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1

The characterization and structure-activity evaluation of toxic norditerpenoid alkaloids from two Delphinium species.  

PubMed

A new N-(methylsuccinimido)anthranoyllycoctonine norditerpenoid alkaloid, geyerline, has been isolated and characterized from extracts of the poisonous larkspur Delphinium glaucum. A previously described norditerpenoid alkaloid, grandiflorine, has also been isolated from Delphinium geyeri. Both alkaloids are closely related structurally to the potent neurotoxin methyllycaconitine, established as the primary toxin in many larkspurs poisonous to cattle. Mouse bioassay tests showed grandiflorine to possess toxicity comparable to methyllycaconitine, while its synthetically derived monoacetate, grandiflorine acetate, and geyerline are significantly less toxic. PMID:9748371

Manners, G D; Panter, K E; Pfister, J A; Ralphs, M H; James, L F

1998-09-01

2

Transfer of alkaloids from Delphinium to Castilleja via root parasitism. Norditerpenoid alkaloid analysis by electrospray mass spectrometry  

Microsoft Academic Search

Norditerpenoid alkaloids which are present in the roots of Delphinium occidentale are assimilated into its root parasite, Castilleja sulphurea. The alkaloids are found in all plant parts of the Castilleja (roots, stems, leaves, flowers, seeds) and in the flower nectar. The major root alkaloids (browniine, delcosine, deltaline and dictyocarpine; analyzed by positive ion electrospray mass spectrometry, ESMSH+) were transmitted into

Michelle D. Marko; Frank R. Stermitz

1997-01-01

3

Constitutens of high altitude himalayan herbs part XV: A new norditerpenoid alkaloid from the roots of Aconitum balfourii  

Microsoft Academic Search

A new norditerpenoid alkaloid 9-hydroxysenbushine A has been isolated from the roots of high altitude Himalayan herbAconitumbalfourii by means of vacuum liquid chromatography and centrally accelerated radial thin layer chromatographic techniques and identified by means of MS, H and C?NMR spectral methods.

K. S. Khetwal; Sunita Pande

2004-01-01

4

Analysis of toxic norditerpenoid alkaloids in Delphinium species by electrospray, atmospheric pressure chemical ionization, and sequential tandem mass spectrometry.  

PubMed

A rapid electrospray mass spectrometry method was developed for screening larkspur (Delphinium spp.) plant material for toxic norditerpenoid alkaloids. The method was calibrated using two standard alkaloids, methyllycaconitine (1) and deltaline (2), with a recovery of 92% from spiked samples and relative standard deviations of 6.0% and 8.1% for the two alkaloids, respectively. Thirty-three samples of plains larkspur, Delphinium geyeri, were analyzed. Methyllycaconitine (1) concentration was 0.27% +/- 0.08% during a 1-month period in 1997 establishing the relative risk of poisoning from the plant to be low. The method was also applied to the trace analysis (<1 ppm) of 1 in serum samples from sheep dosed different levels of the alkaloid. Electrospray ionization combined with sequential tandem mass spectrometry and HPLC coupled to atmospheric pressure chemical ionization (APCI) mass spectrometry were used to detect and tentatively identify three new norditerpenoid alkaloids from Delphinium nuttallianum [bearline (6), 14-acetylbearline (7), 16-deacetylgeyerline (8)]. The tentative structure of the new alkaloids was predicted from the tandem mass spectra fragmentation patterns and assigning the substitution pattern for methoxy and acetyl groups at the C-14 and C-16 carbons. PMID:10606571

Gardner, D R; Panter, K E; Pfister, J A; Knight, A P

1999-12-01

5

Total Synthesis, Relay Synthesis, and Structural Confirmation of the C18-Norditerpenoid Alkaloid Neofinaconitine  

PubMed Central

The first total synthesis of the C18-norditerpenoid aconitine alkaloid neofinaconitine and relay syntheses of neofinaconitine and 9-deoxylappaconitine from condelphine are reported. A modular, convergent synthetic approach involves initial Diels–Alder cycloaddition between two unstable components, cyclopropene 10 and cyclopentadiene 11. A second Diels–Alder reaction features the first use of an azepinone dienophile 8, with high diastereofacial selectivity achieved via rational design of the siloxydiene component 36 with a sterically-demanding bromine substituent. Subsequent Mannich-type N-acyliminium and radical cyclizations provide the complete hexacyclic skeleton 33 of the aconitine alkaloids. Key endgame transformations include installation of the C8-hydroxyl group via conjugate addition of water to a putative strained bridghead enone intermediate 45, and one-carbon oxidative truncation of the C4 sidechain to afford racemic neofinaconitine. Complete structural confirmation was provided by a concise relay synthesis of (+)-neofinaconitine and (+)-9-deoxylappaconitine from condelphine, with X-ray crystallographic analysis of the former clarifying the NMR spectral discrepancy between neofinaconitine and delphicrispuline, which were previously assigned identical structures. PMID:24040959

Shi, Yuan; Wilmot, Jeremy T.; Nordstrøm, Lars Ulrik; Tan, Derek S.; Gin, David Y.

2013-01-01

6

Effect of MDL-type alkaloids on tall larkspur toxicosis  

Technology Transfer Automated Retrieval System (TEKTRAN)

Larkspur plants contain numerous norditerpenoid alkaloids which include the 7, 8-methylenedioxylycoctonine (MDL) -type alkaloids and the N-(methylsuccinimido) anthranoyllycoctonine (MSAL) -type alkaloids. The MSAL-type alkaloids are generally much more toxic (typically > 20x). Toxicity of many tal...

7

Toxicokinetics of norditerpenoid alkaloids from low larkspur (Delphinium andersonii) orally administered in cattle  

Technology Transfer Automated Retrieval System (TEKTRAN)

Objective- To better assess low larkspur toxicity and manage treatment of poisoned animals, more knowledge is needed about the serum toxicokinetics of toxic low larkspur alkaloids in cattle. Animals- Five black angus steers. Procedures- Low larkspur (Delphinium andersonii) in the flowering stage...

8

The effect of 7, 8-Methylenedioxylycoctonine -Type Diterpenoid Alkaloids on the Toxicity of Methyllycaconitine in Mice  

Technology Transfer Automated Retrieval System (TEKTRAN)

Larkspur plants contain numerous norditerpenoid alkaloids which include the 7, 8-methylenedioxylycoctonine (MDL-type) alkaloids and the N-(methylsuccinimido) anthranoyllycoctonine (MSAL-type) alkaloids. The MSAL-type alkaloids are generally much more toxic (typically > 20x). The toxicity of many t...

9

The physiological effects and toxicokinetics of tall larkspur (Delphinium barbeyi) alkaloids in cattle  

Technology Transfer Automated Retrieval System (TEKTRAN)

Norditerpenoid alkaloids of larkspur (Delphinium spp.) have a range of pharmacological and physiological properties. For example, the norditerpenoid alkaloid methyllycaconitine (MLA) can act as competitive antagonist at nicotinic cholinergic receptors. In this study, both dose-response and toxicok...

10

Diterpenoid alkaloids of Aconitum vulparia Rchb.  

PubMed

From the roots of Aconitum vulparia Rchb., collected in Prüm (Germany), a new norditerpenoid alkaloid, named alexhumboldtine, has been isolated along with the known norditerpenoid alkaloids lappaconitine, anthranoyllycoctonine, lycoctonine, puberaconitine, ajacine, and septentriodine. The structure of alexhumboldtine was established on the basis of 1H, 13C, DEPT, homonuclear 1H COSY, NOESY, HSQC, and HMBC NMR studies. From the aerial parts of the plant another norditerpenoid alkaloid, aconorine, has been isolated. PMID:22624325

Kurto?lu, Sezin; Sen, Burcu; Meliko?lu, Gülay; Becker, Hans; Zapp, Josef; Kiemer, Alexandra K; Meriçli, Filiz; Meriçli, Ali H

2012-01-01

11

The effect of 7, 8-methylenedioxylycoctonine-type diterpenoid alkaloids on the toxicity of tall larkspur (Delphinium spp.) in cattle.  

PubMed

Delphinium spp. contain numerous norditerpenoid alkaloids which are structurally delineated as 7, 8-methylenedioxylycoctonine (MDL) and N-(methylsuccinimido) anthranoyllycoctonine (MSAL)-type alkaloids. The toxicity of many tall larkspur species has been primarily attributed to their increased concentration of MSAL-type alkaloids, such as methyllycaconitine (MLA), which are typically 20 times more toxic than MDL-type alkaloids. However, the less toxic MDL-type alkaloids are often more abundant than MSAL-type alkaloids in most Delphinium barbeyi and Delphinium occidentale populations. Previous research demonstrated that MDL-type alkaloids increase the acute toxicity of MSAL-type alkaloids. In this study, we examined the role of MDL-type alkaloids on the overall toxicity of tall larkspur plants to cattle while controlling for the exact dose of MSAL-type alkaloids. Cattle were dosed with plant material from 2 different populations of tall larkspur containing either almost exclusively MDL- or MSAL-type alkaloids. These 2 plant populations were combined to create mixtures with ratios of 0.3:1, 1:1, 5:1, and 10:1 MDL- to MSAL-type alkaloids. The dose that elicited similar clinical signs of poisoning in mice and cattle was determined for each mixture on the basis of the MSAL-type alkaloid content. As the ratio of MDL- to MSAL-type alkaloids increased, the amount of MSAL-type alkaloids required to elicit clinical signs decreased. These results indicate that the less toxic MDL-type alkaloids in tall larkspur exacerbate the toxicity of the MSAL-type alkaloids. Consequently, both the amount of MSAL-type alkaloids and the amount of total alkaloids should be fully characterized to determine more accurately the relative toxicity of tall larkspur plant material. PMID:22247113

Welch, K D; Green, B T; Gardner, D R; Cook, D; Pfister, J A; Panter, K E

2012-07-01

12

Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima.  

PubMed

Chemical investigation of the soft coral Sinularia maxima resulted in the isolation of seven norditerpenoids, including two new compounds, 12-hydroxy-scabrolide A (2) and 13-epi-scabrolide C (6). The structures of the isolated compounds were elucidated based on extensive spectroscopic evidence including Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and both one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR, respectively), in comparison with reported data. Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic (BMDCs) with IC(50) values of 5.30 ± 0.21 and 13.12 ± 0.64 ?M, respectively. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC(50) values of 23.52 ± 1.37 and 69.85 ± 4.11 ?M, respectively. PMID:23200246

Thao, Nguyen Phuong; Nam, Nguyen Hoai; Cuong, Nguyen Xuan; Quang, Tran Hong; Tung, Pham The; Dat, Le Duc; Chae, Doobyeong; Kim, Sohyun; Koh, Young-Sang; Kiem, Phan Van; Minh, Chau Van; Kim, Young Ho

2013-01-01

13

Hidden aconite poisoning: identification of yunaconitine and related aconitum alkaloids in urine by liquid chromatography-tandem mass spectrometry.  

PubMed

Poisoning from aconite occurs worldwide as a result of misuse of the potent plant. Laboratory investigation into suspected intoxication cases is challenging because the content of toxic aconitum alkaloids varies depending on the plant source, market processing, dosing protocol, hydrolytic degradation, and metabolic transformation. Using a triple-quadrupole tandem mass spectrometer, a group screening method was developed based on the mass-fragmentographic scheme of common aconitum alkaloids. The precursor-ion scans of m/z 105 and 135 permitted selective profiling of 14-O-benzoyl-norditerpenoids and the 14-O-anisoyl-norditerpenoids, respectively. Gradient reversed-phase liquid chromatography minimized coelution of isobaric compounds. The screening protocol was applied to a clinical investigation of suspected herbal poisoning. In total, 15 urine samples were thus screened positive for aconitum alkaloid over 5 years. The diagnoses of aconite poisoning in 11 patients were firmly established based on the known prescription history and the positive urine finding. In four patients, without aconitum herbs being listed in the herbal prescriptions, contamination of the herbal remedies by aconite was suspected to be the hidden cause of their acute poisoning. Yunaconitne, a highly toxic aconitum alkaloid, was thus identified in human urine for the first time. The group screening method of aconitum alkaloids in urine is an important diagnostic aid for acute poisoning by aconites of an unclear origin. PMID:16959134

Lai, Chi-Kong; Poon, Wing-Tat; Chan, Yan-Wo

2006-09-01

14

Vinca alkaloids.  

PubMed

Vinca alkaloids are a subset of drugs obtained from the Madagascar periwinkle plant. They are naturally extracted from the pink periwinkle plant, Catharanthus roseus G. Don and have a hypoglycemic as well as cytotoxic effects. They have been used to treat diabetes, high blood pressure and have been used as disinfectants. The vinca alkaloids are also important for being cancer fighters. There are four major vinca alkaloids in clinical use: Vinblastine (VBL), vinorelbine (VRL), vincristine (VCR) and vindesine (VDS). VCR, VBL and VRL have been approved for use in the United States. Vinflunine is also a new synthetic vinca alkaloid, which has been approved in Europe for the treatment of second-line transitional cell carcinoma of the urothelium is being developed for other malignancies. Vinca alkaloids are the second-most-used class of cancer drugs and will stay among the original cancer therapies. Different researches and studies for new vinca alkaloid applications will be carried out in this regard. PMID:24404355

Moudi, Maryam; Go, Rusea; Yien, Christina Yong Seok; Nazre, Mohd

2013-11-01

15

Vinca Alkaloids  

PubMed Central

Vinca alkaloids are a subset of drugs obtained from the Madagascar periwinkle plant. They are naturally extracted from the pink periwinkle plant, Catharanthus roseus G. Don and have a hypoglycemic as well as cytotoxic effects. They have been used to treat diabetes, high blood pressure and have been used as disinfectants. The vinca alkaloids are also important for being cancer fighters. There are four major vinca alkaloids in clinical use: Vinblastine (VBL), vinorelbine (VRL), vincristine (VCR) and vindesine (VDS). VCR, VBL and VRL have been approved for use in the United States. Vinflunine is also a new synthetic vinca alkaloid, which has been approved in Europe for the treatment of second-line transitional cell carcinoma of the urothelium is being developed for other malignancies. Vinca alkaloids are the second-most-used class of cancer drugs and will stay among the original cancer therapies. Different researches and studies for new vinca alkaloid applications will be carried out in this regard. PMID:24404355

Moudi, Maryam; Go, Rusea; Yien, Christina Yong Seok; Nazre, Mohd.

2013-01-01

16

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3  

PubMed Central

Summary An unusual C18 norditerpenoid, aspergiloid I (1), was isolated from the culture broth of Aspergillus sp. YXf3, an endophytic fungus derived from Ginkgo biloba. Its structure was unambiguously established by analysis of HRMS–ESI and spectroscopic data, and the absolute configuration was determined by low-temperature (100 K) single crystal X-ray diffraction with Cu K? radiation. This compound is structurally characterized by a new carbon skeleton with an unprecedented 6/5/6 tricyclic ring system bearing an ?,?-unsaturated spirolactone moiety in ring B, and represents a new subclass of norditerpenoid, the skeleton of which is named aspergilane. The hypothetical biosynthetic pathway for 1 was also proposed. The cytotoxic, antimicrobial, anti-oxidant and enzyme inhibitory activities of 1 were evaluated. PMID:25550731

Guo, Zhi Kai; Wang, Rong; Huang, Wei; Li, Xiao Nian; Jiang, Rong

2014-01-01

17

HPLC/MS analysis of toxic norditerpenoid alkaloids: Refinement of toxicity assessment of low larkspurs (Delphinium spp.)  

Technology Transfer Automated Retrieval System (TEKTRAN)

The low larkspurs (Delphinium nuttallianum and D. andersonii) are two toxic plant species that are often fatally ingested by cattle on western U.S. rangelands. To assess the potential toxicity of the plants, methods are needed to identify and quantify the toxic N-methylsuccinimidoanthranoyllycacont...

18

Alkaloids in Marine Algae  

PubMed Central

This paper presents the alkaloids found in green, brown and red marine algae. Algal chemistry has interested many researchers in order to develop new drugs, as algae include compounds with functional groups which are characteristic from this particular source. Among these compounds, alkaloids present special interest because of their pharmacological activities. Alkaloid chemistry has been widely studied in terrestrial plants, but the number of studies in algae is insignificant. In this review, a detailed account of macro algae alkaloids with their structure and pharmacological activities is presented. The alkaloids found in marine algae may be divided into three groups: 1. Phenylethylamine alkaloids, 2. Indole and halogenated indole alkaloids, 3. Other alkaloids. PMID:20390105

Güven, Kas?m Cemal; Percot, Aline; Sezik, Ekrem

2010-01-01

19

Alkaloids from Tabernaemontana psorocarpa.  

PubMed

The isolation of the alkaloids from two different samples of stem bark of Tabernaemontana psorocarpa is described. Both samples contained 16-epi-isositsirikine as the major alkaloid but differed from each other in the number and quantity of the other alkaloids. The following minor alkaloids were identified: 12-methoxy-14,15-dehydro-vincamine, vallesiachotamine, isovallesiachotamine, tetrahydroalstonine, coronaridine and voacangine. PMID:17405098

van Beek, T A; Verpoorte, R; Baerheim Svendsen, A

1983-02-01

20

Alkaloids from Delphinium pentagynum.  

PubMed

Aerial parts of a collection of Delphinium pentagynum Lam. from Niebla, Southern Spain, furnished one diterpene alkaloid, 2-dehydrodeacetylheterophylloidine, two norditerpene alkaloids, 14-demethyl-14-isobutyrylanhweidelphinine and 14-demethyl-14-acetylanhweidelphinine, the known alkaloids 14-deacetylnudicauline, methyllycaconitine, 14-deacetyl-14-isobutyrylnudicauline, 14-acetylbrowniine, browniine, delcosine, lycoctonine, 18-methoxygadesine, neoline, karakoline and the aporphine alkaloid magnoflorine. Structures of the alkaloids were established by MS, 1D and 2-D NMR techniques. PMID:15279983

Díaz, Jesús G; Ruiz, Juan García; Herz, Werner

2004-07-01

21

[Alkaloids of Daphniphyllum angustifolium].  

PubMed

The alkaloids of Daphniphyllum angustifolium were investigated. The whole plant was extracted with 95% EtOH, six alkaloids were isolated and purified with column chromatography over silica gel, RP-18 and Sephadex LH-20. Based on spectral analysis, their structures were identified as daphnilactone B (1), zwitterionic alkaloid (2), yuzurine (3), dehydrodaphnigracilline (4), deoxyyuzurimine (5) and macrodaphniphyllidine (6). All of compounds were obtained from the plant for the first time. PMID:21355269

He, Tao; Mu, Shuzhen; Hao, Xiaojiang; Zhou, Ying; Zhang, Jianxin; Huang, Liejun; Yan, Chen

2010-11-01

22

Amaryllidaceae and Sceletium alkaloids.  

PubMed

Covering: July 2010 to June 2012. Previous review: Nat. Prod. Rep., 2011, 28, 1126-1142. Recent progress on the isolation, identification, biological activity and synthetic studies of structurally diverse alkaloids from plants of the family Amaryllidaceae is summarized in this review. In addition, the structurally related alkaloids isolated from Sceletium species are discussed as well. PMID:23644557

Jin, Zhong

2013-06-01

23

Alkaloids of Glaucium corniculatum  

Microsoft Academic Search

The alkaloids from the epigeal part of the wild blackspot horn poppy have been studied. Twelve alkaloids have been isolated\\u000a of which one — norbracteoline — proved to be new. Its structure has been established. Dehydrocorydine, predicentrine, glaufidine,\\u000a thalicmidine, reticuline, and stylopine ?-methohydroxide have been isolated from this plant for the first time.

I. A. Israilov; S. U. Karimova; O. N. Denisenko; M. S. Yunusov; D. A. Murav'eva; S. Yu. Yunusov

1983-01-01

24

Two Faces of Alkaloids  

NASA Astrophysics Data System (ADS)

Alkaloids can occur in two forms, denoted as ammonium salts and free bases. These forms differ substantially in their properties and in some cases in their structures. The article discusses and compares the salts and free bases of six well-known alkaloids: nicotine, morphine, cocaine, sanguinarine, allocryptopine, and magnoflorine. Relevance for the biological and medical uses of these compounds is emphasized.

Dostál, Jirí

2000-08-01

25

Alkaloids of Datura ceratocaula.  

PubMed

Thirty-six alkaloids were identified in the organs of Datura ceratocaula by GC/MS. Thirty-three of them have not been previously reported for the species. Furthermore, a new tropane ester was tentatively identified as 3-(3'-formyloxytropoyloxy)tropane on basis of its mass spectral fragmentation. Hyoscyamine was the main alkaloid in the plant organs. PMID:12939026

Berkov, Strahil

2003-01-01

26

Genotoxic effect of alkaloids.  

PubMed

Because of the increased use of alkaloids in general medical practice in recent years, it is of interest to determine genotoxic, mutagenic and recombinogenic response to different groups of alkaloids in prokaryotic and eucaryotic organisms. Reserpine, boldine and chelerythrine did not show genotoxicity response in the SOS-Chromotest whereas skimmianine showed genotoxicity in the presence of a metabolic activation mixture. Voacristine isolated from the leaves of Ervatamia coronaria shows in vivo cytostatic and mutagenic effects in Saccharomyces cerevisiae hapioids cells. The Rauwolfia alkaloid (reserpine) was not able to induce reverse mutation and recombinational mitotic events (crossing-over and gene conversion) in yeast diploid strain XS2316. PMID:1842017

Henriques, J A; Moreno, P R; Von Poser, G L; Querol, C C; Henriques, A T

1991-01-01

27

Synthesizing an Alkaloid  

NSDL National Science Digital Library

In this video segment, adapted from NOVA, learn how chemist Percy Julian revolutionized chemistry by synthesizing the alkaloid physostigminefrom scratch—the first total synthesis of a chemical compound.

Foundation, Wgbh E.

2007-02-12

28

Belladonna Alkaloid Combinations and Phenobarbital  

MedlinePLUS

Belladonna alkaloid combinations and phenobarbital are used to relieve cramping pains in conditions such as irritable bowel syndrome and ... Belladonna alkaloid combinations and phenobarbital come as a regular tablet, a slow-acting tablet, capsule, and liquid to take ...

29

Understanding and manipulating alkaloid biosynthesis  

E-print Network

Humans have exploited plant alkaloids as medicines since at least the Neolithic Era. Today, alkaloids such as vinblastine (isolated from Catharanthus roseus) and morphine (isolated from Papaver somniferum) are prescribed ...

Glenn, Weslee S. (Weslee Sinclair)

2013-01-01

30

A novel franchetine type norditerpenoid isolated from the roots of Aconitum carmichaeli Debx. with potential analgesic activity and less toxicity.  

PubMed

Further investigation on the phytochemistry of the plant Aconitum carmichaeli Debx. led to isolate a new franchetine type C(19)-diterpenoid alkaloid, guiwuline 1. Its structure was established on the basis of the spectroscopic data (1D and 2D NMR, HRESIMS, UV, IR). In mouse hot-plate test and acute toxicity assay, compound 1 exhibited potential analgesic activity (ED(50), 15 mg/kg) and showed little toxicity to mice (LD(50), 500 mg/kg). The results indicate that compound 1 may be used as a lead molecule to develop novel analgesic agents. PMID:22658863

Wang, Dao-Ping; Lou, Hua-Yong; Huang, Lan; Hao, Xiao-Jiang; Liang, Guang-Yi; Yang, Zai-Chang; Pan, Wei-Dong

2012-07-01

31

The Effect of High Deltaline Concentration on the Toxicity of Methyllycaconitine in Mice  

Technology Transfer Automated Retrieval System (TEKTRAN)

Larkspurs (Delphinium) are one of the most serious toxic plant problems on foothill and mountain rangelands in the western U.S. Total costs to the livestock industry have been estimated at over $20 million annually. Larkspur plants contain numerous norditerpenoid alkaloids (>18) which occur as one...

32

Spirofornabuxine, a novel type of Buxus alkaloid  

Microsoft Academic Search

From the leaves of Buxus sempervirens has been isolated, in addition to known alkaloids, a new alkaloid, spirofornabuxine (1), and its structure was determined by NMR spectroscopic analysis. This new alkaloid can be considered as the first member of a new group of steroidal derivatives, the spirobuxus alkaloids. Its implication in the biosynthesis of other Buxus alkaloids is discussed. ©

Christophe Fourneau; Reynald Hocquemiller; Didier Guédon; André Cavé

1997-01-01

33

dopamine reuptake inhibitor, glucosidase inhibitor, sodium channel blocker and 5HT1D agonist9. In fact, alkaloid-containing plants have  

E-print Network

. In fact, alkaloid-containing plants have been recognized and exploited since ancient human civilization, from the utilization of Conium maculatum (hemlock) extract containing neurotoxin alkaloids to poison Socrates, to the use of coffee and tea as mild stimulants11. Today, numerous alkaloids are pharmacologi

Cai, Long

34

Quinolizidine alkaloids from Lupinus lanatus  

NASA Astrophysics Data System (ADS)

In this study, one new quinolizidine alkaloid, lanatine A ( 1), together with three other known alkaloids, 13-?- trans-cinnamoyloxylupanine ( 2), 13-?-hydroxylupanine ( 3), and (-)-multiflorine ( 4) were isolated from the aerial parts of Lupinus lanatus (Fabaceae). The structures of alkaloids 1- 4 were elucidated by spectroscopic data analysis. The stereochemistry of 1 was determined by single crystal X-ray analysis. Bayesian statistical analysis of the Bijvoet differences suggests the absolute stereochemistry of 1. In addition, the antimicrobial potential of alkaloids 1- 4 is also reported.

Neto, Alexandre T.; Oliveira, Carolina Q.; Ilha, Vinicius; Pedroso, Marcelo; Burrow, Robert A.; Dalcol, Ionara I.; Morel, Ademir F.

2011-10-01

35

Indole Alkaloids from Trachelospermum jasminoides.  

PubMed

The leaves and stems of T. JASMINOIDES have been found to contain indole alkaloids. Five indole alkaloids, coronaridine, voacangine, apparicine, conoflorine, and 19-epi-voacangarine have been isolated. The (13)C-NMR spectra of apparicine and 19-epi-voacangarine are also reported. PMID:17268963

Fatima, T; Ijaz, S; Crank, G; Wasti, S

1987-02-01

36

Automatic alkaloid removal system.  

PubMed

This alkaloid automated removal machine was developed at Instrumentation Laboratory, Universiti Sultan Zainal Abidin Malaysia that purposely for removing the alkaloid toxicity from Dioscorea hispida (DH) tuber. It is a poisonous plant where scientific study has shown that its tubers contain toxic alkaloid constituents, dioscorine. The tubers can only be consumed after it poisonous is removed. In this experiment, the tubers are needed to blend as powder form before inserting into machine basket. The user is need to push the START button on machine controller for switching the water pump ON by then creating turbulence wave of water in machine tank. The water will stop automatically by triggering the outlet solenoid valve. The powders of tubers are washed for 10 minutes while 1 liter of contaminated water due toxin mixture is flowing out. At this time, the controller will automatically triggered inlet solenoid valve and the new water will flow in machine tank until achieve the desire level that which determined by ultra sonic sensor. This process will repeated for 7 h and the positive result is achieved and shows it significant according to the several parameters of biological character ofpH, temperature, dissolve oxygen, turbidity, conductivity and fish survival rate or time. From that parameter, it also shows the positive result which is near or same with control water and assuming was made that the toxin is fully removed when the pH of DH powder is near with control water. For control water, the pH is about 5.3 while water from this experiment process is 6.0 and before run the machine the pH of contaminated water is about 3.8 which are too acid. This automated machine can save time for removing toxicity from DH compared with a traditional method while less observation of the user. PMID:24783795

Yahaya, Muhammad Rizuwan; Hj Razali, Mohd Hudzari; Abu Bakar, Che Abdullah; Ismail, Wan Ishak Wan; Muda, Wan Musa Wan; Mat, Nashriyah; Zakaria, Abd

2014-01-01

37

Biosynthetic pathways of ergot alkaloids.  

PubMed

Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes. PMID:25513893

Gerhards, Nina; Neubauer, Lisa; Tudzynski, Paul; Li, Shu-Ming

2014-01-01

38

Biosynthetic Pathways of Ergot Alkaloids  

PubMed Central

Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes. PMID:25513893

Gerhards, Nina; Neubauer, Lisa; Tudzynski, Paul; Li, Shu-Ming

2014-01-01

39

Better biosynthesis of ergot alkaloids.  

PubMed

Different culture media containing different effectors for production of ergot-alkaloids were prepared. The culture media were inoculated with equal mycelia of Claviceps purpurea and some were incubated for 22 days and some incubated for 45 days. The medium that contained a mixture of glucose, glycine and tryptophan showed highest yield of the alkaloids and reached the maximum period for production of agroclavine faster. PMID:12918229

Okide, G B; Ajali, U

2003-05-01

40

Diterpenoid alkaloids from Aconitum kirinense.  

PubMed

A new C(18)-diterpenoid alkaloid, kirinenine A (1), was isolated from the root of Aconitum kirinense, along with eight known diterpenoid alkaloids. The structures of all compounds were characterized on the basis of extensive NMR and MS analyses and by comparison with literature values, and the new one was further confirmed by X-ray crystallographic diffraction. All the compounds were isolated from the title plant for the first time. PMID:23323717

Zhang, Sai-Yang; Jiang, Ying; Bi, Yue-Feng; Yan, Wen-Juan; Zhang, Yan-Bing

2013-01-01

41

Berberis alkaloids. XV. Structure of bargustanine  

Microsoft Academic Search

Bargustanine (I), belonging to a new type of isoquinoline alkaloids, has been isolated from the phenolic fraction of the total alkaloids from the roots ofBerberis vulgaris L. Its structure has been established by chemical and spectral methods.

A. Karimov; M. M. Yusupov; R. Shakirov

1993-01-01

42

Total synthesis and study of myrmicarin alkaloids  

E-print Network

I. Enantioselective Total Synthesis of Tricyclic Myrmicarin Alkaloids An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations ...

Ondrus, Alison Evelynn, 1981-

2009-01-01

43

Alkaloids from Senecio aegyptius and S. desfontainei.  

PubMed

Otosenine and senecionine/seneciphyllme were isolated from Senecio aegyptius and S. desfontainei, respectively. Senecionine and seneciphylline easily cocrystallize; m.p. and IR-spectra of mixtures of both alkaloids and their separation by PC are described. IR evidence of individual alkaloids and of the alkaloid-pair are shown. PMID:17402047

Habib, A A

1981-11-01

44

27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2012 CFR

...2012-04-01 2012-04-01 false Brucine alkaloid. 21.99 Section 21.99 Alcohol...for Denaturants § 21.99 Brucine alkaloid. (a) Identification test. Add...nitric acid to about 10 mg of brucine alkaloid. A vivid red color is...

2012-04-01

45

27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2013 CFR

...2013-04-01 2013-04-01 false Brucine alkaloid. 21.99 Section 21.99 Alcohol...for Denaturants § 21.99 Brucine alkaloid. (a) Identification test. Add...nitric acid to about 10 mg of brucine alkaloid. A vivid red color is...

2013-04-01

46

27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2010 CFR

...2010-04-01 2010-04-01 false Brucine alkaloid. 21.99 Section 21.99 Alcohol...for Denaturants § 21.99 Brucine alkaloid. (a) Identification test. Add...nitric acid to about 10 mg of brucine alkaloid. A vivid red color is...

2010-04-01

47

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids  

E-print Network

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids Nicolas Boyer,a Karen C (ETP) alkaloids are a highly complex class of natural products with potent anticancer activity. Herein Epipolythiodiketopiperazine (ETP)1 alkaloids constitute a large (ca. 120 members) and diverse family of biologically active

Hergenrother, Paul J.

48

27 CFR 21.99 - Brucine alkaloid.  

...2014-04-01 2014-04-01 false Brucine alkaloid. 21.99 Section 21.99 Alcohol...for Denaturants § 21.99 Brucine alkaloid. (a) Identification test. Add...nitric acid to about 10 mg of brucine alkaloid. A vivid red color is...

2014-04-01

49

27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2011 CFR

...2011-04-01 2011-04-01 false Brucine alkaloid. 21.99 Section 21.99 Alcohol...for Denaturants § 21.99 Brucine alkaloid. (a) Identification test. Add...nitric acid to about 10 mg of brucine alkaloid. A vivid red color is...

2011-04-01

50

Alkaloids of some Asian Sedum species  

Microsoft Academic Search

The leafy parts of 16 Asian species belonging to the three sections of Sedum were investigated for the presence of alkaloids. Only in seven species of Sedum sect. Sedum were alkaloids found. Sedum bulbiferum, S. japonicum, S. lepidopodium, S. morrisonensis, S. oryzifolium, S. polytrichoides and S. sarmentosum contain 14 pyrrolidine and piperidine alkaloids. Sedum oryzifolium differs significantly from the other

Jeong Hee Kim; Henk'T Hart; Jan F. Stevens

1996-01-01

51

Alkaloidal constituents of Tinospora crispa.  

PubMed

Phytochemical investigations of the stems of Tinospora crispa led to the isolation of one new aporphine alkaloid, N-formylasimilobine 2-O-beta-D-glucopyranoside (1), along with six known alkaloids, N-formylasimilobine 2-O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranoside (2) (tinoscorside A), N-formylanonaine (3), N-formyldehydroanonaine (4), N-formylnomuciferine (5), N-demethyl-N-formyldehydronornuciferine (6), magnoflorine (7), paprazine (8), N-trans-feruloyltyramine (9), and cytidine (10). The structure of new compound 1 was deduced on the basis of spectroscopic data. PMID:21213972

Choudhary, M Iqbal; Ismail, Muhammad; Ali, Zulfiqar; Shaari, Khozirah; Lajis, Nordin H; Atta-ur-Rahman

2010-11-01

52

Biosynthesis of monoterpene indole alkaloids  

E-print Network

Najor Sub joe t: Cher iistry BIOSYNTklESIS OF MONOTERPENE INDOLF ALKALOIDS A Thesis MANU K~A1Q, IN AklLPrJALIA Approved as to style and content by: (Chairman of Oommit tee) (llead of Department) (Flember/ (MGJ(&ber ) (Member ) December I978 xx... ABSTRACT Biosynthesis of Monoterpene Indole Alkaloids (December 1978) Nadhu Ramnarain Ahluwalia, B. A. , Incarnate Word College Chairman of Adv-'sory Committee: Dr. A . Ian Scott. Cathenamine was prepared from the cell-fr e system of Catharanthus ro...

Ahluwalia, Madhu Ramnarain

1978-01-01

53

New alkaloids from Isatis indigotica  

Microsoft Academic Search

From the roots of Isatis indigotica, two new alkaloids named isaindigotidione 1 and isaindigotone 2 were isolated. Their structures were elucidated by spectral and X-ray crystallographic analyses. 1 is the first discovered indolizino[7,6-c]quinoline derivative.

Kung Kai Cheung; Kin Fai Cheng

1997-01-01

54

Late-stage C-H functionalization of complex alkaloids and drug molecules via intermolecular rhodium-carbenoid insertion.  

PubMed

Alkaloids constitute a large family of natural products possessing diverse biological properties. Their unique and complex structures have inspired numerous innovations in synthetic chemistry. In the realm of late-stage C-H functionalization, alkaloids remain a significant challenge due to the presence of the basic amine and a variety of other functional groups. Herein we report the first examples of dirhodium(II)-catalysed intermolecular C-H insertion into complex natural products containing nucleophilic tertiary amines to generate a C-C bond. The application to a diverse range of alkaloids and drug molecules demonstrates remarkable chemoselectivity and predictable regioselectivity. The capacity for late-stage diversification is highlighted in the catalyst-controlled selective functionalizations of the alkaloid brucine. The remarkable selectivity observed, particularly for site-specific C-H insertion at N-methyl functionalities, offers utility in a range of applications where efficient installation of synthetic handles on complex alkaloids is desired. PMID:25581471

He, Jing; Hamann, Lawrence G; Davies, Huw M L; Beckwith, Rohan E J

2015-01-01

55

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

...Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and...Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of...

2014-04-01

56

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2011 CFR

...Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and...Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of...

2011-04-01

57

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2010 CFR

...Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and...Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of...

2010-04-01

58

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2012 CFR

...Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and...Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of...

2012-04-01

59

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2013 CFR

...Dietary supplements containing ephedrine alkaloids. 119.1 Section 119.1 Food and...Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an unreasonable risk of...

2013-04-01

60

Biogenetically inspired synthesis and skeletal diversification of indole alkaloids  

E-print Network

Biogenetically inspired synthesis and skeletal diversification of indole alkaloids Haruki Mizoguchi unprecedented numbers of scaffold variations of terpenoid indole alkaloids. This approach not only allows, stereochemical and functional group properties without structural simplification of naturally occurring alkaloids

Cai, Long

61

Studies on the Alkaloids of Rhazya stricta.  

PubMed

A new strychnos-type alkaloid, bharhingine ( 1), has been isolated from the leaves of RHAZYA STRICTA. Its structure has been assigned on the basis of spectral studies including 2D-NMR measurements. The structure and stereochemistry of another Aspidosperma-type alkaloid, strictanol ( 2) has been investigated by extensive NMR studies including hetero-COSY experiments and NOE difference measurements. Isolation of another strychnos-type alkaloid, vincanicine ( 3), not previously reported from this plant, is also described. PMID:17269012

Ahmad, Y; Fatima, K; Badar, Y

1987-06-01

62

How do slugs cope with toxic alkaloids?  

Microsoft Academic Search

Summary. Arion lusitanicus and other slugs are able to feed on a variety of plants, even those containing toxic secondary metabolites, such as alkaloids. Alkaloids, like sparteine, lupanine, quinidine and atropine are avoided in no-choice feeding experiments only when they are present in concentrations above 1 mg\\/g food pellet. Alkaloids (sparteine, lupanine, cytisine, quinidine, atropine, senecionine, eserine, and harmaline) are toxic

Ramon Aguiar; Michael Wink

2005-01-01

63

Alkaloids from Boophone haemanthoides (Amaryllidaceae).  

PubMed

In this study, the South African Amaryllid Boophone haemanthoides was examined for its phytochemical composition and cytotoxicity. In the process eight alkaloid structures, including the new compound distichaminol, were identified in bulb ethanolic extracts. Of the isolates, lycorine and distichamine exhibited strong activities against human acute lymphoblastic leukemia (CEM), breast adenocarcinoma (MCF7) and cervical adenocarcinoma (HeLa) cells with IC50S ranging from 1.8 to 9.2 microM. PMID:24555277

Nair, Jerald J; Rárová, Lucie; Strnad, Miroslav; Bastidad, Jaume; van Staden, Johannes

2013-12-01

64

Isoquinoline alkaloids from Berberis Vulgaris subsp. Australis  

Microsoft Academic Search

Sixteen isoquinoline alkaloids were isolated from Berberis vulgaris subsp. australis. In addition to quaternary protoberberines and bisbenzylisoquinolines, a new seco-bisbenzylisoquinoline, (-)-tejedine, is reported.

Rafael Suau; Rodrigo Rico; J. Manuel López-Romero; Francisco Nájera; Ana Cuevas

1998-01-01

65

Stereoselective synthesis of (+)-loline alkaloid skeleton.  

PubMed

The loline alkaloids present a compact polycyclic pyrrolizidine skeleton and contain a strained five-membered ethereal bridge, structural features that have proven challenging for synthetic chemists to incorporate since the discovery of this natural product family more than 100 years ago. These alkaloids are produced by mutualistic fungal symbionts (endophytes) living on certain species of pasture grasses and protect the host plant from insect herbivory. The asymmetric total synthesis of loline alkaloids is reported and extends our first-generation (racemic) synthesis of this alkaloid family. Key to the synthesis is a diastereoselective tethered aminohydroxylation of a homoallylic carbamate function and a Petasis Borono-Mannich addition. PMID:25611615

Miller, Kelsey E; Wright, Anthony J; Olesen, Margaret K; Hovey, M Todd; Scheerer, Jonathan R

2015-02-01

66

New alkaloids from Pancratium maritimum.  

PubMed

As a part of ongoing search efforts for the discovery of anticancer lead entities from natural sources, bulbs and flowers of the amaryllidaceous plant Pancratium maritimum have been investigated. Fractionation of the extracts of the fresh flowers and bulbs of P. maritimum led to the isolation of four new alkaloids, namely pancrimatines A (1) and B (2), norismine (3), and pancrimatine C (4), together with the previously reported N-methyl-8,9-methylenedioxy-6-phenanthridone (5), trispheridine (6), and N-methyl-8,9-methylenedioxyphenanthridine (7). The structures of these alkaloids were established on the basis of extensive 1D and 2D NMR and high-resolution mass spectral analyses as well as comparison with the literature. Compounds 2 and 7 showed antiproliferative and antimigratory activity against the highly metastatic human prostate cancer cell line PC-3 cells without cytotoxicity. The phenanthridine alkaloid class was identified as having potential for use to control prostate cancer proliferation and migration. PMID:23970422

Ibrahim, Sabrin R M; Mohamed, Gamal A; Shaala, Lamiaa A; Youssef, Diaa T A; El Sayed, Khalid A

2013-10-01

67

Total synthesis of Class II and Class III Galbulimima Alkaloids  

E-print Network

I. Total Synthesis of All Class III Galbulimima Alkaloids We describe the total synthesis of (+)- and (-)-galbulimima alkaloid 13, (-)-himgaline anad (-)-himbadine. The absolute stereochemistry of natural (-)-galbulimima ...

Tjandra, Meiliana

2010-01-01

68

Simultaneous detection of 22 toxic plant alkaloids (aconitum alkaloids, solanaceous tropane alkaloids, sophora alkaloids, strychnos alkaloids and colchicine) in human urine and herbal samples using liquid chromatography-tandem mass spectrometry.  

PubMed

A liquid chromatography-tandem mass spectrometry method for simultaneous detection of 22 toxic plant alkaloids, including aconitum alkaloids and their hydrolyzed products (aconitine, hypaconitine, mesaconitine, yunaconitine, crassicauline A, benzoylaconine, benzoylmesaconine, benzoylhypaconine, deacetylyunaconitine, deacetylcrassicauline A), solanaceous tropane alkaloids (atropine, anisodamine, scopolamine, anisodine), sophora alkaloids (matrine, sophoridine, oxymatrine, cytisine, N-methylcytisine), strychnos alkaloids (brucine, strychnine) and colchicine, in herbal and urine samples was developed and validated. Following sample preparation by liquid-liquid extraction, chromatographic separation was achieved on Eclipse XDB C8 column. Identification was based on two multiple reaction monitoring transitions and the relative ion intensity. Method selectivity was demonstrated. The limits of detection were 5ng/mL for all analytes, except 50ng/mL for cytisine. The herbal matrix effects ranged from 89% to 118%, whereas the urine matrix effects were between 91% and 109% for all analytes except cytisine (57%) and N-methylcytisine (67%). The urine extraction recovery ranged from 74% to 110% for all analytes, except cytisine (15%) and oxymatrine (30%). With the good extraction efficiency of the other major sophora alkaloids, the relatively low extraction recovery of the minor sophora alkaloids cytisine and oxymatrine did not affect identification of sophora alkaloids as a group. Carry-over was minimal at less than 0.1%. The method was successfully applied in analysis of 170 cases of suspected herbal poisoning, with aconitum alkaloids, sophora alkaloids, solanaceous tropane alkaloids, and strychnos alkaloids being detected in 53, 42, 18, and 6 cases, respectively. PMID:24216273

Ng, Sau Wah; Ching, Chor Kwan; Chan, Albert Yan Wo; Mak, Tony Wing Lai

2013-12-30

69

Tropane alkaloids and toxicity of Convolvulus arvensis  

Microsoft Academic Search

Horses in a few, localized northern Colorado pastures exhibited weight loss and colic. At post mortem, intestinal fibrosis and vascular sclerosis of the small intestine was identified. The pastures where the affected horses grazed were overrun by field bindweed (Convolvulus arvensis). Bindweed from the pasture was found to contain the tropane alkaloids tropine, pseudotropine, and tropinone and the pyrrolidine alkaloids

Fred G. Todd; Frank R. Stermitz; Partricia Schultheis; Anthony P. Knight; Josie Traub-Dargatz

1995-01-01

70

Plant alkaloids of the polymethyleneamine series  

NASA Astrophysics Data System (ADS)

The published data on the structures and biological activities of the plant alkaloids of the biogenic polymethyleneamine series, viz., putrescine (1,4-diaminobutane), spermidine (1,8-diamino-4 -azaoctane), and spermine (1,12-diamino-4,9-diazadodecane), are considered and systematised. The structures and biological activities of some synthetic analogues of these alkaloids are also presented.

Rogoza, Ludmila N.; Salakhutdinov, Nariman F.; Tolstikov, Genrikh A.

2005-04-01

71

A novel steroidal alkaloid from Fritillaria shuchengensis.  

PubMed

A novel steroidal alkaloid, suchengbeisine (1), along with two known steroidal alkaloids, N-oxide of verticinone (2) and zhebeininoside (3), were isolated from the bulbs of Fritillaria shuchengensis S. C. Chen et S. F. Yin. The structures of these compounds were elucidated by intensive spectroscopic methods, including NMR, IR, CD and MS. PMID:22886818

Huang, Shuai; Zhou, Xian-li; Wen, Juan; Wang, Cui-juan; Wang, Hong-yan; Shan, Lian-hai; Weng, Jie

2013-07-01

72

The biogenesis of the Tabernanthe iboga alkaloids  

Microsoft Academic Search

Zusammenfassung Die vorliegende Arbeit schlägt eine Biogenese der Tabernanthe-Alkaloide vor, die von einem ?-Kondensationsprodukt von Tryptophan mit 3,4-Dioxyphenylalanin ausgeht. Der siebengliedrige Ring C dieser Alkaloide entsteht durch Ringöffnung und erneute Ringschliessung eines Oxydationsproduktes. Weitere Stufen umfassen eine Mannich-Kondensation, eine Reduktion und einen Ringschluss zu einer Hydroxycarboxyverbindung, aus der durch einfache Reaktionen Voacangin und Ibogain abgeleitet werden können.

W. I. Taylor

1957-01-01

73

Three new Lycopodium alkaloids from Lycopodium obscurum.  

PubMed

Chemical investigation on the crude alkaloid portion of Lycopodium obscurum led to isolation of three new fawcettimine-type Lycopodium alkaloids, lycobscurines A-C (1-3), together with three known compounds. Their structures were determined by spectroscopic methods including HR-ESI-MS and NMR techniques. All compounds were tested in an assay for acetylcholinesterase inhibitory activity. PMID:23600717

Pan, Ke; Luo, Jian-Guang; Kong, Ling-Yi

2013-01-01

74

Alkaloids from Rauwolfia cubana Stem Bark.  

PubMed

Six indole alkaloids, tetrahydroalstonine, aricine, 16- EPI-affinine, ajmaline, amerovolfine, and amerovolficine have been isolated from the ethanolic extract of the stem bark of RAUWOLFIA CUBANA A. DC. Amerovolfine ( N(alpha)-demethylaccedine) and amerovolficine (16-demethoxy-carbonylpagicerine) are new alkaloids related to 16- EPI-affinine, and their structures have been determined by spectroscopic analysis. PMID:17262416

Martinez, J A; Gomez, C; Santana, T; Velez, H

1989-06-01

75

Tropane alkaloids and toxicity of Convolvulus arvensis.  

PubMed

Horses in a few, localized northern Colorado pastures exhibited weight loss and colic. At post mortem, intestinal fibrosis and vascular sclerosis of the small intestine was identified. The pastures where the affected horses grazed were overrun by field bindweed (Convolvulus arvensis). Bindweed from the pasture was found to contain the tropane alkaloids tropine, pseudotropine, and tropinone and the pyrrolidine alkaloids cuscohygrine and hygrine. Laboratory mice readily ate C. arvensis and exhibited a variety of abnormal clinical signs depending on the amount eaten. Similar alkaloids have been found in other Convolvulus species and cuscohygrine and calystegines (polyhydroxytropanes) have been previously reported from C. arvensis roots. This is the first report of simple tropane alkaloids in C. arvensis, a world wide problem weed. Pseudotropine, the major alkaloid, is known to affect motility and might represent a causative agent for the observed cases of equine intestinal fibrosis. PMID:7495531

Todd, F G; Stermitz, F R; Schultheis, P; Knight, A P; Traub-Dargatz, J

1995-05-01

76

Ecological context influences pollinator deterrence by alkaloids in floral nectar  

E-print Network

LETTER Ecological context influences pollinator deterrence by alkaloids in floral nectar Robert J determined whether the pollinator-deterring effects of a nectar alkaloid found in the perennial vine. sempervirens in nature) to nectar alkaloids in several ecologically relevant scenarios. Although alkaloids

Thomson, James D.

77

Heterologous expression of alkaloid biosynthetic genes — a review  

Microsoft Academic Search

Tetrahydrobenzylisoquinoline alkaloids comprise a diverse class of secondary metabolites with many pharmacologically active members. The biosynthesis at the enzyme level of at least two tetrahydrobenzylisoquinoline alkaloids, the benzophenanthridine alkaloid sanguinarine in the California poppy, Eschscholtzia californica, and the bisbenzylisoquinoline alkaloid berbamunine in barberry, Berberis stolonifera, has been elucidated in detail starting from the aromatic amino acid (aa) l-tyrosine. In an

Toni M. Kutchan

1996-01-01

78

Alkaloids from Portulaca oleracea L  

Microsoft Academic Search

Five alkaloids (oleraceins A, B, C, D and E) were isolated from Portulaca oleracea L., and their structures determined by spectroscopic methods as 5-hydroxy-1-p-coumaric acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-?-d-glucopyranoside, 5-hydroxy-1-ferulic acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-?-d-glucopyranoside, 5-hydroxy-1-(p-coumaric acyl-7?-O-?-d-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-?-d-glucopyranoside, 5-hydroxy-1-(ferulic acyl-7?-O-?-d-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-?-d-glucopyranoside and 8,9-dihydroxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one, respectively.

Lan Xiang; Dongming Xing; Wei Wang; Rufeng Wang; Yi Ding; Lijun Du

2005-01-01

79

Indole Alkaloids from Alocasia macrorrhiza.  

PubMed

Five new indole alkaloids, alocasins A-E (3-7), together with known hyrtiosin B (1) and hyrtiosulawesin (2) were isolated from Alocasia macrorrhiza (L.) SCHOTT; their structures were elucidated on the basis of spectroscopic data. Compounds 1-7 were in vitro tested for cytostatic activity on human throat cancer (Hep-2), human hepatocarcinoma (Hep-G2), and human nasopharyngeal carcinoma epithelial (CNE) cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method; compounds 2, 3, 6 and 7 showed mild antiproliferative activity against Hep-2 and Hep-G2 whereas compounds 2 and 4 showed gentle antiproliferative activity against CNE. PMID:22689406

Zhu, Ling-Hua; Chen, Cheng; Wang, Hui; Ye, Wen-Cai; Zhou, Guang-Xiong

2012-01-01

80

Piperidine alkaloids: Human and food animal teratogens  

Technology Transfer Automated Retrieval System (TEKTRAN)

Piperidine alkaloids are acutely toxic to adult livestock species and produce musculoskeletal deformities in neonatal animals. These teratogenic effects include multiple congenital contracture (MCC) deformities and cleft palate in cattle, pigs, sheep, and goats. Poisonous plants containing teratogen...

81

Total synthesis and study of myrmicarin alkaloids  

E-print Network

The myrmicarins are a family of air- and temperature-sensitive alkaloids that possess unique structural features. Our concise enantioselective synthesis of the tricyclic myrmicarins enabled evaluation of a potentially ...

Ondrus, Alison E.

82

Total synthesis of all (?)-agelastatin alkaloids  

E-print Network

The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family ...

Movassaghi, Mohammad

83

Total synthesis of cyclotryptamine and diketopiperazine alkaloids  

E-print Network

I. Total Synthesis of the (+)-12,12'-Dideoxyverticillin A The fungal metabolite (+)-12,12'-dideoxyverticillin A, a cytotoxic alkaloid isolated from a marine Penicillium sp., belongs to a fascinating family of densely ...

Kim, Justin, Ph. D. Massachusetts Institute of Technology

2013-01-01

84

A new indole alkaloid from Ervatamia yunnanensis  

Microsoft Academic Search

The stems of Ervatamia yunnanensis have afforded a new indole alkaloid, ervataine (1), whose structure was determined by spectroscopic analysis. Five known compounds, ibogaine (2) coronaridine (3), heyneanine (4), voacangine hydroxyindolenine (5) and coronaridine hydroxyindolenine (6), were also isolated.

Yong-Sheng Jin; Jing-Ling Du; Hai-Sheng Chen; Li Jin; Shuang Liang

2010-01-01

85

Alkaloids of the herb Sedum acre L  

Microsoft Academic Search

The influence of the molecular structures of alkaloids present in Sedum acre was investigated in liquid-liquid partition chromatographic systems. The effects of various reactions of the carbonyl group were also determined.

S. Bieganowska; E. Soczewi?ski; M. Bieganowska

1977-01-01

86

New Lycopodium alkaloids from Phlegmariurus squarrosus.  

PubMed

Four new Lycopodium alkaloids (1-4), together with 15 known ones, were isolated from club moss Phlegmariurus squarrosus. Notably, 8?-hydroxylycojapodine A (1) was the first derivative of lycojapodine A (5) which was a novel C16N-type Lycopodium alkaloid with an unprecedented 6/6/6/7 tetracyclic ring system. Their structures were elucidated based on the spectroscopic data, including 1D and 2D NMR techniques. PMID:24841175

Liu, Fei; Dong, Liao-Bin; Gao, Xiu; Wu, Xing-De; He, Juan; Peng, Li-Yan; Cheng, Xiao; Zhao, Qin-Shi

2014-01-01

87

[Studies on the alkaloids of Erythrina plants].  

PubMed

The alkaloidal components of eight Erythrina plants (Leguminosae), E. arborescence Roxb., E. orientalis (L.) Murr, E. crysta-galli Linn, E. crysta-galli (L.) cv. Maruba Deiko H. Murata, E. x bidwilli Lindl, E. poeppigiana (Walp) O. F. Cook, E. glauca Willd, and E. variegata L. were examined. As a result of this study, five new oxo-erythrinan alkaloids, erythrinine (8), 11-hydroxyerysotrine (9), erysotramidine (10), erytharbine (11), crystamidine (12) and a di-benz[d,f]azonine type alkaloid, erybidine (2), were isolated respectively. Two tetrahydroprotoberberine type alkaloids, scoulerine (4) and coreximine (5), were also isolated from E. orientalis (L.) Murr. A new synthetic route to erythrinan alkaloids was developed, via the cis -C/D-ring fused 15-methoxy-16-hydroxyerythrinan-2, 8-dione (49) as a key intermediate, from the enol methyl derivative (48) which was obtained by Birch reduction of the benzyl amide (47). The total synthesis of (+/-)-erysotramidine (10), an oxo-erythrinan alkaloid, including a novel ring cleavage of the aza-tricyclo[3.2.0.0] compound (70) with phenylselenyl chloride is described. PMID:10375996

Ito, K

1999-05-01

88

Lactam ergot alkaloids (ergopeptams) as predominant alkaloids in sclerotia of Claviceps purpurea from Norwegian wild grasses.  

PubMed

Four major alkaloids in the extracts from sclerotia of Claviceps purpurea, picked from wild grasses, have been identified as lactam (non-cyclol) ergot alkaloids. The structural information was obtained from ion trap MS and NMR spectroscopy. The data for one of the lactam ergot alkaloids were coinciding with ergocristam [N-(lysergyl-valyl)-cyclo(phenylalanyl-prolyl)]. The structural information of two further lactam alkaloids was suggestive of either alpha- or beta-ergocryptam [N-(lysergyl-valyl)-cyclo(leucyl-prolyl) or N-(lysergyl-valyl)-cyclo(isoleucyl-prolyl)] and ergoannam [N-(lysergyl-leucyl)-cyclo(leucyl-prolyl) or N-(lysergyl-isoleucyl)-cyclo(isoleucyl-prolyl)]. The constitution of the fourth lactam ergot alkaloid corresponded to N-(lysergyl-isoleucyl)-cyclo(phenylalanyl-prolyl), a new ergopeptam, which has not been described before. Additionally, the cyclol-analogue of the new ergopeptam was detected in the extracts and has been identified on the basis of its product ion spectrum from fragmentation of [M+H](+). The study described in this paper shows that lactam ergot alkaloids may not only be minor products of ergopeptine biosynthesis, as has been suggested hitherto, but may be major biosynthetic endproducts for some ergot strains. This is also the first report demonstrating the production of an ergot alkaloid that contains isoleucine as the second amino acid, i.e. the N-(lysergyl-isoleucyl)-moiety, by parasitic, naturally growing C. purpurea. This unusual type of ergot alkaloid has so far only been found in saprophytic cultures of C. purpurea. PMID:18639312

Uhlig, Silvio; Petersen, Dirk

2008-07-01

89

Determining important parameters related to cyanobacterial alkaloid toxin exposure  

SciTech Connect

Science-based decision making required robust and high-fidelity mechanistic data about the system dynamics and impacts of system changes. Alkaloid cyanotoxins have the characteristics to warrant consideration for their potential threat. Since insufficient information is available to construct a systems model for the alkaloid cyanotoxins, saxitoxins, anatoxins, and anatoxin-a(S), an accurate assessments of these toxins as a potential threat for use for intentional contamination is not possible. Alkaloid cyanotoxin research that contributed to such a model has numerous areas of overlap for natural and intentional health effects issues that generates dual improvements to the state of the science. The use of sensitivity analyses of systems models can identify parameters that, when determined, result in the greatest impact to the overall system and may help to direct the most efficient use of research funding. This type of modeling-assisted experimentation may allow rapid progress for overall system understanding compared to observational or disciplinary research agendas. Assessment and management of risk from intentional contamination can be performed with greater confidence when mechanisms are known and the relationships between different components are validated. This level of understanding allows high-fidelity assessments that do not hamper legitimate possession of these toxins for research purposes, while preventing intentional contamination that would affect public health. It also allows for appropriate response to an intentional contamination event, even if the specific contamination had not been previous considered. Development of science-based decision making tools will only improve our ability to address the new requirements addressing potential threats to our nation.

Love, A H

2005-09-16

90

Enantioselective total Synthesis of the agelastatin and trigonoliimine alkaloids  

E-print Network

I. Total Synthesis of the (-)-Agelastatin Alkaloids The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. ...

Han, Sunkyu, 1982-

2012-01-01

91

Actions of Piperidine Alkaloid Teratogens at Fetal Nicotinic Acetylcholine Receptors.  

Technology Transfer Automated Retrieval System (TEKTRAN)

Teratogenic alkaloids are found in many species of plants including Conium maculatum L., Nicotiana glauca, Nicotiana tabaccum, and multiple Lupinus spp. Fetal musculoskeletal defects produced by alkaloids from these plants include arthrogyropisis, scoliosis, torticollis, kyposis, lordosis, and clef...

92

Rotational Investigation of Tropane Alkaloids  

NASA Astrophysics Data System (ADS)

We report an investigation of the rotational spectrum of several tropane alkaloids using the new Balle-Flygare-type FT-MW spectrometer built at the University of the Basque Country. The initial work focused on the azabicycles of tropinone, scopine and scopoline, vaporized using heating methods. For tropinone the spectrum confirmed the presence of equatorial and axial conformers originated by the inversion of the N-methyl group, with the tropane motif adopting a distorted chair configuration. The determination of substitution and effective structures for the two conformers included the 13C, 15N and 18O isotopomers observed in natural abundance. The structures revealed the flexibility and structural changes associated to the N-methyl inversion, mostly a flattening at the nitrogen atom and a simultaneous rising of the carbonyl group in the axial form. The investigation of scopine gave an intense spectrum, but it was inconsistent with the structural models expected for this molecule. The carrier of the new spectrum was later identified as scopoline, generated in situ by an intramolecular reaction at the moderate temperatures of the nozzle. A single conformation was detected for scopoline, with an ether bridge seriously distorting the tropane motif. E. J. Cocinero, A. Lesarri, P. écija, J.-U. Grabow, J. A. Fernández, F. Castaño, in publication, 2010 E. J. Cocinero, A. Lesarri, P. Écija, J.-U. Grabow, J. A. Fernández, F. Castaño, Phys. Chem. Chem. Phys.,in press, 2010

Cocinero, Emilio J.; Lesarri, Alberto; Ecija, Patricia; Grabow, Jens-Uwe; Fernández, Jose A.; Castano, Fernando

2010-06-01

93

Benzylisoquinoline alkaloid biosynthesis in opium poppy.  

PubMed

Opium poppy (Papaver somniferum) is one of the world's oldest medicinal plants and remains the only commercial source for the narcotic analgesics morphine, codeine and semi-synthetic derivatives such as oxycodone and naltrexone. The plant also produces several other benzylisoquinoline alkaloids with potent pharmacological properties including the vasodilator papaverine, the cough suppressant and potential anticancer drug noscapine and the antimicrobial agent sanguinarine. Opium poppy has served as a model system to investigate the biosynthesis of benzylisoquinoline alkaloids in plants. The application of biochemical and functional genomics has resulted in a recent surge in the discovery of biosynthetic genes involved in the formation of major benzylisoquinoline alkaloids in opium poppy. The availability of extensive biochemical genetic tools and information pertaining to benzylisoquinoline alkaloid metabolism is facilitating the study of a wide range of phenomena including the structural biology of novel catalysts, the genomic organization of biosynthetic genes, the cellular and sub-cellular localization of biosynthetic enzymes and a variety of biotechnological applications. In this review, we highlight recent developments and summarize the frontiers of knowledge regarding the biochemistry, cellular biology and biotechnology of benzylisoquinoline alkaloid biosynthesis in opium poppy. PMID:24671624

Beaudoin, Guillaume A W; Facchini, Peter J

2014-07-01

94

Elisabethamine: a new diterpene alkaloid from Pseudopterogorgia elisabethae  

E-print Network

Elisabethamine: a new diterpene alkaloid from Pseudopterogorgia elisabethae Athar Ata and Russell G from the Florida Keys, have resulted in the isolation of elisabethamine (1), a new diterpene alkaloid Ltd. All rights reserved. Keywords: alkaloids; anti-tumor compounds; anti-in¯ammatory compounds; NMR

Kerr, Russell G.

95

Cenocladamide, a dihydropyridone alkaloid from Piper Craig D. Dodsona,  

E-print Network

Cenocladamide, a dihydropyridone alkaloid from Piper cenocladum Craig D. Dodsona, *, Lee A. Dyera alkaloid, cenocladamide, and a derivative of piplartine, 4'-desmethylpiplartine were isolated along cenocladum; Piperaceae; Leaves; Dihydropyridone alkaloids; N-(3',4',5'-trimethoxycinnamoyl)-D3 -pyridin-2-one

Dyer, Lee

96

Alkaloid production by immobilized mycelia of Claviceps purpurea  

Microsoft Academic Search

Mycelia of Claviceps purpurea CBS 164.59 which produce clavine alkaloids and ergometrine were immobilized in different matrices. These mycelia exhibited a high sensitivity to extreme physical and chemical treatment, and only a moderate immobilization in calcium alginate proved to be the appropriate method to yield high alkaloid amounts. The alkaloid production is correlated to the amount of biomass. The patterns

Bettina Kopp; H. J. Rehm

1983-01-01

97

Inhibition of Human Blood Acetylcholinesterase and Butyrylcholinesterase by Some Alkaloids  

Microsoft Academic Search

A comparative study has been carried out on effects of berberine (diisoquinoline alkaloid) and sanguinarine and chelidonine (benzophenanthridine alkaloids( on erythrocyte acetylcholinesterase and serum butyrylcholinesterase from human blood. The studied alkaloids have been shown to be strong reversible inhibitors of the cholinesterase activity. Acetylcholinesterase is more sensitive to their action, than butyrylcholinesterase. The type of reversible inhibition was determined, and

L. P. Kuznetsova; E. B. Nikol'skaya; E. E. Sochilina; M. D. Faddeeva

2002-01-01

98

Development of an Alkaloid-Pyrone Annulation: Synthesis of Pleiomaltinine**  

PubMed Central

Odd Couple Methodology for the synthesis of alkaloid-pyrones using a novel pyrone annulation of ?–carbolines and indoles with 3-siloxy-4-pyrones is reported. The approach has enabled semisynthesis of the unprecedented alkaloid-pyrone pleiomaltinine from the plant-derived indole-alkaloid pleiocarpamine. PMID:22893619

Ziegler, Robert E.; Tan, Shin-Jowl; Kam, Toh-Seok

2012-01-01

99

Diterpenoid alkaloids and flavonoids from Delphinium trichophorum.  

PubMed

Five hetisane-type C20-diterpenoid alkaloids, trichodelphinines A-E, one delnudine-type C20-diterpenoid alkaloid, trichodelphinine F and three known flavonoids, quercetin, quercetin 3-O-?-D-glucopyranoside, and quercetin 3-O-?-D-glucopyranoside-7-O-?-L-arabinopyranoside, were isolated from whole plants of Delphinium trichophorum Franch. Their structures were elucidated on the basis of extensive spectroscopic analysis, including HSQC, HMBC, (1)H-(1)H COSY, NOESY and X-ray crystallographic analysis, and from chemical evidence. The cytotoxic activities of the diterpenoid alkaloids were evaluated using the MTT method, and the IC50 values of their cytotoxicity against A549 cancer cells ranged from 12.03 to 52.79 ?M. PMID:24256579

Lin, Chao-Zhan; Zhao, Zhong-Xiang; Xie, Si-Min; Mao, Ju-Hua; Zhu, Chen-Chen; Li, Xiao-Hui; Zeren-dawa, Bairi; Suolang-qimei, Kangsa; Zhu, Dun; Xiong, Tian-Qin; Wu, Ai-Zhi

2014-01-01

100

An efficient synthesis of loline alkaloids  

NASA Astrophysics Data System (ADS)

Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges to synthetic chemists. It has been known for more than a century and has been the subject of extensive biological investigations, but only two total syntheses have been achieved to date. Here, we report an asymmetric total synthesis of loline that, with less then ten steps, is remarkably short. Our synthesis incorporates a Sharpless epoxidation, a Grubbs olefin metathesis and an unprecedented transannular aminobromination, which converts an eight-membered cyclic carbamate into a bromopyrrolizidine. The synthesis is marked by a high degree of chemo- and stereoselectivity and gives access to several members of the loline alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex interactions between plants, fungi, insects and bacteria brokered by loline alkaloids.

Cakmak, Mesut; Mayer, Peter; Trauner, Dirk

2011-07-01

101

Alkaloids of Datura ferox from Argentina.  

PubMed

Chromatographic procedures (HPLC, GC-MS) are outlined in this paper for the analysis of alkaloids in poisonous Datura ferox seeds of Argentina, from which previously only quantitative analysis for scopolamine was known. Five additional tropane alkaloids are now identified as 3 alpha-tigloyloxytropane (tigloyltropeine), 3-phenylacetoxy-6 beta,7 beta-epoxytropane (3-phenylacetoxyscopine), aposcopolamine (apohyoscine), 7 beta-hydroxy-6 beta-propenyloxy-3 alpha-tropoyloxytropane, traces of 7 beta-hydroxy-6 beta-isovaleroyloxy-3 alpha-tigloyloxytropane and a pyrrolidine alkaloid, hygrine. Two new structures, 3-phenylacetoxy-6 beta,7 beta-epoxytropane (3-phenylacetoxyscopine) and 7 beta-hydroxy-6 beta-propenyloxy-3 alpha-tropolyoxytropane, are proposed on the basis of their spectra. Hyoscyamine, nicotine and tropane N-oxides were not detected in all samples studied. PMID:8847888

Vitale, A A; Acher, A; Pomilio, A B

1995-12-01

102

Ether bridge formation in loline alkaloid biosynthesis  

PubMed Central

Lolines are potent insecticidal agents produced by endophytic fungi of cool-season grasses. These alkaloids are composed of a pyrrolizidine ring system and an uncommon ether bridge linking carbons 2 and 7. Previous results indicated that 1-aminopyrrolizidine was a pathway intermediate. We used RNA interference to knock down expression of lolO, resulting in the accumulation of a novel alkaloid identified as exo-1-acetamidopyrrolizidine based on high-resolution MS and NMR. Genomes of endophytes differing in alkaloid profiles were sequenced, revealing that those with mutated lolO accumulated exo-1-acetamidopyrrolizidine but no lolines. Heterologous expression of wild-type lolO complemented a lolO mutant, resulting in the production of N-acetylnorloline. These results indicated that the non-heme iron oxygenase, LolO, is required for ether bridge formation, probably through oxidation of exo-1-acetamidopyrrolizidine. PMID:24374065

Pan, Juan; Bhardwaj, Minakshi; Faulkner, Jerome R.; Nagabhyru, Padmaja; Charlton, Nikki D.; Higashi, Richard M.; Miller, Anne-Frances; Young, Carolyn A.; Grossman, Robert B.; Schardl, Christopher L.

2014-01-01

103

Evaporative light scattering detection of pyrrolizidine alkaloids.  

PubMed

A reverse-phase high-performance liquid chromatography method utilizing evaporative light scattering detection (ELSD) has been developed for the simultaneous detection of hepatotoxic pyrrolizidine alkaloids with and without chromophores, namely, riddelliine, riddelliine N-oxide, senecionine, senecionine N-oxide, seneciphylline, retrorsine, integerrimine, lasiocarpine and heliotrine. Pyrrolizidine alkaloids were detected in five plant extracts (Senecio spartioides, S. douglasii var. longilobus, S. jacobaea, S. intergerrimus var. exaltatus and Symphytum officinale). The detection of heliotrine (which does not contain a chromophore) was much improved by ELSD compared with photodiode array detection. PMID:14979525

Schaneberg, Brian T; Molyneux, Russell J; Khan, Ikhlas A

2004-01-01

104

New quinoline alkaloids from Ruta chalepensis.  

PubMed

The roots of Ruta chalepensis, collected from the northern Saudi desert, yielded two new quinoline alkaloids, namely, 2-¿6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexyl¿-hydroquinolin-4-one (1) and 2-¿6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexyl¿-4-methoxy-quinoline (2). Nine previously reported alkaloids, dictamnine, pteleine, skimmianine, rutacridone, isogravacridonechlorine, maculosidine, graveoline, graveolinine, and 4-methoxy-1-methyl-2(1H)-quinolinone, and coumarins, chalepensin, and umbelliferone were also isolated. Structure elucidations were based primarily on 1D and 2D NMR analyses and chemical transformations. Antimicrobial activity of these compounds is discussed. PMID:10924184

El Sayed, K; Al-Said, M S; El-Feraly, F S; Ross, S A

2000-07-01

105

Ephedrine-type alkaloid content of nutritional supplements containingephedra sinica (ma-huang) as determined by high performance liquid chromatography  

Microsoft Academic Search

Nutritional supplements containing Ephedra sinica (ma- huang), a botanical source of ephedrine-type alkaloids, have been linked to numerous episodes of ephedrine (EPH) toxicity. With passage of the 1994 Dietary Supplement Health and Education Act, nutritional supplements are no longer subject to the same FDA preapproval requirements as food additives, prescription, or nonpre- scription medications. As a consequence, EPH content is

B. J. Gurley; P. Wang; S. F. Gardner

1998-01-01

106

Alkaloid production by callous tissue cultures of Cereus peruvianus (Cactaceae).  

PubMed

The morphologically undifferentiated cells of nonregenerant callous tissue of Cereus peruvianus cultured in the original medium and in medium supplemented with tyrosine were used as an alkaloid source. Comparison of alkaloid production by C. peruvianus plants and by callous tissues indicated that alkaloid levels were almost twice as high in callous tissues as in shoots of C. peruvianus plants. The ratio of alkaloid concentration between mature plant and morphologically undifferentiated cells of callous tissue was 1:1.7. A relationship between culture medium containing tyrosine and alkaloid production was also observed in the callous tissues of C. peruvianus. Since increased alkaloid production may be induced by additional factors such as tyrosine, increasing levels of tyrosine or other conditions of the culture medium may be considered factors for inducing higher alkaloid production by C. peruvianus callous tissues. PMID:12603103

de Oliveira, Arildo José Braz; Machado, Maria Fátima Pires da Silva

2003-02-01

107

Metabolism of alkaloids in coffee plants  

Microsoft Academic Search

Coffee beans contain two types of alkaloids, caffeine and trigonelline, as major components. This review describes the distribu- tion and metabolism of these compounds. Caffeine is synthesised from xanthosine derived from purine nucleotides. The major biosynthetic route is xanthosine ? 7-methylxanthosine ? 7-methylxanthine ? theobromine ? caffeine. Degradation activ- ity of caffeine in coffee plants is very low, but catabolism

Hiroshi Ashihara

2006-01-01

108

Anticancer indole alkaloids of Rhazya stricta.  

PubMed

The leaves and roots of Rhazya stricta (Apocynaceae) yielded four indole alkaloids. Three of these isolated, vallesiachotamine (1), sewarine (3) and tetrahydrosecamine (4), displayed cytotoxic activity; polyneuridine (2) was not reported previously from this species. Tetrahydrosecaminediol (5), its acetate 6, and didemethoxycarbonyl-tetrahydrosecamine (7) were prepared from tetrahydrosecamine (4) by chemical reactions. The diol 5 was highly cytotoxic. PMID:7334384

Mukhopadhyay, S; Handy, G A; Funayama, S; Cordell, G A

1981-01-01

109

Four new Amaryllidaceae alkaloids from Zephyranthes candida.  

PubMed

Four new Amaryllidaceae alkaloids (1-4) possessing a homolycorine-type or a crinine-type skeleton have been isolated from the aerial part of Zephyranthes candida, and their structures were elucidated on the basis of spectroscopic data. The stereochemistry was elucidated by combination of NOESY correlations and CD analyses. PMID:24526460

Shitara, Nanase; Hirasawa, Yusuke; Hasumi, Shunsuke; Sasaki, Tadahiro; Matsumoto, Misaki; Wong, Chin Piow; Kaneda, Toshio; Asakawa, Yoshinori; Morita, Hiroshi

2014-07-01

110

A new indole alkaloid from Ervatamia yunnanensis.  

PubMed

The stems of Ervatamia yunnanensis have afforded a new indole alkaloid, ervataine (1), whose structure was determined by spectroscopic analysis. Five known compounds, ibogaine (2) coronaridine (3), heyneanine (4), voacangine hydroxyindolenine (5) and coronaridine hydroxyindolenine (6), were also isolated. PMID:19647051

Jin, Yong-Sheng; Du, Jing-Ling; Chen, Hai-Sheng; Jin, Li; Liang, Shuang

2010-01-01

111

Amides and an alkaloid from Portulaca oleracea.  

PubMed

A total of 16 phenolic compounds, including one new and five known N-cinnamoyl phenylethylamides, one new pyrrole alkaloid named portulacaldehyde, five phenylpropanoid acids and amides, and derivatives of benzaldehyde and benzoic acid, were isolated and identified from a polar fraction of an extract of Portulaca oleracea. Their structures were determined through spectroscopic analyses. PMID:22978226

Kokubun, Tetsuo; Kite, Geoffrey C; Veitch, Nigel C; Simmonds, Monique S J

2012-08-01

112

Characterisation of oxidation products of Rauwolfia alkaloids.  

PubMed

The oxidation products of three Rauwolfia alkaloids having yohimbane skeleton, namely, reserpine, rescinnamine and ajmalicine have been characterised by chromatographic and spectroscopic techniques. The Rf values of the oxidation products (3, 4-dehydro derivatives) in several solvent systems and the spectral data on UV, IR, NMR and fluorescence characteristics have been determined to confirm the structure of these compounds. PMID:16431380

Azeem, S Wasif; Khan, M Ataullah; Ahmad, Iqbal

2005-01-01

113

Fluorescence lifetimes of some Rauwolfia alkaloids  

NASA Astrophysics Data System (ADS)

The natural fluorescence lifetimes of the following Rauwolfia alkaloids, Reserpine, Rescinnamine, Corynanthine, Yohimbine, --- Ajmalicine, Serpentine and Ajmaline, have been calculated from a modified form of the Strickler-Berg equation. The actual lifetimes were derived from the quantum yields and the calculated natural lifetimes.

Hidalgo, J.; Arjona, D. Gonzalez; Roldan, E.; Sanchez, M.

1986-03-01

114

Probing chemical space with alkaloid-inspired libraries.  

PubMed

Screening of small-molecule libraries is an important aspect of probe and drug discovery science. Numerous authors have suggested that bioactive natural products are attractive starting points for such libraries because of their structural complexity and sp(3)-rich character. Here, we describe the construction of a screening library based on representative members of four families of biologically active alkaloids (Stemonaceae, the structurally related cyclindricine and lepadiformine families, lupin and Amaryllidaceae). In each case, scaffolds were based on structures of the naturally occurring compounds or a close derivative. Scaffold preparation was pursued following the development of appropriate enabling chemical methods. Diversification provided 686 new compounds suitable for screening. The libraries thus prepared had structural characteristics, including sp(3) content, comparable to a basis set of representative natural products and were highly rule-of-five compliant. PMID:24451589

McLeod, Michael C; Singh, Gurpreet; Plampin, James N; Rane, Digamber; Wang, Jenna L; Day, Victor W; Aubé, Jeffrey

2014-02-01

115

Probing chemical space with alkaloid-inspired libraries  

NASA Astrophysics Data System (ADS)

Screening of small-molecule libraries is an important aspect of probe and drug discovery science. Numerous authors have suggested that bioactive natural products are attractive starting points for such libraries because of their structural complexity and sp3-rich character. Here, we describe the construction of a screening library based on representative members of four families of biologically active alkaloids (Stemonaceae, the structurally related cyclindricine and lepadiformine families, lupin and Amaryllidaceae). In each case, scaffolds were based on structures of the naturally occurring compounds or a close derivative. Scaffold preparation was pursued following the development of appropriate enabling chemical methods. Diversification provided 686 new compounds suitable for screening. The libraries thus prepared had structural characteristics, including sp3 content, comparable to a basis set of representative natural products and were highly rule-of-five compliant.

McLeod, Michael C.; Singh, Gurpreet; Plampin, James N.; Rane, Digamber; Wang, Jenna L.; Day, Victor W.; Aubé, Jeffrey

2014-02-01

116

Probing Chemical Space with Alkaloid-Inspired Libraries  

PubMed Central

Screening of small molecule libraries is an important aspect of probe and drug discovery science. Numerous authors have suggested that bioactive natural products are attractive starting points for such libraries, due to their structural complexity and sp3-rich character. Here, we describe the construction of a screening library based on representative members of four families of biologically active alkaloids (Stemonaceae, the structurally related cyclindricine and lepadiformine families, lupin, and Amaryllidaceae). In each case, scaffolds were based on structures of the naturally occurring compounds or a close derivative. Scaffold preparation was pursued following the development of appropriate enabling chemical methods. Diversification provided 686 new compounds suitable for screening. The libraries thus prepared had structural characteristics, including sp3 content, comparable to a basis set of representative natural products and were highly rule-of-five compliant. PMID:24451589

McLeod, Michael C.; Singh, Gurpreet; Plampin, James N.; Rane, Digamber; Wang, Jenna L.; Day, Victor W.; Aubé, Jeffrey

2014-01-01

117

Synthesis and evaluation of Strychnos alkaloids as MDR reversal agents for cancer cell eradication  

E-print Network

Synthesis and evaluation of Strychnos alkaloids as MDR reversal agents for cancer cell eradication: Total synthesis Strychnos alkaloids P-glycoprotein ABCB1 Multidrug resistance Resensitization Docking. We have developed an effective synthetic route to prepare various Strychnos alkaloids

118

Enantioselective Synthesis of Tetrahydroprotoberberines and Bisbenzylisoquinoline Alkaloids from a Deprotonated -Aminonitrile  

E-print Network

Enantioselective Synthesis of Tetrahydroprotoberberines and Bisbenzylisoquinoline Alkaloids from for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine and (-)-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O

Lawson, Catherine L.

119

Pyrrolizidine alkaloid profiles of some Senecio species from Egypt.  

PubMed

Alkaloid profiles of two Egyptian Senecio species (Senecio aegyptius var. discoideus and S. desfontainei) in addition to a cultivated species (S. cineraria) were studied using capillary GLC and GLC-mass spectrometry with respect to pyrrolizidine alkaloids (PAs). Four alkaloids were identified in S. aegyptius var. discoideus, 8 in S. desfontainei and 13 in S. cineraria. Some of these alkaloids have not been reported from these plants. The alkaloidal pattern of different plant organs (flowers, leaves, stem, root) were also investigated. Senecionine has been found to be a one of the major alkaloid in all studied species, it was isolated and its structure was elucidated by 1H- and 13C-NMR. PMID:12132679

El-Shazly, Assem

2002-01-01

120

Natural alkaloids: basic aspects, biological roles, and future perspectives.  

PubMed

Natural products have gained popularity worldwide for promoting healthcare, as well as disease prevention. Alkaloids are important chemical compounds that serve as a rich reservoir for drug discovery. Several alkaloids isolated from natural herbs exhibit antiproliferation, antibacterial, antiviral, insecticidal, and antimetastatic effects on various types of cancers both in vitro and in vivo. This paper focuses on the naturally-derived alkaloids such as berberine, matrine, piperine, fritillarine, and rhynchophylline, etc., and summarizes the action mechanisms of these compounds. Based on the information in the literature that is summarized in this paper, the use of alkaloids as drugs is very promising, but more research and clinical trials are necessary before final recommendations on specific alkaloids can be made. Following this, it is hoped that as a result of this review, there will be a greater awareness of the excellent promise that natural alkaloids show for use in the therapy of diseases. PMID:24969519

Qiu, Shi; Sun, Hui; Zhang, Ai-Hua; Xu, Hong-Ying; Yan, Guang-Li; Han, Ying; Wang, Xi-Jun

2014-06-01

121

Alkaloids Isolated from Natural Herbs as the Anticancer Agents  

PubMed Central

Alkaloids are important chemical compounds that serve as a rich reservoir for drug discovery. Several alkaloids isolated from natural herbs exhibit antiproliferation and antimetastasis effects on various types of cancers both in vitro and in vivo. Alkaloids, such as camptothecin and vinblastine, have already been successfully developed into anticancer drugs. This paper focuses on the naturally derived alkaloids with prospective anticancer properties, such as berberine, evodiamine, matrine, piperine, sanguinarine, and tetrandrine, and summarizes the mechanisms of action of these compounds. Based on the information in the literature that is summarized in this paper, the use of alkaloids as anticancer agents is very promising, but more research and clinical trials are necessary before final recommendations on specific alkaloids can be made. PMID:22988474

Lu, Jin-Jian; Bao, Jiao-Lin; Chen, Xiu-Ping; Huang, Min; Wang, Yi-Tao

2012-01-01

122

Quinolizidine alkaloid biosynthesis: recent advances and future prospects  

PubMed Central

Lys-derived alkaloids, including piperidine, quinolizidine, indolizidine, and lycopodium alkaloids, are widely distributed throughout the plant kingdom. Several of these alkaloids have beneficial properties for humans and have been used in medicine. However, the molecular mechanisms underlying the biosynthesis of these alkaloids are not well understood. In the present article, we discuss recent advances in our understanding of Lys-derived alkaloids, especially the biochemistry, molecular biology, and biotechnology of quinolizidine alkaloid (QA) biosynthesis. We have also highlighted Lys decarboxylase (LDC), the enzyme that catalyzes the first committed step of QA biosynthesis and answers a longstanding question about the molecular entity of LDC activity in plants. Further prospects using current advanced technologies, such as next-generation sequencing, in medicinal plants have also been discussed. PMID:23112802

Bunsupa, Somnuk; Yamazaki, Mami; Saito, Kazuki

2012-01-01

123

Chirality and numbering of substituted tropane alkaloids.  

PubMed

The strict application of IUPAC rules for the numbering of tropane alkaloids is not always applied by authors and there is hence a lot of confusion in the literature. In most cases, the notation of 3, 6/7-disubstituted derivatives has been chosen arbitrarily, based on NMR and MS data, without taking into account the absolute configuration of these two carbons. This paper discusses the problem and the relevance of CD and NMR to determine molecular configurations. We report on the use of (1)H-NMR anisochrony (??) induced by the Mosher's chiral auxiliary reagents (R)-(-)- and (S)-(+)-?-methoxy-?-trifluoromethyl-phenylacetyl chlorides (MTPA-Cl), to determine the absolute configuration of (3R,6R)-3?-hydroxy-6?-senecioyloxytropane, a disubstituted tropane alkaloid isolated from the aerial parts of Schizanthus grahamii (Solanaceae). These analytical tools should help future works in correctly assigning the configuration of additional 3, 6/7 disubstituted tropane derivatives. PMID:21869748

Humam, Munir; Shoul, Tarik; Jeannerat, Damien; Muñoz, Orlando; Christen, Philippe

2011-01-01

124

Total synthesis of all (–)-Agelastatin alkaloids  

PubMed Central

The pyrrole-imidazole family of marine alkaloids, derived from linear clathrodin-like precursors, constitutes a diverse array of structurally complex natural products. The bioactive agelastatins are members of this family that possess a tetracyclic molecular framework incorporating C4–C8 and C7–N12 bond connectivities. We provide a hypothesis for the formation of the unique agelastatin architecture that maximally exploits the intrinsic chemistry of plausible biosynthetic precursors. We report the concise enantioselective total syntheses of all known agelastatin alkaloids including the first total syntheses of agelastatins C, D, E, and F. Our gram-scale chemical synthesis of agelastatin A was inspired by our hypothesis for the biogenesis of the cyclopentane C-ring and required the development of new transformations including an imidazolone-forming annulation reaction and a carbohydroxylative trapping of imidazolones. PMID:21218186

Siegel, Dustin S.; Han, Sunkyu

2010-01-01

125

Bioactive steroidal alkaloids from Buxus macowanii Oliv.  

PubMed

Chemical investigation of the crude methanolic extract of Buxus macowanii resulted in the isolation of five new steroidal alkaloids, 31-hydroxybuxatrienone (1), macowanioxazine (2), 16?-hydroxymacowanitriene (3), macowanitriene (4), macowamine (5), along with five known steroidal bases, Nb-demethylpapillotrienine (6), moenjodaramine (7), irehine (8), buxbodine B (9) and buxmicrophylline C (10). Structures of compounds 1-10 were elucidated with the aid of spectroscopic methods including 1D and 2D NMR techniques and mass spectrometry. Compounds 1, 3, and 4 belong to a rare class of Buxus alkaloids having ?(1,2) 9(10?19) abeo triene system. All isolates were evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity and found to exhibit moderate to weak anti-AChE activity with IC50 values in the range of 10.8-98?M. Compounds 1 and 6 were also moderately active in BACE1 inhibitory assay. PMID:25528196

Lam, Cheuk W; Wakeman, Andrew; James, Abin; Ata, Athar; Gengan, Robert M; Ross, Samir A

2015-03-01

126

Total synthesis of the Daphniphyllum alkaloid daphenylline  

NASA Astrophysics Data System (ADS)

The Daphniphyllum alkaloids are a large class of natural products isolated from a genus of evergreen plants widely used in Chinese herbal medicine. They display a remarkable range of biological activities, including anticancer, antioxidant, and vasorelaxation properties as well as elevation of nerve growth factor. Daphenylline is a structurally unique member among the predominately aliphatic Daphniphyllum alkaloids, and contains a tetrasubstituted arene moiety mounted on a sterically compact hexacyclic scaffold. Herein, we describe the first total synthesis of daphenylline. A gold-catalysed 6-exo-dig cyclization reaction and a subsequent intramolecular Michael addition reaction, inspired by Dixon's seminal work, were exploited to construct the bridged 6,6,5-tricyclic motif of the natural product at an early stage, and the aromatic moiety was forged through a photoinduced olefin isomerization/6?-electrocyclization cascade followed by an oxidative aromatization process.

Lu, Zhaoyong; Li, Yong; Deng, Jun; Li, Ang

2013-08-01

127

New prenylated carbazole alkaloids from Zanthoxylum armatum.  

PubMed

A phytochemical investigation on the ethyl acetate soluble fraction of Zanthoxylum armatum led in the isolation of two new prenylated alkaloids 2,6,7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carbaldehyde (1) and methyl-2,6,7-trimethoxy-8-(3-methyl-2-butenyl)carbazole-3-carboxylate (2), along with three known lignans cisamin (3), methyl pirpirtol (4), and fargesin (5) and one known alkaloid dictamine (6). Their structures were established on the basis of spectroscopic and crystallographic analysis and by comparison of the data with those in the literature. All the isolated compounds were screened for the DPPH free radical scavenging activity. Compounds 1, 2, and 6 showed profound activity while compounds 3-5 showed moderate activity. PMID:25355272

Samad, Abdul; Badshah, Syed; Khan, Dilfaraz; Ali, Farman; Amanullah, Malik; Hanrahan, Jane

2014-12-01

128

Manzamine alkaloids as antileishmanial agents: A review.  

PubMed

Leishmaniasis is considered as one of the most Neglected Tropical Diseases (NTDs) in the world, caused by protozoan parasites of the genus Leishmania. Leishmaniasis control profoundly depends upon chemotherapy which includes pentavalent antimonials, paromomycin, pentamidine, amphotericin B and miltefosine. Miltefosine is the only oral drug used for the treatment of Visceral Leishmaniasis with high cure rate but decrease in susceptibility is observed in countries like India where it is extensively used. Hence, there is an urgent need to develop novel antileishmanial agents with good potency and better therapeutic profile. Manzamines are unique group of ?-carboline alkaloids isolated from marine sponges and exhibited potent antileishmanial activity. In the present study, we described antileishmanial activity, cytotoxicity and structure activity relationship of natural manzamine alkaloids. PMID:25023608

Ashok, Penta; Lathiya, Hiren; Murugesan, Sankaranarayanan

2014-07-01

129

Fungal endophyte-infected grasses: Alkaloid accumulation and aphid response  

Microsoft Academic Search

The occurrence of the alkaloidsN-formyl andN-acetyl loline, peramine, lolitrem B, and ergovaline and the response of aphids to plants containing these compounds were determined in species and cultivars ofFestuca,Lolium, and other grass genera infected with fungal endophytes (Acremonium spp., andEpichloe typhina). Twenty-nine of 34 host-fungus associations produced one or more of the alkaloids, most frequently peramine or ergovaline. Three alkaloids

M. R. Siegel; G. C. M. Latch; L. P. Bush; F. F. Fannin; D. D. Rowan; B. A. Tapper; C. W. Bacon; M. C. Johnson

1990-01-01

130

Analgesic activity of diterpene alkaloids from Aconitum baikalensis.  

PubMed

We compared analgesic activities of individual alkaloids extracted from Baikal aconite (Aconitum baikalensis): napelline, hypaconitine, songorine, mesaconitine, 12-epinapelline N-oxide. The detected analgesic activity was comparable to that of sodium metamizole. The mechanisms of analgesia were different in diterpene alkaloids of different structure. The antinociceptive effect of atisine alkaloids (12-epinapelline N-oxide, songorine) was naloxonedependent and realized via opioid receptor modulation. PMID:25110090

Nesterova, Yu V; Povet'yeva, T N; Suslov, N I; Zyuz'kov, G N; Pushkarskii, S V; Aksinenko, S G; Schultz, E E; Kravtsova, S S; Krapivin, A V

2014-08-01

131

Pyrrolizidine alkaloids of Cynoglossum officinale and Cynoglossum amabile (family boraginaceae)  

Microsoft Academic Search

Heliosupine, heliosupine N-oxide, 3?-acetylheliosupine, and viridiflorine were isolated and identified on the base of MS, 1H and 13C NMR from Cynoglossum officinale. Altogether 14 pyrrolizidine alkaloids were separated and identified by GLC and GLC-MS in the alkaloid extracts from different parts of Cynoglossum officinale. From Cynoglossum amabile five pyrrolizidine alkaloids were recorded: supinine, amabiline, rinderine, echinatine, and 3?-O-acetylechinatine.

A. El-Shazly; T. Sarg; A. Ateya; E. Abdel Aziz; L. Witte; M. Wink

1996-01-01

132

Alkaloid production by callous tissue cultures of Cereus peruvianus (Cactaceae)  

Microsoft Academic Search

The morphologically undifferentiated cells of nonregenerant callous tissue of Cereus peruvianus cultured in the original medium and in medium supplemented with tyrosine were used as an alkaloid source. Comparison of alkaloid\\u000a production by C. peruvianus plants and by callous tissues indicated that alkaloid levels were almost twice as high in callous tissues as in shoots of\\u000a C. peruvianus plants. The

Arildo José Braz de Oliveira; Maria de Fátima Pires da Silva Machado

2003-01-01

133

Analysis of ergot alkaloids — a review  

Microsoft Academic Search

Methods for detection and determination of ergot alkaloids in grains, grasses, feeds and grain foods are reviewed. They incorporate\\u000a simple detection procedures - colorimetry, thin layer chromatography and enzyme-linked immunosorbent assay - or instrumental\\u000a procedures such as liquid chromatography with fluorescence, mass spectrometric (MS) or MS\\/MS detection, capillary zone electrophoresis,\\u000a and direct MS\\/MS.

P. M. Scott

2007-01-01

134

Synthesis studies on the Melodinus alkaloid meloscine  

PubMed Central

The pentacyclic Melodinus alkaloid (±)-meloscine was synthesized in 19 chemical steps from 2-bromobenzaldehyde through a route featuring an allenyl azide cyclization cascade to deliver the core azabicyclo[3.3.0]octane substructure. Peripheral functionalization of this core included a Tollens-type aldol condensation to set the quaternary center at C(20) and a diastereoselective ring closing metathesis to forge the tetrahydropyridine ring. PMID:23316092

Feldman, Ken S.; Antoline, Joshua F.

2012-01-01

135

Lycopodine-Type Alkaloids from Lycopodium japonicum.  

PubMed

Three new lycopodine-type alkaloids, 4?-hydroxyanhydrolycodoline (1), 4?,6?-dihydroxyanhydrolycodoline (2), and 6-epi-8?-acetoxylycoclavine (3), and an artifact, lycoposerramine G nitrate (4), along with seventeen related known compounds, were isolated from the club moss Lycopodium japonicum Thunb. ex Murray (Lycopodiaceae). Their structures were elucidated by extensive spectroscopic methods as well as X-ray analysis. Compounds 1-4 were evaluated for their acetylcholine esterase inhibitory activity. PMID:25089239

He, Juan; Wu, Xing-De; Liu, Fei; Liu, Yu-Cheng; Peng, Li-Yan; Zhao, Yu; Cheng, Xiao; Luo, Huai-Rong; Zhao, Qin-Shi

2014-08-01

136

A rapid screening test for lupin alkaloids  

Microsoft Academic Search

A new rapid screening procedure to test sweet lupin seeds for alkaloid content was developed using CHCl3 as solvent and acid-base titration with p-toluenesulphonic acid with tetrabromophenolphthalein ethyl ester as indicator. Seed samples of 29 cultiyars from 3 lupin species were tested. The test has proved reliable in screening new sweet lupin varieties which may still contain substantial amounts of

L. P. Ruiz Jr

1977-01-01

137

Berberine: A naturally occurring phototoxic alkaloid  

Microsoft Academic Search

The isoquinoline alkaloid berberine, present in nine different plant families was found to be phototoxic to mosquito larvae. In the presence of near UV the LC50 for acute 24-hr toxicity was 8.8 ppm compared to 250 ppm for dark controls. Mosquito larvae that were treated with 10 ppm berberine plus near UV for 24 hr and then transferred to berberine-free

B. J. R. Philogène; J. T. Arnason; G. H. N. Towers; Z. Abramowski; F. Campos; D. Champagne; D. McLachlan

1984-01-01

138

LOLINE ALKALOID BIOSYNTHESIS GENE EXPRESSION IN EPICHLOE ENDOPHYTES OF GRASSES.  

E-print Network

??Loline alkaloids (LA) are secondary metabolites produced by Epichloandamp;euml; (anamorph, Neotyphodium) grass endophytes. They are toxic and deterrent to a broad range of herbivorous insects… (more)

ZHANG, DONG-XIU

2008-01-01

139

Bioactive alkaloid extracts from Narcissus broussonetii: mass spectral studies.  

PubMed

Plants of the Amaryllidaceae family are a well-known source of tetrahydroisoquinoline alkaloids with a wide range of biological activities, including antiviral, antitumoral, antiparasitic, psychopharmacological, and acetylcholinesterase inhibitory, among others. Recent advances in the use of GC or LC coupled to MS have allowed a chemically guided isolation of uncommon and bioactive alkaloids. In the present work, analytical methods were applied to study the alkaloid profile of Narcissus broussonetii, a plant endemic to North Africa. Using the GC-MS technique and an in-home mass fragmentation database, twenty-three alkaloids were identified, including the very rare dinitrogenous alkaloids obliquine, plicamine, and secoplicamine. Applying LC-ESI-LTQ-Orbitrap-MS, fragmentation profiles were found to be similar for obliquine and plicamine but different for secoplicamine. Pretazettine, a potent cytotoxic alkaloid, was also isolated from N. broussonetii, although its identification by GC-MS was only possible after a BSTFA-derivatization. The silylated crude methanolic extract only showed the presence of pretazettine-TMS, confirming that tazettine was formed after the alkaloid extraction. The same observation was made in Narcissus cultivars in which tazettine had been detected as the major alkaloid. As part of an ongoing project on MS of Amaryllidaceae alkaloids, the silylated tazettine and pretazettine were studied by GC-MS/MS, and found to differ in their fragmentation routes. Finally, the EtOAc extract of N. broussonetii showed notable in vitro activity against Trypanosoma cruzi, with an IC(50) value of 1.77 ?g/ml. PMID:22673940

de Andrade, Jean Paulo; Pigni, Natalia Belén; Torras-Claveria, Laura; Berkov, Strahil; Codina, Carles; Viladomat, Francesc; Bastida, Jaume

2012-11-01

140

Binding Parameters of Alkaloids Berberine and Sanguinarine with DNA  

E-print Network

We study the interaction of berberine and sanguinarine (plant alkaloids) with DNA in aqueous solutions, by using optical spectroscopy methods (absorption and fluorescence). The dependencies of alkaloid spectral characteristics on the concentration ratio N/c between the DNA base pairs and alkaloid molecules in the solutions are considered, and the manifestations of the alkaloid-DNA binding are revealed. The character of binding is found to depend on N/c. The parameters of the binding of berberine and sanguinarine with DNA are determined, by using the modified Scatchard and McGhee-von Hippel equations

Gumenyuk, V G; Kutovyy, S Yu; Yashchuk, V M; Zaika, L A

2012-01-01

141

The ergot alkaloid gene cluster: functional analyses and evolutionary aspects.  

PubMed

Ergot alkaloids and their derivatives have been traditionally used as therapeutic agents in migraine, blood pressure regulation and help in childbirth and abortion. Their production in submerse culture is a long established biotechnological process. Ergot alkaloids are produced mainly by members of the genus Claviceps, with Claviceps purpurea as best investigated species concerning the biochemistry of ergot alkaloid synthesis (EAS). Genes encoding enzymes involved in EAS have been shown to be clustered; functional analyses of EAS cluster genes have allowed to assign specific functions to several gene products. Various Claviceps species differ with respect to their host specificity and their alkaloid content; comparison of the ergot alkaloid clusters in these species (and of clavine alkaloid clusters in other genera) yields interesting insights into the evolution of cluster structure. This review focuses on recently published and also yet unpublished data on the structure and evolution of the EAS gene cluster and on the function and regulation of cluster genes. These analyses have also significant biotechnological implications: the characterization of non-ribosomal peptide synthetases (NRPS) involved in the synthesis of the peptide moiety of ergopeptines opened interesting perspectives for the synthesis of ergot alkaloids; on the other hand, defined mutants could be generated producing interesting intermediates or only single peptide alkaloids (instead of the alkaloid mixtures usually produced by industrial strains). PMID:19695648

Lorenz, Nicole; Haarmann, Thomas; Pazoutová, Sylvie; Jung, Manfred; Tudzynski, Paul

2009-01-01

142

Alkaloid patterns in some varieties of Datura stramonium.  

PubMed

A comparative GC-MS investigation of the alkaloid patterns of three varieties of Datura stramonium vars. stramonium, tatula and godronii, was carried out. Twenty-five tropane alkaloids were identified in the plant organs. Alkaloid patterns of the roots, leaves and seeds of the varieties grown at equal conditions in Bulgaria were very similar. In contrast, alkaloid pattern of D. stramonium var. stramonium, grown in Egypt, showed significant differences indicating that it is influenced more strongly by the environmental factors than genetic ones. PMID:16492393

Berkov, Strahil; Zayed, Rawia; Doncheva, Tsvetelina

2006-04-01

143

Huperserines A-E, Lycopodium alkaloids from Huperzia serrata.  

PubMed

A phytochemical study on Huperzia serrata led to the isolation of four new 5-deoxyfawcettimine-related Lycopodium alkaloids, huperserines A-D (1-4), and one new lycodine-type alkaloid, huperserine E (5). Their structures were elucidated based on spectroscopic data, including 1D and 2D NMR techniques. 5-Carbonyl or 5-hydroxyl group is a typical characteristic of lycopodine- and fawcettimine-type alkaloids. This is the first report of the 5-deoxyfawcettimine type Lycopodium alkaloids. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that huperserine E exhibited moderate anti-AChE activity with an IC50 value of 6.71?M. PMID:25218968

Jiang, Wei-Wei; Liu, Fei; Gao, Xiu; He, Juan; Cheng, Xiao; Peng, Li-Yan; Wu, Xing-De; Zhao, Qin-Shi

2014-12-01

144

Alkaloids from the root of Isatis indigotica.  

PubMed

Seventeen new alkaloids (1-17) and 14 known analogues have been isolated from an aqueous extract of the root of Isatis indigotica. The structures and absolute configurations of these compounds were determined by extensive spectroscopic data analysis, including 2D NMR, single-crystal X-ray crystallography using anomalous scattering of Cu K? radiation, and electronic circular dichroism spectra calculations based on the quantum-mechanical time-dependent density functional theory. Compounds 1, 2, and 3 are the first examples of natural products with unique linkages between a molecule of 2-(4-methoxy-1H-indol-3-yl)acetonitrile and 2-(1H-indol-3-yl)acetonitrile, 2-(4-methoxy-1H-indol-3-yl)acetonitrile, and 4-hydroxyphenylethane, respectively. Compounds (-)-4 and (+)-4 represent the first natural products with the pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline skeleton. Some structural assignments for the new alkaloids suggest that the assignments made for certain previously reported alkaloids require revision. Compounds 1-3 and arvelexin (18) show antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2), with IC(50) values of 3.70-12.35 ?M, and 17 inhibits Coxsackie virus B3 replication with an IC(50) of 6.87 ?M. PMID:22694318

Chen, Minghua; Gan, Lishe; Lin, Sheng; Wang, Xiaoliang; Li, Li; Li, Yuhuan; Zhu, Chenggen; Wang, Yanan; Jiang, Bingya; Jiang, Jiandong; Yang, Yongchun; Shi, Jiangong

2012-06-22

145

Exploiting alkaloid biosynthesis in Madagascar periwinkle to obtain natural product derivatives and new biocatalysts  

E-print Network

Plant alkaloid biosynthesis produces many natural products with medicinal value. For example, vinblastine and vincristine from Catharanthus roseus monoterpene indole alkaloid biosynthesis, and camptothecin derivatives from ...

Bernhardt, Peter, Ph. D. Massachusetts Institute of Technology

2010-01-01

146

A homolog of tocopherol C-methyltransferases catalyzes N-methylation in anticancer alkaloid biosynthesis  

E-print Network

Madagascar periwinkle (Catharanthus roseus) is the sole source of the anticancer drugs vinblastine and vincristine, bisindole alkaloids derived from the dimerization of the terpenoid indole alkaloids vindoline and ...

Liscombe, David K.

147

Ergot alkaloids--biology and molecular biology.  

PubMed

EA have been a major benefit, and a major detriment, to humans since early in recorded history. Their medicinal properties have been used, and continue to be used, to aid in childbirth, with new uses being found in the treatment of neurological and cardiovascular disorders. The surprisingly broad range of pharmaceutical uses for EA stems from their affinities for multiple receptors for three distinct neurotransmitters (serotonin, dopamine, and adrenaline), from the great structural diversity of natural EA, and from the application of chemical techniques that further expand that structural diversity. The dangers posed by EA to humans and their livestock stem from the ubiquity of ergot fungi (Claviceps species) as parasites of cereals, and of related grass endophytes (Epichloë, Neotyphodium, and Balansia species) that may inhabit pasture grasses and produce toxic levels of EA. Further concerns stem from saprophytic EA producers in the genera Aspergillus and Penicillium, especially A. fumigatus, an opportunistic pathogen of humans. Numerous fungal species produce EA with a wide variety of structures and properties. These alkaloids are associated with plants in the families Poaceae, Cyperaceae, and Convolvulaceae, apparently because these plants can have symbiotic fungi that produce EA. Pharmacological activities of EA relate to their specific structures. Known as potent vasoconstrictors, the ergopeptines include a lysergic acid substituent with an amide linkage to a complex cyclol-lactam ring structure generated from three amino acids. Simpler lysergyl amides and clavines are more apt to have oxytonic or psychotropic activities. One of the lysergyl amides is LSD (5), the most potent hallucinogen known. The EA biosynthetic pathway in Claviceps species has been studied extensively for many decades, and recent studies have also employed epichloës and A. fumigatus. The early pathway, shared among these fungi, begins with the action of an aromatic prenyl transferase, DMATrp synthase, which links a dimethylallyl chain to L-tryptophan. When the dmaW gene encoding DMATrp synthase was cloned and sequenced, the predicted product bore no identifiable resemblance to other known prenyl transferases. The dma W genes of Claviceps species are present in clusters of genes, several of which also have demonstrated roles in EA biosynthesis. In many other fungi, dma W homologues are identifiable in otherwise very different gene clusters. The roles of DMA Trp synthase homologues in these other fungi are probably quite variable. One of them is thought to prenylate the phenolic oxygen of L-tyrosine, and another catalyzes the unusual reverse prenylation reaction in the biosynthesis of fumigaclavine C(10), an EA characteristic of A. fumigatus. The second step of the EA pathway is N-methylation of DMATrp (12) to form 13, which is then subjected to a series of oxidation/oxygenation and reduction reactions to generate, in order, chanoclavine-I (16), agroclavine (19), and elymoclavine (6). Shunt reactions generate a wide variety of other clavines. Two epimerizations occur in this pathway: one from 12 to 16, the other from 16 to 19. Further oxidation of 6, catalyzed by the cytochrome-P450 CloA, generates lysergic acid (1). An unusual NRPS complex, lysergyl peptide synthetase (LPS), is responsible for linking 1 to three hydrophobic L-amino acids to generate the ergopeptide lactams. The LPS complex includes two polypeptides, one (LPS 2) possessing a single module for activation of 1, and the other (LPS 1) possessing three modules, each specifying one of the L-amino acids. Variations in LPS 1 sequences are associated with variations in the incorporated amino acids, leading to differences between strain chemotypes, and even multiple ergopeptines within strains. For example, C. purpurea P1 produces two distinct ergopeptines (ergotamine (4) and ergocryptine (Table I)), each of which is believed to be generated by multiple LPS 1 subunits encoded by separate, but related, genes (lpsA1 and lpsA2). The main ecological roles of EA in nature are probably to protec

Schardl, Christopher L; Panaccione, Daniel G; Tudzynski, Paul

2006-01-01

148

The Alkaloid Alstonine: A Review of Its Pharmacological Properties  

Microsoft Academic Search

Indole compounds, related to the metabolism of tryptophan, constitute an extensive family, and are found in bacteria, plants and animals. Indolic compounds possess significant and complex physiological roles, and especially indole alkaloids have historically constituted a class of major importance in the development of new plant derived drugs. The indole alkaloid alstonine has been identified as the major component of

E. Elisabetsky; L. Costa-Campos

2006-01-01

149

Evolution of alkaloid biosynthesis in the genus Narcissus.  

PubMed

In an attempt to reveal the relationships between alkaloid biosynthesis and phylogeny, we investigated by GC-MS the alkaloid patterns of 22 species and 3 hybrids (from 45 locations) from seven main sections of the genus Narcissus (Amaryllidaceae). The results indicate that the first alkaloids to evolve in the genus Narcissus were of the lycorine- and homolycorine-type. The alkaloid pattern of the Nevadensis section supports its recent separation from the Pseudonarcissus section. The plants of Narcissus pallidulus (Ganymedes section) show a predominance of Sceletium-type compounds, which are quite rare in the Amaryllidaceae family. Two successful evolutionary strategies involving alkaloid biosynthesis and leading to an expansion in taxa and occupied area were determined. Firstly, a diversification of alkaloid patterns and a high alkaloid concentration in the organs of the large Narcissus species (in the Pseudonarcissus section) resulted in an improved chemical defence in diverse habitats. Secondly, both plant size and alkaloid biosynthesis were reduced (in the Bulbocodium and Apodanthi sections) relegated to dry pastures and rocky places. PMID:24461780

Berkov, Strahil; Martínez-Francés, Vanessa; Bastida, Jaume; Codina, Carles; Ríos, Segundo

2014-03-01

150

ORCAnization of jasmonate-responsive gene expression in alkaloid metabolism  

Microsoft Academic Search

Jasmonic acid is an important plant stress signalling molecule. It induces the biosynthesis of defence proteins and protective secondary metabolites. In alkaloid metabolism, jasmonate acts by coordinate activation of the expression of multiple biosynthesis genes. In terpenoid indole alkaloid metabolism and primary precursor pathways, jasmonate induces gene expression and metabolism via ORCAs, which are members of the AP2\\/ERF-domain family of

Johan Memelink; Rob Verpoorte; Jan W Kijne

2001-01-01

151

Identification of the quinolizidine alkaloids in Sophora leachiana  

Technology Transfer Automated Retrieval System (TEKTRAN)

Sophora is a diverse genus representing herbs, shrubs, and trees that occurs throughout the world, primarily in the northern hemisphere. Sophora species contain a variety of quinolizidine alkaloids that are toxic and potentially teratogenic. However, there are no previous reports on the alkaloid c...

152

Anti-inflammatory activity of diterpene alkaloids from Aconitum baikalense.  

PubMed

We compared anti-inflammatory activity of individual diterpene alkaloids isolated from Aconitum baikalense (napelline, songorine, hypaconitine, mesaconitine, 12-epinapelline N-oxide) under conditions of acute inflammation of different genesis. The tested substances showed high antiexudative activity comparable with that of sodium diclofenac. Unlike nonsteroidal anti-inflammatory drugs, diterpene alkaloids exerted no ulcerogenic effect. PMID:24770754

Nesterova, Yu V; Povetieva, T N; Suslov, N I; Zyuz'kov, G N; Aksinenko, S G; Pushkarskii, S V; Krapivin, A V

2014-03-01

153

Larkspur poisoning: toxicology and alkaloid structure–activity relationships  

Microsoft Academic Search

Systematic approaches to taxonomic classifications of the tall larkspur spp. have been developed using traditional chemical methods to profile alkaloids, comparison of relative toxicity of individual alkaloids, plant morphology\\/taxonomy and molecular genetics. Using these methods (papers published in this series) toxicology of three distinct species of tall larkspurs including Delphinium glaucum, Delphinium barbeyi and Delphinium occidentale is described. Tall larkspurs

K. E Panter; G. D Manners; B. L Stegelmeier; S Lee; D. R Gardner; M. H Ralphs; J. A Pfister; L. F James

2002-01-01

154

Aporphine alkaloids of Cinnamomum mollissimum and their bioactivities.  

PubMed

A chemical investigation of the crude extracts of Cinnamomum mollissimum bark resulted in the isolation of five aporphine alkaloids, namely N-methyl-1,2,10-trimethoxyaporphine, N-methylhernagine, N-methylhemovine, hernagine and hernovine. Their structures were elucidated by spectral analysis. The alkaloid crude extract demonstrated significant antibacterial and antioxidant activities. PMID:24660455

Masnon, Fatin Fasihah; Hassan, Najmah P S; Ahmad, Farediah

2014-01-01

155

A new alkaloid isolated from Abies webbiana leaf  

PubMed Central

A new alkaloid namely 1-(4’-methoxyphenyl)-aziridine was isolated from the leaf of Abies webbiana Lindl. (Pinaceae), grown in Sikkim Himalayan region of India. Its chemical structure was elucidated on the basis of elemental and spectral analyses. This is the first experimental report of the isolation of any alkaloid from A. webbiana. PMID:21808564

Ghosh, Ashoke K.; Sen, Debanjan; Bhattacharya, Sanjib

2010-01-01

156

Indole Alkaloids From Tissue-Cultured Tabernanthe Iboga H. Bn  

Microsoft Academic Search

Tissue lines, selected from explants of Tabernanthe iboga H. Bn. and cultured in shake flasks, produced and released from three to five indole alkaloids into the culture medium. the iboga alkaloids in order of their relative abundance were ibogaine, dihydroxyibogamine, ibogamine, voacangine, and ibogaline. All five compounds have the same basic ring structure as ibogaine, a putative anti-addictive drug. Three

Dominick V. Basile; Michell S. Punch; John Pablo; Bruce Brenner; W. Lee Hearn; Deborah C. Mash

1999-01-01

157

Tall fescue seed extraction and partial purification of ergot alkaloids  

Technology Transfer Automated Retrieval System (TEKTRAN)

Many substances in the tall fescue/endophyte association (Schedonorus arundinaceus/Epichloë coenophiala) have biological activity. Of these compounds only the ergot alkaloids are known to have significant mammalian toxicity and the predominant ergot alkaloids are ergovaline and ergovalinine. Because...

158

Indole alkaloids from leaves and twigs of Rauvolfia verticillata.  

PubMed

Seven new indole alkaloids, rauverines A-G (1-7), and 19 known indole alkaloids were isolated from the leaves and twigs of Rauvolfia verticillata. All compounds showed no cytotoxicity against five human cancer cell lines, human myeloid leukemia (HL-60), hepatocellular carcinoma (SMMC-7721), lung cancer (A-549), breast cancer (MCF-7), and colon cancer (SW480) cells. PMID:24266393

Zhang, Bing-Jie; Peng, Lei; Wu, Zhi-Kun; Bao, Mei-Fen; Liu, Ya-Ping; Cheng, Gui-Guang; Luo, Xiao-Dong; Cai, Xiang-Hai

2013-01-01

159

MONITORING THE PRESENCE OF ERGOT ALKALOIDS IN FORAGE ANIMAL SAMPLES  

Technology Transfer Automated Retrieval System (TEKTRAN)

Novel Aspect Initial liquid chromatography tandem mass spectrometry method development for metabolite profiling of ergot alkaloids consumed by forage animals Introduction The presence of ergot alkaloids in forages has been reported to produce acute toxicity when consumed by forage animals. A meth...

160

Angustimine and angustifolimine: two new alkaloids from Daphniphyllum angustifolium.  

PubMed

Two new alkaloids, angustimine (1) featuring an unprecedented skeleton, and angustifolimine (2) being a rare diamino Daphniphyllum alkaloid, were isolated from Daphniphyllum angustifolium. Their structures were elucidated by extensive spectroscopic analysis. The biosynthetic origin of 1 was postulated. Cytotoxic activities of 1 and 2 were tested, and all of them were inactive. PMID:21469700

Zhang, Chuan-Rui; Fan, Cheng-Qi; Dong, Shi-Hui; Liu, Hong-Bing; Zhou, Wen-Bin; Wu, Yan; Yue, Jian-Min

2011-05-01

161

Significance, chemistry and determination of ergot alkaloids: A review  

Microsoft Academic Search

The purpose of this paper is to summarize the most relevant and recent information available on ergot alkaloids. This includes information about their occurrence, toxicity, chemistry, statutory limits, and their significance in feed and food. Recently, in 2005, the European Food Safety Authority (EFSA) concluded that validated analytical methods for the quantification of ergot alkaloids in feed materials are needed.

R. Krska; C. Crews

2008-01-01

162

Alkaloid variability in Leucojum aestivum from wild populations.  

PubMed

Leucojum aestivum (summer snowflake) is a plant species used for the extraction of galanthamine, an acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. Extracts from bulbs collected from 18 Bulgarian populations and from shoot-clumps obtained in vitro from 8 different populations showed variations in their alkaloid composition. Nineteen alkaloids were detected in the studied samples by GC-MS. Typically, the alkaloid fractions of L. aestivum bulbs were dominated by galanthamine type compounds, but lycorine, haemanthamine and homolycorine type alkaloids were also found as dominant compounds in some of the samples. Extracts from the shoot-clumps obtained in vitro were found to contain galanthamine or lycorine as main alkaloids. The galanthamine content ranged from 28 to 2104 microg/g dry weight in the bulbs, and from traces to 454 microg/g dry weight in the shoot-clumps. PMID:18069233

Georgieva, Liliya; Berkov, Strahil; Kondakova, Violeta; Bastida, Jaume; Viladomat, Francesc; Atanassov, Atanas; Codina, Carles

2007-01-01

163

Estimation of total alkaloid in Chitrakadivati by UV-Spectrophotometer  

PubMed Central

Background: Herbal formulation standardization by adopting newer technique is need of the hour in the field of Ayurvedic pharmaceutical industry. As very few reports exist. These kind of studies would certainly widen the herbal research area. Chitrakadivati is one such popular herbal formulation used in Ayurveda. Many of its ingredients are known for presence of alkaloids. Methodology: Presence of alkaloid was tested qualitatively by Dragondroff's method then subjected to quantitative estimation by UV-Spectrophotometer. This method is based on the reaction between alkaloid and bromocresol green (BCG). Results and Conclusion: Study discloses that out of 16 ingredients, 9 contain alkaloid. Chitrakadivati has shown 0.16% of concentration of alkaloid and which is significantly higher than it's individual ingredients. PMID:23661869

Ajanal, Manjunath; Gundkalle, Mahadev B.; Nayak, Shradda U.

2012-01-01

164

Alkaloids; Strychnine, Codeine, Heroin, and Morphine  

NSDL National Science Digital Library

The featured molecules this month come from the article "The Conversion of Carboxylic Acids to Ketones: A Repeated Discovery" by John W. Nicholson and Alan D. Wilson. The authors describe the repeated discovery of this reaction and illustrate its central role in Woodward's total synthesis of strychnine. Strychnine is a member of a large class of nitrogen heterocycles known as alkaloids, a name derived from the fact that all produce basic solutions in water. Other well-known members of this class of compounds, all of which are pharmacologically active, are nicotine, atropine (deadly nightshade), quinine, lysergic acid, cocaine, and the three structurally similar compounds codeine, heroin, and morphine.

165

Concise Synthesis of Alkaloid (-)-205B.  

PubMed

Described herein is a short total synthesis of alkaloid (-)-205B (1) by means of an anti-selective SN2' alkylation of an attractively functionalized cyclopropanol and diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation. The synthesis features a general route to cis- or trans-2,6-disubstituted piperidines by lithium aluminum hydride reduction of the imine intermediate by an appropriate choice of solvent and cis- or trans-2,5-disubstituted pyrrolidines by an exceptional level of chirality transfer from a pendant allene. Particularly noteworthy are the brevity and convergence made possible by a segment-coupling strategy. PMID:25635954

Rao, Nagavaram Narsimha; Cha, Jin Kun

2015-02-18

166

Alkaloids of the Sedum acre -group ( Crassulaceae )  

Microsoft Academic Search

The 16 species of theSedum acre-group were investigated for the presence of alkaloids. They areS. acre ofS. ser.Acria, S. alpestre, S. annuum, S. apoleipon, S. borissovae, S. euxinum, S. grisebachii, S. laconicum, S. multiceps, S. sexangulare, S. tuberiferum, S. tuberosum, S. ursi, andS. urvillei ofS. ser.Alpestria, S. samium ofS. ser.Samia, andS. litoreum ofS. ser.Litorea. S. acre differs significantly from the

Jan F. Stevens; HENK HENDRIKS; Theo M. Malingré

1993-01-01

167

Steroidal alkaloid glycosides from tomato (Lycopersicon esculentum).  

PubMed

Three new steroidal alkaloid glycosides, lycoperosides F-H (1-3), were isolated from tomato fruits (Lycopersicon sculentum) along with lycoperosides A-D, esculeoside A, and rutin. The structures of these glycosides were characterized as the 3-O-beta-lycotetraosides of 23(R)-23-acetoxy-27-hydroxy-27-O-beta-d-glucopyranosyltomatidine (1), (23S,24R)-23-acetoxy-24-O-beta-d-glucopyranosylsoladulcidine-24-ol (2), and 22-isopimpifolidine (3), by means of their spectroscopic data. Also obtained was the new natural product lycoperodine-1 (4). PMID:15043444

Yahara, Shoji; Uda, Noriko; Yoshio, Eri; Yae, Emiko

2004-03-01

168

Study on the anti-inflammatory action of Berberis vulgaris root extract, alkaloid fractions and pure alkaloids  

Microsoft Academic Search

Extracts obtained from the roots of Berberidaceae species have been used in Eastern and Bulgarian folk medicine in rheumatic and other chronic inflammatory disorders. The investigations of the chemical composition and immunological properties show that their activity is mainly due to the alkaloid constituents. In the present study the anti-inflammatory properties of total ethanol extract (TEE), three alkaloid fractions, a

Nina Ivanovska; Stefan Philipov

1996-01-01

169

Biochemical Systematics and Ecology 29 (2001) 551561 Transfer of quinolizidine alkaloids from hosts  

E-print Network

Biochemical Systematics and Ecology 29 (2001) 551­561 Transfer of quinolizidine alkaloids from have reduced herbivory when obtaining alkaloids from the hosts Lupinus argenteus and L. texensis alkaloid-containing hosts. To determine if alkaloids are present in all tissues of plants parasitizing

Adler, Lynn

170

Leaf herbivory and nutrients increase nectar alkaloids Lynn S. Adler,1  

E-print Network

LETTER Leaf herbivory and nutrients increase nectar alkaloids Lynn S. Adler,1 * Michael Wink,2 on Nicotiana tabacum nectar and leaf alkaloids, floral traits and moth oviposition. We found a positive phenotypic correlation between nectar and leaf alkaloids. Herbivory induced alkaloids in nectar

Adler, Lynn

171

Neurotoxic Alkaloids: Saxitoxin and Its Analogs  

PubMed Central

Saxitoxin (STX) and its 57 analogs are a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs). PSTs are the causative agents of paralytic shellfish poisoning (PSP) and are mostly associated with marine dinoflagellates (eukaryotes) and freshwater cyanobacteria (prokaryotes), which form extensive blooms around the world. PST producing dinoflagellates belong to the genera Alexandrium, Gymnodinium and Pyrodinium whilst production has been identified in several cyanobacterial genera including Anabaena, Cylindrospermopsis, Aphanizomenon Planktothrix and Lyngbya. STX and its analogs can be structurally classified into several classes such as non-sulfated, mono-sulfated, di-sulfated, decarbamoylated and the recently discovered hydrophobic analogs—each with varying levels of toxicity. Biotransformation of the PSTs into other PST analogs has been identified within marine invertebrates, humans and bacteria. An improved understanding of PST transformation into less toxic analogs and degradation, both chemically or enzymatically, will be important for the development of methods for the detoxification of contaminated water supplies and of shellfish destined for consumption. Some PSTs also have demonstrated pharmaceutical potential as a long-term anesthetic in the treatment of anal fissures and for chronic tension-type headache. The recent elucidation of the saxitoxin biosynthetic gene cluster in cyanobacteria and the identification of new PST analogs will present opportunities to further explore the pharmaceutical potential of these intriguing alkaloids. PMID:20714432

Wiese, Maria; D’Agostino, Paul M.; Mihali, Troco K.; Moffitt, Michelle C.; Neilan, Brett A.

2010-01-01

172

Neurotoxic alkaloids: saxitoxin and its analogs.  

PubMed

Saxitoxin (STX) and its 57 analogs are a broad group of natural neurotoxic alkaloids, commonly known as the paralytic shellfish toxins (PSTs). PSTs are the causative agents of paralytic shellfish poisoning (PSP) and are mostly associated with marine dinoflagellates (eukaryotes) and freshwater cyanobacteria (prokaryotes), which form extensive blooms around the world. PST producing dinoflagellates belong to the genera Alexandrium, Gymnodinium and Pyrodinium whilst production has been identified in several cyanobacterial genera including Anabaena, Cylindrospermopsis, Aphanizomenon Planktothrix and Lyngbya. STX and its analogs can be structurally classified into several classes such as non-sulfated, mono-sulfated, di-sulfated, decarbamoylated and the recently discovered hydrophobic analogs--each with varying levels of toxicity. Biotransformation of the PSTs into other PST analogs has been identified within marine invertebrates, humans and bacteria. An improved understanding of PST transformation into less toxic analogs and degradation, both chemically or enzymatically, will be important for the development of methods for the detoxification of contaminated water supplies and of shellfish destined for consumption. Some PSTs also have demonstrated pharmaceutical potential as a long-term anesthetic in the treatment of anal fissures and for chronic tension-type headache. The recent elucidation of the saxitoxin biosynthetic gene cluster in cyanobacteria and the identification of new PST analogs will present opportunities to further explore the pharmaceutical potential of these intriguing alkaloids. PMID:20714432

Wiese, Maria; D'Agostino, Paul M; Mihali, Troco K; Moffitt, Michelle C; Neilan, Brett A

2010-01-01

173

Comparative study of the alkaloids in tribe Datureae and their chemosystematic significance  

Microsoft Academic Search

Sixty-six tropane alkaloids from crude leaf and root alkaloid mixtures of 12 different species and their varieties and subspecies from tribe Datureae were determined by GC–MS. The alkaloids 3?-hydroxy-6?-acetoxytropane, 3-propionyloxy-6-hyroxytropane, 3?-hydroxy-6?-tigloyloxytropane, 3?-tigloyloxy-6?-acetoxytropane and 3-tigloyloxy-7-isobutyryloxytropane are new reported tropane alkaloids.The alkaloid profile of the species supported the recognition of distinct groups within the tribe Datureae. The genus Brugmansia is well separated

Tsvetelina Doncheva; Strahil Berkov; Stefan Philipov

2006-01-01

174

Quinolizidine alkaloids in Genista acanthoclada and its holoparasite, Cuscuta palaestina  

Microsoft Academic Search

About 20 quinolizidine alkaloids were identified inGenista acanthoclada by capillary GLC and GLC-MS, such as sparteine, 11,12-dehy-drosparteine, retamine,N-methylcytisine, cytisine, 17-oxosparteine, lupanine,a-isolupanine, 5,6-dehydrolupanine, 10-oxosparteine,N-carbomethoxycytisine, 17-oxoretamine,N-formylcytisine,N-acetylcytisine, and anagyrine. Its phloem-feeding holoparasiteCuscuta palaestina contained alkaloids too, such as sparteine, 11,12-dehydrosparteine, retamine,N-methylcytisine, cytisine, 17-oxosparteine, lupanine,N-carbomethoxycytisine, and anagyrine. Whereas sparteine, retamine, 17-oxosparteine, and cytisine are the main alkaloids ofG. acanthoclada, lupanine, cytisine,N-methylcytisine, and anagyrine are

Michael Wink; Ludger Witte

1993-01-01

175

Five new fawcettimine-related alkaloids from Lycopodium japonicum Thunb.  

PubMed

Five new trace alkaloids with fawcettimine-related structures (1-5), i.e., 6-hydroxyl-6,7-dehydrolycoflexine (1), 6-hydroxyl-6,7-dehydro-8-deoxy-13-dehydroserratinine (2), together with three known ones (6-8), were isolated from the club moss Lycopodium japonicum Thunb. Their structures were elucidated by extensive NMR spectroscopic analysis, HRESIMS, CD and comparison with known ones. Compounds 1 and 2 are characterized by the enol moiety that is rarely reported in Lycopodium alkaloids, and Compound 5 is the second example of Lycopodium alkaloids with a C-16-C-4 linkage. A plausible biogenetic pathway for the isolates was proposed. PMID:23994627

Wang, Xiao-Jing; Li, Li; Yu, Shi-Shan; Ma, Shuang-Gang; Qu, Jing; Liu, Yun-Bao; Li, Yong; Wang, Yadan; Tang, Weibin

2013-12-01

176

The role of biocatalysis in the asymmetric synthesis of alkaloids  

PubMed Central

Alkaloids are not only one of the most intensively studied classes of natural products, their wide spectrum of pharmacological activities also makes them indispensable drug ingredients in both traditional and modern medicine. Among the methods for their production, biotechnological approaches are gaining importance, and biocatalysis has emerged as an essential tool in this context. A number of chemo-enzymatic strategies for alkaloid synthesis have been developed over the years, in which the biotransformations nowadays take an increasingly ‘central’ role. This review summarises different applications of biocatalysis in the asymmetric synthesis of alkaloids and discusses how recent developments and novel enzymes render innovative and efficient chemo-enzymatic production routes possible.

2013-01-01

177

[Extraction and HPLC analysis of alkaloids in goldenseal].  

PubMed

An ambient extraction of goldenseal root powder followed by HPLC analysis of the alkaloids on a Zorbax Rapid Resolution Eclipse XDB-C18 column provides an accurate method for the determination of key alkaloids in goldenseal, including berberine and hydrastine. The extraction and HPLC analysis can be applied to several other alkaloids, including canadine, hydrastinine, and palmatine, and may be applicable to other berberine-containing plant roots. The Rapid Resolution Eclipse XDB-C18 column is used for an isocratic separation with high resolution of all componentsin under 15 minutes. PMID:15969129

Weber, Holly A; Joseph, Maureen

2004-03-01

178

Total Synthesis and Study of Myrmicarin Alkaloids  

PubMed Central

The myrmicarins are a family of air and temperature sensitive alkaloids that possess unique structural features. Our concise enantioselective synthesis of the tricyclic myrmicarins enabled evaluation of a potentially biomimetic assembly of the complex members via direct dimerization of simpler structures. These studies revealed that myrmicarin 215B undergoes efficient and highly diastereoselective Brønsted acid-induced dimerization to generate a new heptacyclic structure, isomyrmicarin 430A. Mechanistic analysis demonstrated that heterodimerization between myrmicarin 215B and a conformationally restricted azafulvenium ion precursor afforded a functionalized isomyrmicarin 430A structure in a manner that was consistent with a highly efficient, non-concerted ionic process. Recent advancement in heterodimerization between tricyclic derivatives has enabled the preparation of strategically functionalized hexacyclic structures. The design and synthesis of structurally versatile dimeric compounds has greatly facilitated manipulation of these structures en route to more complex myrmicarin derivatives. PMID:19585010

Ondrus, Alison E.

2010-01-01

179

Total synthesis of alkaloid 205B.  

PubMed

Concise and highly stereocontrolled total syntheses of racemic and enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 and 7 in overall yields of 8 and 8%, respectively. The assembly of the core of the natural product relies on a stereoselective Tsuji-Trost allylic amination reaction and a ring-closing metathesis. The synthesis features the use of an N-acylpyridinium salt reaction to introduce the first stereocenter and an unprecedented trifluoroacetic anhydride-mediated addition of an allylstannane to a vinylogous amide with complete facial selectivity. Deoxygenation of the C4 ketone proved difficult but was accomplished via a modified Barton-McCombie reaction in the presence of a catalytic amount of diphenyl diselenide. PMID:25180567

Tsukanov, Sergey V; Comins, Daniel L

2014-10-01

180

Benhamycin, novel alkaloid from terrestrial Streptomyces sp.  

PubMed

During our screening for bioactive natural compounds from microorganisms, a novel alkaloid has been isolated from a terrestrial Streptomyces sp. isolate NR12, and named as benhamycin (1). This was along with the known metabolites, uracil, thymine, p-hydroxybenzoic acid, 2'-deoxyuridin, tryptophol, indolyl-3-carboxylic acid, and indolyl-3-carbaldehyde. Chemical structure of the novel compound was determined by detailed analysis of its spectroscopic data (extensive NMR experiments, 1 & 2D, MS spectroscopy, and MS high resolution). Structurally, Benhamycin (1) is a pentacyclic aromatic compound bearing an acridine moiety lactamized with benzene. Biological studies showed that the strain extract was moderately active against Gram-positive, Gram-negative bacteria and fungi. PMID:17987502

Shaaban, Mohamed; Abdel-Aziz, Mohamed S

2007-11-01

181

Bioactive isoquinoline alkaloids from Corydalis saxicola.  

PubMed

Twelve isoquinoline alkaloids including two new nitro-containing tetrahydroprotoberberines, (-)-2,9-dihydroxyl-3,11-dimethoxy-1,10-dinitrotetrahydroprotoberberine (1) and (+)-4-nitroisoapocavidine (2), were isolated from the whole plant of Corydalis saxicola Bunting. The structures of the new compounds were established by spectroscopic analysis and chemical evidence. The inhibitory activity of these isolates against cholinesterase and canine parvovirus were evaluated. Compounds 1 and 1A, (+)-1-nitroapocavidine (5), berberine (8), palmatine (9), dehydrocavidine (10), and sanguinarine (11) showed potent inhibitory activity against acetylcholinesterase with IC(50) values of less than 10?µM, while only compound 1 possessed weak activity against canine parvovirus. Structure-activity studies demonstrated that the nitro substituents at ring A in the tetrahydroprotoberberines led to an increase in the anti-acetylcholinesterase activity. PMID:21858757

Huang, Qiao-Qin; Bi, Jun-Long; Sun, Qian-Yun; Yang, Fu-Mei; Wang, Yue-Hu; Tang, Gui-Hua; Zhao, Fu-Wei; Wang, Huan; Xu, Jin-Jin; Kennelly, Edward J; Long, Chun-Lin; Yin, Ge-Fen

2012-01-01

182

Crinine-type alkaloids from Hippeastrum aulicum and H. calyptratum.  

PubMed

An ongoing search for alkaloids in the Amaryllidaceae species using GC-MS resulted in the identification of two crinine-type alkaloids, aulicine (1) and 3-O-methyl-epimacowine, (2) from the indigenous Brazilian species Hippeastrum aulicum and Hippeastrum calyptratum, respectively. In addition, two alkaloids, 11-oxohaemanthamine (3) and 7-methoxy-O-methyllycorenine (4) were both isolated from H. aulicum. Furthermore, we provide here complete NMR spectroscopic data for the homolycorine analogues nerinine (5) and albomaculine (6). The absolute stereochemistry of the 5,10b-ethano bridge in the crinine variants was determined by circular dichroism and X-ray crystallographic analysis, thus presenting the first direct evidence for the presence of crinine-type alkaloids in the genus Hippeastrum. PMID:24768284

de Andrade, Jean Paulo; Guo, Ying; Font-Bardia, Mercè; Calvet, Teresa; Dutilh, Jullie; Viladomat, Francesc; Codina, Carles; Nair, Jerald J; Zuanazzi, Jose A Silveira; Bastida, Jaume

2014-07-01

183

Complanadine A, a new dimeric alkaloid from Lycopodium complanatum  

Microsoft Academic Search

A new dimeric alkaloid with a lycodine-type skeleton, complanadine A (1), has been isolated from the club moss Lycopodium complanatum, and the structure including the absolute stereochemistry was elucidated on the basis of spectroscopic data.

Jun'ichi Kobayashi; Yusuke Hirasawa; Naotoshi Yoshida; Hiroshi Morita

2000-01-01

184

Arginine decarboxylase as the source of putrescine for tobacco alkaloids  

NASA Technical Reports Server (NTRS)

The putrescine which forms a part of nicotine and other pyrrolidine alkaloids is generally assumed to arise through the action of ornithine decarboxylase (ODC). However, we have previously noted that changes in the activity of arginine decarboxylase (ADC), an alternate source of putrescine, parallel changes in tissue alkaloids, while changes in ODC activity do not. This led us to undertake experiments to permit discrimination between ADC and ODC as enzymatic sources of putrescine destined for alkaloids. Two kinds of evidence presented here support a major role for ADC in the generation of putrescine going into alkaloids: (a) A specific 'suicide inhibitor' of ADC effectively inhibits the biosynthesis of nicotine and nornicotine in tobacco callus, while the analogous inhibitor of ODC is less effective, and (b) the flow of 14C from uniformly labelled arginine into nicotine is much more efficient than that from ornithine.

Tiburcio, A. F.; Galston, A. W.

1986-01-01

185

New strategies for the synthesis of azepine-containing alkaloids  

E-print Network

The Stemona alkaloids are an important family of natural products which have received attention due to their unique chemical structure and important biological properties. The stemona family members contain the 4-azaazulene substructure (1...

Tallant, Matthew David

2001-01-01

186

Substrate analogs to investigate alkaloid biosynthesis in Catharanthus roseus  

E-print Network

Terpene indole alkaloids are a class of natural products produced by plants, many of which are used clinically for the treatment of human disease. Natural products, are not produced by the organism for the purpose of ...

McCoy, Elizabeth Ann, Ph. D. Massachusetts Institute of Technology

2009-01-01

187

Reprogramming alkaloid biosynthesis in Catharanthus roseus : synthetic biology in plants  

E-print Network

The medicinal plant Madagascar periwinkle (Catharanthus roseus) produces over 130 monoterpene indole alkaloid (MIA) natural products. Many of these compounds have pharmaceutical value, such as the anticancer agents vinblastine ...

Runguphan, Weerawat

2011-01-01

188

Diterpenoid alkaloids from the lateral root of Aconitum carmichaelii.  

PubMed

Twenty-six new diterpenoid alkaloids, 1-26 (1-4: hetisan-type C(20)-diterpenoid alkaloids; 5-26: aconitane C(19)-diterpenoid alkaloids), and two known analogues, hypaconitine 27 and benzoylmesaconine 28, have been isolated from a water extract of the lateral root of Aconitum carmichaelii. Compounds 7 and 8 are rare examples of conformational isomers obtained from the same material. The conformation and conformational transformation of ring A in the C(19)-diterpenoid alkaloids are discussed on the basis of NMR data analysis in combination with single-crystal X-ray crystallography of 6 and 27 by anomalous scattering of Cu K? radiation. In preliminary analgesic and toxicity assays, the isomer with ring A in the chair conformation (8 or 27) was found to be more active than that with ring A in the boat conformation (7 or 27a). In addition, 15, 16, and 19 showed neuroprotective activity. PMID:22607495

Jiang, Bingya; Lin, Sheng; Zhu, Chenggen; Wang, Sujuan; Wang, Yanan; Chen, Minghua; Zhang, Jianjun; Hu, Jinfeng; Chen, Naihong; Yang, Yongchun; Shi, Jiangong

2012-06-22

189

Novel Triterpenoidal Alkaloids from the Roots of Buxus Sempervirens  

Microsoft Academic Search

Phytochemical studies on the ethanolic extract of the roots of Buxus sempervirens of Turkish origin have yielded two novel triterpenoidal alkaloids, (+)-30-hydroxycyclomicrobuxene (1) and (-)-semperviroxazolidine (2). Their structures were established on the basis of extensive spectroscopic studies.

Atta Ur Rahman; Samina Naz; Athar Ata; M. Iqbal Choudhary; Bilge Sener; Songul Turkoz

1998-01-01

190

A New Alkaloid Ajmalimine from the Roots of Rauwolfia serpentina.  

PubMed

A new indole alkaloid ajmalimine has been isolated from the roots of RAUWOLFIA SERPENTINA collected in Thailand. Its structure, 21-(trimethoxybenzoyl)-ajmaline, was established by spectroscopic and chemical means. PMID:17269023

Siddiqui, S; Ahmad, S S; Haider, S I

1987-06-01

191

Aconite poisoning following the percutaneous absorption of Aconitum alkaloids.  

PubMed

In vitro experiment using the modified Franz-type diffusion cell has demonstrated that the human skin is permeable to aconitine and mesaconitine. To characterise the risk of systemic toxicity following the topical applications of aconite tincture and raw aconite roots, relevant reports of percutaneous absorption of Aconitum alkaloids and aconite poisoning are reviewed. Published reports indicate that aconite tincture and raw aconite roots can be absorbed through the skin into systemic circulation to cause fatal and non-fatal aconite poisoning. Both aconite tincture and raw aconite roots contain very high concentrations of Aconitum alkaloids, which allow penetration of the stratum corneum along the diffusion gradient. The risk of systemic toxicity is even higher if Aconitum alkaloids are held in occlusive contact with the skin and the epidermis (stratum corneum) is already damaged. The public should be warned of the danger in using these topical aconite preparations and the risk of systemic toxicity following percutaneous absorption of Aconitum alkaloids. PMID:22766196

Chan, Thomas Y K

2012-11-30

192

Pyrrole alkaloids from the fruits of Morus alba.  

PubMed

Phytochemical investigation of the fruits of Morus alba afforded seventeen pyrrole alkaloids including five new compounds. The structures of five new pyrrole alkaloids, named morroles B-F (4, 5, 7, 16 and 17), were determined on the basis of spectroscopic interpretations. 4-[Formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]butanoate (2) was synthesized by chemical reaction but first isolated from nature. Among isolated compounds, compounds 6 and 14 significantly inhibited pancreatic lipase activity. PMID:25467154

Kim, Seon Beom; Chang, Bo Yoon; Hwang, Bang Yeon; Kim, Sung Yeon; Lee, Mi Kyeong

2014-12-15

193

Inhibition of acetyl cholinesterase by solanaceous glycoalkaloids and alkaloids  

Microsoft Academic Search

Seven solanaceous glycoalkaloids (?-chaconine, ?2-chaconine, ?-solanine, dehydrocommersonine, commersonine, demissine and tomatine) and three alkaloids (solanidine, tomatidine\\u000a and demissidine) were tested for their ability to inhibit acetyl cholinesterase in anin vitro system. Glycoalkaloids at concentrations of 33–41 parts per million (ppm) gave cholinesterase inhibition ranging from 4.2\\u000a to 26.8%. All three alkaloids had lower anticholinesterase (4.2 to 15.4%) than the seven

Rodney J. Bushway; Sharon A. Savage; Bruce S. Ferguson

1987-01-01

194

Lyconadins C and F, new Lycopodium alkaloids from Lycopodium complanatum  

Microsoft Academic Search

New Lycopodium alkaloids, lyconadins C (1) and F (2), were isolated from the club moss Lycopodium complanatum. Lyconadin C (1) is a new C16N2-type Lycopodium alkaloid possessing unique fused-tetracyclic ring system consisting of a cycloheptene ring fused to a decahydroquinoline and pyridone rings. Lyconadin F (2) possesses a primary amide moiety in its molecular, which is the first example of

Kan’ichiro Ishiuchi; Takaaki Kubota; Haruaki Ishiyama; Shigeki Hayashi; Toshiro Shibata; Jun’ichi Kobayashi

2011-01-01

195

Scent Organ Development in Creatonotos Moths: Regulation by Pyrrolizidine Alkaloids  

Microsoft Academic Search

7-Hydroxy-6,7-dihydro-5H-pyrrolizine-1-carboxaldehyde is the major volatile component of the scent organs in males of two species of Creatonotos (Lepidoptera, Arctiidae). The biosynthesis of this presumed pheromone depends on the presence of pyrrolizidine alkaloids in plants that are ingested by the larvae. In addition, these secondary plant substances control the morphogenesis of the scent organs. This morphogenetic effect of an alkaloid has

Dietrich Schneider; Michael Boppre; Jonathan Zweig; Stephen B. Horsley; Thomas W. Bell; Jerrold Meinwald; Kurt Hansen; Eduard W. Diehl

1982-01-01

196

The isolation and identification of three alkaloids of Acacia berlandieri  

E-print Network

THE ISOLATION AND IDENTIFICATION OF THREE ALKALOIDS OF ACACIA BERLANDIERI A Thesis Herman Ray Adams Submitted to the Graduate College of ths Texas AA:M University in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE... January lp65 Major Sub)act& Biochemistry THE ISOLATION AND IDENTIFICATION OF THBEE ALKALOIDS OF ACACIA HEBLANDIEBI A Thesis Herman Bay Adams Approved as to style and content by& (Chairman of Co ttee) (Hember) (Bomber) January i&65 ACKN...

Adams, Herman Ray

1965-01-01

197

Alkaloids from Catecholamines in Adrenal Tissue: Possible Role in Alcoholism  

Microsoft Academic Search

Epinephrine and norepinephrine condensed with acetaldehyde or with formaldehyde in dilute aqueous solution at neutral pH and room temperature to form 1,2,3,4-tetrahydroisoquinoline alkaloids. Similar condensation reactions occurred in cow adrenal glands perfused with dilute aldehyde solutions at 37 degrees C. Biosynthesis of these alkaloids in vivo could play a role in altering an individual's behavior during and after the ingestion

Gerald Cohen; Michael Collins

1970-01-01

198

Evidence for an ergot alkaloid gene cluster in Claviceps purpurea  

Microsoft Academic Search

A gene (cpd1) coding for the dimethylallyltryptophan synthase (DMATS) that catalyzes the first specific step in the biosynthesis of ergot\\u000a alkaloids, was cloned from a strain of Claviceps purpurea that produces alkaloids in axenic culture. The derived gene product (CPD1) shows only 70% similarity to the corresponding\\u000a gene previously isolated from Claviceps strain ATCC 26245, which is likely to be

P. Tudzynski; K. Hölter; T. Correia; C. Arntz; N. Grammel; U. Keller

1999-01-01

199

Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum.  

PubMed

Alkaloids represent an extensive group of nitrogen-containing secondary metabolites that are widely distributed throughout the plant kingdom. The pyridine alkaloids of tobacco (Nicotiana tabacum L.) have been the subject of particularly intensive investigation, driven largely due to the widespread use of tobacco products by society and the role that nicotine (16) (see Fig. 1) plays as the primary compound responsible for making the consumption of these products both pleasurable and addictive. In a typical commercial tobacco plant, nicotine (16) comprises about 90% of the total alkaloid pool, with the alkaloids nornicotine (17) (a demethylated derivative of nicotine), anatabine (15) and anabasine (5) making up most of the remainder. Advances in molecular biology have led to the characterization of the majority of the genes encoding the enzymes directly responsible the biosynthesis of nicotine (16) and nornicotine (17), while notable gaps remain within the anatabine (15) and anabasine (5) biosynthetic pathways. Several of the genes involved in the transcriptional regulation and transport of nicotine (16) have also been elucidated. Investigations of the molecular genetics of tobacco alkaloids have not only provided plant biologists with insights into the mechanisms underlying the synthesis and accumulation of this important class of plant alkaloids, they have also yielded tools and strategies for modifying the tobacco alkaloid composition in a manner that can result in changing the levels of nicotine (16) within the leaf, or reducing the levels of a potent carcinogenic tobacco-specific nitrosamine (TSNA). This review summarizes recent advances in our understanding of the molecular genetics of alkaloid biosynthesis in tobacco, and discusses the potential for applying information accrued from these studies toward efforts designed to help mitigate some of the negative health consequences associated with the use of tobacco products. PMID:23953973

Dewey, Ralph E; Xie, Jiahua

2013-10-01

200

Asymmetric synthesis of the azabicyclic core of the Stemona alkaloids.  

PubMed

A general strategy for the construction of the 1-azabicyclo[5.3.0]decane core of Stemona alkaloids is developed. Our diversity-oriented approach exploits 1,3-dipolar cycloaddition of five-membered cyclic nitrones to C(6) olefins, followed by N-O reductive cleavage and azepine closure. The use of various enantiopure pyrroline N-oxides allows for a practical, stereoselective preparation of several putative precursors of different Stemona alkaloids. PMID:15822978

Alibés, Ramon; Blanco, Pilar; Casas, Eva; Closa, Montserrat; de March, Pedro; Figueredo, Marta; Font, Josep; Sanfeliu, Elena; Alvarez-Larena, Angel

2005-04-15

201

Gas chromatographic analysis of indole alkaloids from Tabernaemontana hilariana  

Microsoft Academic Search

A fast and efficient procedure was elaborated to identify the alkaloid constituents from Tabernaemontana hilariana (Apocynaceae). The strategy based on fractioning of the crude alkaloid fraction in small cartridges followed by thin-layer chromatography (TLC), capillary gas chromatography-flame ionization detection as well as high-resolution gas chromatography-mass spectrometry afforded voacangine, coronaridine, ibogamine pseudoindoxyl, voacangine hydroxyindolenine, 3-hydroxycoronaridine and 3-(2-oxopropyl)coronaridine.

Claudia A. L. Cardoso; Wagner Vilegas; Gilberto L. Pozetti

1997-01-01

202

Lycojaponicumins D and E: two new alkaloids from Lycopodium japonicum.  

PubMed

Two new alkaloids, lycojaponicumins D (1) and E (2), were isolated from the club moss Lycopodium japonicum. Their structures were elucidated by spectroscopic methods, calculated ECD, CD experiments and X-ray diffraction analysis. Lycojaponicumin D (1) possesses an unprecedented 5/7/6/6 tetracyclic skeleton formed by an unusual C3-C13 linkage, which is first reported in Lycopodium alkaloids. The plausible biogenetic pathway of 1 is proposed. PMID:23121621

Wang, Xiao-Jing; Liu, Yun-Bao; Li, Li; Yu, Shi-Shan; Lv, Hai-Ning; Ma, Shuang-Gang; Bao, Xiu-Qi; Zhang, Dan; Qu, Jing; Li, Yong

2012-11-16

203

Qualitative characteristics of alkaloids of species of the genus Vinca  

Microsoft Academic Search

Summary  The qualitative characterization of 38 indole alkaloids has been performed by chromatography on kieselguhr G and Silufol with\\u000a the reagents cerium ammonium sulfate and ferric chloride.\\u000a \\u000a The possibility of a preliminary determination of the chromophoric group (?-methyleneindole, indoline, indole, and hydroxyindole) of alkaloids by means of the reagents cerium ammonium sulfate and ferric\\u000a chloride has been shown.

V. Yu. Vachnadze; V. M. Malikov; Kh. T. Il'yasova; K. S. Mudzhiri; S. Yu. Yunusov

1973-01-01

204

Quantitative spectrophotometric determination of alkaloids in roots of Vinca herbacea  

Microsoft Academic Search

A new spectrophotometric method has been developed for the quantitative determination of pharmacologically active alkaloids\\u000a (maydine, reserpinine, kopsinine, tabersonine, norfluorocurarine) and their sum in roots of Vinca herbacea Walds. et Kit. The proposed technique is highly reproducible and adequately reflects the content of alkaloids in the roots\\u000a and preparations of Vinca herbacea, which allows this method to be used for

V. Yu. Vachnadze; E. Z. Dzhakeli; I. A. Dadeshidze; L. G. Kintsurashvili

2010-01-01

205

Indole Alkaloid Glycosides from the Aerial Parts of Strobilanthes cusia.  

PubMed

Three indole alkaloid glycosides, strobilanthosides A-C (1-3), two known indole alkaloid glucosides (4 and 5), and five phenylethanoid glycosides (8-10) were isolated from the aerial parts of Strobilanthes cusia. The structures of the new compounds were elucidated by spectrometric analysis, and the absolute configurations of 1 and 2 were established by ECD spectrocsopy. N'-?-d-Glucopyranosylindirubin (5) showed weak antibacterial activity (MIC 62.5-125 ?M) against Staphylococcus aureus. PMID:25427242

Gu, Wei; Zhang, Yu; Hao, Xiao-Jiang; Yang, Fu-Mei; Sun, Qian-Yun; Morris-Natschke, Susan L; Lee, Kuo-Hsiung; Wang, Yue-Hu; Long, Chun-Lin

2014-12-26

206

Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa.  

PubMed

Quaternary alkaloids are the major alkaloids isolated from Tinospora species. A previous study pointed to the necessary presence of quaternary nitrogens for strong acetylcholinesterase (AChE) inhibitory activity in such alkaloids. Repeated column chromatography of the vine of Tinospora crispa extract led to the isolation of one new protoberberine alkaloid, 4,13-dihydroxy-2,8,9-trimethoxydibenzo[a,g]quinolizinium (1), along with six known alkaloids-dihydrodiscretamine (2), columbamine (3), magnoflorine (4), N-formylannonaine (5), N-formylnornuciferine (6), and N-trans-feruloyltyramine (7). The seven compounds were isolated and structurally elucidated by spectroscopic analysis. Two known alkaloids, namely, dihydrodiscretamine and columbamine are reported for the first time for this plant. The compounds were tested for AChE inhibitory activity using Ellman's method. In the AChE inhibition assay, only columbamine (3) showed strong activity with IC50 48.1 µM. The structure-activity relationships derived from these results suggest that the quaternary nitrogen in the skeleton has some effect, but that a high degree of methoxylation is more important for acetylcholinesterase inhibition. PMID:24448061

Yusoff, Mashitah; Hamid, Hazrulrizawati; Houghton, Peter

2014-01-01

207

13,14-Dihydrocoptisine - The genuine alkaloid from Chelidonium majus.  

PubMed

The genuine major benzylisoquinoline alkaloid occurring in the traditional medicinal plant greater celandine (Chelidonium majus L.) is 13,14-dihydrocoptisine and not - as described previously - coptisine. Structure of 13,14-dihydrocoptisine was elucidated. The discrepancy between the alkaloid pattern of the living plants and that of detached and dried leaves is due to the rapid and prompt conversion of 13,14-dihydrocoptisine to coptisine in the course of tissue injuries. Indeed, apart from the major alkaloid, some minor alkaloids might also be converted; this however is not in the centre of focus of this paper. This conversion is initiated by the change of pH. In vivo 13,14-dihydrocoptisine is localized in the acidic vacuoles, where it is stable. In contrast, in the neutral milieu, which results when vacuoles are destroyed in the course of tissue injuries, the genuine alkaloid is oxidized to yield coptisine. Accordingly, when alkaloids from C.majus should be analyzed, any postmortal conversion of 13,14-dihydrocoptisine has to be prevented. PMID:25666130

Paulsen, Jana; Yahyazadeh, Mahdi; Hänsel, Sophie; Kleinwächter, Maik; Ibrom, Kerstin; Selmar, Dirk

2015-03-01

208

Cytotoxicity studies of lycorine alkaloids of the Amaryllidaceae.  

PubMed

The plant family Amaryllidaceae is renowned for its unique alkaloid constituents which possess a significant array of structural diversity. Several of these alkaloids are known for their interesting biological properties, of which galanthamine and pancratistatin have acquired a privileged status due to their relevance in the pharmaceutical arena. In particular, galanthamine represents the first prescription drug emanating from the Amaryllidaceae after its approval by the FDA in 2001 for the treatment of Alzheimer's disease. Following on this commercial success there have been sustained projections for the emergence of an anticancer agent related to pancratistatin due to the potency, selectivity, low toxicity and high tolerability typifying targets of this series of alkaloids. The lycorine series of alkaloids have also garnered widespread interest as cytotoxic agents and were amongst the earliest of the Amaryllidaceae constituents to exhibit such activity. To date over 100 of such naturally-occurring or synthetically-derived alkaloids have been screened for cytotoxic effects against a number of cancer cell lines. This survey examines the cytotoxic properties of lycorine alkaloids, highlights the outcomes of structure-activity relationship orientated studies and affords plausible insights to the mechanistic rationale behind these effects. PMID:25233606

Nair, Jerald J; van Staden, Johannes

2014-08-01

209

Distribution of Aconitum alkaloids in autopsy cases of aconite poisoning.  

PubMed

Aconite is a well-known toxic-plant containing Aconitum alkaloids such as aconitines, benzoylaconines, and aconins. We describe here the distribution of Aconitum alkaloids detected by liquid chromatography-tandem mass spectrometry (LC/MS/MS) in three autopsy cases of suicide by aconite poisoning. Case 1: a male in his fifties had eaten aconite leaves. The concentrations of jesaconitine in cardiac blood, urine, and kidney were 12.1 ng/ml, 993.0 ng/ml, and 114.2 ng/g, respectively. Case 2: a female in her fifties had eaten aconite root. The aconite root in the stomach included a high level of mesaconitine. The concentrations of mesaconitine in cardiac blood, liver, and kidney were 69.1 ng/ml, 960.9 ng/g, and 776.9 ng/g, respectively. Case 3: a male in his sixties had drunk liquor in which aconite root had been soaked. The concentrations of mesaconitine and aconitine in cardiac blood were 259.5 and 228.5 ng/ml, respectively. The Aconitum alkaloid levels were very high in the liver. The absorption of ethanol and Aconitum alkaloids might have been increased because of his having undergone total gastrectomy. In all three cases, the Aconitum alkaloid levels were high in the liver and kidney and low in the heart and cerebrum. The level in the cerebrum was lower than that in blood. Data on the distribution of the Aconitum alkaloids in the body in cases of aconite poisoning is useful to elucidate various actions of aconite alkaloids. PMID:23131306

Niitsu, Hisae; Fujita, Yuji; Fujita, Sachiko; Kumagai, Reiko; Takamiya, Masataka; Aoki, Yasuhiro; Dewa, Koji

2013-04-10

210

Transgenic and Mutation-Based Suppression of a Berberine Bridge Enzyme-Like (BBL) Gene Family Reduces Alkaloid Content in Field-Grown Tobacco.  

PubMed

Motivation exists to develop tobacco cultivars with reduced nicotine content for the purpose of facilitating compliance with expected tobacco product regulations that could mandate the lowering of nicotine levels per se, or the reduction of carcinogenic alkaloid-derived tobacco specific nitrosamines (TSNAs). A berberine bridge enzyme-like (BBL) gene family was recently characterized for N. tabacum and found to catalyze one of the final steps in pyridine alkaloid synthesis for this species. Because this gene family acts downstream in the nicotine biosynthetic pathway, it may represent an attractive target for genetic strategies with the objective of reducing alkaloid content in field-grown tobacco. In this research, we produced transgenic doubled haploid lines of tobacco cultivar K326 carrying an RNAi construct designed to reduce expression of the BBL gene family. Field-grown transgenic lines carrying functional RNAi constructs exhibited average cured leaf nicotine levels of 0.684%, in comparison to 2.454% for the untransformed control. Since numerous barriers would need to be overcome to commercialize transgenic tobacco cultivars, we subsequently pursued a mutation breeding approach to identify EMS-induced mutations in the three most highly expressed isoforms of the BBL gene family. Field evaluation of individuals possessing different homozygous combinations of truncation mutations in BBLa, BBLb, and BBLc indicated that a range of alkaloid phenotypes could be produced, with the triple homozygous knockout genotype exhibiting greater than a 13-fold reduction in percent total alkaloids. The novel source of genetic variability described here may be useful in future tobacco breeding for varied alkaloid levels. PMID:25688975

Lewis, Ramsey S; Lopez, Harry O; Bowen, Steve W; Andres, Karen R; Steede, William T; Dewey, Ralph E

2015-01-01

211

Myopathy in cattle induced by alkaloid extracts from Thermopsis montanta, Laburnum anagyroides and a Lupinus sp.  

PubMed

A purified alkaloid preparation containing N-methylcytisine, cytisine, 5,6-dehydrolupanine, thermopsine and anagyrine from Thermopsis montana induced prolonged recumbency and microscopic acute hyaline skeletal myodegeneration with myofibre regeneration in cattle similar in type and severity to that induced by Thermopsis montanta plant material. This indicates that the alkaloid(s) of Thermopsis montana are responsible for the myopathy caused by the plant. An alkaloid preparation containing mostly anagyrine from a Lupinus sp. and an alkaloid preparation containing only cytisine from Laburnum anagyroides each caused microscopic skeletal muscle degeneration and necrosis similar to, but less severe than, the alkaloid extract from T. montana, but without clinical recumbency. Dosage and severity of response suggest that neither of those two alkaloids alone can account for the effects induced by Thermopsis. The data suggest that quinolizidine alkaloids with a alpha-pyridone A-ring may be responsible for the lesions and that individual alpha-pyridones may have additive effects. PMID:2246392

Keeler, R F; Baker, D C

1990-08-01

212

Miyoshianines A and B, two new lycopodium alkaloids from Huperzia miyoshiana.  

PubMed

Two new Lycopodium alkaloids, miyoshianines A and B, together with five known alkaloids, lycopodine, lycodoline, 12-epilycodoline, clavolonine, and flabelliformine, were isolated from Huperzia miyoshiana (Makino) Ching (Huperziaceae). Their structures were determined by means of spectroscopic techniques. PMID:12865986

Tong, Xiao-Tian; Tan, Chang-Heng; Ma, Xiao-Qiang; Wang, Bao-De; Jiang, Shan-Hao; Zhu, Da-Yuan

2003-06-01

213

Pyrrolizidine alkaloids in Senecio madagascariensis from Australia and Hawaii and assessment of possible livestock poisoning  

Technology Transfer Automated Retrieval System (TEKTRAN)

The alkaloid content of Senecio madagascariensis collected from Australia, and from Hawaii, was examined. Alkaloids were identified by GC-MS analysis and included: senecivernine, senecionine, integerrimine, senkirkine, mucronatinine, retrorsine, usaramine, otosenine, acetylsenkirkine, desacetyldoro...

214

Total synthesis of Galbulimima alkaloids. Resin-bound glycosyl phosphates as glycosyl donors.  

E-print Network

I. Total Synthesis of Galbulimima Alkaloids. The total synthesis of enantiomerically enriched (+)- and (-)-galbulimima alkaloid 13 is outlined. Sequential use of catalytic cross-coupling and cross-metathesis reactions ...

Hunt, Diana Katharine

2006-01-01

215

Nature's approach toward ring formation and structural diversity in ergot alkaloid biosynthesis  

E-print Network

Ergot alkaloids are fungal-derived secondary metabolites well known for a diverse array of pharmacological effects both beneficial and detrimental to human health. Historically, the ergot alkaloids have been known to cause ...

Cheng, Johnathan Zandrew

2011-01-01

216

Pyrrolizidine alkaloids in honey and bee pollen.  

PubMed

A total of 3917 honey samples and 119 'bee pollen' samples (pollen collected by honeybees) were analysed for pyrrolizidine alkaloids (PAs). Some 0.05 M sulphuric acid was used for extraction followed by a clean-up step by means of solid-phase extraction. Separation and detection was achieved by target analysis using an LC-MS/MS system. PAs were found in 66% of the raw honeys (bulk honey not yet packaged in containers for sale in retail outlets) and in 94% of honeys available in supermarkets (retail honey). A total of 60% of the bee pollen samples were PA positive. The PA pattern was used to identify the potential origin of the PAs in honey, which was verified for the genus Echium by relative pollen analysis. The results give an estimate of the impact of PA-containing plants belonging to the genera Echium, Senecio and, to a certain extent, Eupatorium on PA levels in honey and can serve as a decision basis for beekeepers in order to find the most suitable location for the production of honey and bee pollen low in PAs. PMID:21360377

Dübecke, A; Beckh, G; Lüllmann, C

2011-03-01

217

Ornithine Decarboxylase, Polyamines, and Pyrrolizidine Alkaloids in Senecio and Crotalaria  

PubMed Central

When tested for ornithine and arginine decarboxylases, pyrrolizidine alkaloid-bearing Senecio riddellii, S. longilobus (Compositae), and Crotalaria retusa (Leguminosae) plants exhibited only ornithine decarboxylase activity. This contrasts with previous studies of four species of pyrrolizidine alkaloid-bearing Heliotropium (Boraginaceae) in which arginine decarboxylase activity was very high relative to that of ornithine decarboxylase. Unlike Heliotropium angiospermum and Heliotropium indicum, in which endogenous arginine was the only detectable precursor of putrescine channeled into pyrrolizidines, in the species studied here—using difluoromethylornithine and difluoromethylarginine as the enzyme inhibitors—endogenous ornithine was the main if not the only precursor of putrescine converted into the alkaloid aminoalcohol moiety. In S. riddellii and C. retusa at flowering, ornithine decarboxylase activity was present mainly in leaves, especially the young ones. However, other very young organs such as inflorescence and growing roots exhibited much lower or very low activities; the enzyme activity in stems was negligible. There was no correlation between the enzyme activity and polyamine or alkaloid content in either species. In both species only free polyamines were detected except for C. retusa roots and inflorescence—with relatively very high levels of these compounds—in which conjugated putrescine, spermidine, and spermine were also found; agmatine was not identified by HPLC in any plant organ except for C. retusa roots with rhizobial nodules. Organ- or age-dependent differences in the polyamine levels were small or insignificant. The highest alkaloid contents were found in young leaves and inflorescence. PMID:16665870

Birecka, Helena; Birecki, Mieczyslaw; Cohen, Eric J.; Bitonti, Alan J.; McCann, Peter P.

1988-01-01

218

6,7-diepicastanospermine, a tetrahydroxyindolizidine alkaloid inhibitor of amyloglucosidase  

SciTech Connect

A tetrahydroxyindolizidine alkaloid, 6,7-diepicastanospermine, was isolated from the seeds of Castanospermum australe by extraction with methanol and purified to homogeneity using ion-exchange, preparative thin-layer, and radial chromatography. A very low yield of a pyrrolidine alkaloid, N-(hydroxyethyl)-2-(hydroxymethyl)-3-hydroxypyrrolidine, was also obtained by analogous methods. The purity of both alkaloids was established by gas chromatography of their trimethylsilyl (TMS) derivatives as better than 99%. The molecular weight of each alkaloid was established as 189 and 161, respectively, by mass spectrometry, and the structure of each was deduced from their {sup 1}H and {sup 13}C NMR spectra. The structure of the pyrrolidine alkaloids which co-occur in C. australe. 6,7-Diepicastanospermine was found to be a moderately good inhibitor of the fungal {alpha}-glucosidase, amyloglucosidase and a relatively weak inhibitor of {beta}-glucosidase. It failed to inhibit {alpha}-glucosidase. It failed to inhibit {alpha}- or {beta}-galactosidase, {alpha}- or {beta}-mannosidase, or {alpha}-L-fucosidase. Comparison of its inhibitory activity toward amyloglucosidase with those of its isomers, castanospermine and 6-epicastanospermine, demonstrated that epimerization of a single hydroxyl group can produce significant alteration of such inhibitory properties.

Molyneux, R.J.; Benson, M. (Dept. of Agriculture, Albany, CA (United States)); Pan, Y.T.; Tropea, J.E.; Kaushal, G.P.; Elbein, A.D. (Univ. of Texas, San Antonio (United States))

1991-10-15

219

Post-genome research on the biosynthesis of ergot alkaloids.  

PubMed

Genome sequencing provides new opportunities and challenges for identifying genes for the biosynthesis of secondary metabolites. A putative biosynthetic gene cluster of fumigaclavine C, an ergot alkaloid of the clavine type, was identified in the genome sequence of ASPERGILLUS FUMIGATUS by a bioinformatic approach. This cluster spans 22 kb of genomic DNA and comprises at least 11 open reading frames (ORFs). Seven of them are orthologous to genes from the biosynthetic gene cluster of ergot alkaloids in CLAVICEPS PURPUREA. Experimental evidence of the identified cluster was provided by heterologous expression and biochemical characterization of two ORFs, FgaPT1 and FgaPT2, in the cluster of A. FUMIGATUS, which show remarkable similarities to dimethylallyltryptophan synthase from C. PURPUREA and function as prenyltransferases. FgaPT2 converts L-tryptophan to dimethylallyltryptophan and thereby catalyzes the first step of ergot alkaloid biosynthesis, whilst FgaPT1 catalyzes the last step of the fumigaclavine C biosynthesis, i. e., the prenylation of fumigaclavine A at C-2 position of the indole nucleus. In addition to information obtained from the gene cluster of ergot alkaloids from C. PURPUREA, the identification of the biosynthetic gene cluster of fumigaclavine C in A. FUMIGATUS opens an alternative way to study the biosynthesis of ergot alkaloids in fungi. PMID:16902860

Li, Shu-Ming; Unsöld, Inge A

2006-10-01

220

Claviceps nigricans and Claviceps grohii: their alkaloids and phylogenetic placement.  

PubMed

Claviceps purpurea, C. grohii, C. zizaniae, C. cyperi, and C. nigricans are closely related ergot fungi and form a monophyletic clade inside the genus Claviceps. Analysis of alkaloid content in C. nigricans sclerotia using UPLC detected ergocristine (1), ergosine (2), alpha-ergocryptine (3), and ergocristam (4). Alkaloids 1, 3, and 4 were found in the sclerotia of C. grohii. The content of 4 in the mixture of alkaloids from C. nigricans and C. grohii (over 8% and over 20%, respectively) was unusually high. Submerged shaken cultures of C. nigricans produced no alkaloids, whereas C. grohii culture formed small amounts (15 mg L (-1)) of extracellular clavines and 1. In the previously used HPLC method the ergocristam degradation product could have been obscured by the ergosine peak. Therefore sclerotia of a C. purpurea habitat-specific population G2 with the dominant production of 1 and 2 have been reanalyzed, but no 4 was detected. The phylogeny of the C. purpurea-related species group is discussed with regard to alkaloid-specific nonribosomal peptide synthetase duplication leading to the production of two main ergopeptines instead of a single product. PMID:18461998

Pazoutová, Sylvie; Olsovská, Jana; Sulc, Miroslav; Chudícková, Milada; Flieger, Miroslav

2008-06-01

221

Geographic distribution of three alkaloid chemotypes of Croton lechleri.  

PubMed

Three known alkaloids, isoboldine (2), norisoboldine (1), and magnoflorine (8), have been isolated for the first time from Croton lechleri, a source of the wound healing latex "sangre de grado". An HPLC system was developed, and a large number of latex and leaf samples of C. lechleri from 22 sites in northern Peru and Ecuador were analyzed to gain an understanding of the natural variation in alkaloid content for the species. Up to six alkaloids were found to occur in the leaves including, in addition to those listed above, thaliporphine (3), glaucine (4), and taspine (9), whereas the latex contained only 9. Taspine (9) is the component that has been previously found to be responsible for the wound healing activity of C. lechleri latex, and its mean concentration throughout the range examined was found to be 9% of the latex by dry weight. In addition, three chemotypes are defined based on the alkaloid content of the leaves, and the geographic distribution of these chemotypes is discussed along with a quantitative analysis of the alkaloid content as a function of chemotype. PMID:12088421

Milanowski, Dennis J; Winter, Rudolph E K; Elvin-Lewis, Memory P F; Lewis, Walter H

2002-06-01

222

[Kinetic analysis of interaction of human immunodeficiency virus reverse transcriptase with alkaloids].  

PubMed

The interactions of HIV-I reverse transcriptase with some alkaloids were studied. Among nine compounds tested three--berberine, palmatine and sanguiritrine--inhibited RT. The dependence of the inhibition on the type of template-primer was also demonstrated. The kinetic analysis as well as circular dichroism experiments suggest the complex mechanism of RT inhibition by alkaloids. This mechanism includes both enzyme-alkaloid and alkaloid-template interactions; the latter effect also results in RT inhibition. PMID:7533889

Gudima, S O; Memelova, L V; Borodulin, V B; Pokholok, D K; Mednikov, B M; Tolkachev, O N; Kochetkov, S N

1994-01-01

223

Alkaloid Profiles, Concentration and Pools in Velvet Lupine (Lupinus leucophyllus) Over the Growing Season  

Technology Transfer Automated Retrieval System (TEKTRAN)

Lupinus leucophyllus is one of many lupine species known to contain toxic and/or teratogenic alkaloids that can cause congenital birth defects. The concentrations of total alkaloids and the individual major alkaloids were measured in three different years from different plant parts over the phenolog...

224

Overexpression of tropinone reductases alters alkaloid composition in Atropa belladonna root cultures  

Microsoft Academic Search

The medicinally applied tropane alkaloids hyoscy- amine and scopolamine are produced in Atropa bella- donna L. and in a small number of other Solanaceae. Calystegines are nortropane alkaloids that derive from a branching point in the tropane alkaloid biosynthetic pathway. In A. belladonna root cultures, calystegine molar concentration is 2-fold higher than that of hyo- scyamine and scopolamine. In this

Ute Richter; Grit Rothe; Anne-Katrin Fabian; Bettina Rahfeld; Birgit Drager

2005-01-01

225

An efficient synthesis of loline alkaloids Mesut Cakmak, Peter Mayer and Dirk Trauner*  

E-print Network

An efficient synthesis of loline alkaloids Mesut Cakmak, Peter Mayer and Dirk Trauner* Loline (1) is a small alkaloid that, in spite of its simple-looking structure, has posed surprising challenges alkaloid family. It delivers sufficient material to support a programme aimed at studying the complex

Trauner, Dirk

226

Ammonia chemical ionization tandem mass spectrometry in structural determination of alkaloids.  

E-print Network

Ammonia chemical ionization tandem mass spectrometry in structural determination of alkaloids. II 7 June 2001 Chemical ionization tandem mass spectrometry (CI-MS/MS) of alkaloids with ammonia alkaloids in extracts from six pseudomyrmecine ants of the genus Tetraponera. The MS/MS techniques along

227

Batrachotoxin alkaloids from passerine birds: A second toxic bird genus (Ifrita kowaldi)  

E-print Network

Batrachotoxin alkaloids from passerine birds: A second toxic bird genus (Ifrita kowaldi) from New as a species of a second toxic bird genus, Ifrita kowaldi. The alkaloids, identified in feathers and skin, were alkaloids, collectively called batrachotoxins, that stabilize the open form of voltage-gated sodium channels

228

Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-Desmethyl  

E-print Network

Asymmetric Total Synthesis of Dendrobatid Alkaloids: Preparation of Indolizidine 251F and Its 3-mail: jaube@ku.edu Abstract: Total syntheses of alkaloid 251F (1), a natural product detected from the skin array of natural product targets, particularly alkaloids, unprecedented in other biological systems.1

Taber, Douglass

229

The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids, the communesins, and nomofungin  

E-print Network

The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids Available online 11 April 2006 Abstract--A comparison is made between the calycanthaceous alkaloids for the communesins is presented that involves coupling of tryptamine with the ergot alkaloid aurantioclavine

Stoltz, Brian M.

230

The aqueous extract and the alkaloid fraction prepared from the leaves of Crassocephalum baucheiense  

E-print Network

The aqueous extract and the alkaloid fraction prepared from the leaves of Crassocephalum;2 Abbreviations AE, aqueous extract; AF, alkaloid fraction; Fr, fraction; ID50, dose of extract necessary and the alkaloid fraction prepared from the leaves of Crassocephalum baucheiense. Materials and methods: Using

Paris-Sud XI, Université de

231

Total Synthesis and Biological Evaluation of Amaryllidaceae Alkaloids: Narciclasine, ent-7-Deoxypancratistatin, Regioisomer of  

E-print Network

Total Synthesis and Biological Evaluation of Amaryllidaceae Alkaloids: Narciclasine, ent-7 approaches have yielded efficient total syntheses of the major Amaryllidaceae alkaloids, all based on the key remedies; the ancient Greeks knew their medicinal value.2 The alkaloids from their extracts have been

Hudlicky, Tomas

232

Synthetic studies toward the zoanthamine alkaloids: synthesis of the fully functionalized BC ring motif  

E-print Network

Synthetic studies toward the zoanthamine alkaloids: synthesis of the fully functionalized BC ring, collectively referred to as zoanthamine alkaloids.1 These natural products are distinguished by a densely the development of several synthetic routes toward the zoanthamine alkaloids7,8 that have recently culminated

Theodorakis, Emmanuel

233

Melyrid beetles (Choresine): A putative source for the batrachotoxin alkaloids found in poison-dart frogs  

E-print Network

Melyrid beetles (Choresine): A putative source for the batrachotoxin alkaloids found in poison by John W. Daly, September 28, 2004 Batrachotoxins are neurotoxic steroidal alkaloids first isolated from for these unique steroidal alkaloids was derived from the Greek ``batrachos,'' meaning frog. During the following

234

Regiocontrolled synthesis of the macrocyclic polyamine alkaloid ()-lunarine, a time-dependent inhibitor of trypanothione reductase  

E-print Network

Regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine, a time April 2002 A regiocontrolled synthesis of the macrocyclic polyamine alkaloid (±)-lunarine is described such study the macrocyclic polyamine alkaloid lunarine 1 was predicted to be a potential lead inhibitor (Fig

Schnaufer, Achim

235

BIOTRANSFORMATIONS OF MORPHINE ALKALOIDS BY FUNGI: N-DEMETHYLATIONS, OXIDATIONS, AND REDUCTIONS  

E-print Network

BIOTRANSFORMATIONS OF MORPHINE ALKALOIDS BY FUNGI: N-DEMETHYLATIONS, OXIDATIONS, AND REDUCTIONS on the occasion of his 85th birthday. Morphine alkaloids and some of its derivatives (morphine, codeine, thebaine. The alkaloids were transformed to a variety of products via biological oxidations, reductions, and oxidative

Hudlicky, Tomas

236

The alkaloidal responses of wild tobacco to real and simulated herbivory  

Microsoft Academic Search

I compared the induced alkaloidal response in undamaged leaves of plants subjected to herbivory by the larvae of Manduca sexta and to different simulations of this herbivory; all herbivory treatments removed similar amounts of leaf mass. Although larval feeding induced a significant increase (2.2x) in alkaloid concentrations compared to undamaged plants, the alkaloid responses to larval feeding were significantly lower

Ian T. Baldwin

1988-01-01

237

Intramolecular Hetero DielsAlder Routes to g-Carboline Alkaloids  

E-print Network

Intramolecular Hetero Diels±Alder Routes to g-Carboline Alkaloids Scott A. Snyder, David A. Vosburg alkaloids isocanthine (3), isocanthin-6-one (4), 1-methylisocanthine (5), and 1-methylisocanthin-6-one (6. Introduction Canthines are tetracyclic b-carboline alkaloids (general structure 1), several dozen of which have

Snyder, Scott A.

238

(Received, August 2004; Accepted, November 2004) ANTI-MICROBIAL ACTIVITY OF THE ALKALOID EXTRACT OF Genista  

E-print Network

109 (Received, August 2004; Accepted, November 2004) ANTI-MICROBIAL ACTIVITY OF THE ALKALOID, afforded two alkaloids, identified as lupanine (2-oxosparteine) 1 and S-calycotomine 2. The complete 1 H spectroscopy (COSY, DEPT, HMQC, HMBC).The alkaloid extract of Genista microcephala was tested against bacteria

Paré, Paul W.

239

Genetic variation of piperidine alkaloids in Pinus ponderosa: a common garden study  

Microsoft Academic Search

†Background and Aims Previous measurements of conifer alkaloids have revealed significant variation attribu- table to many sources, environmental and genetic. The present study takes a complementary and intensive, common garden approach to examine genetic variation in Pinus ponderosa var. ponderosa alkaloid production. Additionally, this study investigates the potential trade-off between seedling growth and alkaloid production, and associations between topographic\\/climatic variables

Elizabeth A. Gerson; Rick G. Kelsey; J. Bradley St Clair

2008-01-01

240

In vitro production of alkaloids: Factors, approaches, challenges and prospects  

PubMed Central

The wide diversity of plant secondary metabolites is largely used for the production of various pharmaceutical compounds. In vitro cell tissue or organ culture has been employed as a possible alternative to produce such industrial compounds. Tissue culture techniques provide continuous, reliable, and renewable source of valuable plant pharmaceuticals and might be used for the large-scale culture of the plant cells from which these secondary metabolites can be extracted. Alkaloids are one of the most important secondary metabolites known to play a vital role in various pharmaceutical applications leading to an increased commercial importance in recent years. The tissue culture techniques may be utilized to improve their production of alkaloids via somaclonal variations and genetic transformations. The focus of this review is toward the application of different tissue culture methods/techniques employed for the in vitro production of alkaloids with a systematic approach to improve their production. PMID:23922453

Ahmad, Sayeed; Garg, Madhukar; Tamboli, Ennus Tajuddin; Abdin, M. Z.; Ansari, S. H.

2013-01-01

241

Manzamine alkaloids: isolation, cytotoxicity, antimalarial activity and SAR studies.  

PubMed

The infectious disease Malaria is caused by different species of the genus Plasmodium. Resistance to quinoline antimalarial drugs and decreased susceptibility to artemisinin-based combination therapy have increased the need for novel antimalarial agents. Historically, natural products have been used for the treatment of infectious diseases. Identification of natural products and their semi-synthetic derivatives with potent antimalarial activity is an important method for developing novel antimalarial agents. Manzamine alkaloids are a unique group of ?-carboline alkaloids isolated from various species of marine sponge displaying potent antimalarial activity against drug-sensitive and -resistant strains of Plasmodium. In this review, we demonstrate antimalarial potency, cytotoxicity and antimalarial SAR of manzamine alkaloids. PMID:24953707

Ashok, Penta; Ganguly, Swastika; Murugesan, Sankaranarayanan

2014-11-01

242

Ecological context influences pollinator deterrence by alkaloids in floral nectar.  

PubMed

Secondary compounds may benefit plants by deterring herbivores, but the presence of these defensive chemicals in floral nectar may also deter beneficial pollinators. This trade-off between sexual reproduction and defense has received minimal study. We determined whether the pollinator-deterring effects of a nectar alkaloid found in the perennial vine Gelsemium sempervirens depend on ecological context (i.e. the availability of alternative nectar sources) by monitoring the behavioural response of captive bumblebees (Bombus impatiens, an important pollinator of G. sempervirens in nature) to nectar alkaloids in several ecologically relevant scenarios. Although alkaloids in floral nectar tended to deter visitation by bumblebees, the magnitude of that effect depended greatly on the availability and nectar properties of alternative flowers. Ecological context should thus be considered when assessing ecological costs of plant defense in terms of pollination services. We consider adaptive strategies that would enable plants to minimize pollinator deterrence because of defensive compounds in flowers. PMID:17498136

Gegear, Robert J; Manson, Jessamyn S; Thomson, James D

2007-05-01

243

Hydrofocusing Bioreactor Produces Anti-Cancer Alkaloids  

NASA Technical Reports Server (NTRS)

A methodology for growing three-dimensional plant tissue models in a hydrodynamic focusing bioreactor (HFB) has been developed. The methodology is expected to be widely applicable, both on Earth and in outer space, as a means of growing plant cells and aggregates thereof under controlled conditions for diverse purposes, including research on effects of gravitation and other environmental factors upon plant growth and utilization of plant tissue cultures to produce drugs in quantities greater and at costs lower than those of conventional methodologies. The HFB was described in Hydro focus - ing Bioreactor for Three-Dimensional Cell Culture (MSC-22358), NASA Tech Briefs, Vol. 27, No. 3 (March 2003), page 66. To recapitulate: The HFB offers a unique hydrofocusing capability that enables the creation of a low-shear liquid culture environment simultaneously with the herding of suspended cells and tissue assemblies and removal of unwanted air bubbles. The HFB includes a rotating cell-culture vessel with a centrally located sampling port and an internal rotating viscous spinner attached to a rotating base. The vessel and viscous spinner can be made to rotate at the same speed and direction or different speeds and directions to tailor the flow field and the associated hydrodynamic forces in the vessel in order to obtain low-shear suspension of cells and control of the locations of cells and air bubbles. For research and pharmaceutical-production applications, the HFB offers two major benefits: low shear stress, which promotes the assembly of cells into tissue-like three-dimensional constructs; and randomization of gravitational vectors relative to cells, which affects production of medicinal compounds. Presumably, apposition of plant cells in the absence of shear forces promotes cell-cell contacts, cell aggregation, and cell differentiation. Only gentle mixing is necessary for distributing nutrients and oxygen. It has been postulated that inasmuch as cells in the simulated microgravitation of an HFB do not need to maintain the same surface forces as in normal Earth gravitation, they can divert more energy sources to growth and differentiation and, perhaps, to biosynthesis of greater quantities of desired medicinal compounds. Because one can adjust the HFB to vary effective gravitation, one can also test the effects of intermediate levels of gravitation on biosynthesis of various products. The potential utility of this methodology for producing drugs was demonstrated in experiments in which sandalwood and Madagascar periwinkle cells were grown in an HFB. The conditions in the HFB were chosen to induce the cells to form into aggregate cultures that produced anti-cancer indole alkaloids in amounts greater than do comparable numbers of cells of the same species cultured according to previously known methodologies. The observations made in these experiments were interpreted as suggesting that the aggregation of the cells might be responsible for the enhancement of production of alkaloids.

Gonda, Steve R.; Valluri, Jagan V.

2011-01-01

244

Two new alkaloids from the bulbs of Lycoris sprengeri.  

PubMed

Two new alkaloids, lycosprenine (1) and 2?-methoxy-6-O-methyllycorenine (2), along with 22 known alkaloids (3-23b), were isolated from the bulb of Lycoris sprengeri. Their structures were elucidated on the basis of spectral analysis and by comparison of the spectroscopic data with those of known compounds. Selected compounds (1-3 and 6-9) were tested for their neuroprotective activities against H2O2-, CoCl2- and A?25-35-induced SH-SY5Y cell injury, most of which exhibited neuroprotective effects of different degrees. PMID:24313231

Wu, Wen-Ming; Zhu, Yun-Yun; Li, Hao-Ran; Yu, Heng-Yi; Zhang, Peng; Pi, Hui-Fang; Ruan, Han-Li

2014-01-01

245

Alkaloid-derived molecules in low rank Argonne premium coals.  

SciTech Connect

Molecules that are probably derived from alkaloids have been found in the extracts of the subbituminous and lignite Argonne Premium Coals. High resolution mass spectrometry (HRMS) and liquid chromatography mass spectrometry (LCMS) have been used to characterize pyridine and supercritical extracts. The supercritical extraction used an approach that has been successful for extracting alkaloids from natural products. The first indication that there might be these natural products in coals was the large number of molecules found containing multiple nitrogen and oxygen heteroatoms. These molecules are much less abundant in bituminous coals and absent in the higher rank coals.

Winans, R. E.; Tomczyk, N. A.; Hunt, J. E.

2000-11-30

246

Recent Advances in the Synthesis of Morphine and Related Alkaloids  

NASA Astrophysics Data System (ADS)

Morphine, an alkaloid isolated from the opium poppy, has been widely used as an analgesic, and has been a fascinating synthetic target of organic chemists. After the first total synthesis reported in 1952, a number of synthetic studies toward morphine have been reported, and findings obtained in such studies have greatly contributed to the progress of synthetic organic chemistry as well as medicinal chemistry. This review provides an overview of recent studies toward the total synthesis of morphine and related alkaloids. Work reported in the literature since 2004 will be reviewed.

Chida, Noritaka

247

Three new diterpenoid alkaloids from the roots of Aconitum duclouxii.  

PubMed

Three new C??-diterpenoid alkaloids, ducloudines C (1), D (2), and E (3), were isolated from the roots of Aconitum duclouxii. Their structures were established on the basis of extensive spectroscopic analyses. Ducloudine C (1) is the first aconitine-type C??-diterpenoid alkaloid with a C=O group at C-3 and a C=C bond between C-1 and C-2. All compounds were tested for their biological activities against one pathogenic fungi and two pathogenic bacteria. PMID:24498916

Yin, Tian-Peng; Cai, Le; He, Jian-Min; Dong, Jian-Wei; Fang, Hai-Xian; Zhou, Hao; Ding, Zhong-Tao

2014-01-01

248

Alkaloids isolated from the lateral root of Aconitum carmichaelii.  

PubMed

Two new alkaloids, aconicarmine (1) and aconicaramide (5), were isolated from the EtOH extract of the lateral roots of Aconitum carmichaelii, together with five known compounds: fuziline (2), neoline (3), N-ethylhokbusine B (4), 5-hydroxymethylpyrrole-2-carbaldehyde (6), and oleracein E (7). Their structures were elucidated by physical and NMR analysis. Pyrrole alkaloids were isolated from A. carmichaelii for the first time. In the in vitro assays, compounds 2 and 3 showed activity against pentobarbital sodiuminduced cardiomyocytes damage by obviously recovering beating rhythm and increasing the cell viability, while compounds 5 and 7 showed moderate antibacterial activity. PMID:22907155

Xiong, Liang; Peng, Cheng; Xie, Xiao-Fang; Guo, Li; He, Cheng-Jun; Geng, Zhao; Wan, Feng; Dai, Ou; Zhou, Qin-Mei

2012-01-01

249

Structural Analogs of Tylophora Alkaloids may not be Functional Analogs  

PubMed Central

Phenanthroindolizidine-based tylophora alkaloids have been reported to have potential antitumor, anti-immuno and anti-inflammatory activity. The structure-activity relationships of a series of tylophora alkaloids were studied to guide future drug design. Our results indicate that although these compounds are structural analogs, their potency of cytotoxicity, selectivity against NF-?B signaling pathway, and their inhibitory effects against protein and nucleic acid synthesis are different. Because they do not have an identical spectrum of targets, the studied compounds are structural, but may not be functional analogs. PMID:18077159

Gao, Wenli; Chen, Annie Pei-Chun; Leung, Chung-Hang; Gullen, Elizabeth A.; Fürstner, Alois; Shi, Qian; Wei, Linyi; Lee, Kuo-Hsiung; Cheng, Yung-Chi

2009-01-01

250

Spectrophotometric determination of Rauwolfia alkaloids: estimation of reserpine in pharmaceuticals.  

PubMed

A simple, sensitive and economically viable spectrophotometric method for the determination of some Rauwolfia alkaloids (ajmaline, ajmalicine, reserpine and yohimbine-HCl) has been developed. The method involves the oxidation of Rauwolfia alkaloids by iron(III) and subsequent complexation of iron(II) with 1,10-phenanthroline, forming a red-colored complex having the maximum absorbance at 510 nm. The method is applied to the determination of reserpine in tablets of pharmaceutical formulations. The common excipients do not interfere with the proposed method. A statistical comparison of these results with those of a reported method shows good agreement and indicates no significant difference in the precision. PMID:15068309

Singh, Dhruv K; Srivastava, Bhavana; Sahu, Archana

2004-03-01

251

Indole alkaloids and other constituents of Rauwolfia serpentina.  

PubMed

From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, N(b)-methylajmaline (1), N(b)-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed. PMID:15974606

Itoh, Atsuko; Kumashiro, Tomoko; Yamaguchi, Machiko; Nagakura, Naotaka; Mizushina, Yoshiyuki; Nishi, Toyoyuki; Tanahashi, Takao

2005-06-01

252

Five new indole alkaloids from the leaves of Rauvolfia yunnanensis.  

PubMed

Five new indole alkaloids, rauvoloids A-E (1-5), together with two known ones, raucaffrinoline (6) and perakine (7) were isolated from the leaves of Rauvolfia yunnanensis. Their structures were elucidated by extensive spectroscopic methods. Structurally, rauvoloids A (1), B-C (2-3) and D (4) with unusual substitution patterns (no substitution, Cl and (1E)-3-oxo-butenyl, respectively) at C-20, are the first examples of perakine-type alkaloids with C18 and C22 skeletons. PMID:23707746

Geng, Chang-An; Liu, Xi-Kui

2013-09-01

253

Alkaloid studies. 8. Isolation and characterization of alkaloids of Tabernaemontana heyneana Wall and antifertility properties of coronaridine.  

PubMed

In this study, the roots of Tabernaemontana heyneana Wall were examined and the isolation and identification of additional indole alkaloids and some pharmacological properties of coronaridine are described. Extraction of the roots yielded the alkaloids coronaridine, voacangine, ibogamine, 19-oxocoronaridine, and the pseudoindoxyl of voacangine. An acqueous ethanolic extract of the roots was found to prevent fertilization of adult female rats when administered orally. After the residue of this extract was treated chromatographic fractionation on silica gel yielded the alkaloid coronaridine. When administered to adult female rats, orally, coronaridine hydrochloride at levels of 5 mg/kg/day or above prevented pregnancy. Voacangine, assayed by the same procedure, did not prevent pregnancies. Data indicated that coronaridine was weakly estrogenic. PMID:4714135

Meyer, W E; Coppola, J A; Goldman, L

1973-07-01

254

Our previous studies on G. dumetorum yielded several aporphine alkaloids that showed significant activity against Leishmania spp.  

E-print Network

Our previous studies on G. dumetorum yielded several aporphine alkaloids that showed significant conducted additional isolation efforts on the minor alkaloids of this species. A standard alkaloid on the identification of alkaloids 1±9 from G. dumetorum (Fig.1). All nine of these metabolites were tested against

Coley, Phyllis

255

Recent developments of chiral induction in the syntheses of biologically important alkaloids.  

PubMed

Alkaloids are interesting groups of natural products with important biological properties, but naturally available alkaloids are insufficient for biological studies. Therefore, the demand for higher amounts of alkaloids made research community to synthesize alkaloids by innovative techniques. The importance of asymmetric reactions for scientific community to obtain enantiomerically pure compounds with good yield and diastereomeric excess (de) or enantiomeric excess (ee) by different strategies of asymmetric induction is emphasized in this review. In addition, importance have been given to discuss on biologically important alkaloids, their skeleton synthesis, intermediates and total synthesis with different strategies mainly based on chiral auxiliaries, chiral reagents and chiral metal ligand based catalysts. PMID:23978134

Pyarasani, Radha D; John, Amalraj; Santos, Leonardo S

2013-01-01

256

Isolation and structure elucidation of a new indole alkaloid from Rauvolfia serpentina hairy root culture: the first naturally occurring alkaloid of the raumacline group.  

PubMed

A new monoterpenoid indole alkaloid, 10-hydroxy- N(alpha)-demethyl-19,20-dehydroraumacline ( 1), was isolated as a mixture of E- and Z-isomers from hairy root culture of Rauvolfia serpentina Benth. ex Kurz (Apocynaceae) and the structure was determined by 1D and 2D NMR analyses. The new indole alkaloid represents the first naturally occurring alkaloid of the raumacline group and its putative biosynthetical pathway is discussed. PMID:12058321

Sheludko, Yuri; Gerasimenko, Irina; Kolshorn, Heinz; Stöckigt, Joachim

2002-05-01

257

Systematic identification of alkaloids in Macleaya microcarpa fruits by liquid chromatography tandem mass spectrometry combined with the isoquinoline alkaloids biosynthetic pathway.  

PubMed

Alkaloids in Macleaya microcarpa were characterized systematically by combining liquid chromatography tandem mass spectrometry (LC-MS/MS) with the biosynthetic pathway of isoquinoline alkaloids. The mass spectral fragmentation behaviors of 16 references belonging to eight types of alkaloids that exist in the biosynthetic pathway of isoquinoline were investigated in detail. The benzyltetrahydroisoquinoline and aporphine alkaloids were distinguished by characteristic losses of the NHR1R2 (R1 and R2 represent the substituent groups of the nitrogen atom) radical and the fragment ions below m/z 200. Tetrahydroprotoberberine, N-methyltetrahydroberberine and protopine alkaloids were differentiated by the retro-Diels-Alder (RDA) reaction, ?-cleavage and the [M-H2O](+) and [M-CH4](+) ions. Discrimination of protoberberine, benzophenanthridine and dihydrobenzophenanthridine-type alkaloids can be realized through the characteristic [fragment ion-2H](+), [M-H2O](+), [M-CH4](+), [M+H-CH3CH2CH2OH](+) and [M+H-CH3COCH3](+) ions. Forty-one alkaloids, including one benzyltetrahydroisoquinoline, one aporphine, nine protopines, seven protoberberines, one tetrahydroprotoberberine, three N-methyltetrahydroprotoberberines, five benzophenanthridines and fourteen dihydrobenzophenanthridines, were separated and identified simultaneously. Thirty-three of these were reported for the first time in M. microcarpa. The benzyltetrahydroisoquinoline, aporphine, tetrahydroprotoberberine and N-methyltetrahydroprotoberberine-type alkaloids have not been reported previously in M. microcarpa. This method can be applied to the analysis of herbal medicines that possess the biosynthetic pathway of isoquinoline alkaloids. PMID:25462117

Qing, Zhi-Xing; Cheng, Pi; Liu, Xiu-Bin; Liu, Yi-Song; Zeng, Jian-Guo

2014-11-01

258

The development of new synthetic strategies and methodologies for complex alkaloid total synthesis : a concise synthesis of (+)-chimonanthine, (+)-WIN 64821, (-)-ditryptophenaline and related alkaloids  

E-print Network

I. The Development of a General Strategy Towards Dimeric Hexahydropyrroloindole Alkaloids. A Concise Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine and (-)Calycanthine. An efficient and convergent strategy for the ...

Schmidt, Michael Anthony, 1980-

2008-01-01

259

Histochemical Investigation and Kinds of Alkaloids in Leaves of Different Developmental Stages in Thymus quinquecostatus  

PubMed Central

Thymus quinquecostatus, with more medical value, is a kind of wild plants. In order to exploit and utilize this plant, we studied the species and locations of alkaloids in its leaves. In this paper, histochemical study of leaves at different developing stages was taken to localize the alkaloids. Meanwhile, the kinds and content of alkaloids in leaves were identified using GC-MS technique. It was found that there were two kinds of glandular trichomes, namely, peltate trichomes and capitate trichomes, on the surface of leaves, and their secretory cells could secrete alkaloids. Results showed that trichomes could secrete alkaloids as soon as the first pair of leaves formed, and there were altogether 18 kinds of alkaloids identified by GC-MS. Nearly all of these alkaloids of leaves at different developing stages were distinct from each other, except one, 3-methoxy-a-methyl-benzeneethanamine, persists at different developing stages with high concentration. PMID:25101324

Jing, Haiting; Liu, Jing; Liu, Hanzhu; Xin, Hua

2014-01-01

260

Pyrroloquinoline and pyridoacridine alkaloids from marine sources.  

PubMed

Marine organisms are a rich source for natural products. Pyrrolo[4,3, 2-de]quinolines and pyrido[4,3,2-mn]acridines are of major interest as metabolites in sponges and ascidians. Many of these compounds have generated interest both as challenging problems for structure elucidation and synthesis as well as for their cytotoxicities. The isolation, structure proof, biological activities, chemical properties and synthesis have attracted the attention of chemists, biologists and pharmacists. The principal structural feature of these alkaloids is the core of a planar iminoquinone moiety which can intercalate into DNA and cleave the DNA double helix or inhibit the action of topoisomerase II. Of the makaluvamines, makaluvamine F and A are the most cytotoxic to the HCT 116 cell line. The enhanced toxicity of the makaluvamines towards xrs-6 cells shows that all of the makaluvamines, except makaluvamine B, act like m-AMSA and etoposide in inhibiting topo iso merases via cleavable complex formation, or via the direct induction of DNA double-strand breaks. They are also amongst the most potent inhibitors of topoisomerase II. Both makaluvamine A and C can decrease tumor size in a solid human tumor model. Discorhabdin A and C in contrast are of high cytotoxicity, but they exhibit no inhibition of topoisomerase II. As representatives of the derivatives of pyrido[4,3,2-mn]acridine, cystodytins, kuanoniamines and diplamine are the most potent to inhibit HCT replication. Eilatin, as a 1,10-phenanthroline derivative, can form complexes with metal ions. It has been shown that these metal complexes can bind to DNA by intercalation. The new members of the pyrrolo[4,3,2-de]quinolines and pyrido[4,3, 2-mn]acridines, such as veiutamine, discorhabdin G, tsitsikammamines, epinartins, arnoamines as well as sagitol are reviewed. Some successful syntheses of pyrrolo[4,3,2-de]quinoline ring system and pyrido[4,3,2-mn]acridine ring system are also reviewed in this article. PMID:9873113

Ding, Q; Chichak, K; Lown, J W

1999-01-01

261

An immunosuppressive tryptophan-derived alkaloid from Lepidagathis cristata.  

PubMed

An immunosuppressive, tryptophan-derived alkaloid cristatin A (1), and two known compounds, cycloartenol and stigmasta-5,11(12)-diene-3 beta-ol, were isolated from the whole plant Lepidagathis cristata Willd. The structures of the isolates were established by interpretation of their spectral data. PMID:11738419

Ravikanth, V; Niranjan Reddy, V L; Ramesh, P; Prabhakar Rao, T; Diwan, P V; Khar, A; Venkateswarlu, Y

2001-12-01

262

Synthetic Studies toward Lapidilectine-type Kopsia Alkaloids  

PubMed Central

A rapid synthesis of the tetracyclic core of Kopsia indole alkaloids related to lapidilectine B, grandilodine C, and tenuisine A is reported. Key to the success of this route was an efficient and scalable Ugi four-component coupling to install all the necessary carbons found in the natural products. PMID:22214219

Schultz, Erica E.; Pujanauski, Brian G.; Sarpong, Richmond

2012-01-01

263

Initial Studies on Alkaloids from Lombok Medicinal Plants  

Microsoft Academic Search

Initial investigation of medicinal plants from Lombok has resulted in the collection of 100 plant species predicted to have antimicrobial, including antimalarial, properties according to local medicinal uses. These plants represent 49 families and 80 genera; 23% of the plants tested positively for alkaloids. Among the plants testing positive, five have been selected for further investigation involving structure elucidation and

Surya Hadi; John B. Bremner

2001-01-01

264

Complanadines C and D, new dimeric alkaloids from Lycopodium complanatum.  

PubMed

Two new dimeric Lycopodium alkaloids, complanadines C (1) and D (2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistry of 1 and 2 were elucidated on the basis of the spectral data. Complanadine D (2) enhanced mRNA expression for NGF. PMID:17046268

Ishiuchi, Kan'ichiro; Kubota, Takaaki; Mikami, Yuzuru; Obara, Yutaro; Nakahata, Norimichi; Kobayashi, Jun'ichi

2007-01-01

265

Complanadines C and D, new dimeric alkaloids from Lycopodium complanatum  

Microsoft Academic Search

Two new dimeric Lycopodium alkaloids, complanadines C (1) and D (2), have been isolated from the club moss Lycopodium complanatum, and the structures and relative stereochemistry of 1 and 2 were elucidated on the basis of the spectral data. Complanadine D (2) enhanced mRNA expression for NGF.

Kan’ichiro Ishiuchi; Takaaki Kubota; Yuzuru Mikami; Yutaro Obara; Norimichi Nakahata; Jun’ichi Kobayashi

2007-01-01

266

The cell and developmental biology of alkaloid biosynthesis  

Microsoft Academic Search

Plants produce unique natural products as a result of gene mutation and subsequent adaptation of metabolic pathways to create new secondary metabolites. However, their biosynthesis and accumulation remains remarkably under the control of the biotic and abiotic environments. Alkaloid biosynthesis, which requires the adaptation of cellular activities to perform specialized metabolism without compromising general homeostasis, is accomplished by restricting product

Vincenzo De Luca; Benoit St Pierre

2000-01-01

267

Australine, a pyrrolizidine alkaloid that inhibits amyloglucosidase and glycoprotein processing  

SciTech Connect

Australine is a polyhydroxylated pyrrolizidine alkaloid that was isolated from the seeds of the Australian tree Castanospermum australe and characterized by NMR and X-ray diffraction analysis. Since swainsonine and catanospermine are polyhydroxylated indolizidine alkaloids that inhibit specific glycosidases, the authors tested australine against a variety of exoglycosidases to determine whether it would inhibit any of these enzymes. This alkaloid proved to be a good inhibitor of the {alpha}-glucosidase amyloglucosidase (50% inhibition at 5.8 {mu}M), but it did not inhibit {beta}-glucosidase, {alpha}- or {beta}-mannosidase, or {alpha}- or {beta}-galactosidase. The inhibition of amyloglucosidase was of a competitive nature. Australine also inhibited the glycoprotein processing enzyme glucosidase I, but had only slight activity toward glucosidase II. When incubated with cultured cells, this alkaloid inhibited glycoprotein processing at the glucosidase I step and caused the accumulation of glycoproteins with Glc{sub 3}Man{sub 7-9}(GlcNAc){sub 2}-oligosaccharides.

Tropea, J.E.; Molyneux, R.J.; Kaushal, G.P.; Pan, Y.T.; Mitchell, M.; Elbein, A.D. (Univ. of Texas Health Science Center, San Antonio (USA))

1989-03-07

268

Biosynthesis of the defensive alkaloid cicindeloine in Stenus solutus beetles  

NASA Astrophysics Data System (ADS)

To protect themselves from predation and microorganismic infestation, rove beetles of the genus Stenus produce and store bioactive alkaloids like stenusine, 3-(2-methyl-1-butenyl)pyridine, and cicindeloine in their pygidial glands. The biosynthesis of stenusine and 3-(2-methyl-1-butenyl)pyridine was previously investigated in Stenus bimaculatus and Stenus similis, respectively. Both molecules follow the same biosynthetic pathway, where the N-heterocyclic ring is derived from l-lysine and the side chain from l-isoleucine. The different alkaloids are finally obtained by slight modifications of shared precursor molecules. The piperideine alkaloid cicindeloine occurs as a main compound additionally to ( E)-3-(2-methyl-1-butenyl)pyridine and traces of stenusine in the pygidial gland secretion of Stenus cicindeloides and Stenus solutus. Feeding of S. solutus beetles with [D,15N]-labeled amino acids followed by GC/MS analysis techniques showed that cicindeloine is synthesized via the identical pathway and precursor molecules as the other two defensive alkaloids.

Schierling, Andreas; Dettner, Konrad; Schmidt, Jürgen; Seifert, Karlheinz

2012-08-01

269

Phenanthropiperidine Alkaloids: Methodology Development, Synthesis and Biological Evaluation  

E-print Network

-effects of the only alkaloid within this class to enter clinical trials: tylocrebrine. The preparation of cyclic enaminones in high enantiomeric purity is made possible through a one-flask, two-step protocol that uses mild Boc-deprotection conditions to suppress...

Niphakis, Micah James

2010-04-08

270

Mechanism of damage-induced alkaloid production in wild tobacco  

Microsoft Academic Search

Greenhouse-grown tobacco plants of the speciesNicotiana sylvestris (Solanaceae) subjected to leaf damage show a fourfold increase in the alkaloid content of their undamaged leaves. This increase in nicotine and nornicotine concentrations begins 19 hr after the end of the damage regime, reaches a maximum at nine days, and wanes to control levels 14 days after the start of leaf damage.

Ian T. Baldwin

1989-01-01

271

Alkaloid and predation patterns in colorado lupine populations  

Microsoft Academic Search

Colorado populations of herbaceous perennial lupines show three distinct patterns of amounts, kinds, and individual variability of inflorescence alkaloids. These patterns, interpreted as alternative chemical defense strategies, can be related to the susceptibility of populations to attack by larvae of a small flower-feeding lycaenid butterfly, Glaucopsyche lygdamus.

Peter M. Dolinger; Paul R. Ehrlich; William L. Fitch; Dennis E. Breedlove

1973-01-01

272

The effects of Aconitum alkaloids on the central nervous system  

Microsoft Academic Search

Preparations of Aconitum roots are employed in Chinese and Japanese medicine for analgesic, antirheumatic and neurological indications. The recent surge in use of phytomedicine derived from traditional Chinese medicine as well as increasing concerns about possible toxic effects of these compounds have inspired a great deal of research into the mechanisms by which certain Aconitum alkaloids may act on the

Angela Ameri

1998-01-01

273

Diversification of Ergot Alkaloids in Natural and Modified Fungi  

PubMed Central

Several fungi in two different families––the Clavicipitaceae and the Trichocomaceae––produce different profiles of ergot alkaloids, many of which are important in agriculture and medicine. All ergot alkaloid producers share early steps before their pathways diverge to produce different end products. EasA, an oxidoreductase of the old yellow enzyme class, has alternate activities in different fungi resulting in branching of the pathway. Enzymes beyond the branch point differ among lineages. In the Clavicipitaceae, diversity is generated by the presence or absence and activities of lysergyl peptide synthetases, which interact to make lysergic acid amides and ergopeptines. The range of ergopeptines in a fungus may be controlled by the presence of multiple peptide synthetases as well as by the specificity of individual peptide synthetase domains. In the Trichocomaceae, diversity is generated by the presence or absence of the prenyl transferase encoded by easL (also called fgaPT1). Moreover, relaxed specificity of EasL appears to contribute to ergot alkaloid diversification. The profile of ergot alkaloids observed within a fungus also is affected by a delayed flux of intermediates through the pathway, which results in an accumulation of intermediates or early pathway byproducts to concentrations comparable to that of the pathway end product. PMID:25609183

Robinson, Sarah L.; Panaccione, Daniel G.

2015-01-01

274

EFFECT OF SHADE ON ALKALOID CONTENT OF LUPINUS LEUCOPHYLLUS  

Technology Transfer Automated Retrieval System (TEKTRAN)

Lupine-induced "crooked calf" syndrom is a significant problem for ranches in the semi-arid region of the channeled scablands of eastern Washington State. Rainfall and soil moisture has been proposed to affect the alkaloid content and/or palatability of L. leucophyllus. It is also possible that shad...

275

Management of three toxic Delphinium species based on alkaloid concentrations  

Microsoft Academic Search

A systematic approach to the taxonomic classification of the tall larkspur complex (Delphinium spp.) has been developed and implemented using molecular genetics, plant morphology, and alkaloid profiles, as shown in other papers in this series. This approach supports the classification of three distinct species (D. glaucum, D. barbeyi and D. occidentale), as the species differ in genetics and toxicity. Toxic

James A Pfister; Michael H Ralphs; Dale R Gardner; Bryan L Stegelmeier; Gary D Manners; Kip E Panter; Steven T Lee

2002-01-01

276

Pyrrolizidine alkaloids in food: A spectrum of potential health consequences  

Technology Transfer Automated Retrieval System (TEKTRAN)

Contamination of grain with 1,2-dehydropyrrolizidine ester alkaloids (dehydroPAs) and their N-oxides is responsible for large incidents of acute and subacute food poisoning, with high morbidity and mortality, in Africa and in central and south Asia. Herbal medicines and teas containing dehydroPAs ha...

277

Alkaloids as aldose reductase inhibitors, with special reference to berberine.  

PubMed

Aldose reductase is the rate-limiting enzyme of the polyol pathway that leads to conversion of glucose to sorbitol. Its increased activity, which results in abnormal activation of the polyol pathway, is implicated in the development of long-term complications of diabetes mellitus. Different plant species and their active components have shown potent in vitro and in vivo aldose reductase inhibitory activity. Among different phyto-constituents, alkaloids that contain isoquinoline/bis(isoquinoline)and related ring structures (such as berberine, palmatine, coptisine, and jateorrhizine) have shown very potent aldose reductase inhibitory activity. The structural activity relationship has revealed the importance of hydrophobic and hydrophilic groups of isoquinoline/bis(isoquinoline)for binding to an enzyme. The dioxymethylene group in the D ring (hydrophobic group) of these alkaloids binds tightly to the site adjacent to the anionic binding site (active site), while the methoxyl groups (polar) bind to the site adjacent to the nicotinamide ring of the coenzyme. On the basis of these findings, it may be proposed that the presence of isoquinoline/bis(isoquinoline)ring structures is the most important requirement for alkaloids to behave as potent aldose reductase inhibitors. Thus, other plants may also be screened for the same activity. The present review discusses these isoquinoline/bis(isoquinoline)-based alkaloids as aldose reductase inhibitors that may be used to manage diabetic complications and may substitute for the chemically synthesized aldose reductase inhibitors. PMID:24236461

Gupta, Sakshi; Singh, Nirmal; Jaggi, Amteshwar Singh

2014-03-01

278

Pyrrolizidine alkaloids of three species of senecio in British Columbia.  

PubMed

A new alkaloid, 9- O-acetyl-7- O-angelyl-retronecine, was isolated from Senecio triangularis together with 7-O-angelyl-, 9-O-angelyl-, and 7-O-angelyl-9-O-sarracinylretronecine; S. pseudaureus and S. streptanthifolios yielded only retrorsine and senecionine. PMID:17252412

Bai, Y; Benn, M; Majak, W

1996-02-01

279

Redox divergent synthesis of fawcettimine-type Lycopodium alkaloids.  

PubMed

A new approach for synthesis of fawcettimine-type Lycopodium alkaloids is described. A divergent strategy was achieved by applying stereoselective Diels-Alder reaction followed by redox-controlled elaboration. Eventually, (-)-8-deoxyserratinine, (+)-fawcettimine, (-)-lycopoclavamine-A, (-)-serratine, (-)-lycopoclavamine-B and (-)-serratanidine were successfully accessed. PMID:25042023

Zaimoku, Hisaaki; Taniguchi, Tsuyoshi

2014-07-28

280

Isolation of a new lycodine alkaloid from Lycopodium japonicum.  

PubMed

A new lycodine alkaloid, N-methylhydroxypropyllycodine (1), was isolated from the club moss Lycopodium japonicum Thunb, together with five known compounds, N-methyllycodine (2), huperzinine (3), ?-obscurine (4), ?-obscurine (5) and des-N-methyl-?-obscurine (6). Their structures were elucidated by spectroscopic analyses, including 2D NMR techniques. PMID:25421949

Wu, Jichun; Wang, Huanqin; Ma, Yanfang; Jiang, Jinhe; Zhan, Rui; Chen, Yegao

2014-11-25

281

Total syntheses of Lycopodium alkaloids (+)-fawcettimine, (+)-fawcettidine, and (-)-8-deoxyserratinine.  

PubMed

A shared story: Three fawcettimine- and serratinine-type Lycopodium alkaloids are prepared from a common tetracyclic spirodiketone intermediate in concise total syntheses. The intermediate was constructed by a remarkable biosynthesis-inspired transannular N-C bond formation to the spiro-configured carbon center and a hydroxy-directed pinacol coupling promoted by SmI(2). PMID:22109940

Li, Houhua; Wang, Xiaoming; Lei, Xiaoguang

2012-01-01

282

Alkaloid profiling and anticholinesterase activity of South American Lycopodiaceae species.  

PubMed

The alkaloid extracts of four Huperzia and one Lycopodiella species, from Brazilian habitats, were tested for their in vitro anticholinesterase activities. IC(50) values showed a potent acetylcholinesterase inhibition for H. reflexa (0.11?±?0.05 ?g/mL), followed by H. quadrifariata (2.0?±?0.3 ?g/mL), H. acerosa (5.5?±?0.9 ?g/mL), H. heterocarpon (25.6?±?2.7 ?g/mL) and L. cernua (42.6?±?1.5 ?g/mL). A lower inhibition of butyrylcholinesterase was observed for all species with the exception of H. heterocarpon (8.3?±?0.9 ?g/mL), whose alkaloid extract presented a selectivity for pseudocholinesterase. Moreover, the chemical study of the bioactive extracts performed by GC-MS, revealed the presence of a number of Lycopodium alkaloids belonging to the lycopodane, flabellidane and cernuane groups. Surprisingly, the potent acetylcholinesterase inhibitors huperzines A and B were not detected in the extracts, suggesting that other alkaloids may be responsible for such an effect. PMID:22117191

Konrath, Eduardo Luis; Ortega, María Gabriela; de Loreto Bordignon, Sérgio; Apel, Miriam Anders; Henriques, Amélia Teresinha; Cabrera, José Luis

2013-02-01

283

Biogenetically inspired total syntheses of Lycopodium alkaloids, (+)-flabellidine and (-)-lycodine.  

PubMed

The first asymmetric total synthesis of (+)-flabellidine (2) and the shortest total synthesis of (-)-lycodine (3) were accomplished by a strategy featuring the one-pot construction of a tetracyclic lycodine skeleton from a linear precursor, which was inspired by the biosynthetic consideration of Lycopodium alkaloids. PMID:25103992

Azuma, Masayuki; Yoshikawa, Tetsuya; Kogure, Noriyuki; Kitajima, Mariko; Takayama, Hiromitsu

2014-08-20

284

Effect of Ergot Alkaloids on Bovine Foregut Vasculature  

Technology Transfer Automated Retrieval System (TEKTRAN)

Ergot alkaloids induce vasoconstriction of bovine foregut vasculature. Ergovaline induced the greatest response in ruminal artery while ergovaline and ergotamine induced the greatest response in ruminal vein. Lysergic acid did not stimulate a contractile response in either the ruminal artery or vein...

285

Distribution, biosynthesis and turnover of pyrrolizidine alkaloids in Cynoglossum officinale  

Microsoft Academic Search

The facultative biennial Cynoglossum officinale contains the N-oxides of the following pyrrolizidine alkaloids (PAs): trachelanthamine, viridiflorine, 7-angeloylheliotridine, rinderine, echinatine, 3?-acetylechinatine and heliosupine. The inflorescences contain the highest levels of PAs. At the vegetative rosette stage, the youngest leaves have higher PA levels than the older leaves. Both isolated roots and isolated shoots of rosette plants were able to produce PAs

Nicole M. van Dam; Ludger Witte; Claudine Theuring; Thomas Hartmann

1995-01-01

286

Induced responses in three alkaloid-containing plant species  

Microsoft Academic Search

In this paper we test three plant species for the inducibility of their alkaloid production. The plants were heavily damaged by cutting off 50% of their leaf surface using a pair of scissors. The cut-off leaf tips were used as controls for possible diurnal fluctuations. After 3, 6, 12, 24 and 48 h, respectively, the leaf bases of the damaged

Nicole M. van Dam; Ed van der Meijden; Robert Verpoorte

1993-01-01

287

Indole alkaloids from Rauvolfia bahiensis A.DC. (Apocynaceae).  

PubMed

Four indole alkaloids, 12-methoxy-N(a)-methyl-vellosimine, demethoxypurpeline, 12-methoxyaffinisine, and 12-methoxy-vellosimine, in addition to picrinine, vinorine, raucaffrinoline, normacusine B, norseredamine, seredamine, 10-methoxynormacusine B, norpurpeline and purpeline, were isolated from the bark or leaf extracts of Rauvolfia bahiensis. PMID:12031452

Kato, Lucilia; Marques Braga, Raquel; Koch, Ingrid; Sumiko Kinoshita, Luiza

2002-06-01

288

Indole alkaloids of Rauwolfia reflexa. Carbon-13 nuclear magnetic resonance structural analysis of the bis(indole) alkaloid flexicorine  

SciTech Connect

The /sup 13/C NMR spectra analysis of the new bis(indole) alkaloid flexicorine and of its chemically modified derivatives were used to determine the structure of the natural base. Flexicorine is, apparently, the first 10'-hydroxy N'-unsubstituted indoline which preferentially exists in the original iminoquinone form. 2 tables.

Chatterjee, A. (Univ. College of Science, Calcutta, India); Ghosh, A.K.; Hagaman, E.W.

1982-01-01

289

Alkaloid profiling of crude and processed Veratrum nigrum L. through simultaneous determination of ten steroidal alkaloids by HPLC-ELSD.  

PubMed

Veratrum nigrum L., a traditional Chinese herb, has been used for treatment of hypertension, blood-stroke, excessive phlegm, epilepsy, etc. Steroidal alkaloids were well-known as both bioactive and toxic constituents of Veratrum species, the toxicity of which the traditional processing procedure can reduce. To reveal the mechanism of processing V. nigrum L., a high performance liquid chromatography (HPLC) with evaporative light scattering detector (ELSD) method was developed for the simultaneous determination of ten steroidal alkaloids in crude and processed V. nigrum L., comparison with ultrasound extract of crude V. nigrum L. With a Venusil XBP-C(18) analytical column, the analytes were separated efficiently using the mobile phase consisted of (A) 0.03% aqueous triethylamine (TEA) and (B) acetonitrile in a gradient program. The parameters for ELSD were set: S.C. (Spray Chamber)=35 degrees C, D.T. (Drift Tube)=70 degrees C, GAS=50 psi. All calibration curves showed good linear regression (gamma>or=0.9990) within the tested range. Additionally, reproducibility for the quantification of ten alkaloids in V. nigrum L. with intra- and inter-day variations of less than 5.0% was observed. The obtained alkaloid profiles performed by this newly established method, provided valuable information for the differentiation of crude and processed V. nigrum L. and for the explanation of the different toxicity. PMID:18599245

Cong, Yue; Zhou, Yu-Bo; Chen, Jing; Zeng, Yi-Mei; Wang, Jin-Hui

2008-11-01

290

Formicine ants: An arthropod source for the pumiliotoxin alkaloids of dendrobatid poison frogs  

PubMed Central

A remarkable diversity of bioactive lipophilic alkaloids is present in the skin of poison frogs and toads worldwide. Originally discovered in neotropical dendrobatid frogs, these alkaloids are now known from mantellid frogs of Madagascar, certain myobatrachid frogs of Australia, and certain bufonid toads of South America. Presumably serving as a passive chemical defense, these alkaloids appear to be sequestered from a variety of alkaloid-containing arthropods. The pumiliotoxins represent a major, widespread, group of alkaloids that are found in virtually all anurans that are chemically defended by the presence of lipophilic alkaloids. Identifying an arthropod source for these alkaloids has been a considerable challenge for chemical ecologists. However, an extensive collection of neotropical forest arthropods has now revealed a putative arthropod source of the pumiliotoxins. Here we report on the presence of pumiliotoxins in formicine ants of the genera Brachymyrmex and Paratrechina, as well as the presence of these ants in the stomach contents of the microsympatric pumiliotoxin-containing dendrobatid frog, Dendrobates pumilio. These pumiliotoxins are major alkaloids in D. pumilio, and Brachymyrmex and Paratrechina ants now represent the only known dietary sources of these toxic alkaloids. These findings further support the significance of ant-specialization and alkaloid sequestration in the evolution of bright warning coloration in poison frogs and toads. PMID:15128938

Saporito, Ralph A.; Garraffo, H. Martin; Donnelly, Maureen A.; Edwards, Adam L.; Longino, John T.; Daly, John W.

2004-01-01

291

Differential allocation of seed-borne ergot alkaloids during early ontogeny of morning glories (Convolvulaceae).  

PubMed

Ergot alkaloids are mycotoxins that can increase host plant resistance to above- and below-ground herbivores. Some morning glories (Convolvulaceae) are infected by clavicipitaceous fungi (Periglandula spp.) that produce high concentrations of ergot alkaloids in seeds-up to 1000-fold greater than endophyte-infected grasses. Here, we evaluated the diversity and distribution of alkaloids in seeds and seedlings and variation in alkaloid distribution among species. We treated half the plants with fungicide to differentiate seed-borne alkaloids from alkaloids produced de novo post-germination and sampled seedling tissues at the cotyledon and first-leaf stages. Seed-borne alkaloids in Ipomoea amnicola, I. argillicola, and I. hildebrandtii remained primarily in the cotyledons, whereas I. tricolor allocated lysergic acid amides to the roots while retaining clavines in the cotyledons. In I. hildebrandtii, almost all festuclavine was found in the cotyledons. These observations suggest differential allocation of individual alkaloids. Intraspecific patterns of alkaloid distribution did not vary between fungicide-treated and control seedlings. Each species contained four to six unique ergot alkaloids and two species had the ergopeptine ergobalansine. De novo production of alkaloids did not begin immediately, as total alkaloids in fungicide-treated and control seedlings did not differ through the first-leaf stage, except in I. argillicola. In an extended time-course experiment with I. tricolor, de novo production was detected after the first-leaf stage. Our results demonstrate that allocation of seed-borne ergot alkaloids varies among species and tissues but is not altered by fungicide treatment. This variation may reflect a response to selection for defense against natural enemies. PMID:23835852

Beaulieu, Wesley T; Panaccione, Daniel G; Hazekamp, Corey S; mckee, Michelle C; Ryan, Katy L; Clay, Keith

2013-07-01

292

Analysis of bioactive Amaryllidaceae alkaloid profiles in Lycoris species by GC-MS.  

PubMed

The genus Lycoris, a group of Amaryllidaceae plants distributed in temperate regions of Eastern Asia, is already known for containing representative alkaloids typical of this botanical family with a wide range of biological activities (for example, lycorine and galanthamine). In the present work, the alkaloid profiles of nine species, L. albiflora, L. aurea, L. chinensis, L. haywardii, L. incarnata, L. longituba, L. radiata, L. sprengeri, and L. squamigera, and one variety (L. radiata var. pumila) have been evaluated by GC-MS. Structures belonging to the lycorine-, homolycorine-, haemanthamine-, narciclasine-, tazettine-, montanine- and galanthamine-series were identified and quantified, with galanthamine- and lycorine-type alkaloids predominating and usually showing a high relative abundance in comparison with other alkaloids of the extracts. Interestingly, L. longituba revealed itself to be a potential commercial source of bioactive alkaloids. In general terms, our results are consistent with the alkaloid profiles reported in the literature for previously studied species. PMID:25233578

Guo, Ying; Pigni, Natalia B; Zheng, Yuhong; de Andrade, Jean Paulo; Torras-Claveria, Laura; Borges, Warley de Souza; Viladomat, Frances; Codina, Carles; Bastida, Jaume

2014-08-01

293

Parasitic fungus Claviceps as a source for biotechnological production of ergot alkaloids.  

PubMed

Ergot alkaloids produced by the fungus Claviceps parasitizing on cereals, include three major groups: clavine alkaloids, d-lysergic acid and its derivatives and ergopeptines. These alkaloids are important substances for the pharmatech industry, where they are used for production of anti-migraine drugs, uterotonics, prolactin inhibitors, anti-Parkinson agents, etc. Production of ergot alkaloids is based either on traditional field cultivation of ergot-infected rye or on submerged cultures of the fungus in industrial fermentation plants. In 2010, the total production of these alkaloids in the world was about 20,000 kg, of which field cultivation contributed about 50%. This review covers the recent advances in understanding of the genetics and regulation of biosynthesis of ergot alkaloids, focusing on possible applications of the new knowledge to improve the production yield. PMID:22261014

Hulvová, Helena; Galuszka, Petr; Frébortová, Jitka; Frébort, Ivo

2013-01-01

294

[Exploration of toxicity reducing mechanism of aconite alkaloids during decoction process using liquid chromatography-mass spectrometry].  

PubMed

A high performance liquid chromatography-electrospray ionization mass spectrometry method was developed for the determination of aconite alkaloids. It was used to investigate the degradation of alkaloids of Radix Aconiti Lateralis Preparata during decoction. Six alkaline degradation products were identified, and the degradation regularity of diester-diterpenoid alkaloids was confirmed during the test using standards. The dynamic changes of the amount of aconite alkaloids in the decoction of Radix Aconiti Lateralis Preparata were supervised. Along with the increase of decoction time, the concentrations of diester-diterpenoid alkaloids and lipo-alkaloid decreased significantly. The results can provide a scientific basis for the safety use of aconite. PMID:24558845

Chen, Ping; Chen, Yimin; Chen, Jia; Tong, Hongbin; Xu, Zhiliang

2013-11-01

295

Lophocladines, Bioactive Alkaloids from the Red Alga Lophocladia sp.  

PubMed Central

Lophocladines A (1) and B (2), two 2,7-naphthyridine alkaloids, were isolated from the marine red alga Lophocladia sp. collected in the Fijian Islands. Their structures were deduced on the basis of high-resolution mass spectra and one- and two-dimensional NMR spectroscopy. Lophocladine A (1) displayed affinity for NMDA receptors and was found to be a ?-opioid receptor antagonist, whereas lophocladine B (2) exhibited cytotoxicity to NCI-H460 human lung tumor and MDA-MB-435 breast cancer cell lines. Immunofluorescence studies indicated that the cytotoxicity of lophocladine B (2) was correlated with microtubule inhibition. This is the first reported occurrence of alkaloids based on a 2,7-naphthyridine skeleton from red algae. PMID:16643042

Gross, Harald; Goeger, Douglas E.; Hills, Patrice; Mooberry, Susan L.; Ballantine, David L.; Murray, Thomas F.; Valeriote, Frederick A.; Gerwick, William H.

2009-01-01

296

Biogenetically inspired synthesis and skeletal diversification of indole alkaloids  

NASA Astrophysics Data System (ADS)

To access architecturally complex natural products, chemists usually devise a customized synthetic strategy for constructing a single target skeleton. In contrast, biosynthetic assembly lines often employ divergent intramolecular cyclizations of a polyunsaturated common intermediate to produce diverse arrays of scaffolds. With the aim of integrating such biogenetic strategies, we show the development of an artificial divergent assembly line generating unprecedented numbers of scaffold variations of terpenoid indole alkaloids. This approach not only allows practical access to multipotent intermediates, but also enables systematic diversification of skeletal, stereochemical and functional group properties without structural simplification of naturally occurring alkaloids. Three distinct modes of [4+2] cyclizations and two types of redox-mediated annulations provided divergent access to five skeletally distinct scaffolds involving iboga-, aspidosperma-, andranginine- and ngouniensine-type skeletons and a non-natural variant within six to nine steps from tryptamine. The efficiency of our approach was demonstrated by successful total syntheses of (±)-vincadifformine, (±)-andranginine and (-)-catharanthine.

Mizoguchi, Haruki; Oikawa, Hideaki; Oguri, Hiroki

2014-01-01

297

Antimalarial benzylisoquinoline alkaloid from the rainforest tree Doryphora sassafras.  

PubMed

Mass-directed isolation of the CH(2)Cl(2)/MeOH extract of Doryphora sassafras resulted in the purification of a new benzylisoquinoline alkaloid, 1-(4-hydroxybenzyl)-6,7-methylenedioxy-2-methylisoquinolinium trifluoroacetate (1), and the known aporphine alkaloid (S)-isocorydine (2). The structures of 1 and 2 were determined by 1D and 2D NMR and MS data analyses. The compounds were isolated during a drug discovery program aimed at identifying new antimalarial leads from a prefractionated natural product library. When tested against two different strains of the parasite Plasmodium falciparum (3D7 and Dd2), 1 displayed IC(50) values of 3.0 and 4.4 microM, respectively. Compound 1 was tested for cytotoxicity toward a human embryonic kidney cell line (HEK293) and displayed no activity at 120 microM. PMID:19637893

Buchanan, Malcolm S; Davis, Rohan A; Duffy, Sandra; Avery, Vicky M; Quinn, Ronald J

2009-08-01

298

A Submarine Journey: The Pyrrole-Imidazole Alkaloids  

PubMed Central

In his most celebrated tale “The Picture of Dorian Gray”, Oscar Wilde stated that “those who go beneath the surface do so at their peril”. This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity – from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products. PMID:20098608

Forte, Barbara; Malgesini, Beatrice; Piutti, Claudia; Quartieri, Francesca; Scolaro, Alessandra; Papeo, Gianluca

2009-01-01

299

Various alkaloid profiles in decoctions of Banisteriopsis caapi.  

PubMed

Twenty nine decoctions of Banisteriopsis caapi from four different sources and one specimen of B. caapi paste were analyzed for N,N-dimethyltryptamine (DMT), tetrahydroharmine (THH), harmaline and harmine. Other plants were also used in the preparation of these products, typically Psychotria viridis, which provides DMT. There were considerable variations in alkaloid profiles, both within and between sample sources. DMT was not detected in all samples. Additional THH may be formed from both harmine and harmaline during the preparation of these products. The alkaloid composition of one decoction sample did not change significantly after standing at room temperature for 80 days, but the initial acidic pH was neutralized by natural fermentation after 50 days. PMID:16149328

Callaway, J C

2005-06-01

300

New dimeric aporphine alkaloids and cytotoxic constituents of Hernandia nymphaeifolia.  

PubMed

Three minor new dimeric aporphine alkaloids, oviisocorydine (1), ovihernangerine (2), and oxohernandaline (3), along with four known alkaloids, (+)-hernandaline, (+)-thallcarpine, (+)-N-methylovigerine, and N-methylcorydaldine, and five known lignans, (+)-epimagnolin, (+)-epiaschantin, (+)-epiyangambin, (-)-deoxypodophyllotoxin, and (-)-yatein, have been additionally isolated from the trunk bark of Hernandia nymphaeifolia. The structures of these compounds were elucidated by spectroscopic methods. Among forty-four isolates obtained till now, nine compounds, hernandonine (4), hernanymphine (5), demethylsonodione (6), (+)-ovigerine (7), (+)-N-methylovigerine (8), N-formyldehydroovigerine (9), 4-methoxyoxohernandaline (10), (-)-deoxypodophyllotoxin (11), and (-)-yatein (12) showed significant cytotoxic activities (ED50 values < 1 microgram/ml) against P-388, KB16, A549, and HT-29 cell lines. PMID:9000885

Chen, J J; Ishikawa, T; Duh, C Y; Tsai, I L; Chen, I S

1996-12-01

301

Short-term damage-induced increases in tobacco alkaloids protect plants  

Microsoft Academic Search

Leaf damage significantly increases the alkaloid content in undamaged leaves on damaged field-grown wild tobacco plants. Although field-grown pot-bound plants fail to exhibit the same damage-induced increase in alkaloid content, the ability to respond to leaf damage is restored 6 days after removing plants from their pots. Freshly hatched Manduca sexta larvae reared individually in the laboratory on the high-alkaloid

Ian T. Baldwin

1988-01-01

302

Sites of synthesis, translocation and accumulation of pyrrolizidine alkaloid N-oxides in Senecio vulgaris L  

Microsoft Academic Search

14C-Labelled alkaloid precursors (arginine, putrescine, spermidine) fed to Senecio vulgaris plants via the root system were rapidly taken up and efficiently incorporated into the pyrrolizidine alkaloid senecionine N-oxide (sen-Nox) with total incorporations of 3–6%. Considerable amounts of labelled sen-Nox were translocated into the shoot and were directed mainly into the inflorescences, the major sites of pyrrolizidine-alkaloid accumulation. Detached shoots of

Thomas Hartmann; Adelheid Ehmke; Udo Eilert; Kirsten Borstel; Claudine Theuring

1989-01-01

303

?-Carboline Alkaloids from Galianthe ramosa Inhibit Malate Synthase from Paracoccidioides spp.  

PubMed

As part of our continuing chemical and biological analyses of Rubiaceae species from Cerrado, we isolated novel alkaloids 1 and 2, along with known compounds epicatechin, ursolic acid, and oleanolic acid, from Galianthe ramosa. Alkaloid 2 inhibited malate synthase from the pathogenic fungus Paracoccidioides spp. This enzyme is considered an important molecular target because it is not found in humans. Molecular docking simulations were used to describe the interactions between the alkaloids and malate synthase. PMID:25412318

de Freitas, Carla S; Kato, Lucilia; de Oliveira, Cecília M A; Queiroz, Luiz H K; Santana, Mábio J; Schuquel, Ivânia T; Delprete, Piero G; da Silva, Roosevelt A; Quintino, Guilherme O; da Silva Neto, Benedito R; Soares, Célia M A; Pereira, Maristela

2014-12-01

304

Puberunine and puberudine, two new C18-diterpenoid alkaloids from Aconitum barbatum var. puberulum.  

PubMed

Two C(18)-diterpenoid alkaloids, puberunine (1) and puberudine (2), together with four other new alkaloids, including the first examples having ?-oriented substitution at C-3 and a rare chloro-substituent were isolated from Aconitum barbatum var. puberulum. Their structures were elucidated by spectroscopic methods. Puberunine and puberudine, which possess a unique rearranged E ring and an opened A ring, respectively, represent new subtypes of the C(18)-diterpenoid alkaloids. A plausible biosynthetic pathway of 1 and 2 was proposed. PMID:22616819

Mu, Zhen-Qiang; Gao, Hao; Huang, Zhi-Yun; Feng, Xiao-Lin; Yao, Xin-Sheng

2012-06-01

305

Heyneanine hydroxyindolenine, a new indole alkaloid from Ervatamia coronaria var. plena.  

PubMed

The whole plant of Ervatamia coronaria var. plena obtained from Thailand has afforded a new indole alkaloid 19S-heyneanine hydroxyindolenine whose structure was deduced through interpretation of spectral data. Nine known alkaloids, coronaridine, coronaridine hydroxyindolenine, voacangine, voacangine hydroxyindolenine, heyneanine, voacristine, 3-oxo-coronaridine, 3-oxo-voacangine,and voacristine hydroxyindolenine, and six common triterpenoids were also isolated. Coronaridine was the principal cytotoxic alkaloid obtained. PMID:3404150

Sharma, P; Cordell, G A

1988-01-01

306

Alkaloids of the herb sedum acre L. Part I. Chromatographic analysis  

Microsoft Academic Search

Alkaloid extracts from the herb Sedum acre L. (stonecrop) were analysed by the “moist buffered paper” technique in solvent systems of the type nonpolar or weakly polar solvent-aqueous buffer solution, which were found to be much more selective than one-phse systems or liquid-solid systems. In addition to six previously known Sedum alkaloids, three new alkaloids in the extract were demonstrated.

S. Bieganowska; A. Waksmundzki

1976-01-01

307

Pyrrolizidine alkaloids between plants and insects: A new chapter of an old story  

Microsoft Academic Search

Summary Among alkaloids the pyrrolizidine alkaloids (PAs) play a unique role in the interactions between plants and adapted insects. InSenecio spp. (Asteraceae) PAs are synthesized in the roots as alkaloidN-oxides which are specifically translocated into shootsvia the phloem-path and channeled to the preferred sites of storage (e.g. inflorescences) where they are stored in the cell vacuoles. In differentSenecio spp. senecionineN-oxide

Thomas Hartmann

1994-01-01

308

Allelopathy due to purine alkaloids in tea seeds during germination  

Microsoft Academic Search

Summary  During imbibition of whole tea seeds (6 days) two purine alkaloids, caffeine and theobromine, did not decrease in the seed\\u000a coats and there was no increase in the seeds. In parallel with and after the breaking of seed coats there was a gradual release\\u000a of caffeine from coats of germinating seeds. By contrast, when the seed was freed from the

T. Suzuki; G. R. Waller

1987-01-01

309

Anticonvulsant activity of berberine, an isoquinoline alkaloid in mice  

Microsoft Academic Search

Berberine, an isoquinoline alkaloid is reported to modulate several neurotransmitter systems like N-methyl-D-aspartate, nitric oxide and serotonin, which modulate convulsions. In addition, it is suggested that Berberis vulgaris may be useful in treatment of convulsion and epilepsy. Therefore, the present study investigated the effects of berberine in pentylenetetrazole, maximal electroshock (MES) and kainic acid (KA)-induced convulsions. The latency for development

Pravinkumar Bhutada; Yogita Mundhada; Kuldeep Bansod; Pankaj Dixit; Sudhir Umathe; Dharmendra Mundhada

2010-01-01

310

Lodopyridone, a structurally unprecedented alkaloid from a marine actinomycete.  

PubMed

Chemical examination of the secondary metabolites of a marine Saccharomonospora sp., isolated from marine sediments collected at the mouth of the La Jolla Submarine Canyon, yielded the unprecedented alkaloid lodopyridone (1). The low proton-to-carbon ratio of 1 precluded structure elucidation by NMR spectroscopic methods, thus the structure was defined by X-ray crystallography. Lodopyridone is cytotoxic to HCT-116 human colon cancer cells with IC(50) = 3.6 microM. PMID:19883103

Maloney, Katherine N; Macmillan, John B; Kauffman, Christopher A; Jensen, Paul R; Dipasquale, Antonio G; Rheingold, Arnold L; Fenical, William

2009-12-01

311

Effects of pyrrolizidine alkaloids through different trophic levels  

Microsoft Academic Search

Pyrrolizidine alkaloids (PAs), mainly those with a 1,2-double bond in the necine base moiety (=1,2-dehydropyrrolizidines),\\u000a constitute a class of well studied compounds with respect to their flux through different trophic levels. Plants belonging\\u000a to various clades (e.g. Echiteae, Eupatorieae and Senecioneae, Boraginaceae, and Crotalarieae) biosynthesize PAs as N-oxides, generally in the roots, and transport them through the phloem to stems,

José Roberto Trigo

2011-01-01

312

Dimeric Erythrina Alkaloids from the Flower of Erythrina variegata.  

PubMed

Unprecedented dimeric Erythrina alkaloids, spirocyclic (6/5/6/6) erythrivarine A (1) and spiro-fused (6/5/7/6) rings erythrivarine B (2), were isolated from the cultivated plant, E. variegata. The structures were determined on the basis of 1D and 2D NMR, FTIR, UV, and mass spectroscopic data and X-ray crystal diffraction. The biogenetic relationship of 1 and 2 is proposed. PMID:25470209

Zhang, Bing-Jie; Bao, Mei-Fen; Zeng, Chun-Xia; Zhong, Xiu-Hong; Ni, Ling; Zeng, Ying; Cai, Xiang-Hai

2014-12-19

313

Antimalarial activity of alkaloids isolated from Stephania rotunda  

Microsoft Academic Search

Stephania rotunda (Menispermaceae) is used in traditional medicine for the treatment of fever. Four major alkaloids: dehydroroemerine, tetrahydropalmatine, xylopinine, cepharanthine as well as aqueous extract (SA), dichloromethane extracts (SD1 and SD2) from this plant were tested against Plasmodium falciparum W2 in vitro. Dehydroroemerine, cepharanthine and SD1 were the most active against W2 with IC50 of 0.36, 0.61?M and 0.7?g\\/mL, respectively.

Aun Chea; Sotheara Hout; Sok-Siya Bun; Nino Tabatadze; Monique Gasquet; Nadine Azas; Riad Elias; Guy Balansard

2007-01-01

314

Qualitative patterns of pyrrolizidine alkaloids in ithomiinae butterflies  

Microsoft Academic Search

Pynolizidine alkaloids (PAs) were analysed in 40 species (38 genera, all 14 tribes) of the butterfly subfamily Ithomiinae. The principal PAs found were the epimers lycopsamine and intermedine. These results suggest that ithomiines visit mainly PA sources containing moncester lycopsamine-type PAs, and transform various other diastereoisomers into lycopsamine and intermedine, with the 7R configuration. Other PA-types found in butterflies are

JoséRoberto Trigo; Keith S. Brown; Silvana A. Henriques; Lauro Euclides Soares Barata

1996-01-01

315

Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids.  

PubMed

A concise enantioselective approach to the tetracyclic core of the magellanine-type Lycopodium alkaloids is reported. Key to this approach is the use of the Hajos-Parrish reaction to set a challenging quaternary stereocenter, thereby guiding the stereoselectivity for the remainder of the synthesis, as well as the use of a palladium-mediated direct pyridine functionalization reaction to forge the tetracyclic core. PMID:22201223

Murphy, Rebecca A; Sarpong, Richmond

2012-01-20

316

Carinatines A and B, Lycopodium Alkaloids from Phlegmariurus carinatus.  

PubMed

Carinatine A (1), a C16N2-type Lycopodium alkaloid possessing a 5/6/6/6 ring system formed by a new C-4/C-12 bond, and carinatine B (2), the first derivative of lycojaponicumin C, along 16 known compounds, were isolated from the whole plant of Phlegmariurus carinatus. Their structures were elucidated based on the spectroscopic data. The two new isolates were no inhibitory activity for the acetylcholinesterase (AChE). PMID:25089240

Liu, Fei; Liu, Yu-Cheng; Jiang, Wei-Wei; He, Juan; Wu, Xing-De; Peng, Li-Yan; Su, Jia; Cheng, Xiao; Zhao, Qin-Shi

2014-08-01

317

Ultrasonic extraction of steroidal alkaloids from potato peel waste.  

PubMed

Potato processors produce large volumes of waste in the form of potato peel which is either discarded or sold at a low price. Potato peel waste is a potential source of steroidal alkaloids which are biologically active secondary metabolites which could serve as precursors to agents with apoptotic, chemopreventive and anti-inflammatory properties. The present study investigated the relative efficacy of ultrasound assisted extraction (UAE) and solid liquid extraction (SLE) both using methanol, to extract steroidal alkaloids from potato peel waste and identified optimal conditions for UAE of ?-solanine, ?-chaconine, solanidine and demissidine. Using response surface methodology optimal UAE conditions were identified as an amplitude of 61 ?m and an extraction time of 17 min which resulted the recovery of 1102 ?g steroidal alkaloids/g dried potato peel (DPP). In contrast, SLE yielded 710.51 glycoalkaloid ?g/g DPP. Recoveries of individual glycoalkoids using UAE yielded 273, 542.7, 231 and 55.3 ?g/g DPP for ?-solanine, ?-chaconine, solanidine and demissidine respectively. Whereas for SLE yields were 180.3, 337.6, 160.2 and 32.4 ?g/g DPP for ?-solanine, ?-chaconine, solanidine and demissidine respectively. The predicted values from the developed second order quadratic polynomial equation were in close agreement with the experimental values with low average mean deviation (E<5%) values. Predicted models were highly significant (p<0.05) for all parameters studied. This study indicates that UAE has strong potential as an extraction method for steroidal alkaloids from potato peel waste. PMID:24582305

Hossain, Mohammad B; Tiwari, Brijesh K; Gangopadhyay, Nirupama; O'Donnell, Colm P; Brunton, Nigel P; Rai, Dilip K

2014-07-01

318

Toxicity of pyrrolizidine alkaloids to humans and ruminants  

Microsoft Academic Search

1,2-dehydro pyrrolizidine ester alkaloids (PA) are toxic for human and livestock. The PAs undergo a metabolic toxication process\\u000a in the liver which is the first target organ for PA poisoning. World-wide many episodes of PA intoxications have been reported\\u000a involving humans as well as ruminants. This intoxication is not only related to the amount and duration of the exposure to

Helmut Wiedenfeld; John Edgar

2011-01-01

319

A Torquoselective 6? Electrocyclization Approach to Reserpine Alkaloids  

PubMed Central

A highly torquoselective thermal triene 6? electrocyclization controls the relative stereochemistry between the C3 and C18 stereocenters of the dodecahydroindolo[2,3-a]benzo[g]quinolizine skeleton of reserpine-type alkaloids. Employing a tandem cross-coupling/electrocyclization protocol allowed us to form the requisite triene and ensure its subsequent cyclization. A novel low-temperature dibromoketene acetal Claisen rearrangement established the requisite exocyclic dienylbromide precursor for the palladium-catalyzed cross-coupling reaction. PMID:23039026

Barcan, Gregg A.; Patel, Ashay; Houk, K. N.

2012-01-01

320

Improved extraction and complete mass spectral characterization of steroidal alkaloids from Veratrum californicum.  

PubMed

Four steroidal alkaloids extracted from the roots and rhizomes of Veratrum californicum were separated by high performance liquid chromatography (HPLC) and identified using high resolution electrospray ionization time of flight tandem mass spectrometry (ESI-TOF-MS/MS) as veratrosine, cycloposine, veratramine, and cyclopamine. This paper compares ethanol and benzene as extraction solvents, HPLC solvent conditions leading to good separation of steroidal alkaloids, and MS/MS fragmentation patterns for the four steroidal alkaloids which have been released to the public database MassBank.jp. The reported Soxhlet extraction method nearly triples the recovery of steroidal alkaloids from V. californicum. PMID:24079166

Chandler, Christopher M; Habig, Jeffrey W; Fisher, Ashley A; Ambrose, Katherine V; Jiménez, Susana T; McDougal, Owen M

2013-08-01

321

A new isoquinoline alkaloid with anti-microbial properties from Berberis jaeschkeana Schneid. var. jaeschkeana.  

PubMed

One new isoquinoline alkaloid named berberidione (1) along with four new source alkaloids berberine (2), palmatine (3), jatrorrhizine (4) and chondrofoline (5) and three new source non-alkaloids syringic acid (6), ?-sitosterol (7) and stigmasterol (8) was isolated and characterised from different fractions of Berberis jaeschkeana Schneid var. jaeschkeana. All the structures were determined from 1D and 2D spectroscopic data. Crude extract, sub-fractions and isolated compounds showed excellent anti-microbial properties. The toxicity level for the alkaloids was found to be very low on THP-1 cells. PMID:25424893

Alamzeb, Muhammad; Khan, M Rafiullah; Ali, Saqib; Khan, Ashfaq Ahmad

2014-11-25

322

Cytotoxic dimeric quinolone-terpene alkaloids from the root bark of Zanthoxylum rhetsa.  

PubMed

Four quinolone-terpene alkaloids, chelerybulgarine (1), 2'-episimulanoquinoline (3), 2,11-didemethoxyvepridimerine B (4), and rhetsidimerine (5) were isolated from the root bark of Zanthoxylum rhetsa DC. Chelerybulgarine (1) is a C-C linked terpene alkaloid where the C-6 of dihydrochelerythrine is linked to C-11 of the sesquiterpenoid 10?-methoxybulgarene. 2'-Episimulanoquinoline is a dimeric alkaloid containing dihydrochelerythrine and 8-methoxy-N-methylflindersine moieties, whereas 2,11-didemethoxyvepridimerine B and rhetsidimerine are dimeric prenylated quinolone alkaloids. Seven of the isolated compounds exhibited weak cytotoxicity when tested against a panel of six human stomach-cancer cell lines. PMID:24768324

Ahsan, Monira; Haque, Mohammad Rashedul; Hossain, Md Belayet; Islam, Sheikh Nazrul; Gray, Alexander I; Hasan, Choudhury Mahmood

2014-07-01

323

Selective uptake of pyrrolizidine N-oxides by cell suspension cultures from pyrrolizidine alkaloid producing plants.  

PubMed

The N-oxides of pyrrolizidine alkaloids such as senecionine or monocrotaline are rapidly taken up and accumulated by cell suspension cultures obtained from plants known to produce pyrrolizidines, i.e. Senecio vernalis, vulgaris, viscosus (Asteraceae) and Symphytum officinale (Boraginaceae). The transport of the N-oxides into the cells is a specific and selective process. Other alkaloid N-oxides such as sparteine N-oxide are not taken up. Cell cultures from plant species which do not synthesize pyrrolizidine alkaloids are unable to accumulate pyrrolizidine N-oxides. The suitability of the pyrrolizidine N-oxides in alkaloid storage and accumulation is emphasized. PMID:24247963

von Borstel, K; Hartmann, T

1986-02-01

324

Feeding responses to selected alkaloids by gypsy moth larvae, Lymantria dispar (L.)  

NASA Astrophysics Data System (ADS)

Deterrent compounds are important in influencing the food selection of many phytophagous insects. Plants containing deterrents, such as alkaloids, are generally unfavored and typically avoided by many polyphagous lepidopteran species, including the gypsy moth Lymantria dispar (L.) (Lepidoptera: Lymantriidae). We tested the deterrent effects of eight alkaloids using two-choice feeding bioassays. Each alkaloid was applied at biologically relevant concentrations to glass fiber disks and leaf disks from red oak trees ( Quercus rubra) (L.), a plant species highly favored by these larvae. All eight alkaloids tested on glass fiber disks were deterrent to varying degrees. When these alkaloids were applied to leaf disks, only seven were still deterrent. Of these seven, five were less deterrent on leaf disks compared with glass fiber disks, indicating that their potency was dramatically reduced when they were applied to leaf disks. The reduction in deterrency may be attributed to the phagostimulatory effect of red oak leaves in suppressing the negative deterrent effect of these alkaloids, suggesting that individual alkaloids may confer context-dependent deterrent effects in plants in which they occur. This study provides novel insights into the feeding behavioral responses of insect larvae, such as L. dispar, to selected deterrent alkaloids when applied to natural vs artificial substrates and has the potential to suggest deterrent alkaloids as possible candidates for agricultural use.

Shields, Vonnie D. C.; Rodgers, Erin J.; Arnold, Nicole S.; Williams, Denise

2006-03-01

325

New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture.  

PubMed

Three new monoterpenoid indole alkaloids, 19(S),20(R)-dihydroperaksine (1), 19(S),20(R)-dihydroperaksine-17-al (2), and 10-hydroxy-19(S),20(R)-dihydroperaksine (3), along with 16 known alkaloids 4-19 were isolated from hairy root culture of Rauvolfia serpentina, and their structures were elucidated by 1D and 2D NMR analyses. Taking into account the stereochemistry of the new alkaloids and results of preliminary enzymatical studies, the putative biosynthetical relationships between the novel alkaloids are discussed. PMID:12141861

Sheludko, Yuri; Gerasimenko, Irina; Kolshorn, Heinz; Stöckigt, Joachim

2002-07-01

326

Investigation of the Alkaloid Content of Rauwolfia serpentina Roots from Regenerated Plants.  

PubMed

The indole alkaloid content of RAUWOLFIA SERPENTINA roots from regenerated plants (from stem-and root-callus) was compared with the parental stock. Although the total alkaloid content seems to be slightly higher in the roots from regenerated plants, HPLC-analysis of individual alkaloids indicated that the contents of the alkaloids ajmaline ( 1), serpentine ( 2), and reserpine ( 3) are lower than in the roots of the parental stock. The glucoalkaloid raucaffricine ( 4) was identified as a constituent of all samples, thus providing the first evidence for its occurrence in roots of RAUWOLFIA SERPENTINA. PMID:17226170

Ruyter, C M; Akram, M; Illahi, I; Stöckigt, J

1991-08-01

327

Synthesis and Anticancer Activity of all known (?)-Agelastatin Alkaloids  

PubMed Central

The full details for our enantioselective total syntheses of (?)-agelastatins A–F (1–6), the evolution of a new methodology for synthesis of substituted azaheterocycles, and the first side-by-side evaluation of all known (?)-agelastatin alkaloids against nine human cancer cell lines are described. Our concise synthesis of these alkaloids exploits the intrinsic chemistry of plausible biosynthetic precursors and capitalizes on a late-stage synthesis of the C-ring. The critical copper-mediated cross-coupling reaction was expanded to include guanidine-based systems, offering a versatile preparation of substituted imidazoles. The direct comparison of the anticancer activity of all naturally occurring (?)-agelastatins in addition to eight advanced synthetic intermediates enabled a systematic analysis of the structure activity relationship within the natural series. Significantly, (?)-agelastatin A (1) is highly potent against six blood cancer cell lines (20–190 nM) without affecting normal red blood cells (>333 ?M). (?)-Agelastatin A (1) and (?)-agelastatin D (4), the two most potent members of this family, induce dose dependent apoptosis and arrest cells in the G2/M-phase of the cell cycle; however, using confocal microscopy we have determined that neither alkaloid affects tubulin dynamics within cells. PMID:24152243

Han, Sunkyu; Siegel, Dustin S.; Morrison, Karen C.; Hergenrother, Paul J.

2014-01-01

328

Enantioselective total syntheses of manzamine a and related alkaloids.  

PubMed

As a prelude to undertaking the total syntheses of the complex manzamine alkaloids, a series of model studies were conducted to establish the scope and limitations of intramolecular [4 + 2] cycloadditions of N-acylated vinylogous ureas with the trienic substrates 17a,b, 28a,b, and 34. These experiments clearly demonstrated that the geometry of the internal double bond and the presence of an electron-withdrawing group on the diene moiety were essential for the facile and stereoselective formation of the desired cycloadducts. The enantioselective syntheses of the manzamine alkaloids ircinol A (75), ircinal A (5), and manzamine A (1) were then completed by employing a convergent strategy that featured a novel domino Stille/Diels-Alder reaction to construct the tricyclic ABC ring core embodied in these alkaloids. Thus, the readily accessible chiral dihydropyrrole 58 was first converted in a single chemical operation into the key tricyclic intermediate 60. Two ring-closing metathesis reactions were then used to form the 13- and 8-membered rings leading to Z-72 and 74, the latter of which was quickly elaborated into ircinal A (5) via ircinol A (75). The synthetic 5 thus obtained was converted into manzamine A (1) following literature precedent. This concise synthesis of ircinal A required a total of 24 operations from commercially available starting materials with the longest linear sequence being 21 steps. PMID:12121099

Humphrey, John M; Liao, Yusheng; Ali, Amjad; Rein, Tobias; Wong, Yue-Ling; Chen, Hui-Ju; Courtney, Anne K; Martin, Stephen F

2002-07-24

329

Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin.  

PubMed

Pyrrolizidine alkaloid-containing plants are probably the most common poisonous plants affecting livestock, wildlife, and humans. Pyrrolizidine alkaloids exert toxicity through metabolism to dehydropyrrolizidine alkaloids that bind to cellular protein and DNA, leading to hepatotoxicity, genotoxicity, and tumorigenicity. To date, it is not clear how dehydropyrrolizidine alkaloids bind to cellular constituents, including amino acids and proteins, resulting in toxicity. Metabolism of carcinogenic monocrotaline, riddelliine, and heliotrine produces dehydromonocrotaline, dehyroriddelliine, and dehydroheliotrine, respectively, as primary reactive metabolites. In this study, we report that reaction of dehydromonocrotaline with valine generated four highly unstable 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived valine (DHP-valine) adducts. For structural elucidation, DHP-valine adducts were derivatized with phenyl isothiocyanate (PITC) to DHP-valine-PITC products. After HPLC separation, their structures were characterized by mass spectrometry, UV-visible spectrophotometry, (1)H NMR, and (1)H-(1)H COSY NMR spectral analysis. Two DHP-valine-PITC adducts, designated as DHP-valine-PITC-1 and DHP-valine-PITC-3, had the amino group of valine linked to the C7 position of the necine base, and the other two DHP-valine-PITC products, DHP-valine-PITC-2 and DHP-valine-PITC-4, linked to the C9 position of the necine base. DHP-valine-PITC-1 was interconvertible with DHP-valine-PITC-3, and DHP-valine-PITC-2 was interconvertible with DHP-valine-PITC-4. Reaction of dehydroriddelliine and dehydroheliotrine with valine provided similar results. However, reaction of valine and dehydroretronecine (DHR) under similar experimental conditions did not produce DHP-valine adducts. Reaction of dehydromonocrotaline with rat hemoglobin followed by derivatization with PITC also generated the same four DHP-valine-PITC adducts. This represents the first full structural elucidation of protein conjugated pyrrolic adducts formed from reaction of dehydropyrrolizidine alkaloids with an amino acid (valine). In addition, it was found that DHP-valine-2 and DHP-valine-4, with the valine amino group linked at the C7 position of the necine base, can lose the valine moiety to form DHP. PMID:25211425

Zhao, Yuewei; Wang, Shuguang; Xia, Qingsu; Gamboa da Costa, Gonçalo; Doerge, Daniel R; Cai, Lining; Fu, Peter P

2014-10-20

330

Study on the anti-inflammatory action of Berberis vulgaris root extract, alkaloid fractions and pure alkaloids.  

PubMed

Extracts obtained from the roots of Berberidaceae species have been used in Eastern and Bulgarian folk medicine in rheumatic and other chronic inflammatory disorders. The investigations of the chemical composition and immunological properties show that their activity is mainly due to the alkaloid constituents. In the present study the anti-inflammatory properties of total ethanol extract (TEE), three alkaloid fractions, a major alkaloid berberine and oxyacanthine isolated from Berberis vulgaris roots were compared. All these were applied in acute inflammation (carrageenan- and zymosan-induced paw oedema), as the TEE showed the highest reducing effect. Their ability to alter in vivo and in vitro complement activity was determined. Also, the TEE was most effective in a chronic inflammatory model of adjuvant arthritis. The protoberberine fractions Bv2, Bv3 and berberine suppressed a delayed type hypersensitivity (DTH) reaction. Fraction Bv1 and berberine diminished antibody response against SRBC in vivo. The in vitro treatment of splenocytes with berberine showed that the anti-SRBC antibody synthesis was influenced in a different manner depending on the time course of its application. Oxyacanthine was less effective than berberine in the tests used. PMID:9080249

Ivanovska, N; Philipov, S

1996-10-01

331

Design Constraints in Practical Syntheses of Complex Molecules: Current Status, Case Studies with Carbohydrates and Alkaloids, and Future  

E-print Network

with Carbohydrates and Alkaloids, and Future Perspectives Tomas Hudlicky Department of Chemistry, University 23 IV. Selected Examples 24 1. Carbohydrate Synthesis 24 2. Alkaloid Synthesis 25 V. Summary 27 "What

Hudlicky, Tomas

332

The evolution of LOL, the secondary metabolite gene cluster for insecticidal loline alkaloids in fungal endophytes of grasses.  

E-print Network

LOL is a novel secondary metabolite gene cluster associated with the production of loline alkaloids (saturated 1-aminopyrrolizidine alkaloids with an oxygen bridge) exclusively in closely related grass-endophyte species in the genera Epichloë...

Kutil, Brandi Lynn

2009-05-15

333

Dehydropyrrolizidine alkaloids in two Cryptantha species: Including two new open chain diesters one of which is amphoteric  

Technology Transfer Automated Retrieval System (TEKTRAN)

A livestock poisoning outbreak near Kingman, Arizona, USA, potentially linked to dehydropyrrolizidine alkaloids, prompted an evaluation of some local plants for the presence of these hepatotoxic alkaloids. Two species of Cryptantha, a Boraginaceous genus previously shown to produce potentially toxic...

334

An ergot alkaloid biosynthesis gene and clustered hypothetical genes from Aspergillus fumigatus.  

PubMed

The ergot alkaloids are a family of indole-derived mycotoxins with a variety of significant biological activities. Aspergillus fumigatus, a common airborne fungus and opportunistic human pathogen, and several fungi in the relatively distant taxon Clavicipitaceae (clavicipitaceous fungi) produce different sets of ergot alkaloids. The ergot alkaloids of these divergent fungi share a four-member ergoline ring but differ in the number, type, and position of the side chains. Several genes required for ergot alkaloid production are known in the clavicipitaceous fungi, and these genes are clustered in the genome of the ergot fungus Claviceps purpurea. We investigated whether the ergot alkaloids of A. fumigatus have a common biosynthetic and genetic origin with those of the clavicipitaceous fungi. A homolog of dmaW, the gene controlling the determinant step in the ergot alkaloid pathway of clavicipitaceous fungi, was identified in the A. fumigatus genome. Knockout of dmaW eliminated all known ergot alkaloids from A. fumigatus, and complementation of the mutation restored ergot alkaloid production. Clustered with dmaW in the A. fumigatus genome are sequences corresponding to five genes previously proposed to encode steps in the ergot alkaloid pathway of C. purpurea, as well as additional sequences whose deduced protein products are consistent with their involvement in the ergot alkaloid pathway. The corresponding genes have similarities in their nucleotide sequences, but the orientations and positions within the cluster of several of these genes differ. The data indicate that the ergot alkaloid biosynthetic capabilities in A. fumigatus and the clavicipitaceous fungi had a common origin. PMID:15933009

Coyle, Christine M; Panaccione, Daniel G

2005-06-01

335

Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea Mirka Macel*, Klaas Vrieling, Peter G.L. Klinkhamer  

E-print Network

Variation in pyrrolizidine alkaloid patterns of Senecio jacobaea Mirka Macel*, Klaas Vrieling the variation in pyrrolizidine alkaloid (PA) patterns of lab-grown vegetative plants of 11 European Senecio alkaloids; Chemotypes; Jacobine; Erucifoline 1. Introduction Plants from the genus Senecio (Asteraceae

Klinkhamer, Peter

336

Guanidine alkaloid analogs as inhibitors of HIV-1 Nef interactions with p53, actin, and p56lck  

E-print Network

Guanidine alkaloid analogs as inhibitors of HIV-1 Nef interactions with p53, actin, and p56lck-3 were used to identify a series of guanidine alkaloid-based inhibi- tors of Nef interactions with p53 efficacy of Nef inhibitors. Nef inhibition by the gua- nidine alkaloid congeners reported here could

Weiss, Gregory A.

337

Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders of the genus Salamandra (Salamandridae)  

E-print Network

Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders steroidal alkaloid toxins in high concen- trations in their skin secretions. This study reconstructs and/or samandarone steroidal alkaloids in all species of Salamandra as well as in representatives

Carranza, Salvador

338

1800 J. Org. Chem. 1995,60,1800-1805 Efficient Syntheses of the Marine Alkaloids Makaluvamine D and  

E-print Network

1800 J. Org. Chem. 1995,60,1800-1805 Efficient Syntheses of the Marine Alkaloids Makaluvamine D of the biologically active pyrrolo[4,3,2-del- quinoline marine alkaloids discorhabdin C (1)and makaluvamine D (3 is the structurally varied group of alkaloids containing the pyrrolo[4,3,2- delquinoline nucleus. These include

Culpepper, J. Shane

339

Very Short and Efficient Syntheses of the Spermine Alkaloid Kukoamine A and Analogs Using Isolable Succinimidyl Cinnamates  

E-print Network

Very Short and Efficient Syntheses of the Spermine Alkaloid Kukoamine A and Analogs Using Isolable yields of the spermine alkaloid kukoamine A and analogs suita- ble for structure-activity relationship-hydroxysuccini- mide in the presence of N,N0 -dicyclohexylcarbodiimide. Kukoamine A (KukA, 1a), a spermine alkaloid

Schnaufer, Achim

340

Time-dependent inhibitors of trypanothione reductase: Analogues of the spermidine alkaloid lunarine and related natural products  

E-print Network

Time-dependent inhibitors of trypanothione reductase: Analogues of the spermidine alkaloid lunarine November 2005 Available online 21 November 2005 Abstract--The macrocyclic spermidine alkaloid lunarine 1 molecules related to 1 and the alkaloid itself have been synthesized in racemic form and evaluated against

Schnaufer, Achim

341

vol. 156, no. 1 the american naturalist july 2000 Alkaloid Uptake Increases Fitness in a Hemiparasitic Plant via  

E-print Network

vol. 156, no. 1 the american naturalist july 2000 Alkaloid Uptake Increases Fitness on herbivores and pollinators in the field. Here, I show that the uptake of alkaloids in the annual hemiparasite, and increased lifetime seed production. These results indicate that resistance traits such as alkaloids can

Harms, Kyle E.

342

Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders of the genus Salamandra (Salamandridae)  

E-print Network

Nuclear and mitochondrial multilocus phylogeny and survey of alkaloid content in true salamanders coloration, known to contain steroidal alkaloid toxins in high concen- trations in their skin secretions and/or samandarone steroidal alkaloids in all species of Salamandra as well as in representatives

Carranza, Salvador

343

The ergot alkaloid gene cluster in Claviceps purpurea: Extension of the cluster sequence and intra species evolution  

Microsoft Academic Search

The genomic region of Claviceps purpurea strain P1 containing the ergot alkaloid gene cluster [Tudzynski, P., Hölter, K., Correia, T., Arntz, C., Grammel, N., Keller, U., 1999. Evidence for an ergot alkaloid gene cluster in Claviceps purpurea. Mol. Gen. Genet. 261, 133–141] was explored by chromosome walking, and additional genes probably involved in the ergot alkaloid biosynthesis have been identified.

Thomas Haarmann; Caroline Machado; Yvonne Lübbe; Telmo Correia; Christopher L. Schardl; Daniel G. Panaccione; Paul Tudzynski

2005-01-01

344

YEAR TO YEAR VARIATION IN ALKALOID CONCENTRATION IN LUPINUS LEUCOPHYLLUS GROWING ON THE SCABLANDS OF CENTRAL WASHINGTON  

Technology Transfer Automated Retrieval System (TEKTRAN)

There was substantial year to year variation in total alkaloid concentration of lupines at all sites. Total alkaloid concentration over the 5 year period varied from two-fold to eight-fold at the individual sites. In any one year the change-trend in total alkaloid concentration was the same at eac...

345

Evaluation of analgesic activity and toxicity of alkaloids in Myristica fragrans seeds in mice  

PubMed Central

Aim To examine the analgesic effect of alkaloids in Myristica fragrans seed in a mouse model of acetic acid-induced visceral pain. Methods Alkaloids were extracted from ground nutmeg seed kernels with 10% acetic acid in 95% ethyl alcohol. Visceral pain was induced in male and female BALB/c mice by intraperitoneal injection of 0.6% acetic acid. Analgesic effect of alkaloids (0.5 gram or 1 gram per kilogram [g/kg], by mouth) was assessed by evaluating writhing response. Acute toxicity was tested in response to 2, 3, 4, 5, or 6 g/kg of alkaloid extract; the median lethal dose (LD50) was determined by probit analysis. Results Alkaloid extract at a dose of 1 g/kg significantly reduced the number of writhing responses in female, but not male mice; 0.5 g/kg of alkaloid extract had no effect in either sex. The LD50 was 5.1 g/kg. Signs of abnormal behavior, including hypoactivity, unstable gait, and dizziness were seen in animals given a dose of 4 g/kg or higher; abnormal behavior lasted for several hours after administration of the alkaloids. Conclusion According to the classification of Loomis and Hayes, M. fragrans seed alkaloids have analgesic activity and are slightly toxic. PMID:23946667

Hayfaa, A Al-Shammary; Sahar, AA Malik Al-Saadi; Awatif, M Al-Saeidy

2013-01-01

346

Improved detection of alkaloids in crude extracts applying capillary electrophoresis with field amplified sample injection  

Microsoft Academic Search

A simple and effective method for the sensitive detection of alkaloids in crude plant extracts applying capillary electrophoresis with field amplified sample injection (FASI) is described. This method was compared with normal pressure injection for the determination of alkaloids in methanolic extracts from roots of Berberis vulgaris L. (Berberidaceae) and Hydrastis canadensis L. (Ranunculaceae) using a 1:1 mixture of 200

Matthias Unger; Joachim Stöckigt

1997-01-01

347

Kitasetaline, a novel ?-carboline alkaloid from Kitasatospora setae NBRC 14216T.  

PubMed

With the genetically modified Kitasatospora setae NBRC 14216(T) strain, a new ?-carboline alkaloid, kitasetaline (1), was produced on solid medium. The structure was elucidated on the basis of physicochemical evidence. This is the first report of this type of alkaloid found in the genus Kitasatospora. PMID:22561881

Aroonsri, Aiyada; Kitani, Shigeru; Ikeda, Haruo; Nihira, Takuya

2012-07-01

348

Effect of Feeding Fescue Seed Containing Ergot Alkaloid Toxins on Stallion Spermatogenesis and Sperm Cells  

PubMed Central

Contents The cellular effects of tall fescue grass–associated toxic ergot alkaloids on stallion sperm and colt testicular tissue were evaluated. This was a continuation of an initial experiment where the effects of toxic ergot alkaloids on the stallion spermiogram were investigated. The only spermiogram parameter in exposed stallions that was affected by the toxic ergot alkaloids was a decreased gel-free volume of the ejaculate. This study examined the effect of toxic ergot alkaloids on chilling and freezing of the stallion sperm cells. The effect of toxic ergot alkaloids on chilled extended sperm cells for 48 h at 5 °C was to make the sperm cells less likely to undergo a calcium ionophore–induced acrosome reaction. The toxic ergot alkaloids had no effect on the freezability of sperm cells. However, if yearling colts were fed toxic ergot alkaloids, then the cytological analysis of meiotic chromosome synapsis revealed a significant increase in the proportion of pachytene spermatocytes showing unpaired sex chromosomes compared to control spermatocytes. There was little effect of ergot alkaloids on adult stallions, but there might be a significant effect on yearling colts. PMID:22524585

Fayrer-Hosken, R; Stanley, A; Hill, N; Heusner, G; Christian, M; Fuente, R De La; Baumann, C; Jones, L

2012-01-01

349

Dimerization of (+)-Myrmicarin 215B. A Potential Biomimetic Approach to Complex Myrmicarin Alkaloids  

PubMed Central

The acid promoted diastereoselective dimerization of myrmicarin 215B is described. The reactivity of these sensitive alkaloids, structural assignment, and a possible mechanism for the observed dimerization are discussed. These finding raise the intriguing possibility of the synthesis of the highly sensitive myrmicarin alkaloids based on a strategy involving the direct dimerization of functional tricyclic myrmicarin derivatives. PMID:20640170

Ondrus, Alison E.; Movassaghi, Mohammad

2009-01-01

350

Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus  

Microsoft Academic Search

The alkaloid composition of 56 species (90 taxa if all subspecies and chemotypes are included) of the genus Lupinus was studied by capillary gas-liquid chromatography and GLC-mass spectrometry (GC-EIMS). The distribution of 100 alkaloids (quinolizidines, piperidines, dipiperidines and simple indoles) and their relative abundances in leaves and seeds (if available) are recorded.

Michael Wink; Carsten Meißner; Ludger Witte

1995-01-01

351

Partial Reconstruction of the Ergot Alkaloid Pathway by Heterologous Gene Expression in Aspergillus nidulans  

PubMed Central

Ergot alkaloids are pharmaceutically and agriculturally important secondary metabolites produced by several species of fungi. Ergot alkaloid pathways vary among different fungal lineages, but the pathway intermediate chanoclavine-I is evolutionarily conserved among ergot alkaloid producers. At least four genes, dmaW, easF, easE, and easC, are necessary for pathway steps prior to chanoclavine-I; however, the sufficiency of these genes for chanoclavine-I synthesis has not been established. A fragment of genomic DNA containing dmaW, easF, easE, and easC was amplified from the human-pathogenic, ergot alkaloid-producing fungus Aspergillus fumigatus and transformed into Aspergillus nidulans, a model fungus that does not contain any of the ergot alkaloid synthesis genes. HPLC and LC-MS analyses demonstrated that transformed A. nidulans strains produced chanoclavine-I and an earlier pathway intermediate. Aspergillus nidulans transformants containing dmaW, easF, and either easE or easC did not produce chanoclavine-I but did produce an early pathway intermediate and, in the case of the easC transformant, an additional ergot alkaloid-like compound. We conclude that dmaW, easF, easE, and easC are sufficient for the synthesis of chanoclavine-I in A. nidulans and expressing ergot alkaloid pathway genes in A. nidulans provides a novel approach to understanding the early steps in ergot alkaloid synthesis. PMID:23435153

Ryan, Katy L.; Moore, Christopher T.; Panaccione, Daniel G.

2013-01-01

352

Origin of sclerotia-like cells in submerged Claviceps purpurea producing clavine alkaloids  

Microsoft Academic Search

Ultrathin sectioning of submerged mycelium of Claviceps purpurea Tul. producing clavine alkaloids revealed yeast-like budding resulting in asexual sporesblastospores. These deciduous spores were born by extended hyphal cells and retained the same ultrastructure of cell organelles. Both the extended hyphae and the blastospores resembled the cells of ergot sclerotial tissue. A surface culture of C. purpurea Tul. producing no alkaloids

Josef Vo?íšek; Zden?k ?ehá?ek

1976-01-01

353

Mechanism of alkaloid cyclopeptide synthesis in the ergot fungus Claviceps purpurea  

Microsoft Academic Search

Background: Previous analyses of the biosynthesis of the alkaloid cyclopeptides from the ergot fungus Claviceps purpurea were hampered by a lack of suitable systems for study in vitro, and this led to conflicting results concerning the mechanism of alkaloid cyclopeptide formation. Recently, D-lysergyl peptide synthetase (LPS) of the ergot fungus Claviceps purpurea, which assembles the non-cyclol precursors of the ergopeptines,

Bernd Walzel; Brigitte Riederer; Ullrich Keller

1997-01-01

354

Carmichaeline A: a new C20-diterpenoid alkaloid from Aconitum carmichaeli.  

PubMed

The roots of Aconitum carmichaeli Debx. are known for their medicinal value. A new C20-diterpenoid alkaloid designated as carmichaeline A (1) has been isolated, along with eight known diterpenoid alkaloids from the roots of the plant. Their structures were elucidated on the basis of spectroscopic data interpretation. PMID:23513715

Li, Shu-Hua; Xiong, Jun-Ru; Zhang, Yuan-Qin; Xiang, Qing-Xiang; Chen, Feng-Zheng

2013-02-01

355

A new C??-diterpenoid alkaloid from the roots of Aconitum duclouxii.  

PubMed

A new C??-diterpenoid alkaloid, ducloudine F (1), was obtained from the roots of Aconitum duclouxii, along with eight known alkaloids (2-9) isolated from this species for the first time. Their structures were established on the basis of extensive spectroscopic analyses. The antimicrobial activities of these compounds were investigated. PMID:24947874

Yin, Tian-Peng; Cai, Le; Zhou, Hao; Zhu, Xiu-Fang; Chen, Yang; Ding, Zhong-Tao

2014-01-01

356

Antiplatelet activity of ?-carboline alkaloids from Perganum harmala: A possible mechanism through inhibiting PLC?2 phosphorylation  

Microsoft Academic Search

Beta-carboline alkaloids including harmalol, harmaline, norharmane, harmol, harmine and harmane are important constituents of the medicinal plant, Perganum harmala L. (Zygophylaceae), which has been used in traditional medicine. In the present study, the antiplatelet activities of six ?-carboline alkaloid compounds were investigated in vitro. At a concentration of 200 ?M, these compounds have no effect on arachidonic acid (AA)-, thrombin- and

Ji-Hyun Im; Yong-Ri Jin; Jung-Jin Lee; Ji-Yeon Yu; Xiang-Hua Han; Se-Hyuk Im; Jin Tae Hong; Hwan-Soo Yoo; Myoung-Yun Pyo; Yeo-Pyo Yun

2009-01-01

357

Taxonomic implications of diterpene alkaloids in three toxic tall larkspur species ( Delphinium spp.)  

Microsoft Academic Search

The diterpene alkaloid content was used to assess the chemical taxonomic diversity in three larkspur species. Samples (n=163) were collected from 18 different locations in five western states, extracted and analyzed for diterpene alkaloids using electrospray mass spectrometry. The data were statistically analyzed using canonical discriminant analysis and analysis of variance. Delphinium glaucum samples were easily grouped and were significantly

D. R Gardner; M. H Ralphs; D. L Turner; S. L Welsh

2002-01-01

358

A Tale of Three Cell Types: Alkaloid Biosynthesis Is Localized to Sieve Elements in Opium Poppy  

Microsoft Academic Search

Opium poppy produces a diverse array of pharmaceutical alkaloids, including the narcotic analgesics morphine and codeine. The benzylisoquinoline alkaloids of opium poppy accumulate in the cytoplasm, or latex, of specialized laticifers that accom- pany vascular tissues throughout the plant. However, immunofluorescence labeling using affinity-purified antibodies showed that three key enzymes, ( S )- N -methylcoclaurine 3 ? -hydroxylase (CYP80B1), berberine

David A. Bird; Vincent R. Franceschi; Peter J. Facchini

2003-01-01

359

Separation and Quantitation of Seven Ergot Alkaloids in Bovine Vein Tissue  

Technology Transfer Automated Retrieval System (TEKTRAN)

Ergot alkaloid related toxicosis has been documented in forage animals for over thirty years, but few mass spectrometry analytical methods for the detection and quantitation of these compounds exist. A primary ergot alkaloid of interest was ergovaline, the predominant toxicant in endophyte-inf...

360

Cytochromes P450 in the biosynthesis of glucosinolates and indole alkaloids  

Microsoft Academic Search

Characteristic of cruciferous plants is the synthesis of nitrogen- and sulfur-rich compounds, such as glucosinolates and indole alkaloids. The intact glucosinolates have limited biological activity, but give rise to an array of bio-active breakdown products when hydrolysed by endogenous ?-thioglucosidases (myrosinases) upon tissue disruption. Both glucosinolates and indole alkaloids constitute an important part of the defence of plants against herbivores

Majse Nafisi; Ida E. Sønderby; Bjarne G. Hansen; Fernando Geu-Flores; Hussam H. Nour-Eldin; Morten H. H. Nørholm; Niels B. Jensen; Jing Li; Barbara A. Halkier

2006-01-01

361

Two New Cytotoxic Indole Alkaloids from a Deep-Sea Sediment Derived Metagenomic Clone  

PubMed Central

Two new indole alkaloids, metagenetriindole A (1) and metagenebiindole A (2), were identified from deep-sea sediment metagenomic clone derived Escherichia coli fermentation broth. The structures of new compounds were elucidated by spectroscopic methods. The two new indole alkaloids demonstrated moderately cytotoxic activity against CNE2, Bel7402 and HT1080 cancer cell lines in vitro. PMID:24717525

Yan, Xia; Tang, Xi-Xiang; Chen, Lin; Yi, Zhi-Wei; Fang, Mei-Juan; Wu, Zhen; Qiu, Ying-Kun

2014-01-01

362

Anthranilate synthase from Ruta graveolens. Duplicated AS alpha genes encode tryptophan-sensitive and tryptophan-insensitive isoenzymes specific to amino acid and alkaloid biosynthesis.  

PubMed Central

Anthranilate synthase (AS, EC 4.1.3.27) catalyzes the conversion of chorismate into anthranilate, the biosynthetic precursor of both tryptophan and numerous secondary metabolites, including inducible plant defense compounds. The higher plant Ruta graveolens produces tryptophan and elicitor-inducible, anthranilate-derived alkaloids by means of two differentially expressed nuclear genes for chloroplast-localized AS alpha subunits, AS alpha 1 and AS alpha 2. Mechanisms that partition chorismate between tryptophan and inducible alkaloids thus do not entail chloroplast/cytosol separation of AS isoenzymes and yet might involve differential feedback regulation of pathway-specific AS alpha subunits. The two AS alpha isoenzymes of R. graveolens were expressed as glutathione S-transferase fusion proteins in Escherichia coli deletion mutants defective in AS activity and were purified to homogeneity. Differential sensitivity of the transformed E. coli strains toward 5-methyltryptophan, a false-feedback inhibitor of AS, was demonstrated. Characterization of affinity-purified AS alpha isoenzymes revealed that the noninducible AS alpha 2 of R. graveolens is strongly feedback inhibited by 10 microns tryptophan. In contrast, the elicitor-inducible AS alpha 1 isoenzyme is only slightly affected even by tryptophan concentrations 10-fold higher than those observed in planta. These results are consistent with the hypothesis that chorismate flux into biosynthesis of tryptophan and defense-related alkaloid biosynthesis in R. graveolens is regulated at the site of AS alpha isoenzymes at both genetic and enzymatic levels. PMID:8787026

Bohlmann, J; Lins, T; Martin, W; Eilert, U

1996-01-01

363

Alteration of the alkaloid profile in genetically modified tobacco reveals a role of methylenetetrahydrofolate reductase in nicotine N-demethylation.  

PubMed

Methylenetetrahydrofolate reductase (MTHFR) is a key enzyme of the tetrahydrofolate (THF)-mediated one-carbon (C1) metabolic network. This enzyme catalyzes the reduction of 5,10-methylene-THF to 5-methyl-THF. The latter donates its methyl group to homocysteine, forming methionine, which is then used for the synthesis of S-adenosyl-methionine, a universal methyl donor for numerous methylation reactions, to produce primary and secondary metabolites. Here, we demonstrate that manipulating tobacco (Nicotiana tabacum) MTHFR gene (NtMTHFR1) expression dramatically alters the alkaloid profile in transgenic tobacco plants by negatively regulating the expression of a secondary metabolic pathway nicotine N-demethylase gene, CYP82E4. Quantitative real-time polymerase chain reaction and alkaloid analyses revealed that reducing NtMTHFR expression by RNA interference dramatically induced CYP82E4 expression, resulting in higher nicotine-to-nornicotine conversion rates. Conversely, overexpressing NtMTHFR1 suppressed CYP82E4 expression, leading to lower nicotine-to-nornicotine conversion rates. However, the reduced expression of NtMTHFR did not affect the methionine and S-adenosyl-methionine levels in the knockdown lines. Our finding reveals a new regulatory role of NtMTHFR1 in nicotine N-demethylation and suggests that the negative regulation of CYP82E4 expression may serve to recruit methyl groups from nicotine into the C1 pool under C1-deficient conditions. PMID:23221678

Hung, Chiu-Yueh; Fan, Longjiang; Kittur, Farooqahmed S; Sun, Kehan; Qiu, Jie; Tang, She; Holliday, Bronwyn M; Xiao, Bingguang; Burkey, Kent O; Bush, Lowell P; Conkling, Mark A; Roje, Sanja; Xie, Jiahua

2013-02-01

364

Differential alkaloid profile in Uncaria tomentosa micropropagated plantlets and root cultures.  

PubMed

The alkaloids of Uncaria tomentosa micropropagated plantlets and root cultures were isolated and identified by NMR and mass spectrometry. Plantlets yielded pteropodine (1), isopteropodine (2), mitraphylline (3), isomitraphylline (4), uncarine F (5), speciophylline (6), rhynchophylline (7) and isorhynchophylline (8). In plantlets growing under continuous light, tetracyclic alkaloids 7 and 8 decreased from 20 ± 1.8 at 2 months to 2.2 ± 0.33 mg/g dry wt at 6 months, while the pentacyclic alkaloids 1-4 increased from 7.7 ± 1.4 to 15 ± 0.05 mg/g dry wt, supporting their biogenetic conversion. Micropropagated plantlets produced four times more alkaloids (27.6 ± 3.1 mg/g dry wt) than greenhouse plants. Plantlet roots yielded 3, 4, 8 and the glucoindole alkaloids 3?-dihydrocadambine (9) and dolichantoside (10), the last one not previously found in Uncaria. PMID:23296316

Luna-Palencia, Gabriela R; Huerta-Heredia, Ariana A; Cerda-García-Rojas, Carlos M; Ramos-Valdivia, Ana C

2013-05-01

365

Wild daffodils of the section Ganymedes from the Iberian Peninsula as a source of mesembrane alkaloids.  

PubMed

The aim of this work was to perform a detailed study of the alkaloid content of Narcissus triandrus, as well as a complete analysis of the alkaloid profile of 18 wild populations, comprising all the taxa of the section Ganymedes. Through the application of a combination of spectroscopic and chromatographic methods, the isolation and structural elucidation of 3 compounds are reported for the first time from a natural source (2-oxomesembrenone, 7,7a-dehydromesembrenone and 2-oxoepimesembranol), together with the identification of 5 major common mesembrane alkaloids. Additionally, the GC-MS analysis of the alkaloid profile demonstrated the regular presence of mesembranes in all the studied plants, showing mesembrenone as the predominant compound without any typical Amaryllidaceae alkaloid being detected. PMID:23932506

Pigni, Natalia B; Ríos-Ruiz, Segundo; Luque, F Javier; Viladomat, Francesc; Codina, Carles; Bastida, Jaume

2013-11-01

366

Effects of tryptophan derivatives and ?-carboline alkaloids on radiation- and peroxide-induced transformations of ethanol  

NASA Astrophysics Data System (ADS)

The subject of this study was investigation of interactions of tryptophan and its derivatives, including structurally related ?-carboline alkaloids with oxygen- and carbon-centered radicals being formed during radiation- and peroxide-induced transformations of ethanol. It was shown that the above named compounds suppressed recombination and disproportionation reactions of ?-hydroxyethyl radicals. The inhibitory effects of tryptophan, 5-hydroxytryptophan and serotonin were mainly realized by means of reduction and addition reactions, while those of ?-carboline alkaloids - harmine, harmane and harmaline - were due to oxidation reactions. Melatonin displayed low reactivity towards ?-hydroxyethyl radicals. Tryptophan derivatives and ?-carboline alkaloids were found to inhibit radiation-induced oxidation of ethanol while being virtually not used up. The low transformation yields of tryptophan, 5-hydroxytryptophan and serotonin, as well as ?-carboline alkaloids, indicate their capability of regeneration, which could occur on interaction of tryptophan with ?-2 and ??2, or on oxidation of ?-hydroxyethyl radicals by ?-carboline alkaloids.

Sverdlov, R. L.; Brinkevich, S. D.; Shadyro, O. I.

2014-05-01

367

In vitro antiplasmodial, antiamoebic, and cytotoxic activities of a series of bisbenzylisoquinoline alkaloids.  

PubMed Central

Twenty-four bisbenzylisoquinoline alkaloids were screened for antiplasmoidal, antiamoebic, and cytotoxic activities by use of in vitro microtests. Eight of the alkaloids had antiplasmodial activity, with a 50% inhibitory concentration (IC50) of less than 1 microM against a multidrug-resistant strain of Plasmodium falciparum (chloroquine had an IC50 of 0.2 microM). The three alkaloids most active against Entamoeba histolytica, aromoline, isotrilobine, and insularine, had IC50s of 5 to 11.1 microM (metronidazole had an IC50 of 1.87 microM). None of the 24 bisbenzylisoquinoline alkaloids exhibited significant cytotoxicity against the KB cell line, the most toxic being berbamine, with an IC50 of 17.8 microM (the IC50 of podophyllotoxin was 0.008 microM). Bisbenzylisoquinoline alkaloids merit further investigation as potential novel antimalarial agents. PMID:8141587

Marshall, S J; Russell, P F; Wright, C W; Anderson, M M; Phillipson, J D; Kirby, G C; Warhurst, D C; Schiff, P L

1994-01-01

368

Tall fescue seed extraction and partial purification of ergot alkaloids  

PubMed Central

Many substances in the tall fescue/endophyte association (Schedonorus arundinaceus/Epichloë coenophiala) have biological activity. Of these compounds only the ergot alkaloids are known to have significant mammalian toxicity and the predominant ergot alkaloids are ergovaline and ergovalinine. Because synthetically produced ergovaline is difficult to obtain, we developed a seed extraction and partial purification protocol for ergovaline/ergovalinine that provided a biologically active product. Tall fescue seed was ground and packed into several different sized columns for liquid extraction. Smaller particle size and increased extraction time increased efficiency of extraction. Our largest column was a 114 × 52 × 61 cm (W × L × D) stainless steel tub. Approximately 150 kg of seed could be extracted in this tub. The extraction was done with 80% ethanol. When the solvent front migrated to bottom of the column, flow was stopped and seed was allowed to steep for at least 48 h. Light was excluded from the solvent from the beginning of this step to the end of the purification process. Following elution, ethanol was removed from the eluate by evaporation at room temperature and the resulting syrup was freeze-dried. About 80% recovery of alkaloids was achieved with 18-fold increase in concentration of ergovaline. Initial purification of the dried product was accomplished by extracting with hexane/water (6:1, v/v). The aqueous fraction was extracted with chloroform, the aqueous layer discarded, after which the chloroform was removed with a resulting 20-fold increase of ergovaline. About 65% of the ergovaline was recovered from the chloroform residue for an overall recovery of 50%. The resultant partially purified ergovaline had biological activities in in vivo and in vitro bovine bioassays that approximate that of synthetic ergovaline. PMID:25566528

Ji, Huihua; Fannin, F.; Klotz, J.; Bush, Lowell

2014-01-01

369

Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax.  

PubMed

The ergot alkaloid ergovaline has demonstrated a persistent and sustained contractile response in several different vascular models. It was hypothesized that different alkaloids isolated from tall fescue (Lolium arundinaceum) will contribute to this contractile response differently. The objective was to compare contractile-response patterns of single additions of the ergoline alkaloids lysergic acid, lysergol, and ergonovine and the ergopeptine alkaloids ergotamine, ergocristine, ergocryptine, ergocornine, and ergovaline (provided as tall fescue seed extract). Lateral saphenous veins were collected from 6 Holstein steers (BW = 397 ± 28 kg) immediately after slaughter, sliced into cross-sections, and suspended in myograph chambers containing oxygenated Krebs-Henseleit buffer (95% O2/5% CO2; pH = 7.4; 37°C). Treatments were added at 0 min and buffer was replaced in 15-min intervals for a 120-min incubation. In addition to maximum tension and time to reach maximum tension, percent relaxation and rate of relaxation were determined following maximum tension for each treatment. All compounds tested produced significant contractile responses (P < 0.05). All ergoline alkaloids reached maximum response in less time (P < 0.05) than the remaining compounds and began to relax immediately after first buffer change. Lysergic acid had the greatest (P < 0.05) percent relaxation and ergonovine had the greatest (P < 0.05) rate of relaxation. The ergopeptine alkaloids ergovaline, ergotamine, ergocristine, ergocryptine, and ergocornine had slower developing contractile responses with a longer (P < 0.05) interval until maximum tension was achieved compared to the ergoline alkaloids. Maximal responses to all the ergopeptine alkaloids, however, all persisted for the 120-min duration with negligible relaxation occurring. The different classes of alkaloids differed greatly in the type of contractile response generated in the lateral saphenous vein. Persistence of contractile response is thought to be the primary contributing factor to the vasoconstriction observed in animals demonstrating signs of fescue toxicosis, where different ergot alkaloids can contribute differently. PMID:24492541

Pesqueira, A; Harmon, D L; Branco, A F; Klotz, J L

2014-03-01

370

A Dipolar Cycloaddition Approach Toward the Kopsifoline Alkaloid Framework  

PubMed Central

Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole ?-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton. PMID:17710185

Hong, Xuechuan; France, Stefan; Padwa, Albert

2007-01-01

371

Isopalhinine A, a unique pentacyclic Lycopodium alkaloid from Palhinhaea cernua.  

PubMed

A new pentacyclic (5/6/6/6/7) Lycopodium alkaloid named isopalhinine A (1), which possesses a sterically congested architecture built with a tricyclo[4.3.1.0(3,7)]decane (isotwistane) moiety and a 1-azabicyclo[4.3.1]decane moiety, and palhinines B (2) and C (3) were isolated from Palhinhaea cernua. The structure and absolute configuration of 1 were elucidated by a combination of NMR spectra, optical rotation calculation, and X-ray diffraction experiment. A possible biogenetic pathway was also proposed. PMID:23815071

Dong, Liao-Bin; Gao, Xiu; Liu, Fei; He, Juan; Wu, Xing-De; Li, Yan; Zhao, Qin-Shi

2013-07-19

372

Mass-spectrometry-directed analysis and purification of pyrrolizidine alkaloid cis/trans isomers in Gynura japonica.  

PubMed

Pyrrolizidine alkaloids are highly hepatotoxic natural chemicals that produce irreversible chronic and acute hepatotoxic effects on human beings. Purification of large amounts of pyrrolizidine alkaloids is necessary for toxicity studies. In this study, an efficient method for targeted analysis and purification of pyrrolizidine alkaloid cis/trans isomers from herbal materials was developed for the first time. Targeted analysis of the hepatotoxic pyrrolizidine alkaloids was performed by liquid chromatography with tandem mass spectrometry (precursor ion scan and daughter ion scan), and the purification of pyrrolizidine alkaloids was achieved with a mass-directed auto purification system. The extraction and preparative liquid chromatography conditions were optimized. The developed method was applied to analysis of Gynura japonica (Thunb.) Juel., a herbal medicine traditionally used for detumescence and relieving pain but is potentially hepatotoxic as it contains pyrrolizidine alkaloids. Twelve pyrrolizidine alkaloids (six cis/trans isomer pairs) were identified with reference compounds or characterized by liquid chromatography with tandem mass spectrometry, and five individual pyrrolizidine alkaloids, including (E)-seneciphylline, seneciphylline, integerrimine, senecionine, and seneciphyllinine, were prepared from G. japonica roots with high efficiency. The results of this work provide a new technique for the preparation of large amounts of pyrrolizidine alkaloid reference substances, which will also benefit toxicological studies of pyrrolizidine alkaloids and treatments for pyrrolizidine alkaloid-induced toxicity. PMID:24840731

Fang, Lianxiang; Xiong, Aizhen; Yang, Xiao; Cheng, Wenzhi; Yang, Li; Wang, Zhengtao

2014-08-01

373

Cytotoxic Alkaloids from the Whole Plants of Zephyranthes candida  

PubMed Central

Seven new alkaloids, N-methylhaemanthidine chloride (1), N-methyl-5,6-dihydroplicane (5), O-methylnerinine (6), N-ethoxycarbonylethylcrinasiadine (7), N-ethoxycarbonylpropylcrinasiadine (8), N-phenethylcrinasiadine (9) and N-isopentylcrinasiadine (10), together with eight known alkaloids, haemanthamin (2), 3-epimacronine (3), (+)-tazettine (4), N-methylcrinasiadine (11), trisphaeridine (12), 5,6-dihydrobicolorine (13), lycorine (14), and nigragillin (15), were isolated from the whole plants of Zephyranthes candida. The structures of the new compounds were established by spectroscopic data interpretation, with single-crystal X-ray diffraction analysis performed on 1. The absolute configuration of 3-epimacronine (3) was determined by single-crystal X-ray diffraction analysis with CuK? irradiation. Compounds 1–15 were evaluated for their in vitro cytotoxicity against five human cancer cell lines and the Beas-2B immortalized (non-cancerous) human bronchial epithelial cell line. Compounds 1, 2, 9, and 14 exhibited cytotoxicity with IC50 values ranging from 0.81 to 13 ?M with selectivity indices as high as 10 when compared to the Beas-2B cell line. PMID:23190013

Luo, Zengwei; Wang, Fuqian; Zhang, Jinwen; Li, Xingyao; Zhang, Mengke; Hao, Xincai; Xue, Yongbo; Li, Yan; Horgen, F. David; Yao, Guangmin; Zhang, Yonghui

2012-01-01

374

Biogeographical patterns and phenological changes in Lapiedra martinezii LAG. related to its alkaloid diversity.  

PubMed

The aim of this work was to investigate the alkaloid patterns of Lapiedra martinezii and their relation to biogeography and phenology focused in a phylogenetic comparison. Plants from 14 populations of L. martinezii, covering almost its entire distribution area, were subjected to morphological, ecological, and phytochemical analysis. Experiments for different alkaloid-type content are proposed as a new tool for analysis of plant distribution. Several plants were transplanted for weekly observation of their phenological changes, and alkaloids from different plant organs were extracted, listed, and compared. The alkaloid pattern of L. martinezii comprises 49?compounds of homolycorine, lycorine, tazettine, haemantamine, and narciclasine types. The populations located in the north and south margins of the distribution area displayed alkaloid patterns different from those of the central area. Changes in these patterns during their phenological cycle may be related to a better defence for plant reproduction. L. martinezii is an old relict plant, and it has maintained some of the more primitive morphological features and alkaloid profiles of the Mediterranean Amaryllidaceae. The variations in alkaloid content observed could be interpreted in a phylogenetic sense, and those found in their phenological changes, in an adaptive one. PMID:23847067

Ríos, Segundo; Berkov, Strahil; Martínez-Francés, Vanessa; Bastida, Jaume

2013-07-01

375

Effect of ergot alkaloids associated with fescue toxicosis on hepatic cytochrome P450 and antioxidant proteins  

SciTech Connect

Intake of ergot alkaloids found in endophyte-infected tall fescue grass is associated with decreased feed intake and reduction in body weight gain. The liver is one of the target organs of fescue toxicosis with upregulation of genes involved in xenobiotic metabolism and downregulation of genes associated with antioxidant pathways. It was hypothesized that short-term exposure of rats to ergot alkaloids would change hepatic cytochrome P450 (CYP) and antioxidant expression, as well as reduce antioxidant enzyme activity and hepatocellular proliferation rates. Hepatic gene expression of various CYPs, selected nuclear receptors associated with the CYP induction, and antioxidant enzymes were measured using real-time PCR. Hepatic expression of CYP, antioxidant and proliferating cell nuclear antigen (PCNA) proteins were measured using Western blots. The CYP3A1 protein expression was evaluated using primary rat hepatocellular cultures treated with ergovaline, one of the major ergot alkaloids produced by fescue endophyte, in order to assess the direct role of ergot alkaloids in CYP induction. The enzyme activities of selected antioxidants were assayed spectrophotometrically. While hepatic CYP and nuclear receptor expression were increased in ergot alkaloid-exposed rats, the expression and activity of antioxidant enzymes were reduced. This could potentially lead to increased oxidative stress, which might be responsible for the decrease in hepatocellular proliferation after ergot alkaloid exposure. This study demonstrated that even short-term exposure to ergot alkaloids can potentially induce hepatic oxidative stress which can contribute to the pathogenesis of fescue toxicosis.

Settivari, Raja S. [Division of Animal Science, University of Missouri, Columbia, MO 65211 (United States); Evans, Tim J. [Veterinary Diagnostic Laboratory, University of Missouri, Columbia, MO 65211 (United States); Rucker, Ed [Department of Veterinary Physiology and Pharmacology, Texas A and M University, College Station, TX77843 (United States); Rottinghaus, George E. [Veterinary Diagnostic Laboratory, University of Missouri, Columbia, MO 65211 (United States); Spiers, Donald E. [Division of Animal Science, University of Missouri, Columbia, MO 65211 (United States)], E-mail: spiersd@missouri.edu

2008-03-15

376

Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.  

PubMed

Clavines and D-lysergic acid-derived alkaloid amides and alkaloid peptides are two different families of compounds that have the indole-derived tetracyclic metergoline ring system in common. Previous work has shown that D-lysergic acid is biosynthetically derived from clavine alkaloids. Recent cloning and analysis of the ergot alkaloid biosynthesis gene cluster from the D-lysergic acid peptide (ergopeptines)-producing Claviceps purpurea, has shown that it most probably contains all genes necessary for D-lysergic acid synthesis as well as those that encode the assembly of D-lysergic acid peptides, such as ergotamine. To address the role of the oxygenase genes of alkaloid-gene clusters, the only cytochrome P450 monooxygenase gene of this cluster was inactivated by disruption. The resultant mutant accumulated agroclavine, elymoclavine, and chanoclavine in substantial amounts but not ergopeptines. Feeding the mutant with D-lysergic acid restored ergopeptine synthesis; this suggests a block in the conversion of elymoclavine to D-lysergic acid. The gene was designated cloA (for encoding a clavine oxidase, CLOA). Retransformation of the mutant with the intact cloA gene also restored ergopeptine synthesis. These data show that CLOA catalyses the conversion of clavines to D-lysergic acid, it acts as a critical enzyme in the ergot alkaloid gene cluster, and bridges the biosynthesis of the two different families of alkaloids. PMID:16538694

Haarmann, Thomas; Ortel, Ingo; Tudzynski, Paul; Keller, Ullrich

2006-04-01

377

Intraspecific alkaloid variation in ladybird eggs and its effects on con- and hetero-specific intraguild predators.  

PubMed

Egg predation and cannibalism are common phenomena in predatory ladybirds despite the presence of defensive alkaloids. Consumption of heterospecific eggs negatively affects survivorship and development; however, intraspecific variation in quantities of alkaloids and post-ingestion responses to con- and hetero-specific alkaloids, are not well understood. We examined variation in the quantity of alkaloids in eggs of Harmonia axyridis (Pallas), Coccinella septempunctata L., and Hippodamia convergens (Guérin) using gas chromatography-mass spectrometry, and show a link between heterospecific alkaloids and their toxicity and/or costs by feeding high and low alkaloid eggs to first instar H. axyridis and C. septempunctata. The repeatability of alkaloid measurements in eggs in an egg cluster was high; however, the amount of alkaloids varied significantly between egg clutches within and among females. This variation affected egg consumption by C. septempunctata when fed H. axyridis eggs. Harmonia axyridis accumulated their own alkaloid by cannibalism and synthesized it de novo, but C. septempunctata lost some portion of the consumed conspecific alkaloids. Both species lost most of the consumed heterospecific alkaloids, but C. septempunctata died within 3 days. Most H. axyridis survived to the second instar, but C. septempunctata alkaloids led to a significant reduction in weight gain compared to an aphid control. In addition, ingestion of high alkaloid C. septempunctata extended development of H. axyridis compared to the aphid control or conspecific eggs. Harmonia axyridis had greater abilities to process ingested con- and hetero-specific alkaloids compared with C. septempunctata, which may, in part, explain their interspecific interactions in nature. PMID:20049478

Kajita, Yukie; Obrycki, J J; Sloggett, J J; Haynes, K F

2010-06-01

378

Enhanced anti-tumour effects of Vinca alkaloids given separately from cytostatic therapies  

PubMed Central

Background and Purpose In polychemotherapy protocols, that is for treatment of neuroblastoma and Ewing sarcoma, Vinca alkaloids and cell cycle-arresting drugs are usually administered on the same day. Here we studied whether this combination enables the optimal antitumour effects of Vinca alkaloids to be manifested. Experimental Approach Vinca alkaloids were tested in a preclinical mouse model in vivo and in vitro in combination with cell cycle-arresting drugs. Signalling pathways were characterized using RNA interference. Key Results In vitro, knockdown of cyclins significantly inhibited vincristine-induced cell death indicating, in accordance with previous findings, Vinca alkaloids require active cell cycling and M-phase transition for induction of cell death. In contrast, anthracyclines, irradiation and dexamethasone arrested the cell cycle and acted like cytostatic drugs. The combination of Vinca alkaloids with cytostatic therapeutics resulted in diminished cell death in 31 of 36 (86%) tumour cell lines. In a preclinical tumour model, anthracyclines significantly inhibited the antitumour effect of Vinca alkaloids in vivo. Antitumour effects of Vinca alkaloids in the presence of cytostatic drugs were restored by caffeine, which maintained active cell cycling, or by knockdown of p53, which prevented drug-induced cell cycle arrest. Therapeutically most important, optimal antitumour effects were obtained in vivo upon separating the application of Vinca alkaloids from cytostatic therapeutics. Conclusion and Implications Clinical trials are required to prove whether Vinca alkaloids act more efficiently in cancer patients if they are applied uncoupled from cytostatic therapies. On a conceptual level, our data suggest the implementation of polychemotherapy protocols based on molecular mechanisms of drug–drug interactions. Linked Article This article is commented on by Solary, pp 1555–1557 of this issue. To view this commentary visit http://dx.doi.org/10.1111/bph.12101 PMID:23186127

Ehrhardt, H; Pannert, L; Pfeiffer, S; Wachter, F; Amtmann, E; Jeremias, I

2013-01-01

379

Diversity-oriented synthesis of Lycopodium alkaloids inspired by the hidden functional group pairing pattern.  

PubMed

Natural products continue to provide a rich source of inspiration for both chemists and biologists. The efficient synthesis of bioactive natural products or natural product-like molecules has offered tremendous opportunities for complex biological processes exploration and drug discovery. However, because natural products usually contain numerous stereogenic centres and polycyclic ring systems, significant synthetic challenges remain. Here we employ the build/couple/pair strategy that is frequently used in diversity-oriented synthesis to obtain skeletally diverse compounds with complexities comparable to natural products. Inspired by the functional group pairing patterns hidden in Lycopodium alkaloids, we efficiently and in parallel construct four natural products, (+)-Serratezomine A, (-)-Serratinine, (+)-8?-Hydroxyfawcettimine and (-)-Lycoposerramine-U, as well as six different unnatural scaffolds, following the advanced build/couple/pair algorithm. This newly developed strategy is expected to be applied to the efficient synthesis of other complex natural products possessing functional group pairing patterns as well as skeletally diverse natural product-like molecules. PMID:25082077

Zhang, Jing; Wu, Jinbao; Hong, Benke; Ai, Wenying; Wang, Xiaoming; Li, Houhua; Lei, Xiaoguang

2014-01-01

380

Isolation of teratogenic alkaloids by reversed-phase high-performance liquid chromatography.  

PubMed

Reversed-phase high-performance liquid chromatography was used for both analytical and preparative separations of several steroidal alkaloids which occur in extracts of Veratrum californicum. The inclusion of 0.1% trifluoroacetic acid in the mobile phase improved the efficiency of the chromatography and the solubility of the compounds in aqueous acetonitrile. Nuclear magnetic resonance was used to assist the identification of the isolated steroidal alkaloids. The effect of the interaction of trifluoroacetic acid with the alkaloids could be clearly seen by changes in the chemical shifts in the nuclear magnetic resonance spectra. PMID:6526920

Browne, C A; Sim, F R; Rae, I D; Keeler, R F

1984-12-01

381

Lycospidine A, a new type of Lycopodium alkaloid from Lycopodium complanatum.  

PubMed

Lycospidine A (1), the first example of a Lycopodium alkaloid which contains an unprecedented five-membered A ring, was isolated from Lycopodium complanatum. The unique five-membered A ring in 1 indicates that carbons 2-5 in 1 are presumably derived from proline instead of the lysine biosynthetically, which suggests that 1 represent a new class of Lycopodium alkaloid. In addition, the unique structural feature and biosynthetic origin of 1 shed new insight into the structural diversity of Lycopodium alkaloid analogue libraries potentially accessible by engineered biosynthesis. PMID:23647027

Cheng, Jin-Tang; Liu, Fei; Li, Xiao-Nian; Wu, Xing-De; Dong, Liao-Bin; Peng, Li-Yan; Huang, Sheng-Xiong; He, Juan; Zhao, Qin-Shi

2013-05-17

382

Unified total syntheses of fawcettimine class alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B.  

PubMed

The total syntheses of the lycopodium alkaloids fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B have been accomplished through an efficient, unified, and stereocontrolled strategy that relies on a Diels-Alder reaction to construct the cis-fused 6,5-carbocycles with one all-carbon quaternary center. Access to the enantioselective syntheses of both antipodes of those alkaloids can be achieved by kinetic resolution of the earliest intermediate via a Sharpless asymmetric dihydroxylation (Sharpless AD). Compared to existing approaches to these alkaloids, our synthetic route possesses superior stereocontrol over the C-4 and C-15 stereogenic centers as well as allowing for more functional variation on the 6-membered ring. PMID:22519642

Pan, Guojun; Williams, Robert M

2012-05-18

383

Alkaloids from Marine Invertebrates as Important Leads for Anticancer Drugs Discovery and Development.  

PubMed

The present review describes research on novel natural antitumor alkaloids isolated from marine invertebrates. The structure, origin, and confirmed cytotoxic activity of more than 130 novel alkaloids belonging to several structural families (indoles, pyrroles, pyrazines, quinolines, and pyridoacridines), together with some of their synthetic analogs, are illustrated. Recent discoveries concerning the current state of the potential and/or development of some of them as new drugs, as well as the current knowledge regarding their modes of action, are also summarized. A special emphasis is given to the role of marine invertebrate alkaloids as an important source of leads for anticancer drug discovery. PMID:25490431

Imperatore, Concetta; Aiello, Anna; D'Aniello, Filomena; Senese, Maria; Menna, Marialuisa

2014-01-01

384

A facile chemoenzymatic approach: one-step syntheses of monoterpenoid indole alkaloids.  

PubMed

Facile chemoenzymatic syntheses of cytotoxic monoterpenoid indole alkaloids with novel skeletons and multiple chiral centers are described. Synthesis of these alkaloids was achieved by a simple one-step reaction using strictosidine and 12-aza-strictosidine as the key intermediates. Strictosidines were prepared by coupling of secologanin with tryptamine and 7-aza-tryptamine, respectively, using the immobilized recombinant Rauvolfia strictosidine synthase. A detailed stereochemical analysis is presented herein. The results provide an opportunity for a chemoenzymatic approach that leads to an increased diversification of complex alkaloids with improved structures and activities. PMID:20872397

Zou, Hong-Bin; Zhu, Hua-Jian; Zhang, Liang; Yang, Liu-Qing; Yu, Yong-Ping; Stöckigt, Joachim

2010-11-01

385

Diterpene alkaloids from the roots of Aconitum moldavicum and assessment of Nav?1.2 sodium channel activity of aconitum alkaloids.  

PubMed

A new aconitane alkaloid, 1-O-demethylswatinine (1), was isolated from the root of Aconitum moldavicum together with the known compounds cammaconine (2), columbianine (3), swatinine (4), gigactonine (5), delcosine (6), lycoctonine (7), and ajacine (8). The structures were established by means of HRESIMS, 1D and 2D?NMR spectroscopy, including 1H-1H COSY, NOESY, HSQC, and HMBC experiments, resulting in complete 1H-NMR chemical shift assignments for 1-4. The effects of the isolated compounds 4-8, together with eighteen other Aconitum diterpene and norditerpene alkaloids with different skeletal types and substitution patterns, were studied on Nav?1.2 channels by the whole-cell patch clamp technique, using the QPatch-16 automated patch clamp system. Pyroaconitine, ajacine, septentriodine, and delectinine demonstrated significant Nav?1.2 channel inhibition (57-42?%) at 10?µM concentration; several other compounds (acovulparine, acotoxicine, hetisinone, 14-benzoylaconine-8-O-palmitate, aconitine, and lycoctonine) exerted moderate inhibitory activity (30-22?%), while the rest of the tested alkaloids were considered to be inactive. On the basis of these results and by exhaustive comparison of data of previously published computerized QSAR studies on diterpene alkaloids, certain conclusions on the structure-activity relationships of Aconitum alkaloids concerning Nav?1.2 channel inhibitory activity are proposed. PMID:24452459

Borcsa, Botond; Fodor, László; Csupor, Dezs?; Forgo, Peter; Molnár, Attila; Hohmann, Judit

2014-02-01

386

Capillary electrophoretic study of the synergistic biological effects of alkaloids from Chelidonium majus L. in normal and cancer cells.  

PubMed

In this study, the synergistic biological action of five celandine alkaloids in normal and cancer cells was investigated by capillary electrophoresis with light-emitting diode-induced native fluorescence detection. The specific capacity of each alkaloid to penetrate into the cells was estimated by monitoring alkaloid concentration decreases in the cell medium during incubation with murine fibroblast NIH/3T3, mouse melanoma B16F10, and human breast cancer MCF7 cell lines. Mixtures of isoquinoline alkaloids containing protopine, chelidonine, sanguinarine, allocryptopine, and stylopine were applied to cell cultures for 20 and 40 min, and the content of alkaloids in the cell media was measured by capillary electrophoresis (CE). CE separation of isoquinoline alkaloids was performed in 30 mM phosphate buffer (pH 2.5). As these alkaloids have native fluorescence, they were directly detected using the commercially available UV light-emitting diode without troublesome fluorescent derivatization. The results showed a differential ability of celandine alkaloids to penetrate into the normal and cancer cell interior, which was inversely proportional to their cytotoxic activity. While the most effective transport of celandine alkaloids from the cell medium to the cell interior was observed for normal murine fibroblast NIH/3T3 cells (about 55% of total content), cytotoxicity tests demonstrated selective and profound apoptotic effects of a five-alkaloid combination in the mouse melanoma B16F10 cell line. PMID:23358674

Kulp, Maria; Bragina, Olga

2013-04-01

387

Java Numerics  

NSDL National Science Digital Library

The JavaNumerics website "provides a focal point for information on numerical computing in Java." The project is headed by the Java Grande Forum Numerics Working Group, and sponsored by the Mathematical and Computational Sciences Division of the NIST Information Technology Laboratory. Reports, presentations and proposed APIs for numerical computing from the JavaNumerics working groups are posted here, along with links providing information on Java-related meetings, proposals, and benchmarks. Links to general numerics and linear algebra libraries, along with other tools and utilities, are also provided.

388

Independent recruitment of a flavin-dependent monooxygenase for safe accumulation of sequestered pyrrolizidine alkaloids in grasshoppers and moths.  

PubMed

Several insect lineages have developed diverse strategies to sequester toxic pyrrolizidine alkaloids from food-plants for their own defense. Here, we show that in two highly divergent insect taxa, the hemimetabolous grasshoppers and the holometabolous butterflies, an almost identical strategy evolved independently for safe accumulation of pyrrolizidine alkaloids. This strategy involves a pyrrolizidine alkaloid N-oxygenase that transfers the pyrrolizidine alkaloids to their respective N-oxide, enabling the insects to avoid high concentrations of toxic pyrrolizidine alkaloids in the hemolymph. We have identified a pyrrolizidine alkaloid N-oxygenase, which is a flavin-dependent monooxygenase, of the grasshopper Zonocerus variegatus. After heterologous expression in E. coli, this enzyme shows high specificity for pyrrolizidine alkaloids of various structural types and for the tropane alkaloid atropine as substrates, a property that has been described previously for a pyrrolizidine alkaloid N-oxygenase of the arctiid moth Grammia geneura. Phylogenetic analyses of insect flavin-dependent monooxygenase sequences suggest that independent gene duplication events preceded the establishment of this specific enzyme in the lineages of the grasshoppers and of arctiid moths. Two further flavin-dependent monooxygenase sequences have been identified from Z. variegatus sharing amino acid identities of approximately 78% to the pyrrolizidine alkaloid N-oxygenase. After heterologous expression, both enzymes are also able to catalyze the N-oxygenation of pyrrolizidine alkaloids, albeit with a 400-fold lower specific activity. With respect to the high sequence identity between the three Z. variegatus sequences this ability to N-oxygenize pyrrolizidine alkaloids is interpreted as a relict of a former bifunctional ancestor gene of which one of the gene copies optimized this activity for the specific adaptation to pyrrolizidine alkaloid containing food plants. PMID:22363737

Wang, Linzhu; Beuerle, Till; Timbilla, James; Ober, Dietrich

2012-01-01

389

Independent Recruitment of a Flavin-Dependent Monooxygenase for Safe Accumulation of Sequestered Pyrrolizidine Alkaloids in Grasshoppers and Moths  

PubMed Central

Several insect lineages have developed diverse strategies to sequester toxic pyrrolizidine alkaloids from food-plants for their own defense. Here, we show that in two highly divergent insect taxa, the hemimetabolous grasshoppers and the holometabolous butterflies, an almost identical strategy evolved independently for safe accumulation of pyrrolizidine alkaloids. This strategy involves a pyrrolizidine alkaloid N-oxygenase that transfers the pyrrolizidine alkaloids to their respective N-oxide, enabling the insects to avoid high concentrations of toxic pyrrolizidine alkaloids in the hemolymph. We have identified a pyrrolizidine alkaloid N-oxygenase, which is a flavin-dependent monooxygenase, of the grasshopper Zonocerus variegatus. After heterologous expression in E. coli, this enzyme shows high specificity for pyrrolizidine alkaloids of various structural types and for the tropane alkaloid atropine as substrates, a property that has been described previously for a pyrrolizidine alkaloid N-oxygenase of the arctiid moth Grammia geneura. Phylogenetic analyses of insect flavin-dependent monooxygenase sequences suggest that independent gene duplication events preceded the establishment of this specific enzyme in the lineages of the grasshoppers and of arctiid moths. Two further flavin-dependent monooxygenase sequences have been identified from Z. variegatus sharing amino acid identities of approximately 78% to the pyrrolizidine alkaloid N-oxygenase. After heterologous expression, both enzymes are also able to catalyze the N-oxygenation of pyrrolizidine alkaloids, albeit with a 400-fold lower specific activity. With respect to the high sequence identity between the three Z. variegatus sequences this ability to N-oxygenize pyrrolizidine alkaloids is interpreted as a relict of a former bifunctional ancestor gene of which one of the gene copies optimized this activity for the specific adaptation to pyrrolizidine alkaloid containing food plants. PMID:22363737

Wang, Linzhu; Beuerle, Till; Timbilla, James; Ober, Dietrich

2012-01-01

390

Pyrroloacridine Alkaloids from Plakortis quasiamphiaster: Structures and Bioactivity  

PubMed Central

A re-collection of Plakortis quasiamphiaster from Vanuatu in 2003 resulted in the isolation of three known compounds, plakinidine A (1) and amphiasterins B1 (6) and B2 (7). Also isolated was a new bis-oxygenated pyrroloacridine alkaloid, plakinidine E (8), with a unique O-substitution versus N-substitution at position C-12 in 1. The biological evaluation of the active compounds in two assays provided complementary data. Plakinidine A (1) exhibited cytotoxicity against human colon H-116 cells with an IC50 of 0.23 ?g/mL, but there were no effects against the yeast Saccharomyces cerevisiae diploid homozygous deletion strain of topoisomerase I (top1?). By contrast, 8 was inactive against H-116 cells but was potent in the yeast halo screen. PMID:17253856

Ralifo, Paul; Sanchez, Laura; Gassner, Nadine C.; Tenney, Karen; Lokey, R. Scott; Holman, Theodore R.; Valeriote, Frederick A.; Crews, Phillip

2007-01-01

391

Indolosesquiterpene alkaloids from the Cameroonian medicinal plant Polyalthia oliveri (Annonaceae).  

PubMed

The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8?-polyveolinone (1), N-acetyl-8?-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line. PMID:25039009

Kouam, Simeon Fogue; Ngouonpe, Alain Wembe; Lamshöft, Marc; Talontsi, Ferdinand Mouafo; Bauer, Jonathan O; Strohmann, Carsten; Ngadjui, Bonaventure Tchaleu; Laatsch, Hartmut; Spiteller, Michael

2014-09-01

392

Reviewing Colchicaceae alkaloids - perspectives of evolution on medicinal chemistry.  

PubMed

The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways. PMID:24359194

Larsson, Sonny; Rønsted, Nina

2014-01-01

393

Molecular recognition pattern of cytotoxic alkaloid vinblastine with multiple targets.  

PubMed

Vinblastine (VLB), a cytotoxic alkaloid is used extensively against various cancer types and the crystal structure of its tubulin complex is already known. Multitarget affinity of vinblastine has been investigated and the nature of binding with biological receptors namely, duplex DNA and Human serum albumin (HSA) has been compared to the binding characteristics of its known complex with natural high affinity receptor tubulin using molecular docking and QM-MM calculations. VLB is found to interact with DNA as well as HSA protein, though, with weaker affinity as compared to tubulin. Analysis of various docked complexes revealed that the H-bonds and cation-pi bonds do not have significant contribution to the binding interactions and despite its large size, VLB remains in relaxed conformation and fits in the hydrophobic regions on the receptors. PMID:25241127

Pandya, Prateek; Agarwal, Lokesh Kr; Gupta, Neelima; Pal, Sourav

2014-11-01

394

Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry  

PubMed Central

The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways. PMID:24359194

Larsson, Sonny; Rønsted, Nina

2014-01-01

395

New alkaloids from Aconitum taipaicum and their cytotoxic activities.  

PubMed

Three new aconitine-type C19-diterpenoid alkaloids, taipeinines A-C (1-3), were isolated from the roots of Aconitum taipaicum. The chemical structures of these three compounds were established as (1?,6?,8?,14?,16?)-20-ethyl-8,14-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-aconitane (1), (1?,6?,8?,14?,16?)-20-ethyl-8,14-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-aconitane (2) and (1?,6?,8?,14?,16?)-20-ethyl-1,8,14-trihydroxy-6,16-dimethoxy-4-(methoxymethyl)-aconitane (3), respectively, on the basis of spectroscopic analyses, mainly MS, 1D and 2D NMR. The cytotoxic activities of these compounds were also assayed, and the results were quite impressive. PMID:24289160

Guo, Zeng-Jun; Xu, Ying; Zhang, Hui; Li, Meng-Yi; Xi, Ke

2014-01-01

396

Biomimetic synthesis and studies toward enantioselective synthesis of flindersial alkaloids.  

PubMed

A strategy allowing both stereocontrol and control over structural isomer formation has been defined for the antimalarial flindersial alkaloids. The recently reported flinderoles were demonstrated to be derived from the natural product borrerine. The structural isomers of flinderoles, the borreverines, were also produced in vitro along with the flinderoles through the dimerization of borrerine in acidic conditions. This result is thought to replicate the biosynthesis of these compounds. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine can each be synthesized in three steps from tryptamine. Furthermore, progress toward a concise enantioselective synthesis of flinderoles A, B, and C is described. This work includes enantioselective conjugate addition to an unprotected indole-appended enone. Chirality 27:14-17, 2015. © 2013 Wiley Periodicals, Inc. PMID:23529894

Vallakati, Ravikrishna; Lundy, Brian J; Jansone-Popova, Santa; May, Jeremy A

2015-01-01

397

Vitiquinolone--a quinolone alkaloid from Hibiscus vitifolius Linn.  

PubMed

Phytochemical investigations of the powdered root of Hibiscus vitifolius Linn. (Malvaceae) was extracted successively with n-hexane and chloroform. Analysis of the n-hexane extract by GC-MS led to the identification of twenty-six components by comparison of their mass spectra with GC-MS library data. A novel quinolone alkaloid, vitiquinolone (5) together with eight known compounds viz. ?-Amyrin acetate (1), n-octacosanol (2), ?-Amyrin (3), stigmasterol (4), xanthyletin (6), alloxanthoxyletin (7), xanthoxyletin (8) and betulinic acid (9) were isolated from chloroform extract by column chromatography over silica gel. The structure of vitiquinolone was established on the basis of spectroscopic methods including UV, IR, 1D, 2D NMR and ESI-MS. The known compounds were identified on the basis of their physical and spectroscopic data as reported in the literature. PMID:24128571

Ramasamy, D; Saraswathy, A

2014-02-15

398

Two new alkaloids from Portulaca oleracea and their cytotoxic activities.  

PubMed

Two new alkaloids named (3R)-3,5-bis(3-methoxy-4-hydroxyphenyl)-2,3-dihydro-2(1H)-pyridinone (1) and 1,5-dimethyl-6-phenyl-1,2-dihydro-1,2,4-triazin-3(2H)-one (2), together with two known compounds (7'R)-N-feruloyl normetanephrine (3) and N-trans-feruloyl tyramine (4) were isolated from the air-dried aerial parts of Portulaca oleracea L. Their structures and configurations were elucidated by spectroscopic methods including 1D NMR, 2D NMR, and HR-MS techniques. In addition, compounds 1-4 were tested for in vitro cytotoxic activities against human lung (K562 and A549) and breast (MCF-7 and MDA-MB-435) cancer cell lines. PMID:24321009

Tian, Jin-Long; Liang, Xiao; Gao, Pin-Yi; Li, Dan-Qi; Sun, Qian; Li, Ling-Zhi; Song, Shao-Jiang

2014-01-01

399

Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia.  

PubMed

A new aporphine, N-(N-methylcarbamoyl)-O-methyl-bulbocapnine (1), together with seven known compounds, (-)-5'-methoxypodorhizol (2), a mixture of beta-sitosterone (3) and stigmasta-4,22-dien-3-one (4), a mixture of 3 beta-hydroxystigmast-5-en-7-one (5) and 3 beta-hydroxystigmasta-5,22-dien-7-one (6), and a mixture of 6 alpha-hydroxystigmast-4-en-3-one (7) and 6 alpha-hydroxystigmasta-4,22-dien-3-one (8), were isolated in continuing studies on the trunk bark of Formosan Hernandia nymphaeifolia. The structures of these compounds were determined through spectral analyses. In addition, the previously reported six alkaloids, laurotetanine, oxohernagine, thalicarpine, reticuline, (+)-vateamine-2'-beta-N-oxide, (+)-hernandaline and six lignans, (+)-epiaschantin, (+)-epimagnolin, (+)-epiyangambin, (-)-hernone, (-)-yatein, (-)-deoxypodophyllotoxin were demonstrated to have anti-platelet aggregation activity. PMID:10821052

Chen, J J; Chang, Y L; Teng, C M; Chen, I S

2000-04-01

400

Antitrypanosomal quinoline alkaloids from the roots of Waltheria indica.  

PubMed

Chemical investigation of the dichloromethane root extract of Waltheria indica led to the isolation and characterization of 10 quinoline alkaloids, namely, 8-deoxoantidesmone (1), waltheriones E-L (2-9), and antidesmone (10). Among these, compounds 2-9 have not yet been described in the literature. Their chemical structures were established by means of spectroscopic data interpretation including (1)H and (13)C NMR, HSQC, HMBC, COSY, and NOESY experiments and UV, IR, and HRESIMS. The absolute configurations of the compounds were established by comparison of experimental and TDDFT-calculated ECD spectra. In addition, the isolated constituents were evaluated for their in vitro antitrypanosomal activity. Compounds 4, 5, and 8 showed potent and selective growth inhibition toward Trypanosoma cruzi with IC50 values between 0.02 and 0.04 ?M. Cytotoxicity for mouse skeletal L-6 cells was also determined for these compounds. PMID:25314007

Cretton, Sylvian; Breant, Lise; Pourrez, Lucie; Ambuehl, Chiara; Marcourt, Laurence; Ebrahimi, Samad Nejad; Hamburger, Matthias; Perozzo, Remo; Karimou, Soumana; Kaiser, Marcel; Cuendet, Muriel; Christen, Philippe

2014-10-24

401

Determination of pyrrolizidine alkaloids in tea, herbal drugs and honey.  

PubMed

Honey was previously considered to be one of the main food sources of human pyrrolizidine alkaloid (PA) exposure in Europe. However, comprehensive analyses of honey and tea sampled in the Berlin retail market revealed unexpected high PA amounts in teas. This study comprised the analysis of 87 honey as well as 274 tea samples including black, green, rooibos, melissa, peppermint, chamomile, fennel, nettle, and mixed herbal tea or fruit tea. Total PA concentrations in tea ranged from < LOD to 5647 µg kg(-1), while a mean value of about 10 µg kg(-1) was found in honey samples. Additionally, herbal drugs were investigated to identify the source of PA in teas. Results suggest that PA in tea samples are most likely a contamination caused by co-harvesting of PA-producing plants. In some cases such as fennel, anise or caraway, it cannot be excluded that these plants are able to produce PA themselves. PMID:25222912

Bodi, Dorina; Ronczka, Stefan; Gottschalk, Christoph; Behr, Nastassja; Skibba, Anne; Wagner, Matthias; Lahrssen-Wiederholt, Monika; Preiss-Weigert, Angelika; These, Anja

2014-11-01

402

Expression of Veratrum alkaloid teratogenicity in the mouse.  

PubMed

Jervine, a steroidal alkaloid found as a minor constituent in the teratogenic range plant Veratrum californicum, has produced similar terata in sheep, rabbit, hamster, and chick, although the sensitivity to the alkaloid varies in the different species. Sprague Dawley rats and Swiss Webster mice are relatively insensitive. The aim of this study was to determine the teratogenic potential of jervine in three strains of mice and to ascertain if the response is strain dependent. One strain, Swiss N:GP(S), was retested since a Swiss Webster strain had been found previously to be jervine-resistant. In addition, we tested C57BL/6J and A/J, which are known to differ in their response to the teratogenic action of steroids and vitamin A. Mice were treated by gavage with single doses of jervine (70, 150, or 300 mg/kg body weight) on either day 8, 9, or 10 of gestation. Jervine was teratogenic to C57BL/6J and A/J mice but not to N:GP(S). The induced terata included cleft lip with or without cleft palate, isolated cleft palate, mandibular micrognathia or agnathia, and limb malformations. Fetal teratogenicity and maternal and fetal toxicity were highly correlated. The prevalence of each defect and fetal death was a function of strain, dose, and time of treatment. Maternal death was higher in C57BL/6J than in A/J mice. Although some of the terata were similar, the response pattern between strains was different from corticosteroids and vitamin A for both sensitive period and the strain dose response. An effect on differentiation of chondrocyte precursors may account for many of the defects, but an earlier lethal effect on differentiation of neural crest cells or precordal mesenchyme may also occur. PMID:2218940

Omnell, M L; Sim, F R; Keeler, R F; Harne, L C; Brown, K S

1990-08-01

403

Mw Systematic Study of Alkaloids: the Distorted Tropane of Scopoline  

NASA Astrophysics Data System (ADS)

Tropane alkaloids have diverse pharmacological uses and are well-known for their neurostimulant activity. Previous structure-activity-relationship established correlations between bioactivity and several aspects of ligand conformation and stereochemistry, including delicate intramolecular effects like nitrogen inversion^{a}. We have initiated a series of structural studies on tropane alkaloids^{b}, aimed to discerning their intrinsic stereochemical properties using rotational spectroscopy in supersonic jets^{c}. Here we extend these studies to the epoxytropanes, initially motivated to interrogate the influence of the epoxy group on nitrogen inversion and ring conformation. The rotational spectrum evidences a single structure in the gas phase, providing a first description of the (three ring) structurally-distorted tropane in scopoline. The determined rotational parameters of scopoline reveal the structural consequences of the intramolecular cyclation of scopine, which breaks the original epoxy group and creates a new ether bridge and a 7?-hydroxytropane configuration. The hydroxyl group further stabilizes the molecule by an O-H \\cdots N intramolecular hydrogen bond, which, in turn, forces the N-methyl group to the less stable axial form^{b}. The experimental work was supported by ab initio and DFT calculations. ^{a} i) S.Singh, Chem. Rev. 100, 925 (2000); ii) A. Krunic, D. Pan, W.J. Dunn III, S.V.S. Miariappan, Bioorg. & Med. Chem. 17, 811 (2009). ^{b} E.J. Cocinero, A. Lesarri, P. écija, J.-U. Grabow, J.A. Fernández, F. Castaño, Phys. Chem. Chem. Phys. 12, 6076 (2010). ^{c} E.J. Cocinero, A. Lesarri, P. écija, J.-U. Grabow, J.A. Fernández, F. Castaño, Phys. Chem. Chem. Phys. 12, 12486 (2010).

Ecija, Patricia; Cocinero, Emilio J.; Basterretxea, Francisco J.; Fernandez, Jose A.; Castano, Fernando; Lesarri, Alberto

2013-06-01

404

A multi-omics strategy resolves the elusive nature of alkaloids in Podophyllum species.  

PubMed

Podophyllum hexandrum and, to a much lesser extent P. peltatum, are sources of podophyllotoxin, extensively used as a chemical scaffold for various anti-cancer drugs. In this study, integrated omics technologies (including advanced mass spectrometry/metabolomics, transcriptome sequencing/gene assemblies, and bioinformatics) gave unequivocal evidence that both plant species possess a hitherto unknown aporphine alkaloid metabolic pathway. Specifically, RNA-seq transcriptome sequencing and bioinformatics guided gene assemblies/analyses in silico suggested presence of transcripts homologous to genes encoding all known steps in aporphine alkaloid biosynthesis. A comprehensive metabolomics analysis, including UPLC-TOF-MS and MALDI-MS imaging in situ, then enabled detection, identification, localization and quantification of the aporphine alkaloids, magnoflorine, corytuberine and muricinine, in the underground and aerial tissues. Interestingly, the purported presence of alkaloids in Podophyllum species has been enigmatic since the 19th century, remaining unresolved until now. The evolutionary and phylogenetic ramifications of this discovery are discussed. PMID:25166004

Marques, Joaquim V; Dalisay, Doralyn S; Yang, Hong; Lee, Choonseok; Davin, Laurence B; Lewis, Norman G

2014-11-01

405

Formal Total Synthesis of the Cytotoxic Marine Ascidian Alkaloid Haouamine A  

PubMed Central

Described is a convergent 13-step synthesis of a pentacyclic compound which has previously been transformed into haouamine A, therefore constituting a formal total synthesis of this unique marine alkaloid. PMID:16706513

Jeong, Jeannie H.; Weinreb, Steven M.

2008-01-01

406

Berbanine: a new isoquinoline-isoquinolone alkaloid from Berberis vulgaris (Berberidaceae).  

PubMed

A new isoquinoline-isoquinolone alkaloid was isolated from the root bark of Berberis vulgaris and named berbanine. The structure was established by spectroscopic methods (including 2D NMR, HR-EI-MS). PMID:23738447

Host'álková, Anna; Novák, Zdenek; Pour, Milan; Jirosová, Anna; Opletal, Lubomír; Kunes, Jirí; Cahliková, Lucie

2013-04-01

407

Recent Progress in the Metabolic Engineering of Alkaloids in Plant Systems  

PubMed Central

Plant alkaloids have a rich chemical ecology that has been exploited for medicinal purposes for thousands of years. Despite being highly represented within today’s pharmacopoeia, relatively little is known about the biosynthesis, regulation and transport of these molecules. Understanding how nature synthesizes plant alkaloids will enhance our ability to overproduce—that is, to metabolically engineer—these medicinally useful compounds as well as new-to-nature compounds (with potentially improved bioactivity) derived from these natural scaffolds. Recent progress in the metabolic engineering of nitrogen-containing plant natural products—specifically the monoterpene indole alkaloids, the benzylisoquinoline alkaloids and the glucosinolates—was made possible through the characterization of various components in both native and engineered enzymatic pathways. The subsequent reconfiguration and tuning of these biological “parts” has enabled the production of selected products at increasingly higher titers. PMID:22954587

Glenn, Weslee S.; Runguphan, Weerawat; O’Connor, Sarah E.

2012-01-01

408

Asymmetric Construction of Rings A–D of Daphnicyclidin Type Alkaloids  

PubMed Central

The aza-Cope–Mannich reaction and ring-closing metathesis are key steps in the assembly of intermediates containing rings A–D of Daphniphyllum alkaloids of the daphnicyclidin-type such as daphnipaxinin and oldhamine A. PMID:19904991

Dunn, Travis B.; Ellis, J. Michael; Kofink, Christiane C.; Manning, James R.; Overman, Larry E.

2010-01-01

409

Alkaloids from the bulbs of Lycoris longituba and their neuroprotective and acetylcholinesterase inhibitory activities.  

PubMed

Three novel alkaloids (1-3), together with nineteen known ones (4-22), were isolated from the bulbs of Lycoris longituba. Their structures were elucidated on the basis of extensive spectroscopic analyses, which belong to several Amaryllidaceae alkaloid skeletons. Among them, the harmane-type alkaloids (the new compound 1 and the known compounds 5, 6 and 7) were found for the first time from Lycoris genus. The isolates were tested for their neuroprotective activities against CoCl2, H2O2 and A?25-35-induced SH-SY5Y cell injuries, and the majority of them exhibited neuroprotective activities of different degrees. The acetylcholinesterase (AChE) inhibitory activities of the isolated alkaloids were also evaluated, while compounds 12, 14-20 and 22 exhibited extremely significant AChE inhibitory activities. PMID:25219454

Zhu, Yun-Yun; Li, Xue; Yu, Heng-Yi; Xiong, Yu-Fang; Zhang, Peng; Pi, Hui-Fang; Ruan, Han-Li

2014-09-16

410

Lycopladine A, a new C 16N alkaloid from Lycopodium complanatum  

Microsoft Academic Search

A new C16N type alkaloid, lycopladine A (1), has been isolated from the club moss Lycopodium complanatum, and the structure and relative stereochemistry of 1 were elucidated on the basis of spectral data.

Kan’ichiro Ishiuchi; Takaaki Kubota; Hiroshi Morita; Jun’ichi Kobayashi

2006-01-01

411

A journey under the sea: the quest for marine anti-cancer alkaloids.  

PubMed

The alarming increase in the global cancer death toll has fueled the quest for new effective anti-tumor drugs thorough biological screening of both terrestrial and marine organisms. Several plant-derived alkaloids are leading drugs in the treatment of different types of cancer and many are now being tested in various phases of clinical trials. Recently, marine-derived alkaloids, isolated from aquatic fungi, cyanobacteria, sponges, algae, and tunicates, have been found to also exhibit various anti-cancer activities including anti-angiogenic, anti-proliferative, inhibition of topoisomerase activities and tubulin polymerization, and induction of apoptosis and cytotoxicity. Two tunicate-derived alkaloids, aplidin and trabectedin, offer promising drug profiles, and are currently in phase II clinical trials against several solid and hematologic tumors. This review sheds light on the rich array of anti-cancer alkaloids in the marine ecosystem and introduces the most investigated compounds and their mechanisms of action. PMID:22113577

Tohme, Rita; Darwiche, Nadine; Gali-Muhtasib, Hala

2011-01-01

412

Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids  

PubMed Central

Wild Syrian rue (Peganum harmala L. family Zygophyllaceae) is well-known in Iran and various parts of this plant including, its seeds, bark, and root have been used as folk medicine. Recent years of research has demonstrated different pharmacological and therapeutic effects of P. harmala and its active alkaloids, especially harmine and harmaline. Analytical studies on the chemical composition of the plant show that the most important constituents of this plant are beta-carboline alkaloids such as harmalol, harmaline, and harmine. Harmine is the most studied among these naturally occurring alkaloids. In addition to P. harmala (Syrian rue), these beta-carbolines are present in many other plants such as Banisteria caapi and are used for the treatment of different diseases. This article reviews the traditional uses and pharmacological effects of total extract and individual active alkaloids of P. harmala (Syrian rue). PMID:24347928

Moloudizargari, Milad; Mikaili, Peyman; Aghajanshakeri, Shahin; Asghari, Mohammad Hossein; Shayegh, Jalal

2013-01-01

413

Facilitating Biomimetic Syntheses of Borrerine Derived Alkaloids by Means of Flow-Chemical Methods  

E-print Network

Flow chemistry, although now commonly used for general synthetic chemistry, has not been applied extensively in a biomimetic fashion. Here we show how the flow syntheses of borrerine derived alkaloids can use these principles to obtain complex...

Kamptmann, Sonja B.; Ley, Steven V.

2014-01-01

414

Dimerization of functional pyrroloindolizines for the synthesis of complex myrmicarin alkaloids  

E-print Network

The union of functionalized pyrroloindolizines for the synthesis of heterodimeric products relevant to myrmicarin alkaloids is described. Design and synthesis of tricyclic substrates and new methods for their union enable ...

Ondrus, Alison E.

415

Tetrahydroisoquinoline Alkaloids: in vivo Metabolites of L-Dopa in Man  

Microsoft Academic Search

Tetrahydroisoquinoline alkaloids have been unequivocally demonstrated in vivo for the first time in parkinsonian patients on L-dopa treatment. Their biosynthesis may have a profound bearing on how L-dopa acts.

M. Sandler; Susan Bonham Carter; K. R. HUNTER; G. M. STERN

1973-01-01

416

Asexual endophytes in a native grass: Tradeoffs in mortality, growth, reproduction, and alkaloid production  

Technology Transfer Automated Retrieval System (TEKTRAN)

Neotyphodium endophytes are asexual, seed-borne fungal symbionts that are thought to interact mutualistically with their grass hosts. Benefits include increased growth, reproduction, and resistance of herbivores via endophytic alkaloids. Although these benefits are well established in infected int...

417

Investigation of the metabolism of ergot alkaloids in cell culture by fourier transformation mass spectrometry.  

PubMed

Ergot alkaloids are known toxic secondary metabolites of the fungus Claviceps purpurea occurring in various grains, especially rye products. The liver is responsible for converting the ergot alkaloids into metabolites; however, the toxic impact of these end products of metabolism is still unknown. The aim of this study was to analyze the metabolism of ergot alkaloids in colon and liver cell lines (HT-29, HepG2), as well as in human primary renal cells (RPTEC). It was shown that cells in vitro are able to metabolize ergot alkaloids, forming a variety of metabolic compounds. Significant differences between the used cell types could be identified, and a suitable model system was established using HT-29 cells, performing an intensive metabolism to hydroxylated metabolites. The formed substances were analyzed by coupling of high-performance liquid chromatography with fluorescence detection and Fourier transformation mass spectrometry (HPLC-FLD-FTMS) as a powerful tool to identify known and unknown metabolites. PMID:21650459

Mulac, Dennis; Grote, Anna-Karina; Kleigrewe, Karin; Humpf, Hans-Ulrich

2011-07-27

418

A New Indole Alkaloid Glycoside from the Leaves of Palicourea marcgravii.  

PubMed

A new indole alkaloid glucoside, named palicoside, has been isolated from the leaves of PALICOUREA MARCGRAVII (Rubiaceae) collected in Brazil. The structure was established by spectroscopic methods and its chemical conversion to strictosamide. PMID:17262418

Morita, H; Ichihara, Y; Takeya, K; Watanabe, K; Itokawa, H; Motidome, M

1989-06-01

419

Inhibition of mammalian and oncornavirus nucleic acid polymerase activities by alkoxybenzophenanthridine alkaloids.  

PubMed

The alkoxybenzophenanthridine alkaloids (coralyne acetosulfate, fagaronine chloride, and nitidine chloride) have been reported to possess antileukemic activity in mice. These compounds were tested for inhibition of reverse transcriptase activity of an RNA tumor virus and DNA polymerase, RNA polymerase, and polyadenylic acid polymerase activities of NIH-Swiss mouse embryos. Reverse transcriptase and DNA polymerase activities were strongly inhibited by these antileukemic alkaloids, whereas RNA polymerase and polyadenylic acid polymerase activities were only moderately affected. Viral and cellular DNA polymerase activities were potently diminished by the alkaloids when poly[d(A-T)], poly(dA)-oligo(dT), and poly(rA)-oligo(dT) template primers were used in the reaction mixture; however, no inhibition of enzyme activity was obtained with poly(rC)-oligo(dG) as template primer. These results suggest that alkoxybenzophenanthridine alkaloids inhibit DNA polymerase activity by interaction with A:T base pairs of the template primer. PMID:58719

Sethi, V S

1976-07-01

420

The effects of methyllycaconitine on the response of TE-671 cells to acetylcholine and epibatidine  

Technology Transfer Automated Retrieval System (TEKTRAN)

Methyllycaconitine (MLA) is a norditerpenoid alkaloid found in Delphinium spp., and is a potent and selective antagonist of a7-nicotinic acetylcholine receptors. Plants with high concentrations of MLA are responsible for many livestock poisonings in the Intermountain West of the United States of Am...

421

Distribution of Delphinium occidentale chemotypes and their potential toxicity  

Technology Transfer Automated Retrieval System (TEKTRAN)

Larkspurs (Delphinium spp.) are poisonous plants found on rangelands in Western North America. Larkspur’s toxicity has been attributed to the norditerpenoid alkaloids which are divided into two main structural groups; the highly toxic (N-methylsuccinimido) anthranoyllycoctonine type (MSAL-type) and...

422

Patterns of indole alkaloids synthesis in response to heat shock, 5-azacytidine and Na-butyrate treatment of cultured catharanthus roseus mesophyll protoplasts  

SciTech Connect

Alkaloids of C. roseus are in high demand for therapeutic and other reasons. Cultured Catharanthus cells can produce limited quantities of these alkaloids. The authors have found that cultured mesophyll protoplasts in the presence of /sup 14/C-Tryptamine are capable of synthesizing alkaloids. The pattern of alkaloids synthesis changes when protoplasts are subjected to a heat shock at 37/sup 0/C. The heat shocked protoplasts incorporated 33% more /sup 14/C-Tryptamine and produced 3 new types of alkaloids. Treatment of protoplasts with 5-azacytidine, a DNA hypomethylating agent and Na-butyrate which induces hyperacetylation of histones produced qualitative and quantitative changes in the alkaloid pattern. Four new alkaloids following the above treatments were detected by TLC and HPLC of the extracts. It is suggested that the alkaloid pattern of the cultured protoplasts can be altered by treatment with compounds known as regulators of gene expression. Work is in progress to isolate and identify these new alkaloids.

Saleem, M.; Cutler, A.J.

1986-04-01

423

Metabolism of purine bases, nucleosides and alkaloids in theobromine-forming Theobroma cacao leaves  

Microsoft Academic Search

We examined the purine alkaloid content and purine metabolism in cacao (Theobroma cacao L.) plant leaves at various ages: young small leaves (stage I), developing intermediate size leaves (stage II), fully developed leaves (stage III) from flush shoots, and aged leaves (stage IV) from 1-year-old shoots. The major purine alkaloid in stage I leaves was theobromine (4.5 ?mol g–1 fresh weight),

Yoko Koyama; Yoshihisa Tomoda; Misako Kato; Hiroshi Ashihara

2003-01-01

424

Cytochemical Localization of Polysaccharides in Claviceps paspali Ultrastructure During Submerged Fermentation of Alkaloids  

PubMed Central

Morphological characteristics of two types of elements in the submerged mycelium of Claviceps paspali are described. Distribution of polysaccharides in the cell wall and cytoplasm was cytochemically determined at the ultrastructural level. Polysaccharide deposition into the cell walls was proportional to the increase in the alkaloid yield. In the cytoplasm, on the other hand, the presence of polysaccharide grains indicated an absence of alkaloid synthesis. Images PMID:4362461

Vo?íšek, J.; Ludvík, J.; ?ehá?ek, Z.

1974-01-01

425

Dihydropyrrolizine attractants for arctiid moths that visit plants containing pyrrolizidine alkaloids  

Microsoft Academic Search

Adults of three species of arctiid moths (Cisseps fulvicollis, Ctenucha virginia, andHalysidota tessellaris) are attracted to plants that contain pyrrolizidine alkaloids (PAs). The moths use olfactory cues to locate these plants, then feed on leaves, flowers, and roots with the proboscis. To investigate the chemical basis of attraction, sticky traps were baited with roots of a PA-containing plant,Eupatorium maculatum, alkaloids

Stuart B. Krasnoff; David E. Dussourd

1989-01-01

426

Recent advances in cinchona alkaloid catalysis for enantioselective carbon-nitrogen bond formation reactions.  

PubMed

Organocatalysis and cooperative catalysis are fast growing research areas. In these fields, cinchona alkaloids and their derivatives play a major role. The ready availability of both pseudo-enantiomeric pairs from natural sources makes them outstanding catalysts for reactions including oxidation, alkylation, cycloaddition, and carbene insertion. This short review focuses on recent achievements in the field of asymmetric carbon-nitrogen atom bond formation reactions using cinchona alkaloids and their derivatives. PMID:24359199

Saito, Hiroaki; Miyairi, Shinichi

2014-01-01

427

Factors affecting total alkaloid and nitrate levels in pearl millet (Pennisetum americanum (L.) Leeke)  

E-print Network

for the degree of MASTER OF SCIENCE December 1981 Major Subject: Agronomy FACTORS AFFECTING TOTAL ALKALOID AND NITRATE LEVELS IN PEARL MILLET (PENNISETUM AMERICANUM (L. ) LEEKE) A Thesis by BEVERLY BLOHOWIAK KREJSA Approved as to style and content by...: (Co-chairman of Committee) ( o-chsi an Committee) J (Member) C~?. (Member) Head of e ment) y" December 1981 ABSTRACT Factors Affecting Total Alkaloid and Nitrate Levels in Pearl Millet (P' t *(L)Lk) Beverly Blohowiak Krejsa, B. S. , Texas A...

Krejsa, Beverly Blohowiak

1981-01-01

428

Stereochemical inversion of pyrrolizidine alkaloids by Mechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance  

Microsoft Academic Search

Pyrrolizidine alkaloids (PAs), acquired by adults or larvae of Danainae and Ithomiinae butterflies and Arctiidae moths from plants, protect these lepidopterans against predators and are biosynthetic precursors of male sex pheromones. The investigation of PAs in many species of wild-caught adults of Ithomiinae showed lycopsamine (1) [(7R)-OH, (2?S)-OH, (3?S)-OH] as the main alkaloid. In incorporation experiments, PA-free (freshly emerged) adults

José Roberto Trigo; Lauro Euclides Soares Barata; Keith S. Brown

1994-01-01

429

Antitrypanosomal alkaloids from Polyalthia suaveolens (Annonaceae): Their effects on three selected glycolytic enzymes of Trypanosoma brucei  

Microsoft Academic Search

In continuation of our study on medicinal plants of Cameroon, stem barks of Polyalthia suaveolens were phytochemically studied. This investigation yielded a new indolosesquiterpene alkaloid, named polysin (1) and four hitherto known alkaloids (2–5). Polysin (1) appeared as a competitive reversible inhibitor (Ki=10?M) of phosphofructo kinase (PFK) of Trypanosoma brucei with respect to fructose-6-phosphate (Ki\\/KM=0.05) and could be used in

Igor Ngantchou; Barthélemy Nyasse; Colette Denier; Casimir Blonski; Véronique Hannaert; Bernd Schneider

2010-01-01

430

Catalytic asymmetric assembly of octahydroindolones: divergent synthesis of lycorine-type amaryllidaceae alkaloids (+)-?-lycorane and (+)-lycorine.  

PubMed

We report the first catalytic asymmetric approach to octahydroindolones and a divergent enantioselective synthesis of perhydroindole alkaloids, as exemplified by lycorine-type Amaryllidaceae alkaloids (+)-?-lycorane and (+)-lycorine, from a common intermediate by using a highly concise route. The assembly of octahydroindolones employs a catalytic enantioselective 1,4-conjugate addition of nitro dienynes, followed by a TsOH-catalyzed cascade synthesis of highly functionalized enones, and a diastereoselective intramolecular Michael addition. PMID:24700723

Sun, Zhongwen; Zhou, Mingtao; Li, Xiang; Meng, Xueling; Peng, Fangzhi; Zhang, Hongbin; Shao, Zhihui

2014-05-12

431

Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum  

Microsoft Academic Search

Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1–3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF.

Kan’ichiro Ishiuchi; Takaaki Kubota; Haruaki Ishiyama; Shigeki Hayashi; Toshiro Shibata; Koichiro Mori; Yutaro Obara; Norimichi Nakahata; Jun’ichi Kobayashi

2011-01-01

432

Complanadine B, obscurumines A and B, new alkaloids from two species of Lycopodium  

Microsoft Academic Search

A new dimer of C16N2 type alkaloid, complanadine B (1), and two new C16N type alkaloids, obscurumines A (2) and B (3), have been isolated from the club moss Lycopodium complanatum and L. obscurum, respectively. The structures and stereochemistry of 1–3 were elucidated by combination of 2D NMR spectra and chemical transformation. Complanadine A (4) isolated together with 1 induced

Hiroshi Morita; Kan'ichiro Ishiuchi; Asami Haganuma; Tomohiro Hoshino; Yutaro Obara; Norimichi Nakahata; Jun'ichi Kobayashi

2005-01-01

433

Lyconadins D and E, and complanadine E, new Lycopodium alkaloids from Lycopodium complanatum.  

PubMed

Three new Lycopodium alkaloids, lyconadins D (1) and E (2), and complanadine E (3), were isolated from the club moss Lycopodium complanatum. Lyconadin D (1) was the first example of fastigiatine-type alkaloid isolated from Lycopodium complanatum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data. Complanadine E (3) enhanced mRNA expression for NGF. PMID:21215644

Ishiuchi, Kan'ichiro; Kubota, Takaaki; Ishiyama, Haruaki; Hayashi, Shigeki; Shibata, Toshiro; Mori, Koichiro; Obara, Yutaro; Nakahata, Norimichi; Kobayashi, Jun'ichi

2011-01-15

434

Identification and quantitation of opium alkaloids in somatic embryos of Papaver somniferum L.  

E-print Network

IDENTIFICATION AND QUANTITATION OF OPIUM ALKALOIDS IN SOMATIC EMBRYOS OF PAPAVER SOMNIFERUM L. A Thesis by SAMUEL GALEWSKY Submitted to the Graduate College of Texas A&M University in Partial fulfillment of the requirements for the degree... of MASTER OF SCIENCE May 1985 Major Subject: Biology IDENTIFICATION AND QUANTITATION OP OPIUM ALKALOIDS IN SOMATIC EMBRTOS OF PAPAVER SOMNIFERUM L. A Thesis by SAMUEL GALEWSKY Approved as to style and content by: C. L. Nessler (Chairman...

Galewsky, Samuel

1985-01-01

435

Production of alkaloids and differentiation in a submerged culture of Claviceps purpurea (Fr.) Tul  

Microsoft Academic Search

The submerged culture of theClaviceps purpurea strain studied was polymorphous. In. the process of alkaloid synthesis, cytodifferentiation preceded biochemical differentiation.\\u000a The onset of the alkaloid phase was characterized by. predominance of chlamydospores in the culture, the presence of vegetative\\u000a cells with reduced or arrested proliferation, maximum acetylCoA carboxylase activity, the maximum amount of total fatty acids,\\u000a an over-average cell pool

Z. ?ehá?ek; J. Kozová

1975-01-01

436

Biosynthetic studies on adaline and adalinine, two alkaloids from ladybird beetles (Coleoptera: Coccinellidae)  

Microsoft Academic Search

The biosynthesis of the homotropane alkaloid (?)-adaline in the coccinellid beetle Adalia bipunctata has been studied by incorporation experiments with [1-14C] and [2-14C]acetate. A degradation scheme was developed which selectively afforded benzoic acid containing the carbonyl carbon atom of adaline. The labelling pattern thus obtained indicated that the alkaloid is biosynthesized via a polyacetate pathway. Moreover, feeding A. bipunctata adults

Pascal Laurent; Benjamine Lebrun; Jean-Claude Braekman; Désiré Daloze; Jacques M Pasteels

2001-01-01

437

In vitro production of adaline and coccinelline, two defensive alkaloids from ladybird beetles (Coleoptera: Coccinellidae)  

Microsoft Academic Search

In vitro experiments using [1–14C] and [2–14C]acetate were devised to study the biosynthesis of the defensive coccinellid alkaloids adaline and coccinelline in Adalia 2-punctata and Coccinella 7-punctata, respectively. The labelled alkaloids obtained in these experiments had a specific activity about ten times higher than that of the samples obtained in feeding experiments. This in vitro assay has enabled us to

Pascal Laurent; Jean-Claude Braekman; Désiré Daloze; Jacques M. Pasteels

2002-01-01

438

Developmental regulation of benzylisoquinoline alkaloid biosynthesis in opium poppy plants and tissue cultures  

Microsoft Academic Search

Summary  Opium poppy (Papaver somniferum L.) contains a number of pharmaceutically important alkaloids of the benzylisoquinoline type including morphine, codeine,\\u000a papaverine, and sanguinarine. Although these alkaloids accumulate to high concentrations in various organs of the intact plant,\\u000a only the phytoalexin sanguinarine has been found at significant levels in opium poppy cell cultures. Moreover, even sanguinarine\\u000a biosynthesis is not constitutive in poppy

Peter J. Facchini; David A. Bird

1998-01-01

439

Chamobtusin A, a novel skeleton diterpenoid alkaloid from Chamaecyparis obtusa cv. tetragon.  

PubMed

The novel diterpenoid alkaloid chamobtusin A (1) was isolated from the branches and leaves of Chamaecyparis obtusa cv. tetragon. Its structure and relative stereochemistry were mainly determined by MS, 2D NMR, and X-ray methods. The methanol extracts, total alkaloids of C. obtusa cv. tetragon, and chamobtusin A were tested for their cytotoxicities against A549 and K562 human tumor cell lines. PMID:17894506

Zhang, Yu-Mei; Tan, Ning-Hua; Lu, Yang; Chang, Ying; Jia, Rui-Rui

2007-10-25

440

Qualitative determination of indole alkaloids, triterpenoids and steroids of Tabernaemontana hilariana  

Microsoft Academic Search

This paper reports the separation and identification of indole alkaloids, steroids and triterpenoids from the ethanolic extracts of Tabernaemontana hilariana (Apocynaceae). The alkaloidal fractions from the ethanolic extracts obtained (root barks, green fruits, ripe fruits and seeds) were fractionated and analysed by thin-layer chromatography, capillary gas chromatography–flame ionization detection (cGC–FID) as well as by high-resolution gas chromatography–mass spectrometry (HRGC–MS). 3-Hydroxycoronaridine,

Cláudia A. L Cardoso; Wagner Vilegas; Neli K Honda

1998-01-01

441

Collective total synthesis of tetracyclic diquinane Lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof.  

PubMed

The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (-)-magellanine, (+)-magellaninone, and two analogues (-)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guided addition of a strategically useful hydroxyl group at C-3 of paniculatine, the formidable tetracyclic core was rapidly synthesized utilizing a site-specific and stereoselective aldol cyclization, thus making the ABD ? ABCD tetracyclic approach to diquinane Lycopodium alkaloids attainable for the first time. PMID:25299586

Jiang, Shi-Zhi; Lei, Ting; Wei, Kun; Yang, Yu-Rong

2014-11-01

442

Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis.  

PubMed

Molecular clones encoding nine consecutive biosynthetic enzymes that catalyze the conversion of l-dopa to the protoberberine alkaloid (S)-canadine were isolated from meadow rue (Thalictrum flavum ssp glaucum). The predicted proteins showed extensive sequence identity with corresponding enzymes involved in the biosynthesis of related benzylisoquinoline alkaloids in other species, such as opium poppy (Papaver somniferum). RNA gel blot hybridization analysis showed that gene transcripts for each enzyme were most abundant in rhizomes but were also detected at lower levels in roots and other organs. In situ RNA hybridization analysis revealed the cell type-specific expression of protoberberine alkaloid biosynthetic genes in roots and rhizomes. In roots, gene transcripts for all nine enzymes were localized to immature endodermis, pericycle, and, in some cases, adjacent cortical cells. In rhizomes, gene transcripts encoding all nine enzymes were restricted to the protoderm of leaf primordia. The localization of biosynthetic gene transcripts was in contrast with the tissue-specific accumulation of protoberberine alkaloids. In roots, protoberberine alkaloids were restricted to mature endodermal cells upon the initiation of secondary growth and were distributed throughout the pith and cortex in rhizomes. Thus, the cell type-specific localization of protoberberine alkaloid biosynthesis and accumulation are temporally and spatially separated in T. flavum roots and rhizomes, respectively. Despite the close phylogeny between corresponding biosynthetic enzymes, distinct and different cell types are involved in the biosynthesis and accumulation of benzylisoquinoline alkaloids in T. flavum and P. somniferum. Our results suggest that the evolution of alkaloid metabolism involves not only the recruitment of new biosynthetic enzymes, but also the migration of established pathways between cell types. PMID:15722473

Samanani, Nailish; Park, Sang-Un; Facchini, Peter J

2005-03-01

443

Cell Type–Specific Localization of Transcripts Encoding Nine Consecutive Enzymes Involved in Protoberberine Alkaloid Biosynthesis  

PubMed Central

Molecular clones encoding nine consecutive biosynthetic enzymes that catalyze the conversion of l-dopa to the protoberberine alkaloid (S)-canadine were isolated from meadow rue (Thalictrum flavum ssp glaucum). The predicted proteins showed extensive sequence identity with corresponding enzymes involved in the biosynthesis of related benzylisoquinoline alkaloids in other species, such as opium poppy (Papaver somniferum). RNA gel blot hybridization analysis showed that gene transcripts for each enzyme were most abundant in rhizomes but were also detected at lower levels in roots and other organs. In situ RNA hybridization analysis revealed the cell type–specific expression of protoberberine alkaloid biosynthetic genes in roots and rhizomes. In roots, gene transcripts for all nine enzymes were localized to immature endodermis, pericycle, and, in some cases, adjacent cortical cells. In rhizomes, gene transcripts encoding all nine enzymes were restricted to the protoderm of leaf primordia. The localization of biosynthetic gene transcripts was in contrast with the tissue-specific accumulation of protoberberine alkaloids. In roots, protoberberine alkaloids were restricted to mature endodermal cells upon the initiation of secondary growth and were distributed throughout the pith and cortex in rhizomes. Thus, the cell type–specific localization of protoberberine alkaloid biosynthesis and accumulation are temporally and spatially separated in T. flavum roots and rhizomes, respectively. Despite the close phylogeny between corresponding biosynthetic enzymes, distinct and different cell types are involved in the biosynthesis and accumulation of benzylisoquinoline alkaloids in T. flavum and P. somniferum. Our results suggest that the evolution of alkaloid metabolism involves not only the recruitment of new biosynthetic enzymes, but also the migration of established pathways between cell types. PMID:15722473

Samanani, Nailish; Park, Sang-Un; Facchini, Peter J.

2005-01-01

444

Numerical Algorithms  

NSDL National Science Digital Library

CSC 325. (MAT 325) Numerical Algorithms (3) Prerequisite: CSC 112 or 121, MAT 162. An introduction to the numerical algorithms fundamental to scientific computer work. Includes elementary discussion of error, polynomial interpolation, quadrature, linear systems of equations, solution of nonlinear equations and numerical solution of ordinary differential equations. The algorithmic approach and the efficient use of the computer are emphasized.

Tagliarini, Gene

2003-04-21

445

Contribution of fungal loline alkaloids to protection from aphids in a grass-endophyte mutualism.  

PubMed

Fungal endophytes provide grasses with enhanced protection from herbivory, drought, and pathogens. The loline alkaloids (saturated 1-aminopyrrolizidines with an oxygen bridge) are fungal metabolites often present in grasses with fungal endophytes of the genera Epichloë or Neotyphodium. We conducted a Mendelian genetic analysis to test for activity of lolines produced in plants against aphids feeding on those plants. Though most loline-producing endophytes are asexual, we found that a recently described sexual endophyte, Epichloë festucae, had heritable variation for loline alkaloid expression (Lol+) or nonexpression (Lol-). By analyzing segregation of these phenotypes and of linked DNA polymorphisms in crosses, we identified a single genetic locus controlling loline alkaloid expression in those E. festucae parents. We then tested segregating Lol+ and Lol- full-sibling fungal progeny for their ability to protect host plants from two aphid species, and observed that alkaloid expression cosegregated with activity against these insects. The in planta loline alkaloid levels correlated with levels of anti-aphid activity. These results suggested a key role of the loline alkaloids in protection of host plants from certain aphids, and represent, to our knowledge, the first Mendelian analysis demonstrating how a fungal factor contributes protection to plant-fungus mutualism. PMID:11043464

Wilkinson, H H; Siegel, M R; Blankenship, J D; Mallory, A C; Bush, L P; Schardl, C L

2000-10-01

446

Catharanthus roseus tissue culture: the effects of medium modifications on growth and alkaloid production.  

PubMed

A number of nutritional factors as well as the growth factors 2,4-D and IAA were studied to determine their influence on growth and alkaloid formation in Catharanthus roseus suspension cultures. The optimal 2,4-D concentration for growth and alkaloid production was 1 mg/liter. With IAA, both 0.5 and 2.0 mg/liter in media produced tissue growth comparable to tissue receiving 1 mg/liter 2,4-D; however, qualitative and quantitative differences in alkaloid production were observed. Media formulations containing 2,4 and 6% sucrose showed proportionate increases in cell yield with increased sucrose, but concomitant decreases in alkaloid production. Suspension cultures in media containing 2, 5, and 10 times the normal level of phosphate exhibited little change in growth or alkaloid production. When thiamin HCl, yridoxine nicotinic acid and inositol were deleted from the medium, the tissue continued to grow well through the 24 month duration of the experiment; however, alkaloid production was altered quantitatively and qualitatively. PMID:895391

Carew, D P; Krueger, R J

1977-01-01

447

Aptamer-based molecular recognition of lysergamine, metergoline and small ergot alkaloids.  

PubMed

Ergot alkaloids are mycotoxins produced by fungi of the genus Claviceps, which infect cereal crops and grasses. The uptake of ergot alkaloid contaminated cereal products can be lethal to humans and animals. For food safety assessment, analytical techniques are currently used to determine the presence of ergot alkaloids in food and feed samples. However, the number of samples which can be analyzed is limited, due to the cost of the equipment and the need for skilled personnel. In order to compensate for the lack of rapid tests for the detection of ergot alkaloids, the aim of this study was to develop a specific recognition element for ergot alkaloids, which could be further applied to produce a colorimetric reaction in the presence of these toxins. As recognition elements, single-stranded DNA ligands were selected by using an iterative selection procedure named SELEX, i.e., Systematic Evolution of Ligands by EXponential enrichment. After several selection cycles, the resulting aptamers were cloned and sequenced. A surface plasmon resonance analysis enabled determination of the dissociation constants of the complexes of aptamers and lysergamine. Dissociation constants in the nanomolar range were obtained with three selected aptamers. One of the selected aptamers, having a dissociation constant of 44 nM, was linked to gold nanoparticles and it was possible to produce a colorimetric reaction in the presence of lysergamine. This system could also be applied to small ergot alkaloids in an ergot contaminated flour sample. PMID:23242153

Rouah-Martin, Elsa; Mehta, Jaytry; van Dorst, Bieke; de Saeger, Sarah; Dubruel, Peter; Maes, Bert U W; Lemiere, Filip; Goormaghtigh, Erik; Daems, Devin; Herrebout, Wouter; van Hove, François; Blust, Ronny; Robbens, Johan

2012-01-01

448

Measurement of antiphotooxidative properties of isoquinoline alkaloids using transient thermal lens spectroscopy  

NASA Astrophysics Data System (ADS)

The antiphotooxidative properties of boldine and chloride berberine were studied by time-resolved thermal lensing technique. These compounds belong to isoquinoline alkaloids possessing interesting biological activity (e.g. antibacterial, antimalarial, antitumor). Antiphotooxidative properties of the alkaloids were studied by mechanism of energy transference between powerful oxidizing agents such as singlet oxygen. Singlet oxygen was produced by energy transfer from chlorophyll-sensitized photooxidation of oil by exposure of high light intensities like laser. The lifetimes of singlet oxygen in dimethylsulfoxide, methanol and water were determined to confirm the assignment of the singlet molecular oxygen O II (1? g) in the experiments. In order to understand the effect of the alkaloids on active oxygen species, we carried out in detail an analysis of the thermal lensing signal. It was shown that the alkaloids can act as quenchers of singlet oxygen. To demonstrate the ability of the alkaloids to act efficient singlet oxygen acceptors, we have measured the fluorescence spectra of the studied alkaloids in the presence and in the absence of singlet oxygen. The antiphotooxidative activity of boldine and chloride berberine can be explained by the ability to quench singlet oxygen.

Hung, J.; Castillo, J.; Laboren, I.; Rodríguez, M.; Hassegawa, M.

2005-11-01

449

Currencies of mutualisms: sources of alkaloid genes in vertically transmitted epichloae.  

PubMed

The epichloae (Epichloë and Neotyphodium species), a monophyletic group of fungi in the family Clavicipitaceae, are systemic symbionts of cool-season grasses (Poaceae subfamily Poöideae). Most epichloae are vertically transmitted in seeds (endophytes), and most produce alkaloids that attack nervous systems of potential herbivores. These protective metabolites include ergot alkaloids and indole-diterpenes (tremorgens), which are active in vertebrate systems, and lolines and peramine, which are more specific against invertebrates. Several Epichloë species have been described which are sexual and capable of horizontal transmission, and most are vertically transmissible also. Asexual epichloae are mainly or exclusively vertically transmitted, and many are interspecific hybrids with genomic contributions from two or three ancestral Epichloë species. Here we employ genome-scale analyses to investigate the origins of biosynthesis gene clusters for ergot alkaloids (EAS), indole-diterpenes (IDT), and lolines (LOL) in 12 hybrid species. In each hybrid, the alkaloid-gene and housekeeping-gene relationships were congruent. Interestingly, hybrids frequently had alkaloid clusters that were rare in their sexual ancestors. Also, in those hybrids that had multiple EAS, IDT or LOL clusters, one cluster lacked some genes, usually for late pathway steps. Possible implications of these findings for the alkaloid profiles and endophyte ecology are discussed. PMID:23744053

Schardl, Christopher L; Young, Carolyn A; Pan, Juan; Florea, Simona; Takach, Johanna E; Panaccione, Daniel G; Farman, Mark L; Webb, Jennifer S; Jaromczyk, Jolanta; Charlton, Nikki D; Nagabhyru, Padmaja; Chen, Li; Shi, Chong; Leuchtmann, Adrian

2013-06-01

450

Effects of different elicitors on yield of tropane alkaloids in hairy roots of Anisodus acutangulus.  

PubMed

The four tropane alkaloids have played a pivotal role in controlling diseases such as the toxic and septic shock, the organophosphorus poison and the acute lung injury. Here, the elicitation effect of different elicitors on the production of tropane alkaloids and the molecular mechanism of enzyme genes in the pathway was firstly demonstrated in hairy roots of Anisodus acutangulus. The results showed ethanol, methyl jasmonate and Ag(+) could improve the accumulation of tropane alkaloids up to 1.51, 1.13 and 1.08 times after 24 h treatment, respectively (P < 0.05), whereas salicylic acid decreased the average content of tropane alkaloids. Furthermore, expression profile analysis results revealed that up-regulation of hyoscyamine-6b-hydroxylase (AaH6H) and little regulation of tropinone reducase II (AaTR2) elicited by ethanol, increased expression of putrescine N-methyltransferase I (AaPMT1) elicited by Ag(+), elevated expression of tropinone reducase I (AaTR1) elicited by methyl jasmonate, respectively, resulted in tropane alkaloids improvement. Our results showed that hairy root culture of A. acutangulus in combination with elicitors was a promising way for production of tropane alkaloids in the future. PMID:21625855

Kai, Guoyin; Yang, Sheng; Zhang, Yan; Luo, Xiuqin; Fu, Xueqing; Zhang, Ang; Xiao, Jianbo

2012-02-01

451

Chemical composition of bioactive alkaloid extracts from some Narcissus species and varieties and their biological activity.  

PubMed

Alkaloid extracts of eight Narcissus (Amaryllidaceae) species and varieties were studied with respect to their acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE) inhibitory activity and alkaloid patterns. Thirty alkaloids were determined by GC/MS, and twenty-five of them identified from their mass spectra, retention times and retention indexes. Promising HuAChE inhibition activity was demonstrated by six Narcissus taxa and HuBuChE inhibition by N. jonquila cv. Double Campernelle and N. nanus cv. Elka with IC50 values of 24.1 +/- 1.9 microg/mL and 25.1 +/- 1.8 microg/mL, respectively. Two alkaloids were isolated in pure form using preparative TLC and identified as the galanthamine type alkaloid narwedine and the lycorine type alkaloid incartine. Both compounds were tested for their biological activity. They were considered inactive in HuAChE/HuBuChE assays, but showed promising prolyl oligopeptidase inhibition activities with IC50 values of 0.95 +/- 0.12 mM and 0.91 ? 0.09 mM, respectively. PMID:25233595

Havlasová, Jana; Safratová, Marcela; Siatka, Tomás; St?pánková, Sárka; Novák, Zden?k; Locárek, Miroslav; Opletal, Lubomír; Hrabinová, Martina; Jun, Daniel; Benesová, Nina; Kunes, Jirí; Cahlíková, Lucie

2014-08-01

452

Acaricidal activity of alkaloid fractions of Leucas indica Spreng against Rhipicephalus (Boophilus) annulatus tick.  

PubMed

The acaricidal activity from alkaloid and non-alkaloid fractions of Leucas indica were studied against Rhipicephalus (Boophilus) annulatus tick using adult immersion test under laboratory conditions. For this purpose, the engorged female R.(B.) annulatus tick were exposed to two fold serial dilutions of alkaloid extract (50 mg/ml, 25 mg/ml, 12.5 mg/ml, 6 mg/ml and 3 mg/ml) using 'dipping method' in vitro. The efficacy was assessed by measuring the percentage of adult mortality, inhibition of fecundity and hatching rate. The alkaloid fraction of the extract produced concentration dependent delayed adult tick mortality. The extract at a concentration of 50 mg/ml demonstrated 66.67 per cent mortality and 55.16 per cent inhibition of fecundity. Nicotine was identified as one of the compounds of alkaloid fraction. However, it did not reveal any acaricidal activity when tested in vitro at concentrations ranging from 62.5-1000 ?g/mL. Hence, the acaricidal action of L. indica is not due to nicotine. Non alkaloid fraction also did not reveal any acaricidal effects against R. (B.) annulatus tick. PMID:24862044

Divya, T M; Soorya, V C; Amithamol, K K; Juliet, S; Ravindran, R; Nair, S N; Ajithkumar, K G

2014-03-01

453

Roman Numerals  

NSDL National Science Digital Library

This website provides an overview of the Principles of Roman numerals as well as a history of Roman numerals, which dates back to 1st millennium BC when they were used by Romans to record numbers in stone, art and coins. Some pictures in the gallery highlight the ways in which Roman Numerals are used today, such as on watch and clock faces. The authors point out that Roman numerals have a classic style and are less functional than the Arabic (decimal) numbers ( 0 to 9 ) which were introduced into Europe about 900 AD and adopted quickly because of their convenience and mathematical ease of use. They also provide lists (including one of Roman Numerals 1 to 2016), tables, and a converter that visitors can use to convert Roman numeral numbers to decimal numbers. Another section provides resources for teachers on lesson ides for teaching Roman Numerals.

454

The effect of varying alkaloid concentrations on the feeding behavior of gypsy moth larvae, Lymantria dispar (L.) (Lepidoptera: Lymantriidae)  

Microsoft Academic Search

Nine alkaloids (acridine, aristolochic acid, atropine, berberine, caffeine, nicotine, scopolamine, sparteine, and strychnine)\\u000a were evaluated as feeding deterrents for gypsy moth larvae (Lymantria dispar (L.); Lepidoptera: Lymantriidae). Our aim was to determine and compare the taste threshold concentrations, as well as the\\u000a ED50 values, of the nine alkaloids to determine their potency as feeding deterrents. The alkaloids were applied to

Vonnie D. C. Shields; Kristen P. Smith; Nicole S. Arnold; Ineta M. Gordon; Taharah E. Shaw; Danielle Waranch

2008-01-01

455

Development of an efficient system for the separation of indole alkaloids by high performance liquid chromatography and its applications.  

PubMed

An efficient system for the analysis of indole alkaloids by HPLC on a reversed-phase column using an ion pair technique is described. The optimised chromatographic conditions allowed the successful separation of 22 standard monoterpenoid indole alkaloids (including some isomers) and tryptamine. The described HPLC system was applied to the analysis of alkaloids in intergeneric somatic hybrid cell cultures of Rauvolfia serpentina x Rhazya stricta. PMID:11705246

Gerasimenko, I; Sheludko, Y; Unger, M; Stöckigt, J

2001-01-01

456

Identification and quantitation of alkaloids in coca tea  

PubMed Central

The consumption of coca tea is a common occurrence in many South American countries. The tea is often packaged in individual servings as tea bags which contain approximately 1 g of plant material. The consumption of coca tea leads to ingestion of cocaine and other alkaloids: however, there is little information available regarding the pharmacological or toxicological effects that result from consumption of coca tea. We performed a series of studies with coca tea bags from two South American countries, Peru and Bolivia. The alkaloidal content of the ‘coca leaf’ in coca tea bags was determined by two different extraction methods: Soxhlet extraction with methanol (exhaustive extraction), and mechanical agitation with methanol. Extracts were purified by solid-phase extraction (SPE) followed by analysis by gas chromatography/mass spectrometry (GC/MS). Coca tea prepared from Peruvian and Bolivian coca tea bags was also analyzed by SPE-GC/MS assay. In addition, urine specimens were analyzed from an individual who consumed one cup of Peruvian coca tea and one cup of Bolivian coca tea on separate occasions. Urine samples were analyzed by immunoassay (TDxR) and SPE-GC/MS. Analysis of coca tea bags and coca tea indicated that cocaine, benzoylecgonine, ecgonine methyl ester and trans-cinnamoylcocaine were present in varying quantities. With exhaustive extraction, an average of 5.11 mg, and 4.86 mg of cocaine per tea bag were found in coca leaf from Peru and Bolivia, respectively. The average amounts of benzoylecgonine and ecgonine methyl ester in Peruvian coca leaf were 0.11 and 1.15 mg, and in Bolivian coca leaf were 0.12 and 2.93 mg per tea bag, respectively. trans-Cinnamoylcocaine was found in trace amounts in Peruvian tea bags and 0.16 mg/tea bag of Bolivian tea. When tea was prepared, an average of 4.14 mg of cocaine was present in a cup of Peruvian coca tea and 4.29 mg of cocaine was present in Bolivian tea. Following the consumption of a cup of Peruvian tea by one individual, a peak urine benzoylecgonine concentration of 3940 ng/ml occurred 10 h after ingestion. Consumption of Bolivian coca tea resulted in a peak benzoylecgonine concentration of 4979 ng/ml at 3.5 h. The cumulative urinary excretion of benzoylecgonine after approximately 48 h, determined by GC/MS, was 3.11 mg and 2.69 mg after consumption of Peruvian and Bolivian coca tea, respectively. This study demonstrated that coca tea bags and coca tea contain a significant amount of cocaine and cocaine-related alkaloids and the consumption of a single cup of Peruvian or Bolivian coca tea produces positive drug test results for cocaine metabolites. PMID:8819993

Jenkins, Amanda J.; Llosa, Teobaldo; Montoya, Ivan

2008-01-01

457

The Only African Wild Tobacco, Nicotiana africana: Alkaloid Content and the Effect of Herbivory  

PubMed Central

Herbivory in some Nicotiana species is known to induce alkaloid production. This study examined herbivore-induced defenses in the nornicotine-rich African tobacco N. africana, the only Nicotiana species indigenous to Africa. We tested the predictions that: 1) N. africana will have high constitutive levels of leaf, flower and nectar alkaloids; 2) leaf herbivory by the African bollworm Helicoverpa armigera will induce increased alkaloid levels in leaves, flowers and nectar; and 3) increased alkaloid concentrations in herbivore-damaged plants will negatively affect larval growth. We grew N. africana in large pots in a greenhouse and exposed flowering plants to densities of one, three and six fourth-instar larvae of H. armigera, for four days. Leaves, flowers and nectar were analyzed for nicotine, nornicotine and anabasine. The principal leaf alkaloid was nornicotine (mean: 28 µg/g dry mass) followed by anabasine (4.9 µg/g) and nicotine (0.6 µg/g). Nornicotine was found in low quantities in the flowers, but no nicotine or anabasine were recorded. The nectar contained none of the alkaloids measured. Larval growth was reduced when leaves of flowering plants were exposed to six larvae. As predicted by the optimal defense theory, herbivory had a localized effect and caused an increase in nornicotine concentrations in both undamaged top leaves of herbivore damaged plants and herbivore damaged leaves exposed to one and three larvae. The nicotine concentration increased in damaged compared to undamaged middle leaves. The nornicotine concentration was lower in damaged leaves of plants exposed to six compared to three larvae, suggesting that N. africana rather invests in new growth as opposed to protecting older leaves under severe attack. The results indicate that the nornicotine-rich N. africana will be unattractive to herbivores and more so when damaged, but that potential pollinators will be unaffected because the nectar remains alkaloid-free even after herbivory. PMID:25025217

Marlin, Danica; Nicolson, Susan W.; Yusuf, Abdullahi A.; Stevenson, Philip C.; Heyman, Heino M.; Krüger, Kerstin

2014-01-01

458

Differences in tolerance to host cactus alkaloids in Drosophila koepferae and D. buzzatii.  

PubMed

The evolution of cactophily in the genus Drosophila was a major ecological transition involving over a hundred species in the Americas that acquired the capacity to cope with a variety of toxic metabolites evolved as feeding deterrents in Cactaceae. D. buzzatii and D. koepferae are sibling cactophilic species in the D. repleta group. The former is mainly associated with the relatively toxic-free habitat offered by prickly pears (Opuntia sulphurea) and the latter has evolved the ability to use columnar cacti of the genera Trichocereus and Cereus that contain an array of alkaloid secondary compounds. We assessed the effects of cactus alkaloids on fitness-related traits and evaluated the ability of D. buzzatii and D. koepferae to exploit an artificial novel toxic host. Larvae of both species were raised in laboratory culture media to which we added increasing doses of an alkaloid fraction extracted from the columnar cactus T. terschekii. In addition, we evaluated performance on an artificial novel host by rearing larvae in a seminatural medium that combined the nutritional quality of O. sulphurea plus amounts of alkaloids found in fresh T. terschekii. Performance scores in each rearing treatment were calculated using an index that took into account viability, developmental time, and adult body size. Only D. buzzatii suffered the effects of increasing doses of alkaloids and the artificial host impaired viability in D. koepferae, but did not affect performance in D. buzzatii. These results provide the first direct evidence that alkaloids are key determinants of host plant use in these species. However, the results regarding the artificial novel host suggest that the effects of alkaloids on performance are not straightforward as D. koepferae was heavily affected. We discuss these results in the light of patterns of host plan evolution in the Drosophila repleta group. PMID:24520377

Soto, Ignacio M; Carreira, Valeria P; Corio, Cristian; Padró, Julián; Soto, Eduardo M; Hasson, Esteban

2014-01-01

459

Mutation in the Plasmodium falciparum CRT Protein Determines the Stereospecific Activity of Antimalarial Cinchona Alkaloids  

PubMed Central

The Cinchona alkaloids are quinoline aminoalcohols that occur as diastereomer pairs, typified by (?)-quinine and (+)-quinidine. The potency of (+)-isomers is greater than the (?)-isomers in vitro and in vivo against Plasmodium falciparum malaria parasites. They may act by the inhibition of heme crystallization within the parasite digestive vacuole in a manner similar to chloroquine. Earlier studies showed that a K76I mutation in the digestive vacuole-associated protein, PfCRT (P. falciparum chloroquine resistance transporter), reversed the normal potency order of quinine and quinidine toward P. falciparum. To further explore PfCRT-alkaloid interactions in the malaria parasite, we measured the in vitro susceptibility of eight clonal lines of P. falciparum derived from the 106/1 strain, each containing a unique pfcrt allele, to four Cinchona stereoisomer pairs: quinine and quinidine; cinchonidine and cinchonine; hydroquinine and hydroquinidine; 9-epiquinine and 9-epiquinidine. Stereospecific potency of the Cinchona alkaloids was associated with changes in charge and hydrophobicity of mutable PfCRT amino acids. In isogenic chloroquine-resistant lines, the IC50 ratio of (?)/(+) CA pairs correlated with side chain hydrophobicity of the position 76 residue. Second-site PfCRT mutations negated the K76I stereospecific effects: charge-change mutations C72R or Q352K/R restored potency patterns similar to the parent K76 line, while V369F increased susceptibility to the alkaloids and nullified stereospecific differences between alkaloid pairs. Interactions between key residues of the PfCRT channel/transporter with (?) and (+) alkaloids are stereospecifically determined, suggesting that PfCRT binding plays an important role in the antimalarial activity of quinine and other Cinchona alkaloids. PMID:22869567

Griffin, Carol E.; Hoke, Jonathan M.; Samarakoon, Upeka; Duan, Junhui; Mu, Jianbing; Ferdig, Michael T.; Warhurst, David C.

2012-01-01

460

Identification of cellular and molecular factors determining the response of cancer cells to six ergot alkaloids.  

PubMed

Ergot alkaloids are psychoactive and vasoconstricting agents of the fungus Claviceps purpurea causing poisoning such as ergotism in medieval times (St. Anthony's Fire). This class of substances also inhibits tumor growth in vitro and in vivo, though the underlying mechanisms are unclear as yet. We investigated six ergot alkaloids (agroclavine, ergosterol, ergocornin E, ergotamine, dihydroergocristine, and 1-propylagroclavine tartrate) for their cytotoxicity towards tumor cell lines of the National Cancer Institute, USA. 1-Propylagroclavine tartrate (1-PAT) revealed the strongest cytotoxicity. Out of 76 clinically established anticancer drugs, cross-resistance was found between the ergot alkaloids and 6/7 anti-hormonal drugs (=85.7 %) and 5/15 DNA-alkylating drugs (=33.3 %). The IC50 values for the six alkaloids were not correlated to well-known determinants of drug resistance, such as proliferative activity (as measured by cell doubling times, PCNA expression, and cell cycle distribution), the multidrug resistance-mediating P-glycoprotein/MDR1 and expression or mutations of oncogenes and tumor suppressor genes (EGFR, RAS, TP53). While resistance of control drugs (daunorubicin, cisplatin, erlotinib) correlated with these classical resistance mechanisms, ergot alkaloids did not. Furthermore, COMPARE and hierarchical cluster analyses were performed of mRNA microarray data to identify genes correlating with sensitivity or resistance to 1-PAT. Twenty-three genes were found with different biological functions (signal transducers, RNA metabolism, ribosome constituents, cell cycle and apoptosis regulators etc.). The expression of only 3/66 neuroreceptor genes correlated with the IC50 values for 1-PAT, suggesting that the psychoactive effects of ergot alkaloids may not play a major role for the cytotoxic activity against cancer cells. In conclusion, the cytotoxicity of ergot alkaloids is not involved in classical mechanisms of drug resistance opening the possibility to bypass resistance and to treat otherwise drug-resistant and refractory tumors. The modes of action are multifactorial, which is a typical feature of many natural compounds. PMID:25342140

Mrusek, Marco; Seo, Ean-Jeong; Greten, Henry Johannes; Simon, Michael; Efferth, Thomas

2015-02-01

461

Changes in plant defense chemistry (pyrrolizidine alkaloids) revealed through high-resolution spectroscopy  

NASA Astrophysics Data System (ADS)

Plant toxic biochemicals play an important role in defense against natural enemies and often are toxic to humans and livestock. Hyperspectral reflectance is an established method for primary chemical detection and could be further used to determine plant toxicity in the field. In order to make a first step for pyrrolizidine alkaloids detection (toxic defense compound against mammals and many insects) we studied how such spectral data can estimate plant defense chemistry under controlled conditions. In a greenhouse, we grew three related plant species that defend against generalist herbivores through pyrrolizidine alkaloids: Jacobaea vulgaris, Jacobaea erucifolia and Senecio inaequidens, and analyzed the relation between spectral measurements and chemical concentrations using multivariate statistics. Nutrient addition enhanced tertiary-amine pyrrolizidine alkaloids contents of J. vulgaris and J. erucifolia and decreased N-oxide contents in S. inaequidens and J. vulgaris. Pyrrolizidine alkaloids could be predicted with a moderate accuracy. Pyrrolizidine alkaloid forms tertiary-amines and epoxides were predicted with 63% and 56% of the variation explained, respectively. The most relevant spectral regions selected for prediction were associated with electron transitions and Csbnd H, Osbnd H, and Nsbnd H bonds in the 1530 and 2100 nm regions. Given the relatively low concentration in pyrrolizidine alkaloids concentration (in the order of mg g-1) and resultant predictions, it is promising that pyrrolizidine alkaloids interact with incident light. Further studies should be considered to determine if such a non-destructive method may predict changes in PA concentration in relation to plant natural enemies. Spectroscopy may be used to study plant defenses in intact plant tissues, and may provide managers of toxic plants, food industry and multitrophic-interaction researchers with faster and larger monitoring possibilities.

Carvalho, Sabrina; Macel, Mirka; Schlerf, Martin; Moghaddam, Fatemeh Eghbali; Mulder, Patrick P. J.; Skidmore, Andrew K.; van der Putten, Wim H.

2013-06-01

462

[Effect of a hydrothermal treatment on ergot alkaloid content in ergot contaminated rye].  

PubMed

Hydrothermal treatments are primarily used to increase the digestibility of nutrients and therefore to improve the feeding value of feedstuffs mainly for non-ruminants. Other positive side effects may occur, e.g. a decrease in toxicity of feed contaminated with mycotoxins. To study such effects, 4 batches of rye containing different percentages (0.8, 4.2, 8.3 and 25%) of ergot (Claviceps purpurea) were expanded and ergot alkaloid contents were analysed. After pre-conditioning of each batch by steam exposure for approx. 2 min, at 95 °C and 17% moisture, the material was expanded for approx. 5 sec. at 120 °C, 18% moisture, 40 bar mechanical pressure and 20 kWh/t mechanical energy input. Samples were collected before and after pre-conditioning and after expanding. Ergot alkaloids were analysed by HPLC. Analysis includedErgometrine, Ergotamine, Ergocornine, Ergocryptine, Ergocristine, Ergosine and their respective-inine isomers, the sum of these 12 ergot alkaloids was referred to as the total alkaloid content.On average, the hydrothermal treatment (pre-conditioning and expanding) caused a decrease of the total ergot alkaloid content of approx. 10%. Except for the batch containing 0.8% ergot, the efficiency of the hydrothermal treatment decreased with increasing ergot concentration in the batches. In general, the hydrothermal treatment changed the proportions of the ergot alkaloid isomers since the percentages of the-inine isomers of the total ergot alkaloid contents were increased with reduced-ine percentages. Whether this alteration is of toxicological relevance should be evaluated in animal experiments. PMID:23605271

Mainka, S; Dänicke, S; Ueberschär, K-H; V Reichenbach, H Graf

2005-06-01

463

Heterologous expression of lysergic acid and novel ergot alkaloids in Aspergillus fumigatus.  

PubMed

Different lineages of fungi produce distinct classes of ergot alkaloids. Lysergic acid-derived ergot alkaloids produced by fungi in the Clavicipitaceae are particularly important in agriculture and medicine. The pathway to lysergic acid is partly elucidated, but the gene encoding the enzyme that oxidizes the intermediate agroclavine is unknown. We investigated two candidate agroclavine oxidase genes from the fungus Epichloë festucae var. lolii × Epichloë typhina isolate Lp1 (henceforth referred to as Epichloë sp. Lp1), which produces lysergic acid-derived ergot alkaloids. Candidate genes easH and cloA were expressed in a mutant strain of the mold Aspergillus fumigatus, which typically produces a subclass of ergot alkaloids not derived from agroclavine or lysergic acid. Candidate genes were coexpressed with the Epichloë sp. Lp1 allele of easA, which encodes an enzyme that catalyzed the synthesis of agroclavine from an A. fumigatus intermediate; the agroclavine then served as the substrate for the candidate agroclavine oxidases. Strains expressing easA and cloA from Epichloë sp. Lp1 produced lysergic acid from agroclavine, a process requiring a cumulative six-electron oxidation and a double-bond isomerization. Strains that accumulated excess agroclavine (as a result of Epichloë sp. Lp1 easA expression in the absence of cloA) metabolized it into two novel ergot alkaloids for which provisional structures were proposed on the basis of mass spectra and precursor feeding studies. Our data indicate that CloA catalyzes multiple reactions to produce lysergic acid from agroclavine and that combining genes from different ergot alkaloid pathways provides an effective strategy to engineer important pathway molecules and novel ergot alkaloids. PMID:25107976

Robinson, Sarah L; Panaccione, Daniel G

2014-10-01

464

[Effect of precursor on growth and accumulation of alkaloids of Lycoris radiata suspension cells].  

PubMed

In order to investigate the effects of phenylalanine, tyrosine and tyramine on the growth of Lycoris radiata suspension cells and the accumulation of alkaloids, the growth quantity of the cells as well as the content of alkaloids in cells were determined, which were treated with above three kinds of precursors alone and phenylalanine combined with tyrosine respectively. The results indicate that the addition of phenylalanine alone and addition of phenylalanine on the basis of tyrosine at high concentration (200 micromol/L) had no significant effect on the growth of Lycoris radiata suspension cells and the content of alkaloids in cells; whereas tyrosine and tyramine promoted the growth of the cells and alkaloids accumulation. Treated with tyrosine at high concentration (200 micromol/L), the content of alkaloids of the cells was 2.56-fold higher than that of the control group, the amounts of lycoramine (3.77 mg/g) and galanthamine (4.46 mg/g) were 6.61-fold and 6.97-fold higher than that of the control group, respectively. When treated with tyramine (200 micromol/L), the amount of alkaloids in Lycoris radiata suspension cells was 2.63-fold higher than that of the control group, and the amounts of lycoramine (4.45 mg/g) and galanthamine (5.14 mg/g) were 9.08-fold and 9.18-fold higher than that of the control group, respectively. The above results demonstrate that adding tyrosine and tyramine in the media significantly promoted the growth of the Lycoris radiata suspension cells and alkaloids accumulation in the cells. PMID:24945053

Zhang, Yuqiong; Li, Yong; Zhou, Jianhui; Chen, Na; Wang, Meifang; Dong, Zhaorong; Gao, Cuiyun; Zhong, Yanlong

2014-02-01

465

The Biogeographical Distribution of Duncecap Larkspur ( Delphinium occidentale ) Chemotypes and Their Potential Toxicity  

Microsoft Academic Search

Larkspurs (Delphinium spp.) are poisonous plants found on rangelands in western North America. Larkspur’s toxicity has been attributed to the norditerpenoid\\u000a alkaloids, which are divided into two main structural groups: the highly toxic (N-methylsuccinimido) anthranoyllycoctonine type (MSAL type) and the less toxic 7,8-methylenedioxylycoctonine type (MDL type).\\u000a Plants high in the MSAL-type alkaloids are thought to be the most toxic to

Daniel Cook; Dale R. Gardner; James A. Pfister; Kevin D. Welch; Benedict T. Green; Stephen T. Lee

2009-01-01

466

Anticonvulsant activity of berberine, an isoquinoline alkaloid in mice.  

PubMed

Berberine, an isoquinoline alkaloid is reported to modulate several neurotransmitter systems like N-methyl-D-aspartate, nitric oxide and serotonin, which modulate convulsions. In addition, it is suggested that Berberis vulgaris may be useful in treatment of convulsion and epilepsy. Therefore, the present study investigated the effects of berberine in pentylenetetrazole, maximal electroshock (MES) and kainic acid (KA)-induced convulsions. The latency for development of convulsions and mortality rate was recorded in these models using mice. The results revealed that in MES-induced seizures model, berberine (10 and 20 mg/kg, i.p.) decreased duration of tonic hind limb extension and percent mortality. Moreover, these doses of berberine also protected mice against KA-induced clonic convulsions and decreased mortality. Berberine also protected mice against NMDA-induced turning behavior. Further, the anticonvulsant doses of berberine did not show any signs of motor in-coordination when tested in rotarod test. In conclusion, berberine exhibits anticonvulsant activity by modulating neurotransmitter systems and may find clinical application. PMID:20638957

Bhutada, Pravinkumar; Mundhada, Yogita; Bansod, Kuldeep; Dixit, Pankaj; Umathe, Sudhir; Mundhada, Dharmendra

2010-07-01

467

Microwave Spectroscopy of Alkaloids: the Conformational Shapes of Nicotine  

NASA Astrophysics Data System (ADS)

Nicotinoid alkaloids consist of two ring systems connected via a C-C ?-bond: Joining pyridine either with a (substituted) pyrrolidine or piperidine ring system, pyrrolidinic or piperidinic nicotinoids are formed. Nicotine itself, consisting of pyridine and N-methylpyrrolidine, is the prototype pyrrolidinic nicotinoid. Its coupled heteoaromatic and heteroaliphatic ring systems exhibit three sites that allow for conformational flexibility: (I) puckering of the pyrrolidine ring (Eq./Ax. positions of the pyridine), (II) inversion of the N-methyl group (Eq./Ax. positions of the hydrogen), and (III) relative orientation of the two rings (Syn-Anti). Two conformations of nicotine have been observed using the In-phase/quadrature-phase-Modulation Passage-Acquired-Coherence Technique (IMPACT) Fourier Transform Microwave (FTMW) spectrometer in Valladolid. The preferred conformations are characterized by an equatorial (Eq.) pyridine moiety and equatorial (Eq.) N-CH_3 stereochemistry. The planes of two rings are almost perpendicular with respect to each other while exhibiting two low energy conformations, Syn and Anti, that differ by a 180° rotation about the C-C ?-bond. The Eq.-Eq. conformational preference is likely due to a weak hydrogen bond interaction between the nitrogen lone pair at the N-methylpyrroline and the closest hydrogen in pyridine. Supporting quantum-chemical calculations are also provided. Lavrich, R. J.; Suenram, R. D.; Plusquellic, D. F.; Davis, S. 58th International Symposium on Molecular Spectroscopy, Columbus, OH 2003, RH13.

Grabow, Jens-Uwe; Mata, S.; López, J. C.; Pe?a, I.; Cabezas, C.; Blanco, S.; Alonso, J. L.

2010-06-01

468

Cyclolization of D-lysergic acid alkaloid peptides.  

PubMed

The tripeptide chains of the ergopeptines, a class of pharmacologically important D-lysergic acid alkaloid peptides, are arranged in a unique bicyclic cyclol based on an amino-terminal ?-hydroxyamino acid and a terminal orthostructure. D-lysergyl-tripeptides are assembled by the nonribosomal peptide synthetases LPS1 and LPS2 of the ergot fungus Claviceps purpurea and released as N-(D-lysergyl-aminoacyl)-lactams. We show total enzymatic synthesis of ergopeptines catalyzed by a Fe²?/2-ketoglutarate-dependent dioxygenase (EasH) in conjunction with LPS1/LPS2. Analysis of the reaction indicated that EasH introduces a hydroxyl group into N-(D-lysergyl-aminoacyl)-lactam at ?-C of the aminoacyl residue followed by spontaneous condensation with the terminal lactam carbonyl group. Sequence analysis revealed that EasH belongs to the wide and diverse family of the phytanoyl coenzyme A hydroxylases. We provide a high-resolution crystal structure of EasH that is most similar to that of phytanoyl coenzyme A hydroxylase, PhyH, from human. PMID:24361048

Havemann, Judith; Vogel, Dominik; Loll, Bernhard; Keller, Ullrich

2014-01-16

469

Structures of alkaloid biosynthetic glucosidases decode substrate specificity.  

PubMed

Two similar enzymes with different biosynthetic function in one species have evolved to catalyze two distinct reactions. X-ray structures of both enzymes help reveal their most important differences. The Rauvolfia alkaloid biosynthetic network harbors two O-glucosidases: raucaffricine glucosidase (RG), which hydrolyses raucaffricine to an intermediate downstream in the ajmaline pathway, and strictosidine glucosidase (SG), which operates upstream. RG converts strictosidine, the substrate of SG, but SG does not accept raucaffricine. Now elucidation of crystal structures of RG, inactive RG-E186Q mutant, and its complexes with ligands dihydro-raucaffricine and secologanin reveals that it is the "wider gate" of RG that allows strictosidine to enter the catalytic site, whereas the "slot-like" entrance of SG prohibits access by raucaffricine. Trp392 in RG and Trp388 in SG control the gate shape and acceptance of substrates. Ser390 directs the conformation of Trp392. 3D structures, supported by site-directed mutations and kinetic data of RG and SG, provide a structural and catalytic explanation of substrate specificity and deeper insights into O-glucosidase chemistry. PMID:22004291

Xia, Liqun; Ruppert, Martin; Wang, Meitian; Panjikar, Santosh; Lin, Haili; Rajendran, Chitra; Barleben, Leif; Stöckigt, Joachim

2012-01-20

470

Simultaneous determination of the content of isoquinoline alkaloids in Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids by high-performance liquid chromatography with diode array detection.  

PubMed

A simple and efficient method was developed for the simultaneous determination of eight isoquinoline alkaloids in methanol extracts of Dicranostigma leptopodum (Maxim) Fedde and the effective fractionation of the alkaloids of D. leptopodum by high-performance liquid chromatography with diode array detection. The chromatographic conditions were optimized on a SinoChrom ODS-BP column to obtain a good separation of the four types of alkaloid analytes, including two aporphines (isocorydine, corydine), two protopines (protopine and allocryptopine), a morphine (sinoacutine), and three quaternary protoberberine alkaloids (berberrubine, 5-hydroxycoptisine, and berberine). The separation of these alkaloids was significantly affected by the composition of the mobile phase, and particularly by its pH value. Acetonitrile (A) and 0.2% phosphoric acid solution adjusted to pH 6.32 with triethylamine (B) were selected as the mobile phase with a gradient elution. With this method, a new quaternary protoberberine alkaloid was isolated and the two structural isomers (isocorydine and corydine) were baseline separated. The appropriate harvest period for D. leptopodum was also recommended based on our analysis. The method for the effective fraction of the alkaloids of D. leptopodum was optimized under this method with regard to the varying significant pharmacological activities of the alkaloids. PMID:25330407

Chen, Yali; Li, Min; Liu, Jianjun; Yan, Qian; Zhong, Mei; Liu, Junxi; Di, Duolong; Liu, Jinxia

2015-01-01

471

Dietary alkaloids and the development of androconial organs in Estigmene acrea.  

PubMed

Male salt marsh moths, Estigmene acrea (Lepidoptera: Arctiidae), possess inflatable androconial organs called coremata. Prior to mating males form aggregations and inflate their coremata en masse. The communal display attracts additional males and females for the purpose of mating. The coremata are known to carry the plant-derived dihydropyrrolizine, hydroxydanaidal. This pheromonal substance is derived from secondary plant chemicals called pyrrolizidine alkaloids found in the larval diet. When E. acrea larvae were raised on semi-synthetic diets containing different levels of the pyrrolizidine alkaloid precursors the alkaloids triggered a pronounced morphogenetic effect. Adult males that fed on high levels of the pyrrolizidine alkaloid monocrotaline N-oxide (2500 microg) developed the largest coremata. Males that fed on lower levels of monocrotaline N-oxide (500 microg) or no alkaloid, while normal in body weight, had coremata that were progressively smaller and less robust. The size of the coremata and their commensurate pheromonal charge may have behavioral consequences in the unusual mating system of this species. PMID:15841220

Davenport, Jason W; Conner, William E

2003-01-01

472

Seasonal accumulation of major alkaloids in organs of pharmaceutical crop Narcissus Carlton.  

PubMed

Narcissus pseudonarcissus (L.) cv. Carlton is being cultivated as a main source of galanthamine from the bulbs. After galanthamine, haemanthamine and narciclasine are the next most abundant alkaloids in this cultivar. Both these compounds are promising chemical scaffolds for potential anticancer drugs. For further research and drug development, a reliable supply of these compounds will be needed. In this study a field experiment was conducted to investigate the levels of galanthamine, haemanthamine and narciclasine in plants of N. pseudonarcissus cv. Carlton. In a field experiment alkaloids in the bulbs, leaves and roots were analyzed by quantitative (1)H NMR to monitor the variations during the growing season. Major primary and secondary metabolites were identified in the various plant parts. Multivariate data analysis was performed on the (1)H NMR spectra to investigate how metabolites changed in the plant organs over time. The results show that the leaves have relatively high concentrations of the alkaloids before flowering. The bulbs had lower concentrations of the compounds of interest but would have a higher total yield of alkaloids due to bigger biomass. Narcissus pseudonarcissus cv. Carlton represents a good source of galanthamine, and can potentially be a source of the other major alkaloids depending on choice of organ and harvest time. PMID:23318143

Lubbe, Andrea; Gude, Henk; Verpoorte, Robert; Choi, Young Hae

2013-04-01

473

Optimization of extraction and enrichment of steroidal alkaloids from bulbs of cultivated Fritillaria cirrhosa.  

PubMed

The bulbs of cultivated Fritillaria cirrhosa (BCFC) are used in China both for food and folk medicine due to its powerful biological activities. The aim of this study is to optimize the extraction and enrichment conditions of alkaloids from BCFC. Firstly, the orthogonal experimental design was used to optimize and evaluate four variables (ethanol concentration, solid-liquid ratio, extraction time, and temperature). Thereafter, resin adsorption was as a means to enrich alkaloids. Among 16 tested resins, H-103 resin presented higher adsorption capacity and desorption ratio. The equilibrium experimental data of the adsorption of total alkaloids, imperialine, and peimisine were well-fitted to the pseudo-first-order kinetics model, Langmuir and Freundlich isotherms models. Finally, in order to optimize the parameters for purifying alkaloids, dynamic adsorption and desorption tests were carried out. After one run treatment with H-103 resin, the contents of total alkaloids, imperialine, and peimisine in the product were 21.40-, 18.31-, and 22.88-fold increased with recovery yields of 94.43%, 90.57%, and 96.16%, respectively. PMID:24804207

Wang, Dongdong; Wang, Shu; Du, Qingdan; Wang, Nanyi; Liu, Simei; Wang, Xiaoxia; Jiang, Jinghui

2014-01-01

474

Studies on quantitative determination of total alkaloids and berberine in five origins of crude medicine "sankezhen".  

PubMed

The roots of Berberis plants are widely used as a traditional Chinese medicine called "Sankezhen", having the activities of antibacterial and anti-inflammatory, and the ingredients are alkaloids. This work aims to study and compare the total alkaloids and individual alkaloid (berberine) contents in roots and stems from five origins of Berberis plants (Berberis soulieana Schneid., B. henryana Schneid., B. triacanthophora Fedde, B. gagnepainii Schneid. and B. bergmanniae Schneid.) and provides some references for resource and quality evaluation of the medicine. Acid dye colorimetry and high-performance liquid chromatography were used in the determination. The results showed that the contents for the total alkaloids in root and stem samples were in the range of 1.60-4.72% and 0.76-2.70%, while those of the berberine were 0.70-2.92% and 0.23-1.07%. With higher contents of the total alkaloids and berberine, the roots of B. soulieana, B. gagnepainii and B. bergmanniae were good sources of "Sankezhen". Meanwhile, the contents were also high in stems of the three plants, indicating that the stems were likely to be alternative sources of "Sankezhen" after further research. As the results of precision, stability and recovery tests shown, the methods were simple, rapid and reliable, and provided valuable basis for quality evaluation and new resource investigation of "Sankezhen". PMID:25013028

Li, Luyang; Long, Weifang; Wan, Xiangluan; Ding, Qi; Zhang, Fei; Wan, Dingrong

2015-02-01

475

Luminescence and binding properties of two isoquinoline alkaloids chelerythrine and sanguinarine with ctDNA  

NASA Astrophysics Data System (ADS)

The binding mode and mechanism of the interactions between two planar cationic alkaloids chelerythrine (Che) and sanguinarine (San) with calf thymus DNA (ctDNA) were systematically investigated at pH 5.40 using UV-vis absorption spectroscopy, fluorescence spectroscopy and cyclic voltammetry. Che and San show strong fluorescence at 570 and 589 nm, respectively. Che displays fluorescence enhancement with ctDNA whereas the fluorescence of San is quenched on interaction with ctDNA. In addition, UV-vis spectra of both alkaloids show apparent hypochromicity and are bathochromic shifted, indicating that they could intercalate into ctDNA bases. The fluorescence polarization of Che and San increases in the presence of ctDNA, again implying the intercalation of two alkaloids with ctDNA. This conclusion was also supported by the results obtained from anion quenching and cyclic voltammetry. The binding constants of both alkaloids with ctDNA were calculated in the order of 105 L/mol. San binds with ctDNA 3-fold stronger than Che. The stoichiometric bindings are five nucleotides per Che or San. Electrostatic binding also exists between the alkaloids and DNA helix. Finally, theoretical calculations show that only certain parts of Che and San molecules intercalate into the DNA helix.

Li, Junfen; Li, Baohong; Wu, Yanbo; Shuang, Shaomin; Dong, Chuan; Choi, Martin M. F.

2012-09-01

476

Qualitative and quantitative analyses of alkaloids in Uncaria species by UPLC-ESI-Q-TOF/MS.  

PubMed

An ultra performance liquid chromatography (UPLC) coupled with quadrupole time-of-flight mass spectrometry (Q-TOF/MS) method has been optimized and established for the rapid analysis of the alkaloids in 22 samples originating from five Uncaria (U.) species. The accurate mass measurement of all the protonated molecules and subsequent fragment ions offers higher quality structural information for the interpretation of fragmentation pathways of the various groups of alkaloids. A total of 19 oxindole alkaloids, 16 indole alkaloids and 1 flavone were identified by co-chromatography of the sample extract with authentic standards, comparison of the retention time, characteristic molecular ions and fragment ions, or were tentatively identified by MS/MS determination. Moreover, the method was validated for the simultaneous quantification of the 24 components within 10.5 min. The potential chemical markers were identified for classification of the U. species samples by principal component analysis (PCA) and orthogonal partial least squared discriminant analysis (OPLS-DA). The results demonstrate the similarity and differences in alkaloids among the five U. species, which is helpful for the standardization and quality control of the medical materials of the U. Ramulus Cum Unics (URCU). Furthermore, with multivariate statistical analysis, the determined markers are more definite and useful for chemotaxonomy of the U. genus. PMID:25366313

Wang, Hai-Bo; Qi, Wen; Zhang, Lin; Yuan, Dan

2014-01-01

477

Diversity in aconitine alkaloid profile of Aconitum plants in Hokkaido contrasts with their genetic similarity.  

PubMed

Aconite tuber is a representative crude drug for warming the body internally in Japanese Kampo medicine and Chinese traditional medicine. The crude drug is used in major prescriptions for the aged. Varieties of Aconitum plants are distributed throughout the Japanese Islands, especially Hokkaido. With the aim of identifying the medicinal potential of Aconitum plants from Hokkaido, 107 specimens were collected from 36 sites in the summer of 2011 and 2012. Their nuclear DNA region, internal transcribed spacer (ITS), and aconitine alkaloid contents were analyzed. Phylogenic analysis of ITS by maximum parsimony analysis showed that the majority of the specimens were grouped into one cluster (cluster I), separated from the other cluster (cluster II) consisting of alpine specimens. The aconitine alkaloid content of the tuberous roots of 76 specimens showed 2 aspects-specimens from the same collection site showed similar aconitine alkaloid profiles, and cluster I specimens from different habitats showed various alkaloid profiles. Environmental pressure of each habitat is presumed to have caused the morphology and aconitine alkaloid profile of these genetically similar specimens to diversify. PMID:25199501

Kakiuchi, Nobuko; Atsumi, Toshiyuki; Higuchi, Mari; Kamikawa, Shohei; Miyako, Haruka; Wakita, Yuriko; Ohtsuka, Isao; Hayashi, Shigeki; Hishida, Atsuyuki; Kawahara, Nobuo; Nishizawa, Makoto; Yamagishi, Takashi; Kadota, Yuichi

2015-01-01

478

Medicinally important secondary metabolites in recombinant microorganisms or plants: progress in alkaloid biosynthesis.  

PubMed

Plants produce a high diversity of natural products or secondary metabolites which are important for the communication of plants with other organisms. A prominent function is the protection against herbivores and/or microbial pathogens. Some natural products are also involved in defence against abiotic stress, e.g. UV-B exposure. Many of the secondary metabolites have interesting biological properties and quite a number are of medicinal importance. Because the production of the valuable natural products, such as the anticancer drugs paclitaxel, vinblastine or camptothecin in plants is a costly process, biotechnological alternatives to produce these alkaloids more economically become increasingly important. This review provides an overview of the state of art to produce alkaloids in recombinant microorganisms, such as bacteria or yeast. Some progress has been made in metabolic engineering usually employing a single recombinant alkaloid gene. More importantly, for benzylisoquinoline, monoterpene indole and diterpene alkaloids (taxanes) as well as some terpenoids and phenolics the proof of concept for production of complex alkaloids in recombinant Escherichia coli and yeast has already been achieved. In a long-term perspective, it will probably be possible to generate gene cassettes for complete pathways, which could then be used for production of valuable natural products in bioreactors or for metabolic engineering of crop plants. This will improve their resistance against herbivores and/or microbial pathogens. PMID:19946877

Schäfer, Holger; Wink, Michael

2009-12-01

479

Influence of genetic factors on the ephedrine alkaloid composition ratio of Ephedra plants.  

PubMed

We investigated the ephedrine alkaloid [(-)-ephedrine and (+)-pseudoephedrine] composition ratio of a crude Chinese herbal drug described in the Japanese Pharmacopoeia 'Ephedra herb (Chinese name: Mahuang)'. There were marked changes in the alkaloid composition ratio of wild plants in areas where both male and female clusters coexisted. However, in genetically homogeneous areas with the growth of male or female clusters alone, all of the coefficients of the regression lines were positive, but each gradient varied. This suggests that the alkaloid composition ratio has a clear tendency in each individual. Based on this, we cultivated individuals for vegetative propagation, and evaluated the alkaloid content ratio. Those propagated by separating the roots showed a specific tendency regardless of the cultivation area (Wakayama, Tanegashima). Those propagated by separating the herbaceous stem showed a specific tendency regardless of the soil or harvest time. In addition, we surveyed the (-)-ephedrine content ratio of 3- to 6-year-old strains. There was a high positive correlation coefficient between the previous and subsequent years. These findings suggest that the ephedrine alkaloid composition ratio of Ephedra herb depends on genetic factors, but not on environmental factors or the growth period. PMID:25115226

Matsumoto, Masashi; Hirayama, Manabu; Ohtomi, Norihiro; Ohno, Takeshi; Nomura, Yukihiro; Iida, Osamu; Sugimura, Koji; Kawahara, Nobuo; Tsuchida, Takashi; Mikage, Masayuki

2015-01-01

480

N-Methyldecahydroquinolines: An Unexpected Class of Alkaloids from Amazonian Poison Frogs (Dendrobatidae)  

PubMed Central

The dominant alkaloids previously identified in skin extracts of Amazonian dendrobatid frogs of the genus Ameerega are histrionicotoxins and 2,5-disubstituted decahydroquinolines. Analysis of alkaloids in skin extracts of Ameerega picta from Bolivia revealed that the alkaloid 257A, previously reported as a 2,5-disubstituted decahydroquinoline, is an N-methyl-2,5-disubstituted decahydroquinoline. We characterized alkaloids of another 12 of the more than 25 species recently assigned to the genus Ameerega, and five additional N-methyldecahydroquinolines were identified. In some cases, the relative configuration of the N-methyldecahydroquinolines was determined by comparison with the N-methylated products prepared from the corresponding 2,5-disubstituted decahydroquinolines of known relative configuration. A dietary source for N-methyldecahydroquinolines is unknown; however, myrmicine ants are the likely source for the 2,5-disubstituted decahydroquinolines. The alkaloids in skin extracts of three species of another genus of Amazonian poison frog, Adelphobates, were also characterized, but N-methyldecahydroquinolines were not detected. PMID:19432407

Daly, John W.; Ware, Nathaniel; Saporito, Ralph A.; Spande, Thomas F.; Garraffo, H. Martin

2012-01-01

481

Alkaloid Variation Among Epichloid Endophytes of Sleepygrass (Achnatherum robustum) and Consequences for Resistance to Insect Herbivores.  

PubMed

Epichloid endophytes are well known symbionts of many cool-season grasses that may alleviate environmental stresses for their hosts. For example, endophytes produce alkaloid compounds that may be toxic to invertebrate or vertebrate herbivores. Achnatherum robustum, commonly called sleepygrass, was aptly named due to the presence of an endophyte that causes toxic effects to livestock and wildlife. Variation in alkaloid production observed in two A. robustum populations located near Weed and Cloudcroft in the Lincoln National Forest, New Mexico, suggests two different endophyte species are present in these populations. Genetic analyses of endophyte-infected samples revealed major differences in the endophyte alkaloid genetic profiles from the two populations, which were supported with chemical analyses. The endophyte present in the Weed population was shown to produce chanoclavine I, paspaline, and terpendoles, so thus resembles the previously described Epichloë funkii. The endophyte present in the Cloudcroft population produces chanoclavineI, ergonovine, lysergic acid amide, and paspaline, and is an undescribed endophyte species. We observed very low survival rates for aphids feeding on plants infected with the Cloudcroft endophyte, while aphid survival was better on endophyte infected plants in the Weed population. This observation led to the hypothesis that the alkaloid ergonovine is responsible for aphid mortality. Direct testing of aphid survival on oat leaves supplemented with ergonovine provided supporting evidence for this hypothesis. The results of this study suggest that alkaloids produced by the Cloudcroft endophyte, specifically ergonovine, have insecticidal properties. PMID:25501262

Shymanovich, Tatsiana; Saari, Susanna; Lovin, Mary E; Jarmusch, Alan K; Jarmusch, Scott A; Musso, Ashleigh M; Charlton, Nikki D; Young, Carolyn A; Cech, Nadja B; Faeth, Stanley H

2015-01-01

482

Optimization of Extraction and Enrichment of Steroidal Alkaloids from Bulbs of Cultivated Fritillaria cirrhosa  

PubMed Central

The bulbs of cultivated Fritillaria cirrhosa (BCFC) are used in China both for food and folk medicine due to its powerful biological activities. The aim of this study is to optimize the extraction and enrichment conditions of alkaloids from BCFC. Firstly, the orthogonal experimental design was used to optimize and evaluate four variables (ethanol concentration, solid-liquid ratio, extraction time, and temperature). Thereafter, resin adsorption was as a means to enrich alkaloids. Among 16 tested resins, H-103 resin presented higher adsorption capacity and desorption ratio. The equilibrium experimental data of the adsorption of total alkaloids, imperialine, and peimisine were well-fitted to the pseudo-first-order kinetics model, Langmuir and Freundlich isotherms models. Finally, in order to optimize the parameters for purifying alkaloids, dynamic adsorption and desorption tests were carried out. After one run treatment with H-103 resin, the contents of total alkaloids, imperialine, and peimisine in the product were 21.40-, 18.31-, and 22.88-fold increased with recovery yields of 94.43%, 90.57%, and 96.16%, respectively. PMID:24804207

Wang, Shu; Du, Qingdan; Wang, Nanyi; Liu, Simei; Wang, Xiaoxia; Jiang, Jinghui

2014-01-01

483

Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors.  

PubMed

Genes encoding regulatory factors isolated from Arabidopsis, soybean and corn have been screened to identify those that modulate the expression of genes encoding for enzymes involved in the biosynthesis of morphinan alkaloids in opium poppy (Papaver somniferum) and benzophenanthridine alkaloids in California poppy (Eschscholzia californica). In opium poppy, the over-expression of selected regulatory factors increased the levels of PsCOR (codeinone reductase), Ps4'OMT (S-adenosyl-l-methionine:3'-hydroxy-N-methylcoclaurine 4'-O-methyltransferase) and Ps6OMT [(R,S)-norcoclaurine 6-O-methyltransferase] transcripts by 10- to more than 100-fold. These transcriptional activations translated into an enhancement of alkaloid production in opium poppy of up to at least 10-fold. In California poppy, the transactivation effect of regulatory factor WRKY1 resulted in an increase of up to 60-fold in the level of EcCYP80B1 [(S)-N-methylcoclaurine 3'-hydroxylase] and EcBBE (berberine bridge enzyme) transcripts. As a result, the accumulations of selected alkaloid intermediates were enhanced up to 30-fold. The transactivation effects of other regulatory factors led to the accumulation of the same intermediates. These regulatory factors also led to the production of new alkaloids in California poppy callus culture. PMID:17961129

Apuya, Nestor R; Park, Joon-Hyun; Zhang, Liping; Ahyow, Maurice; Davidow, Patricia; Van Fleet, Jennifer; Rarang, Joel C; Hippley, Matthew; Johnson, Thomas W; Yoo, Hye-Dong; Trieu, Anthony; Krueger, Shannon; Wu, Chuan-yin; Lu, Yu-ping; Flavell, Richard B; Bobzin, Steven C

2008-02-01

484

Dietary alkaloids and the development of androconial organs in Estigmene acrea  

PubMed Central

Male salt marsh moths, Estigmene acrea (Lepidoptera: Arctiidae), possess inflatable androconial organs called coremata. Prior to mating males form aggregations and inflate their coremata en masse. The communal display attracts additional males and females for the purpose of mating. The coremata are known to carry the plant-derived dihydropyrrolizine, hydroxydanaidal. This pheromonal substance is derived from secondary plant chemicals called pyrrolizidine alkaloids found in the larval diet. When E. acrea larvae were raised on semi-synthetic diets containing different levels of the pyrrolizidine alkaloid precursors the alkaloids triggered a pronounced morphogenetic effect. Adult males that fed on high levels of the pyrrolizidine alkaloid monocrotaline N-oxide (2500 µg) developed the largest coremata. Males that fed on lower levels of monocrotaline N-oxide (500 µg) or no alkaloid, while normal in body weight, had coremata that were progressively smaller and less robust. The size of the coremata and their commensurate pheromonal charge may have behavioral consequences in the unusual mating system of this species. PMID:15841220

Davenport, Jason W.; Conner, William E.

2003-01-01

485

Synthesis and Anticancer Activity of all Known (-)-Agelastatin Alkaloids Page S1/ S35 Sunkyu Han, Dustin S. Siegel, Karen C. Morrison, Paul J. Hergenrother, and Mohammad Movassaghi  

E-print Network

Synthesis and Anticancer Activity of all Known (-)-Agelastatin Alkaloids Page S1/ S35 Sunkyu Han and Anticancer Activity of All Known (­)-Agelastatin Alkaloids Sunkyu Han, Dustin S. Siegel, Karen C. Morrison Spectra S16 #12;Synthesis and Anticancer Activity of all Known (-)-Agelastatin Alkaloids Page S2/ S35

Hergenrother, Paul J.

486

Ergopeptine Alkaloid Production by Endophytes in a Common Tall Fescue Genotype iN. s. Hill,* W.A. Parrott, and D. D. Pope  

E-print Network

Ergopeptine Alkaloid Production by Endophytes in a Common Tall Fescue Genotype iN. s. Hill,* W Battista, 1990); however, the endophyte also pro- duces ergopeptine alkaloids, which are responsible consuming tall rescue herbage. Recent investi- .gations in which ergopeptine alkaloids were infused

Parrott, Wayne

487

Phyrochemrsiry, 1978. Vol 17. p 172 Pergamon Press Pnnted m England ISOLATION OF THE PYRROLIZIDINE ALKALOID EUROPINE N-OXIDE FROM  

E-print Network

ALKALOID EUROPINE N-OXIDE FROM HELIOTROPIUM MARIS-MORTUI AND H. ROTUNDIFOLIUM L. H. ZALKOW*, L. GELBAUM-HeLiotropium maris-mortui; H. rotundifolium; Boraginaceae; pyrrolizidine alkaloid. europine N-oxide. Heliotropium,-H,O. The organic layer contained almost no material and gave no Mattocks test [I] for pyrrolizidine alkaloids

Keinan, Ehud

488

The Actions of Piperidine Alkaloids at Fetal Muscle-Type and Autonomic-Type Nicotinic Acetylcholine Receptors  

Technology Transfer Automated Retrieval System (TEKTRAN)

Piperidine alkaloids are found in many species of plants including Conium maculatum, Nicotiana spp., and Lupinus spp. A pharmacodynamic comparison was made of the alkaloids ammodendrine, anabasine, anabaseine, and coniine in; SH-SY5Y cells which express autonomic-type nicotinic acetylcholine recept...

489

Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine.  

PubMed

An efficient anionic bicyclization of tryptamine-derived Zincke aldehydes forms the basis for a three-step route to the tetracyclic ABCE core of many Strychnos, Aspidosperma, and Iboga alkaloids. This powerful reaction is showcased in a five-step synthesis of the Strychnos alkaloid norfluorocurarine from tryptamine and pyridine. PMID:19236094

Martin, David B C; Vanderwal, Christopher D

2009-03-18

490

An analysis of Sorghum halepense’s behavior in presence of tropane alkaloids from Datura stramonium extracts  

PubMed Central

Background This study aimed to quantify the allelopathic potential of Datura stramonium (Jimson weed). Sorghum halepense (Johnsongrass) tolerance was assessed by germinating, seed and growing seedlings, dosing of photo-synthesis pigments, followed by treatment with D. stramonium extract tropane alkaloids. Results Preliminary chemical analysis of the extracts showed the presence of alkaloids. The presence of alkaloids was confirmed through HPLC–UV system analysis. Various concentrations of analytic purity alkaloids had similar effects on germination and development of S. halepense’s root systems with those of extracts from of D. stramonium. Germination was not affected by any of the tested extracts, but growth was inhibited by the presence of tropane alkaloids. Extracts had effects at higher alkaloid concentrations. Seedlings of S. halepense developed toxicity symptoms in the presence of alkaloid extracts, but the occurrence of several chlorotic and necrotic areas was noticed in the flower extract biotest. Conclusions Results show that the tested species is sensitive to alkaloids in their growth environment. This research justifies the fact that aqueous extracts from D. stramonium are adequate to the situations in which S. halepense becomes damaging. PMID:22839364

2012-01-01

491

Isolation, Identification, and Chemical Synthesis of 6alpha-Hydroxyraumacline: A Novel Alkaloid from Cultivated Rauwolfia serpentina Cells.  

PubMed

From RAUWOLFIA SERPENTINA cells cultivated in the presence of ajmaline ( 2) the new indole alkaloid, 6alpha-hydroxyraumacline ( 1), was isolated. This alkaloid also occurs in significant amounts in the nutrition medium. A simple chemical synthesis of 1 was developed starting from ajmaline ( 2). PMID:17226497

Endreß, S; Suda, S; Takayama, H; Aimi, N; Sakai, S; Stöckigt, J

1992-10-01

492

Hainanerectamines A–C, Alkaloids from the Hainan Sponge Hyrtios erecta  

PubMed Central

Two new indole alkaloids, hainanerectamines A (1) and B (2), and one new ?-carboline alkaloids, hainanerectamines C (4), along with five known related alkaloids (3, 5–8), have been isolated from the Hainan marine sponge Hyrtios erecta. The structures of new compounds 1, 2 and 4 were determined by detailed analysis of their 1D and 2D NMR spectra and by comparison of their spectroscopic data with those of related model compounds. Compounds 2–4 exhibited moderate inhibitory activity against Aurora A, a member of serine/threonine kinase family involving in the regulation of cell division and a new target in cancer treatment, with IC50 values of 24.5, 13.6, and 18.6 ?g/mL, respectively. PMID:24983641

He, Wen-Fei; Xue, Duo-Qing; Yao, Li-Gong; Li, Jing-Ya; Li, Jia; Guo, Yue-Wei

2014-01-01

493

Naucline, a new indole alkaloid from the bark of Nauclea officinalis.  

PubMed

A new indole alkaloid, naucline (1) together with four known alkaloids, angustine (2), angustidine (3), nauclefine (4) and naucletine (5), were isolated from the bark of Nauclea officinalis. The structures of all isolated compounds were elucidated with various spectroscopic methods such as 1D- and 2D- NMR, IR, UV and LCMS-IT-TOF. In addition to that of alkaloid 1, the complete 13C-NMR data of naucletine (5) were also reported. Naucline (1) showed a moderate vasorelaxant activity (90% relaxation at 1 × 10(-5) M) whereas, angustine (2), nauclefine (4), and naucletine (5) showed potent vasorelaxant activity (more than 90% relaxation at 1 × 10(-5) M) on an isolated rat aorta. PMID:22469596

Liew, Sook Yee; Mukhtar, Mat Ropi; Hadi, A Hamid A; Awang, Khalijah; Mustafa, Mohd Rais; Zaima, Kazumasa; Morita, Hiroshi; Litaudon, Marc

2012-01-01

494

Rapid Identification of Enzyme Variants for Reengineered Alkaloid Biosynthesis in Periwinkle  

PubMed Central

Summary Monoterpene indole alkaloids from Catharanthus roseus (Madagascar periwinkle), such as the anticancer agents vinblastine and vincristine, have important pharmacological activities. Metabolic engineering of alkaloid biosynthesis can provide an efficient and environmentally friendly route to analogs of these synthetically challenging and pharmaceutically valuable natural products. However, the narrow substrate scope of strictosidine synthase, the enzyme at the entry point of the pathway, limits a pathway engineering approach. We demonstrate that with a new expression system and screening method it is possible to rapidly identify strictosidine synthase variants that accept tryptamine analogs not turned over by the wild-type enzyme. The variants are used in stereoselective synthe