human cancer cell lines. The results revealed that their anticancer activities are caused by ROS formation through Michael modification of the protein thiols and depletion of glutathione unselectively. We also found that N-acetylcysteine reverses the cytotoxicity of these diterpenoids by forming Michael adducts, not through a well-recognized ROS scavenging pathway as previously reported. In situ intracellular thiol detection helped us visualize the intracellular distribution of the diterpenoids and determine the potency of their cytotoxicity. An alkaline analogue was found to be more selective because of the altered subcellular distribution. PMID:25856683

  9. ent-Kaurane Diterpenoids from Chinese Liverworts and Their Antitumor Activities through Michael Addition As Detected in Situ by a Fluorescence Probe.

    PubMed

    Lin, Zhaomin; Guo, Yanxia; Gao, Yanhui; Wang, Shuqi; Wang, Xiaoning; Xie, Zhiyu; Niu, Huanmin; Chang, Wenqiang; Liu, Lei; Yuan, Huiqing; Lou, Hongxiang

    2015-05-14

    It is generally accepted that the origin of the cytotoxicity of ent-kaurane diterpenoids is due to the formation of reactive oxygen species (ROS) and that the α,β-unsaturated carbonyl is a pivotal moiety. Herein we demonstrate the isolation of 32 new and 12 known ent-kaurane diterpenoids from two Chinese liverworts. These compounds and three semisynthesized derivatives were screened against human cancer cell lines. The results revealed that their anticancer activities are caused by ROS formation through Michael modification of the protein thiols and depletion of glutathione unselectively. We also found that N-acetylcysteine reverses the cytotoxicity of these diterpenoids by forming Michael adducts, not through a well-recognized ROS scavenging pathway as previously reported. In situ intracellular thiol detection helped us visualize the intracellular distribution of the diterpenoids and determine the potency of their cytotoxicity. An alkaline analogue was found to be more selective because of the altered subcellular distribution.

  10. Inhibition of Helicobacter pylori and Its Associate Urease by Labdane Diterpenoids Isolated from Andrographis paniculata.

    PubMed

    Shaikh, Rafik U; Dawane, Ashwini A; Pawar, Rajendra P; Gond, Dhananjay S; Meshram, Rohan J; Gacche, Rajesh N

    2016-03-01

    The present study was carried out to evaluate anti-Helicobacter pylori and its associated urease activity of labdane diterpenoids isolated from Andrographis paniculata. A molecular docking analysis was performed by using ArgusLab 4.0.1 software. The results obtained indicate that compound A possesses strong inhibition to H. pylori, 28 ± 2.98 (minimum inhibitory concentration, 9 µg/mL), and its urease, 85.54 ± 2.62% (IC50 , 20.2 µg/mL). Compounds B, C, and D also showed moderate inhibition to H. pylori and its urease. The obtained results were in agreement with the molecular docking analysis of compounds. The phytochemicals under investigation were found to be promising antibacterial agents. Moreover, the isolated compounds can be considered as a resource for searching novel anti-H. pylori agents possessing urease inhibition.

  11. Structure and antibacterial property of a new diterpenoid from Euphorbia helioscopia.

    PubMed

    Geng, Di; Yi, Li-Tao; Shi, Yao; Min, Zhi-Da

    2015-09-01

    The present study was designed to isolate and evaluate the antibacterial activity of the compounds from the whole plant of Euphorbia helioscopia L.. Various chromatographic techniques were used to isolate and purify the compound. The structure of the compound was elucidated on basis of spectral data ((1)H NMR, (13)C NMR, (1)H-(1)H COSY, HSQC, HMBC, NOESY, IR, and HR-ESI-MS). A new jatrophone-type diterpenoid (14α,15β-diacetoxy-3β-benzoyloxy-7β-nicotinoyloxy-9-oxo-jatropha-5E,11E-diene), named euphoheliosnoid E (1), was isolated from the whole plant of E. helioscopia L. Compound 1 showed significant anti-microbial activity against oral pathogens. PMID:26412431

  12. Rapid Bioassay-Guided Isolation of Antibacterial Clerodane Type Diterpenoid from Dodonaea viscosa (L.) Jaeq.

    PubMed Central

    Khurram, Muhammad; Lawton, Linda A.; Edwards, Christine; Iriti, Marcello; Hameed, Abdul; Khan, Murad A.; Khan, Farman A.; ur Rahman, Shafiq

    2015-01-01

    Plant extracts are complex matrices and, although crude extracts are widely in use, purified compounds are pivotal in drug discovery. This study describes the application of automated preparative-HPLC combined with a rapid off-line bacterial bioassay, using reduction of a tetrazolium salt as an indicator of bacterial metabolism. This approach enabled the identification of fractions from Dodonaea viscosa that were active against Staphylococcus aureus and Escherichia coli, which, ultimately, resulted in the identification of a clerodane type diterpenoid, 6β-hydroxy-15,16-epoxy-5β, 8β, 9β, 10α-cleroda-3, 13(16), 14-trien-18-oic acid, showing bacteriostatic activity (minimum inhibitory concentration (MIC) = 64–128 µg/mL) against test bacteria. To the best of our knowledge, this is the first report on antibacterial activity of this metabolite from D. viscosa. PMID:26343638

  13. Abietane-type diterpenoids from the roots of Caryopteris mongolica and their cholinesterase inhibitory activities.

    PubMed

    Murata, Toshihiro; Ishikawa, Yoshinobu; Saruul, Erdenebileg; Selenge, Erdenechimeg; Sasaki, Kenroh; Umehara, Kaoru; Yoshizaki, Fumihiko; Batkhuu, Javzan

    2016-10-01

    Eleven abietane-type diterpenoids and two known abietanes were isolated from the roots of Caryopteris mongolica, and their structures were characterized. The absolute configurations at C-5 and C-10 were determined from the NMR data, including from the nuclear Overhauser effect and CD spectra, and the absolute configuration of C-16 in the hydroxypropyl group was determined via a modified Mosher's method. Furthermore, the previously unknown absolute configuration of the C-15 of cyrtophyllone B was determined to be in an R-configuration using X-ray crystallography. To estimate the preventive effects of the isolates for neurodegenerative disease development, their inhibitory activities against acetylcholinesterase (AChE) from human erythrocytes and butyrylcholinesterase (BChE) from horse serum were evaluated.

  14. Rearranged diterpenoids from the biotransformation of ent-trachyloban-18-oic acid by Rhizopus arrhizus.

    PubMed

    Leverrier, Aurélie; Martin, Marie-Thérèse; Servy, Claudine; Ouazzani, Jamal; Retailleau, Pascal; Awang, Khalijah; Mukhtar, Mat Ropi; Guéritte, Françoise; Litaudon, Marc

    2010-06-25

    In our search for inhibitors of the antiapoptotic protein Bcl-xL, investigation of Xylopia caudata afforded a new diterpenoid, ent-trachyloban-4beta-ol (2), and five known ent-trachylobane or ent-atisane compounds. Only ent-trachyloban-18-oic acid (1) exhibited weak binding activity to Bcl-xL. These compounds exhibited cytotoxicity against KB and HCT-116 cell lines with IC(50) values between 10 and 30 microM. Bioconversion of compound 1 by Rhizopus arrhizus afforded new hydroxylated metabolites (3-7) of the ent-trachylobane and ent-kaurene type and compound 8, with a rearranged pentacyclic carbon framework that was named rhizopene. Compounds 3-8 were noncytotoxic to the two cancer cell lines, and compounds 3 and 5 exhibited only weak binding affinity for Bcl-xL. PMID:20481544

  15. Notolutesins A-J, dolabrane-type diterpenoids from the Chinese liverwort Notoscyphus lutescens.

    PubMed

    Wang, Song; Li, Rui-Juan; Zhu, Rong-Xiu; Hu, Xiao-Yan; Guo, Yan-Xia; Zhou, Jin-Chuan; Lin, Zhao-Min; Zhang, Jiao-Zhen; Wu, Jing-Yi; Kang, Ya-Qi; Morris-Natschke, Susan L; Lee, Kuo-Hsiung; Yuan, Hui-Qing; Lou, Hong-Xiang

    2014-09-26

    Ten new dolabrane-type diterpenoids, notolutesins A-J (1-10), were isolated from the Chinese liverwort Notoscyphus lutescens, along with four known compounds. The structures of the new compounds were established on the basis of extensive spectroscopic data, and that of 1 was confirmed by single-crystal X-ray crystallography. The absolute configuration of 1 was determined by comparing its experimental and calculated electronic circular dichroism spectra. All of the isolates were evaluated for their cytotoxicity against a small panel of human cancer cell lines, and compound 1 exhibited an IC50 value of 6.2 μM against the PC3 human prostate cancer cell line. PMID:25226363

  16. Diterpenoids from the Endophytic Fungus Botryosphaeria sp. P483 of the Chinese Herbal Medicine Huperzia serrata.

    PubMed

    Chen, Yan-Mei; Yang, Yin-He; Li, Xiao-Nian; Zou, Cheng; Zhao, Pei-Ji

    2015-01-01

    Two new tetranorlabdane diterpenoids, named botryosphaerins G (1) and H (2), were isolated from the solid fermentation products of Botryosphaeria sp. P483 along with seven known tetranorlabdane diterpenes (3-9). Their structures were elucidated by extensive analysis, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). Their absolute configuration was confirmed by single-crystal X-ray diffraction analyses using the anomalous scattering of Cu Kα radiation. All of the isolated compounds were tested for activity against phytopathogenic fungi and nematodes. Compounds 2 and 3 showed antifungal activity and compound 2 showed weak nematicidal activity. PMID:26393542

  17. Abietane-type diterpenoids from the roots of Caryopteris mongolica and their cholinesterase inhibitory activities.

    PubMed

    Murata, Toshihiro; Ishikawa, Yoshinobu; Saruul, Erdenebileg; Selenge, Erdenechimeg; Sasaki, Kenroh; Umehara, Kaoru; Yoshizaki, Fumihiko; Batkhuu, Javzan

    2016-10-01

    Eleven abietane-type diterpenoids and two known abietanes were isolated from the roots of Caryopteris mongolica, and their structures were characterized. The absolute configurations at C-5 and C-10 were determined from the NMR data, including from the nuclear Overhauser effect and CD spectra, and the absolute configuration of C-16 in the hydroxypropyl group was determined via a modified Mosher's method. Furthermore, the previously unknown absolute configuration of the C-15 of cyrtophyllone B was determined to be in an R-configuration using X-ray crystallography. To estimate the preventive effects of the isolates for neurodegenerative disease development, their inhibitory activities against acetylcholinesterase (AChE) from human erythrocytes and butyrylcholinesterase (BChE) from horse serum were evaluated. PMID:27298275

  18. Mass spectrometric methodology for the analysis of highly oxidized diterpenoid acids in Old Master paintings.

    PubMed

    Berg; Boon; Pastorova; Spetter

    2000-04-01

    Diterpenoid resins from larch and pine trees and the corresponding fractions in a >100-year-old wax-resin adhesive and varnish and a 200-year-old resin/oil paint sample were analysed with by gas chromatography/mass spectrometry (GC/MS) using several off-line and on-line derivatization methods. The main resin compounds were highly oxidized abietic acids. Important products found are hydroxydehydroabietic acids (OH-DHAs), 7-oxoDHA, di-OH-DHAs and 15-OH-7-oxoDHA. The last two compounds have not been reported to occur in artworks before. Larixyl acetate, an important marker from larch resins, was found to be still present in high amounts in the adhesive. A large number of mass spectra of the different oxidation products and larixol and larixyl acetate are presented and their fragmentation behaviour under electron impact conditions is discussed. An index for the degree of oxidation (IDOX) of the abietic acids is presented as an indicator of the degree of oxidation of the matrix in which the resin is present. The IDOX was 0.10, 0.67, 0.81 and 0.76 for the fresh resins, the dark-aged adhesive, the aged varnish and the resin/oil paint, respectively (measured with pyrolysis (Py)-tetramethylammonium hydroxide (TMAH)-GC/MS). Py-TMAH-GC/MS and direct temperature-resolved mass spectrometry are reliable, valuable and fast techniques for the assessment of the presence and degree of oxidation of diterpenoid resins. Copyright 2000 John Wiley & Sons, Ltd. PMID:10797648

  19. Euphorikanin A, a Diterpenoid Lactone with a Fused 5/6/7/3 Ring System from Euphorbia kansui.

    PubMed

    Fei, Dong-Qing; Dong, Le-Le; Qi, Feng-Ming; Fan, Gai-Xia; Li, Hui-Hong; Li, Zheng-Yu; Zhang, Zhan-Xin

    2016-06-17

    Euphorikanin A (1), an unprecedented diterpenoid lactone which possesses a novel 5/6/7/3-fused tetracyclic ring skeleton, was isolated from the roots of Euphorbia kansui. The chemical structure and absolute stereochemistry were elucidated on the basis of extensive spectroscopic methods and single-crystal X-ray diffraction analysis. Compound 1 exhibited moderate cytotoxicity against two human tumor cell lines HeLa and NCI-446. A proposed biosynthetic pathway of compound 1 is also described. PMID:27230557

  20. The Diterpenoid 7-Keto-Sempervirol, Derived from Lycium chinense, Displays Anthelmintic Activity against both Schistosoma mansoni and Fasciola hepatica

    PubMed Central

    Edwards, Jennifer; Brown, Martha; Peak, Emily; Bartholomew, Barbara; Nash, Robert J.; Hoffmann, Karl F.

    2015-01-01

    Background Two platyhelminths of biomedical and commercial significance are Schistosoma mansoni (blood fluke) and Fasciola hepatica (liver fluke). These related trematodes are responsible for the chronic neglected tropical diseases schistosomiasis and fascioliasis, respectively. As no vaccine is currently available for anti-flukicidal immunoprophylaxis, current treatment is mediated by mono-chemical chemotherapy in the form of mass drug administration (MDA) (praziquantel for schistosomiasis) or drenching (triclabendazole for fascioliasis) programmes. This overreliance on single chemotherapeutic classes has dramatically limited the number of novel chemical entities entering anthelmintic drug discovery pipelines, raising significant concerns for the future of sustainable blood and liver fluke control. Methodology/ Principle Findings Here we demonstrate that 7-keto-sempervirol, a diterpenoid isolated from Lycium chinense, has dual anthelmintic activity against related S. mansoni and F. hepatica trematodes. Using a microtiter plate-based helminth fluorescent bioassay (HFB), this activity is specific (Therapeutic index = 4.2, when compared to HepG2 cell lines) and moderately potent (LD50 = 19.1 μM) against S. mansoni schistosomula cultured in vitro. This anti-schistosomula effect translates into activity against both adult male and female schistosomes cultured in vitro where 7-keto-sempervirol negatively affects motility/behaviour, surface architecture (inducing tegumental holes, tubercle swelling and spine loss/shortening), oviposition rates and egg morphology. As assessed by the HFB and microscopic phenotypic scoring matrices, 7-keto-sempervirol also effectively kills in vitro cultured F. hepatica newly excysted juveniles (NEJs, LD50 = 17.7 μM). Scanning electron microscopy (SEM) evaluation of adult F. hepatica liver flukes co-cultured in vitro with 7-keto-sempervirol additionally demonstrates phenotypic abnormalities including breaches in tegumental integrity and

  1. Noncariogenic intense natural sweeteners.

    PubMed

    Kinghorn, A D; Kaneda, N; Baek, N I; Kennelly, E J; Soejarto, D D

    1998-09-01

    There is a definite relationship between the dietary consumption of sucrose and the incidence of dental caries. Noncaloric sucrose substitutes for use in the sweetening of foods, beverages, and medicines may be either synthetic compounds or natural products. In the United States, four potently sweet artificial sweeteners are approved, namely, saccharin, aspartame, acesulfame potassium, and sucralose. Highly sweet plant constituents are used in Japan and some other countries, including the diterpene glycoside stevioside and the protein thaumatin. Recent progress in a research project oriented towards the discovery and evaluation of novel potentially noncariogenic sweeteners from plants has focused on substances in the sesquiterpenoid, diterpenoid, triterpenoid, steroidal saponin, and proanthocyanidin structural classes. The feasibility of using Mongolian gerbil electrophysiological and behavioral assays to monitor the sweetness of plant extracts, chromatographic fractions, and pure isolates has been investigated. An in vivo cariogenicity study on the commercially available natural sweeteners stevioside and rebaudioside A has been carried out. PMID:9735874

  2. Noncariogenic intense natural sweeteners.

    PubMed

    Kinghorn, A D; Kaneda, N; Baek, N I; Kennelly, E J; Soejarto, D D

    1998-09-01

    There is a definite relationship between the dietary consumption of sucrose and the incidence of dental caries. Noncaloric sucrose substitutes for use in the sweetening of foods, beverages, and medicines may be either synthetic compounds or natural products. In the United States, four potently sweet artificial sweeteners are approved, namely, saccharin, aspartame, acesulfame potassium, and sucralose. Highly sweet plant constituents are used in Japan and some other countries, including the diterpene glycoside stevioside and the protein thaumatin. Recent progress in a research project oriented towards the discovery and evaluation of novel potentially noncariogenic sweeteners from plants has focused on substances in the sesquiterpenoid, diterpenoid, triterpenoid, steroidal saponin, and proanthocyanidin structural classes. The feasibility of using Mongolian gerbil electrophysiological and behavioral assays to monitor the sweetness of plant extracts, chromatographic fractions, and pure isolates has been investigated. An in vivo cariogenicity study on the commercially available natural sweeteners stevioside and rebaudioside A has been carried out.

  3. Scapaundulin C, a novel labdane diterpenoid isolated from Chinese liverwort Scapania undulate, inhibits acetylcholinesterase activity.

    PubMed

    Kang, Ya-Qi; Zhou, Jin-Chuan; Fan, Pei-Hong; Wang, Shu-Qi; Lou, Hong-Xiang

    2015-12-01

    In the present study, scapaundulin C (1), a new labdane diterpenoid, and four related known compounds scapaundulin A (2), 5α, 8α, 9α-trihydroxy-13E-labden-12-one (3), 5α, 8α-dihydroxy-13E-labden-12-one (4), and (13S)-15-hydroxylabd-8 (17)-en-19-oic acid (5), were isolated from the Chinese liverwort Scapania undulate (L.) Dum., using column chromatography. The structures of these compounds were determined on the basis of 1D- and 2D-NMR analyses. The acetylcholinesterase (AchE) inhibitory activity was evaluated using a bioautographic TLC assay and the cytotoxic activity was evaluated by the MTT method. All the compounds were reported for the first time to exhibit moderate AchE inhibitory activity with minimal inhibitory quantities ranging from 250 to 500 ng. All the compounds were tested for their cytotoxicity against five human tumor cell lines, A549, K562, A2780, Hela, and HT29, and compounds 3 and 4 exhibited moderate inhibitory effects on the growth of A2780 cells. PMID:26721712

  4. Bioactive Enmein-Type ent-Kaurane Diterpenoids from Isodon phyllostachys.

    PubMed

    Yang, Jin; Wang, Wei-Guang; Wu, Hai-Yan; Du, Xue; Li, Xiao-Nian; Li, Yan; Pu, Jian-Xin; Sun, Han-Dong

    2016-01-22

    Thirty-two enmein-type ent-kaurane diterpenoids, including 13 new compounds, were isolated from the aerial parts of Isodon phyllostachys. Compounds 1 and 2 are the first examples of 3,20:6,20-diepoxyenmein-type ent-kauranoids, and the structures of these new compounds were established mainly by analyzing NMR and HREIMS data. The absolute configurations of 1 and 8 and the relative configuration of 9 were determined using single-crystal X-ray diffraction. Compounds 11, 15, 20, and 21 were active against five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW-480), with IC50 values ranging from 1.2 to 5.0 μM. Compounds 3, 11, 15, 17, 20, 21, 25, and 29 strongly inhibited NO production in LPS-stimulated RAW264.7 cells, with IC50 values ranging from 0.74 to 4.93 μM. PMID:26757019

  5. Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model.

    PubMed

    Strobykina, Irina Yu; Belenok, Mayya G; Semenova, Marina N; Semenov, Victor V; Babaev, Vasiliy M; Rizvanov, Ildar Kh; Mironov, Vladimir F; Kataev, Vladimir E

    2015-06-26

    A series of novel triphenylphosphonium (TPP) cations of the diterpenoid isosteviol (1, 16-oxo-ent-beyeran-19-oic acid) have been synthesized and evaluated in an in vivo phenotypic sea urchin embryo assay for antimitotic activity. The TPP moiety was applied as a carrier to provide selective accumulation of a connected compound into mitochondria. When applied to fertilized eggs, the targeted isosteviol TPP conjugates induced mitotic arrest with the formation of aberrant multipolar mitotic spindles, whereas both isosteviol and the methyltriphenylphosphonium cation were inactive. The structure-activity relationship study revealed the essential role of the TPP group for the realization of the isosteviol effect, while the chemical structure and the length of the linker only slightly influenced the antimitotic potency. The results obtained using the sea urchin embryo model suggested that TPP conjugates of isosteviol induced mitotic spindle defects and mitotic arrest presumably by affecting mitochondrial DNA. Since targeting mitochondria is considered as an encouraging strategy for cancer therapy, TPP-isosteviol conjugates may represent promising candidates for further design as anticancer agents.

  6. Peltate glandular trichomes of Colquhounia seguinii harbor new defensive clerodane diterpenoids.

    PubMed

    Li, Chun-Huan; Liu, Yan; Hua, Juan; Luo, Shi-Hong; Li, Sheng-Hong

    2014-09-01

    Glandular trichomes produce a wide variety of secondary metabolites that are considered as major defensive chemicals against herbivore attack. The morphology and secondary metabolites of the peltate glandular trichomes of a lianoid Labiatae, Colquhounia seguinii Vaniot, were investigated. Three new clerodane diterpenoids, seguiniilactones A-C (1-3), were identified through precise trichome collection with laser microdissection, metabolic analysis with ultra performance liquid chromatography-tandem mass spectrometer, target compound isolation with classical phytochemical techniques, structure elucidation with spectroscopic methods. All compounds showed significant antifeedant activity against a generalist plant-feeding insect Spodoptera exigua. Seguiniilactone A (1) was approximately 17-fold more potent than the commercial neem oil. α-Substituted α,β-unsaturated γ-lactone functionality was found to be crucial for strong antifeedant activity of this class of compounds. Quantitative results indicated that the levels of these compounds in the peltate glandular trichomes and leaves were sufficiently high to deter the feeding by generalist insects. Moderate antifungal activity was observed for seguiniilactone C (3) against six predominant fungal species isolated from the diseased leaves of C. seguinii, while seguiniilactones A and B were generally inactive. These findings suggested that seguiniilactones A-C might be specialized secondary metabolites in peltate glandular trichomes for the plant defense against insect herbivores and pathogens. PMID:25048077

  7. Triphenylphosphonium Cations of the Diterpenoid Isosteviol: Synthesis and Antimitotic Activity in a Sea Urchin Embryo Model.

    PubMed

    Strobykina, Irina Yu; Belenok, Mayya G; Semenova, Marina N; Semenov, Victor V; Babaev, Vasiliy M; Rizvanov, Ildar Kh; Mironov, Vladimir F; Kataev, Vladimir E

    2015-06-26

    A series of novel triphenylphosphonium (TPP) cations of the diterpenoid isosteviol (1, 16-oxo-ent-beyeran-19-oic acid) have been synthesized and evaluated in an in vivo phenotypic sea urchin embryo assay for antimitotic activity. The TPP moiety was applied as a carrier to provide selective accumulation of a connected compound into mitochondria. When applied to fertilized eggs, the targeted isosteviol TPP conjugates induced mitotic arrest with the formation of aberrant multipolar mitotic spindles, whereas both isosteviol and the methyltriphenylphosphonium cation were inactive. The structure-activity relationship study revealed the essential role of the TPP group for the realization of the isosteviol effect, while the chemical structure and the length of the linker only slightly influenced the antimitotic potency. The results obtained using the sea urchin embryo model suggested that TPP conjugates of isosteviol induced mitotic spindle defects and mitotic arrest presumably by affecting mitochondrial DNA. Since targeting mitochondria is considered as an encouraging strategy for cancer therapy, TPP-isosteviol conjugates may represent promising candidates for further design as anticancer agents. PMID:26042548

  8. Effects of radix curcumae-derived diterpenoid C on Helicobacter pylori-induced inflammation and nuclear factor kappa B signal pathways

    PubMed Central

    Huang, Xuan; Lv, Bin; Zhang, Shuo; Dai, Qun; Chen, Bing-Bing; Meng, Li-Na

    2013-01-01

    AIM: To study effect of diterpenoid C extracted from radix curcumae on Helicobacter pylori (H. pylori)-infected inflammation, intestinal metaplasia, and nuclear factor kappa B (NF-κB) signaling pathway in vitro. METHODS: We used I-type H. pylori to infect human gastric epithelial gastric epithelium cell line (GES-1) cell lines, and then H. pylori-infected GES-1 cells were treated with radix curcumae (RC)-derived diterpenoid C of different concentrations (5, 10, 20 μg/mL) and amoxicillin. The expression of p65, IκB kinase (IKK) α and IKKγ proteins was detected with Western blotting, and the expression of interleukin (IL)-8, IL-6 and IL-4 was determined with enzyme-linked immunosorbent assay method. Data were analyzed using SPSS software ver18.0. For comparisons between groups of more than two unpaired values, one-way analysis of variance (ANOVA) was used. If an ANOVA F value was significant, post hoc comparisons were performed between groups. If results were not normally distributed, the Mann-Whitney U test was used to compare two groups of unpaired values, whereas for comparisons between groups of more than two unpaired values, the Kruskal-Wallis H test was used. Statistical significance was established at P < 0.05. RESULTS: The MTT assay results revealed the inhibited rate of GES-1, and indicated that the IC5 of RC-derived diterpenoid C and amoxicillin all were 5 μg/mL for gastric GES-1 cells. The expression of IL-8 was significantly increased, especially at 12 h time point; and the expression of IL-4 was decreased in H. pylori-infected GES-1 cells. After H. pylori-infected GES-1 cells were treated with RC-derived diterpenoid C of different concentrations and amoxicillin, the expression of IL-8 was decreased at 12, 24, 48, 72 h points (P < 0.01), especially in high-concentration diterpenoid C (20 μg/mL) group; and the expression of IL-4 was increased, especially in moderate and high-concentration diterpenoid C (10 and 20 μg/mL) groups. RC

  9. Bioactive 11,20-epoxy-3,5(16)-diene briarane diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

    PubMed

    Li, Cui; La, Ming-Ping; Li, Ling; Li, Xiu-Bao; Tang, Hua; Liu, Bao-Shu; Krohn, Karsten; Sun, Peng; Yi, Yang-Hua; Zhang, Wen

    2011-07-22

    Seven new briarane diterpenoids, gemmacolides G-M (1-7), were isolated together with two known analogues, juncin O and junceellolide C, from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by detailed analysis of spectroscopic data and comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells. In particular, compound 4 was more active than the positive control adriamycin against A549 cells. Compounds 4 and 7 also exhibited weak antimicrobial activity against the bacterium Bacillus megaterium and the fungus Septoria tritici, respectively.

  10. Scapairrins A-Q, Labdane-Type Diterpenoids from the Chinese Liverwort Scapania irrigua and Their Cytotoxic Activity.

    PubMed

    Zhang, Jiaozhen; Li, Yi; Zhu, Rongxiu; Li, Lin; Wang, Yongjie; Zhou, Jinchuan; Qiao, Yanan; Zhang, Zhenwei; Lou, Hongxiang

    2015-08-28

    Seventeen new labdane-type diterpenoids, scapairrins A-Q (1-17), including six pairs of diastereoisomers, and three known analogues (18-20) were isolated from the Chinese liverwort Scapania irrigua. The structures of 1-17 were determined based on a combination of the analysis of their MS and NMR spectroscopic data, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Cytotoxicity testing showed that compounds 7-10 exhibited inhibitory activities against a small panel of human cancer cell lines. PMID:26252628

  11. A novel isopimarane diterpenoid with acetylcholinesterase inhibitory activity from Nepeta sorgerae, an endemic species to the Nemrut Mountain.

    PubMed

    Yilmaz, Anil; Cağlar, Pinar; Dirmenci, Tuncay; Gören, Nezhun; Topçu, Gülaçti

    2012-06-01

    From the dichloromethane extract of Nepeta sorgerae, the isolation and structure elucidation are now reported of a new isopimarane diterpenoid, named sorgerolone, and two known triterpenoids, oleanolic acid and ursolic acid. Antioxidant activity of the extracts and the isolated terpenoids was determined by the DPPH free radical scavenging and lipid peroxidation inhibition (beta-carotene bleaching) methods. Anticholinesterase activity of the extracts and isolates was investigated by Ellman's method against AChE and BChE enzymes. Although the antioxidant activity results were low, the AChE enzyme inhibition of the extracts and terpenoids was very promising.

  12. A novel isopimarane diterpenoid with acetylcholinesterase inhibitory activity from Nepeta sorgerae, an endemic species to the Nemrut Mountain.

    PubMed

    Yilmaz, Anil; Cağlar, Pinar; Dirmenci, Tuncay; Gören, Nezhun; Topçu, Gülaçti

    2012-06-01

    From the dichloromethane extract of Nepeta sorgerae, the isolation and structure elucidation are now reported of a new isopimarane diterpenoid, named sorgerolone, and two known triterpenoids, oleanolic acid and ursolic acid. Antioxidant activity of the extracts and the isolated terpenoids was determined by the DPPH free radical scavenging and lipid peroxidation inhibition (beta-carotene bleaching) methods. Anticholinesterase activity of the extracts and isolates was investigated by Ellman's method against AChE and BChE enzymes. Although the antioxidant activity results were low, the AChE enzyme inhibition of the extracts and terpenoids was very promising. PMID:22816286

  13. Cytotoxic and Pro-Apoptotic Effects of Cassane Diterpenoids from the Seeds of Caesalpinia sappan in Cancer Cells.

    PubMed

    Bao, Han; Zhang, Le-Le; Liu, Qian-Yu; Feng, Lu; Ye, Yang; Lu, Jin-Jian; Lin, Li-Gen

    2016-01-01

    The chemical study on the seeds of Caesalpinia sappan led to the isolation of five new cassane diterpenoids, phanginins R‒T (1-3) and caesalsappanins M and N (4 and 5), together with seven known compounds 6-12. Their structures were elucidated on the basis of NMR and HRESIMS analyses. The absolute configurations of compounds 1 and 4 were determined by the corresponding CD spectra. All the isolated compounds were tested for their cytotoxicity against ovarian cancer A2780 and HEY, gastric cancer AGS, and non-small cell lung cancer A549 cells. Compound 1 displayed significant toxicity against the four cell lines with the IC50 values of 9.9 ± 1.6 µM, 12.2 ± 6.5 µM, 5.3 ± 1.9 µM, and 12.3 ± 3.1 µM, respectively. Compound 1 induced G1 phase cell cycle arrest in A2780 cells. Furthermore, compound 1 dose-dependently induced A2780 cells apoptosis as evidenced by Hoechst 33342 staining, Annexin V positive cells, the up-regulated cleaved-PARP and the enhanced Bax/Bcl-2 ratio. What's more, compound 1 also promoted the expression of the tumor suppressor p53 protein. These findings indicate that cassane diterpenoids might have potential as anti-cancer agents, and further in vivo animal studies and structural modification investigation are needed. PMID:27322234

  14. Serrulatane Diterpenoid from Eremophila neglecta Exhibits Bacterial Biofilm Dispersion and Inhibits Release of Pro-inflammatory Cytokines from Activated Macrophages.

    PubMed

    Mon, Htwe H; Christo, Susan N; Ndi, Chi P; Jasieniak, Marek; Rickard, Heather; Hayball, John D; Griesser, Hans J; Semple, Susan J

    2015-12-24

    The purpose of this study was to assess the biofilm-removing efficacy and inflammatory activity of a serrulatane diterpenoid, 8-hydroxyserrulat-14-en-19-oic acid (1), isolated from the Australian medicinal plant Eremophila neglecta. Biofilm breakup activity of compound 1 on established Staphylococcus epidermidis and Staphylococcus aureus biofilms was compared to the antiseptic chlorhexidine and antibiotic levofloxacin. In a time-course study, 1 was deposited onto polypropylene mesh to mimic a wound dressing and tested for biofilm removal. The ex-vivo cytotoxicity and effect on lipopolysaccharide-induced pro-inflammatory cytokine release were studied in mouse primary bone-marrow-derived macrophage (BMDM) cells. Compound 1 was effective in dispersing 12 h pre-established biofilms with a 7 log10 reduction of viable bacterial cell counts, but was less active against 24 h biofilms (approximately 2 log10 reduction). Compound-loaded mesh showed dosage-dependent biofilm-removing capability. In addition, compound 1 displayed a significant inhibitory effect on tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6) secretion from BMDM cells, but interleukin-1 beta (IL-1β) secretion was not significant. The compound was not cytotoxic to BMDM cells at concentrations effective in removing biofilm and lowering cytokine release. These findings highlight the potential of this serrulatane diterpenoid to be further developed for applications in wound management. PMID:26636180

  15. Distribution and carbon isotope patterns of diterpenoids and triterpenoids in modern temperate C3 trees and their geochemical significance

    NASA Astrophysics Data System (ADS)

    Diefendorf, Aaron F.; Freeman, Katherine H.; Wing, Scott L.

    2012-05-01

    Tricyclic diterpenoids and pentacyclic triterpenoids are nearly exclusively produced by gymnosperms and angiosperms, respectively. Even though both classes of terpenoids have long been recognized as plant biomarkers, their potential use as phylogenetically specific δ13C proxies remains largely unexplored. Little is known of how terpenoid abundance and carbon isotope composition vary either with plant phylogenetic position, functional group, or during synthesis. Here, we report terpenoid abundances and isotopic data for 44 tree species in 21 families, representing both angiosperms and gymnosperms, and both deciduous and evergreen leaf habits. Di- and triterpenoid abundances are significantly higher in evergreens compared to deciduous species, reflecting differences in growth strategies and increased chemical investment in longer-lived leaves. Carbon isotope abundances of terpenoid lipids are similar to leaf tissues, indicating biosynthetic isotope effects are small for both the MVA (-0.4‰) and MEP (-0.6‰) pathways. Leaf and molecular isotopic patterns for modern plants are consistent with observations of amber, resins and plant biomarkers in ancient sediments. The δ13C values of ancient diterpenoids are higher than triterpenoids by 2-5‰, consistent with observed isotopic differences between gymnosperms and angiosperms leaves, and support the relatively small lipid biosynthetic effects reported here. All other factors being equal, evergreen plants will dominate the abundance of terpenoids contributed to soils, sediments and ancient archives, with similar inputs estimated for angiosperm and gymnosperm trees when scaled by litter flux.

  16. Serrulatane Diterpenoid from Eremophila neglecta Exhibits Bacterial Biofilm Dispersion and Inhibits Release of Pro-inflammatory Cytokines from Activated Macrophages.

    PubMed

    Mon, Htwe H; Christo, Susan N; Ndi, Chi P; Jasieniak, Marek; Rickard, Heather; Hayball, John D; Griesser, Hans J; Semple, Susan J

    2015-12-24

    The purpose of this study was to assess the biofilm-removing efficacy and inflammatory activity of a serrulatane diterpenoid, 8-hydroxyserrulat-14-en-19-oic acid (1), isolated from the Australian medicinal plant Eremophila neglecta. Biofilm breakup activity of compound 1 on established Staphylococcus epidermidis and Staphylococcus aureus biofilms was compared to the antiseptic chlorhexidine and antibiotic levofloxacin. In a time-course study, 1 was deposited onto polypropylene mesh to mimic a wound dressing and tested for biofilm removal. The ex-vivo cytotoxicity and effect on lipopolysaccharide-induced pro-inflammatory cytokine release were studied in mouse primary bone-marrow-derived macrophage (BMDM) cells. Compound 1 was effective in dispersing 12 h pre-established biofilms with a 7 log10 reduction of viable bacterial cell counts, but was less active against 24 h biofilms (approximately 2 log10 reduction). Compound-loaded mesh showed dosage-dependent biofilm-removing capability. In addition, compound 1 displayed a significant inhibitory effect on tumor necrosis factor alpha (TNF-α) and interleukin-6 (IL-6) secretion from BMDM cells, but interleukin-1 beta (IL-1β) secretion was not significant. The compound was not cytotoxic to BMDM cells at concentrations effective in removing biofilm and lowering cytokine release. These findings highlight the potential of this serrulatane diterpenoid to be further developed for applications in wound management.

  17. Recombination of diterpenoid structure units: synthesis of antitumor amides bearing functionalized bicyclo[3.2.1]octane ring.

    PubMed

    Mao, Zewei; Li, Yan; Chen, Jingbo; Wang, Yuanyuan; Zhang, Hongbin

    2010-07-15

    In this work, 23 new amides (14-36) bearing a representative diterpenoid structure unit, the functionalized bicyclo[3.2.1]octane ring, have been synthesized and its antitumor potential is studied. In vitro studies demonstrate that a number of amides with the bicyclo[3.2.1]oct-3-en-2-one subunit are active against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 tumor cell lines. The hybrid derivative, compound 20, was found to be the most potent compound (IC(50)=1.05 microM against HL-60) and more active than cisplatin (DDP), the positive control. Additionally, compound 20 exhibited broad spectrum in vitro anticancer activity with IC(50) values of 1.1-4.3 microM against the five tested cancer cell lines. PMID:20621726

  18. Isolation and absolute configuration of ent-Halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest.

    PubMed

    Abdel-Kader, Maged; Berger, John M; Slebodnick, Carla; Hoch, Jeannine; Malone, Stan; Wisse, Jan H; Werkhoven, Marga C M; Mamber, Steven; Kingston, David G I

    2002-01-01

    Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.

  19. Recombination of diterpenoid structure units: synthesis of antitumor amides bearing functionalized bicyclo[3.2.1]octane ring.

    PubMed

    Mao, Zewei; Li, Yan; Chen, Jingbo; Wang, Yuanyuan; Zhang, Hongbin

    2010-07-15

    In this work, 23 new amides (14-36) bearing a representative diterpenoid structure unit, the functionalized bicyclo[3.2.1]octane ring, have been synthesized and its antitumor potential is studied. In vitro studies demonstrate that a number of amides with the bicyclo[3.2.1]oct-3-en-2-one subunit are active against HL-60, SMMC-7721, A-549, SK-BR-3, and PANC-1 tumor cell lines. The hybrid derivative, compound 20, was found to be the most potent compound (IC(50)=1.05 microM against HL-60) and more active than cisplatin (DDP), the positive control. Additionally, compound 20 exhibited broad spectrum in vitro anticancer activity with IC(50) values of 1.1-4.3 microM against the five tested cancer cell lines.

  20. Cassane-type diterpenoids from Caesalpinia echinata (Leguminosae) and their NF-κB signaling inhibition activities.

    PubMed

    Mitsui, Taichi; Ishihara, Risa; Hayashi, Ken-ichiro; Matsuura, Nobuyasu; Akashi, Haruo; Nozaki, Hiroshi

    2015-08-01

    Fourteen cassane-type diterpenoids, echinalides H-U, were isolated from the stem of Caesalpinia echinata Lam. (Leguminosae). The structures of the echinalides were elucidated by spectroscopic investigation, including 2D NMR spectroscopic analysis. The structures of echinalide H and echinalide T were further confirmed by single-crystal X-ray diffraction. The absolute configurations of echinalides H, I, J and K were determined by CD spectroscopy. Additionally, the absolute configurations of echinalide L and M were determined by chemical conversion from echinalide H. These compounds were evaluated for inhibitory activity against nuclear factor κB (NF-κB). Echinalide M showed the most potent inhibitory activity (47±11% at 5μM) toward NF-κB-responsive gene expression.

  1. Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms.

    PubMed

    Bozov, Petko; Girova, Tania; Prisadova, Natalia; Hristova, Yana; Gochev, Velizar

    2015-11-01

    Antimicrobial activity of nineteen neo-clerodane diterpenoids, isolated from the acetone extracts of the aerial parts of Scutellaria and Salvia species (Lamiaceae) were tested against thirteen strains belonging to nine different species of pathogenic and food spoilage bacteria Aeromonas hydrophila, Bacillus cereus, Escherichia coli, Listeria monocytogenes, Proteus vulgaris, Pseudomonas aeruginosa, Pseudomonas fluorescens, Salmonella abony and Staphylococcus aureus as well as against two yeast strains belonging to species Candida albicans. Seven of the evaluated compounds scutalpin A, scutalpin E, scutalpin F, salviarin, splenolide A, splenolide B and splendidin demonstrated antimicrobial activity against used test microbial strains, the rest of the compounds were inactive within the studied concentration range. Among all of the tested compounds the highest antimicrobial activity was detected for scutalpin A against Staphylococcus aureus (MIC 25 µg/mL).

  2. Antimicrobial Activity of neo-Clerodane Diterpenoids isolated from Lamiaceae Species against Pathogenic and Food Spoilage Microorganisms.

    PubMed

    Bozov, Petko; Girova, Tania; Prisadova, Natalia; Hristova, Yana; Gochev, Velizar

    2015-11-01

    Antimicrobial activity of nineteen neo-clerodane diterpenoids, isolated from the acetone extracts of the aerial parts of Scutellaria and Salvia species (Lamiaceae) were tested against thirteen strains belonging to nine different species of pathogenic and food spoilage bacteria Aeromonas hydrophila, Bacillus cereus, Escherichia coli, Listeria monocytogenes, Proteus vulgaris, Pseudomonas aeruginosa, Pseudomonas fluorescens, Salmonella abony and Staphylococcus aureus as well as against two yeast strains belonging to species Candida albicans. Seven of the evaluated compounds scutalpin A, scutalpin E, scutalpin F, salviarin, splenolide A, splenolide B and splendidin demonstrated antimicrobial activity against used test microbial strains, the rest of the compounds were inactive within the studied concentration range. Among all of the tested compounds the highest antimicrobial activity was detected for scutalpin A against Staphylococcus aureus (MIC 25 µg/mL). PMID:26749799

  3. Cembrane diterpenoids from the soft coral Sarcophyton trocheliophorum Marenzeller as a new class of PTP1B inhibitors.

    PubMed

    Liang, Lin-Fu; Gao, Li-Xin; Li, Jia; Taglialatela-Scafati, Orazio; Guo, Yue-Wei

    2013-09-01

    A detailed investigation of the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller yielded, along with six known terpenes (6-11), the new sarcophytonolides N-R (1-5), whose structures have been elucidated by detailed spectroscopic analysis. Sarcophytonolides N-R are mono- or bicyclic cembranoids characterized by the presence of three/four double bonds and oxidized methyl groups. Some of the isolated compounds showed significant inhibitory activity against human protein tyrosine phosphatase 1B (PTP1B) enzyme, a key target for the treatment of type-II diabetes and obesity, and some preliminary structure-activity relationships have been drawn. This is the first report on the anti-PTP1B activity of cembrane diterpenoids.

  4. Higginsianins A and B, Two Diterpenoid α-Pyrones Produced by Colletotrichum higginsianum, with in Vitro Cytostatic Activity.

    PubMed

    Cimmino, Alessio; Mathieu, Veronique; Masi, Marco; Baroncelli, Riccardo; Boari, Angela; Pescitelli, Gennaro; Ferderin, Marlène; Lisy, Romana; Evidente, Marco; Tuzi, Angela; Zonno, Maria Chiara; Kornienko, Alexander; Kiss, Robert; Evidente, Antonio

    2016-01-22

    Two new diterpenoid α-pyrones, named higginsianins A (1) and B (2), were isolated from the mycelium of the fungus Colletotrichum higginsianum grown in liquid culture. They were characterized as 3-[5a,9b-dimethyl-7-methylene-2-(2-methylpropenyl)dodecahydronaphtho[2,1-b]furan-6-ylmethyl]-4-hydroxy-5,6-dimethylpyran-2-one and 4-hydroxy-3-[6-hydroxy-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)decahydronaphthalen-1-ylmethyl]-5,6-dimethylpyran-2-one, respectively, by using NMR, HRESIMS, and chemical methods. The structure and relative configuration of higginsianin A (1) were confirmed by X-ray diffractometric analysis, while its absolute configuration was assigned by electronic circular dichroism (ECD) experiments and calculations using a solid-state ECD/TDDFT method. The relative and absolute configuration of higginsianin B (2), which did not afford crystals suitable for X-ray analysis, were determined by NMR analysis and by ECD in comparison with higginsianin A. 1 and 2 were the C-8 epimers of subglutinol A and diterpenoid BR-050, respectively. The evaluation of 1 and 2 for antiproliferative activity against a panel of six cancer cell lines revealed that the IC50 values, obtained with cells reported to be sensitive to pro-apoptotic stimuli, are by more than 1 order of magnitude lower than their apoptosis-resistant counterparts (1 vs >80 μM). Finally, three hemisynthetic derivatives of 1 were prepared and evaluated for antiproliferative activity. Two of these possessed IC50 values and differential sensitivity profiles similar to those of 1. PMID:26697898

  5. A Cytochrome P450-Mediated Intramolecular Carbon-Carbon Ring Closure in the Biosynthesis of Multidrug-Resistance-Reversing Lathyrane Diterpenoids.

    PubMed

    King, Andrew J; Brown, Geoffrey D; Gilday, Alison D; Forestier, Edith; Larson, Tony R; Graham, Ian A

    2016-09-01

    The Euphorbiaceae produce a wide variety of bioactive diterpenoids. These include the lathyranes, which have received much interest due to their ability to inhibit the ABC transporters responsible for the loss of efficacy of many chemotherapy drugs. The lathyranes are also intermediates in the biosynthesis of range of other bioactive diterpenoids with potential applications in the treatment of pain, HIV and cancer. We report here a gene cluster from Jatropha curcas that contains the genes required to convert geranylgeranyl pyrophosphate into a number of diterpenoids, including the lathyranes jolkinol C and epi-jolkinol C. The conversion of casbene to the lathyranes involves an intramolecular carbon-carbon ring closure. This requires the activity of two cytochrome P450s that we propose form a 6-hydroxy-5,9-diketocasbene intermediate, which then undergoes an aldol reaction. The discovery of the P450 genes required to convert casbene to lathyranes will allow the scalable heterologous production of these potential anticancer drugs, which can often only be sourced in limited quantities from their native plant. PMID:27272333

  6. Structure elucidation of organic compounds from natural sources using 1D and 2D NMR techniques

    NASA Astrophysics Data System (ADS)

    Topcu, Gulacti; Ulubelen, Ayhan

    2007-05-01

    In our continuing studies on Lamiaceae family plants including Salvia, Teucrium, Ajuga, Sideritis, Nepeta and Lavandula growing in Anatolia, many terpenoids, consisting of over 50 distinct triterpenoids and steroids, and over 200 diterpenoids, several sesterterpenoids and sesquiterpenoids along with many flavonoids and other phenolic compounds have been isolated. For Salvia species abietanes, for Teucrium and Ajuga species neo-clerodanes for Sideritis species ent-kaurane diterpenes are characteristic while nepetalactones are specific for Nepeta species. In this review article, only some interesting and different type of skeleton having constituents, namely rearranged, nor- or rare diterpenes, isolated from these species will be presented. For structure elucidation of these natural diterpenoids intensive one- and two-dimensional NMR techniques ( 1H, 13C, APT, DEPT, NOE/NOESY, 1H- 1H COSY, HETCOR, COLOC, HMQC/HSQC, HMBC, SINEPT) were used besides mass and some other spectroscopic methods.

  7. ent-kaurane diterpenoids from Croton tonkinensis induce apoptosis in colorectal cancer cells through the phosphorylation of JNK mediated by reactive oxygen species and dual-specificity JNK kinase MKK4.

    PubMed

    Thuong, Phuong Thien; Khoi, Nguyen Minh; Ohta, Saho; Shiota, Shinichiro; Kanta, Hironori; Takeuchi, Kenji; Ito, Fumiaki

    2014-01-01

    To search for new chemotherapeutic agents to treat colorectal cancer, we isolated a number of natural ent-kaurane diterpenoids from the plant Croton tonkinensis. Among them, only CeKDs with the 15-oxo-16-ene moiety induced the apoptosis of colorectal cancer cell lines Caco-2 and LS180. The active CeKD induced the activation of ERK and JNK, but the inactive ones induced that of ERK, but not that of JNK. It thus appears that JNK seemed to play an important role in the apoptotic activity of the active compounds. The dualspecificity JNK kinase MKK4 was activated in both colorectal cancer cells treated with the active CeKD, but MKK7 was not activated. Further, the active CeKD, but not the inactive one, enhanced the generation of intracellular reactive oxygen species (ROS) in both cells. CeKD-induced cell apoptosis and ROS generation, as well as JNK activation, were inhibited by the antioxidant N-acetyl-L-cysteine. These findings suggest that ROS stimulated the phosphorylation of JNK mediated by MKK4 and played a critical role in CeKD-induced apoptosis in colorectal cancer cells.

  8. Bioactive-guided identification of labdane diterpenoids from aerial parts of Aristeguietia glutinosa as anti-Trypanosoma cruzi agents.

    PubMed

    Varela, Javier; Lavaggi, María L; Cabrera, Mauricio; Rodríguez, Alejandra; Miño, Patricio; Chiriboga, Ximena; Cerecetto, Hugo; González, Mercedes

    2012-09-01

    A bioactive-guided investigation of the hydro-ethanolic extract of aerial parts of Aristeguietia glutinosa Lam. resulted in the isolation of two diterpenoids, (+)-15-hydroxy-labd-7-en-17-al (1) and (+)-13,14,15,16-tetranor-labd-7-en-17,12-olide (2), as the anti-Trypanosoma cruzi active principles. The structures of 1 and 2 were determined by spectroscopic analysis. The hydro-ethanolic extract showed anti-T. cruzi activity (IC50 = 19.6 microg/mL) whereas the isolated compounds 1 and 2 were near to seven- and one and a half-fold (IC50 = 3.0 and 15.6 microg/mL), respectively more active than the original extract. Labdene 1, equipotent as the reference compound (Nifurtimox), displayed low hemolytic activity, low toxicity against murine macrophages, and absence of mutagenicity. These results support the vernacular medicinal use of this plant as an anti-T. cruzi agent. PMID:23074890

  9. Inhibition of caspase-9 by oridonin, a diterpenoid isolated from Rabdosia rubescens, augments apoptosis in human laryngeal cancer cells

    PubMed Central

    KANG, NING; CAO, SHI-JIE; ZHOU, YAN; HE, HAO; TASHIRO, SHIN-ICHI; ONODERA, SATOSHI; QIU, FENG; IKEJIMA, TAKASHI

    2015-01-01

    Rabdosia rubescens, a commonly used traditional Chinese medicine, has increasingly gained attention for its use as an antitumor herb. Oridonin, a bioactive diterpenoid isolated from Rabdosia rubescens, has been reported to induce apoptosis in human laryngeal cancer HEp-2 cells by our group. Here, we made unexpected observations that the caspase-9 inhibitor (C9i) enhanced apoptosis in response to selected stimuli, and HEp-2 cells which were made deficient in caspase-9 using siRNA exhibited no resistance to apoptotic signals and actually demonstrated increased apoptotic sensitivity to oridonin. The results were reversed by the transfection of an exogenous caspase-9 expression vector. Caspase-9 reduced sensitivity to apoptotic stimuli through reactive oxygen species (ROS)-suppressing and autophagy-promoting methods. ROS triggered the progression of apoptosis through activation of both the caspase-9-independent mitochondrial pathway and death receptor pathways, and the autophagy had an anti-apoptotic function in oridonin-treated HEp-2 cells. These collective results suggest that oridonin targets caspase-9 to alter ROS production and autophagy situation to promote HEp-2 cell apoptosis. Therefore, oridonin has the potential to be developed as an anticancer agent, and the combination of oridonin with those agents leading to reduction of caspase-9 expression in tumor cells could represent a novel approach to human laryngeal cancer treatment. PMID:26648189

  10. Six new cytotoxic and anti-inflammatory 11, 20-epoxy-ent-kaurane diterpenoids from Isodon wikstroemioides.

    PubMed

    Wu, Hai-Yan; Wang, Wei-Guang; Du, Xue; Yang, Jin; Pu, Jian-Xin; Sun, Han-Dong

    2015-05-01

    The present study was designed to determine the chemical constituents of EtOAc extracts of the aerial parts of Isodon wikstroemioides. Compounds 1-8 were isolated and purified by normal-phase silica gel and reversed-phase C18silica gel column chromatography and HPLC. Their structures were elucidated by extensive spectroscopic methods. Most of them were evaluated for their in vitro cytotoxicity against human cancer HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cells and their inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages. Among the eight 11, 20-epoxy-ent-kauranoids isolated, compounds 1-6 (isowikstroemins H-M) were new diterpenoids. Compounds 1, 3, and 7 exhibited significant cytotoxicity with IC50 values ranging from (0.84 ± 0.02) to (4.09 ± 0.34) μmol · L(-1), while compounds 4 and 5 showed selective cytotoxicity. In addition, compounds 1, 3, 4, and 7 exhibited inhibitory activity against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages. These results provide a basis for future development of these compounds as anti-cancer and anti-inflammatory agents. PMID:25986288

  11. Phytochemical profiling of Curcuma kwangsiensis rhizome extract, and identification of labdane diterpenoids as positive GABAA receptor modulators.

    PubMed

    Schramm, Anja; Ebrahimi, Samad Nejad; Raith, Melanie; Zaugg, Janine; Rueda, Diana C; Hering, Steffen; Hamburger, Matthias

    2013-12-01

    An ethyl acetate extract of Curcuma kwangsiensis S.G. Lee & C.F. Liang (Zingiberaceae) rhizomes (100 μg/ml) enhanced the GABA-induced chloride current (IGABA) through GABAA receptors of the α1β2γ2S subtype by 79.0±7.0%. Potentiation of IGABA was measured using the two-microelectrode voltage-clamp technique and Xenopus laevis oocytes. HPLC-based activity profiling of the crude extract led to the identification of 11 structurally related labdane diterpenoids, including four new compounds. Structure elucidation was achieved by comprehensive analysis of on-line (LC-PDA-ESI-TOF-MS) and off-line (microprobe 1D and 2D NMR) spectroscopic data. The absolute configuration of the compounds was established by comparison of experimental and calculated ECD spectra. Labdane diterpenes represent a new class of plant secondary metabolites eliciting positive GABAA receptor modulation. The highest efficiency was observed for zerumin A (maximum potentiation of IGABA by 309.4±35.6%, and EC50 of 24.9±8.8 μM).

  12. NO-Releasing Enmein-Type Diterpenoid Derivatives with Selective Antiproliferative Activity and Effects on Apoptosis-Related Proteins.

    PubMed

    Li, Dahong; Hu, Xu; Han, Tong; Liao, Jie; Xiao, Wei; Xu, Shengtao; Li, Zhanlin; Wang, Zhenzhong; Hua, Huiming; Xu, Jinyi

    2016-01-01

    A series of nine enmein-type ent-kaurane diterpenoid and furoxan-based nitric oxide (NO) donor hybrids (10a-i) were designed and synthesized from commercially available oridonin (1). These hybrids were evaluated for their antiproliferative activity against Bel-7402, K562, MGC-803, and CaEs-17 human cancer cell lines and L-02 normal liver cells. The antiproliferative activity against tumor cells was stronger than the lead compound 1 and parent molecule 9 in most cases. Especially, compound 10f showed the strongest activity against human hepatocarcinoma Bel-7402 cell line with an IC50 of 0.81 μM and could also release 33.7 μmol/L NO at the time point of 60 min. Compounds 10a-i also showed cytotoxic selectivity between tumor and normal liver cells with IC50 ranging from 22.1 to 33.9 μM. Furthermore, the apoptotic properties on Bel-7402 cells revealed that 10f could induce S phase cell cycle arrest and apoptosis at low micromolar concentrations. The effects of 10f on apoptosis-related proteins were also investigated. The potent antiproliferative activities and mechanistic studies warrant further preclinical investigations. PMID:27617998

  13. Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest.

    PubMed

    Sai Prakash, Chaturvedula V; Hoch, Jeannine M; Kingston, David G I

    2002-02-01

    Bioassay-guided fractionation of a CH(2)Cl(2)/MeOH extract of the bark of Casearia lucida resulted in the isolation of 11 new clerodane diterpenes, namely, casearlucins A-K (1-11), and three known clerodane diterpenoids, rel-(2S,5R,6R,8S,9S,10R,18S,19R)-diacetoxy-18,19-epoxy-6-hydroxy-2-(2xi-methylbutanoyloxy)cleroda-3,13(16),14-triene (12), rel-(2S,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-methoxy-2-(2xi-methylbutanoyloxy)cleroda-3,13(16),14-triene (13), and rel-(2S,5R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-2-(2xi-methylbutanoyloxy)cleroda-3,13(16),14-triene (14). The structures of compounds 1-11 were established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. All compounds exhibited cytotoxicity activity against the A2780 ovarian cancer cell line, but none of the six compounds selected for testing in multiple cell lines showed significant selectivity.

  14. Natural compounds in the synthesis of chiral organophosphorous ligands

    NASA Astrophysics Data System (ADS)

    Tolstikov, Alexander G.; Khlebnikova, Tatiana B.; Tolstikova, Olga V.; Tolstikov, Genrikh A.

    2003-09-01

    Methods for the synthesis of chiral organophosphorus compounds based on natural optically active compounds (hydroxy acids, amino acids and their derivatives, mono- and disaccharides, mono- and diterpenoids, steroids) are discussed. Particular attention is given to the synthesis of bisphosphines and bisphosphinites. These compounds serve as ligands for transition metal complexes, which catalyse asymmetric hydrogenation. Data on the enantioselectivity of hydrogenation of unsaturated precursors of amino acids and unsaturated prochiral acids as well as on information on the enantioselectivity of hydrosilylation of ketones are surveyed.

  15. Simultaneous determination of seven major diterpenoids in Siegesbeckia pubescens Makino by high-performance liquid chromatography coupled with evaporative light scattering detection.

    PubMed

    Huo, Linan; Jiang, Zhen; Li, Huining; Wang, Mingsheng; Ye, Xiaoxia; Ji, Bin; Guo, Xingjie

    2012-10-01

    A novel HPLC method with evaporative light scattering detection was developed for the simultaneous quantification of seven major diterpenoids of two types, including ent-pimarane type: Kirenol, Hythiemoside B, Darutigenol, and ent-kaurane type: ent-16β,17,18-trihydroxy-kauran-19-oic acid, ent-17,18-dihydroxy-kauran-19-oic acid, ent-16β,17-dihydroxy-kauran-19-oic acid, 16α-hydro-ent-kauran-17,19-dioic acid in the aerial parts of Siegesbeckia pubescens Makino, an important traditional Chinese medicinal herb. Chromatographic separation was achieved on a Waters Symmetry Shield(TM) RP18 column (250 mm× 4.6 mm id, 5 μm) with a gradient mobile phase (A: 0.3% v/v aqueous formic acid and B: acetonitrile) at a flow rate of 1.0 mL/min. The drift tube temperature of evaporative light scattering detection was set at 103°C, and nitrogen flow rate was 3.0 L/min. The method was validated for accuracy, precision, LOD, and LOQ. All calibration curves showed a good linear relationship (r > 0.999) in test range. Precision was evaluated by intra- and interday tests that showed RSDs were less than 3.5%. Accuracy validation showed that the recovery was between 96.5 and 102.0% with RSDs below 2.8%. The validated method was successfully applied to determine the contents of seven diterpenoids in the different parts of Siegesbeckia pubescens Makino from two sources and to determine the contents of ent-pimarane, ent-kaurane, and total diterpenoids. PMID:22887919

  16. Overexpression of the bZIP transcription factor OsbZIP79 suppresses the production of diterpenoid phytoalexin in rice cells.

    PubMed

    Miyamoto, Koji; Nishizawa, Yoko; Minami, Eiichi; Nojiri, Hideaki; Yamane, Hisakazu; Okada, Kazunori

    2015-01-15

    Phytoalexins are antimicrobial specialised metabolites that are produced by plants in response to pathogen attack. Momilactones and phytocassanes are major diterpenoid phytoalexins in rice that are synthesised from geranylgeranyl diphosphate that is derived from the methylerythritol phosphate (MEP) pathway. We have previously reported that rice cells overexpressing the basic leucine zipper (bZIP) transcription factor OsTGAP1 exhibit a hyperaccumulation of momilactones and phytocassanes, with hyperinductive expression of momilactone and phytocassane biosynthetic genes and MEP pathway genes, upon response to a chitin oligosaccharide elicitor. For a better understanding of OsTGAP1-mediated regulation of diterpenoid phytoalexin production, we identified OsTGAP1-interacting proteins using yeast two-hybrid screening. Among the OsTGAP1-interacting protein candidates, a TGA factor OsbZIP79 was investigated to verify its physical interaction with OsTGAP1 and involvement in the regulation of phytoalexin production. An in vitro pull-down assay demonstrated that OsTGAP1 and OsbZIP79 exhibited a heterodimeric as well as a homodimeric interaction. A bimolecular fluorescence complementation analysis also showed the interaction between OsTGAP1 and OsbZIP79 in vivo. Intriguingly, whereas OsbZIP79 transactivation activity was observed in a transient reporter assay, the overexpression of OsbZIP79 resulted in suppression of the elicitor-inducible expression of diterpenoid phytoalexin biosynthetic genes, and thus caused a decrease in the accumulation of phytoalexin in rice cells. These results suggest that OsbZIP79 functions as a negative regulator of phytoalexin production triggered by a chitin oligosaccharide elicitor in rice cells, although it remains open under which conditions OsbZIP79 can work with OsTGAP1.

  17. Kaurane-type diterpenoids from Chromoleana odorata, their X-ray diffraction studies and potent α-glucosidase inhibition of 16-kauren-19-oic acid.

    PubMed

    Wafo, Pascal; Kamdem, Ramsay S T; Ali, Zulfiqar; Anjum, Shazia; Begum, Afshan; Oluyemisi, Ogbole O; Khan, Shamsun N; Ngadjui, Bonaventure T; Etoa, Xavier F; Choudhary, Muhammed Iqbal

    2011-06-01

    A new diterpenoid, 15-angeloyloxy-16,17-epoxy-19-kauronic acid (1), along with five known metabolites, 16-kauren-19-oic acid (2), 6'-hydroxy-2',3',4,4'-tetramethoxychalcone (3), isosakuranetin (4), acacetin (5), and kaempferide (6) was isolated from the organic extracts of the roots of Chromoleana odorata. Their structures were determined by spectroscopic evidences. The structures of 1 and 2 were further confirmed by single-crystal X-ray diffraction studies. Compound 2 exhibited significant α-glucosidase inhibitory and antibacterial activities against Escherichia coli and Bacillus subtilis.

  18. Synthetic studies of neoclerodane diterpenoids from Salvia splendens and evaluation of Opioid Receptor affinity

    PubMed Central

    Fontana, Gianfranco; Savona, Giuseppe; Rodríguez, Benjamín; Dersch, Christina M.; Rothman, Richard B.; Prisinzano, Thomas E.

    2009-01-01

    Salvinorin A (1), a neoclerodane diterpene from the hallucinogenic mint Salvia divinorum, is the only known non-nitrogenous and specific κ-opioid agonist. Several structural congeners of 1 isolated from Salvia splendens (2 – 8) together with a series of semisynthetic derivatives (9 – 24), some of which possess a pyrazoline structural moiety (9, 19 – 22), have been tested for affinity at human μ, δ, and κ opioid receptors. None of these compounds showed high affinity binding to these receptors. However, 10 showed modest affinity for κ receptors suggesting other naturally neoclerodanes from different Salvia species may possess opioid affinity. PMID:20027203

  19. Comparison of oil-in-water and water-in-oil microemulsion electrokinetic chromatography as methods for the analysis of eight phenolic acids and five diterpenoids.

    PubMed

    Cao, Jun; Chen, Jun; Yi, Ling; Li, Ping; Qi, Lian-Wen

    2008-06-01

    Oil-in-water (O/W) and water-in-oil (W/O) MEEKC were compared for their abilities to separate and detect eight phenolic acids and five diterpenoids in Radix et Rhizoma Salviae Miltiorrhizae (RRSM). The effects of oil type and concentration, organic modifier, SDS, and buffer concentration on separation were examined in order to optimize the two methods. Oil contents and organic modifier were found to markedly influence the separation selectivity for both O/W and W/O systems. SDS concentration rarely affected separation resolution for O/W MEEKC, and separation of eight phenolic acids and five diterpenoids could be improved by changing the buffer concentration for W/O MEEKC. A highly efficient O/W MEEKC separation method, where the 13 compounds were separated with baseline resolution, was achieved by using a microemulsion solution of pH 8.0 containing 0.6% cyclohexane, 3.0% SDS, 6.0% 1-butanol, and 3.0% ACN. The W/O MEEKC was unable to resolve all the components. In addition, the analytic time in O/W MEEKC was shorter than that in W/O MEEKC. Finally, the developed O/W MEEKC method was successfully applied to determine analytic compounds in RRSM samples. PMID:18435496

  20. Henryin, an ent-kaurane Diterpenoid, Inhibits Wnt Signaling through Interference with β-Catenin/TCF4 Interaction in Colorectal Cancer Cells

    PubMed Central

    Li, Xingyao; Pu, Jianxin; Jiang, Shiyou; Su, Jia; Kong, Lingmei; Mao, Bingyu; Sun, Handong; Li, Yan

    2013-01-01

    Aberrant Wnt/β-catenin signaling has been strongly associated with the tumorigenesis of human colorectal cancer. Inhibitors of this pathway may then offer therapeutic strategies as well as chemoprevention for this malignant disease. Henryin is an ent-kaurane diterpenoid isolated from Isodonrubescens var. lushanensis, a plant long been used in folk medicine to prevent inflammation and gastrointestinal disease. In the present study, we report that henryin selectively inhibits the proliferation of human colorectal cancer cells with a GI50 value in the nano-molar range. Microarray analysis and reporter assays showed that henryin worked as a novel antagonist of Wnt signaling pathway. Henryin reduced the expression of Cyclin D1 and C-myc, and induced G1/S phase arrest in HCT116 cells. Concurrently, henryin did not affect the cytosol-nuclear distribution of soluble β-catenin, but impaired the association of β-catenin/TCF4 transcriptional complex likely through directly blocking the binding of β-catenin to TCF4. We also then analyzed the structure-activity relationship among the ent-kaurane type diterpenoids. Our data suggests that henryin, as a novel inhibitor of Wnt signaling, could be a potential candidate for further preclinical evaluation for colon cancer treatment, and as such warrants further exploration. PMID:23844215

  1. Extraction of three bioactive diterpenoids from Andrographis paniculata: effect of the extraction techniques on extract composition and quantification of three andrographolides using high-performance liquid chromatography.

    PubMed

    Kumar, Satyanshu; Dhanani, Tushar; Shah, Sonal

    2014-10-01

    Andrographis paniculata (Burm.f.) wall.ex Nees (Acanthaceae) or Kalmegh is an important medicinal plant finding uses in many Ayurvedic formulations. Diterpenoid compounds andrographolides (APs) are the main bioactive phytochemicals present in leaves and herbage of A. paniculata. The efficiency of supercritical fluid extraction (SFE) using carbon dioxide was compared with the solid-liquid extraction techniques such as solvent extraction, ultrasound-assisted solvent extraction and microwave-assisted solvent extraction with methanol, water and methanol-water as solvents. Also a rapid and validated reverse-phase high-performance liquid chromatography-diode array detection method was developed for the simultaneous determination of the three biologically active compounds, AP, neoandrographolide and andrograpanin, in the extracts of A. paniculata. Under the best SFE conditions tested for diterpenoids, which involved extraction at 60°C and 100 bar, the extractive efficiencies were 132 and 22 µg/g for AP and neoandrographolide, respectively. The modifier percentage significantly affected the extraction efficiency.

  2. Synthesis of novel diterpenoid analogs with in-vivo antitumor activity.

    PubMed

    Wang, Ying-Ying; He, Yuan; Yang, Lian-Fang; Peng, Shi-Hong; He, Xiao-Long; Wang, Jin-Hua; Lv, Fang; Hao, Yun; Liu, Ming-Yao; Yi, Zhengfang; Qiu, Wen-Wei

    2016-09-14

    A lead compound 7 has antitumor effect, which was discovered by screening our small synthetic natural product-like compound (NPL) library. Based on the lead compound, a series of novel tricyclic diterpene analogs were synthesized and investigated for their activity against the growth of various tumor cell lines using the sulforhodamine B (SRB) assay. To our delight, most aromatic amide compounds exhibited more potent antitumor activity than the lead compound. The most active compound 19 (QW30) showed an average IC50 0.33 μM, which was 15-fold more potent than the lead compound. Most of the compounds with potent antitumor activity displayed less toxic on normal human fibroblasts (HAF) in comparison with the tumor cell lines. Especially 19, its selectivity indexes (SI) between HAF and cancer cell lines was 17.3 times better than the positive control compound podophyllotoxin. The apoptosis, colony formation and transwell migration assays of 7 and 19 were performed on T47D cell line. The in-vivo antitumor effect of 19 was also observed in T47D tumor-bearing mice without obvious toxicity.

  3. Anti-Candida Cassane-Type Diterpenoids from the Root Bark of Swartzia simplex.

    PubMed

    Favre-Godal, Quentin; Dorsaz, Stephane; Queiroz, Emerson F; Marcourt, Laurence; Ebrahimi, Samad N; Allard, Pierre-Marie; Voinesco, Francine; Hamburger, Matthias; Gupta, Mahabir P; Gindro, Katia; Sanglard, Dominique; Wolfender, Jean-Luc

    2015-12-24

    A dichloromethane extract of the roots from the Panamanian plant Swartzia simplex exhibited a strong antifungal activity in a bioautography assay against a genetically modified hypersusceptible strain of Candida albicans. At-line HPLC activity based profiling of the crude extract enabled a precise localization of the antifungal compounds, and dereplication by UHPLC-HRESIMS indicated the presence of potentially new metabolites. Transposition of the HPLC reversed-phase analytical conditions to medium-pressure liquid chromatography (MPLC) allowed an efficient isolation of the major constituents. Minor compounds of interest were isolated from the MPLC fractions using semipreparative HPLC. Using this strategy, 14 diterpenes (1-14) were isolated, with seven (5-10, 14) being new antifungal natural products. The new structures were elucidated using NMR spectroscopy and HRESIMS analysis. The absolute configurations of some of the compounds were elucidated by electronic circular dichroism spectroscopy. The antifungal properties of these compounds were evaluated as their minimum inhibitory concentrations in a dilution assay against both hypersusceptible and wild-type strains of C. albicans and by assessment of their antibiofilm activities. The potential cytological effects on the ultrastructure of C. albicans of the antifungal compounds isolated were evaluated on thin sections by transmission electron microscopy. PMID:26654828

  4. Differentiation of Isodon japonica and Adulterants Based on Identification and Quantitation 14 Diterpenoids Using LC-MS-MS Library Search Approach and Hierarchical Cluster Analysis.

    PubMed

    Jin, Yiran; Tian, Tingting; Ma, Yinghua; Liu, Minyan; Xie, Weiwei; Wang, Xin; Xu, Huijun; Du, Yingfeng

    2016-03-01

    The aim of this study was to investigate the chemical differences between genunine Isodon japonica and its adulterants. A linear ion trap liquid chromatography with tandem mass spectrometry analytical method has been developed for the identification and quantification of 14 major diterpenoids in I. japonica. Data acquisition was multiple reaction monitoring transitions mode followed by an information-dependent acquisition using the enhanced product ion (EPI) scan in a single run. The target compounds were further identified and confirmed using an EPI spectral library. Overall validation of the assay was carried out including linearity, accuracy, precision, limits of detection and quantification. The results demonstrated that the method was selective, sensitive and reliable. The determination results of 21 batches of I. japonica and adulterants were then analyzed and differentiated by hierarchical clustering analysis. PMID:26489434

  5. Chemical constituents of malagasy liverworts, part V: prenyl bibenzyls and clerodane diterpenoids with nitric oxide inhibitory activity from Radula appressa and Thysananthus spathulistipus.

    PubMed

    Harinantenaina, Liva; Takahara, Yusuke; Nishizawa, Takashi; Kohchi, Chie; Soma, Gen-Ichiro; Asakawa, Yoshinori

    2006-07-01

    3Beta,4beta:15,16-diepoxy-13(16),14-clerodadiene (1) and a new clerodane diterpenoid designated thysaspathone (2) were isolated from the liverwort Thysananthus spathulistipus, while Radula appressa produced radulannin A (3), radulannin L (4), 2-geranyl-3,5-dihydroxybibenzyl (5), 2(S)-2-methyl-2-(4-methyl-3-pentenyl)-7-hydroxy-5-(2-phenylethyl) chromene (o-cannabichromene) (6), 6-hydroxy-4-(2-phenylethyl) benzofuran (7), and o-cannabicyclol (8). All of the isolated compounds inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells and the greatest inhibition was attributed to compound 5, with an IC50 value of 4.5 microM.

  6. Bioactive (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

    PubMed

    Li, Cui; La, Ming-Ping; Sun, Peng; Kurtan, Tibor; Mandi, Attila; Tang, Hua; Liu, Bao-Shu; Yi, Yang-Hua; Li, Ling; Zhang, Wen

    2011-01-01

    Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7-10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.

  7. Seed dormancy breaking diterpenoids from the liverwort Plagiochila sciophila and their differentiation inducing activity in human promyelocytic leukemia HL-60 cells.

    PubMed

    Kenmoku, Hiromichi; Tada, Hiroyuki; Oogushi, Megumi; Esumi, Tomoyuki; Takahashi, Hironobu; Noji, Masaaki; Sassa, Takeshi; Toyota, Masao; Asakawa, Yoshinori

    2014-07-01

    To obtain the structural diversity of bioactive compounds similar to cotylenins and fusicoccins that modulate 14-3-3 protein-protein interactions in eukaryotes, screening tests were carried out using the lettuce seed dormancy breaking-assay. An acetone extract of the liverwort Plagiochila sciophila exhibited significant activity against the seeds in the presence of the plant hormone abscisic acid. Activity-guided fractionation of the extract afforded the isolation of seven novel fusicoccane-type diterpenoids, named fusicosciophins A-E (1-5), 8-deacetyl (6) and 9-deacetyl fusicosciophin E (7). Their structures were determined by spectroscopic methods and X-ray crystallographic analyses. All the pure isolated compounds (1-7) exhibited moderate lettuce seed dormancy breaking activity. In addition, the differentiation-inducing activity and cytotoxicity of these isolates, together with fusicoccin A (FC-A) and all-trans retinoic acid (ATRA), were evaluated in human promyelocytic leukemia HL-60 cells and human mouth epidermal carcinoma KB cells, respectively. Fusicosciophins (2 and 4) and FC-A exhibited moderate differentiation-inducing activity (EC50 31.2-59.1 microM) compared with ATRA (EC50 0.3 microM), while 2, 4 and ATRA exhibited higher selectivity indices (IC50/EC50 >3.38-667) than FC-A (IC50/EC50 1.05). This is the first report on the isolation of fusicoccane-type diterpenoids from liverworts having seed dormancy breaking activity and differentiation-inducing activity in mammal cells. PMID:25230492

  8. Seed dormancy breaking diterpenoids from the liverwort Plagiochila sciophila and their differentiation inducing activity in human promyelocytic leukemia HL-60 cells.

    PubMed

    Kenmoku, Hiromichi; Tada, Hiroyuki; Oogushi, Megumi; Esumi, Tomoyuki; Takahashi, Hironobu; Noji, Masaaki; Sassa, Takeshi; Toyota, Masao; Asakawa, Yoshinori

    2014-07-01

    To obtain the structural diversity of bioactive compounds similar to cotylenins and fusicoccins that modulate 14-3-3 protein-protein interactions in eukaryotes, screening tests were carried out using the lettuce seed dormancy breaking-assay. An acetone extract of the liverwort Plagiochila sciophila exhibited significant activity against the seeds in the presence of the plant hormone abscisic acid. Activity-guided fractionation of the extract afforded the isolation of seven novel fusicoccane-type diterpenoids, named fusicosciophins A-E (1-5), 8-deacetyl (6) and 9-deacetyl fusicosciophin E (7). Their structures were determined by spectroscopic methods and X-ray crystallographic analyses. All the pure isolated compounds (1-7) exhibited moderate lettuce seed dormancy breaking activity. In addition, the differentiation-inducing activity and cytotoxicity of these isolates, together with fusicoccin A (FC-A) and all-trans retinoic acid (ATRA), were evaluated in human promyelocytic leukemia HL-60 cells and human mouth epidermal carcinoma KB cells, respectively. Fusicosciophins (2 and 4) and FC-A exhibited moderate differentiation-inducing activity (EC50 31.2-59.1 microM) compared with ATRA (EC50 0.3 microM), while 2, 4 and ATRA exhibited higher selectivity indices (IC50/EC50 >3.38-667) than FC-A (IC50/EC50 1.05). This is the first report on the isolation of fusicoccane-type diterpenoids from liverworts having seed dormancy breaking activity and differentiation-inducing activity in mammal cells.

  9. Diterpenoids from Casearia sylvestris

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Two highly oxygenated clerodane diterpenes casearins U (1) and V (2) and two ent-kaurane diterpene glucosides sylvestrisides A (3) and B (4) were isolated from the leaves of Casearia sylvestris, together with 13 known compounds. Their structures were established on the basis of 1D and 2D NMR spectro...

  10. Targeting Apoptosis Pathway with Natural Terpenoids: Implications for Treatment of Breast and Prostate Cancer

    PubMed Central

    Yang, Huanjie; Dou, Q. Ping

    2012-01-01

    Terpenoids represent a large and diverse class of naturally occurring compounds found in a variety of fruits, vegetables and medicinal plants. Structurally some of the terpenoids are similar to human hormones. A diet rich in terpenoids is inversely related with the risk of chronic diseases including cancers. Breast and prostate cancers are hormone-related diseases and the second leading cause of female and male cancer mortality. Diterpenoid paclitaxel, and its semi-synthetic analogue docetaxel, have entered clinical use against established breast and prostate cancers. Here we reviewed potential molecular targets and biological properties of natural terpenoids, including monoterpenoids, diterpenoids, triterpenoids and tetraterpenoids, and their applications in treatment of human breast and prostate cancers. These terpenoids are able to inhibit tumor cell proliferation and induce tumor cell death by inhibiting multiple cancer-specific targets including the proteasome, NF-κB, and antiapoptotic protein Bcl-2. The efficacy of these terpenoids against breast or prostate cancer cells, as demonstrated in pre-clinical studies supports clinical application of these naturally occurring terpenoids in treatment of hormone-related human cancers. PMID:20298150

  11. Cytotoxic and natural killer cell stimulatory constituents of Phyllanthus songboiensis

    PubMed Central

    Ren, Yulin; Yuan, Chunhua; Deng, Youcai; Kanagasabai, Ragu; Ninh, Tran Ngoc; Tu, Vuong Tan; Chai, Hee-Byung; Soejarto, Djaja D.; Fuchs, James R.; Yalowich, Jack C.; Yu, Jianhua; Kinghorn, A. Douglas

    2014-01-01

    A dichapetalin-type triterpenoid and a dibenzylbutyrolactone-type lignan, together with five known lignans, a known aromatic diterpenoid, and a known acylated phytosterol, were isolated from the aerial parts of Phyllanthus songboiensis, collected in Vietnam. Their structures were determined by interpretation of the spectroscopic data, and the inhibitory activity toward the HT-29 human colon cancer cells of all isolates was evaluated by a cytotoxicity assay. The known arylnaphthalene lignan, (+)-acutissimalignan A, was highly cytotoxic toward HT-29 cells, with an IC50 value of 19 nM, but this compound was inactive as a DNA topoisomerase IIα (topo IIα) poison. The known phytosterol, (−)-β-sitosterol-3-O-β-D-(6-O-palmitoyl)glucopyranoside, was found to stimulate natural killer (NK) cells at a concentration of 10 μM in the presence of interleukin 12 (IL-12). PMID:25596805

  12. Gastroprotective effects of new diterpenoid derivatives from Azorella cuatrecasasii Mathias & Constance obtained using a β-cyclodextrin complex with microbial and chemical transformations.

    PubMed

    Sepúlveda, Beatriz; Quispe, Cristina; Simirgiotis, Mario; García-Beltrán, Olimpo; Areche, Carlos

    2016-07-15

    Mulinane diterpenoids isolated from Azorella species have displayed gastroprotective effects in animal models. In this study we have transformed the main constituent, mulin-11,13-dien-20 oic acid from this plant using the filamentous fungus Mucor plumbeus and a β-cyclodextrin inclusion complex and we have obtained two main products with good yields (33% and 15% for compound 4 and 5, respectively) for further preparation of semisynthetic derivatives to evaluate their gastroprotective effects. In addition, one of the compounds isolated from Azorella cuatrecasasii was new (9-epi-13α-hydroxymulinene 1). Six new derivatives 4a-4c and 5a-5c were then prepared by simple chemical transformations. The structures of all compounds were elucidated by spectroscopic means based on 1D and 2D-NMR techniques. Some 8 diterpenes were evaluated for their gastroprotective effects in the ethanol/HCl-induced ulcer model in mice at 20mg/kg. The highest gastroprotective activity was shown by 7α,16-dihydroxymulin-11,13-dien-20-oic acid 5, which was higher than the reference drug lansoprazole, while 16-hydroxymulin-11,13-dien-20-oic acid 4 was as active as lansoprazole.

  13. Detection and identification of diterpenoid alkaloids, isoflavonoids and saponins in Qifu decoction and rat plasma by liquid chromatography-time-of-flight mass spectrometry.

    PubMed

    Tan, Guangguo; Jing, Jing; Zhu, Zhenyu; Lou, Ziyang; Li, Wuhong; Zhao, Liang; Zhang, Guoqing; Chai, Yifeng

    2012-02-01

    A liquid chromatography-time-of-flight mass spectrometric (LC-TOFMS) method has been developed for analysis of components in Qifu decoction (QFD), a traditional Chinese medical formula consisting of Radix Astragali and Acontium carmichaeli, and in rat plasma after oral administration. Based on accurate mass measurements within 3 ppm error for each molecular ion and subsequent fragment ions of TOFMS, as well as matching of empirical molecular formulae with those of published components in the in-house chemical library, a total of 44 major components including 21 diterpenoid alkaloids, 12 flavonoids and 11 saponins were identified in QFD. After oral administration of QFD, 22 components in rat plasma were detected and identified by comparing and contrasting the constituents measured in QFD with those in the plasma samples. The results provided valuable chemical information for further pharmacology and active mechanism research on QFD. LC-TOFMS was also applied for the comparison of relative peak area of major active components between QFD and the single herb extracts. The concentration ratios of major saponins detected in the crude herb Radix Astragali were found to be different from those in QFD. The experimental data indicated that the decocting process could result in differences in the amounts of active components. PMID:21594877

  14. Gastroprotective effects of new diterpenoid derivatives from Azorella cuatrecasasii Mathias & Constance obtained using a β-cyclodextrin complex with microbial and chemical transformations.

    PubMed

    Sepúlveda, Beatriz; Quispe, Cristina; Simirgiotis, Mario; García-Beltrán, Olimpo; Areche, Carlos

    2016-07-15

    Mulinane diterpenoids isolated from Azorella species have displayed gastroprotective effects in animal models. In this study we have transformed the main constituent, mulin-11,13-dien-20 oic acid from this plant using the filamentous fungus Mucor plumbeus and a β-cyclodextrin inclusion complex and we have obtained two main products with good yields (33% and 15% for compound 4 and 5, respectively) for further preparation of semisynthetic derivatives to evaluate their gastroprotective effects. In addition, one of the compounds isolated from Azorella cuatrecasasii was new (9-epi-13α-hydroxymulinene 1). Six new derivatives 4a-4c and 5a-5c were then prepared by simple chemical transformations. The structures of all compounds were elucidated by spectroscopic means based on 1D and 2D-NMR techniques. Some 8 diterpenes were evaluated for their gastroprotective effects in the ethanol/HCl-induced ulcer model in mice at 20mg/kg. The highest gastroprotective activity was shown by 7α,16-dihydroxymulin-11,13-dien-20-oic acid 5, which was higher than the reference drug lansoprazole, while 16-hydroxymulin-11,13-dien-20-oic acid 4 was as active as lansoprazole. PMID:27262597

  15. Jatrophane Diterpenoids as Modulators of P-Glycoprotein-Dependent Multidrug Resistance (MDR): Advances of Structure-Activity Relationships and Discovery of Promising MDR Reversal Agents.

    PubMed

    Zhu, Jianyong; Wang, Ruimin; Lou, Lanlan; Li, Wei; Tang, Guihua; Bu, Xianzhang; Yin, Sheng

    2016-07-14

    The phytochemical study of Pedilanthus tithymaloides led to the isolation of 13 jatrophane diterpenoids (1-13), of which eight (1-8) are new. Subsequent structural modification of the major components by esterification, hydrolysis, hydrogenation, or epoxidation yielded 22 new derivatives (14-35). Thus, a jatrophane library containing two series of compounds was established to screen for P-glycoprotein (Pgp)-dependent MDR modulators. The activity was evaluated through a combination of Rho123 efflux and chemoreversal assays on adriamycin resistant human hepatocellular carcinoma cell line HepG2 (HepG2/ADR) and adriamycin resistant human breast adenocarcinoma cell line MCF-7 (MCF-7/ADR). Compounds 19, 25, and 26 were identified as potent MDR modulators with greater chemoreversal ability and less cytotoxicity than the third-generation drug tariquidar. The structure-activity relationship (SAR) was discussed, which showed that modifications beyond just increasing the lipophilicity of this class of Pgp inhibitors are beneficial to the activity. Compound 26, which exhibited a remarkable metabolic stability in vitro and a favorable antitumor effect in vivo, would serve as a promising lead for the development of new MDR reversal agents. PMID:27328029

  16. [Synthesis and antituberculosis activity of the derivatives of glycoside steviolbioside from the plant Stevia rebaudiana and diterpenoid isosteviol containing hydrazone, hydrazide and pyridinoyl moieties].

    PubMed

    Kataev, V E; Strobykina, I Iu; Andreeva, O V; Garifullin, B F; Sharipova, R R; Mironov, V F; Chestnova, R V

    2011-01-01

    Conjugates of antitubercular drug Isoniazid (hydrazide of isonicotinic acid), nicotinic and alpha-picolinic acid hydrazides and glycoside steviolbioside from the plant Stevia rebaudiana as well as the product of its acid hydrolysis, diterpenoid isosteviol, were synthesized. Besides, isosteviol hydrazide and hydrazone derivatives as well as conjugates containing two isosteviol moieties connected by dihydrazide linker were also obtained. Both initial compounds and their synthetic derivatives inhibit the growth of Mycobacterium tuberculosis (H37Rv in vitro). The minimum concentration at which the growth of M. tuberculosis was inhibited by 100% (MIC) for stevioside and steviolbioside equals 7.5 and 3.8 microg/mL, respectively. MIC values for conjugates of the hydrazides of pyridine carbonic acids and steviolbioside as well as isosteviol are in the ranges 5-10 and 10-20 microg/mL, respectively. Maximum inhibitory effect against M. tuberculosis showed the conjugates of isosteviol and adipic acid dihydrazide (MIC values ranged from 1.7 to 3.1 microg/mL). Antitubercular activity of the compounds studied is higher than the activity of antitubercular drug Pyrizanamide (MIC = 12.5-20 microg/mL) but lower than the activity of antitubercular drug Isoniazid (MIC = 0.02-0.04 microg/mL). PMID:22096997

  17. Seed dormancy breaking diterpenoids, including novel brassicicenes J and K, from fungus Alternaria brassicicola, and their necrotic/apoptotic activities in HL-60 cells.

    PubMed

    Kenmoku, Hiromichi; Takeue, Sayaka; Oogushi, Megumi; Yagi, Yasuyuki; Sassa, Takeshi; Toyota, Masao; Asakawa, Yoshinori

    2014-03-01

    To find new metabolites similar to cotylenins and fusicoccins from the fungus Alternaria brassicicola, screening tests were carried out using the lettuce seed dormancy breaking assay. Activity-guided fractionation of the EtOAc extract from the culture using the assay afforded the isolation of two novel fusicoccane diterpenoids named brassicicenes J (1) and K (2), along with three known brassicicenes A (3), B (4), and F (5). Their structures were elucidated from extensive NMR spectral data and by comparison of these with those reported in the literature. Brassicicenes (1-5) exhibited weak to moderate seed dormancy breaking activities against lettuce seeds in the presence of abscisic acid. In addition, the necrotic/apoptotic activities of the brassicicenes (1-5), fusicoccin A (6) and cotylenin A (7) were evaluated by determining their cytotoxicity, cell viability and caspase-3/7 activation on the HL-60 cell line. Brassicicene K (2) exhibited similar cytostatic profiles to that of cotylenin A (7), and brassicicenes J (1), A (3), B (4), and F (5) exhibited necrotic activity. This is the first report of the seed dormancy breaking activity of brassicicenes in plants, and of necrotic/apoptotic activity in mammalian cells. PMID:24689212

  18. Differential control of growth, cell cycle progression, and expression of NF-{kappa}B in human breast cancer cells MCF-7, MCF-10A, and MDA-MB-231 by ponicidin and oridonin, diterpenoids from the chinese herb Rabdosia rubescens

    SciTech Connect

    Hsieh Tzechen; Wijeratne, E. Kithsiri; Liang Jingyu; Gunatilaka, A. Leslie; Wu, Joseph M. . E-mail: Joseph_Wu@nymc.edu

    2005-11-11

    Ponicidin and oridonin are novel diterpenoids isolated from Rabdosia rubescens. We tested their effects in MCF-7 and MDA-MB-231 cells, as representing low and high invasive breast carcinoma, with normal MCF-10A cells. Clonogenicity and proliferation in MCF-7 cells were inhibited more significantly by ponicidin than oridonin, while the reverse was observed in MCF-10A cells. Ponicidin and oridonin induced S/G{sub 2}M arrest and G{sub 1}/S block in MCF-7 cells. In MCF-10A cells treated with either diterpenoid, induction of apoptosis was observed. Moreover, oridonin almost completely blocked MCF-10A progression from S to G{sub 2}/M phase; in contrast, ponicidin-treated MCF-10A cells showed no discernable changes in cell cycle phase distribution. Neither diterpenoid affected growth of MDA-MB-231 cells, at the dose range effective for MCF-7 or MCF-10A cells. Ponicidin-treated MCF-7 cells expressed reduced levels of cyclin B1, cdc2, transcription factor E2F, and Rb including phosphorylation at S780. Less pronounced effects were found in cells treated with oridonin. Neither compound altered cyclin D1 and cdk4 in MCF-7 cells. In MCF-10A cells, oridonin was more active than ponicidin in inhibiting the expression of cyclin B1, cdc2, S780-phosphorylated Rb, and E2F. To further investigate induction of apoptosis in MCF-10A cells, we measured changes in NF-{kappa}B. Decreases in p65 or p50 forms of NF-{kappa}B and its upstream regulator I-{kappa}B were found in oridonin-treated MCF-10A and not MCF-7 cells. Taken together, these results provide a mechanistic framework for the cellular effects of ponicidin and oridonin in different stage breast cancer cells.

  19. Collective Total Syntheses of Atisane-Type Diterpenes and Atisine-Type Diterpenoid Alkaloids: (±)-Spiramilactone B, (±)-Spiraminol, (±)-Dihydroajaconine, and (±)-Spiramines C and D.

    PubMed

    Cheng, Hang; Zeng, Fan-Hao; Yang, Xue; Meng, Yin-Juan; Xu, Liang; Wang, Feng-Peng

    2016-01-01

    The first total syntheses of the architecturally complex atisane-type diterpenes and biogenetically related atisine-type diterpenoid alkaloids (±)-spiramilactone B, (±)-spiraminol, (±)-dihydroajaconine, and (±)-spiramines C and D are reported. Highlights of the synthesis include a late-stage biomimetic transformation of spiramilactone B, a facile formal lactone migration from the pentacyclic skeleton of spiramilactone E, a highly efficient and diastereoselective 1,7-enyne cycloisomerization to construct the functionalized tetracyclic atisane skeleton, and a tandem retro-Diels-Alder/intramolecular Diels-Alder sequence to achieve the tricyclo[6.2.2.0] ring system.

  20. LC-MS and 1H NMR as an improved dereplication tool to identify antifungal diterpenoids from Sagittaria latifolia

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A dereplication strategy using a combination of liquid chromatography-mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (1H NMR) to facilitate compound identification towards antifungal natural product discovery is presented. This analytical approach takes advantage of th...

  1. Diterpanes, triterpanes, steranes, and aromatic hydrocarbons in natural bitumens and pyrolysates from different humic coals

    NASA Astrophysics Data System (ADS)

    Lu, Shan-Tan; Kaplan, Isaac R.

    1992-07-01

    Data are presented on the distribution of diterpanes, triterpanes, steranes, and aromatic hydrocarbons in the natural bitumens extracted from unheated coals identified as Rocky Mountain coal (RMC), Australian Gippsland Latrobe Eocene coal (GEC), Australian Gippsland Latrobe Cretaceous coal (GCC), and Texas Wilcox lignite (WL), as well as from pyrolysates obtained from heating of these coals. It was found that pentacyclic triterpanes are dominant in GEC, GCC, and WL, whereas diterpanes strongly predominate in the bitumen of RMC, indicating that resin is a more important constituent of RMC than of the other coals and that it releases the diterpenoids at an early stage of diagenesis. It was also found that the composition of diterpanes is different among these coals and that the distributions of sterane and triterpane in the natural bitumen of coals are very different from those of pyrolysates.

  2. Discovery and development of natural product oridonin-inspired anticancer agents.

    PubMed

    Ding, Ye; Ding, Chunyong; Ye, Na; Liu, Zhiqing; Wold, Eric A; Chen, Haiying; Wild, Christopher; Shen, Qiang; Zhou, Jia

    2016-10-21

    Natural products have historically been, and continue to be, an invaluable source for the discovery of various therapeutic agents. Oridonin, a natural diterpenoid widely applied in traditional Chinese medicines, exhibits a broad range of biological effects including anticancer and anti-inflammatory activities. To further improve its potency, aqueous solubility and bioavailability, the oridonin template serves as an exciting platform for drug discovery to yield better candidates with unique targets and enhanced drug properties. A number of oridonin derivatives (e.g. HAO472) have been designed and synthesized, and have contributed to substantial progress in the identification of new agents and relevant molecular mechanistic studies toward the treatment of human cancers and other diseases. This review summarizes the recent advances in medicinal chemistry on the explorations of novel oridonin analogues as potential anticancer therapeutics, and provides a detailed discussion of future directions for the development and progression of this class of molecules into the clinic. PMID:27344488

  3. Diterpanes, triterpanes, steranes, and aromatic hydrocarbons in natural bitumens and pyrolysates from different humic coals

    NASA Technical Reports Server (NTRS)

    Lu, Shan-Tan; Kaplan, Isaac R.

    1992-01-01

    Data are presented on the distribution of diterpanes, triterpanes, steranes, and aromatic hydrocarbons in the natural bitumens extracted from unheated coals identified as Rocky Mountain coal (RMC), Australian Gippsland Latrobe Eocene coal (GEC), Australian Gippsland Latrobe Cretaceous coal (GCC), and Texas Wilcox lignite (WL), as well as from pyrolysates obtained from heating of these coals. It was found that pentacyclic triterpanes are dominant in GEC, GCC, and WL, whereas diterpanes strongly predominate in the bitumen of RMC, indicating that resin is a more important constituent of RMC than of the other coals and that it releases the diterpenoids at an early stage of diagenesis. It was also found that the composition of diterpanes is different among these coals and that the distributions of sterane and triterpane in the natural bitumen of coals are very different from those of pyrolysates.

  4. A strategy for the separation of diterpenoid isomers from the root of Aralia continentalis by countercurrent chromatography: The distribution ratio as a substitute for the partition coefficient and a three-phase solvent system.

    PubMed

    Lee, Kyoung Jin; Song, Kwang Ho; Choi, Wonmin; Kim, Yeong Shik

    2015-08-01

    Aralia continentalis (Araliaceae) is widely used as a medicinal plant in East Asia. Previous studies have indicated that diterpenoid isomers (kaurenoic acid, continentalic acid, and ent-continentalic acid) are the major bioactive compounds of this plant. A new strategy was developed to alleviate difficulties in the separation of these isomers from this plant. A three-phase solvent system was applied to separate the isomers, and furthermore, the distribution ratio (Kc) was introduced as a substitute for the partition coefficient (KD). For compounds exhibiting a single equilibrium, their distributions in two immiscible phases were only affected by the partition coefficient of each solute. However, compounds that have a dissociating functional group (e.g., -COOH) are involved in two types of equilibrium in the two-phase system. In this case, the partitioning behaviors of the solutes are greatly affected by the pH of the solution. A mathematical prediction was applied for adjusting the solutions to the proper pH values. To prevent non-used phase (medium phase) waste, both the stationary phase (upper phase) and mobile phase (lower phase) were prepared on-demand without pre-saturation with the application of (1)H NMR. Each fraction obtained was collected and dried, yielding the following diterpenoid isomers from the 50mg injected sample: kaurenoic acid (19.7mg, yield: 39%) and ent-continentalic acid (21.3mg, yield: 42%).

  5. Apparent contradiction: psychrotolerant bacteria from hydrocarbon-contaminated arctic tundra soils that degrade diterpenoids synthesized by trees.

    PubMed

    Yu, Z; Stewart, G R; Mohn, W W

    2000-12-01

    Resin acids are tricyclic terpenoids occurring naturally in trees. We investigated the occurrence of resin acid-degrading bacteria on the Arctic tundra near the northern coast of Ellesmere Island (82 degrees N, 62 degrees W). According to most-probable-number assays, resin acid degraders were abundant (10(3) to 10(4) propagules/g of soil) in hydrocarbon-contaminated soils, but they were undetectable (<3 propagules/g of soil) in pristine soils from the nearby tundra. Plate counts indicated that the contaminated and the pristine soils had similar populations of heterotrophs (10(6) to 10(7) propagules/g of soil). Eleven resin acid-degrading bacteria belonging to four phylogenetically distinct groups were enriched and isolated from the contaminated soils, and representative isolates of each group were further characterized. Strains DhA-91, IpA-92, and IpA-93 are members of the genus Pseudomonas. Strain DhA-95 is a member of the genus Sphingomonas. All four strains are psychrotolerant, with growth temperature ranges of 4 degrees C to 30 degrees C (DhA-91 and DhA-95) or 4 degrees C to 22 degrees C (IpA-92 and IpA-93) and with optimum temperatures of 15 to 22 degrees C. Strains DhA-91 and DhA-95 grew on the abietanes, dehydroabietic and abietic acids, but not on the pimaranes, isopimaric and pimaric acids. Strains IpA-92 and IpA-93 grew on the pimaranes but not the abietanes. All four strains grew on either aliphatic or aromatic hydrocarbons, which is unusual for described resin acid degraders. Eleven mesophilic resin acid degraders did not use hydrocarbons, with the exception of two Mycobacterium sp. strains that used aliphatic hydrocarbons. We conclude that hydrocarbon contamination in Arctic tundra soil indirectly selected for resin acid degraders, selecting for hydrocarbon degraders that coincidentally use resin acids. Psychrotolerant resin acid degraders are likely important in the global carbon cycle and may have applications in biotreatment of pulp and paper mill

  6. Apparent Contradiction: Psychrotolerant Bacteria from Hydrocarbon-Contaminated Arctic Tundra Soils That Degrade Diterpenoids Synthesized by Trees

    PubMed Central

    Yu, Zhongtang; Stewart, Gordon R.; Mohn, William W.

    2000-01-01

    Resin acids are tricyclic terpenoids occurring naturally in trees. We investigated the occurrence of resin acid-degrading bacteria on the Arctic tundra near the northern coast of Ellesmere Island (82°N, 62°W). According to most-probable-number assays, resin acid degraders were abundant (103 to 104 propagules/g of soil) in hydrocarbon-contaminated soils, but they were undetectable (<3 propagules/g of soil) in pristine soils from the nearby tundra. Plate counts indicated that the contaminated and the pristine soils had similar populations of heterotrophs (106 to 107 propagules/g of soil). Eleven resin acid-degrading bacteria belonging to four phylogenetically distinct groups were enriched and isolated from the contaminated soils, and representative isolates of each group were further characterized. Strains DhA-91, IpA-92, and IpA-93 are members of the genus Pseudomonas. Strain DhA-95 is a member of the genus Sphingomonas. All four strains are psychrotolerant, with growth temperature ranges of 4°C to 30°C (DhA-91 and DhA-95) or 4°C to 22°C (IpA-92 and IpA-93) and with optimum temperatures of 15 to 22°C. Strains DhA-91 and DhA-95 grew on the abietanes, dehydroabietic and abietic acids, but not on the pimaranes, isopimaric and pimaric acids. Strains IpA-92 and IpA-93 grew on the pimaranes but not the abietanes. All four strains grew on either aliphatic or aromatic hydrocarbons, which is unusual for described resin acid degraders. Eleven mesophilic resin acid degraders did not use hydrocarbons, with the exception of two Mycobacterium sp. strains that used aliphatic hydrocarbons. We conclude that hydrocarbon contamination in Arctic tundra soil indirectly selected for resin acid degraders, selecting for hydrocarbon degraders that coincidentally use resin acids. Psychrotolerant resin acid degraders are likely important in the global carbon cycle and may have applications in biotreatment of pulp and paper mill effluents. PMID:11097882

  7. Discovery of Highly Sweet Compounds from Natural Sources

    NASA Astrophysics Data System (ADS)

    Kinghorn, A. Douglas; Kennelly, Edward J.

    1995-08-01

    Sucrose, the most widely used sweetener globally, is of plant origin. In addition, a number of other plant constituents are employed as dietary sucrose substitutes in one or more countries, including the diterpenoid, stevioside, the triterpenoid, glycyrrhizin, and the protein, thaumatin. Accordingly, there has been much interest in discovering further examples of potently sweet compounds of natural origin, for potential use in foods, beverages, and medicines. Approximately 75 plant-derived compounds are presently known, mainly representative of the flavonoid, proanthocyandin, protein, steroidal saponin, and terpenoid chemotypes. In our program directed towards the elucidation of further highly sweet molecules from plants, candidate sweet-tasting plants for laboratory investigation are obtained from ethnobotanical observations in the field or in the existing literature. Examples of novel sweet-tasting compounds obtained so far are the sesquiterpenoids, hernandulcin and 4beta-hydroxyhemandulcin; the triterpenoids, abrusosides A-D; a semi-synthetic dihydroflavonol based on the naturally occurring substance, dihydroquercetin 3-acetate; and the proanthocyanidin, selligueain A. Natural product sweeteners may be of potential commercial use per se, and can be used for synthetic modification to produce improved sweeteners, and can also be of value scientifically to aid in the better understanding of structure-sweetness relationships.

  8. Immunofluorescence localization of levopimaradiene/abietadiene synthase in methyl jasmonate treated stems of Sitka spruce (Picea sitchensis) shows activation of diterpenoid biosynthesis in cortical and developing traumatic resin ducts.

    PubMed

    Zulak, Katherine G; Dullat, Harpreet K; Keeling, Christopher I; Lippert, Dustin; Bohlmann, Jörg

    2010-10-01

    Conifers produce terpenoid-rich oleoresin in specialized resin ducts as a main line of defence against pests and pathogens. In spruce species (Picea spp.), axial resin ducts are either present constitutively in the cortex tissue (cortical resin ducts, CRDs) or are formed de novo as traumatic resin ducts (TRDs) in the cambial zone upon attack by insects, fungi or treatment with methyl jasmonate (MeJA). Using immunofluorescence localization we tested if previously formed CRDs respond to MeJA treatment with increased capacity for diterpenoid biosynthesis. We also tested the dynamics of diterpene synthase localization in the cambial zone. Immunofluorescence localization was performed using an antibody against a diterpene synthase, levopimaradiene/abietadiene synthase (LAS), in stem cross-sections of untreated and 0.1% MeJA-treated 4-year old Sitka spruce (P. sitchensis) trees. No fluorescence signal was observed in untreated stem cross-sections; however, signal was present 2 days after treatment with MeJA exclusively in the epithelial cells of CRDs. Fluorescence steadily increased in the CRD epithelial cells 4 and 8 days after treatment. At 8days, additional fluorescence was observed in developing epithelial cells of traumatic resin ducts TRDs in the cambial zone. These results confirm that resin duct epithelial cells are the main site of diterpene biosynthesis in Sitka spruce, diterpenoid biosynthesis is induced in CRD epithelial cells early upon treatment with MeJA, and immature developing TRD epithelial cells produce diterpene synthase enzyme. Overall, the results of this work improve our understanding of spatial and temporal patterns of induced diterpene resin acid biosynthesis in conifers.

  9. Natural organic compounds as tracers for biomass combustion in aerosols

    SciTech Connect

    Simoneit, B.R.T. |; Abas, M.R. bin |; Cass, G.R. |; Rogge, W.F. |; Mazurek, M.A.; Standley, L.J.; Hildemann, L.M.

    1995-08-01

    Biomass combustion is an important primary source of carbonaceous particles in the global atmosphere. Although various molecular markers have already been proposed for this process, additional specific organic tracers need to be characterized. The injection of natural product organic tracers to smoke occurs primarily by direct volatilization/steam stripping and by thermal alteration based on combustion temperature. The degree of alteration increases as the burn temperature rises and the moisture content of the fuel decreases. Although the molecular composition of organic matter in smoke particles is highly variable, the molecular structures of the tracers are generally source specific. The homologous compound series and biomarkers present in smoke particles are derived directly from plant wax, gum and resin by volatilization and secondarily from pyrolysis of biopolymers, wax, gum and resin. The complexity of the organic components of smoke aerosol is illustrated with examples from controlled burns of temperate and tropical biomass fuels. Burning of biomass from temperate regions (i.e., conifers) yields characteristic tracers from diterpenoids as well as phenolics and other oxygenated species, which are recognizable in urban airsheds. The major organic components of smoke particles from tropical biomass are straight-chain, aliphatic and oxygenated compounds and triterpenoids. The precursor-to-product approach of organic geochemistry can be applied successfully to provide tracers for studying smoke plume chemistry and dispersion.

  10. Temporal naturalism

    NASA Astrophysics Data System (ADS)

    Smolin, Lee

    2015-11-01

    Two people may claim both to be naturalists, but have divergent conceptions of basic elements of the natural world which lead them to mean different things when they talk about laws of nature, or states, or the role of mathematics in physics. These disagreements do not much affect the ordinary practice of science which is about small subsystems of the universe, described or explained against a background, idealized to be fixed. But these issues become crucial when we consider including the whole universe within our system, for then there is no fixed background to reference observables to. I argue here that the key issue responsible for divergent versions of naturalism and divergent approaches to cosmology is the conception of time. One version, which I call temporal naturalism, holds that time, in the sense of the succession of present moments, is real, and that laws of nature evolve in that time. This is contrasted with timeless naturalism, which holds that laws are immutable and the present moment and its passage are illusions. I argue that temporal naturalism is empirically more adequate than the alternatives, because it offers testable explanations for puzzles its rivals cannot address, and is likely a better basis for solving major puzzles that presently face cosmology and physics. This essay also addresses the problem of qualia and experience within naturalism and argues that only temporal naturalism can make a place for qualia as intrinsic qualities of matter.

  11. Cloning, molecular characterization and functional analysis of 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (HDR) gene for diterpenoid tanshinone biosynthesis in Salvia miltiorrhiza Bge. f. alba.

    PubMed

    Hao, Gangping; Shi, Renjiu; Tao, Ru; Fang, Qian; Jiang, Xingyu; Ji, Haiwei; Feng, Lei; Huang, Luqi

    2013-09-01

    The enzyme 1-hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (HDR) is a terminal-acting enzyme in the plastid MEP pathway, which produce isoprenoid precursors. The full-length cDNA of HDR, designated SmHDR1 (Genbank Accession No. JX516088), was isolated for the first time from Salvia miltiorrhiza Bge. f. alba. SmHDR1 contains a 1389-bp open reading frame encoding 463 amino acids. The deduced SmHDR1 protein, which shows high identity to HDRs of other plant species, is predicted to possess a chloroplast transit peptide at the N-terminus and four conserved cysteine residues. Transcription pattern analysis revealed that SmHDR1 has high levels of transcription in leaves and low levels of transcription in roots and stems. The expression of SmHDR1 was induced by 0.1 mM methyl-jasmonate (MeJA) and salicylic acid (SA), but not by 0.1 mM abscisic acid (ABA), in the hairy roots of S. miltiorrhiza Bge. f. alba. Complementation of SmHDR1 in the Escherichia coli HDR mutant MG1655 ara < > ispH demonstrated the function of this enzyme. A functional color assay in E. coli showed that SmHDR1 accelerates the biosynthesis of β-carotene, indicating that SmHDR1 encodes a functional protein. Overexpression of SmHDR1 enhanced the production of tanshinones in cultured hairy roots of S. miltiorrhiza Bge. f. alba. These results indicate that SmHDR1 is a novel and important enzyme involved in the biosynthesis of diterpenoid tanshinones in S. miltiorrhiza Bge. f. alba.

  12. Triptolide, a diterpenoid triepoxide, induces antitumor proliferation via activation of c-Jun NH{sub 2}-terminal kinase 1 by decreasing phosphatidylinositol 3-kinase activity in human tumor cells

    SciTech Connect

    Miyata, Yoshiki; Sato, Takashi . E-mail: satotak@ps.toyaku.ac.jp; Ito, Akira

    2005-11-04

    Triptolide, a diterpenoid triepoxide extracted from the Chinese herb Tripterygium wilfordii Hook f., exerts antitumorigenic actions against several tumor cells, but the intracellular target signal molecule(s) for this antitumorigenesis activity of triptolide remains to be identified. In the present study, we demonstrated that triptolide, in a dose-dependent manner, inhibited the proliferation of human fibrosarcoma HT-1080, human squamous carcinoma SAS, and human uterine cervical carcinoma SKG-II cells. In addition, triptolide was found to decrease phosphatidylinositol 3-kinase (PI3K) activity. A PI3K inhibitor, LY-294002, mimicked the triptolide-induced antiproliferative activity in HT-1080, SAS, and SKG-II cells. There was no change in the activity of Akt or protein kinase C (PKC), both of which are downstream effectors in the PI3K pathway. Furthermore, the phosphorylation of Ras, Raf, and mitogen-activated protein/extracellular signal-regulated kinase 1/2 was not modified in HT-1080 cells treated with triptolide. However, the phosphorylation of c-Jun NH{sub 2}-terminal kinase 1 (JNK1) was found to increase in both triptolide- and LY-294002-treated cells. Furthermore, the triptolide-induced inhibition of HT-1080 cell proliferation was not observed by JNK1 siRNA-treatment. These results provide novel evidence that PI3K is a crucial target molecule in the antitumorigenic action of triptolide. They further suggest a possible triptolide-induced inhibitory signal for tumor cell proliferation that is initiated by the decrease in PI3K activity, which in turn leads to the augmentation of JNK1 phosphorylation via the Akt and/or PKC-independent pathway(s). Moreover, it is likely that the activation of JNK1 is required for the triptolide-induced inhibition of tumor proliferation.

  13. Nature Detectives

    ERIC Educational Resources Information Center

    Harr, Natalie; Lee, Richard E.; Jr.

    2010-01-01

    Richard Louv's "Last Child in the Woods" (2008) added to a growing consensus to get children outside and experiencing nature. Using ideas from place-based education, the authors present a simple year-long project that brings science, nature, and other curriculum standards to life right in your school yard. With a focus on journaling, this project…

  14. Nature plants.

    PubMed

    2014-06-01

    We welcome our new sister journal Nature Plants and the increased commitment to the plant science community that it represents. This is an opportunity for Nature Genetics to emphasize the use of genetic and genomic tools and resources in discovering new plant biology and solving major agricultural challenges.

  15. Matematica Natural.

    ERIC Educational Resources Information Center

    Lozano, Patricia; Medearis, Linda

    Matematica Natural (Natural Mathematics) is a mathematics curriculum for young children based on the assumption that they learn mathematics through concrete, real life, relevant experiences and that educational differences rather than cultural differences influence math achievement. The curriculum uses hands-on materials and activities to teach…

  16. Natural Beauty

    ERIC Educational Resources Information Center

    Coy, Mary

    2006-01-01

    In this article, the author describes how her art class students were able to create, in just four class periods, clay relief plaques depicting nature. A lesson on texture speeds up the completion of such a project. Seeing that clay is a natural material with its own unique texture, it seemed fitting that the final product should depict a variety…

  17. Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals

    PubMed Central

    Morrone, Dana; Hillwig, Matthew L.; Mead, Matthew E.; Lowry, Luke; Fulton, D. Bruce; Peters, Reuben J.

    2013-01-01

    SYNOPSIS The evolution of natural products biosynthetic pathways can be envisioned to occur via a number of mechanisms. Here we provide evidence that latent plasticity plays a role in such metabolic evolution. In particular, rice (Oryza sativa) produces both ent- and syn-copalyl diphosphate (CPP), which are substrates for downstream diterpene synthases. Here we report that several members of this enzymatic family exhibit dual reactivity with some pairing of ent-, syn-, or normal CPP stereochemistry. Evident plasticity was observed, as a previously reported ent-sandaracopimaradiene synthase also converts syn-CPP to syn-labda-8(17),12E,14-triene, which can be found in planta. Notably, normal CPP is not naturally found in rice. Thus, the presence of diterpene synthases that react with this non-native metabolite reveals latent enzymatic/metabolic plasticity, providing biochemical capacity for utilization of such a novel substrate (i.e., normal CPP) that may arise during evolution, the implications of which are discussed. PMID:21323642

  18. Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals.

    PubMed

    Morrone, Dana; Hillwig, Matthew L; Mead, Matthew E; Lowry, Luke; Fulton, D Bruce; Peters, Reuben J

    2011-05-01

    The evolution of natural product biosynthetic pathways can be envisioned to occur via a number of mechanisms. In the present study we provide evidence that latent plasticity plays a role in such metabolic evolution. In particular, rice (Oryza sativa) produces both ent- and syn-CPP (copalyl diphosphate), which are substrates for downstream diterpene synthases. In the present paper we report that several members of this enzymatic family exhibit dual reactivity with some pairing of ent-, syn- or normal CPP stereochemistry. Evident plasticity was observed, as a previously reported ent-sandaracopimaradiene synthase also converts syn-CPP into syn-labda-8(17),12E,14-triene, which can be found in planta. Notably, normal CPP is not naturally found in rice. Thus the presence of diterpene synthases that react with this non-native metabolite reveals latent enzymatic/metabolic plasticity, providing biochemical capacity for utilization of such a novel substrate (i.e. normal CPP) which may arise during evolution, the implications of which are discussed.

  19. [Natural selection].

    PubMed

    Mayr, E

    1985-05-01

    Much of the resistance against Darwin's theory of natural selection has been due to misunderstandings. It is shown that natural selection is not a tautology and that it is a two-step process. The first step, the production of variation, is under the control of chance; the second step, selection proper, is an anti-chance process, but subject to many constraints. The target of selection is the individual as a whole, and many neutral mutations can be retained as hitchhikers of successful genotypes. Sexual selection results from selection for pure reproductive success.

  20. Uranium, natural

    Integrated Risk Information System (IRIS)

    Uranium , natural ; CASRN 7440 - 61 - 1 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogeni

  1. Nature Watch

    ERIC Educational Resources Information Center

    Sterling, Donna R.

    2010-01-01

    Children are naturally curious about the world in which they live. To focus this sense of wonder, have your students investigate their local habitat as it changes over the year. This multiseason study will build connections and add relevance to the habitats that children learn about. This series of activities for grades 4-6 explores the changing…

  2. Nature's Palette

    ERIC Educational Resources Information Center

    McBride, Brooke B.; Brewer, Carol A.

    2010-01-01

    Flower petals, acorn hats, exoskeletons of beetles, and lichens are just a few of the objects students may find in a surprising array of vivid colors. These tiny examples from nature's palette can be discovered in a school yard, a park, or even along the edges of a paved sidewalk...it simply takes careful observation! This article describes a…

  3. Natural restoration

    SciTech Connect

    Kamlet, K.S.

    1993-02-01

    After a company pays millions of dollars to clean up contaminated site, its liability may not be over. It may have to spend tens of millions more to restore damaged natural resources under an oft-overlooked Superfund program. Examples of liability are cited in this report from the Exxon Valdez oil spill and a pcb leak which contaminated a harbor.

  4. Natural ecosystems

    USGS Publications Warehouse

    Fleishman, Erica; Belnap, Jayne; Cobb, Neil; Enquist, Carolyn A.F.; Ford, Karl; MacDonald, Glen; Pellant, Mike; Schoennagel, Tania; Schmit, Lara M.; Schwartz, Mark; van Drunick, Suzanne; Westerling, Anthony LeRoy; Keyser, Alisa; Lucas, Ryan

    2013-01-01

    Natural Ecosystems analyzes the association of observed changes in climate with changes in the geographic distributions and phenology (the timing of blossoms or migrations of birds) for Southwestern ecosystems and their species, portraying ecosystem disturbances—such as wildfires and outbreaks of forest pathogens—and carbon storage and release, in relation to climate change.

  5. Natural thermodynamics

    NASA Astrophysics Data System (ADS)

    Annila, Arto

    2016-02-01

    The principle of increasing entropy is derived from statistical physics of open systems assuming that quanta of actions, as undividable basic build blocks, embody everything. According to this tenet, all systems evolve from one state to another either by acquiring quanta from their surroundings or by discarding quanta to the surroundings in order to attain energetic balance in least time. These natural processes result in ubiquitous scale-free patterns: skewed distributions that accumulate in a sigmoid manner and hence span log-log scales mostly as straight lines. Moreover, the equation for least-time motions reveals that evolution is by nature a non-deterministic process. Although the obtained insight in thermodynamics from the notion of quanta in motion yields nothing new, it accentuates that contemporary comprehension is impaired when modeling evolution as a computable process by imposing conservation of energy and thereby ignoring that quantum of actions are the carriers of energy from the system to its surroundings.

  6. Natural Product Vibsanin A Induces Differentiation of Myeloid Leukemia Cells through PKC Activation.

    PubMed

    Yu, Zu-Yin; Xiao, He; Wang, Li-Mei; Shen, Xing; Jing, Yu; Wang, Lin; Sun, Wen-Feng; Zhang, Yan-Feng; Cui, Yu; Shan, Ya-Jun; Zhou, Wen-Bing; Xing, Shuang; Xiong, Guo-Lin; Liu, Xiao-Lan; Dong, Bo; Feng, Jian-Nan; Wang, Li-Sheng; Luo, Qing-Liang; Zhao, Qin-Shi; Cong, Yu-Wen

    2016-05-01

    All-trans retinoic acid (ATRA)-based cell differentiation therapy has been successful in treating acute promyelocytic leukemia, a unique subtype of acute myeloid leukemia (AML). However, other subtypes of AML display resistance to ATRA-based treatment. In this study, we screened natural, plant-derived vibsane-type diterpenoids for their ability to induce differentiation of myeloid leukemia cells, discovering that vibsanin A potently induced differentiation of AML cell lines and primary blasts. The differentiation-inducing activity of vibsanin A was mediated through direct interaction with and activation of protein kinase C (PKC). Consistent with these findings, pharmacological blockade of PKC activity suppressed vibsanin A-induced differentiation. Mechanistically, vibsanin A-mediated activation of PKC led to induction of the ERK pathway and decreased c-Myc expression. In mouse xenograft models of AML, vibsanin A administration prolonged host survival and inhibited PKC-mediated inflammatory responses correlated with promotion of skin tumors in mice. Collectively, our results offer a preclinical proof of concept for vibsanin A as a myeloid differentiation-inducing compound, with potential application as an antileukemic agent. Cancer Res; 76(9); 2698-709. ©2016 AACR.

  7. Natural products and altered derivatives as tracers for biomass combustion in aerosols

    SciTech Connect

    Simoneit, B.R.T.; Radzi bin Abas, M.; Cass, G.R.

    1995-12-01

    Biomass combustion is an important primary source of carbonaceous particles in the global atmosphere. Various molecular markers have been proposed for this process but additional specific tracers are needed. The injection of natural product organic compounds into smoke occurs primarily by direct volatilization/steam stripping and by pyrolysis. Although the composition of organic matter in smoke particles is highly variable, the molecular structures of the tracers are generally source specific. Homologous compounds and biomarkers present in smoke are derived directly from plant wax, gum and resin by volatilization and secondarily from pyrolysis of biopolymers (e.g., lignin, cutin, suberin), wax, gum and resin. The component complexity is illustrated with examples from controlled bums of temperate and tropical biomass fuels. Conifer smoke contains characteristic tracers from diterpenoids as well as phenolics and other oxygenated species. These are recognizable in urban airsheds. The major organic components of smoke from tropical biomass are straight-chain, aliphatic and oxygenated compounds and triterpenoids. Several compounds are potential key indicators for combustion of such biomass. The precursor to product approach of organic geochemistry can be applied successfully to provide molecular tracers for studying smoke plume chemistry and dispersion.

  8. Natural products from semi-mangrove flora: source, chemistry and bioactivities.

    PubMed

    Li, Min-Yi; Xiao, Qiang; Pan, Jian-Yu; Wu, Jun

    2009-02-01

    This review covers the source, chemistry and bioactivities of natural products from semi-mangrove species worldwide. The chemotaxonomy of semi-mangrove plants and total synthesis of heritol analogues, which are potential biocompatible pesticides, are discussed.1 Introduction, 2 Acanthaceae, 2.1 Acanthus, 2.1.1 Aliphatic glycosides, 2.1.2 Alkaloids, 2.1.3 Flavonoids, 2.1.4 Lignan glycosides, 2.1.5 Megastigmane and phenolic glycosides, 2.1.6 Phenylethanol glycosides, 2.1.7 Triterpenoids, 2.1.8 Miscellaneous, 2.1.9 Bioactivities, 3 Euphorbiaceae, 3.1 Excoecaria, 3.1.1 Diterpenoids, 3.1.2 Miscellaneous, 3.1.3 Bioactivities, 4 Lythraceae, 4.1 Pemphis acidula, 5 Sterculiaceae, 5.1 Heritiera littoralis, 5.1.1 Flavones, 5.1.2 Triterpenoids, 5.1.3 Benzene derivatives, 5.1.4 Sesquiterpenes, 5.1.5 Steroids, 6 Total syntheses of heritol and its analogues, 7 Chemotaxonomy and concluding remarks, 8 Acknowledgements 9 References.

  9. Natural Strain

    NASA Technical Reports Server (NTRS)

    Freed, Alan D.

    1997-01-01

    Logarithmic strain is the preferred measure of strain used by materials scientists, who typically refer to it as the "true strain." It was Nadai who gave it the name "natural strain," which seems more appropriate. This strain measure was proposed by Ludwik for the one-dimensional extension of a rod with length l. It was defined via the integral of dl/l to which Ludwik gave the name "effective specific strain." Today, it is after Hencky, who extended Ludwik's measure to three-dimensional analysis by defining logarithmic strains for the three principal directions.

  10. Insights into the mechanism of natural terpenoids as NF-κB inhibitors: an overview on their anticancer potential.

    PubMed

    Jain, H; Dhingra, N; Narsinghani, T; Sharma, R

    2016-09-01

    The transcription factor, nuclear factor kappa B (NF-kB) is one of the principal inducible protein in mammals known to control the gene expression in many critical physiological responses such as oxidative stress, inflammation etc. and has been shown to play an important role in the pathogenesis of cancer. Terpenoids are major constituents present in nutritionally used fruits, vegetables and different spices which possess various pharmacological action including anticancer activity. Various terpenoids, viz. monoterpenoids, sesquiterpenoids, diterpenoids, sesterterpenoids, triterpenoids, tetraterpenoids and polyterpenoids inhibit NF-kB signa-ling pathway through IkB phosphorylation, DNA binding, p65 translocation etc. Keeping in mind these facts, the present review revealed the anti-cancer potential of naturally occurring terpenoids highlighting their mechanism of NF-kB inhibition. This review also focuses on some of the naturally occurring terpenoids belonging to various chemical categories with potential inhibitory effects on NF-kB and their role in the treatment of cancer. PMID:27685522

  11. Natural inflation

    SciTech Connect

    Frieman, J.A.

    1991-02-01

    A pseduo-Nambu-Goldstone boson, with a potential of the form V({phi}) = {Lambda}{sup 4}(1 {plus minus} cos({phi}/f)), can naturally give rise to an epoch of inflation in the early universe. Successful inflation can be achieved if f {approximately} m{sub pl} and {Lambda} {approximately} m{sub GUT}. Such mass scales arise in particle physics models with a gauge group that becomes strongly interacting a the GUT scale, e.g., as is expected to happen in the hidden sector of superstring theories. The density fluctuation spectrum is a non-scale-invariant power law, with extra power on large scales. 12 refs., 3 figs.

  12. Natural Strain

    NASA Technical Reports Server (NTRS)

    Freed, Alan D.

    1995-01-01

    The purpose of this paper is to present a consistent and thorough development of the strain and strain-rate measures affiliated with Hencky. Natural measures for strain and strain-rate, as I refer to them, are first expressed in terms of of the fundamental body-metric tensors of Lodge. These strain and strain-rate measures are mixed tensor fields. They are mapped from the body to space in both the Eulerian and Lagrangian configurations, and then transformed from general to Cartesian fields. There they are compared with the various strain and strain-rate measures found in the literature. A simple Cartesian description for Hencky strain-rate in the Lagrangian state is obtained.

  13. [Naturalizing empathy].

    PubMed

    Decety, J

    2002-01-01

    Empathy is the ability to share emotions with others. It is acknowledged to be a powerful means of tacit communication, a key ingredient in any therapeutic relationship as well as in psychotherapy. Empathy is the cornerstone in the humanist perspective (Ego-psychology) in clinical psychology. This approach is often considered as poorly grounded on scientific and objective evidence. It is however acknowledged that empathetic therapists are more effective than less empathetic therapists. I shall argue that this paradox, i.e. it is the least scientific and the less validated psychotherapeutic approach that is the most efficient, can be eliminated if one considers the nature of empathy, its biological foundation, its evolutionary origin and its cognitive architecture. In this paper I will suggest that empathy is based on specific information processing modules which have been designed by natural selection to cope with social regularities in expressing and reading emotional states. This has provided adaptive benefits to individuals living in large groups bestowing them with mechanisms for cooperativity, altruism and more generally various aspects of prosocial behaviour. The capacity to express emotions, and to read and understand emotions of others also ensures implicit communication with others and may be at the root of intersubjectivity. This perspective on empathy is then articulated with two concurrent hypotheses regarding theory of mind (the simulation and the theory-theory) which aim to explain the human capacity to understand that the behaviors of other intelligent agents are caused by intentions, desires and beliefs. In this context, empathy can be considered as a simulation (or analogical) process that is necessary to understand but not sufficient to interpret other people. This last issue is relevant to clinical practice. PMID:11963348

  14. Novel bioactive diterpenoids from Aframomum aulacocarpos.

    PubMed

    Ayafor, J F; Tchuendem, M H; Nyasse, B; Tillequin, F; Anke, H

    1994-07-01

    Three new labdane diterpenes, 12 alpha,17-epoxy-3 beta-hydroxy-8(9),13- labdadien-16,15-olide (aulacocarpinolide) [1], methyl 8 beta,17:14 zeta,15-diepoxy-3 beta-hydroxy- 12E-labden-16-oate (aulacocarpin A) [2], and methyl 8 beta,17:14 zeta,15-diepoxy-3 beta,6 beta- dihydroxy-12E-labden-16-oate (aulacocarpin B) [3] have been isolated from the Cameroonian spice, Aframomum aulacocarpos, and their structures elucidated using spectroscopic techniques. The known bioactive diterpene dialdehyde, 8 beta,17-epoxy-12E-labdene-15,16-dial (aframodial) [4] was also isolated. Compounds 1-3 showed weak antimicrobial and cytotoxic activities.

  15. The social nature of natural childbirth.

    PubMed

    Mansfield, Becky

    2008-03-01

    This paper aims to develop a better understanding of what proponents of natural childbirth mean by "natural." Using a biosocial approach to birth that posits that all birth is both social and natural, the paper investigates how proponents represent the relationship between nature and society. The study asks about what kinds of nature-society relationships are expressed in proponents' representations of natural childbirth. The study examines how natural childbirth is represented by proponents in popular non-fictional English language books written for pregnant women. Claims in these books are not taken as reality, but are analyzed as ideas about nature-society relations. The central finding is that these authors simultaneously emphasize the naturalness of birth and showcase three types of social practices that they describe as being integral to natural childbirth: (1) activity during birth, (2) preparation before birth, and (3) social support, both in an individual and in a broader socio-cultural sense. At least for these authors, it is these social practices that allow natural childbirth to be natural. These findings on the social nature of natural childbirth challenge current social science scholarship, in which natural childbirth is characterized as an essentializing and nostalgic attempt to return to nature.

  16. Supramolecular design of biocompatible nanocontainers based on amphiphilic derivatives of a natural compound isosteviol.

    PubMed

    Gabdrakhmanov, Dinar R; Voronin, Mikhail A; Zakharova, Lucia Ya; Konovalov, Alexander I; Khaybullin, Ravil N; Strobykina, Irina Yu; Kataev, Vladimir E; Faizullin, Dzhigangir A; Gogoleva, Natalia E; Konnova, Tatiana A; Salnikov, Vadim V; Zuev, Yuriy F

    2013-10-21

    Two diterpenoid surfactants with ammonium head groups and bromide (S1) or tosylate (S2) counterions have been synthesized. Exploration of these biomimetic species made it possible to demonstrate that even minor structural changes beyond their chemical nature may dramatically affect their solution behavior. While their aggregation thresholds differ inconsiderably, morphological behavior and affinity to lipid bilayer are strongly dependent on the counterion nature. Compound S2 demonstrates properties of typical surfactants and forms small micelle-like aggregates above critical micelle concentration. For surfactant S1, two critical concentrations and two types of aggregates occur. Structural transitions have been observed between small micelles and aggregates with higher aggregation numbers and hydrodynamic diameter of ca. 150 nm. Unlike S2, surfactant S1 is shown to integrate with liposomes based on dipalmitoylphosphatidylcholine, resulting in a decrease of the temperature of the main phase transition. Both surfactants demonstrate an effective complexation capacity toward oligonucleotide (ONu), which is supported by recharging the surfactant-ONu complexes and the ethidium bromide exclusion at a low N/P ratio. Meanwhile, a very weak complexation of plasmid DNA with the surfactants has been revealed in the gel electrophoresis experiment. The DNA transfer to bacterial cells mediated by the surfactant S1 is shown to depend on the protocol used. In the case of the electroporation, the inhibition of the cell transformation occurs in the presence of the surfactant, while upon the chemical treatment no surfactant effect has been observed. The variability in the morphology, the biocompatibility, the nanoscale dimension and the high binding capacity toward the DNA decamer make it possible to nominate the designed surfactants as promising carriers for biosubstrates or as a helper surfactant for the mixed liposome-surfactant nanocontainers.

  17. Two new natural products from Croton kongensis Gagnep.

    PubMed

    Sun, Lin; Meng, Zhaoqing; Li, Zhaoliang; Yang, Biao; Wang, Zhenzhong; Ding, Gang; Xiao, Wei

    2014-01-01

    A new diterpenoid, 14β-hydroxy-3-oxo-ent-kaur-16-ene (1), and a new nor-lignan, 8S-( - )-8-(4-hydroxy-3-methoxybenzoyl)-dihydrofuran-8(8'H)-one (4), along with five known compounds were isolated from the twigs and leaves of Croton kongensis Gagnep. Their isolations were clarified and structures were elucidated by the extensive spectroscopic analyses, especially 2D NMR experiments.

  18. Natural Language Processing.

    ERIC Educational Resources Information Center

    Chowdhury, Gobinda G.

    2003-01-01

    Discusses issues related to natural language processing, including theoretical developments; natural language understanding; tools and techniques; natural language text processing systems; abstracting; information extraction; information retrieval; interfaces; software; Internet, Web, and digital library applications; machine translation for…

  19. The nature and ethics of natural experiments.

    PubMed

    Dawson, Angus; Sim, Julius

    2015-10-01

    Natural experiments are an important methodology often used to answer research questions that would, otherwise, be impossible to address, or employed because of ethical concerns about the use of randomisation to interventions that carry known risks. The UK Medical Research Council (MRC) recently produced an extremely useful document discussing the nature and significance of natural experiments within medical and public health research. In this paper, however, we suggest that the MRC document's definition of the term 'natural experiment' is insufficiently precise. In response, we offer a taxonomy of different types of natural experiments and related methods, and explore the ethical implications of these different types. We argue that while the ethical issues that may arise within natural experiments in relation to risks of harm or informed consent may differ from those within the randomised controlled trial, they are not thereby less pressing. The implications of the argument are explored and recommendations made for those involved in research governance.

  20. Natural gas monthly

    SciTech Connect

    1998-01-01

    The Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the Natural Gas Monthly features articles designed to assist readers in using and interpreting natural gas information.

  1. Crystal structure and theoretical study of IR and 1H and 13C NMR spectra of cordatin, a natural product with antiulcerogenic activity

    NASA Astrophysics Data System (ADS)

    Brasil, Davi S. B.; Alves, Cláudio N.; Guilhon, Giselle M. S. P.; Muller, Adolfo H.; Secco, Ricardo De S.; Peris, Gabriel; Llusar, Rosa

    Cordatin is a furan diterpenoid with a clerodane skeleton isolated from Croton palanostigma Klotzsch (Euphorbiaceae). This natural product shows significant antiulcerogenic activity, similar to cimetidine (Tagamet®), a compound used for the treatment of peptic ulcers. The crystal structure of cordatin was obtained by X-ray diffraction and its geometrical parameters were compared with theoretical calculations at the B3LYP theory level. The IR and NMR (1H and 13C chemical shifts and coupling constants) spectra were obtained and compared with the theoretical calculations. The B3LYP theory level, with the 6-31G(d,p) and 6-311G(d,p) basis set, provided IR absorption values close to the experimental data. Moreover, theoretical NMR parameters obtained in both gas phase and chloroform solvent at the B3PW91/DGDZVP, B3LYP/6-311+G(2d,p), and B3PW91/6-311+G(2d,p) levels showed good correlations with the experimental results.

  2. The Nature of Natural Hazards Communication (Invited)

    NASA Astrophysics Data System (ADS)

    Kontar, Y. Y.

    2013-12-01

    Some of the many issues of interest to natural hazards professionals include the analysis of proactive approaches to the governance of risk from natural hazards and approaches to broaden the scope of public policies related to the management of risks from natural hazards, as well as including emergency and environmental management, community development and spatial planning related to natural hazards. During the talk we will present results of scientific review, analysis and synthesis, which emphasize same new trends in communication of the natural hazards theories and practices within an up-to-the-minute context of new environmental and climate change issues, new technologies, and a new focus on resiliency. The presentation is divided into five sections that focus on natural hazards communication in terms of education, risk management, public discourse, engaging the public, theoretical perspectives, and new media. It includes results of case studies and best practices. It delves into natural hazards communication theories, including diffusion, argumentation, and constructivism, to name a few. The presentation will provide information about: (1) A manual of natural hazards communication for scientists, policymakers, and media; (2) An up-to-the-minute context of environmental hazards, new technologies & political landscape; (3) A work by natural hazards scientists for geoscientists working with social scientists and communication principles; (4) A work underpinned by key natural hazards communication theories and interspersed with pragmatic solutions; (5) A work that crosses traditional natural hazards boundaries: international, interdisciplinary, theoretical/applied. We will further explore how spatial planning can contribute to risk governance by influencing the occupation of natural hazard-prone areas, and review the central role of emergency management in risk policy. The goal of this presentation is to contribute to the augmentation of the conceptual framework

  3. Overlapping elution-extrusion counter-current chromatography: a novel method for efficient purification of natural cytotoxic andrographolides from Andrographis paniculata.

    PubMed

    Wu, Dingfang; Cao, Xiaoji; Wu, Shihua

    2012-02-01

    Counter-current chromatography (CCC) is extremely useful for the separation, purification, and isolation of natural products. Recently, Berthod et al. established an elution-extrusion CCC method in metabolic analysis by combining regular chromatographic elution with stationary-phase extrusion, which extends the hydrophobicity window of a counter-current separation. In this study, a novel overlapping elution-extrusion CCC method was developed and applied to the preparation of natural cytotoxic andrographolides from the aerial parts of Andrographis paniculata, a well-known Traditional Chinese Medicine (TCM) with potent anti-inflammatory effect and anti-cancer activity. Its theory was first developed, and then a series of CCC experiments were performed to investigate the efficiency of the method in the separation of the ethanol extracts from A. paniculata. Results show that overlapping elution-extrusion CCC is an efficient method to prepare a cytotoxic natural diterpenoid combination of 14-deoxy-andrographolide and 14-deoxy-11,12-didehydroandrographolide with the molar ratio of 1:2 as well as andrographolide using an optimized solvent system composed of hexane-ethyl acetate-ethanol-water (5:5:4:6, v/v) with an on-demand solvent preparation mode. All components obtained showed potent cytotoxic activity against human hepatocellular liver carcinoma cells HepG2 and doxorubicin-resistant R-HepG2 cells. Molecular structures have been identified by electrospray ionization mass spectrometry (ESI-MS), electrospray ionization time-of-flight mass spectrometry (ESI-TOF-MS), one- and two-dimensional nuclear magnetic resonance (1D- and 2D-NMR). The method appears to be very useful for the high-throughput purification of natural products.

  4. Formulation of natural shampoos.

    PubMed

    Mainkar, A R; Jolly, C I

    2001-02-01

    Formulating cosmetics using completely natural raw materials is a difficult task. The challenge lies in selecting materials that can be rationally justified as 'natural' and formulating them into cosmetics whose functionality is comparable with their synthetic counterparts. The present paper focuses on the formulation of completely natural shampoos, their evaluation and comparison with commercial herbal shampoos. Attention is drawn to the fact that, due to the ambiguous definition of the word 'natural', several so-called natural cosmetics are available in the Indian market. It is up to the cosmetic chemists themselves to promote and encourage the development and use of truly natural cosmetics.

  5. Natural gas annual 1996

    SciTech Connect

    1997-09-01

    This document provides information on the supply and disposition of natural gas to a wide audience. The 1996 data are presented in a sequence that follows natural gas from it`s production to it`s end use.

  6. Demonstrating Natural Selection

    ERIC Educational Resources Information Center

    Hinds, David S.; Amundson, John C.

    1975-01-01

    Describes laboratory exercises with chickens selecting their food from dyed and natural corn kernels as a method of demonstrating natural selection. The procedure is based on the fact that organisms that blend into their surroundings escape predation. (BR)

  7. Natural Gas Monthly

    EIA Publications

    2016-01-01

    Highlights activities, events, and analyses associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer related activities and underground storage data are also reported.

  8. Colours From Nature

    ERIC Educational Resources Information Center

    Simon, Wilma

    1974-01-01

    In reference to American Indian ceremonial art, the importance of using natural pigments is emphasized, since the superior color values of natural dyes better reflect religious and philosophical depth and meaning. (JC)

  9. Nature's Nature: Ideas of Nature in Curricula for Environmental Education

    ERIC Educational Resources Information Center

    St Maurice, Henry

    2006-01-01

    Two contrasting sets of ideas about nature in environmental education are described. An analytical framework is developed from inter-disciplinary histories of ideas and used in evaluating a specific curriculum. In conclusion, some general implications are suggested for curricula in environmental education. [This article was reprinted from…

  10. Natural gas annual 1994

    SciTech Connect

    1995-11-17

    The Natural Gas Annual provides information on the supply and disposition of natural gas to a wide audience including industry, consumers, Federal and State agencies, and educational institutions. The 1994 data are presented in a sequence that follows natural gas (including supplemental supplies) from its production to its end use. This is followed by tables summarizing natural gas supply and disposition from 1990 to 1994 for each Census Division and each State. Annual historical data are shown at the national level.

  11. Natural gas annual 1995

    SciTech Connect

    1996-11-01

    The Natural Gas Annual provides information on the supply and disposition of natural gas to a wide audience including industry, consumers, Federal and State agencies, and educational institutions. The 1995 data are presented in a sequence that follows natural gas (including supplemental supplies) from its production to its end use. This is followed by tables summarizing natural gas supply and disposition from 1991 to 1995 for each Census Division and each State. Annual historical data are shown at the national level.

  12. Learning in Nature

    ERIC Educational Resources Information Center

    Brody, Michael

    2005-01-01

    This paper traces the evolution of a theory of learning in nature in order to explain how people learn in natural settings. The intellectual roots of the theory in informal learning, cognition, affective development, experiential and meaningful learning are described and the synthesis into a comprehensive theory of learning in nature are…

  13. Nature in the City.

    ERIC Educational Resources Information Center

    Ferbert, Mary Lou

    1981-01-01

    Describes a science program developed by the Cleveland Museum of Natural History, "Nature in the City," in which students and teachers learn together about the natural community surrounding their school. Includes program's rationale, list of "adventures," and methods. Discusses strategies of Sherlock Holmes'"adventure" focusing on animal tracks…

  14. Human nature and enhancement.

    PubMed

    Buchanan, Allen

    2009-03-01

    Appeals to the idea of human nature are frequent in the voluminous literature on the ethics of enhancing human beings through biotechnology. Two chief concerns about the impact of enhancements on human nature have been voiced. The first is that enhancement may alter or destroy human nature. The second is that if enhancement alters or destroys human nature, this will undercut our ability to ascertain the good because, for us, the good is determined by our nature. The first concern assumes that altering or destroying human nature is in itself a bad thing. The second concern assumes that human nature provides a standard without which we cannot make coherent, defensible judgments about what is good. I will argue (1) that there is nothing wrong, per se, with altering or destroying human nature, because, on a plausible understanding of what human nature is, it contains bad as well as good characteristics and there is no reason to believe that eliminating some of the bad would so imperil the good as to make the elimination of the bad impermissible, and (2) that altering or destroying human nature need not result in the loss of our ability to make judgments about the good, because we possess a conception of the good by which we can and do evaluate human nature. I will argue that appeals to human nature tend to obscure rather than illuminate the debate over the ethics of enhancement and can be eliminated in favor of more cogent considerations.

  15. Capturing Nature's Diversity

    PubMed Central

    Pascolutti, Mauro; Campitelli, Marc; Nguyen, Bao; Pham, Ngoc; Gorse, Alain-Dominique; Quinn, Ronald J.

    2015-01-01

    Natural products are universally recognized to contribute valuable chemical diversity to the design of molecular screening libraries. The analysis undertaken in this work, provides a foundation for the generation of fragment screening libraries that capture the diverse range of molecular recognition building blocks embedded within natural products. Physicochemical properties were used to select fragment-sized natural products from a database of known natural products (Dictionary of Natural Products). PCA analysis was used to illustrate the positioning of the fragment subset within the property space of the non-fragment sized natural products in the dataset. Structural diversity was analysed by three distinct methods: atom function analysis, using pharmacophore fingerprints, atom type analysis, using radial fingerprints, and scaffold analysis. Small pharmacophore triplets, representing the range of chemical features present in natural products that are capable of engaging in molecular interactions with small, contiguous areas of protein binding surfaces, were analysed. We demonstrate that fragment-sized natural products capture more than half of the small pharmacophore triplet diversity observed in non fragment-sized natural product datasets. Atom type analysis using radial fingerprints was represented by a self-organizing map. We examined the structural diversity of non-flat fragment-sized natural product scaffolds, rich in sp3 configured centres. From these results we demonstrate that 2-ring fragment-sized natural products effectively balance the opposing characteristics of minimal complexity and broad structural diversity when compared to the larger, more complex fragment-like natural products. These naturally-derived fragments could be used as the starting point for the generation of a highly diverse library with the scope for further medicinal chemistry elaboration due to their minimal structural complexity. This study highlights the possibility to capture a

  16. On nature and bioethics.

    PubMed

    Peterson, Paul Silas

    2010-01-01

    The account of nature and humanity's relationship to nature are of central importance for bioethics. The Scientific Revolution was a critical development in the history of this question and many contemporary accounts of nature find their beginnings here. While the innovative approach to nature going out of the seventeenth century was reliant upon accounts of nature from the early modern period, the Middle Ages, late-antiquity and antiquity, it also parted ways with some of the understandings of nature from these epochs. Here I analyze this development and suggests that some of the insights from older understandings of nature may be helpful for bioethics today, even if there can be no simple return to them.

  17. Nature, Education, and the Natural Woman

    ERIC Educational Resources Information Center

    Miller, Peter J.

    1974-01-01

    An examination of 18th and 19th century naturalistic educational theory reveals that appeals to nature confirmed and strengthened contemporary attitudes and practices restricting woman's access to knowledge and her freedom to make decisions and to act. (Author/DW)

  18. Human Nature and the Nature of Science.

    ERIC Educational Resources Information Center

    Stevens, Richard J.

    1988-01-01

    Examines the procedural and philosophical perspectives taken by science in examining human characteristics. Discusses the different levels of accuracy of various scientific fields. Encourages discussion of what biological and behavioral sciences can and cannot reveal about complex human nature. Considers some characteristics of quality science…

  19. Natural vacuum electronics

    NASA Technical Reports Server (NTRS)

    Leggett, Nickolaus

    1990-01-01

    The ambient natural vacuum of space is proposed as a basis for electron valves. Each valve is an electron controlling structure similiar to a vacuum tube that is operated without a vacuum sustaining envelope. The natural vacuum electron valves discussed offer a viable substitute for solid state devices. The natural vacuum valve is highly resistant to ionizing radiation, system generated electromagnetic pulse, current transients, and direct exposure to space conditions.

  20. Natural gas annual 1997

    SciTech Connect

    1998-10-01

    The Natural Gas Annual provides information on the supply and disposition of natural gas to a wide audience including industry, consumers, Federal and State agencies, and educational institutions. The 1997 data are presented in a sequence that follows natural gas (including supplemental supplies) from its production to its end use. This is followed by tables summarizing natural gas supply and disposition from 1993 to 1997 for each Census Division and each State. Annual historical data are shown at the national level. 27 figs., 109 tabs.

  1. A New Fungal Diterpene Induces VDAC1-dependent Apoptosis in Bax/Bak-deficient Cells.

    PubMed

    Huang, Li; Han, Junjie; Ben-Hail, Danya; He, Luwei; Li, Baowei; Chen, Ziheng; Wang, Yueying; Yang, Yanlei; Liu, Lei; Zhu, Yushan; Shoshan-Barmatz, Varda; Liu, Hongwei; Chen, Quan

    2015-09-25

    The pro-apoptotic Bax and Bak proteins are considered central to apoptosis, yet apoptosis occurs in their absence. Here, we asked whether the mitochondrial protein VDAC1 mediates apoptosis independently of Bax/Bak. Upon screening a fungal secondary metabolite library for compounds inducing apoptosis in Bax/Bak-deficient mouse embryonic fibroblasts, we identified cyathin-R, a new cyathane diterpenoid compound able to activate apoptosis in the absence of Bax/Bak via promotion of the VDAC1 oligomerization that mediates cytochrome c release. Diphenylamine-2-carboxilic acid, an inhibitor of VDAC1 conductance and oligomerization, inhibited cyathin-R-induced VDAC1 oligomerization and apoptosis. Similarly, Bcl-2 overexpression conferred resistance to cyathin-R-induced apoptosis and VDAC1 oligomerization. Silencing of VDAC1 expression prevented cyathin-R-induced apoptosis. Finally, cyathin-R effectively attenuated tumor growth and induced apoptosis in Bax/Bak-deficient cells implanted into a xenograft mouse model. Hence, this study identified a new compound promoting VDAC1-dependent apoptosis as a potential therapeutic option for cancerous cells lacking or presenting inactivated Bax/Bak.

  2. A New Fungal Diterpene Induces VDAC1-dependent Apoptosis in Bax/Bak-deficient Cells*

    PubMed Central

    Huang, Li; Han, Junjie; Ben-Hail, Danya; He, Luwei; Li, Baowei; Chen, Ziheng; Wang, Yueying; Yang, Yanlei; Liu, Lei; Zhu, Yushan; Shoshan-Barmatz, Varda; Liu, Hongwei; Chen, Quan

    2015-01-01

    The pro-apoptotic Bax and Bak proteins are considered central to apoptosis, yet apoptosis occurs in their absence. Here, we asked whether the mitochondrial protein VDAC1 mediates apoptosis independently of Bax/Bak. Upon screening a fungal secondary metabolite library for compounds inducing apoptosis in Bax/Bak-deficient mouse embryonic fibroblasts, we identified cyathin-R, a new cyathane diterpenoid compound able to activate apoptosis in the absence of Bax/Bak via promotion of the VDAC1 oligomerization that mediates cytochrome c release. Diphenylamine-2-carboxilic acid, an inhibitor of VDAC1 conductance and oligomerization, inhibited cyathin-R-induced VDAC1 oligomerization and apoptosis. Similarly, Bcl-2 overexpression conferred resistance to cyathin-R-induced apoptosis and VDAC1 oligomerization. Silencing of VDAC1 expression prevented cyathin-R-induced apoptosis. Finally, cyathin-R effectively attenuated tumor growth and induced apoptosis in Bax/Bak-deficient cells implanted into a xenograft mouse model. Hence, this study identified a new compound promoting VDAC1-dependent apoptosis as a potential therapeutic option for cancerous cells lacking or presenting inactivated Bax/Bak. PMID:26253170

  3. Introduction to Exploring Nature

    ERIC Educational Resources Information Center

    Early Childhood Today, 2006

    2006-01-01

    Children are fascinated with the world of nature. From the tiniest of seeds to the highest of birds, they wonder "Why?" "How?" and "What can I do with it?" This paper provides intriguing nature activities that provide a solid starting point for expanding children's thinking and learning. Through these activities, children will be building skills…

  4. Island Natural Science School.

    ERIC Educational Resources Information Center

    Toronto Board of Education (Ontario).

    Prepared for students in grade six attending the Island Natural Science School, Toronto, Ontario, Canada, this booklet offers information and suggests activities in the areas of ecology, conservation, natural resources, and outdoor recreation. Introductory material describes island lore, its formation and significant features, followed by units of…

  5. Modeling Natural Selection

    ERIC Educational Resources Information Center

    Bogiages, Christopher A.; Lotter, Christine

    2011-01-01

    In their research, scientists generate, test, and modify scientific models. These models can be shared with others and demonstrate a scientist's understanding of how the natural world works. Similarly, students can generate and modify models to gain a better understanding of the content, process, and nature of science (Kenyon, Schwarz, and Hug…

  6. On Teaching Natural Law.

    ERIC Educational Resources Information Center

    Forte, David F.

    1978-01-01

    A brief look at Columbia, Harvard, and Notre Dame law schools shows that the American tradition in teaching natural law has not been strong. The value of teaching natural law is discussed, a separate course or seminar is seen as the most effective option, and a selection of available sources for such a course is appended. (JMD)

  7. Nature of Science Is...

    ERIC Educational Resources Information Center

    Lederman, Judith Sweeney; Lederman, Norman G.

    2005-01-01

    The phrase "nature of science" refers to the characteristics of scientific knowledge that necessarily result from the scientific investigations that scientists conduct to develop knowledge. Yet, these characteristics are assumed by many to be "difficult" to teach. Not so. Many important aspects of nature of science can be directly linked to…

  8. Natural Science Centers: Directory.

    ERIC Educational Resources Information Center

    Natural Science for Youth Foundation, Roswell, GA.

    A nature center is defined as an organized and permanent nonprofit institution which is essentially educational, scientific, and cultural in purpose with professional staff, and open to the public on some regular schedule. A nature center manages and interprets its lands, native plants and animals and facilities to promote an understanding of…

  9. Nature's Advice Book

    ERIC Educational Resources Information Center

    Mahlin, Kathryn; Robertson, Amy

    2005-01-01

    What do can people learn from the world around them? Can a tree really teach something about life? Many times teachers provide students with facts about nature but fail to consider what one can learn from the natural world around them. After many months of exploring various ecosystems such as the prairie, rain forest, and desert, one of the…

  10. Geopolitics of natural gas

    SciTech Connect

    Russell, J.

    1983-01-01

    This examines the role of gas in the world energy supply/demand. Special attention is paid to Western Europe, the Soviet Union, and the natural gas exporting countries. Forecasts of global energy demand until 2000 and data on Western Europe's proven natural gas reserves as per January 1982 are provided.

  11. Nature Foil Reliefs

    ERIC Educational Resources Information Center

    Lane, Shaw J.

    2012-01-01

    Nature has always been a source of inspiration for artists across the centuries. Artists such as Leonardo da Vinci, Georgia O'Keeffe, Ansel Adams, and Andy Goldsworthy all drew inspiration for their work from nature. Seeds come from the dried pods, which when planted and cared for, bear fruit. In this article, the author describes how her…

  12. Birds. Nature Discovery I.

    ERIC Educational Resources Information Center

    Stone, Sally F.

    The birds of New England and their particular habitats are explored in this guide which is part of a series of Nature Discovery publications. The materials are designed to directly supplement the natural science curricula and to complement other subject areas including social studies, language arts, music, and art. The program is designed for…

  13. Research Component - Natural Sciences.

    ERIC Educational Resources Information Center

    Cooke, Donald

    The research component in the natural sciences does not have to be changed. Ninety-three percent of the students surveyed by Ann Heiss for her book "The Challenge to the Graduate Schools" felt that the research component of the natural sciences contributed to their scientific development, and 85 percent felt that it was intellectually stimulating.…

  14. Nature Experience and Education

    ERIC Educational Resources Information Center

    Rathunde, Kevin

    2013-01-01

    Kevin Rathunde turns his research lens to the task of finding out the relevance of the natural world, its impact on adolescent motivation, and its positive sustaining of concentration and focus. He cites "disembodiment and denaturing" as needing to be countered by contact with nature, leading to higher creativity, less drudgery, and more…

  15. Naturally occurring insecticides.

    PubMed Central

    Soloway, S B

    1976-01-01

    Naturally occurring insecticides are abundant and varied in their effects, though but a few are articles of commerce. Even for these, pyrethrum, nicotine, rotenone, hellebore, ryania, and sabadilla, there is a paucity of information on mammalian toxicology and environmental effects. In general, these materials are characterized favorably by low acute toxicity and ready dissipation in nature. Unfavorable aspects of natural insecticides are the contained mixture of active and inactive components and the low active ingredient content on a crop yield basis pointing to a high unit cost. Natural insecticides can serve additionally as leads to unnatural mimics, of which the commercially successful synthetic pyrethroids are prime examples. The chemical nature, relationship of insecticidal activity to chemical structure, occurrence, production, and utilization, registered uses, metabolism, and insect and mammalian toxicity are reviewed. PMID:789058

  16. Thermoacoustic natural gas liquefier

    SciTech Connect

    Swift, G.; Gardner, D.; Hayden, M.; Radebaugh, R.; Wollan, J.

    1996-07-01

    This is the final report of a two-year, Laboratory-Directed Research and Development (LDRD) project at the Los Alamos National Laboratory (LANL). This project sought to develop a natural-gas-powered natural-gas liquefier that has absolutely no moving parts and requires no electrical power. It should have high efficiency, remarkable reliability, and low cost. The thermoacoustic natural-gas liquefier (TANGL) is based on our recent invention of the first no-moving-parts cryogenic refrigerator. In short, our invention uses acoustic phenomena to produce refrigeration from heat, with no moving parts. The required apparatus comprises nothing more than heat exchangers and pipes, made of common materials, without exacting tolerances. Its initial experimental success in a small size lead us to propose a more ambitious application: large-energy liquefaction of natural gas, using combustion of natural gas as the energy source. TANGL was designed to be maintenance-free, inexpensive, portable, and environmentally benign.

  17. "Diseases and natural kinds".

    PubMed

    Sulmasy, Daniel P

    2005-01-01

    David Thomasma called for the development of a medical ethics based squarely on the philosophy of medicine. He recognized, however, that widespread anti-essentialism presented a significant barrier to such an approach. The aim of this article is to introduce a theory that challenges these anti-essentialist objections. The notion of natural kinds presents a modest form of essentialism that can serve as the basis for a foundationalist philosophy of medicine. The notion of a natural kind is neither static nor reductionistic. Disease can be understood as making necessary reference to living natural kinds without invoking the claim that diseases themselves are natural kinds. The idea that natural kinds have a natural disposition to flourish as the kinds of things that they are provides a telos to which to tether the notion of disease - an objective telos that is broader than mere survival and narrower than subjective choice. It is argued that while nosology is descriptive and may have therapeutic implications, disease classification is fundamentally explanatory. Sickness and illness, while referring to the same state of affairs, can be distinguished from disease phenomenologically. Scientific and diagnostic fallibility in making judgments about diseases do not diminish the objectivity of this notion of disease. Diseases are things, not kinds. Injury is a concept parallel to disease that also makes necessary reference to living natural kinds. These ideas provide a new possibility for the development of a philosophy of medicine with implications for medical ethics. PMID:16292605

  18. Living in cities, naturally.

    PubMed

    Hartig, Terry; Kahn, Peter H

    2016-05-20

    Natural features, settings, and processes in urban areas can help to reduce stress associated with urban life. In this and other ways, public health benefits from, street trees, green roofs, community gardens, parks and open spaces, and extensive connective pathways for walking and biking. Such urban design provisions can also yield ecological benefits, not only directly but also through the role they play in shaping attitudes toward the environment and environmental protection. Knowledge of the psychological benefits of nature experience supports efforts to better integrate nature into the architecture, infrastructure, and public spaces of urban areas.

  19. Living in cities, naturally.

    PubMed

    Hartig, Terry; Kahn, Peter H

    2016-05-20

    Natural features, settings, and processes in urban areas can help to reduce stress associated with urban life. In this and other ways, public health benefits from, street trees, green roofs, community gardens, parks and open spaces, and extensive connective pathways for walking and biking. Such urban design provisions can also yield ecological benefits, not only directly but also through the role they play in shaping attitudes toward the environment and environmental protection. Knowledge of the psychological benefits of nature experience supports efforts to better integrate nature into the architecture, infrastructure, and public spaces of urban areas. PMID:27199417

  20. Nature limits filarial transmission

    PubMed Central

    Chandra, Goutam

    2008-01-01

    Lymphatic filariasis, caused by Wuchereria bancrofti, Brugia malayi and B. timori is a public health problem of considerable magnitude of the tropics and subtropics. Presently 1.3 billion people are at risk of lymphatic filariasis (LF) infection and about 120 million people are affected in 83 countries. In this context it is worth mentioning that 'nature' itself limits filarial transmission to a great extent in a number of ways such as by reducing vector populations, parasitic load and many other bearings. Possibilities to utilize these bearings of natural control of filariasis should be searched and if manipulations on nature, like indiscriminate urbanization and deforestation, creating sites favourable for the breeding of filarial vectors and unsanitary conditions, water pollution with organic matters etc., are reduced below the threshold level, we will be highly benefited. Understandings of the factors related to natural phenomena of control of filariasis narrated in this article may help to adopt effective control strategies. PMID:18500974

  1. Natural gas monthly

    SciTech Connect

    1996-05-01

    This document highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Data presented include volume and price, production, consumption, underground storage, and interstate pipeline activities.

  2. Web life: Ask Nature

    NASA Astrophysics Data System (ADS)

    2012-11-01

    Ask Nature is a site devoted to biomimicry, an interdisciplinary field in which practitioners study how animals and plants solve problems, and then use those solutions to develop better human technologies.

  3. Is image steganography natural?

    PubMed

    Martín, Alvaro; Sapiro, Guillermo; Seroussi, Gadiel

    2005-12-01

    Steganography is the art of secret communication. Its purpose is to hide the presence of information, using, for example, images as covers. We experimentally investigate if stego-images, bearing a secret message, are statistically "natural." For this purpose, we use recent results on the statistics of natural images and investigate the effect of some popular steganography techniques. We found that these fundamental statistics of natural images are, in fact, generally altered by the hidden "nonnatural" information. Frequently, the change is consistently biased in a given direction. However, for the class of natural images considered, the change generally falls within the intrinsic variability of the statistics, and, thus, does not allow for reliable detection, unless knowledge of the data hiding process is taken into account. In the latter case, significant levels of detection are demonstrated.

  4. Make a Nature Trail

    ERIC Educational Resources Information Center

    Johnson, Janice K.

    1973-01-01

    Discusses the planning, construction, use, and maintenance of a nature trail. Ideal for demonstrating interrelationships between plants and animals, conservation practices, wildlife management, plant succession, forestry, geologic features and other scientific phenomena. (JR)

  5. The "Natural Law Tradition."

    ERIC Educational Resources Information Center

    Finnis, John

    1986-01-01

    A discussion of natural law outlines some of the theory and tradition surrounding it and examines its relationship to the social science and legal curriculum and to the teaching of jurisprudence. (MSE)

  6. Tifft Farm Nature Preserve.

    ERIC Educational Resources Information Center

    Benjamin, Thomas B.; Gannon, David J.

    1980-01-01

    Described are the creation, development, activities, and programs of Tifft Farm, a 264-acre nature preserve and environmental education center in Buffalo, New York, constructed on a sanitary landfill. (BT)

  7. Natural Gas Emergencies

    MedlinePlus

    ... by the Cass (ND) and Clay (MN) Emergency Planning Partnerships. Adapted with funding provided by Fargo Cass Public Health through the Cities Readiness Initiative (CRI) English – Natural Gas Emergencies - Last ...

  8. Nature's ups and downs

    NASA Astrophysics Data System (ADS)

    Rodgers, Peter

    2015-12-01

    When Norman Lockyer, an astronomer and science writer with a day job as a clerk at the War Office in London, approached the publishing house Macmillan and Company in 1869 with a proposal for a new weekly journal about science, few could have predicted the outcome. The journal in question was Nature, and given its influence over the past 146 years, it is hard to believe that Melinda Baldwin's Making Nature is the first full-length book to be written about it.

  9. [Natural toxin poisoning].

    PubMed

    Tsunematsu, Satoshi

    2012-08-01

    Natural toxin poisoning often occurs when amateur who has no expert knowledge of food collects and cooks the wrong material. In many cases, the symptoms of natural toxin poisoning are mild and the patients recover from illness within a day. However, if the patients have respiratory or neurological symptoms after several hours of intake, the patients must go to hospital immediately. Mushroom poisoning is often reported and puffer fish poisoning is sometimes reported in Japan.

  10. Lesson "Balance in Nature

    NASA Astrophysics Data System (ADS)

    Chapanova, V.

    2012-04-01

    Lesson "Balance in Nature" This simulation game-lesson (Balance in Nature) gives an opportunity for the students to show creativity, work independently, and to create models and ideas. It creates future-oriented thought connected to their experience, allowing them to propose solutions for global problems and personal responsibility for their activities. The class is divided in two teams. Each team chooses questions. 1. Question: Pollution in the environment. 2. Question: Care for nature and climate. The teams work on the chosen tasks. They make drafts, notes and formulate their solutions on small pieces of paper, explaining the impact on nature and society. They express their points of view using many different opinions. This generates alternative thoughts and results in creative solutions. With the new knowledge and positive behaviour defined, everybody realizes that they can do something positive towards nature and climate problems and the importance of individuals for solving global problems is evident. Our main goal is to recover the ecological balance, and everybody explains his or her own well-grounded opinions. In this work process the students obtain knowledge, skills and more responsible behaviour. This process, based on his or her own experience, dialogue and teamwork, helps the participant's self-development. Making the model "human↔ nature" expresses how human activities impact the natural Earth and how these impacts in turn affect society. Taking personal responsibility, we can reduce global warming and help the Earth. By helping nature we help ourselves. Teacher: Veselina Boycheva-Chapanova " Saint Patriarch Evtimii" Scholl Str. "Ivan Vazov"-19 Plovdiv Bulgaria

  11. Blackouts and natural risks

    NASA Astrophysics Data System (ADS)

    Danihelka, P.; Paldusová, E.; Dobeš, P.

    2009-04-01

    "Blackout" has become the common definition for the situation when electricity supply and demand are not balanced and security of supply fails. These failures have many impacts besides the lights going out, but this term is used commonly. Blackouts have drastic impacts for the society on whole and its citizens and some of them can influence big areas and last for long period, so the consequences are catastrophic. Even if at the European scale, the large extend blackouts are supposed to be exceptional, real frequency is relatively high, approximately once per two years. According to statistics, blackouts are often caused by natural causes, especially lightning. An example of lightning caused blackout is New York blackout 1977, leading to the stand-by of nuclear power plant Indian Point and with overall cost more than 300 mil. USD. There is a clear a distinction between those blackouts caused by nature and those that were caused by other faults. Usually, the nature-caused disturbances as Canada 1988, Sweden 2005 and France 1999, stay inside one country. However, their duration can extend to several weeks, and thus the costs of the interruptions and social impacts are high. Blackouts of only technologic and/or anthropogenic origin are frequently shorter, but may concern more end-users, when cascading from one country to another. Lightning is not the only natural event causing blackouts. Eighteen various case studies of blackout caused by natural events different then lightning were studied and following natural phenomenon found as a root causes: 1x forest fire, 1x snow calamity, 1x ice storm, 1x landslide, 1x high temperature, 1x geomagnetic storm, 2x earthquake, 2x inundation, 2x contact of line with trees, 6x storm (wind, hurricane…). We can conclude, that natural event are frequent cause of blackout of medium or large extend and this phenomena should be studied more in details. This contribution was supported by Ministry of Environment of the Czech Republic.

  12. Enhance Nature Exploration with Technology

    ERIC Educational Resources Information Center

    Holloway, Patricia; Mahan, Carol

    2012-01-01

    Kids and nature seem like a natural combination, but what was natural a generation ago is different today. Children are spending less time outdoors but continue to need nature for their physical, emotional, and mental development. This fact has led author Richard Louv to suggest that today's children are suffering from "nature-deficit disorder"…

  13. Natural photonic crystals

    NASA Astrophysics Data System (ADS)

    Vigneron, Jean Pol; Simonis, Priscilla

    2012-10-01

    Photonic structures appeared in nature several hundred millions years ago. In the living world, color is used for communication and this important function strongly impacts the individual chances of survival as well as the chances to reproduce. This has a statistical influence on species populations. Therefore, because they are involved in evolution, natural color-generating structures are - from some point of view - highly optimized. In this short review, a survey is presented of the development of natural photonic crystal-type structures occurring in insects, spiders, birds, fishes and other marine animals, in plants and more, from the standpoint of light-waves propagation. One-, two-, and three-dimensional structures will be reviewed with selected examples.

  14. Nature/culture/seawater.

    PubMed

    Helmreich, Stefan

    2011-01-01

    Seawater has occupied an ambiguous place in anthropological categories of "nature" and "culture." Seawater as nature appears as potentiality of form and uncontainable flux; it moves faster than culture - with culture frequently figured through land-based metaphors - even as culture seeks to channel water's (nature's) flow. Seawater as culture manifests as a medium of pleasure, sustenance, travel, disaster. I argue that, although seawater's qualities in early anthropology were portrayed impressionistically, today technical, scientific descriptions of water's form prevail. For example, processes of globalization - which may also be called "oceanization" - are often described as "currents," "flows," and "circulations." Examining sea-set ethnography, maritime anthropologies, and contemporary social theory, I propose that seawater has operated as a “theory machine” for generating insights about human cultural organization. I develop this argument with ethnography from the Sargasso Sea and in the Sea Islands. I conclude with a critique of appeals to water's form in social theory. PMID:21560270

  15. Reinventing Natural Selection

    NASA Astrophysics Data System (ADS)

    Geraedts, Caspar L.; Boersma, Kerst Th.

    2006-06-01

    Although many research studies report students’ Lamarckian misconceptions, only a few studies present learning and teaching strategies that focus on the successful development of the concept of natural selection. The learning and teaching strategy for upper secondary students (aged 15 16) presented in this study conducted in The Netherlands is based on the idea of guided reinvention, rather than on the conceptual change strategy. In guided reinvention, students reinvent the concept of natural selection by answering a sequence of questions based on the logical nature of Darwin’s theory. The results show that few Lamarckian explanations for evolution were recorded in the study and that the majority of the students developed a Darwinian or neo-Darwinian conception. The status of Lamarckian misconceptions is challenged.

  16. Explaining immigrant naturalization.

    PubMed

    Yang, P Q

    1994-01-01

    "Prior research on immigrant naturalization has focused mainly on the effects of immigrants' adaptation experiences and demographic characteristics on their propensity to naturalize. This article proposes a broader analytical framework which incorporates immigrants' individual characteristics and larger social contexts in the country of origin and the country of destination to explain the likelihood of citizenship acquisition. The framework is tested for a cohort of recent immigrants, using the PUMS data from the 1980 U.S. census. The results show that economic, political, social, cultural and geographical conditions in the country of origin, and immigrants ethnic communities and urban concentration in the country of destination, to a large extent influence immigrants' propensity for naturalization and that, net of the contextual factors, many of the immigrants' adaptation and demographic characteristics are also significant predictors of citizenship acquisition."

  17. Nature/culture/seawater.

    PubMed

    Helmreich, Stefan

    2011-01-01

    Seawater has occupied an ambiguous place in anthropological categories of "nature" and "culture." Seawater as nature appears as potentiality of form and uncontainable flux; it moves faster than culture - with culture frequently figured through land-based metaphors - even as culture seeks to channel water's (nature's) flow. Seawater as culture manifests as a medium of pleasure, sustenance, travel, disaster. I argue that, although seawater's qualities in early anthropology were portrayed impressionistically, today technical, scientific descriptions of water's form prevail. For example, processes of globalization - which may also be called "oceanization" - are often described as "currents," "flows," and "circulations." Examining sea-set ethnography, maritime anthropologies, and contemporary social theory, I propose that seawater has operated as a “theory machine” for generating insights about human cultural organization. I develop this argument with ethnography from the Sargasso Sea and in the Sea Islands. I conclude with a critique of appeals to water's form in social theory.

  18. Monitored natural attenuation.

    PubMed

    Jørgensen, Kirsten S; Salminen, Jani M; Björklöf, Katarina

    2010-01-01

    Monitored natural attenuation (MNA) is an in situ remediation technology that relies on naturally occurring and demonstrable processes in soil and groundwater which reduce the mass and concentration of the contaminants. Natural attenuation (NA) involves both aerobic and anaerobic degradation of the contaminants due to the fact that oxygen is used up near the core of the contaminant plume. The aerobic and anaerobic microbial processes can be assessed by microbial activity measurements and molecular biology methods in combination with chemical analyses. The sampling and knowledge on the site conditions are of major importance for the linkage of the results obtained to the conditions in situ. Rates obtained from activity measurements can, with certain limitations, be used in modeling of the fate of contaminants whereas most molecular methods mainly give qualitative information on the microbial community and gene abundances. However, molecular biology methods are fast and describe the in situ communities and avoid the biases inherent to activity assays requiring laboratory incubations.

  19. Brontides: natural explosive noises.

    PubMed

    Gold, T; Soter, S

    1979-04-27

    Episodes of explosive noises of natural origin, or brontides, have been well documented, often in association with seismic activity and in a few cases as precursors to major earthquakes. Ground-to-air acoustic transmission from shallow earthquakes can account for many of these episodes, but not for all, and other causes, such as the sudden eruption of gas from high-pressure sources in the ground may at times have been responsible. Confusion with distant thunder or artillery at times of anomalous sound propagation complicates the analysis, and more recently the greatly increased frequency of artificial explosive noises and sonic booms has tended to mask the recognition of natural brontides. PMID:17757998

  20. Natural environment analysis

    NASA Technical Reports Server (NTRS)

    Frost, W.

    1985-01-01

    The influence of terrain features on wind loading of the space shuttle while on the launch pad, or during early liftoff, was investigated both qualitatively and quantitatively. The climatology and meteorology producing macroscale wind patterns and characteristics for the Vandenburg Air Force Base launch site are described. Field test data are analyzed, and the nature and characteristic of flow disturbances due to the various terrain features, both natural and man-made, are reviewed. The magnitude of these wind loads are estimated. Finally, effects of turbulence are discussed. It is concluded that the influence of complex terrain can create significant wind loading on the vehicle.

  1. Naturally produced carbon nanotubes

    NASA Astrophysics Data System (ADS)

    Velasco-Santos, C.; Martínez-Hernández, A. L.; Consultchi, A.; Rodríguez, R.; Castaño, V. M.

    2003-05-01

    Carbon nanotubes represent an impressive kind of materials with diverse unexpected properties, and different methods to artificially produce them have been developed. Recently, they have also been synthesized at low temperatures, demonstrating that these materials might exist in fluids or carbon rocks of the Earth's crust. A new type of natural encapsulated carbon nanotubes found in a coal-petroleum mix is presented. These findings show that all allotropic carbon forms known up to date can be produced in Nature, where pressure, catalysts particles, shear stress and parameters other than exclusively very high temperature, seem to play an important role for producing nanotubes.

  2. Natural Cycles, Gases

    NASA Technical Reports Server (NTRS)

    Douglass, Anne R.; Jackman, Charles H.; Rood, R. B.; Aikin, A. C.; Stolarski, R. S.; Mccormick, M. P.; Fahey, David W.

    1992-01-01

    The major gaseous components of the exhaust of stratospheric aircraft are expected to be the products of combustion (CO2 and H2O), odd nitrogen (NO, NO2 HNO3), and products indicating combustion inefficiencies (CO and total unburned hydrocarbons). The species distributions are produced by a balance of photochemical and transport processes. A necessary element in evaluating the impact of aircraft exhaust on the lower stratospheric composition is to place the aircraft emissions in perspective within the natural cycles of stratospheric species. Following are a description of mass transport in the lower stratosphere and a discussion of the natural behavior of the major gaseous components of the stratospheric aircraft exhaust.

  3. Natural language modeling

    SciTech Connect

    Sharp, J.K.

    1997-11-01

    This seminar describes a process and methodology that uses structured natural language to enable the construction of precise information requirements directly from users, experts, and managers. The main focus of this natural language approach is to create the precise information requirements and to do it in such a way that the business and technical experts are fully accountable for the results. These requirements can then be implemented using appropriate tools and technology. This requirement set is also a universal learning tool because it has all of the knowledge that is needed to understand a particular process (e.g., expense vouchers, project management, budget reviews, tax, laws, machine function).

  4. Bacterial Diterpene Synthases: New Opportunities for Mechanistic Enzymology and Engineered Biosynthesis

    PubMed Central

    Smanski, Michael J.; Peterson, Ryan M.; Huang, Sheng-Xiong; Shen, Ben

    2012-01-01

    Diterpenoid biosynthesis has been extensively studied in plants and fungi, yet cloning and engineering diterpenoid pathways in these organisms remain challenging. Bacteria are emerging as prolific producers of diterpenoid natural products, and bacterial diterpene synthases are poised to make significant contributions to our understanding of terpenoid biosynthesis. Here we will first survey diterpenoid natural products of bacterial origin and briefly review their biosynthesis with emphasis on diterpene synthases (DTSs) that channel geranylgeranyl diphosphate to various diterpenoid scaffolds. We will then highlight differences of DTSs of bacterial and higher organism origins and discuss the challenges in discovering novel bacterial DTSs. We will conclude by discussing new opportunities for DTS mechanistic enzymology and applications of bacterial DTS in biocatalysis and metabolic pathway engineering. PMID:22445175

  5. Natural Freedom and Wilderness Survival

    ERIC Educational Resources Information Center

    Welton, George E.

    1978-01-01

    The "naturalism" of Jean Jacques Rousseau offers a philosophical base for wilderness survival: the renewal of participants in nature so that they can reenter civilization with a proper balance of natural and civil liberty. (MJB)

  6. The Nature of Diamonds

    NASA Astrophysics Data System (ADS)

    Harlow, George E.

    1997-10-01

    The paragon of physical perfection and a sparkling example of Earth's forces at work, the diamond has fascinated all realms of society, from starlets to scientists. The Nature of Diamonds is a comprehensive look at nature's most coveted gem. A handsome, large-format book, The Nature of Diamonds is an authoritative and richly-illustrated tribute to the diamond. Leading geologists, gemologists, physicists, and cultural observers cover every facet of the stone, from its formation in the depths of the Earth, its ascent to the surface, and its economic, regal, social, and technological roles. Cutting-edge research takes the reader to the frontiers of diamond exploration and exploitation, from the Arctic wastes to the laboratories where diamonds are created for massive road shredders that rip up and then re-create superhighways. Here also is an overview of cutting, from the rough stones in Roman rings to the highly-faceted stones we see today, and a glimpse into the business of diamonds. Finally, The Nature of Diamonds chronicles scientific and cultural history and explores the diamond as both a sacred and a social symbol, including a picture history of betrothal rings. Wide-ranging illustrations explain the geology of diamonds, chart the history of mining from its origins in India and Brazil through the diamond rush in South Africa and today's high-tech enterprises, and capture the brilliance and beauty of this extraordinary gem. _

  7. Nature as Inspiration

    ERIC Educational Resources Information Center

    Tank, Kristina; Moore, Tamara; Strnat, Meg

    2015-01-01

    This article describes the final lesson within a seven-day STEM and literacy unit that is part of the Picture STEM curriculum (pictureSTEM. org) and uses engineering to integrate science and mathematics learning in a meaningful way (Tank and Moore 2013). For this engineering challenge, students used nature as a source of inspiration for designs to…

  8. Picturing the Natural Environment

    ERIC Educational Resources Information Center

    Johnson, Phyllis Scott

    2011-01-01

    Around Scout Island Education Center, a site used by schools in Fresno County to explore the area's natural environment, a total of 200 cylinder-shaped concrete stools display tiles representing small mammals, flying insects, birds, wildflowers, and more. Twenty sets have been created by elementary, middle, and high-school art students as part of…

  9. Designing Nature's Way

    ERIC Educational Resources Information Center

    Fisher, Diane

    2005-01-01

    In the case of cars and other engineered objects, humans go about the design process in a very intentional way. They pretty much know what they are aiming for. The activity described in this article demonstrates how a computer can simulate biological evolution and the laws of natural selection. The article is divided into the following sections:…

  10. Picturing the Natural World

    ERIC Educational Resources Information Center

    Salia, Hannah

    2011-01-01

    How is the natural environment in the neighborhood representative of the larger biosphere in which people live? Studying the local birds and flora of the Pacific Northwest in the context of the local parks and ponds provided a rich opportunity for third-grade students at St. Thomas School in Medina, Washington, to explore and learn about…

  11. Reinventing Natural Selection

    ERIC Educational Resources Information Center

    Geraedts, Caspar L.; Boersma, Kerst Th.

    2006-01-01

    Although many research studies report students' Lamarckian misconceptions, only a few studies present learning and teaching strategies that focus on the successful development of the concept of natural selection. The learning and teaching strategy for upper secondary students (aged 15-16) presented in this study conducted in The Netherlands is…

  12. A Biospheric Natural History.

    ERIC Educational Resources Information Center

    Thomashow, Mitchell

    2001-01-01

    A group of Maine birdwatchers recognizes that the presence or absence of migrating songbirds is related to complex biospheric patterns. For schoolchildren, community groups, and environmental scientists, such local natural history observations can be a pathway to perceiving and understanding global ecological change and then to developing…

  13. Natural Gas Annual

    EIA Publications

    2015-01-01

    Provides information on the supply and disposition of natural gas in the United States. Production, transmission, storage, deliveries, and price data are published by state for the current year. Summary data are presented for each state for the previous 5 years.

  14. Nature in the City.

    ERIC Educational Resources Information Center

    Melber, Leah W.

    2000-01-01

    Presents three science activities targeted to help urban students learn about nature: (1) observing coloration patterns of pigeons; (2) measuring local rainfall and comparing it to other areas; and (3) conducting a biodiversity study by observing a patch of lawn. (YDS)

  15. Natural Gas Annual

    EIA Publications

    2016-01-01

    Provides information on the supply and disposition of natural gas in the United States. Production, transmission, storage, deliveries, and price data are published by state for the current year. Summary data are presented for each state for the previous 5 years.

  16. Radioactivity: A Natural Phenomenon.

    ERIC Educational Resources Information Center

    Ronneau, C.

    1990-01-01

    Discussed is misinformation people have on the subject of radiation. The importance of comparing artificial source levels of radiation to natural levels is emphasized. Measurements of radioactivity, its consequences, and comparisons between the risks induced by radiation in the environment and from artificial sources are included. (KR)

  17. The Nature of Atoms.

    ERIC Educational Resources Information Center

    Holden, Alan

    This monograph was written for the purpose of presenting physics to college students who are not preparing for careers in physics. It deals with the nature of atoms, and treats the following topics: (1) the atomic hypothesis, (2) the chemical elements, (3) models of an atom, (4) a particle in a one-dimensional well, (5) a particle in a central…

  18. Geopolitics of natural gas

    SciTech Connect

    Not Available

    1983-11-09

    With almost as many vital economic interests as there were attendees, two natural gas international conferences were held in North America during September and October, to share experience and forecasts. On September 26, the Canadian Energy Research Institute (CERI) and the Calgary Chamber of Commerce sponsored the International Gas Markets Conference and drew 400 persons. And on October 5-6, at the University of Colorado at Boulder, USA, the International Research Center for Energy and Economic Development (ICEED) held its Tenth International Energy Conference on Economic and Political Issues of Natural Gas in International Trade, drawing some 200 experts. The latter seminar was preceded by a two-day seminar on Asian Energy Supplies and Requirements, which also featured natural gas in many of its presentations. To provide an overview of some of these pressing questions, Energy Detente reports on these two comprehensive seminars on natural gas. This issue also presents the fuel price/tax series and the principal industrial fuel prices for the Eastern Hemisphere for November 1983.

  19. Precipitation: its acidic nature.

    PubMed

    Frohliger, J O; Kane, R

    1975-08-01

    A comparison of the free hydrogen ion concentration and the total hydrogen ion concentration of rain samples shows that rain is a weak acid. The weak acid nature of rain casts doubt on the concepts that the acidity of rain is increasing and that these increases are due to strong acids such as sulfuric acid.

  20. Gaia and natural selection.

    PubMed

    Lenton, T M

    1998-07-30

    Evidence indicates that the Earth self-regulates at a state that is tolerated by life, but why should the organisms that leave the most descendants be the ones that contribute to regulating their planetary environment? The evolving Gaia theory focuses on the feedback mechanisms, stemming from naturally selected traits of organisms, that could generate such self-regulation.

  1. Natural vegetation inventory

    NASA Technical Reports Server (NTRS)

    Schrumpf, B. J.

    1973-01-01

    Unique characteristics of ERTS imagery can be used to inventory natural vegetation. While satellite images can seldom be interpreted and identified directly in terms of vegetation types, such types can be inferred by interpretation of physical terrain features and through an understanding of the ecology of the vegetation.

  2. Natural Resources Education Notebook.

    ERIC Educational Resources Information Center

    Weber, Eldon C.

    This notebook was developed cooperatively by the United States Soil Conservation Service and Iowa State University to be used by teachers in providing instruction regarding certain aspects of natural resources. It includes four sections which provide: (1) an instructional plan about the conservation provisions of the 1985 Food Security Act; (2) an…

  3. Explaining Immigrant Naturalization.

    ERIC Educational Resources Information Center

    Yang, Philip Q.

    1994-01-01

    Proposes a broad analytical framework in the study of immigrant naturalization that incorporates an immigrant's individual characteristics with the larger social contexts in the country of origin and the country of destination to explain the likelihood of citizenship acquisition. Results testing of this framework show that such considerations are…

  4. Annatto: a natural choice.

    PubMed

    Evans, W C

    2000-09-01

    Annatto is a pigment derived from the seeds of Bixa orellana. It has been used from antiquity in South America and for over 100 years in Europe. It is now an important safe additive for a wide range of food, partly finding favour due to its natural origin. PMID:11153116

  5. Saving Natural Inflation

    SciTech Connect

    Croon, Djuna; Sanz, Verónica E-mail: v.sanz@sussex.ac.uk

    2015-02-01

    Slow-roll inflation requires the inflaton field to have an exceptionally flat potential, which combined with measurements of the scale of inflation demands some degree of fine-tuning. Alternatively, the flatness of the potential could be due to the inflaton's origin as a pseudo-Goldstone boson, as in Natural Inflation. Alas, consistency with Planck data places the original proposal of Natural Inflation in a tight spot, as it requires a trans-Planckian excursion of the inflaton. Although one can still tune the renormalizable potential to sub-Planckian values, higher order corrections from quantum gravity or sources of breaking of the Goldstone symmetry would ruin the predictivity of the model. In this paper we show how in more realistic models of Natural Inflation one could achieve inflation without a trans-Planckian excursion of the field. We show how a variant of Extra-natural inflation with bulk fermions can achieve the desired goal and discuss its four-dimensional duals. We also present a new type of four dimensional models inspired in Little Higgs and Composite Higgs models which can lead to sub-Planckian values of the inflaton field.

  6. Natural fracture systems studies

    SciTech Connect

    Lorenz, J.C.; Warpinski, N.R.

    1992-09-01

    The objectives of this program are (1) to develop a basinal-analysis methodology for natural fracture exploration and exploitation, and (2) to determine the important characteristics of natural fracture systems for use in completion, stimulation, and production operations. Natural-fracture basinal analysis begins with studies of fractures in outcrop, core and logs in order to determine the type of fracturing and the relationship of the fractures to the lithologic environment. Of particular interest are the regional fracture systems that are pervasive in western US tight sand basins. A Methodology for applying this analysis is being developed, with the goal of providing a structure for rationally characterizing natural fracture systems basin-wide. Such basin-wide characterizations can then be expanded and supplemented locally, at sites where production may be favorable. Initial application of this analysis is to the Piceance basin where there is a wealth of data from the Multiwell Experiment (MWX), DOE cooperative wells, and other basin studies conducted by Sandia, CER Corporation, and the USGS (Lorenz and Finley, 1989, Lorenz et aI., 1989, and Spencer and Keighin, 1984). Such a basinal approach has been capable of explaining the fracture characteristics found throughout the southern part of the Piceance basin and along the Grand Hogback.

  7. Demystifying Nature of Science

    ERIC Educational Resources Information Center

    Lederman, Judith; Bartels, Selina; Lederman, Norman; Gnanakkan, Dionysius

    2014-01-01

    With the emergence of the "Next Generation Science Standards" ("NGSS"; NGSS Lead States 2013), it is apparent that teaching and learning about nature of science (NOS) continues to be an important goal of science education for all K-12 students. With this emphasis on NOS, early childhood teachers are asking how to design…

  8. Nature, Education and Things

    ERIC Educational Resources Information Center

    Rømer, Thomas Aastrup

    2013-01-01

    In this essay it is argued that the educational philosophy of John Dewey gains in depth and importance by being related to his philosophy of nature, his metaphysics. The result is that any experiental process is situated inside an event, an existence, a thing, and I try to interpret this "thing" as schools or major cultural events such…

  9. Natural hazards science strategy

    USGS Publications Warehouse

    Holmes, Jr., Robert R.; Jones, Lucile M.; Eidenshink, Jeffery C.; Godt, Jonathan W.; Kirby, Stephen H.; Love, Jeffrey J.; Neal, Christina A.; Plant, Nathaniel G.; Plunkett, Michael L.; Weaver, Craig S.; Wein, Anne; Perry, Suzanne C.

    2012-01-01

    The mission of the U.S. Geological Survey (USGS) in natural hazards is to develop and apply hazard science to help protect the safety, security, and economic well-being of the Nation. The costs and consequences of natural hazards can be enormous, and each year more people and infrastructure are at risk. USGS scientific research - founded on detailed observations and improved understanding of the responsible physical processes - can help to understand and reduce natural hazard risks and to make and effectively communicate reliable statements about hazard characteristics, such as frequency, magnitude, extent, onset, consequences, and where possible, the time of future events. To accomplish its broad hazard mission, the USGS maintains an expert workforce of scientists and technicians in the earth sciences, hydrology, biology, geography, social and behavioral sciences, and other fields, and engages cooperatively with numerous agencies, research institutions, and organizations in the public and private sectors, across the Nation and around the world. The scientific expertise required to accomplish the USGS mission in natural hazards includes a wide range of disciplines that this report refers to, in aggregate, as hazard science. In October 2010, the Natural Hazards Science Strategy Planning Team (H-SSPT) was charged with developing a long-term (10-year) Science Strategy for the USGS mission in natural hazards. This report fulfills that charge, with a document hereinafter referred to as the Strategy, to provide scientific observations, analyses, and research that are critical for the Nation to become more resilient to natural hazards. Science provides the information that decisionmakers need to determine whether risk management activities are worthwhile. Moreover, as the agency with the perspective of geologic time, the USGS is uniquely positioned to extend the collective experience of society to prepare for events outside current memory. The USGS has critical statutory

  10. Natural products as photoprotection.

    PubMed

    Saewan, Nisakorn; Jimtaisong, Ampa

    2015-03-01

    The rise in solar ultraviolet radiation on the earth's surface has led to a depletion of stratospheric ozone over recent decades, thus accelerating the need to protect human skin against the harmful effects of UV radiation such as erythema, edema, hyperpigmentation, photoaging, and skin cancer. There are many different ways to protect skin against UV radiation's harmful effects. The most popular way to reduce the amount of UV radiation penetrating the skin is topical application of sunscreen products that contain UV absorbing or reflecting active molecules. Based on their protection mechanism, the active molecules in sunscreens are broadly divided into inorganic and organic agents. Inorganic sunscreens reflect and scatter UV and visible radiation, while organic sunscreens absorb UV radiation and then re-emit energy as heat or light. These synthetic molecules have limited concentration according to regulation concern. Several natural compounds with UV absorption property have been used to substitute for or to reduce the quantity of synthetic sunscreen agents. In addition to UV absorption property, most natural compounds were found to act as antioxidants, anti-inflammatory, and immunomodulatory agents, which provide further protection against the damaging effects of UV radiation exposure. Compounds derived from natural sources have gained considerable attention for use in sunscreen products and have bolstered the market trend toward natural cosmetics. This adds to the importance of there being a wide selection of active molecules in sunscreen formulations. This paper summarizes a number of natural products derived from propolis, plants, algae, and lichens that have shown potential photoprotection properties against UV radiation exposure-induced skin damage. PMID:25582033

  11. Natural products as photoprotection.

    PubMed

    Saewan, Nisakorn; Jimtaisong, Ampa

    2015-03-01

    The rise in solar ultraviolet radiation on the earth's surface has led to a depletion of stratospheric ozone over recent decades, thus accelerating the need to protect human skin against the harmful effects of UV radiation such as erythema, edema, hyperpigmentation, photoaging, and skin cancer. There are many different ways to protect skin against UV radiation's harmful effects. The most popular way to reduce the amount of UV radiation penetrating the skin is topical application of sunscreen products that contain UV absorbing or reflecting active molecules. Based on their protection mechanism, the active molecules in sunscreens are broadly divided into inorganic and organic agents. Inorganic sunscreens reflect and scatter UV and visible radiation, while organic sunscreens absorb UV radiation and then re-emit energy as heat or light. These synthetic molecules have limited concentration according to regulation concern. Several natural compounds with UV absorption property have been used to substitute for or to reduce the quantity of synthetic sunscreen agents. In addition to UV absorption property, most natural compounds were found to act as antioxidants, anti-inflammatory, and immunomodulatory agents, which provide further protection against the damaging effects of UV radiation exposure. Compounds derived from natural sources have gained considerable attention for use in sunscreen products and have bolstered the market trend toward natural cosmetics. This adds to the importance of there being a wide selection of active molecules in sunscreen formulations. This paper summarizes a number of natural products derived from propolis, plants, algae, and lichens that have shown potential photoprotection properties against UV radiation exposure-induced skin damage.

  12. Why Is Nature Beneficial?: The Role of Connectedness to Nature

    ERIC Educational Resources Information Center

    Mayer, F. Stephan; Frants, Cynthia McPherson; Bruehlman-Senecal, Emma; Dolliver, Kyffin

    2009-01-01

    Three studies examine the effects of exposure to nature on positive affect and ability to reflect on a life problem. Participants spent 15 min walking in a natural setting (Studies 1, 2, & 3), an urban setting (Study 1), or watching videos of natural and urban settings (Studies 2 & 3). In all three studies, exposure to nature increased…

  13. Natural light illumination system.

    PubMed

    Whang, Allen Jong-Woei; Chen, Yi-Yung; Yang, Shu-Hua; Pan, Po-Hsuan; Chou, Kao-Hsu; Lee, Yu-Chi; Lee, Zong-Yi; Chen, Chi-An; Chen, Cheng-Nan

    2010-12-10

    In recent years, green energy has undergone a lot of development and has been the subject of many applications. Many research studies have focused on illumination with sunlight as a means of saving energy and creating healthy lighting. Natural light illumination systems have collecting, transmitting, and lighting elements. Today, most daylight collectors use dynamic concentrators; these include Sun tracking systems. However, this design is too expensive to be cost effective. To create a low-cost collector that can be easily installed on a large building, we have designed a static concentrator, which is prismatic and cascadable, to collect sunlight for indoor illumination. The transmission component uses a large number of optical fibers. Because optical fibers are expensive, this means that most of the cost for the system will be related to transmission. In this paper, we also use a prismatic structure to design an optical coupler for coupling n to 1. With the n-to-1 coupler, the number of optical fibers necessary can be greatly reduced. Although this new natural light illumination system can effectively guide collected sunlight and send it to the basement or to other indoor places for healthy lighting, previously there has been no way to manage the collected sunlight when lighting was not desired. To solve this problem, we have designed an optical switch and a beam splitter to control and separate the transmitted light. When replacing traditional sources, the lighting should have similar characteristics, such as intensity distribution and geometric parameters, to those of traditional artificial sources. We have designed, simulated, and optimized an illumination lightpipe with a dot pattern to redistribute the collected sunlight from the natural light illumination system such that it equals the qualities of a traditional lighting system. We also provide an active lighting module that provides lighting from the natural light illumination system or LED auxiliary

  14. Design, science and naturalism

    NASA Astrophysics Data System (ADS)

    Deming, David

    2008-09-01

    The Design Argument is the proposition that the presence of order in the universe is evidence for the existence of God. The Argument dates at least to the presocratic Greek philosophers, and is largely based on analogical reasoning. Following the appearance of Aquinas' Summa Theologica in the 13th century, the Christian Church in Europe embraced a Natural Theology based on observation and reason that allowed it to dominate the entire world of knowledge. Science in turn advanced itself by demonstrating that it could be of service to theology, the recognized queen of the sciences. During the heyday of British Natural Theology in the 17th and 18th centuries, the watchmaker, shipbuilder, and architect analogies were invoked reflexively by philosophers, theologians, and scientists. The Design Argument was not systematically and analytically criticized until David Hume wrote Dialogues on Natural Religion in the 1750s. After Darwin published Origin of Species in 1859, Design withered on the vine. But in recent years, the Argument has been resurrected under the appellation "intelligent design," and been the subject of political and legal controversy in the United States. Design advocates have argued that intelligent design can be formulated as a scientific hypothesis, that new scientific discoveries validate a design inference, and that naturalism must be removed as a methodological requirement in science. If science is defined by a model of concentric epistemological zonation, design cannot be construed as a scientific hypothesis because it is inconsistent with the core aspects of scientific methodology: naturalism, uniformity, induction, and efficient causation. An analytical examination of claims by design advocates finds no evidence of any type to support either scientific or philosophical claims that design can be unambiguously inferred from nature. The apparent irreducible complexity of biological mechanisms may be explained by exaptation or scaffolding. The argument

  15. Hybrid Natural Inflation

    NASA Astrophysics Data System (ADS)

    Ross, Graham G.; Germán, Gabriel; Vázquez, J. Alberto

    2016-05-01

    We construct two simple effective field theory versions of Hybrid Natural Inflation (HNI) that illustrate the range of its phenomenological implications. The resulting inflationary sector potential, V = Δ4(1 + acos( ϕ/f)), arises naturally, with the inflaton field a pseudo-Nambu-Goldstone boson. The end of inflation is triggered by a waterfall field and the conditions for this to happen are determined. Also of interest is the fact that the slow-roll parameter ɛ (and hence the tensor r) is a non-monotonic function of the field with a maximum where observables take universal values that determines the maximum possible tensor to scalar ratio r. In one of the models the inflationary scale can be as low as the electroweak scale. We explore in detail the associated HNI phenomenology, taking account of the constraints from Black Hole production, and perform a detailed fit to the Planck 2015 temperature and polarisation data.

  16. Natural Products for Antithrombosis

    PubMed Central

    Chen, Cen; Zhang, Qian; Wang, Feng-Qin; Hu, Yuan-Jia; Xia, Zhi-Ning

    2015-01-01

    Thrombosis is considered to be closely related to several diseases such as atherosclerosis, ischemic heart disease and stroke, as well as rheumatoid arthritis, hyperuricemia, and various inflammatory conditions. More and more studies have been focused on understanding the mechanism of molecular and cellular basis of thrombus formation as well as preventing thrombosis for the treatment of thrombotic diseases. In reality, there is considerable interest in the role of natural products and their bioactive components in the prevention and treatment of thrombosis related disorders. This paper briefly describes the mechanisms of thrombus formation on three aspects, including coagulation system, platelet activation, and aggregation, and change of blood flow conditions. Furthermore, the natural products for antithrombosis by anticoagulation, antiplatelet aggregation, and fibrinolysis were summarized, respectively. PMID:26075003

  17. Natural gas repowering experience

    SciTech Connect

    Bautista, P.J.; Fay, J.M.; Gerber, F.B.

    1995-12-31

    Gas Research Institute has led a variety of projects in the past two years with respect to repowering with natural gas. These activities, including workshops, technology evaluations, and market assessments, have indicated that a significant opportunity for repowering exists. It is obvious that the electric power industry`s restructuring and the actual implementation of environmental regulations from the Clean Air Act Amendments will have significant impact on repowering with respect to timing and ultimate size of the market. This paper summarizes the results and implications of these activities in repowering with natural gas. It first addresses the size of the potential market and discusses some of the significant issues with respect to this market potential. It then provides a perspective on technical options for repowering which are likely to be competitive in the current environment. Finally, it addresses possible actions by the gas industry and GRI to facilitate development of the repowering market.

  18. Responses to natural disasters

    NASA Astrophysics Data System (ADS)

    Maggs, William Ward

    Since 1964, natural disasters caused by earthquakes, volcanic eruptions, or extreme weather in the form of floods, droughts, or hurricanes, have been responsible for more than 2,756,000 deaths worldwide in nations other than the United States, the Soviet Union, and the Eastern European Bloc, according to figures tabulated by the Office of Foreign Disaster Assistance (OFDA) of the Agency for International Development (AID). Over 95% of these fatalities occurred in developing or third world countries. Damage resulting from these calamities has been severe but extremely difficult to estimate in monetary terms. In 1986, U.S. government and voluntary agencies spent $303 million on natural disaster assistance around the world, 79% of total world assistance. In 1985 the U.S. total was nearly $900 million, 48% of the $1.84 billion world total.

  19. Safer Liquid Natural Gas

    NASA Technical Reports Server (NTRS)

    1976-01-01

    After the disaster of Staten Island in 1973 where 40 people were killed repairing a liquid natural gas storage tank, the New York Fire Commissioner requested NASA's help in drawing up a comprehensive plan to cover the design, construction, and operation of liquid natural gas facilities. Two programs are underway. The first transfers comprehensive risk management techniques and procedures which take the form of an instruction document that includes determining liquid-gas risks through engineering analysis and tests, controlling these risks by setting up redundant fail safe techniques, and establishing criteria calling for decisions that eliminate or accept certain risks. The second program prepares a liquid gas safety manual (the first of its kind).

  20. [Secrets of nature].

    PubMed

    Molnar, Michael

    2010-01-01

    The article examines a group photograph of the Psychiatry and Neurology section of the 66th Meeting of the Society of German Natural Scientists and Doctors in Vienna, September 24-30, 1894 which Sigmund Freud attended. The society's origins in Naturphilosophie are indicated and a number of the participants are identified on the photo. They and the events at the conference are related to Sigmund Freud's work at the time and to his gradual abandonment of anatomy, and of heredity and degeneration as significant aetiological factors in the neuroses. Philosophical problems, such as how phenomena should be described and how "nature" is conceptualized, are also considered in the light of their implications for Freud's life and thought at that period.

  1. Naturally selecting solutions

    PubMed Central

    Manning, Timmy; Sleator, Roy D; Walsh, Paul

    2013-01-01

    For decades, computer scientists have looked to nature for biologically inspired solutions to computational problems; ranging from robotic control to scheduling optimization. Paradoxically, as we move deeper into the post-genomics era, the reverse is occurring, as biologists and bioinformaticians look to computational techniques, to solve a variety of biological problems. One of the most common biologically inspired techniques are genetic algorithms (GAs), which take the Darwinian concept of natural selection as the driving force behind systems for solving real world problems, including those in the bioinformatics domain. Herein, we provide an overview of genetic algorithms and survey some of the most recent applications of this approach to bioinformatics based problems. PMID:23222169

  2. Notes on natural inflation

    NASA Astrophysics Data System (ADS)

    Yonekura, Kazuya

    2014-10-01

    In the so-called natural inflation, an axion-like inflaton is assumed to have a cosine-type periodic potential. This is not the case in a very simple model in which the axion-like inflaton is coupled to an SU(N) (or other) pure Yang-Mills, at least in the large N limit as pointed out by Witten. It has a multi-valued potential, which is effectively quadratic, i.e., there is only a mass term in the large N limit. Thanks to this property, chaotic inflation can be realized more naturally with the decay constant of the axion-like inflaton less than the Planck scale. We demonstrate these points explicitly by using softly broken Script N=1 Super-Yang-Mills which allows us to treat finite N. This analysis also suggests that moderately large gauge groups such as E8 are good enough with a Planck scale decay constant.

  3. The natural holistic imperative.

    PubMed

    Kermode, Stephen

    2002-10-01

    Biodiversity is nature's expression of the principle of holism. This 'natural holistic imperative' is manifested in all aspects of the environment. While environmental health originated through a concern for protecting humans from environmental risks, it is now concerned with protecting the environment from the activities of humans. In order to protect the health of humans, there is a need to be concerned with protection of the biosphere. Moreover, the environmental crisis is essentially a crisis in spirituality, and a spirituality that respects and nurtures the non-human parts of our universe as much as it does the human ones is likely to be the only means of securing the health and happiness of humanity.

  4. Great natural gas swindle

    SciTech Connect

    Karkkainen, B.

    1981-07-01

    The Citizen/Labor Energy Coalition (C/LEC) is challenging natural gas deregulation bids by oil companies, which control 70% of domestic gas production, that will double or triple costs to consumers by 1985. Price increases will affect the cost of consumer goods, food, and several basic industries as well as residential heating bills. C/LEC disagrees with the Reagan administration that decontrol is needed to encourage production because this did not happen with the incentives provided by the Natural Gas Policy Act. Conservation will not be affected either because the capital needed for conservation investment will be used for higher gas bills. With higher employment another direct result, the only beneficiaries of decontrol appear to be the producers. (DCK)

  5. Natural environment analysis

    NASA Technical Reports Server (NTRS)

    1985-01-01

    Qualitative analyses (and quantitatively to the extend possible) of the influence of terrain features on wind loading of the space shuttle while on the launch pad, or during early liftoff, are presented. Initially, the climatology and meteorology producing macroscale wind patterns and characteristics fot he Vandenburg Air Force Base (VAFB) launch site are described. Also, limited field test data are analyzed, and then the nature and characteristic of flow disturbances due to the various terrain features, both natural and man-made, are then reviewed. Following this, the magnitude of these wind loads are estimated. Finally, effects of turbulence are discussed. The study concludes that the influence of complex terrain can create significant wind loading on the vehicle. Because of the limited information, it is not possible to quantify the magnitude of these loads.

  6. Principles of Natural Photosynthesis.

    PubMed

    Krewald, Vera; Retegan, Marius; Pantazis, Dimitrios A

    2016-01-01

    Nature relies on a unique and intricate biochemical setup to achieve sunlight-driven water splitting. Combined experimental and computational efforts have produced significant insights into the structural and functional principles governing the operation of the water-oxidizing enzyme Photosystem II in general, and of the oxygen-evolving manganese-calcium cluster at its active site in particular. Here we review the most important aspects of biological water oxidation, emphasizing current knowledge on the organization of the enzyme, the geometric and electronic structure of the catalyst, and the role of calcium and chloride cofactors. The combination of recent experimental work on the identification of possible substrate sites with computational modeling have considerably limited the possible mechanistic pathways for the critical O-O bond formation step. Taken together, the key features and principles of natural photosynthesis may serve as inspiration for the design, development, and implementation of artificial systems. PMID:26099285

  7. Natural convective mixing flows

    NASA Astrophysics Data System (ADS)

    Ramos, Eduardo; de La Cruz, Luis; del Castillo, Luis

    1998-11-01

    Natural convective mixing flows. Eduardo Ramos and Luis M. de La Cruz, National University of Mexico and Luis Del Castillo San Luis Potosi University. The possibility of mixing a fluid with a natural convective flow is analysed by solving numerically the mass, momentum and energy equations in a cubic container. Two opposite vertical walls of the container are assumed to have temperatures that oscillate as functions of time. The phase of the oscillations is chosen in such a way that alternating corrotating vortices are formed in the cavity. The mixing efficiency of this kind of flow is examined with a Lagrangian tracking technique. This work was partially financed by CONACyT-Mexico project number GE0044

  8. Reasons to Conserve Nature.

    PubMed

    Pearson, Richard G

    2016-05-01

    Is it sufficient to base arguments for conservation on the intrinsic value of nature, regardless of the services and economic benefits that biodiversity provides for humans? This question underlies much recent debate that has been at times acrimonious and has led to calls for a more inclusive approach to conservation. Yet melding different ideologies within a unified conceptual framework has proven difficult. Here I describe an approach that recognizes the importance of the level of biological organization and spatial extent in determining the strength of alternative arguments for why we should conserve nature. I argue that the framework helps reconcile contrasting viewpoints and brings clarity to when different conservation management approaches (for instance, regulation versus monetary valuation) are most appropriate. PMID:26936225

  9. Epidemics after Natural Disasters

    PubMed Central

    Gayer, Michelle; Connolly, Maire A.

    2007-01-01

    The relationship between natural disasters and communicable diseases is frequently misconstrued. The risk for outbreaks is often presumed to be very high in the chaos that follows natural disasters, a fear likely derived from a perceived association between dead bodies and epidemics. However, the risk factors for outbreaks after disasters are associated primarily with population displacement. The availability of safe water and sanitation facilities, the degree of crowding, the underlying health status of the population, and the availability of healthcare services all interact within the context of the local disease ecology to influence the risk for communicable diseases and death in the affected population. We outline the risk factors for outbreaks after a disaster, review the communicable diseases likely to be important, and establish priorities to address communicable diseases in disaster settings. PMID:17370508

  10. Biofouling: lessons from nature.

    PubMed

    Bixler, Gregory D; Bhushan, Bharat

    2012-05-28

    Biofouling is generally undesirable for many applications. An overview of the medical, marine and industrial fields susceptible to fouling is presented. Two types of fouling include biofouling from organism colonization and inorganic fouling from non-living particles. Nature offers many solutions to control fouling through various physical and chemical control mechanisms. Examples include low drag, low adhesion, wettability (water repellency and attraction), microtexture, grooming, sloughing, various miscellaneous behaviours and chemical secretions. A survey of nature's flora and fauna was taken in order to discover new antifouling methods that could be mimicked for engineering applications. Antifouling methods currently employed, ranging from coatings to cleaning techniques, are described. New antifouling methods will presumably incorporate a combination of physical and chemical controls.

  11. Notes on natural inflation

    SciTech Connect

    Yonekura, Kazuya

    2014-10-01

    In the so-called natural inflation, an axion-like inflaton is assumed to have a cosine-type periodic potential. This is not the case in a very simple model in which the axion-like inflaton is coupled to an SU(N) (or other) pure Yang–Mills, at least in the large N limit as pointed out by Witten. It has a multi-valued potential, which is effectively quadratic, i.e., there is only a mass term in the large N limit. Thanks to this property, chaotic inflation can be realized more naturally with the decay constant of the axion-like inflaton less than the Planck scale. We demonstrate these points explicitly by using softly broken N=1 Super-Yang-Mills which allows us to treat finite N. This analysis also suggests that moderately large gauge groups such as E{sub 8} are good enough with a Planck scale decay constant.

  12. Nature's Greatest Puzzles

    SciTech Connect

    Quigg, Chris; /Fermilab

    2005-02-01

    It is a pleasure to be part of the SLAC Summer Institute again, not simply because it is one of the great traditions in our field, but because this is a moment of great promise for particle physics. I look forward to exploring many opportunities with you over the course of our two weeks together. My first task in talking about Nature's Greatest Puzzles, the title of this year's Summer Institute, is to deconstruct the premise a little bit.

  13. Natural and artificial tanning.

    PubMed

    Clore, E R

    1995-01-01

    Although sunlight is beneficial to provide light and warmth and aids the body in the formation of vitamin D, tanning is potentially damaging to an individual's health. The incidence of skin cancer and retinal damage from both natural and artificial light is on the rise. This article explores the concept of tanning, types of ultraviolet rays and related health hazards. Health care provider interventions for prevention and client education are also emphasized.

  14. Thermoacoustic natural gas liquefier

    SciTech Connect

    Swift, G.W.

    1997-05-01

    Cryenco and Los Alamos are collaborating to develop a natural-gas-powered natural-gas liquefier that will have no moving parts and require no electrical power. It will have useful efficiency, remarkable reliability, and low cost. The liquefaction of natural gas, which occurs at only 115 Kelvin at atmospheric pressure, has previously required rather sophisticated refrigeration machinery. The 1990 invention of the thermoacoustically driven orifice pulse-tube refrigerator (TA-DOPTR) provides cryogenic refrigeration with no moving parts for the first time. In short, this invention uses acoustic phenomena to produce refrigeration from heat. The required apparatus consists of nothing more than helium-filled heat exchangers and pipes, made of common materials, without exacting tolerances. In the Cryenco-Los Alamos collaboration, the authors are developing a version of this invention suitable for use in the natural-gas industry. The project is known as acoustic liquefier for short. The present program plans call for a two-phase development. Phase 1, with capacity of 500 gallon per day (i.e., approximately 40,000 scfd, requiring a refrigeration power of about 7 kW), is large enough to illuminate all the issues of large-scale acoustic liquefaction without undue cost, and to demonstrate the liquefaction of 60--70% of input gas, while burning 30--40%. Phase 2 will target versions of approximately 10{sup 6} scfd = 10,000 gallon per day capacity. In parallel with both, they continue fundamental research on the technology, directed toward increased efficiency, to build scientific foundations and a patent portfolio for future acoustic liquefiers.

  15. Geomorphology and natural hazards

    NASA Astrophysics Data System (ADS)

    Gares, Paul A.; Sherman, Douglas J.; Nordstrom, Karl F.

    1994-08-01

    Natural hazards research was initiated in the 1960's by Gilbert White and his students who promulgated a research paradigm that involved assessing risk from a natural event, identifying adjustments to cope with the hazard, determining people's perception of the event, defining the process by which people choose adjustments, and estimating the effects of public policy on the choice process. Studies of the physical system played an important role in early research, but criticismsof the paradigm resulted in a shift to a prominence of social science. Geomorphologists are working to fill gaps in knowledge of the physical aspects of individual hazards, but use of the information by social scientists will only occur if information is presented in a format that is useful to them. One format involves identifying the hazard according to seven physical parameters established by White and his colleagues: magnitude, frequency, duration, areal extent, speed of onset, spatial dispersion, and temporal spacing. Geomorphic hazards are regarded as related to landscape changes that affect human systems. The processes that produce the changes are rarely geomorphic in nature, but are better regarded as atmospheric or hydrologic. An examination of geomorphic hazards in four fields — soil erosion, mass movement, coastal erosion and fluvial erosion — demonstrates that advances in those fields may be evaluated in terms of the seven parameters. Geomorphologists have contributed to hazard research by focusing on the dynamics of the landforms. The prediction of occurence, the determination of spatial and temporal characteristics, the impact of physical characteristics on people's perception, and the impact of physical characteristics on adjustment formulation. Opportunities for geomorphologists to improve our understanding of geomorphic hazards include research into the characteristics of the events particularly with respect to predicting the occurence, and increased evaluation of the

  16. Natural Underwater Adhesives

    PubMed Central

    Stewart, Russell J.; Ransom, Todd C.; Hlady, Vladimir

    2011-01-01

    The general topic of this review is protein-based underwater adhesives produced by aquatic organisms. The focus is on mechanisms of interfacial adhesion to native surfaces and controlled underwater solidification of natural water-borne adhesives. Four genera that exemplify the broad range of function, general mechanistic features, and unique adaptations are discussed in detail: blue mussels, acorn barnacles, sandcastle worms, and freshwater caddisfly larva. Aquatic surfaces in nature are charged and in equilibrium with their environment, populated by an electrical double layer of ions as well as adsorbed natural polyelectrolytes and microbial biofilms. Surface adsorption of underwater bioadhesives likely occurs by exchange of surface bound ligands by amino acid sidechains, driven primarily by relative affinities and effective concentrations of polymeric functional groups. Most aquatic organisms exploit modified amino acid sidechains, in particular phosphorylated serines and hydroxylated tyrosines (dopa), with high-surface affinity that form coordinative surface complexes. After delivery to the surfaces as a fluid, permanent natural adhesives solidify to bear sustained loads. Mussel plaques are assembled in a manner superficially reminiscent of in vitro layer-by-layer strategies, with sequentially delivered layers associated through Fe(dopa)3 coordination bonds. The adhesives of sandcastle worms, caddisfly larva, and barnacles may be delivered in a form somewhat similar to in vitro complex coacervation. Marine adhesives are secreted, or excreted, into seawater that has a significantly higher pH and ionic strength than the internal environment. Empirical evidence suggests these environment triggers could provide minimalistic, fail-safe timing mechanisms to prevent premature solidification (insolubilization) of the glue within the secretory system, yet allow rapid solidification after secretion. Underwater bioadhesives are further strengthened by secondary covalent

  17. Microflyers: inspiration from nature

    NASA Astrophysics Data System (ADS)

    Sirohi, Jayant

    2013-04-01

    Over the past decade, there has been considerable interest in miniaturizing aircraft to create a class of extremely small, robotic vehicles with a gross mass on the order of tens of grams and a dimension on the order of tens of centimeters. These are collectively refered to as micro aerial vehicles (MAVs) or microflyers. Because the size of microflyers is on the same order as that of small birds and large insects, engineers are turning to nature for inspiration. Bioinspired concepts make use of structural or aerodynamic mechanisms that are observed in insects and birds, such as elastic energy storage and unsteady aerodynamics. Biomimetic concepts attempt to replicate the form and function of natural flyers, such as flapping-wing propulsion and external appearance. This paper reviews recent developments in the area of man-made microflyers. The design space for microflyers will be described, along with fundamental physical limits to miniaturization. Key aerodynamic phenomena at the scale of microflyers will be highlighted. Because the focus is on bioinspiration and biomimetics, scaled-down versions of conventional aircraft, such as fixed wing micro air vehicles and microhelicopters will not be addressed. A few representative bioinspired and biomimetic microflyer concepts developed by researchers will be described in detail. Finally, some of the sensing mechanisms used by natural flyers that are being implemented in man-made microflyers will be discussed.

  18. Future natural gas supplies

    NASA Astrophysics Data System (ADS)

    Despite recent optimism about the outlook for the future supply of domestic conventional natural gas, the Congressional Office of Technology Assessment (OTA) finds insufficient evidence to clearly justify either an optimistic or a pessimistic view. In a technical memorandum entitled “U.S. Natural Gas Availability: Conventional Gas Supply Through the Year 2000,” released recently by Rep. Philip R. Sharp (D-Ind,), chairman of the Subcommittee on Fossil and Synthetic Fuels of the Committee on Energy and Commerce, OTA concluded that substantial technical uncertainties prevented a reliable estimation of the likely natural gas production rates for later in this century. Even ignoring the potential for significant changes in gas prices and technology, OTA estimated that conventional gas production by the lower 48 states in the year 2000 could range from 9 to 19 trillion cubic feet (TCF) (0.25 to 0.53 trillion cubic meters), compared to 1982 production of 17.5 TCF. Similarly, production in the year 1990 could range from 13 to 20 TCF.

  19. Natural language generation

    NASA Astrophysics Data System (ADS)

    Maybury, Mark T.

    The goal of natural language generation is to replicate human writers or speakers: to generate fluent, grammatical, and coherent text or speech. Produced language, using both explicit and implicit means, must clearly and effectively express some intended message. This demands the use of a lexicon and a grammar together with mechanisms which exploit semantic, discourse and pragmatic knowledge to constrain production. Furthermore, special processors may be required to guide focus, extract presuppositions, and maintain coherency. As with interpretation, generation may require knowledge of the world, including information about the discourse participants as well as knowledge of the specific domain of discourse. All of these processes and knowledge sources must cooperate to produce well-written, unambiguous language. Natural language generation has received less attention than language interpretation due to the nature of language: it is important to interpret all the ways of expressing a message but we need to generate only one. Furthermore, the generative task can often be accomplished by canned text (e.g., error messages or user instructions). The advent of more sophisticated computer systems, however, has intensified the need to express multisentential English.

  20. Natural death while driving.

    PubMed

    Oström, M; Eriksson, A

    1987-07-01

    Of sudden natural deaths while driving, 126 occurred during 1980 through 1985 in the northern half of Sweden. The mean age of the 69 car driver victims was 59 years, considerably higher than that of traumatic car deaths, and all but 2 were males. The mean age of 57 operators of other vehicles was 66 years, and of these, 6 were women. Seven car drivers were stricken during commercial employment. Most accidents occurred during daytime and the distribution of the weekdays was fairly even. Ischemic heart disease accounted for 112 deaths, and other cardiovascular diseases for an additional 9 deaths. Only 1/5 of the victims experienced previous symptoms of disease. Out of at least 31 other persons at risk in the car deaths, only 2 passengers suffered minor injuries. The trauma in the deceased was in most cases minor in both car and other vehicle deaths. Property damage was also minimal. At least 1/3 of the drivers were able to stop the car before becoming unconscious. In none of the car cases was alcohol detected in the blood, while alcohol was identified in at least 2 of the other vehicle victims. The findings here agree with previous studies that natural deaths at the wheel are fairly uncommon, and that the risk for other persons is not significant. The value of adequate postmortem examinations of drivers dying in traffic is stressed--natural deaths can otherwise be overlooked. PMID:3612079

  1. NATURAL RESOURCES ASSESSMENT

    SciTech Connect

    D.F. Fenster

    2000-12-11

    The purpose of this report is to summarize the scientific work that was performed to evaluate and assess the occurrence and economic potential of natural resources within the geologic setting of the Yucca Mountain area. The extent of the regional areas of investigation for each commodity differs and those areas are described in more detail in the major subsections of this report. Natural resource assessments have focused on an area defined as the ''conceptual controlled area'' because of the requirements contained in the U.S. Nuclear Regulatory Commission Regulation, 10 CFR Part 60, to define long-term boundaries for potential radionuclide releases. New requirements (proposed 10 CFR Part 63 [Dyer 1999]) have obviated the need for defining such an area. However, for the purposes of this report, the area being discussed, in most cases, is the previously defined ''conceptual controlled area'', now renamed the ''natural resources site study area'' for this report (shown on Figure 1). Resource potential can be difficult to assess because it is dependent upon many factors, including economics (demand, supply, cost), the potential discovery of new uses for resources, or the potential discovery of synthetics to replace natural resource use. The evaluations summarized are based on present-day use and economic potential of the resources. The objective of this report is to summarize the existing reports and information for the Yucca Mountain area on: (1) Metallic mineral and mined energy resources (such as gold, silver, etc., including uranium); (2) Industrial rocks and minerals (such as sand, gravel, building stone, etc.); (3) Hydrocarbons (including oil, natural gas, tar sands, oil shales, and coal); and (4) Geothermal resources. Groundwater is present at the Yucca Mountain site at depths ranging from 500 to 750 m (about 1,600 to 2,500 ft) below the ground surface. Groundwater resources are not discussed in this report, but are planned to be included in the hydrology

  2. Antimicrobial and antiparastic abietane diterpenoids from Cupressus sempervirens

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Cupressus sempervirens L. (Cupressaceae) is a species of cypress native to the eastern Mediterranean region. The ethanol extract of the powdered cone (fruits) of this plant, collected from Oxford, Mississippi, USA during the fall of 2010, exhibited potent antimicrobial and antiparastic a...

  3. 8,15-epoxylabdane and norlabdane diterpenoids from Eragrostis viscosa.

    PubMed

    Sebastião, N'Soki N; Cordeiro, Inês J S; dos Santos, Aldenir F; Gaspar, Jorge F; Martins, Célia; Rueff, José; Diakanamwa, Carlos; Sant'Ana, Antônio E G; de Mendonça, Dina I M D

    2010-05-01

    Four labdanes with a 8alpha,15-epoxy ring (8alpha,15-epoxylabdan-16beta-oic acid; 8alpha,15-epoxy-16-norlabdan-13-one; 8alpha,15-epoxy-16-norlabdane; and 16-acetoxy-8alpha,15-epoxylabdane) and the known compound ambreinolide were isolated from the hexane extract of the aerial parts of the grass Eragrostis viscosa. The structures of all compounds were established based on spectroscopic data and the X-ray analysis of 8alpha,15-epoxy-16-norlabdan-13-one. The hexane extract presented moderate activity against the snail Biomphalaria glabrata. 8alpha,15-Epoxylabdan-16beta-oic acid showed no mutagenic activity for doses up to 1000 microg/plate and no significant clastogenic activity for doses up to 100 microg/ml.

  4. Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide.

    PubMed

    O'Sullivan, Timothy P; Zhang, Hongbin; Mander, Lewis N

    2007-08-21

    In model studies towards the synthesis of harringtonolide, the construction of the tropone moiety via arene cyclopropanation was investigated. The installation of the lactone ring was accomplished by way of a Diels-Alder cycloaddition of various indenones and a-pyones. The incorporation of the key bridge methyl group and subsequent control of its stereochemistry is also outlined.

  5. World Natural Gas Model

    1994-12-01

    RAMSGAS, the Research and Development Analysis Modeling System World Natural Gas Model, was developed to support planning of unconventional gaseoues fuels research and development. The model is a scenario analysis tool that can simulate the penetration of unconventional gas into world markets for oil and gas. Given a set of parameter values, the model estimates the natural gas supply and demand for the world for the period from 1980 to 2030. RAMSGAS is based onmore » a supply/demand framwork and also accounts for the non-renewable nature of gas resources. The model has three fundamental components: a demand module, a wellhead production cost module, and a supply/demand interface module. The demand for gas is a product of total demand for oil and gas in each of 9 demand regions and the gas share. Demand for oil and gas is forecast from the base year of 1980 through 2030 for each demand region, based on energy growth rates and price-induced conservation. For each of 11 conventional and 19 unconventional gas supply regions, wellhead production costs are calculated. To these are added transportation and distribution costs estimates associated with moving gas from the supply region to each of the demand regions and any economic rents. Based on a weighted average of these costs and the world price of oil, fuel shares for gas and oil are computed for each demand region. The gas demand is the gas fuel share multiplied by the total demand for oil plus gas. This demand is then met from the available supply regions in inverse proportion to the cost of gas from each region. The user has almost complete control over the cost estimates for each unconventional gas source in each year and thus can compare contributions from unconventional resources under different cost/price/demand scenarios.« less

  6. Nature, nurture and epigenetics.

    PubMed

    Crews, David; Gillette, Ross; Miller-Crews, Isaac; Gore, Andrea C; Skinner, Michael K

    2014-12-01

    Real life by definition combines heritability (e.g., the legacy of exposures) and experience (e.g. stress during sensitive or 'critical' periods), but how to study or even model this interaction has proven difficult. The hoary concept of evaluating traits according to nature versus nurture continues to persist despite repeated demonstrations that it retards, rather than advances, our understanding of biological processes. Behavioral genetics has proven the obvious, that genes influence behavior and, vice versa, that behavior influences genes. The concept of Genes X Environment (G X E) and its modern variants was viewed as an improvement on nature-nurture but has proven that, except in rare instances, it is not possible to fractionate phenotypes into these constituent elements. The entanglement inherent in terms such as nature-nurture or G X E is a Gordian knot that cannot be dissected or even split. Given that the world today is not what it was less than a century ago, yet the arbitrator (differential survival and reproduction) has stayed constant, de novo principles and practices are needed to better predict what the future holds. Put simply, the transformation that is now occurring within and between individuals as a product of global endocrine disruption is quite independent of what has been regarded as evolution by selection. This new perspective should focus on how epigenetic modifications might revise approaches to understand how the phenotype and, in particular its components, is shaped. In this review we summarize the literature in this developing area, focusing on our research on the fungicide vinclozolin. PMID:25102229

  7. Nature Inspired Surface Coatings

    NASA Astrophysics Data System (ADS)

    Rubner, Michael

    2011-04-01

    Materials Scientists more and more are looking to nature for clues on how to create highly functional surface coatings with exceptional properties. The fog harvesting capabilities of the Namib Desert beetle, the beautiful iridescent colors of the hummingbird, and the super water repellant abilities of the Lotus leaf are but a few examples of the amazing properties developed over many years in the natural world. Nature also makes extensive use of the pH-dependent behavior of weak functional groups such as carboxylic acid and amine functional groups. This presentation will explore synthetic mimics to the nano- and microstructures responsible for these fascinating properties. For example, we have demonstrated a pH-induced porosity transition that can be used to create porous films with pore sizes that are tunable from the nanometer scale to the multiple micron scale. The pores of these films, either nano- or micropores, can be reversibly opened and closed by changes in solution pH. The ability to engineer pH-gated porosity transitions in heterostructured thin films has led to the demonstration of broadband anti-reflection coatings that mimic the anti-reflection properties of the moth eye and pH-tunable Bragg reflectors with a structure and function similar to that found in hummingbird wings and the Longhorn beetle. In addition, the highly textured honeycomb-like surfaces created by the formation of micron-scale pores are ideally suited for the creation of superhydrophobic surfaces that mimic the behavior of the self-cleaning lotus leaf. The development of synthetic "backbacks" on immune system cells that may one day ferry drugs to disease sites will also be discussed.

  8. Nature, nurture and epigenetics.

    PubMed

    Crews, David; Gillette, Ross; Miller-Crews, Isaac; Gore, Andrea C; Skinner, Michael K

    2014-12-01

    Real life by definition combines heritability (e.g., the legacy of exposures) and experience (e.g. stress during sensitive or 'critical' periods), but how to study or even model this interaction has proven difficult. The hoary concept of evaluating traits according to nature versus nurture continues to persist despite repeated demonstrations that it retards, rather than advances, our understanding of biological processes. Behavioral genetics has proven the obvious, that genes influence behavior and, vice versa, that behavior influences genes. The concept of Genes X Environment (G X E) and its modern variants was viewed as an improvement on nature-nurture but has proven that, except in rare instances, it is not possible to fractionate phenotypes into these constituent elements. The entanglement inherent in terms such as nature-nurture or G X E is a Gordian knot that cannot be dissected or even split. Given that the world today is not what it was less than a century ago, yet the arbitrator (differential survival and reproduction) has stayed constant, de novo principles and practices are needed to better predict what the future holds. Put simply, the transformation that is now occurring within and between individuals as a product of global endocrine disruption is quite independent of what has been regarded as evolution by selection. This new perspective should focus on how epigenetic modifications might revise approaches to understand how the phenotype and, in particular its components, is shaped. In this review we summarize the literature in this developing area, focusing on our research on the fungicide vinclozolin.

  9. Vancomycin assembly: nature's way.

    PubMed

    Hubbard, Brian K; Walsh, Christopher T

    2003-02-17

    Antibiotics are precious resources in the fight to combat bacterial infections caused by pathogenic organisms. Vancomycin is one of the antibiotics of last resort in the treatment of life-threatening infections by gram-positive bacteria. The rules by which nature assembles the glycopeptide (vancomycin) and lipoglycopeptide (teicoplanin) antibiotics are becoming elucidated and verified: first amino acids are synthesized, then joined together and cross-linked. This knowledge opens up approaches for reprogramming strategies at the level of altered monomers, swapped assembly lines, and different post-assembly tailoring enzymes.

  10. Turbulent Plumes in Nature

    NASA Astrophysics Data System (ADS)

    Woods, Andrew W.

    2010-01-01

    This review describes a range of natural processes leading to the formation of turbulent buoyant plumes, largely relating to volcanic processes, in which there are localized, intense releases of energy. Phenomena include volcanic eruption columns, bubble plumes in lakes, hydrothermal plumes, and plumes beneath the ice in polar oceans. We assess how the dynamics is affected by heat transfer, particle fallout and recycling, and Earth's rotation, as well as explore some of the mixing of the ambient fluid produced by plumes in a confined geometry.

  11. Natural Killer Cell Memory.

    PubMed

    O'Sullivan, Timothy E; Sun, Joseph C; Lanier, Lewis L

    2015-10-20

    Natural killer (NK) cells have historically been considered short-lived cytolytic cells that can rapidly respond against pathogens and tumors in an antigen-independent manner and then undergo cell death. Recently, however, NK cells have been shown to possess traits of adaptive immunity and can acquire immunological memory in a manner similar to that of T and B cells. In this review, we discuss evidence of NK cell memory and the mechanisms involved in the generation and survival of these innate lymphocytes.

  12. "Naturally occurring asbestos

    NASA Astrophysics Data System (ADS)

    Cagnard, F.; Lahondère, D.; Blein, O.; Lahfid, A.; Wille, G.

    2012-04-01

    The term asbestos refers to six silicate minerals from amphibole and serpentine groups. By definition, it consists in bundles of thin and flexible long fibers, with high-tensile strength, and chemical and heat resistance. In contrast to asbestos found within commercial products and mining, the specific term ''naturally occurring asbestos'' (NOA) refers to asbestiform minerals occurring within rocks or soils that can be released by human activities or weathering processes. The fact that the exposure to asbestos is related to lung pathologies is now widely demonstrated (e.g. asbestosis, mesothelioma and lung cancer). However, if health risks associated with exposure to NOA exist, they are not yet well documented. The crystallization of natural asbestos occurs in specific Mg-rich lithologies associated with peculiar structural and metamorphic conditions. By recognizing and combining such specific geologic criteria, the presence or the absence of asbestos in bedrock terrains can be reasonably predicted and maps of NOA hazard can be drawn. We present here new results of geological mapping and petrological study concerning the evaluation of the NOA hazard in the Alps and Corsica, in France. The three folds approach consists in (1) a determination of lithologies with potential NOA from a bibliographic compilation and extraction of target zones from a geological geodatabase (2) a geological mapping of the target zones followed by a petrological characterization of sampled asbestiform minerals in the laboratory (optical microscopy, TEM, SEM, and Raman spectroscopy technics), and (3) the drawing of the final map of NOA hazard, at regional-scale. Occurrence criteria can be retained as follows: 1. NOA are abundant in the internal zones of the Alps and Corsica, especially within ophiolitic complexes. Natural asbestos are mostly concentrated within ultramafic rocks but can also occur within basic lithologies such as Mg-metagabbros, metabasalts and meta-pillow-lavas, 2. Asbestos

  13. Marine natural products.

    PubMed

    Blunt, John W; Copp, Brent R; Keyzers, Robert A; Munro, Murray H G; Prinsep, Michèle R

    2015-02-01

    This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1163 for 2013), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

  14. Marine natural products.

    PubMed

    Blunt, John W; Copp, Brent R; Keyzers, Robert A; Munro, Murray H G; Prinsep, Michèle R

    2016-03-01

    This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

  15. Natural Analogue Synthesis Report

    SciTech Connect

    A. M. Simmons

    2002-05-01

    The purpose of this report is to present analogue studies and literature reviews designed to provide qualitative and quantitative information to test and provide added confidence in process models abstracted for performance assessment (PA) and model predictions pertinent to PA. This report provides updates to studies presented in the ''Yucca Mountain Site Description'' (CRWMS M and O 2000 [151945], Section 13) and new examples gleaned from the literature, along with results of quantitative studies conducted specifically for the Yucca Mountain Site Characterization Project (YMP). The intent of the natural analogue studies was to collect corroborative evidence from analogues to demonstrate additional understanding of processes expected to occur during postclosure at a potential Yucca Mountain repository. The report focuses on key processes by providing observations and analyses of natural and anthropogenic (human-induced) systems to improve understanding and confidence in the operation of these processes under conditions similar to those that could occur in a nuclear waste repository. The process models include those that represent both engineered and natural barrier processes. A second purpose of this report is to document the various applications of natural analogues to geologic repository programs, focusing primarily on the way analogues have been used by the YMP. This report is limited to providing support for PA in a confirmatory manner and to providing corroborative inputs for process modeling activities. Section 1.7 discusses additional limitations of this report. Key topics for this report are analogues to emplacement drift degradation, waste form degradation, waste package degradation, degradation of other materials proposed for the engineered barrier, seepage into drifts, radionuclide flow and transport in the unsaturated zone (UZ), analogues to coupled thermal-hydrologic-mechanical-chemical processes, saturated zone (SZ) transport, impact of radionuclide

  16. Marine natural products.

    PubMed

    Blunt, John W; Copp, Brent R; Keyzers, Robert A; Munro, Murray H G; Prinsep, Michèle R

    2014-01-17

    This review covers the literature published in 2012 for marine natural products, with 1035 citations (673 for the period January to December 2012) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1241 for 2012), together with the relevant biological activities, source organisms and country of origin. Biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included. PMID:24389707

  17. Marine natural products.

    PubMed

    Blunt, John W; Copp, Brent R; Keyzers, Robert A; Munro, Murray H G; Prinsep, Michèle R

    2015-02-01

    This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1163 for 2013), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included. PMID:25620233

  18. Marine natural products.

    PubMed

    Blunt, John W; Copp, Brent R; Keyzers, Robert A; Munro, Murray H G; Prinsep, Michèle R

    2016-03-01

    This review covers the literature published in 2014 for marine natural products (MNPs), with 1116 citations (753 for the period January to December 2014) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1378 in 456 papers for 2014), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included. PMID:26837534

  19. Xenicane Natural Products: Biological Activity and Total Synthesis.

    PubMed

    Betschart, Leo; Altmann, Karl-Heinz

    2015-01-01

    The xenicanes are a large class of mostly bicyclic marine diterpenoids featuring a cyclononane ring as a common structural denominator. After a brief introduction into the characteristic structural features of xenicanes and some biogenetic considerations, the major focus of this review will be on the various biological activities that have been reported for xenicanes and on efforts towards the total synthesis of these structures. Several xenicanes have been shown to be potent antiproliferative agents in vitro, but activities have also been reported in relation to inflammatory processes. However, so far, data on the possible in vivo activity of xenicanes are lacking. The major challenge in the total synthesis of xenicanes is the construction of the nine-membered ring. Different strategies have been pursued to establish this crucial substructure, including Grob fragmentation, ring-closing olefin metathesis, or Suzuki cross coupling as the enabling transformations. PMID:26429717

  20. Gluino meets flavored naturalness

    NASA Astrophysics Data System (ADS)

    Blanke, Monika; Fuks, Benjamin; Galon, Iftah; Perez, Gilad

    2016-04-01

    We study constraints from LHC run I on squark and gluino masses in the presence of squark flavor violation. Inspired by the concept of `flavored naturalness', we focus on the impact of a non-zero stop-scharm mixing and mass splitting in the right-handed sector. To this end, we recast four searches of the ATLAS and CMS collaborations, dedicated either to third generation squarks, to gluino and squarks of the first two generations, or to charm-squarks. In the absence of extra structure, the mass of the gluino provides an additional source of fine tuning and is therefore important to consider within models of flavored naturalness that allow for relatively light squark states. When combining the searches, the resulting constraints in the plane of the lightest squark and gluino masses are rather stable with respect to the presence of flavor-violation, and do not allow for gluino masses of less than 1.2 TeV and squarks lighter than about 550 GeV. While these constraints are stringent, interesting models with sizable stop-scharm mixing and a relatively light squark state are still viable and could be observed in the near future.

  1. Thermoacoustic natural gas liquefier

    SciTech Connect

    Swift, G.W.

    1995-06-01

    In collaboration with Cryenco Inc. and NIST-Boulder, we intend to develop a natural gas-powered natural-gas liquefier which has absolutely no moving parts and requires no electrical power. It will have high efficiency, remarkable reliability, and low cost. Progress on the liquefier to be constructed at Cryenco continues satisfactorily. The thermoacoustic driver is still ahead of the pulse tube refrigerator, because of NIST`s schedule. We completed the thermoacoustics design in the fall of 1994, with Los Alamos providing physics input and checks of all aspects, and Cryenco providing engineering to ASME code, drafting, etc. Completion of this design represents a significant amount of work, especially in view of the many unexpected problems encountered. Meanwhile, Cryenco and NIST have almost completed the design of the pulse tube refrigerator. At Los Alamos, we have assembled a half-size scale model of the thermoacoustic portion of the 500 gal/day TANGL. This scale model will enable easy experimentation in harmonic suppression techniques, new stack geometries, new heat-exchanger geometries, resonator coiling, and other areas. As of March 1995, the scale model is complete and we are performing routine debugging tests and modifications.

  2. Naturally Occurring Food Toxins

    PubMed Central

    Dolan, Laurie C.; Matulka, Ray A.; Burdock, George A.

    2010-01-01

    Although many foods contain toxins as a naturally-occurring constituent or, are formed as the result of handling or processing, the incidence of adverse reactions to food is relatively low. The low incidence of adverse effects is the result of some pragmatic solutions by the US Food and Drug Administration (FDA) and other regulatory agencies through the creative use of specifications, action levels, tolerances, warning labels and prohibitions. Manufacturers have also played a role by setting limits on certain substances and developing mitigation procedures for process-induced toxins. Regardless of measures taken by regulators and food producers to protect consumers from natural food toxins, consumption of small levels of these materials is unavoidable. Although the risk for toxicity due to consumption of food toxins is fairly low, there is always the possibility of toxicity due to contamination, overconsumption, allergy or an unpredictable idiosyncratic response. The purpose of this review is to provide a toxicological and regulatory overview of some of the toxins present in some commonly consumed foods, and where possible, discuss the steps that have been taken to reduce consumer exposure, many of which are possible because of the unique process of food regulation in the United States. PMID:22069686

  3. Natural gas hydrates

    SciTech Connect

    Sloan, E.D. Jr. )

    1991-12-01

    This paper reports on gas clathrates (commonly called hydrates), which are crystalline compounds that occur when water form a cage-like structure around smaller guest molecules. Gas hydrates of interest to the natural gas hydrocarbon industry are composed of water and eight molecules: methane, ethane, propane, isobutane, normal butane, nitrogen, carbon dioxide, and hydrogen sulfide. Hydrate formation is possible in any place where water exists with such molecules - in natural or artificial environments and at temperatures above and below 32{degrees} F when the pressure is elevated. Hydrates are considered a nuisance because they block transmission lines, plug blowout preventers, jeopardize the foundations of deepwater platforms and pipelines, cause tubing and casing collapse, and foul process heat exchangers, valves, and expanders. Common examples of preventive measures are the regulation of pipeline water content, unusual drilling-mud compositions, and large quantities of methanol injection into pipelines. We encounter conditions that encourage hydrate formation as we explore more unusual environments for gas and oil, including deepwater frontiers and permafrost regions.

  4. Optimizing stop naturalness

    NASA Astrophysics Data System (ADS)

    Wymant, Chris

    2012-12-01

    In supersymmetric models, a large average stop mass MS is well known to both boost the lightest Higgs boson mass mh and also make radiative electroweak symmetry breaking unnaturally tuned. The case of “maximal mixing,” where the stop trilinear mixing term At is set to give At2/MS2=6, allows the stops to be as light as possible for a given mh. Here we make the distinction between minimal MS and optimal naturalness, showing that the latter occurs for less-than-maximal mixing. Lagrange-constrained optimization reveals that the two coincide closely in the Minimal Supersymmetric Standard Model (MSSM)—optimally we have 5naturalness considerations.

  5. Natural medicaments in dentistry

    PubMed Central

    Sinha, Dakshita J.; Sinha, Ashish A.

    2014-01-01

    The major objective in root canal treatment is to disinfect the entire root canal system. Cleaning, shaping, and use of antimicrobial medicaments are effective in reducing the bacterial load to some extent, but some bacteria do remain behind and multiply, causing reinfection. Taking into consideration the ineffectiveness, potential side-effects and safety concerns of synthetic drugs, the herbal alternatives for endodontic usage might prove to be advantageous. Over the past decade, interest in drugs derived from medicinal plants has markedly increased. Phytomedicine has been used in dentistry as anti-inflammatory, antibiotic, analgesic, sedative and also as endodontic irrigant. Herbal preparations can be derived from the root, leaves, seeds, stem, and flowers. The PubMed database search revealed that the reference list for natural medicaments featured 1480 articles and in dentistry 173 articles. A forward search was undertaken on the selected articles and author names. This review focuses on various natural drugs and products as well as their therapeutic applications when used as phytomedicine in dentistry. PMID:25558153

  6. [Natural philosophy in medieval medicine].

    PubMed

    Riha, Ortrun

    2007-01-01

    Medieval medicine is not much interested in natural philosophy. Nevertheless, it is based upon clear methodological and epistemological principles, where the word 'nature' is used in several ways. The natural 'virtues' of things--including magical ones--are most important for therapy. Human health is influenced by stars (planets, zodiac) and seasons, and the physician has to take into account such cosmic effects. The chances of healing depend on the patients' 'nature' in relation to the power of illness. A strong nature makes medicine superfluous, an overwhelming disease cannot be beaten. Thus, medicine is limited to 'neutral' situations when supporting the patient makes his 'nature' win.

  7. Natural gas monthly, April 1999

    SciTech Connect

    1999-05-06

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. There are two feature articles in this issue: Natural gas 1998: Issues and trends, Executive summary; and Special report: Natural gas 1998: A preliminary summary. 6 figs., 28 tabs.

  8. [Natural philosophy in medieval medicine].

    PubMed

    Riha, Ortrun

    2007-01-01

    Medieval medicine is not much interested in natural philosophy. Nevertheless, it is based upon clear methodological and epistemological principles, where the word 'nature' is used in several ways. The natural 'virtues' of things--including magical ones--are most important for therapy. Human health is influenced by stars (planets, zodiac) and seasons, and the physician has to take into account such cosmic effects. The chances of healing depend on the patients' 'nature' in relation to the power of illness. A strong nature makes medicine superfluous, an overwhelming disease cannot be beaten. Thus, medicine is limited to 'neutral' situations when supporting the patient makes his 'nature' win. PMID:18447188

  9. Which naturalism for bioethics? A defense of moderate (pragmatic) naturalism.

    PubMed

    Racine, Eric

    2008-02-01

    There is a growing interest in various forms of naturalism in bioethics, but there is a clear need for further clarification. In an effort to address this situation, I present three epistemological stances: anti-naturalism, strong naturalism, and moderate pragmatic naturalism. I argue that the dominant paradigm within philosophical ethics has been a form of anti-naturalism mainly supported by a strong 'is' and 'ought' distinction. This fundamental epistemological commitment has contributed to the estrangement of academic philosophical ethics from major social problems and explains partially why, in the early 1980s, 'medicine saved the life of ethics'. Rejection of anti-naturalism, however, is often associated with strong forms of naturalism that commit the naturalistic fallacy and threaten to reduce the normative dimensions of ethics to biological imperatives. This move is rightly dismissed as a pitfall since ethics is, in part, a struggle against the course of nature. Rejection of naturalism has drawbacks, however, such as deterring bioethicists from acknowledging the implicit naturalistic epistemological commitments of bioethics. I argue that a moderate pragmatic form of naturalism represents an epistemological position that best embraces the tension of anti-naturalism and strong naturalism: bioethics is neither disconnected from empirical knowledge nor subjugated to it. The discussion is based upon historical writings in philosophy and bioethics.

  10. Which naturalism for bioethics? A defense of moderate (pragmatic) naturalism.

    PubMed

    Racine, Eric

    2008-02-01

    There is a growing interest in various forms of naturalism in bioethics, but there is a clear need for further clarification. In an effort to address this situation, I present three epistemological stances: anti-naturalism, strong naturalism, and moderate pragmatic naturalism. I argue that the dominant paradigm within philosophical ethics has been a form of anti-naturalism mainly supported by a strong 'is' and 'ought' distinction. This fundamental epistemological commitment has contributed to the estrangement of academic philosophical ethics from major social problems and explains partially why, in the early 1980s, 'medicine saved the life of ethics'. Rejection of anti-naturalism, however, is often associated with strong forms of naturalism that commit the naturalistic fallacy and threaten to reduce the normative dimensions of ethics to biological imperatives. This move is rightly dismissed as a pitfall since ethics is, in part, a struggle against the course of nature. Rejection of naturalism has drawbacks, however, such as deterring bioethicists from acknowledging the implicit naturalistic epistemological commitments of bioethics. I argue that a moderate pragmatic form of naturalism represents an epistemological position that best embraces the tension of anti-naturalism and strong naturalism: bioethics is neither disconnected from empirical knowledge nor subjugated to it. The discussion is based upon historical writings in philosophy and bioethics. PMID:18251769

  11. Nature's loss, Immunologists gain?

    PubMed

    Aluvihare

    2000-01-01

    Nature Reviews Molecular Cell Biology Nature Publishing Group (2000). ISSN 1471-0072. Monthly First there was Annual Reviews, then came the monthly Elsevier Trends Journals, both of which try to identify hot topics in their chosen fields. The Current Opinion journals followed several years later, and Current Opinion in Cell Biology is presently one of the highest 'impact factor' review journals, with a distinguished board of editors and advisors and a systematic approach to regular coverage of the major fields of cell biology. Important topics are visited once a year, whether or not something specially exciting happened in the last 12 months. Add to this list Seminars in Cell and Developmental Biology, the FASEB journal and the countless minireviews in 'real' journals, and you begin to wonder how anyone finds any time for doing experiments, or indeed reading the primary literature. So, into this already crowded field arrive three important newcomers: Nature Reviews in Molecular Cell Biology, Genetics, and Neurosciences, of which the first two will probably interest readers of Journal of Cell Science the most. Backed by the name and money of Nature and edited by experienced Nature staff, it is hard to see how these publications can possibly do other than succeed with writers and readers alike. What's inside the first issue? The cover of Nature Reviews in Molecular Cell Biology presents a 3-colour montage of a blue cell nucleus surrounded by splotches of green GPI-anchored GFP overlaid by orange actin stress fibres that seem to come from somewhere else. This image trails a comprehensive review from Kai Simons and Derek Toomre about Lipid Rafts. There are another five major review articles: calcium puffs and sparks, rings around DNA, HIV inhibitors, kinesin and the circadian clock provide a rich and varied mix of topics from authors who know what they're talking about. Surrounding this core is an entertaining mixture of 'highlights' at the front: news and views about

  12. Nature's loss, Immunologists gain?

    PubMed

    Aluvihare

    2000-01-01

    Nature Reviews Molecular Cell Biology Nature Publishing Group (2000). ISSN 1471-0072. Monthly First there was Annual Reviews, then came the monthly Elsevier Trends Journals, both of which try to identify hot topics in their chosen fields. The Current Opinion journals followed several years later, and Current Opinion in Cell Biology is presently one of the highest 'impact factor' review journals, with a distinguished board of editors and advisors and a systematic approach to regular coverage of the major fields of cell biology. Important topics are visited once a year, whether or not something specially exciting happened in the last 12 months. Add to this list Seminars in Cell and Developmental Biology, the FASEB journal and the countless minireviews in 'real' journals, and you begin to wonder how anyone finds any time for doing experiments, or indeed reading the primary literature. So, into this already crowded field arrive three important newcomers: Nature Reviews in Molecular Cell Biology, Genetics, and Neurosciences, of which the first two will probably interest readers of Journal of Cell Science the most. Backed by the name and money of Nature and edited by experienced Nature staff, it is hard to see how these publications can possibly do other than succeed with writers and readers alike. What's inside the first issue? The cover of Nature Reviews in Molecular Cell Biology presents a 3-colour montage of a blue cell nucleus surrounded by splotches of green GPI-anchored GFP overlaid by orange actin stress fibres that seem to come from somewhere else. This image trails a comprehensive review from Kai Simons and Derek Toomre about Lipid Rafts. There are another five major review articles: calcium puffs and sparks, rings around DNA, HIV inhibitors, kinesin and the circadian clock provide a rich and varied mix of topics from authors who know what they're talking about. Surrounding this core is an entertaining mixture of 'highlights' at the front: news and views about

  13. Natural fracturing, by depth

    NASA Astrophysics Data System (ADS)

    Hooker, John; Laubach, Stephen

    2013-04-01

    Natural opening-mode fractures commonly fall upon a spectrum whose end-members are veins, which have wide ranges of sizes and are mostly or thoroughly cemented, and joints, which have little opening displacement and little or no cement. The vein end-member is common in metamorphic rocks, whose high temperature and pressure of formation place them outside typical reservoir settings; conversely, many uncemented joints likely form near the surface and so too have limited relevance to subsurface exploration. Sampling of cores retrieved from tight-gas sandstone reservoirs suggest that it is intermediate fractures, not true joints or veins, that provide natural porosity and permeability. Such fractures have abundant pore space among fracture-bridging cements, which may hold fractures open despite varying states of stress through time. Thus the more sophisticated our understanding of the processes that form veins and joints, i.e., how natural fracturing varies by depth, the better our ability to predict intermediate fractures. Systematic differences between veins and joints, in terms of size-scaling and lateral and stratigraphic spatial arrangement, have been explained in the literature by the mechanical effects of sedimentary layering, which likely exert more control over fracture patterns at shallower depths. Thus stratabound joints commonly have narrow size ranges and regular spacing; non-stratabound veins have a wide range of sizes and spacings. However, new fieldwork and careful literature review suggest that the effects of mechanical layering are only half the story. Although atypical, veins may be highly stratabound and yet spatially clustered; non-stratabound fractures may nonetheless feature narrow size ranges. These anomalous fracture arrangements are better explained by the presence of precipitating cements during fracture opening than by mechanical layering. Cement is thought to be highly important for fracture permeability, but potential effects of

  14. New probe of naturalness.

    PubMed

    Craig, Nathaniel; Englert, Christoph; McCullough, Matthew

    2013-09-20

    Any new scalar fields that perturbatively solve the hierarchy problem by stabilizing the Higgs boson mass also generate new contributions to the Higgs boson field-strength renormalization, irrespective of their gauge representation. These new contributions are physical, and in explicit models their magnitude can be inferred from the requirement of quadratic divergence cancellation; hence, they are directly related to the resolution of the hierarchy problem. Upon canonically normalizing the Higgs field, these new contributions lead to modifications of Higgs couplings that are typically great enough that the hierarchy problem and the concept of electroweak naturalness can be probed thoroughly within a precision Higgs boson program. Specifically, at a lepton collider this can be achieved through precision measurements of the Higgs boson associated production cross section. This would lead to indirect constraints on perturbative solutions to the hierarchy problem in the broadest sense, even if the relevant new fields are gauge singlets.

  15. Natural dispersion revisited.

    PubMed

    Johansen, Øistein; Reed, Mark; Bodsberg, Nils Rune

    2015-04-15

    This paper presents a new semi-empirical model for oil droplet size distributions generated by single breaking wave events. Empirical data was obtained from laboratory experiments with different crude oils at different stages of weathering. The paper starts with a review of the most commonly used model for natural dispersion, which is followed by a presentation of the laboratory study on oil droplet size distributions formed by breaking waves conducted by SINTEF on behalf of the NOAA/UNH Coastal Response Research Center. The next section presents the theoretical and empirical foundation for the new model. The model is based on dimensional analysis and contains two non-dimensional groups; the Weber and Reynolds number. The model was validated with data from a full scale experimental oil spill conducted in the Haltenbanken area offshore Norway in July 1982, as described in the last section of the paper.

  16. Natural Air Purifier

    NASA Technical Reports Server (NTRS)

    1993-01-01

    NASA environmental research has led to a plant-based air filtering system. Dr. B.C. Wolverton, a former NASA engineer who developed a biological filtering system for space life support, served as a consultant to Terra Firma Environmental. The company is marketing the BioFilter, a natural air purifier that combines activated carbon and other filter media with living plants and microorganisms. The filter material traps and holds indoor pollutants; plant roots and microorganisms then convert the pollutants into food for the plant. Most non-flowering house plants will work. After pollutants have been removed, the cleansed air is returned to the room through slits in the planter. Terra Firma is currently developing a filter that will also disinfect the air.

  17. Carotenoid Distribution in Nature.

    PubMed

    Alcaíno, Jennifer; Baeza, Marcelo; Cifuentes, Víctor

    2016-01-01

    Carotenoids are naturally occurring red, orange and yellow pigments that are synthesized by plants and some microorganisms and fulfill many important physiological functions. This chapter describes the distribution of carotenoid in microorganisms, including bacteria, archaea, microalgae, filamentous fungi and yeasts. We will also focus on their functional aspects and applications, such as their nutritional value, their benefits for human and animal health and their potential protection against free radicals. The central metabolic pathway leading to the synthesis of carotenoids is described as the three following principal steps: (i) the synthesis of isopentenyl pyrophosphate and the formation of dimethylallyl pyrophosphate, (ii) the synthesis of geranylgeranyl pyrophosphate and (iii) the synthesis of carotenoids per se, highlighting the differences that have been found in several carotenogenic organisms and providing an evolutionary perspective. Finally, as an example, the synthesis of the xanthophyll astaxanthin is discussed. PMID:27485217

  18. Liquefied Natural Gas Transfer

    NASA Technical Reports Server (NTRS)

    1980-01-01

    Chicago Bridge & Iron Company's tanks and associated piping are parts of system for transferring liquefied natural gas from ship to shore and storing it. LNG is a "cryogenic" fluid meaning that it must be contained and transferred at very low temperatures, about 260 degrees below Fahrenheit. Before the LNG can be pumped from the ship to the storage tanks, the two foot diameter transfer pipes must be cooled in order to avoid difficulties associated with sharp differences of temperature between the supercold fluid and relatively warm pipes. Cooldown is accomplished by sending small steady flow of the cryogenic substance through the pipeline; the rate of flow must be precisely controlled or the transfer line will be subjected to undesirable thermal stress.

  19. Natural flexible dermal armor.

    PubMed

    Yang, Wen; Chen, Irene H; Gludovatz, Bernd; Zimmermann, Elizabeth A; Ritchie, Robert O; Meyers, Marc A

    2013-01-01

    Fish, reptiles, and mammals can possess flexible dermal armor for protection. Here we seek to find the means by which Nature derives its protection by examining the scales from several fish (Atractosteus spatula, Arapaima gigas, Polypterus senegalus, Morone saxatilis, Cyprinius carpio), and osteoderms from armadillos, alligators, and leatherback turtles. Dermal armor has clearly been developed by convergent evolution in these different species. In general, it has a hierarchical structure with collagen fibers joining more rigid units (scales or osteoderms), thereby increasing flexibility without significantly sacrificing strength, in contrast to rigid monolithic mineral composites. These dermal structures are also multifunctional, with hydrodynamic drag (in fish), coloration for camouflage or intraspecies recognition, temperature and fluid regulation being other important functions. The understanding of such flexible dermal armor is important as it may provide a basis for new synthetic, yet bioinspired, armor materials. PMID:23161399

  20. Nature . . . an environmental yardstick

    USGS Publications Warehouse

    Pecora, William T.

    1976-01-01

    To one who has spent his professional career in geologic science, conservation always has had special meaning. In the measurements so necessary to his work the geologist develops an integrity in the use of numbers and in the qualifications attending the validity of numbers. Scientific analysis of geologic events and sequence develops a keen sense of what is coincidental, correlative, and consequential. The geologist applies his science in evaluating hazards to man as natural catastrophes and/or benefits to man such as earth materials that form the resource base of his society. But more than these the geologist has acquired a deep appreciation for the planet as a whole, its inner structure, its landscape, and the living things that abound.

  1. Dengue fever: natural management.

    PubMed

    Qadir, Muhammad Imran; Abbas, Khizar; Tahir, Madeha; Irfan, Muhammad; Raza Bukhari, Syeda Fiza; Ahmed, Bilal; Hanif, Muhammad; Rasul, Akhtar; Ali, Muhammad

    2015-03-01

    Dengue fever is caused by the mosquito-borne dengue virus (DENV) serotypes 1-4, and is the most common arboviral infection of humans in subtropical and tropical regions of the world. Dengue virus infections can present with a spacious range of clinical signs, from a mild feverish illness to a life-threatening shock syndrome. Till now, there is no approved vaccine or drug against this virus. Therefore, there is an urgent need of development of alternative solutions for dengue. Several plant species have been reported with anti-dengue activity. Many herbal/natural drugs, most of which are commonly used as nutritional components, have been used as antiviral, larvicidal, mosquitocidal and mosquito repellents that may be used against dengue. The objective of this review article was to provide current approaches for the treatment and management/prevention of dengue fever by targeting viral proteins involved in replication cycle of the virus and different developmental stages of mosquito.

  2. Natural Radioactivity in Bananas

    SciTech Connect

    Zagatto, V. A. B.; Medina, N. H.; Okuno, E.; Umisedo, N. K.

    2008-08-07

    The content of {sup 40}K natural radionuclide in bananas (Musa sapientum) from the Vale do Ribeira region, Sao Paulo, Brazil, has been measured. We have collected several samples of bananas prata and nanica, its peels, leaves, and also different soils where the banana tree was planted, such as soil with a standard amount of fertilizer, the fertilizer itself and also soil without fertilizer for comparison. We have used the gamma-ray spectroscopy technique with a NaI(T1) crystal inside a 12 cm thick lead shield to detect the gamma-radiation. The results indicate that only part of the available potassium is absorbed by the plant, which is mainly concentrated in the banana peel.

  3. The nature of confidentiality.

    PubMed Central

    Thompson, I E

    1979-01-01

    This paper examines confidentiality and its nature and analyses the guidelines laid down by the Hippocratic Oath as well as the British and World Medical Associations for maintaining such confidentiality between doctor and patient. There are exceptions to practically any code of rules and this is true also for confidentiality. Some of these exceptions make it appear that very little is confidential. The three values implicit in confidentiality would seem to be privacy, confidence and secrecy. Each of these values is discussed and developed in this paper. In conclusion, the question is suggested that maybe in the face of death, doctor and patient need to re-examine the pre-suppositions of privacy, confidence and secrecy on which the confidential relationship is based. PMID:469872

  4. Pest management with natural products

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The 2012 Philadelphia ACS Symposium on Natural Products for Pest Management introduced recent discoveries and applications of natural products from insect, terrestrial plant, microbial, and synthetic sources for the management of insects, weeds, plant pathogenic microbes, and nematodes. The symposiu...

  5. Natural gas monthly, December 1995

    SciTech Connect

    1995-12-01

    This report presents information of interest to organizations associated with the natural gas industry. Data are presented on natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also included.

  6. Natural Gas Exports from Iran

    EIA Publications

    2012-01-01

    This assessment of the natural gas sector in Iran, with a focus on Iran’s natural gas exports, was prepared pursuant to section 505 (a) of the Iran Threat Reduction and Syria Human Rights Act of 2012 (Public Law No: 112-158). As requested, it includes: (1) an assessment of exports of natural gas from Iran; (2) an identification of the countries that purchase the most natural gas from Iran; (3) an assessment of alternative supplies of natural gas available to those countries; (4) an assessment of the impact a reduction in exports of natural gas from Iran would have on global natural gas supplies and the price of natural gas, especially in countries identified under number (2); and (5) such other information as the Administrator considers appropriate.

  7. Natural Gas Monthly, March 1996

    SciTech Connect

    1996-03-25

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  8. Natural gas monthly, October 1998

    SciTech Connect

    1998-10-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. 6 figs., 27 tabs.

  9. Natural gas monthly, June 1998

    SciTech Connect

    1998-06-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. 6 figs., 27 tabs.

  10. Natural gas monthly, July 1998

    SciTech Connect

    1998-07-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. 6 figs., 25 tabs.

  11. Natural gas monthly, April 1995

    SciTech Connect

    1995-04-27

    The Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. 6 figs., 31 tabs.

  12. Natural gas monthly, June 1997

    SciTech Connect

    1997-06-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. 6 figs., 24 tabs.

  13. Natural gas monthly: December 1993

    SciTech Connect

    Not Available

    1993-12-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. Articles are included which are designed to assist readers in using and interpreting natural gas information.

  14. Natural gas monthly, May 1999

    SciTech Connect

    1999-05-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time the NGM features articles designed to assist readers in using and interpreting natural gas information. 6 figs., 27 tabs.

  15. Natural gas monthly, August 1994

    SciTech Connect

    Not Available

    1994-08-24

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  16. Supramolecular complexations of natural products.

    PubMed

    Schneider, Hans-Jörg; Agrawal, Pawan; Yatsimirsky, Anatoly K

    2013-08-21

    Complexations of natural products with synthetic receptors as well as the use of natural products as host compounds are reviewed, with an emphasis on possible practical uses or on biomedical significance. Applications such as separation, sensing, enzyme monitoring, and protection of natural drugs are first outlined. We then discuss examples of complexes with all important classes of natural compounds, such as amino acids, peptides, nucleosides/nucleotides, carbohydrates, catecholamines, flavonoids, terpenoids/steroids, alkaloids, antibiotics and toxins. PMID:23703643

  17. Natural gas monthly, July 1994

    SciTech Connect

    Not Available

    1994-07-20

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  18. Natural gas monthly, November 1993

    SciTech Connect

    Not Available

    1993-11-29

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground state data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  19. Natural gas monthly, September 1995

    SciTech Connect

    1995-09-27

    The (NGM) Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  20. US crude oil, natural gas, and natural gas liquids reserves

    SciTech Connect

    Not Available

    1990-10-05

    This report presents estimates of proved reserves of crude oil, natural gas, and natural gas liquids as of December 31, 1989, and production volumes for the year 1989 for the total United States and for selected states and state sub-divisions. Estimates are presented for the following four categories of natural gas: total gas (wet after lease separation), its two major components (nonassociated and associated-dissolved gas), and total dry gas (wet gas adjusted for the removal of liquids at natural gas processing plants). In addition, two components of natural gas liquids, lease condensate and natural gas plant liquids, have their reserves and production reported separately. Also included is information on indicated additional crude oil reserves and crude oil, natural gas, and lease condensate reserves in nonproducing reservoirs. 28 refs., 9 figs., 15 tabs.

  1. Children's Moral Relationships with Nature.

    ERIC Educational Resources Information Center

    Kahn, Peter H., Jr.; McCoy, Ann

    Two studies of the development of children's moral relationships with nature addressed such questions as: (1) What does it mean to say that we have an obligation not to harm the natural environment? (2) Does the natural environment feel pain? (3) Does it have rights? or (4) Is moral obligation an inappropriate construct by which to understand the…

  2. Advances in the Natural transform

    NASA Astrophysics Data System (ADS)

    Belgacem, F. B. M.; Silambarasan, R.

    2012-11-01

    The literature review of the Natural transform and the existing definitions and connections to the Laplace and Sumudu transforms are discussed in this communication. Along with the complex inverse Natural transform and Heaviside's expansion formula, the relation of Bessel's function to Natural transform (and hence Laplace and Sumudu transforms) are defined.

  3. Natural gas monthly, January 1999

    SciTech Connect

    1999-02-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. 6 figs., 28 tabs.

  4. Natural gas monthly, February 1999

    SciTech Connect

    1999-02-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. 6 figs., 28 tabs.

  5. Natural gas monthly, November 1998

    SciTech Connect

    1998-11-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. 6 figs., 27 tabs.

  6. Percents Are Not Natural Numbers

    ERIC Educational Resources Information Center

    Jacobs, Jennifer A.

    2013-01-01

    Adults are prone to treating percents, one representational format of rational numbers, as novel cases of natural number. This suggests that percent values are not differentiated from natural numbers; a conceptual shift from the natural numbers to the rational numbers has not yet occurred. This is most surprising, considering people are inundated…

  7. Nature and Nationhood: Danish Perspectives

    ERIC Educational Resources Information Center

    Schnack, Karsten

    2009-01-01

    In this paper, I shall discuss Danish perspectives on nature, showing the interdependence of conceptions of "nature" and "nationhood" in the formations of a particular cultural community. Nature, thus construed, is never innocent of culture and cannot therefore simply be "restored" to some pristine, pre-lapsarian state. On the other hand,…

  8. Natural gas monthly, December 1998

    SciTech Connect

    1998-12-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. 6 figs., 28 tabs.

  9. Natural Products for Cancer Prevention

    PubMed Central

    Greenlee, Heather

    2013-01-01

    OBJECTIVES To review the clinical trial literature on the use and effects of natural products for cancer prevention. DATA SOURCES Clinical trials published in PubMed. CONCLUSION There is a growing body of literature on the use of natural products for cancer prevention. To date, few trials have demonstrated conclusive benefit. Current guidelines recommend against the use of natural products for cancer prevention. IMPLICATIONS FOR NURSING PRACTICE Clinicians should ask patients about their use of natural products and motivations for use. If patients are using natural products specifically for cancer prevention, they should be counseled on the current guidelines, as well as their options for other cancer prevention strategies. PMID:22281308

  10. Natural gas monthly, August 1993

    SciTech Connect

    Not Available

    1993-08-25

    The Natural Gas Monthly (NGM) is prepared in the Data Operations Branch of the Reserves and Natural Gas Division, Office of Oil and Gas, Energy Information Administration (EIA), US Department of Energy (DOE). The NGM highhghts activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  11. Natural gas monthly, November 1996

    SciTech Connect

    1996-11-01

    The report highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the Natural Gas Monthly features articles designed to assist readers in using and interpreting natural gas information. The feature article this month is ``US natural gas imports and exports-1995``. 6 figs., 24 tabs.

  12. Natural gas monthly, October 1996

    SciTech Connect

    1996-10-01

    The Natural Gas Monthly (NGM) is prepared in the Data Operations Branch of the Reserves and Natural Gas Division, Office of Oil and Gas, Energy Information Administration (EIA), U.S. Department of Energy (DOE). The NGM highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  13. Natural gas monthly, October 1997

    SciTech Connect

    1997-10-01

    The Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The feature article in this issue is a special report, ``Comparison of Natural Gas Storage Estimates from the EIA and AGA.`` 6 figs., 26 tabs.

  14. Natural gas monthly, June 1996

    SciTech Connect

    1996-06-24

    The natural gas monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The feature article for this month is Natural Gas Industry Restructuring and EIA Data Collection.

  15. Natural gas monthly, April 1997

    SciTech Connect

    1997-04-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are present3ed each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The feature article is entitled ``Natural gas pipeline and system expansions.`` 6 figs., 27 tabs.

  16. Natural gas monthly, August 1995

    SciTech Connect

    1995-08-24

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. This month`s feature article is on US Natural Gas Imports and Exports 1994.

  17. Natural gas monthly, December 1997

    SciTech Connect

    1997-12-01

    The Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The article this month is entitled ``Recent Trends in Natural Gas Spot Prices.`` 6 figs., 27 tabs.

  18. Natural gas monthly, May 1997

    SciTech Connect

    1997-05-01

    The Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The feature article this month is ``Restructuring energy industries: Lessons from natural gas.`` 6 figs., 26 tabs.

  19. Heat distribution by natural convection

    SciTech Connect

    Balcomb, J.D.

    1985-01-01

    Natural convection can provide adequate heat distribution in many situtations that arise in buildings. This is appropriate, for example, in passive solar buildings where some rooms tend to be more strongly solar heated than others or to reduce the number of heating units required in a building. Natural airflow and heat transport through doorways and other internal building apertures is predictable and can be accounted for in the design. The nature of natural convection is described, and a design chart is presented appropriate to a simple, single-doorway situation. Natural convective loops that can occur in buildings are described and a few design guidelines are presented.

  20. Natural gas monthly, July 1997

    SciTech Connect

    1997-07-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The feature article this month is entitled ``Intricate puzzle of oil and gas reserves growth.`` A special report is included on revisions to monthly natural gas data. 6 figs., 24 tabs.

  1. Natural gas monthly, June 1994

    SciTech Connect

    Not Available

    1994-06-01

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The feature article this month is the executive summary from Natural Gas 1994: Issues and Trends. 6 figs., 31 tabs.

  2. Natural Gas Monthly, October 1993

    SciTech Connect

    Not Available

    1993-11-10

    The (NGM) Natural Gas Monthly highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. This month`s feature articles are: US Production of Natural Gas from Tight Reservoirs: and Expanding Rule of Underground Storage.

  3. Natural gas monthly, May 1994

    SciTech Connect

    Not Available

    1994-05-25

    The Natural Gas Monthly (NGM) highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information. The featured articles for this month are: Opportunities with fuel cells, and revisions to monthly natural gas data.

  4. Natural gas monthly, March 1994

    SciTech Connect

    Not Available

    1994-03-22

    The Natural Gas Monthly (NGM) is prepared in the Data Operations Branch of the Reserves and Natural Gas Division, Office of Oil and Gas, Energy Information Administration (EIA), US Department of energy (DOE). The NGM highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  5. Natural gas monthly, September 1993

    SciTech Connect

    Not Available

    1993-09-27

    The Natural Gas Monthly (NGM) is prepared in the Data Operations Branch of the Reserves and Natural Gas Division, Office of Oil and Gas, Energy Information Administration (EIA), US Department of Energy (DOE). The NGM highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, the NGM features articles designed to assist readers in using and interpreting natural gas information.

  6. Natural history and the Encyclopedie.

    PubMed

    Llana, J

    2000-01-01

    The general popularity of natural history in the eighteenth century is mirrored in the frequency and importance of the more than 4,500 articles on natural history in the Encyclopedie. The main contributors to natural history were Daubenton, Diderot, Jaucourt and d'Holbach, but some of the key animating principles derive from Buffon, who wrote nothing specifically for the Encyclopedie. Still, a number of articles reflect his thinking, especially his antipathy toward Linnaeus. There was in principle a natural tie between encyclopedism, with its emphasis on connected knowledge, and the task of natural historians who concentrated on the relationships among living forms. Both the encyclopedists and the natural historians aimed at a sweeping overview of knowledge, and we see that Diderot's discussions of the encyclopedia were apparently informed by his reading of natural history. Most of the articles on natural history drew from traditional sources, but there are differences in emphasis and choice of subject, depending upon the author. Diderot's 300 contributions are often practical, interesting, and depend upon accounts from other parts of the world. Jaucourt, who wrote more articles on natural history than anyone else, followed in his foodsteps. Daubenton's 900 articles reflected a more narrow, professional approach. His contributions concluded for the most part with Volume 8, and Jaucourt carried on almost single-handedly after that. While staking out traditional ground (description, taxonomy) and advancing newer theoretical views linked with Buffon, natural history in the Encyclopedie avoided almost completely the sentimentalism concerning nature that developed after Rousseau. PMID:11624414

  7. Natural gas monthly, April 1998

    SciTech Connect

    1998-04-01

    This issue of the Natural Gas Monthly presents the most recent estimates of natural gas data from the Energy Information Administration (EIA). Estimates extend through April 1998 for many data series. The report highlights activities, events, and analyses of interest to public and private sector organizations associated with the natural gas industry. Volume and price data are presented each month for natural gas production, distribution, consumption, and interstate pipeline activities. Producer-related activities and underground storage data are also reported. From time to time, feature articles are presented designed to assist readers in using and interpreting natural gas information. This issue contains the special report, ``Natural Gas 1997: A Preliminary Summary.`` This report provides information on natural gas supply and disposition for the year 1997, based on monthly data through December from EIA surveys. 6 figs., 28 tabs.

  8. [Carotenoids as natural antioxidants].

    PubMed

    Igielska-Kalwat, Joanna; Gościańska, Joanna; Nowak, Izabela

    2015-04-07

    Human organisms have many defence mechanisms able to neutralise the harmful effects of the reactive species of oxygen. Antioxidants play an important role in reducing the oxidative damage to the human organism. Carotenoids are among the strongest antioxidants. They have 11 coupled double bonds, so they can be classified as polyisoprenoids, show low polarity and can occur in acyclic, monocyclic or bicyclic forms. The carotenoids of the strongest antioxidant properties are lycopene, lutein, astaxanthin and β-carotene. Carotenoids with strong antioxidant properties have found wide application in medical, pharmaceutical and cosmetic industries. These compounds are highly active against both reactive oxygen species and free radicals. Comparing β-carotene, astaxanthin and lycopene with other antioxidants (e.g. vitamin C and E), it can be concluded that these compounds have higher antioxidant activity, e.g. against singlet oxygen. Astaxanthin is a stronger antioxidant compared to β-carotene, vitamin E and vitamin C, respectively 54, 14 and 65 times. Carotenoids have a salutary effect on our body, making it more resistant and strong to fight chronic diseases. The purpose of this article is to review the literature concerning free radicals and their adverse effects on the human body and carotenoids, as strong, natural antioxidants.

  9. Natural gas purchases

    SciTech Connect

    Grenier, E.J. Jr.

    1995-09-01

    In the 1970`s gas and boilers were like oil and water as far as policy makers were concerned, culminating in the Powerplant and Industrial Fuel Use Act (perhaps a more appropriate title would have been the Fuel Non-Use Act or the Gas Non-Use Act). But now, the last two Administrations have made gas the centerpiece of their energy and environmental strategies, including promotion of gas use for boilers and electric generation. The FERC`s Order 636 almost completes the Commission`s restructuring of the gas industry that began with Order 380 (eliminating commodity minimum bills) and progressed sharply with Orders 436 and 500. It is Order 636 that has transformed the interstate pipeline business into a transportation business, with the pipelines virtually out of the merchant business altogether because the Commission is not resting on its laurels after completing implementation of Order 636. Rather, it is exploring new ways to expand the growing competitive market for gas, including the possibility of using market-based rates for interstate pipeline transportation services. Methods for the procurement of natural gas supplies are discussed.

  10. Nature of orchestral noise.

    PubMed

    O'Brien, Ian; Wilson, Wayne; Bradley, Andrew

    2008-08-01

    Professional orchestral musicians are at risk of exposure to excessive noise when at work. This is an industry-wide problem that threatens not only the hearing of orchestral musicians but also the way orchestras operate. The research described in this paper recorded noise levels within a professional orchestra over three years in order to provide greater insight to the orchestral noise environment; to guide future research into orchestral noise management and hearing conservation strategies; and to provide a basis for the future education of musicians and their managers. Every rehearsal, performance, and recording from May 2004 to May 2007 was monitored, with the woodwind, brass, and percussion sections monitored in greatest detail. The study recorded dBALEQ and dBC peak data, which are presented in graphical form with accompanying summarized data tables. The findings indicate that the principal trumpet, first and third horns, and principal trombone are at greatest risk of exposure to excessive sustained noise levels and that the percussion and timpani are at greatest risk of exposure to excessive peak noise levels. However, the findings also strongly support the notion that the true nature of orchestral noise is a great deal more complex than this simple statement would imply.

  11. Optically switchable natural silk

    SciTech Connect

    Krasnov, Igor Müller, Martin; Krekiehn, Nicolai R.; Jung, Ulrich; Magnussen, Olaf M.; Krywka, Christina; Zillohu, Ahnaf U.; Strunskus, Thomas; Elbahri, Mady

    2015-03-02

    An optically active bio-material is created by blending natural silk fibers with photoisomerizable chromophore molecules—azobenzenebromide (AzBr). The material converts the energy of unpolarized light directly into mechanical work with a well-defined direction of action. The feasibility of the idea to produce optically driven microsized actuators on the basis of bio-material (silk) is proven. The switching behavior of the embedded AzBr molecules was studied in terms of UV/Vis spectroscopy. To test the opto-mechanical properties of the modified fibers and the structural changes they undergo upon optically induced switching, single fiber X-ray diffraction with a micron-sized synchrotron radiation beam was combined in situ with optical switching as well as with mechanical testing and monitoring. The crystalline regions of silk are not modified by the presence of the guest molecules, hence occupy only the amorphous part of the fibers. It is shown that chromophore molecules embedded into fibers can be reversibly switched between the trans and cis conformation by illumination with light of defined wavelengths. The host fibers respond to this switching with a variation of the internal stress. The amplitude of the mechanical response is independent of the applied external stress and its characteristic time is shorter than the relaxation time of the usual mechanical response of silk.

  12. Nature's Autonomous Oscillators

    NASA Technical Reports Server (NTRS)

    Mayr, H. G.; Yee, J.-H.; Mayr, M.; Schnetzler, R.

    2012-01-01

    Nonlinearity is required to produce autonomous oscillations without external time dependent source, and an example is the pendulum clock. The escapement mechanism of the clock imparts an impulse for each swing direction, which keeps the pendulum oscillating at the resonance frequency. Among nature's observed autonomous oscillators, examples are the quasi-biennial oscillation and bimonthly oscillation of the Earth atmosphere, and the 22-year solar oscillation. The oscillations have been simulated in numerical models without external time dependent source, and in Section 2 we summarize the results. Specifically, we shall discuss the nonlinearities that are involved in generating the oscillations, and the processes that produce the periodicities. In biology, insects have flight muscles, which function autonomously with wing frequencies that far exceed the animals' neural capacity; Stretch-activation of muscle contraction is the mechanism that produces the high frequency oscillation of insect flight, discussed in Section 3. The same mechanism is also invoked to explain the functioning of the cardiac muscle. In Section 4, we present a tutorial review of the cardio-vascular system, heart anatomy, and muscle cell physiology, leading up to Starling's Law of the Heart, which supports our notion that the human heart is also a nonlinear oscillator. In Section 5, we offer a broad perspective of the tenuous links between the fluid dynamical oscillators and the human heart physiology.

  13. Methylgermanium in natural waters

    NASA Astrophysics Data System (ADS)

    Lewis, Brent L.; Froelich, Philip N.; Andreae, Meinrat O.

    1985-01-01

    Biological methylation of metallic elements1 and the occurrence and cycling of organometals in the environment have been investigated in Japan during the 1950s and 1960s, where the ingestion of fish and shellfish contaminated with methylmercury compounds caused mercury poisoning2,3. Biomethylation ability has been demonstrated in bacteria, fungi and algae for As, Cd, Hg, Pb, Se, Sn, Te and Tl4-7. Naturally-occurring methylated species have been reported in estuaries and seawater for Sb8, As9, Ge10-13 and Sn14, although recent evidence suggests that some reports of methyltin species result from interferences by Ge and volatile sulphur compounds15. With the exception of Sb8, As9,12,16 and Ge11,12, there are no consistent estuarine or oceanic profiles for methylmetal compounds in the literature from which to judge their biogeochemical behaviour. Early investigations17-19 reported that methylgermanium species do not exist in the aquatic environment. Subsequently, we identified monomethylgermanium (MMGe) and dimethylgermanium (DMGe) in estuaries10,12, the Baltic Sea11 and the Bering and Sargasso seas13. We report here recent measurements of methylgermanium compounds in river water, estuaries, seawater and anoxic basins.

  14. Lorentz violation naturalness revisited

    NASA Astrophysics Data System (ADS)

    Belenchia, Alessio; Gambassi, Andrea; Liberati, Stefano

    2016-06-01

    We revisit here the naturalness problem of Lorentz invariance violations on a simple toy model of a scalar field coupled to a fermion field via a Yukawa interaction. We first review some well-known results concerning the low-energy percolation of Lorentz violation from high energies, presenting some details of the analysis not explicitly discussed in the literature and discussing some previously unnoticed subtleties. We then show how a separation between the scale of validity of the effective field theory and that one of Lorentz invariance violations can hinder this low-energy percolation. While such protection mechanism was previously considered in the literature, we provide here a simple illustration of how it works and of its general features. Finally, we consider a case in which dissipation is present, showing that the dissipative behaviour does not percolate generically to lower mass dimension operators albeit dispersion does. Moreover, we show that a scale separation can protect from unsuppressed low-energy percolation also in this case.

  15. Grandmothering and natural selection.

    PubMed

    Kachel, A Friederike; Premo, L S; Hublin, Jean-Jacques

    2011-02-01

    Humans are unique among primates in that women regularly outlive their reproductive period by decades. The grandmother hypothesis proposes that natural selection increased the length of the human post-menopausal period-and, thus, extended longevity-as a result of the inclusive fitness benefits of grandmothering. However, it has yet to be demonstrated that the inclusive fitness benefits associated with grandmothering are large enough to warrant this explanation. Here, we show that the inclusive fitness benefits are too small to affect the evolution of longevity under a wide range of conditions in simulated populations. This is due in large part to the relatively weak selection that applies to women near or beyond the end of their reproductive period. However, we find that grandmothers can facilitate the evolution of a shorter reproductive period when their help decreases the weaning age of their matrilineal grandchildren. Because selection favours a shorter reproductive period in the presence of shorter interbirth intervals, this finding holds true for any form of allocare that helps mothers resume cycling more quickly. We conclude that while grandmothering is unlikely to explain human-like longevity, allocare could have played an important role in shaping other unique aspects of human life history, such as a later age at first birth and a shorter female reproductive period.

  16. World Natural Gas, 1978

    SciTech Connect

    Not Available

    1980-07-01

    World marketed production of natural gas in 1978 totaled 51.749 trillion CF (up from 50.1 TCF in 1977); this 3.3% increase, however, was slightly lower than 1977's 3.7% rise. US production, which fell 0.3% dropped to 38.6% of the world total, while the USSR share (13.137 TCF) accounted for 25.4% (for a growth rate of 7.5%). Of the world gross production of 62.032 TCF, 69.7% came from gas wells; the remainder was associated with oil. Thirty-one percent of the 10.282 TCF difference between gross and marketed gas production was used for oil reservoir repressuring, while the balance (7.094 TCF) was vented and flared. Internationally traded gas movements rose to 11.6% of production. The Netherlands, the USSR, and Canada accounted for 30.6%, 20.1% and 14.7%, respectively, of total 1978 exports. At 0.956 TCF, LNG shipments accounted for 15.9% of world trade, a 35.2% higher share than in 1977; most of this growth was due to increased Indonesia-to-Japan volumes.

  17. Naturalness and supersymmetry

    SciTech Connect

    Agashe, K

    1998-05-01

    In this thesis, the author argues that the supersymmetric Standard Model, while avoiding the fine tuning in electroweak symmetry breaking, requires unnaturalness/fine tuning in some (other) sector of the theory. For example, Baryon and Lepton number violating operators are allowed which lead to proton decay and flavor changing neutral currents. He studies some of the constraints from the latter in this thesis. He has to impose an R-parity for the theory to be both natural and viable. In the absence of flavor symmetries, the supersymmetry breaking masses for the squarks and sleptons lead to too large flavor changing neutral currents. He shows that two of the solutions to this problem, gauge mediation of supersymmetry breaking and making the scalars of the first two generations heavier than a few TeV, reintroduce fine tuning in electroweak symmetry breaking. He also constructs a model of low energy gauge mediation with a non-minimal messenger sector which improves the fine tuning and also generates required Higgs mass terms. He shows that this model can be derived from a Grand Unified Theory despite the non-minimal spectrum.

  18. Higgs inflation and naturalness

    NASA Astrophysics Data System (ADS)

    Lerner, Rose N.; McDonald, John

    2010-04-01

    Inflation based on scalar fields which are non-minimally coupled to gravity has been proposed as a way to unify inflation with weak-scale physics, with the inflaton being identified with the Higgs boson or other weak-scale scalar particle. These models require a large non-minimal coupling ξ ~ 104 to have agreement with the observed density perturbations. However, it has been suggested that such models are unnatural, due to an apparent breakdown of the calculation of Higgs-Higgs scattering via graviton exchange in the Jordan frame. Here we argue that Higgs inflation models are in fact natural and that the breakdown does not imply new physics due to strong-coupling effects or unitarity breakdown, but simply a failure of perturbation theory in the Jordan frame as a calculational method. This can be understood by noting that the model is completely consistent when analysed in the Einstein frame and that scattering rates in the two frames are equal by the Equivalence Theorem for non-linear field redefinitions.

  19. Rx: human nature.

    PubMed

    Ashraf, Nava

    2013-04-01

    Why doesn't a woman who continues to have unwanted pregnancies avail herself of the free contraception at a nearby clinic? What keeps people from using free chlorine tablets to purify their drinking water? Behavioral economics has shown us that we don't always act in our own best interests. This is as true of health decisions as it is of economic ones. An array of biases, limits on cognition, and motivations leads people all over the world to make suboptimal health choices. The good news is that human nature can also be a source of solutions. Through her studies in Zambia exploring the reasons for unwanted pregnancies and the incentives that would motivate hairdressers to sell condoms to their clients, the author has found that designing effective health programs requires more than providing accessible, affordable care; it requires understanding what makes both end users and providers tick. By understanding the cognitive processes underlying our choices and applying the tools of behavioral economics--such as commitment devices, material incentives, defaults, and tools that tap our desire to help others--it's possible to design simple, inexpensive programs that encourage good health decisions and long-term behavior change.

  20. SUSY naturalness without prejudice

    NASA Astrophysics Data System (ADS)

    Ghilencea, D. M.

    2014-05-01

    Unlike the Standard Model (SM), supersymmetric models stabilize the electroweak (EW) scale v at the quantum level and predict that v is a function of the TeV-valued SUSY parameters (γα) of the UV Lagrangian. We show that the (inverse of the) covariance matrix of the model in the basis of these parameters and the usual deviation δχ2 (from χmin2 of a model) automatically encode information about the "traditional" EW fine-tuning measuring this stability, provided that the EW scale v ˜mZ is indeed regarded as a function v =v(γ). It is known that large EW fine-tuning may signal an incomplete theory of soft terms and can be reduced when relations among γα exist (due to GUT symmetries, etc.). The global correlation coefficient of this matrix can help one investigate if such relations are present. An upper bound on the usual EW fine-tuning measure ("in quadrature") emerges from the analysis of the δχ2 and the s-standard deviation confidence interval by using v =v(γ) and the theoretical approximation (loop order) considered for the calculation of the observables. This upper bound avoids subjective criteria for the "acceptable" level of EW fine-tuning for which the model is still "natural."