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1

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

2

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

3

Total Synthesis and Absolute Configuration of the Marine Norditerpenoid Xestenone  

PubMed Central

Xestenone is a marine norditerpenoid found in the northeastern Pacific sponge Xestospongia vanilla. The relative configuration of C-3 and C-7 in xestenone was determined by NOESY spectral analysis. However the relative configuration of C-12 and the absolute configuration of this compound were not determined. The authors have now achieved the total synthesis of xestenone using their developed one-pot synthesis of cyclopentane derivatives employing allyl phenyl sulfone and an epoxy iodide as a key step. The relative and absolute configurations of xestenone were thus successfully determined by this synthesis. PMID:20098605

Ota, Koichiro; Kurokawa, Takao; Kawashima, Etsuko; Miyaoka, Hiroaki

2009-01-01

4

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

5

Bioactive norditerpenoids from the soft coral Sinularia gyrosa.  

PubMed

Chemical investigations of the soft coral Sinularia gyrosa resulted in the isolation of six new norcembranolides, gyrosanolides A-F (1-6), a new norcembrane, gyrosanin A (7), and 11 known norditerpenoids 8-18. The structures of the isolated compounds were elucidated through extensive spectroscopic data and by comparison with reported data in the literature. Compounds 1-3, 7-9, 12, and 13 at concentration of 10microM did not inhibit the COX-2 protein expression, but significantly reduced the levels of the iNOS protein (55.2+/-14.6%, 18.6+/-6.7%, 10.6+/-4.6%, 66.9+/-5.2%, 10.2+/-5.1%, 17.4+/-7.2%, 47.2+/-11.9%, and 56.3+/-5.1%, respectively) by LPS stimulation. Compound 8 showed significant antiviral activity against HCMV (human cytomegalovirus) cells with an IC(50) of 1.9microg/mL. PMID:20430633

Cheng, Shi-Yie; Chuang, Cheng-Ta; Wen, Zhi-Hong; Wang, Shang-Kwei; Chiou, Shu-Fen; Hsu, Chi-Hsin; Dai, Chang-Feng; Duh, Chang-Yih

2010-05-15

6

Yonarolide: a new marine norditerpenoid possessing a novel tricyclic skeleton, from the Okinawan soft coral of the genus, Sinularia  

Microsoft Academic Search

Yonarolide, a new marine norditerpenoid possessing a novel tricyclic skeleton, was isolated from the Okinawan soft coral of the genus, Sinularia. The structure of yonarolide was determined by spectroscopic analysis.

Kazuo Iguchi; Kinzo Kajiyama; Yasuji Yamada

1995-01-01

7

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

8

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

9

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...

10

Pyrrolizidine alkaloids.  

PubMed

This review covers pyrrolizidine alkaloids isolated from natural sources. Topics include: aspects of structure, isolation, and biological/pharmacological studies; total syntheses of necic acids, necine bases and closely-related non-natural analogues. PMID:25158215

Robertson, Jeremy; Stevens, Kiri

2014-12-01

11

Ergot Alkaloids  

Microsoft Academic Search

\\u000a Ergot alkaloids are mycotoxins of agricultural and medical importance produced by at least two different lineages of fungi.\\u000a Fungi from different lineages share early steps of the biosynthetic pathway, and gene knockout studies and genomic analyses\\u000a indicate a common set of clustered genes encodes these early pathway steps. Different taxa follow different terminal branches\\u000a of the pathway to produce profiles

Daniel G. Panaccione

12

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

13

Alkaloids in marine algae  

E-print Network

Abstract: 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.

Kas?m Cemal Güven; Aline Percot; Ekrem Sezik

14

Amaryllidaceae and Sceletium alkaloids.  

PubMed

This review covers the isolation, biological activity and chemical synthesis of Amaryllidaceae alkaloids and the structurally related Sceletium alkaloids. The literature from July 2001 to the end of 2002 is reviewed, and 61 references are cited. PMID:14700202

Jin, Zhong

2003-12-01

15

Amaryllidaceae and Sceletium alkaloids.  

PubMed

This review covers the morphology, isolation, total synthesis and biological activity of the naturally occurring alkaloids isolated from the Amaryllidaceae family, as well as the structurally related Sceletium alkaloids. PMID:15692620

Jin, Zhong

2005-02-01

16

Effects of Larkspur (Delphinium barbeyi) on Heart Rate and Electrically Evoked Electromyographic Response of the External Anal Sphincter in Cattle.  

Technology Transfer Automated Retrieval System (TEKTRAN)

Norditerpenoid alkaloids of larkspur (Delphinium spp.) are competitive antagonists of nicotinic cholinergic receptors and poison cattle with, high mortality. Of the norditerpenoids, the N-(methylsuccinimido) anthranoyllycoctonine type (MSAL-type) alkaloids are most toxic. This study tested the hyp...

17

Amaryllidaceae and Sceletium alkaloids.  

PubMed

A great number of natural products, especially alkaloids, which exhibit a range of biological activities including acetylcholinesterase inhibition and antineoplastic, cardiovascular and immunostimulatory activities, have been isolated from the plants of the Amaryllidaceae family. this review summarizes isolation, biological activity, and synthetic studies of these alkaloids. The primary biosynthetic pathways of each type of alkaloids are also proposed. PMID:17653364

Jin, Zhong

2007-08-01

18

Amaryllidaceae and Sceletium alkaloids.  

PubMed

Structurally diverse alkaloids, which show significant biological activities, are abundant in the plants of the family Amaryllidaceae. The latest progress on the isolation, identification, biological activity, and chemical synthesis of Amaryllidaceae alkaloids and the structurally close Sceletium alkaloids is summarized in this review. PMID:21472174

Jin, Zhong

2011-06-01

19

Signalling molecules and the synthesis of alkaloids in Catharanthus roseus seedlings  

Microsoft Academic Search

The Madagascar periwinkle, Catharanthus roseus, produces numerous alkaloids, several of which have important pharmaceutical uses. Catharanthus seedlings rapidly accumulate the monomeric alkaloids, vindoline, catharanthine and tabersonine, during germination. Various plant signalling molecules were tested for their ability to enhance alkaloid synthesis in Catharanthus seedlings. The compounds tested included plant hormones, fatty acid-derived messengers and agents that can induce systemic-acquired resistance

Rob J. Aerts; Andrea Schäfer; Manfred Hesse; Thomas W. Baumann; Alan Slusarenko

1996-01-01

20

Amaryllidaceae and Sceletium alkaloids.  

PubMed

Alkaloids from the plants of Amaryllidaceae family consists of an unique class of nitrogen-containing compounds showing diverse and significant biological activities, including anticancer and acetylcholinesterase (AChE) inhibitory activities. This review summarizes the research into the isolation, structure elucidation, biological activity, and chemical aspects of the Amaryllidaceae alkaloids over the last two years. In addition, structurally closely related Sceletium alkaloids are also discussed. PMID:19240946

Jin, Zhong

2009-03-01

21

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

22

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

23

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

24

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.

2007-02-12

25

Dimeric Cinchona alkaloids.  

PubMed

Nature is full of dimeric alkaloids of various types from many plant families, some of them with interesting biological properties. However, dimeric Cinchona alkaloids were not isolated from any species but were products of designed partial chemical synthesis. Although the Cinchona bark is amongst the sources of oldest efficient medicines, the synthetic dimers found most use in the field of asymmetric synthesis. Prominent examples include the Sharpless dihydroxylation and aminohydroxylation ligands, and dimeric phase transfer catalysts. In this article the syntheses of Cinchona alkaloid dimers and oligomers are reviewed, and their structure and applications are outlined. Various synthetic routes exploit reactivity of the alkaloids at the central 9-hydroxyl group, quinuclidine, and quinoline rings, as well as 3-vinyl group. This availability of reactive sites, in combination with a plethora of linker molecules, contributes to the diversity of the products obtained. PMID:25586655

Boraty?ski, Przemys?aw J

2015-05-01

26

Biosynthesis of Lycopodium Alkaloids  

Microsoft Academic Search

An investigation of the biosynthesis of lycopodine, the major alkaloid of Lycopodium tristachyum, has revealed that L-lysine, but not D-lysine is incorporated into this alkaloid. D-lysine serves as a precursor to pipecolic acid in this species. Sodium malonate has been demonstrated to be a specific precursor to lycopodine, but attempts to verify the postulated intermediacy of piperidineacetic acid. In the

William D. Marshall

1973-01-01

27

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...

28

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

29

Hypotensive Alkaloids of Veratrum album  

Microsoft Academic Search

INVESTIGATIONS on alkaloids of Veratrum viride necessitated the preparation of a pure specimen of protoveratrine and prompted an examination of the alkaloids which could be isolated from commercial samples of Veratrum album. As a result of these studies, we now report the isolation of two new hypotensive ester alkaloids which have been named `germitetrine' and `veratetrine'.

William L. Glen; Gordon S. Myers; Richard Barber; Paul Morozovitch; Gordon A. Grant

1952-01-01

30

Alkaloids Toxic to Livestock  

Technology Transfer Automated Retrieval System (TEKTRAN)

Alkaloids are a specific group of nitrogen-containing natural metabolites that enable plants to overcome temporary or continuous threats integral to their environment, while also controlling essential functions of growth and reproduction. These compounds are probably produced primarily to control f...

31

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

32

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

33

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

34

Four alkaloids from Annona cherimola  

Microsoft Academic Search

Four alkaloids, annocherine A, annocherine B, cherianoine, and romucosine H, along with one known alkaloid, artabonatine B, were isolated from the MeOH extract of the stems of Annona cherimola. Their structures were identified on the basis of both analysis of their spectral data and from chemical evidence.

Chung-Yi Chen; Fang-Rong Chang; Wen-Bin Pan; Yang-Chang Wu

2001-01-01

35

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

36

Testing chemical defence based on pyrrolizidine alkaloids  

Microsoft Academic Search

Pyrrolizidine alkaloids are considered the primary defence mechanism in aposematic ithomiine butterflies and arctiid moths. Despite evidence that pyrrolizidine alkaloids are effective against some invertebrate predators, proof for a protective function of pyrrolizidine alkaloids against vertebrate predators is fragmented. The present work shows that the pyrrolizidine alkaloid monocrot-aline is unpalatable to the pileated finch,Coryphospingus pileatusand that the unpalatability is learned

MÁRCIO ZIKÁN CARDOSO

1997-01-01

37

Bioactive montanine derivatives from halide-induced rearrangements of haemanthamine-type alkaloids. Absolute configuration by VCD.  

PubMed

An unexpected rearrangement of haemanthamine-type alkaloids in the presence of halogenating agents has been found. Rearranged compounds present the 5,11-methanomorphantridine framework characteristic of montanine-type alkaloids. These compounds are difficult to obtain because of their scarcity in natural sources and because the synthetic approaches developed so far require numerous steps. Vibrational circular dichroism (VCD) spectroscopy was used to determine the absolute configuration of one of the rearranged compounds. Several rearranged alkaloids showed antimalarial activity. PMID:19320502

Cedrón, Juan C; Estévez-Braun, Ana; Ravelo, Angel G; Gutiérrez, David; Flores, Ninoska; Bucio, María A; Pérez-Hernández, Nury; Joseph-Nathan, Pedro

2009-04-01

38

Alkaloids from Macoubea guianensis seeds.  

PubMed

From the seeds of Macoubea guianensis (Apocynaceae), mixtures of the antipodes of two indole alkaloids, vincadifformine and vincadine, have been isolated; in the first the (+)- and in the second the (-)-isomer predominated. PMID:4094465

Anderson, L A; Bisset, N G; Phillipson, J D; Zarucchi, J L

1985-01-01

39

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

40

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

41

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

42

The evolution of pyrrolizidine alkaloid biosynthesis and diversity in the Senecioneae  

Microsoft Academic Search

Pyrrolizidine alkaloids are characteristic secondary metabolites of the Asteraceae and some other plant families. They are\\u000a especially numerous and diverse in the tribe Senecioneae and form a powerful defense mechanism against herbivores. Studies\\u000a into the evolution of pyrrolizidine alkaloid biosynthesis using Senecio species have identified homospermidine synthase as the enzyme responsible for the synthesis of the first specific intermediate.\\u000a These

Dorothee Langel; Dietrich Ober; Pieter B. Pelser

2011-01-01

43

Seven imidazole alkaloids from Lepidium sativum  

Microsoft Academic Search

The seeds of Lepidium sativum afforded five new dimeric imidazole alkaloids lepidine B, C, D, E and F in addition to the known imidazole alkaloid lepidine and two new monomeric imidazole alkaloids semilepidinoside A and B. Their structure were elucidated on the basis of spectroscopic evidence.

Ulrich H Maier; Heidrun Gundlach; Meinhart H Zenk

1998-01-01

44

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

45

27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2014 CFR

...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

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

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

48

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

49

Stem bark alkaloids of Rauvolfia caffra.  

PubMed

Thirty two alkaloids were isolated from the stem bark of Rauvolfia caffra and 28 were identified. The alkaloids represented corynane (3), strictamine (1), sarpagan (4), akuammicine (2), pleiocarpamine (1), indolenine (1), dihydroindole (6), peraksine (3), heteroyohimbine (2), hydroxyheteroyohimbine (2), oxindole (1), 2-acyl-indole (1), suaveoline (3) and yohimbine (2) types. The anhydronium base serpentine was detected but not isolated. The principal alkaloids were ajmaline and norajmaline (dihydroindoles), ajmalicinine and ajmalicine (heteroyohimbines), geissoschizol (E-seco indole) and pleiocarpamine and the heteroyohimbine derived alkaloids were predominantly normal configuration compounds. The biosynthetic and ethnopharmacological significance of the alkaloids is discussed. PMID:6471882

Nasser, A M; Court, W E

1984-06-01

50

Potentiation of the actions of acetylcholine, epibatidine, and nicotine by methyllycaconitine at fetal muscle-type nicotinic acetylcholine receptors  

Technology Transfer Automated Retrieval System (TEKTRAN)

Norditerpenoid alkaloids from Delphinium spp. (larkspur) have been described as possessing “curariform-like” activity in cattle and are of economic importance because of the poisonings they cause. Methyllycaconitine (MLA) is a norditerpenoid alkaloid found in high abundance in toxic larkspur, and i...

51

Steroidal alkaloids from Veratrum album  

Microsoft Academic Search

Two new steroidal alkaloids, veramanine and neojerminalanine, have been isolated from the rhizomes of Veratrum album, along with the known glycoalkaloid, pseudojervine, whose NMR spectral data are reported for the first time. The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic investigations.

Atta-ur-Rahman; Rahat A. Ali; M. Ashraf; M. Iqbal Choudhary; Bilge Sener; Songul Turkoz

1996-01-01

52

Biological activity of alkaloids from Solanum dulcamara L  

Microsoft Academic Search

Alkaloids are well known for their antimicrobial activity. Though all natural alkaloids come from plants, not all plants produce alkaloids. Plants of the Solanaceae family are known for their high alkaloid content. Alkaloids are found in all plant parts like roots, stems, leaves, flowers, fruits and seeds. In the present study, those plant parts of Solanum dulcamara were selected which

Padma Kumar; Bindu Sharma; Nidhi Bakshi

2009-01-01

53

Ergot alkaloid transport across ruminant gastric tissues.  

PubMed

Ergot alkaloids cause fescue toxicosis when livestock graze endophyte-infected tall fescue. It is generally accepted that ergovaline is the toxic component of endophyte-infected tall fescue, but there is no direct evidence to support this hypothesis. The objective of this study was to examine relative and potential transport of ergoline and ergopeptine alkaloids across isolated gastric tissues in vitro. Sheep ruminal and omasal tissues were surgically removed and placed in parabiotic chambers. Equimolar concentrations of lysergic acid, lysergol, ergonovine, ergotamine, and ergocryptine were added to a Kreb's Ringer phosphate (KRP) solution on the mucosal side of the tissue. Tissue was incubated in near-physiological conditions for 240 min. Samples were taken from KRP on the serosal side of the chambers at times 0, 30, 60, 120, 180, and 240 min and analyzed for ergot alkaloids by competitive ELISA. The serosal KRP remaining after incubation was freeze-dried and the alkaloid species quantified by HPLC. The area of ruminal and omasal tissues was measured and the potential transportable alkaloids calculated by multiplying the moles of transported alkaloids per square centimeter of each tissue type by the surface area of the tissue. Studies were conducted to compare alkaloid transport in reticular, ruminal, and omasal tissues and to determine whether transport was active or passive. Ruminal tissue had greater ergot alkaloid transport potential than omasal tissue (85 vs 60 mmol) because of a larger surface area. The ruminal posterior dorsal sac had the greatest potential for alkaloid transport, but the other ruminal tissues were not different from one another. Alkaloid transport was less among reticular tissues than among ruminal tissues. Transport of alkaloids seemed to be an active process. The alkaloids with greatest transport potential were lysergic acid and lysergol. Ergopeptine alkaloids tended to pass across omasal tissues in greater quantities than across ruminal tissues, but their transport was minimal compared to lysergic acid and lysergol. PMID:11219466

Hill, N S; Thompson, F N; Stuedemann, J A; Rottinghaus, G W; Ju, H J; Dawe, D L; Hiatt, E E

2001-02-01

54

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

55

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

56

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

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, 2014 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...

2014-04-01

60

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

61

Imidazole alkaloids from Lepidium meyenii.  

PubMed

Two new imidazole alkaloids (lepidiline A and lepidiline B) have been isolated from a root extract of Lepidium meyenii with the common name Maca and identified as 1,3-dibenzyl-4,5-dimethylimidazolium chloride (1) and 1,3-dibenzyl-2,4,5-trimethylimidazolium chloride (2), respectively. The structures of these two new compounds were determined by spectroscopic methods, as well as single-crystal X-ray diffraction performed on compound 1. PMID:12932133

Cui, Baoliang; Zheng, Bo Lin; He, Kan; Zheng, Qun Yi

2003-08-01

62

Pyrrolizidine alkaloids from Onosma erecta.  

PubMed

The MeOH extract of the aerial parts of Onosma erecta afforded four new pyrrolizidine alkaloids, 7-O-acetylechinatine N-oxide (1), a viridinatine N-oxide stereoisomer (2), 7-epi-echimiplatine N-oxide (3), and onosmerectine N-oxide (4), and two additional new natural products, the acid 2,3-dimethyl-2,3,4-trihydroxypentanoic acid (5) and the acyloin 4-methyl-2-hydroxypentanone (6). PMID:24107229

Damianakos, Harilaos; Sotiroudis, Georgios; Chinou, Ioanna

2013-10-25

63

Piperidine alkaloids from Piper methysticum  

Microsoft Academic Search

Pipermethystine (1), 3?,4?-epoxy-5?-pipermethystine (2) and awaine (3) were isolated from the aerial parts of kava (Piper methysticum G. Forster, Piperaceae) and identified by HRMS and NMR spectroscopic analysis. 1 was concentrated in the stem peelings and leaves. 2 and 3 are new alkaloids with 2 found only in cv. Isa among the 11 cultivars examined, and 3 occurred primarily in

Klaus Dragull; Wesley Y. Yoshida; Chung-Shih Tang

2003-01-01

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

De novo production of the plant-derived alkaloid strictosidine in yeast  

PubMed Central

The monoterpene indole alkaloids are a large group of plant-derived specialized metabolites, many of which have valuable pharmaceutical or biological activity. There are ?3,000 monoterpene indole alkaloids produced by thousands of plant species in numerous families. The diverse chemical structures found in this metabolite class originate from strictosidine, which is the last common biosynthetic intermediate for all monoterpene indole alkaloid enzymatic pathways. Reconstitution of biosynthetic pathways in a heterologous host is a promising strategy for rapid and inexpensive production of complex molecules that are found in plants. Here, we demonstrate how strictosidine can be produced de novo in a Saccharomyces cerevisiae host from 14 known monoterpene indole alkaloid pathway genes, along with an additional seven genes and three gene deletions that enhance secondary metabolism. This system provides an important resource for developing the production of more complex plant-derived alkaloids, engineering of nonnatural derivatives, identification of bottlenecks in monoterpene indole alkaloid biosynthesis, and discovery of new pathway genes in a convenient yeast host. PMID:25675512

Brown, Stephanie; Clastre, Marc; Courdavault, Vincent; O’Connor, Sarah E.

2015-01-01

67

De novo production of the plant-derived alkaloid strictosidine in yeast.  

PubMed

The monoterpene indole alkaloids are a large group of plant-derived specialized metabolites, many of which have valuable pharmaceutical or biological activity. There are ?3,000 monoterpene indole alkaloids produced by thousands of plant species in numerous families. The diverse chemical structures found in this metabolite class originate from strictosidine, which is the last common biosynthetic intermediate for all monoterpene indole alkaloid enzymatic pathways. Reconstitution of biosynthetic pathways in a heterologous host is a promising strategy for rapid and inexpensive production of complex molecules that are found in plants. Here, we demonstrate how strictosidine can be produced de novo in a Saccharomyces cerevisiae host from 14 known monoterpene indole alkaloid pathway genes, along with an additional seven genes and three gene deletions that enhance secondary metabolism. This system provides an important resource for developing the production of more complex plant-derived alkaloids, engineering of nonnatural derivatives, identification of bottlenecks in monoterpene indole alkaloid biosynthesis, and discovery of new pathway genes in a convenient yeast host. PMID:25675512

Brown, Stephanie; Clastre, Marc; Courdavault, Vincent; O'Connor, Sarah E

2015-03-17

68

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

69

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

70

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

71

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

72

Alkaloids as Possible Intermediaries in Plant Metabolism  

Microsoft Academic Search

SINCE their discovery 150 years ago, alkaloids have been the subject of innumerable research papers, practically all of which have been concerned with the occurrence, production in the plant and properties of the final molecular species. Even when the plant produces a series of closely related alkaloids, it has normally been considered sufficient to show their order of formation and

J. W. Fairbairn; A. Paterson

1966-01-01

73

Halogenated Indole Alkaloids from Marine Invertebrates  

PubMed Central

This review discusses the isolation, structural elucidation, and biological activities of halogenated indole alkaloids obtained from marine invertebrates. Meridianins and related compounds (variolins, psammopemmins, and aplicyanins), as well as aplysinopsins and leptoclinidamines, are focused on. A compilation of the 13C-NMR spectral data of these selected natural indole alkaloids is also provided. PMID:20559487

Pauletti, Patrícia Mendonça; Cintra, Lucas Silva; Braguine, Caio Guedes; da Silva Filho, Ademar Alves; Silva, Márcio Luís Andrade e; Cunha, Wilson Roberto; Januário, Ana Helena

2010-01-01

74

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

75

Piperidine alkaloids: human and food animal teratogens.  

PubMed

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 teratogenic piperidine alkaloids include poison hemlock (Conium maculatum), lupine (Lupinus spp.), and tobacco (Nicotiana tabacum) [including wild tree tobacco (Nicotiana glauca)]. There is abundant epidemiological evidence in humans that link maternal tobacco use with a high incidence of oral clefting in newborns; this association may be partly attributable to the presence of piperidine alkaloids in tobacco products. In this review, we summarize the evidence for piperidine alkaloids that act as teratogens in livestock, piperidine alkaloid structure-activity relationships and their potential implications for human health. PMID:22449544

Green, Benedict T; Lee, Stephen T; Panter, Kip E; Brown, David R

2012-06-01

76

Iboga-Type Alkaloids from Ervatamia officinalis.  

PubMed

Seven new iboga-type alkaloids, ervaoffines A-D (1-4), (7S)-3-oxoibogaine hydroxyindolenine (5), ibogaine-5,6-dione (6), and 19-epi-5-oxovoacristine (7), and 10 known alkaloids were isolated from Ervatamia officinalis. The absolute configurations of 1-7 were determined through X-ray diffraction and electronic circular dichroism (ECD) analyses. Ervaoffines A and B represent the first iboga-type pseudoindoxyl alkaloids in which the C-2 spiro carbon configuration is opposite to that of other members of this class, such as iboluteine (8). The relationship between the absolute configuration of the spiro carbons and the Cotton effect in the ECD spectrum is established for the first time for iboga-type pseudoindoxyl and oxindole alkaloids. Additionally, a plausible biogenetic pathway for these alkaloids is proposed. PMID:25093992

Tang, Ben-Qin; Wang, Wen-Jing; Huang, Xiao-Jun; Li, Guo-Qiang; Wang, Lei; Jiang, Ren-Wang; Yang, Ting-Ting; Shi, Lei; Zhang, Xiao-Qi; Ye, Wen-Cai

2014-08-01

77

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

78

Genetic variation in alkaloid accumulation in leaves of Nicotiana *  

PubMed Central

Alkaloids are plant secondary metabolites that are widely distributed in Nicotiana species and contribute greatly to the quality of tobacco leaves. Some alkaloids, such as nornicotine and myosmine, have adverse effects on human health. To reduce the content of harmful alkaloids in tobacco leaves through conventional breeding, a genetic study of the alkaloid variation among different genotypes is required. In this study, alkaloid profiles in leaves of five Nicotiana tabacum cultivars and Nicotiana tomentosiformis were investigated. Six alkaloids were identified from all six genotypes via gas chromatograph-mass spectrometry (GC-MS). Significant differences in alkaloid content were observed both among different leaf positions and among cultivars. The contents of nornicotine and myosmine were positively and significantly correlated (R 2=0.881), and were also separated from those of other alkaloids by clustering. Thus, the genotype plays a major role in alkaloid accumulation, indicating a high potential for manipulation of alkaloid content through traditional breeding. PMID:24302710

Sun, Bo; Zhang, Fen; Zhou, Guo-jun; Chu, Guo-hai; Huang, Fang-fang; Wang, Qiao-mei; Jin, Li-feng; Lin, Fu-cheng; Yang, Jun

2013-01-01

79

4-Quinolone Alkaloids from Melochia odorata  

PubMed Central

The methanol extract of Melochia odorata yielded three 4-quinolone alkaloids including waltherione A (1) and two new alkaloids, waltherione C (2) and waltherione D (3). Waltheriones A and C showed significant activities in an in vitro anti-HIV cytoprotection assay at concentrations of 56.2 and 0.84 ?M, and inhibition of HIV P24 formation of more than 50% at 1.7 and 0.95 ?M, respectively. The structures of the alkaloids were established by spectroscopic data interpretation. PMID:24392742

Jadulco, Raquel C.; Pond, Christopher D.; Van Wagoner, Ryan M.; Koch, Michael; Gideon, Osia G.; Matainaho, Teatulohi K.; Piskaut, Pius; Barrows, Louis R.

2014-01-01

80

A case of beta-carboline alkaloid intoxication following ingestion of Peganum harmala seed extract.  

PubMed

Beta-carboline alkaloids harmine, harmaline, and tetrahydroharmine can stimulate the central nervous system by inhibiting the metabolism of amine neurotransmitters, or by direct interaction with specific receptors; they are found in numerous plants, including Peganum harmala, Passiflora incarnata and Banisteriopsis caapi, and in the entheogen preparation Ayahuasca, which is traditionally brewed using B. caapi to enhance the activity of amine hallucinogenic drugs. The ingestion of plant preparations containing beta-carboline alkaloids may result in toxic effects, namely visual and auditory hallucinations, locomotor ataxia, nausea, vomiting, confusion and agitation. We report a case of intoxication following intentional ingestion of P. harmala seed infusion; P. harmala seeds were bought over the Internet. The harmala alkaloids were identified by gas chromatography-mass spectrometry in the seed extract and the patient's urine. This is, to our knowledge, the first case of P. harmala intoxication corroborated by toxicological findings. PMID:18603389

Frison, Giampietro; Favretto, Donata; Zancanaro, Flavio; Fazzin, Giorgio; Ferrara, Santo Davide

2008-08-01

81

Pyrrolizidine alkaloids in Pulmonaria obscura.  

PubMed

Leaves, roots and rhizomes, and inflorescenses of Pulmonaria obscura from two localities and of two different growth forms within one site were analyzed by GC-MS for their content in pyrrolizidine alkaloids (PAs). In roots and rhizomes PAs of the lycopsamine type typical for the Boraginaceae could be detected, e. g. intermedine, lycopsamine, and their O(7)-derivatives. The total PA concentrations in roots and rhizomes lay between 0.026 and 0.158 mg/g dry weight. In leaves and inflorescenses, on the other hand, only trace amounts of PAs (below 0.4 ng/mg dry weight) could be detected. No significant differences in total concentration of PAs could be found between the two sites. PMID:12058336

Haberer, W; Witte, L; Hartmann, Th; Dobler, S

2002-05-01

82

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

83

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...

84

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.

85

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

86

Synthesis and anticancer activity of epipolythiodiketopiperazine alkaloids  

E-print Network

The epipolythiodiketopiperazine (ETP) alkaloids are a highly complex class of natural products with potent anticancer activity. Herein, we report the application of a flexible and scalable synthesis, allowing the construction ...

Boyer, Nicolas

87

Loline alkaloids: Currencies of mutualism.  

PubMed

Several species of Lolium and other cool-season grasses (Poaceae subfamily Pooideae) tend to harbor symbiotic, seed-transmitted, fungi that enhance their fitness by various means. These fungal endophytes--species of Neotyphodium or Epichloë (Clavicipitaceae)--are known for production of antiherbivore metabolites such as the bioprotective loline alkaloids. Lolines are saturated pyrrolizidines with an exo-1-amine and an ether bridge between C-2 and C-7. The ether bridge is an unusual feature for a biogenic compound in that it links two bridgehead carbon atoms. Much of the loline-biosynthetic pathway has been elucidated by administering isotopically labeled precursors to fungal cultures and by comparisons of loline biosynthesis genes to known gene families. The first step appears to be an unusual gamma-substitution reaction involving an enzyme related to O-acetylhomoserine (thiol) lyase, but which uses the secondary amine of L-proline rather than a sulfhydryl group as the nucleophile. The strained ether bridge is added after formation of the pyrrolizidine rings. Lolines with dimethylated or acylated 1-amines have insect antifeedant and insecticidal activities comparable to nicotine, but little or no toxicity to mammals. Considering the surprising abundance of lolines in some grass-endophyte symbiota, possible additional effects on plant stress tolerance and physiology are worth future consideration. In this review, we discuss the history of loline discovery, methods of analysis, biological activities and distribution in nature, as well as progress on the genetics and biochemistry of their biosynthesis, and on the chemical synthesis of these alkaloids. PMID:17346759

Schardl, Christopher L; Grossman, Robert B; Nagabhyru, Padmaja; Faulkner, Jerome R; Mallik, Uma P

2007-04-01

88

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

89

Alkaloids from Aspidosperma species from Bolivia.  

PubMed

Two Bolivian Aspidosperma species were investigated. The seed and stem bark of Aspidosperma macrocarpon Mart. contain six known alkaloids: (-)-vincadifformine, ervinceine, kopsanone, kopsinine, kopsanol in the seed, and kopsanone, kopsinine, kopsanol, 18-epikopsanol in the stem bark. The stem bark of Aspidosperma pyrifolium Mart. contains eleven known alkaloids: (-)-vincadifformine, O-demethylpalosine, haplocine, N-formylaspidospermidine, vallesine, demethoxyaspidospermine, palosine, (-)-aspidospermine, aspidospermidine, akuammicine, tubotaiwine, beside the two new bases dehydroxyhaplocidine and 10-methoxyaspidospermidine. PMID:17252481

Mitaine, A C; Mesbah, K; Richard, B; Petermann, C; Arrazola, S; Moretti, C; Zèches-Hanrot, M; Men-Olivier, L L

1996-10-01

90

[Monomeric Indole Alkaloids from Kopsia officinalis.].  

PubMed

Ten monomeric indole alkaloids have been identified from the roots of KOPSIA OFFICINALIS. Four of them are known: (-)-kopsinine 1, (+)-5,22-dioxokopsane 2, (-)-tetrahydroalstonine 4, and (-)-quebrachamine 3; and six are new: (-)-isoeburnamine 5 (enantiomer of the known alkaloid (+)-isoeburnamine), (-)-N-methoxycarbonyl-12-methoxykopsinaline 7, (-)-N-methoxycarbonyl-11,12-methylenedioxy kopsinaline 8, (-)-N-methoxycarbonyl-11,12-dimethoxykopsinaline 9, (-)-11,12-methylenedioxykopsinaline 10, and (-)-12-methoxykopsinaline 11. PMID:17404997

Feng, X Z; Kan, C; Potier, P; Kan, S K; Lounasmaa, M

1983-08-01

91

HELIOTROPIUM EUROPAEUM ALKALOIDS: A QUATERNARY PYRROLIZIDINE ALKALOID APPROACH TO ELISA DEVELOPMENT  

Technology Transfer Automated Retrieval System (TEKTRAN)

Heliotropium europaeum has proven to be an agricultural pest capable of killing stock and severely reducing productivity due to its pyrrolizidine alkaloid content. Existing methods for the detection of pyrrolizidine alkaloids present in H. europaeum include an ELISA and HPLC-MS. The ELISA does not d...

92

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

93

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

94

Human alkaloid biosynthesis : chemical inducers of Parkinson's disease?  

E-print Network

The occurrence of certain alkaloids in the human brain appears to be associated with the onset of Parkinson's disease (PD). Recently, a human protein bearing homology to an alkaloid synthase in plants was identified. This ...

Hatzios, Stavroula K. (Stavroula-Artemis K.)

2005-01-01

95

Biological activity of alkaloids from Solanum dulcamara L.  

PubMed

Alkaloids are well known for their antimicrobial activity. Though all natural alkaloids come from plants, not all plants produce alkaloids. Plants of the Solanaceae family are known for their high alkaloid content. Alkaloids are found in all plant parts like roots, stems, leaves, flowers, fruits and seeds. In the present study, those plant parts of Solanum dulcamara were selected which have been reported to produce a high content of a specific alkaloid: solanine (from unripe fruits), solasodine (from flowers) and beta-solamarine (from roots). These alkaloids were extracted from various parts of S. dulcamara by well-established methods and were screened for their antibacterial activity. Human pathogenic bacteria, viz., Enterobacter aerogenes, Escherichia coli, Staphylococcus aureus, were selected for the study. All three alkaloids inhibited the growth of E. coli and S. aureus. However, no significant activity was observed against E. aerogenes. Minimum inhibitory concentration and minimum bactericidal concentration were also evaluated. PMID:19418354

Kumar, Padma; Sharma, Bindu; Bakshi, Nidhi

2009-01-01

96

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...

97

Production of tropane alkaloids in cultured cells of Hyoscyamus niger  

Microsoft Academic Search

Tests for calluses rich in tropane alkaloids were made with newly induced calluses of Atropa belladonna, Datura stramonium and Hyoscyamus niger. Only calluses of H. niger gave an alkaloid-positive test.

Yasuyuki Yamada; Takashi Hashimoto

1982-01-01

98

Multicomponent Therapeutics of Berberine Alkaloids  

PubMed Central

Although berberine alkaloids (BAs) are reported to be with broad-spectrum antibacterial and antiviral activities, the interactions among BAs have not been elucidated. In the present study, methicillin-resistant Staphylococcus aureus (MRSA) was chosen as a model organism, and modified broth microdilution was applied for the determination of the fluorescence absorption values to calculate the anti-MRSA activity of BAs. We have initiated four steps to seek the optimal combination of BAs that are (1) determining the anti-MRSA activity of single BA, (2) investigating the two-component combination to clarify the interactions among BAs by checkerboard assay, (3) investigating the multicomponent combination to determine the optimal ratio by quadratic rotation-orthogonal combination design, and (4) in vivo and in vitro validation of the optimal combination. The results showed that the interactions among BAs are related to their concentrations. The synergetic combinations included “berberine and epiberberine,” “jatrorrhizine and palmatine” and “jatrorrhizine and coptisine”; the antagonistic combinations included “coptisine and epiberberine”. The optimal combination was berberine?:?coptisine?:?jatrorrhizine?:?palmatine?:?epiberberine = 0.702?:?0.863?:?1?:?0.491?:?0.526, and the potency of the optimal combination on cyclophosphamide-immunocompromised mouse model was better than the natural combinations of herbs containing BAs. PMID:23634170

Luo, Jiaoyang; Yan, Dan; Yang, Meihua; Dong, Xiaoping; Xiao, Xiaohe

2013-01-01

99

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

100

Alkaloids in ergot found on different Gramineae in The Netherlands  

Microsoft Academic Search

The alkaloid content and the composition of the alkaloid complex of thirteen samples of ergot sclerotia from different gramineous\\u000a host species collected in The Netherlands were investigated. Two samples collected in France were also examined. Ergot ofGlyceria fluitans (L.) R.Br. did not contain alkaloids. The total alkaloid content of ergot found on the other wild grasses was more than 0.2%.

A. Reicher; E. T. Elema; J. H. Zwaving; Th. M. Malingré

1983-01-01

101

Amaryllidaceae, sceletium, imidazole, oxazole, thiazole, peptide and miscellaneous alkaloids.  

PubMed

This review covers alkaloids classified in the plant families Amaryallidaceae and Sceletium. In addition alkaloids possessing imidazole, oxazole and thiazole structures are listed followed by alkaloids possessing peptide linkages. Finally miscellaneous alkaloids include those compounds found naturally which cannot be classified into known groups; a relative Pandora's box. A total of 620 structures has been reviewed from 218 references found in the literature for the period July 1999 to June 2000. PMID:12013279

Lewis, John R

2002-04-01

102

Production of tropane alkaloids in cultured cells of Hyoscyamus niger.  

PubMed

Tests for calluses rich in tropane alkaloids were made with newly induced calluses of Atropa belladonna, Datura stramonium and Hyoscyamus niger. Only calluses of H. niger gave an alkaloid-positive test.A Hyoscyamus cell line had the highest total alkaloid content of all the calluses screened by the cell-squash alkaloid assay. Both hyoscyamine and scopolamine were identified in the cultured cells of this line by TLC, GLC and GC-MS. PMID:24259019

Yamada, Y; Hashimoto, T

1982-04-01

103

Hemlock alkaloids from Socrates to poison aloes.  

PubMed

Hemlock (Conium maculatum L. Umbelliferae) has long been known as a poisonous plant. Toxicity is due to a group of piperidine alkaloids of which the representative members are coniine and gamma-coniceine. The latter is the more toxic and is the first formed biosynthetically. Its levels in relation to coniine vary widely according to environmental conditions and to provenance of the plants. Surprisingly, these piperidine alkaloids have turned up in quite unrelated species in the monocotyledons as well as the dicotyledons. Aloes, for instance, important medicinal plants, are not regarded as poisonous although some species are very bitter. Nevertheless a small number of mostly local species contain the alkaloids, especially gamma-coniceine and there have been records of human poisoning. The compounds are recognized by their characteristic mousy smell. Both acute and chronic symptoms have been described. The compounds are neurotoxins and death results from respiratory failure, recalling the effects of curare. Chronic non-lethal ingestion by pregnant livestock leads to foetal malformation. Both acute and chronic toxicity are seen with stock in damp meadows and have been recorded as problems especially in North America. The alkaloids derive biosynthetically from acetate units via the polyketide pathway in contrast to other piperidine alkaloids which derive from lysine. PMID:15955542

Reynolds, Tom

2005-06-01

104

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

105

Pancratium canariense as an important source of amaryllidaceae alkaloids.  

PubMed

Four new alkaloids (1-4) have been isolated from a methanolic extract of bulbs of Pancratium canariense, together with 12 known alkaloids (5-16). The structures of the new alkaloids were determined by extensive 1D and 2D NMR spectroscopic studies and X-ray diffraction. PMID:19072313

Cedrón, Juan C; Oberti, Juan C; Estévez-Braun, Ana; Ravelo, Angel G; Del Arco-Aguilar, Marcelino; López, Matías

2009-01-01

106

Pyrrolizidine alkaloids from Canarian endemic plants and their biological effects  

Microsoft Academic Search

Pyrrolizidine alkaloid (PA) producing plants belonging to the Boraginaceae (Echium wildpretti) and Asteraceae (Canariothamnus palmensis, Kleinia neriifolia, Pericallis appendiculata, Pericallis echinata, Pericallis hansenii, Pericallis multiflora, Pericallis steetzii and Senecio bollei) were selected to study their alkaloidal composition and the defensive properties (antifeedant and phytotoxic effects) of their ethanolic and alkaloidal extracts plus their isolated PAs against insects (Spodoptera littoralis, Leptinotarsa

Dulce M. Domínguez; Matías Reina; Arnoldo Santos-Guerra; Omar Santana; Teresa Agulló; Carmen López-Balboa; Azucena Gonzalez-Coloma

2008-01-01

107

Defensive alkaloid in blood of Mexican bean beetle ( Epilachna varivestis )  

Microsoft Academic Search

Summary The blood of the Mexican bean beetle (Epilachna varivestis) contains a homotropane alkaloid, euphococcinine (1). The beetles ‘reflex bleed’ when disturbed, thereby deploying the alkaloid, which is provenly deterrent to spiders and ants. Newly emerged adults lack the alkaloid, but the compound builds up to deterrent levels in their blood within days. Eggs and larvae ofEpilachna are devoid of

T. Eisner; M. Goetz; D. Aneshansley; G. Ferstandig-Arnold; J. Meinwald

1986-01-01

108

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.

109

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

110

GC\\/MS Examination of Lycopodium Extracts for Alkaloid Content  

Microsoft Academic Search

Plants of the Lycopodium species have long been known to elaborate alkaloids. Over one hundred alkaloids have been isolated from these plants, but no efficient method exists to quickly screen plants to determine their alkaloid content. In this research it has been found that gas chromatography mass spectrometry. (GC\\/MS) is a suitable method to achieve this purpose. Seven species of

Robert V. Gerard

1985-01-01

111

Alkaloid profile and antimicrobial activity of Lupinus angustifolius L. alkaloid extract  

Microsoft Academic Search

Purpose of the present study was to evaluate alkaloid profile of the aerial parts of Lupinus angustifolius growing in Turkey by capillary gas chromatography-mass spectrometry (GC-MS). Fifteen alkaloids were identified by capillary\\u000a GC-MS. 13?-Hydroxylupanine (50.78%) and lupanine (23.55%) were determined as the main alkaloids in the aerial parts of L. angustifolius. Ammodendrine, isoangustifoline, tetrahydrorhombifoline, angustifoline, ?-isolupanine, 5,6-dehydrolupanine, 11,12-dehydrolupanine,\\u000a 13?-acetoxylupanine, 13?-isovaleroyloxylupanine,

Nurgun Erdemoglu; Semiha Ozkan; Fatma Tosun

2007-01-01

112

Ether bridge formation in loline alkaloid biosynthesis.  

PubMed

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 an 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

2014-02-01

113

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

114

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

115

Analysis of toxic alkaloids in body samples.  

PubMed

Many plants contain toxic alkaloids which may be dangerous to humans. Despite the large number of poisonous plants, cases of fatal plant poisonings are relatively rare. The frequencies of poisonings and the plants involved are often regionally specific. Plant poisonings can be aggregated into three categories: unintended ingestions, intended ingestions, and poisoning due to abuse of plant material. Unintended ingestions often occur in children or from a mix-up of plants and mushrooms in adults. Intended ingestions are common in homicides and suicides. Increasingly common is the abuse of plants for hallucinogenic reasons. Toxicological analysis of such alkaloids may help in diagnosis of poisoning or abuse cases. This review describes the toxic alkaloids aconitine, atropine, coniine, colchicine, cytisine, dimethyltryptamine, harmine, harmaline, ibogaine, kawain, mescaline, scopolamine, and taxine, which are often involved in fatal and non-fatal poisonings. The paper summarizes the symptoms of the intoxications and reviews the methods of detection of their toxic constituents in biological fluids. PMID:19147309

Beyer, Jochen; Drummer, Olaf H; Maurer, Hans H

2009-03-10

116

Antitussive indole alkaloids from Kopsia hainanensis.  

PubMed

Three new indole alkaloids, named kopsihainins A-C (1-3), and two known compounds, kopsinine (4) and methyl demethoxycarbonylchanofruticosinate (5), were isolated from the stems of Kopsia hainanensis. Their structures were determined using extensive spectroscopic methods. The two main constituents 4 and 5 exhibited significant antitussive activity in a citric acid induced guinea pig cough model. The antitussive effect of 4 was demonstrated to interact with the ?-opioid receptor. This is the first report of antitussive effects of aspidofractinine type and chanofruticosinate type alkaloids. PMID:21165819

Tan, Min-Jia; Yin, Chun; Tang, Chun-Ping; Ke, Chang-Qiang; Lin, Ge; Ye, Yang

2011-06-01

117

Isolation of indole alkaloids from Catharanthus roseus by centrifugal partition chromatography in the pH-zone refining mode  

Microsoft Academic Search

Centrifugal partition chromatography (CPC) in the pH-zone refining mode allowed a preparative and efficient isolation of vindoline, vindolinine, catharanthine and vincaleukoblastine from a crude mixture of Catharanthus roseus alkaloids. The separation protocol was tested with a synthetic mixture of vindoline, catharanthine and vincaleukoblastine. The fraction content was analyzed and the results compared with theoretical chromatograms obtained by numerical simulation. The

Jean-Hugues Renault; Jean-Marc Nuzillard; Gaëlle Le Crouérour; Philippe Thépenier; Monique Zèches-Hanrot; Louisette Le Men-Olivier

1999-01-01

118

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

119

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

120

An isopavine alkaloid from Thalictrum minus  

Microsoft Academic Search

A new alkaloid, isothalisopavine, was isolated from Thalictrum minus and shown to be 2,3,8-trimethoxy-7-hydroxyisopavine from spectral evidence. The known thalisopavine, from T. dasycarpum, is 2,3,8-trimethoxy-9-hydroxyisopavine. Isothalisopavine is the first of its class to be substituted unsymmetrically in the two aromatic rings.

Atanas K. Sidjimov; Jeanne N. Tawara; Frank R. Stermitz; Christopher D. Rithner

1998-01-01

121

Hemlock alkaloids from Socrates to poison aloes  

Microsoft Academic Search

Hemlock (Conium maculatum L. Umbelliferae) has long been known as a poisonous plant. Toxicity is due to a group of piperidine alkaloids of which the representative members are coniine and ?-coniceine. The latter is the more toxic and is the first formed biosynthetically. Its levels in relation to coniine vary widely according to environmental conditions and to provenance of the

Tom Reynolds

2005-01-01

122

Monomeric Indole Alkaloids from Ervatamia hainanensis.  

PubMed

Eleven monomeric indole alkaloids have been isolated from the roots of Ervatamia hainanensis. Nine of them are known: coronaridine 1, coronaridine hydroxyindolenine 2, heyneanine 3, vobasine 4, perivine 5, ibogamine 6, geissoschizol 7, 10-hydroxygeissoschizol 8 and 3-oxocoronaridine 9; and two are new: 10-hydroxyheyneanine 10 and 3-(beta-hydroxyethyl)-coronaridine 11. PMID:17402121

Feng, X Z; Kan, C; Potier, P; Kan, S K; Lounasmaa, M

1982-04-01

123

Piperdardine, a piperidine alkaloid from Piper tuberculatum  

Microsoft Academic Search

A new piperidine alkaloid 1-[7-(1,3-benzodioxol-5-yl)-1-oxo-2, 4-heptadienyl]piperidine, piperdardine, was isolated from hexane and chloroform extracts of Piper tuberculatum var. tuberculatum. A combination of 1D and 2D NMR, together with other spectroscopic methods, led to the unambiguous assignments of all protons and carbons of the molecule.

João Xavier De Araujo-Junior; Emidio V. L. Da-Cunha; Maria Célia De O. Chaves; Alexander I. Gray

1997-01-01

124

Ergot alkaloids decrease rumen epithelial blood flow  

Technology Transfer Automated Retrieval System (TEKTRAN)

Two experiments were conducted to determine if ergot alkaloids affect blood flow to the absorptive surface of the rumen of steers. Steers (n=8 total) were pair-fed alfalfa cubes at 1.5× NEM and received ground endophyte-infected tall fescue seed (E+) or endophyte-free tall fescue seed (E-) via rumen...

125

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

126

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

127

Alkaloid metabolism in wounded Catharanthus roseus seedlings  

Microsoft Academic Search

The effect of mechanical wounding on alkaloid metabolism was analyzed in Catharanthus roseus seedlings. Wounding induced an increase in ajmalicine accumulation, whereas catharanthine remained unaffected. A positive dual effect on vindoline was noticed. Short and mid-term effects were detected between 12 and 24 h after mechanical damage was inflicted, and apparently resulted from the accelerated transformation of the tabersonine intermediaries to vindoline.

Felipe Vázquez-Flota; Mildred Carrillo-Pech; Yereni Minero-García; María de Lourdes Miranda-Ham

2004-01-01

128

Analysis of Catharanthus roseus alkaloids by HPLC  

Microsoft Academic Search

Catharanthus roseus is a medicinal plant from which secondary metabolites used in chemotherapy to treat diverse cancers are extracted. The well\\u000a known high value metabolites vincristine and vinblastine are just 2 of 130 alkaloids that can be found in C. roseus. However, only few (?11) of this high number of chemical entities are frequently analyzed and even fewer (?8) are

Steve Hisiger; Mario Jolicoeur

2007-01-01

129

Cremastrine, a pyrrolizidine alkaloid from Cremastra appendiculata.  

PubMed

A new pyrrolizidine alkaloid, cremastrine (1), was isolated from the bulbs of Cremastra appendiculata. Its configuration was determined by spectroscopic and chemical analyses. Compound 1 inhibited the binding of tritium-labeled N-methylscopolamine to the muscarinic M3 receptor with a K(i) value of 126 nM. PMID:15844951

Ikeda, Yoshitaka; Nonaka, Hikaru; Furumai, Tamotsu; Igarashi, Yasuhiro

2005-04-01

130

Two steroidal alkaloids from veratrum viride  

Microsoft Academic Search

A phytochemical study of the roots and rhizomes of Veratrum viride led to the isolation of the two new steroidal alkaloids, rubivirine, identified as 12?-hydroxyisorubijervine, and veramivirine, identified as 12?-hydroxyveramiline. Structural elucidation of the two compounds was aided by 2D-NMR spectral analyses.

Khalid A. El Sayed; James D. McChesney; Ahmed F. Halim; Ahmed M. Zaghloul; Markus Voehler

1995-01-01

131

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

132

An isopavine alkaloid from Thalictrum minus.  

PubMed

A new alkaloid, isothalisopavine, was isolated from Thalictrum minus and shown to be 2,3,8-trimethoxy-7-hydroxyisopavine from spectral evidence. The known thalisopavine, from T. dasycarpum, is 2,3,8-trimethoxy-9-hydroxyisopavine. Isothalisopavine is the first of its class to be substituted unsymmetrically in the two aromatic rings. PMID:9637067

Sidjimov, A K; Tawara, J N; Stermitz, F R; Rithner, C D

1998-05-01

133

Pyrrolizidine alkaloid deters ant predators of Utetheisa ornatrix eggs: effects of alkaloid concentration, oxidation state, and prior exposure of ants to alkaloid-laden prey  

Microsoft Academic Search

To examine the chemical defense of lepidopteran eggs towards ant predators, eggs of the arctiid moth Utetheisa ornatrix were offered to laboratory colonies of the ant Leptothorax longispinosus. The ants rapidly devoured Utetheisa eggs produced by parents reared on an alkaloid-free diet, but left eggs that had been endowed with parental alkaloid largely unmolested. That defense can be attributed directly

James F. Hare; Thomas Eisner

1993-01-01

134

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.

135

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

136

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

137

Discovery of skin alkaloids in a miniaturized eleutherodactylid frog from Cuba  

PubMed Central

Four phylogenetically independent lineages of frogs are currently known to sequester lipid-soluble skin alkaloids for which a dietary source has been demonstrated. We report here a remarkable fifth such instance, in Eleutherodactylus iberia and Eleutherodactylus orientalis, two species of miniaturized frogs of the family Eleutherodactylidae from Cuba. Six pumiliotoxins and two indolizidines were found in E. iberia, one of the smallest frogs in the world and characterized by a contrasting colour pattern for which we hypothesize an aposematic function. Analyses of stomach content indicated a numerical prevalence of mites with an important proportion of oribatids—a group of arthropods known to contain one of the pumiliotoxins detected in E. iberia. This suggests that miniaturization and specialization to small prey may have favoured the acquisition of dietary skin alkaloids in these amphibians. PMID:21047848

Rodríguez, Ariel; Poth, Dennis; Schulz, Stefan; Vences, Miguel

2011-01-01

138

[Studies on the alkaloids of Gynura segetum (Lour.) Merr].  

PubMed

Six alkaloids were isolated from Gynura segetum (Lour.) Merr. Four of them were identified. Alkaloids I and II were identified as known senecionine and seneciphylline, respectively. Alkaloids III and IV were found to be new compounds named seneciphyllinine and (E)-seneciphylline respectively. Their structures were confirmed on the basis of spectral data (UV, IR, MS, 1HNMR, 13CNMR, C-H COSY). PMID:2239333

Yuan, S Q; Gu, G M; Wei, T T

1990-01-01

139

Pyrrolizidine alkaloids in overwintering monarch butterflies ( Danaus plexippus ) from mexico  

Microsoft Academic Search

Summary North American populations of the monarch butterfly,Danaus plexippus, have been found to contain pyrrolizidine alkaloids and their N-oxides. Analytical methods (TLC, GC, and GC\\/MS) have been developed to isolate, quantitate, and structurally elucidate the alkaloids. Examples of at least two classes of pyrrolizidine alkaloids have been identified, the macrocyclic diesters, senecionine, integerrimine, and seneciphylline, and the monoesters, echinatine, intermedine,

R. B. Kelley; J. N. Seiber; A. D. Jones; H. J. Segall; L. P. Brower

1987-01-01

140

Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors  

Microsoft Academic Search

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 cleft palate. A pharmacodynamic comparison of the alkaloids ammodendrine, anabasine, anabaseine, anagyrine, and coniine in SH-SY5Y cells and TE-671 cells was made. These

Benedict T. Green; Stephen T. Lee; Kip E. Panter; Kevin D. Welch; Daniel Cook; James A. Pfister; William R. Kem

2010-01-01

141

Alkaloids from the roots of Senecio macedonicus Griseb.  

PubMed

The new alkaloids 7-,9-diangeloylplatynecine (1) and 8-episarracine N-oxide (2), were isolated and identified from the roots of Senecio macedonicus. Another one, 8-epineosarracine was detected by GC/MS analyses of the crude alkaloid mixture. The cytotoxicity and biological activity of the alkaloids were tested on normal murine spleen lymphocytes and P3U1 mouse myeloma. PMID:12440711

Christov, Veselin; Mikhova, Bozhanka; Alexandrova, Radostina; Dimitrova, Daniela; Nikolova, Elena; Evstatieva, Liuba

2002-01-01

142

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

143

Detrimental effects of Cinchona leaf alkaloids on larvae of the polyphagous insect Spodoptera exigua  

Microsoft Academic Search

YoungCinchona ledgeriana plants contain two types of alkaloid: indole alkaloids in the leaves and quinoline alkaloids in the root. FromCinchona leaves, a crude alkaloid extract was made, containing the cinchophylline type of indole alkaloids and a small amount of 5-methoxytryptamine. The leaf alkaloid extract exerted a strong detrimental effect on the growth of larvae of the polyphagous beet armyworm,Spodoptera exigua

Rob J. Aerts; Andries Stoker; Maarten Beishuizen; Ineke Jaarsma; MIEKE VAN DE HEUVEL; EDDY VAN DER MEIJDEN; Rob Verpoorte

1992-01-01

144

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

145

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

146

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

147

Pyrrolizidine alkaloids in honey and bee pollen  

Microsoft Academic Search

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

A. Dübecke; G. Beckh; C. Lüllmann

2011-01-01

148

New Indole Alkaloids from Amsonia sinensis.  

PubMed

Fourteen indole alkaloids, Delta (14)-isoeburnamine ( 1), amsosinine ( 2), tabersonine, vincadifformine, lochnericine, tetrahydroalstonine, beta-yohimbine, isoeburnamine, minovicinine, picrinine, strictamine, rhazimine, vincanidine, and decarbomethoxytetrahydrosecamine, were isolated from AMSONIA SINENSIS. Delta (14)-isoeburnamine ( 1) and amsosinine ( 2) are new compounds, their structures have been established by spectral and chemical methods. A known sterol glycoside, daucosterol, has also been obtained. The structures of compounds 1 and 2 were finally confirmed by X-ray diffraction of single crystals. PMID:17226203

Liu, H M; Wu, B; Zheng, Q T; Feng, X Z

1991-12-01

149

Tetrahydroprotoberberine and aporphine alkaloids from rollinia leptopetala.  

PubMed

Tetrahydrojatrorrhizine, discretamine, anonaine and roemerine were isolated from the roots of Rollinia leptopetala R. E. Fries. They were identified and characterized by nuclear magnetic resonance spectroscopy ( 1 H and 13 C) with the aid of two-dimensional techniques ( 1 H- 1 H COSY, HETCOR, HMQC and HMBC). With the exception of tetrahydrojatrorrhizine, the presence of these alkaloids in R. leptopetala has not been reported previously. PMID:21214484

Sette, I M; da-Cunha, E V; Barbosa-Filho, J M; da-Silva, M S

2000-01-01

150

Defensive properties of pyrrolizidine alkaloids against microorganisms  

Microsoft Academic Search

The understanding of the selection factors that drive chemical diversification of secondary metabolites of constitutive defence\\u000a systems in plants, such as pyrrolizidine alkaloids (PAs), is still incomplete. Historically, plants always have been confronted\\u000a with microorganisms. Long before herbivores existed on this planet, plants had to cope with microbial pathogens. Therefore,\\u000a plant pathogenic microorganisms may have played an important role in

Lotte JoostenJohannes; Johannes A. van Veen

2011-01-01

151

Synthesis and SAR of vinca alkaloid analogues  

Microsoft Academic Search

Versatile intermediates 12?-iodovinblastine, 12?-iodovincristine and 11?-iodovinorelbine were utilized as substrates for transition metal based chemistry which led to the preparation of novel analogues of the vinca alkaloids. The synthesis of key iodo intermediates, their transformation into final products, and the SAR based upon HeLa and MCF-7 cell toxicity assays is presented. Selected analogues 27 and 36 show promising anticancer activity

Matthew E. Voss; Jeffery M. Ralph; Dejian Xie; David D. Manning; Xinchao Chen; Anthony J. Frank; Andrew J. Leyhane; Lei Liu; Jason M. Stevens; Cheryl Budde; Matthew D. Surman; Thomas Friedrich; Denise Peace; Ian L. Scott; Mark Wolf; Randall Johnson

2009-01-01

152

Isolation of an alkaloid from Cassia occidentalis  

E-print Network

)ect: Biochemistry THE ISOLATION OF AN ALKALOID FROM CASSIA OCCIDENTALIS A Thesis Larry Ellis Puleo Approved as to style and oontent by: hairman o mmit e M ber Hea o partment Member ACKNOWLEDGEMENT 8 The writer wishes to express hie appreciationt To Dr. B... Scheme Page II Toxicity of various fractions of Cassia occidentalis 20 LIST OF FIGURES Figure 1 Mass Speotrum of the Isolated Compound 2 Infrared Speotrum of the Isolated Com- pound Ultraviolet Absorption Speotrum oi the Isolated Compound...

Puleo, Larry Ellis

1966-01-01

153

Pyrrolizidine Alkaloids Crosslink DNA with Actin  

Microsoft Academic Search

Pyrrolizidine alkaloids (PAs) are toxic constituents of hundreds of plant species, some of which people are exposed to in herbal products and traditional remedies. The bioactivity of PAs are related, at least in part, to their ability to form DNA–protein complexes (DPC). Previous studies from our laboratory indicated a possible role for actin in PA-induced DPCs. Nuclei prepared from Madin-Darby

Roger A. Coulombe; Gail L. Drew; Frank R. Stermitz

1999-01-01

154

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 IC?? 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

155

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

156

Solanidane and iminosolanidane alkaloids from Solanum campaniforme.  

PubMed

From the leaves of Solanum campaniforme (Solanaceae), eight solanidane alkaloids were isolated, four of which contain a p-hydroxyphenylethylamine unit. Their structures were established as: 22?,23?-epoxy-solanida-1,4-dien-3-one; 22?,23?-epoxy-10-epi-solanida-1,4,9-trien-3-one; 22?,23?-epoxy-solanida-4-en-3-one; 22?,23?-epoxy-solanida-4-en-3-one; (E)-N-[8'(4-hydroxyphenyl)ethyl]-22?,23?-epoxy-solanida-1,4,9-trien-3-imine; (E)-N-[8'(4-hydroxyphenyl)ethyl]-22?,23?-epoxy-solanida-1,4-dien-3-imine; (Z)-N-[8'(4-hydroxyphenyl)ethyl]-22?,23?-epoxy-solanida-1,4,9-trien-3-imine and (Z)-N-[8'(4-hydroxyphenyl)ethyl]-22?,23?-epoxy-solanida-1,4-dien-3-imine. All structures were determined using spectroscopic techniques, such as 1D and 2D NMR, and HRESIMS. The cytotoxicity and the antiophidic activities of the alkaloids were evaluated. The alkaloids did not show any cytotoxicity, but inhibited the main toxic actions of Bothrops pauloensis venom. PMID:24075572

Torres, Maria Conceição M; Jorge, Roberta Jeane B; Ximenes, Rafael M; Alves, Natacha Teresa Q; Santos, João Victor de A; Marinho, Aline D; Monteiro, Helena S A; Toyama, Marcos H; Braz-Filho, Raimundo; Silveira, Edilberto R; Pessoa, Otília Deusdênia L

2013-12-01

157

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

158

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.

159

Expression of terpenoid indole alkaloid biosynthetic pathway genes corresponds to accumulation of related alkaloids in Catharanthus roseus (L.) G. Don  

Microsoft Academic Search

Madagascar periwinkle, Catharanthus roseus (L.) G. Don, a medicinally important plant, produces anticancer dimeric alkaloids, vinblastine and vincristine, in the leaves and accumulates antihypertensive alkaloids, ajmalicine and serpentine, in the roots. This plant grows wild in distant tropical and sub-tropical geographical locations with different agro-climates and shows wide variations in morphological and alkaloid yield-related traits. In order to understand the

Ajaswrata Dutta; Jyoti Batra; Sashi Pandey-Rai; Digvijay Singh; Sushil Kumar; Jayanti Sen

2005-01-01

160

Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia cell cultures  

Microsoft Academic Search

Quaternary benzophenanthridine alkaloids (sanguinarine, chelerythrine, chelirubine, chelilutine and macarpine) are specifically induced by cell wall components of Penicillium and Saccharomyces in a colorless strain of Eschscholtzia californica cell suspension cultures. Classical elicitors such as the Phytophthora megasperma elicitor are inactive. The alkaloid synthesis is, however, strongly induced by certain polypeptide antibiotics. Out of 190 tested plant species the yeast elicitor

H.-M. Schumacher; H. Gundlach; F. Fiedler; M. H. Zenk

1987-01-01

161

Tertiary indole alkaloids from leaves of Tabernaemontana dichotoma.  

PubMed

Seven indole alkaloids were isolated and identified from the leaves of Tabernaemontana dichotoma Roxb. The major alkaloids were: perivine, 19-epi-voacristine, 12-methoxy-voaphylline and vobasine. (-)apparicine, 19-epi-iboxygaine and isomethuenine occurred in minor amounts. PMID:17404903

Perera, P; Samuelsson, G; van Beek, T A; Verpoorte, R

1983-03-01

162

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

163

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...

164

Leptopyrine, new alkaloid from Leptopyrum fumarioides L. (Ranunculaceae).  

PubMed

A new type of isoquinoline alkaloid leptopyrine was isolated from the aerial parts of Leptopyrum fumarioides L. (Ranunculaceae) of Mongolian origin. The known alkaloids protopine and thalifoline were isolated for the first time from this the species. All structures were established by physical and spectral analyses. PMID:25529023

Doncheva, Tsvetelina; Solongo, Amgalan; Kostova, Nadezhda; Gerelt-Od, Yadamsuren; Selenge, Dangaa; Philipov, Stefan

2015-05-01

165

Calystegines as a new group of tropane alkaloids in Solanaceae  

Microsoft Academic Search

Calystegines are a new group of polyhydroxy alkaloids with a nortropane skeleton. They were detected in Atropa belladonna root cultures by chromatographic methods (TLC, GC) and identified by NMR and mass spectroscopy. Their occurrence was examined in several species of the Solanaceae. The biosynthesis of these compounds is suggested to proceed via the tropane alkaloid pathway, the first metabolite being

Birgit Dräger; Christoph Funck; Almut Höhler; Gabriele Mrachatz; Adolf Nahrstedt; Andreas Portsteffen; Angela Schaal; Rainer Schmidt

1994-01-01

166

Calystegins, a novel class of alkaloid glycosidase inhibitors.  

PubMed

The alkaloid extract from roots of naturally growing Convolvulus arvensis, purified by ion-exchange chromatography, showed significant inhibitory activity toward beta-glucosidase and alpha-galactosidase. The demonstrated occurrence of polyhydroxy-nortropane alkaloids, the calystegins, in C. arvensis and their structural similarity to known polyhydroxy alkaloid glycosidase inhibitors, suggested that these might be responsible for the observed activity. Pure calystegins, isolated from transformed root cultures of the related plant species Calystegia sepium, were tested for glycosidase inhibitory activity. The purity of the alkaloids was established by gas chromatography and their identity confirmed by their mass spectrometric fragmentation patterns. The trihydroxy alkaloid, calystegin A3, was a moderately good inhibitor of beta-glucosidase (Ki = 4.3 x 10(-5) M) and a weak inhibitor of alpha-galactosidase (Ki = 1.9 x 10(-4) M). An increased level of hydroxylation, as in the tetrahydroxy calystegins B, consisting of 27% calystegin B1 and 73% calystegin B2, resulted in greatly enhanced inhibitory activity. The calystegins B were potent inhibitors of beta-glucosidase (Ki = 3 x 10(-6) M) and alpha-galactosidase (Ki = 7 x 10(-6) M). These levels of activity are comparable with those of the polyhydroxy indolizidine alkaloids castanospermine and swainsonine toward alpha-glucosidase and alpha-mannosidase, respectively, and of the polyhydroxy pyrrolizidine alkaloid australine toward alpha-glucosidase. The calystegins therefore compose a new structural class of polyhydroxy alkaloids, the nortropanes, possessing potent glycosidase inhibitory properties. PMID:8323301

Molyneux, R J; Pan, Y T; Goldmann, A; Tepfer, D A; Elbein, A D

1993-07-01

167

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

168

Engineering Plant Alkaloid Biosynthetic Pathways: Progress and Prospects  

Microsoft Academic Search

With the successful application of molecular genetic methods to the plant alkaloid field, we now have sophisticated tools at our disposal to study regulation of enzymatic biosynthesis, as well as determining the cellular and subcellular localization of these enzymes. The availability of ever?increasing numbers of recombinant enzymes has enabled thorough analyses of selected alkaloid biosynthetic enzymes at the biochemical and

Toni M. Kutchan; Susanne Frick; Marion Weid

2008-01-01

169

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

170

Increasing the content of leaf and root alkaloids of high alkaloid content mutants of periwinkle through nitrogen fertilization  

Microsoft Academic Search

In industrial plants such as medicinal plants, the content of the economically important metabolite is more important than the yield of the plant part containing the metabolite, as it determines the cost of extraction of the metabolite. Two high alkaloid content mutants of periwinkle (Catharanthus roseus, a medicinal plant yielding anti-cancer and anti-hypertension alkaloids) were developed through induced mutagenesis. Since

Y. Sreevalli; R. N. Kulkarni; K. Baskaran; R. S. Chandrashekara

2004-01-01

171

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.

172

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

2001-01-01

173

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

174

Piperine, the main alkaloid of Thai black pepper, protects against neurodegeneration and cognitive impairment in animal model of cognitive deficit like condition of Alzheimer’s disease  

Microsoft Academic Search

Recently, numerous medicinal plants possessing profound central nervous system effects and antioxidant activity have received much attention as food supplement to improve cognitive function against cognitive deficit condition including in Alzheimer’s disease condition. Based on this information, the effect of piperine, a main active alkaloid in fruit of Piper nigrum, on memory performance and neurodegeneration in animal model of Alzheimer’s

Pennapa Chonpathompikunlert; Jintanaporn Wattanathorn; Supaporn Muchimapura

2010-01-01

175

[Cytotoxic alkaloids from stems of Nelumbo nucifera].  

PubMed

Chemical investigation was carried out to study the alkaloids from stems of Nelumbo nucifera and their cytotoxic activities. The constituents were separated by column chromatography, and their structures were elucidated by spectroscopic data analyses. The isolated compounds were evaluated for their cytotoxic activities by MTr method. Fifteen compounds were isolated from the total alkaloids extract and identified as asimilobine (1), isococlaurine (2), N-acetylnorarmepavine (3), crykonisine (4), velucryptine (5), pycnarrhine (6), liriodenine (7), nuciferine (8), nornuciferine (9), armepavine (10), N-methylasimilobine (11), coclaurine (12), N-norarmepavine (13), N-methylcoclaurine (14) and lysicamine (15). Compounds 1-7 and 12-15 were isolated from stems of this plant for the first time, and compounds 2-6 were firstly isolated from the family Nelumbonaceae. Compounds 7-10, 13 and 14 showed significant cytotoxic activities against HL-60 carcinoma cell line with inhibitory ratios of 51.36%, 59.09%, 52.51%, 53.93%, 51.43%, and 64.31% at concentration of 1 x 10(-5) mol x L(-1), respectively. PMID:24791498

Duan, Xu-Hong; Pei, Lin; Jiang, Jian-Qin

2013-12-01

176

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

177

A new alkaloid from Salsola collina.  

PubMed

Salsola collina is widely distributed in droughty and semi-droughty area, which is used as a kind of folk remedy in traditional Chinese medicine for treatment of hypertension. The study is on the chemical constituents of this herb from its aerial parts to obtain its active constituents. Dried and crushed aerial parts of this herb were extracted three times with 95% EtOH at reflux. The ethanol extracts were combined and concentrated under reduced pressure at 70 degrees C to yield residue, which was suspended in water and successively partitioned with light petroleum, chloroform and n-butanol. The chloroform and n-butanol fractions were treated by various chromatographic techniques, such as silica gel, C18 reversed-phase silica gel and macroporous resin column chromatography. Compounds were elucidated by their physicochemical properties and spectroscopic analysis. In the course of our study on searching biological active components from this herb, a new alkaloid together with three known alkaloids were isolated and identified as N-transferuloyl-3-methyldopamine (1), 3-[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]-N-[2-(4-hydroxyl-3-methoxyphenyl) ethyl]-2-propenamide (2), salsoline A (3), salsoline B (4). Compound 4 is a new compound and named as salsoline B, while compound 2 was obtained in Salsola collina for the first time. PMID:17702398

Xiang, Yu; Li, You-Bin; Zhang, Jian; Li, Ping; Yao, Yuan-Zhang

2007-06-01

178

Neutral heroin impurities from tetrahydrobenzylisoquinoline alkaloids.  

PubMed

Laudanosine, reticuline, codamine, and laudanine are members of the tetrahydrobenzylisoquinoline family of natural products. These alkaloids are present in the opium poppy, Papaver somniferum, and are subsequently found as impurities in clandestinely processed morphine. Morphine is then synthesized to heroin using hot acetic anhydride. During the course of this study, it was determined that these four tetrahydrobenzylisoquinolines undergo degradation to a series of 18 neutral impurities when subjected to hot acetic anhydride. Based on the degradation pathway, these new impurities were categorized into two sets of impurities called the C1-acetates compounds and the stilbene compounds. Synthesis, isolation, and structural elucidation information is provided for the tetrahydrobenzylisoquinoline alkaloids, and the new neutral impurities have been studied. Several hundred authentic heroin samples were analyzed using an established heroin signature program method. This methodology features the detection of trace neutral impurities present in heroin samples. It was determined that all 18 new impurities were detected in various quantities in four different types of heroin samples. Analytical results featuring these new impurities are reported for South American-, Southwest Asian-, Mexican-, and Southeast Asian-type heroin samples. These new impurities, coupled with other established forensic markers, enhance the ability to classify illicit heroin samples. PMID:16566764

Toske, Steven G; Cooper, Samuel D; Morello, David R; Hays, Patrick A; Casale, John F; Casale, Ellen

2006-03-01

179

Alkaloids in ergot found on different Gramineae in The Netherlands.  

PubMed

The alkaloid content and the composition of the alkaloid complex of thirteen samples of ergot sclerotia from different gramineous host species collected in The Netherlands were investigated. Two samples collected in France were also examined. Ergot of Glyceria fluitans (L.) R.Br. did not contain alkaloids. The total alkaloid content of ergot found on the other wild grasses was more than 0.2%. The ratio between the contents of water soluble and water insoluble alkaloids of the investigated ergot sclerotia varies between 1:10 and 1:20. The composition of the alkaloid complex in the sclerotia was studied by quantitative thin-layer chromatography. The sclerotia could be grouped into three main categories: --sclerotia of Lolium perenne L., Festuca arundinacea Schreb. and Arrhenatherum elatius (L.) P.B. ex J. et C. Presl, containing predominantly ergocornine, alpha- and beta-ergokryptine and ergosine; --sclerotia of Dactylis glomerata L., Phalaris arundinacea L., Alopecurus geniculatus L. and Holcus mollis L., containing predominantly ergosine, ergocristine and ergotamine; --sclerotia of Molinia caerulea (L.) Moench, containing predominantly ergocristine, ergosine and ergometrine. A great similarity was found between the composition of the alkaloid complex in ergot of Lolium perenne L. from different locations and also in ergot of Molinia caerulea (L.) Moench from different locations. This similarity was less in ergot of Dactylis glomerata L. collected from different locations. PMID:6646990

Reicher, A; Elema, E T; Zwaving, J H; Malingré, T M

1983-10-21

180

[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

181

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

182

Two new N-oxide alkaloids from Stemona cochinchinensis.  

PubMed

Two new N-oxide alkaloids with pyrrolo[1,2-?]azepine skeleton, namely isoneostemocochinine-N-oxide (1) and neostemocochinine-N-oxide (2), as well as three known alkaloids with pyrido[1,2-?]azepine skeletons, were isolated and identified from the roots of Stemona cochinchinensis (Stemonaceae). The structures of these compounds were elucidated by 1D- and 2D-NMR spectra and other spectroscopic studies. Additionally, the 1H- and 13C-NMR characteristic of N-oxide Stemona alkaloids was summarized. Stemokerrin showed potent anti-tussive activity on citric acid-induced guinea pig model. PMID:25479189

Lin, Ligen; Bao, Han; Wang, Anqi; Tang, Chunping; Dien, Pham-Huu; Ye, Yang

2014-01-01

183

Cyclobutane-Containing Alkaloids: Origin, Synthesis, and Biological Activities  

PubMed Central

Present review describes research on novel natural cyclobutane-containing alkaloids isolated from terrestrial and marine species. More than 60 biological active compounds have been confirmed to have antimicrobial, antibacterial, antitumor, and other activities. The structures, synthesis, origins, and biological activities of a selection of cyclobutane-containing alkaloids are reviewed. With the computer program PASS some additional biological activities are also predicted, which point toward new possible applications of these compounds. This review emphasizes the role of cyclobutane-containing alkaloids as an important source of leads for drug discovery. PMID:19696873

Sergeiko, Anastasia; Poroikov, Vladimir V; Hanuš, Lumir O; Dembitsky, Valery M

2008-01-01

184

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. PMID:25580241

2013-01-01

185

Anticancer Alkaloid Lamellarins Inhibit Protein Kinases  

PubMed Central

Lamellarins, a family of hexacyclic pyrrole alkaloids originally isolated from marine invertebrates, display promising anti-tumor activity. They induce apoptotic cell death through multi-target mechanisms, including inhibition of topoisomerase I, interaction with DNA and direct effects on mitochondria. We here report that lamellarins inhibit several protein kinases relevant to cancer such as cyclin-dependent kinases, dual-specificity tyrosine phosphorylation activated kinase 1A, casein kinase 1, glycogen synthase kinase-3 and PIM-1. A good correlation is observed between the effects of lamellarins on protein kinases and their action on cell death, suggesting that inhibition of specific kinases may contribute to the cytotoxicity of lamellarins. Structure/activity relationship suggests several paths for the optimization of lamellarins as kinase inhibitors. PMID:19172192

Baunbæk, Dianne; Trinkler, Nolwenn; Ferandin, Yoan; Lozach, Olivier; Ploypradith, Poonsakdi; Rucirawat, Somsak; Ishibashi, Fumito; Iwao, Masatomo; Meijer, Laurent

2008-01-01

186

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

187

Synthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids  

PubMed Central

The epipolythiodiketopiperazine (ETP) alkaloids are a highly complex class of natural products with potent anticancer activity. Herein, we report the application of a flexible and scalable synthesis, allowing the construction of dozens of ETP derivatives. The evaluation of these compounds against cancer cell lines in culture allows for the first expansive structure–activity relationship (SAR) to be defined for monomeric and dimeric ETP-containing natural products and their synthetic cognates. Many ETP derivatives demonstrate potent anticancer activity across a broad range of cancer cell lines, and kill cancer cellsviainduction of apoptosis. Several traits thatbode well for the translational potential of the ETP class of natural products includeconcise and efficient synthetic access, potent induction of apoptotic cell death, activity against a wide range of cancer types, and a broad tolerance for modifications at multiple sitesthat should facilitate small-molecule drug development, mechanistic studies, and evaluation in vivo. PMID:23914293

Boyer, Nicolas; Morrison, Karen C.; Kim, Justin; Hergenrother, Paul J.; Movassaghi, Mohammad

2013-01-01

188

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

189

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

190

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

191

Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course  

PubMed Central

We recount several unexpected results observed in the course of our work toward the synthesis of welwitindolinone alkaloids. The surprising results provide an opportunity to refine one’s understanding of the interplay between chemical structure and reactivity. PMID:22962500

Bhat, Vikram; MacKay, James A.; Rawal, Viresh H.

2012-01-01

192

Aza-Tryptamine Substrates in Monoterpene Indole Alkaloid Biosynthesis  

E-print Network

Biosynthetic pathways can be hijacked to yield novel compounds by introduction of novel starting materials. Here we have altered tryptamine, which serves as the starting substrate for a variety of alkaloid biosynthetic ...

Lee, Hyang-Yeol

193

Muscarine, imidazole, oxazole, thiazole, Amaryllidaceae and Sceletium alkaloids.  

PubMed

A review with 136 references covers the literature from July 2000 to June 2001 on the isolation, bioactivities, and synthetic highlights of complex natural products including muscarine, imidazole, oxazole, thiazole, Amaryllidaceae and Sceletium alkaloids. PMID:12195812

Jin, Zhong; Li, Zaiguo; Huang, Runqiu

2002-08-01

194

[Monomeric indole alkaloids from the aerial parts of Catharanthus roseus].  

PubMed

Catharanthus roseus (L.) G. Don is a plant of the Catharanthus genus of Apocynaceae which has been reported to have therapeutic effects of detoxication and anticancer. In order to further study the alkaloid constituents of C. roseus, the aerial parts of the plant were extracted with 95% EtOH, and then treated with 2% H2SO4 and NH3H2O to obtain total alkaloids. The total alkaloids were separated and purified by column chromatography over silica gel and prepared by high performance liquid chromatography (HPLC). Their structures were elucidated on the basis of physicochemical properties and spectral data. A new alkaloid together with five known compounds were isolated and identified as vindolinine B (1), lochnericine (2), horhammericine (3), vindorosine (4), vindoline (5), and coronaridine (6). Compound 1 is a new compound and named as vindolinine B. PMID:21355212

Zhong, Xiang-Zhang; Wang, Guo-Cai; Wang, Ying; Zhang, Xiao-Qi; Ye, Wen-Cai

2010-04-01

195

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

196

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

197

Total synthesis of the bridged indole alkaloid apparicine.  

PubMed

An indole-templated ring-closing metathesis or a 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine. From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents. PMID:19824689

Bennasar, M-Lluïsa; Zulaica, Ester; Solé, Daniel; Roca, Tomàs; García-Díaz, Davinia; Alonso, Sandra

2009-11-01

198

Lannotinidines H-J, new Lycopodium alkaloids from Lycopodium annotinum.  

PubMed

Three new Lycopodium alkaloids, lannotinidines H-J (1-3), were isolated from the club moss Lycopodium annotinum. The structures and relative stereochemistry of 1-3 were elucidated on the basis of spectroscopic data and the absolute stereochemistry of 2 was assigned by chemical correlation. Lannotinidine H (1) is the first Lycopodium alkaloid possessing a lycopodane skeleton with an additional C(3) unit. PMID:19652418

Ishiuchi, Kan'ichiro; Kodama, Shihomi; Kubota, Takaaki; Hayashi, Shigeki; Shibata, Toshiro; Kobayashi, Jun'ichi

2009-08-01

199

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

200

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

201

The isolation and identification of three alkaloids of Acacia berlandieri  

E-print Network

of the Literature Experimental Extraction Procedure Chromatographic Techniques Paper chromatography Thin layer chromatography Gas-liquid chromatography Chromogenic reagents Reference samples 8 lo 10 ll 12 Resu1ts and Discussion Summary References...) and further investigation revealed the presence of other alkaloids (4). This study was undertaken to elucidate the chemical struc- ture' of these unidentified alkaloids. REVIEW OF THE LITERATURE Acacia berlandieri (gua]illo) is a small tres or shrub 1-4. 5...

Adams, Herman Ray

1965-01-01

202

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

203

Piperidine alkaloid content of Picea pungens (Colorado blue spruce)  

Microsoft Academic Search

The content and pattern of piperidine alkaloid accumulation in Picea pungens, the Colorado blue spruce, was studied as a function of growth stage and plant part. Qualitative and quantitative differences were encountered between early seedlings, mature trees, needles, stems and other plant parts. A new natural piperidine imine alkaloid, 2-methyl-6-propyl-1,6-piperideine, was found and postulated to be an intermediate leading to

Fred G. Todd; Frank R. Stermitz; Andrei V. Blokhin

1995-01-01

204

Evaluation of Aconitum diterpenoid alkaloids as antiproliferative agents.  

PubMed

Little information has been reported on the antitumor effects of the diterpenoid alkaloid constituents of Aconitum plants, used in the herbal drug 'bushi'. This study was aimed at determining the antitumor activities of Aconitum C19-and C20-diterpenoid alkaloids and synthetic derivatives against lung (A549), prostate (DU145), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) cancer cell lines. Newly synthesized C20-diterpenoid alkaloid derivatives showed substantial suppressive effects against all human tumor cell lines tested. In contrast, natural and derivatized C19-diterpenoid alkaloids showed only a slight or no effect. Most of the active compounds were hetisine-type C20-diterpenoid alkaloids, specifically kobusine and pseudokobusine analogs with two different substitution patterns, C-11 and C-11,15. Notably, several C20-diterpenoid alkaloids were more potent against multidrug-resistant KB subline KB-VIN cells. Pseudokobusine 11-3'-trifluoromethylbenzoate (94) is a possible promising new lead meriting additional evaluation against multidrug-resistant tumors. PMID:25770782

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

2015-04-01

205

Rapid determination of Papaver somniferum alkaloids in process streams using monolithic column high-performance liquid chromatography with chemiluminescence detection.  

PubMed

We have combined high-performance liquid chromatography (HPLC) separations using a monolithic column with acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection in a rapid and highly sensitive method to monitor the process of extracting opiate alkaloids from Papaver somniferum. Due to the high flow rates allowed with the monolithic column and the inherent selectivity of the chemiluminescence reactions, the four predominant alkaloids--morphine, codeine, oripavine and thebaine--were determined in less than 2 min. The results obtained with numerous process samples compared favourable with those of the standard HPLC methodology. Limits of detection were 1x10(-10) M, 5x10(-10) M, 5x10(-10) M and 1x10(-9) M, for morphine, codeine, oripavine and thebaine, respectively. PMID:17658308

Costin, Jason W; Lewis, Simon W; Purcell, Stuart D; Waddell, Lucy R; Francis, Paul S; Barnett, Neil W

2007-07-30

206

Alkaloids and athlete immune function: caffeine, theophylline, gingerol, ephedrine, and their congeners.  

PubMed

Plant alkaloids are found in foods, beverages, and supplements consumed by athletes for daily nutrition, performance enhancement, and immune function improvement. This paper examined possible immunomodulatory roles of alkaloids in exercise contexts, with a focus on human studies. Four representative groups were scrutinized: (a) caffeine (guaranine, mateine); (b) theophylline and its isomers, theobromine and paraxanthine; (c) ginger alkaloids including gingerols and shogaol; and (d) ephedra alkaloids such as ephedrine and pseudoephedrine. Emerging or prospective alkaloid sources (Goji berry, Noni berry, and bloodroot) were also considered. Human in vitro and in vivo studies on alkaloids and immune function were often conflicting. Caffeine may be immunomodulatory in vivo depending on subject characteristics, exercise characteristics, and immune parameters measured. Caffeine may exhibit antioxidant capacities. Ginger may exert in vivo anti-inflammatory effects in certain populations, but it is unclear whether these effects are due to alkaloids or other biochemicals. Evidence for an immunomodulatory role of alkaloids in energy drinks, cocoa, or ephedra products in vivo is weak to nonexistent. For alkaloid sources derived from plants, variability in the reviewed studies may be due to the presence of unrecognized alkaloids or non-alkaloid compounds (which may themselves be immunomodulatory), and pre-experimental factors such as agricultural or manufacturing differences. Athletes should not look to alkaloids or alkaloid-rich sources as a means of improving immune function given their inconsistent activities, safety concerns, and lack of commercial regulation. PMID:24974722

Senchina, David S; Hallam, Justus E; Kohut, Marian L; Nguyen, Norah A; Perera, M Ann d N

2014-01-01

207

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

208

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

PubMed Central

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

209

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

210

Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax  

Technology Transfer Automated Retrieval System (TEKTRAN)

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 wa...

211

Bovine lateral saphenous veins exposed to ergopeptine alkaloids do not relax  

Technology Transfer Automated Retrieval System (TEKTRAN)

The ergot alkaloid, ergovaline has demonstrated a persistent binding and sustained contractile response in several vascular models. It was hypothesized that different alkaloids isolated from tall fescue (Lolium arundinaceum) will contribute to this response differently. The objective was to compare ...

212

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

213

[Bromo- and iodo-containing alkaloids from marine microorganisms and sponges].  

PubMed

The taxonomic distribution, structure, and biological activity of halogenated alkaloids isolated from marine microorganisms and sponges are reviewed. The structures of nearly 140 natural bromo- and iodo-containing alkaloids are shown. PMID:12077845

Dembitsky, V M

2002-01-01

214

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...

215

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

216

New phlegmarane-type, cernuane-type, and quinolizidine alkaloids from two species of Lycopodium  

Microsoft Academic Search

Two new phlegmarane-type alkaloids, cermizines A (1) and B (2), three new quinolizidine alkaloids, cermizine C (3) and senepodines G (4) and H (5), and a new C16N2 type alkaloid consisting of a quinolizidine and a piperidine ring, cermizine D (6), as well as two new cernuane-type alkaloids, cernuine N-oxide (7) and lycocernuine N-oxide (8), have been isolated together with

Hiroshi Morita; Yusuke Hirasawa; Takakazu Shinzato; Jun'ichi Kobayashi

2004-01-01

217

Pyrrolizidine alkaloids from Symphytum officinale L. and their percutaneous absorption in rats  

Microsoft Academic Search

Summary An analysis of a commercial sample of Symphyti radix originating from Poland with a total alkaloid content of 0.07% revealed the presence of 7 pyrrolizidine alkaloid-N-oxides: 7-acetyl intermedine, 7-acetyl lycopsamine as the main constituents and lycopsamine, intermedine, symphytine and traces of 2 further not yet identified alkaloids. The percutaneous absorption of these alkaloids was investigated in rats, using a

J. Brauchli; J. Ltithy; U. Zweifel; Ch. Schlatter

1982-01-01

218

Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars.  

PubMed

In the present study morphinan, tetrahydrobenzylisoquinoline, benzo[c]phenanthridine, and phthalideisoquinoline alkaloids were determined qualitatively and quantitatively by HPLC and LC-MS analysis in tissues of the Tasmanian Papaver somniferum L. elite cultivar C048-6-14-64. The data were compared with the results from the low-morphine cultivar "Marianne". In the elite cultivar, 91.2% of the latex alkaloids consist of the three pharmaceutically most valuable alkaloids: morphine, codeine, and thebaine. In the root system, the major alkaloids are sanguinarine/10-hydroxysanguinarine and dihydrosanguinarine/10-hydroxydihydrosanguinarine. In the stems and leaves of C048-6-14-64, the same alkaloids were measured as in the latex. In the stems, a gradient in relative total alkaloid content from the top downward toward the roots was observed. The concentration of morphine was decreasing toward the roots, whereas an increasing gradient from the upper to the lower stem parts was detected for codeine. The relative total alkaloid concentration in leaves remained constant; no gradient was observed. The cultivar "Marianne" displayed a shifted pattern of alkaloid accumulation and reduced levels of total alkaloid. In the condiment cultivar, 80.5% of the alkaloids of the latex consisted of the two phthalideisoquinoline alkaloids narcotoline and noscapine. Only 18.8% of the relative total alkaloid content were morphinan alkaloids. In contrast to the narcotic cultivar, in which the benzo[c]phenanthridines in roots dominated over the morphinan and tetrahydrobenzylisoquinoline alkaloids, the concentration of benzo[c]phenanthridines in "Marianne" was similar to that of morphinan and tetrahydrobenzylisoquinoline alkaloids. These data suggest a differential alkaloid regulation in each cultivar of P. somniferum. PMID:15921406

Frick, Susanne; Kramell, Robert; Schmidt, Jürgen; Fist, Anthony J; Kutchan, Toni M

2005-05-01

219

Identification and quantitation of opium alkaloids in somatic embryos of Papaver somniferum L.  

E-print Network

of the morphinane alkaloids: morphine, codeine, and thebaine 2. Alkaloid extraction protocol and modifications Chromatogram of opium alkaloid standards using standard C-18 packing 17 Chromatogram of opium alkaloid standards using Nova C-18 packing 17... Chromatogram of dried opium using standard C-18 packing 19 Chromatogram of dried opium using Nova C-18 packing 19 Separation of P. somniferum latex using standard C-18 packing 21 Separation of P. somniferum latex using Nova C-18 packing 21 Relative...

Galewsky, Samuel

1985-01-01

220

Transfer of pyrrolizidine and quinolizidine alkaloids to Castilleja (Scrophulariaceae) hemiparasites from composite and legume host plants  

Microsoft Academic Search

Castilleja (Scrophulariaceae) species of the western United States contain pyrrolizidine and quinolizidine alkaloids. TheCastilleja obtain the alkaloids by root parasitism on host plants, withSenecio atratus andS. triangularis (Asteraceae) furnishing the pyrrolizidines, and quinolizidines being obtained fromLupinus species andThermopsis montana (Leguminosae). Individual plants within a givenCastilleja species population may be devoid of alkaloids while others have high alkaloid content. No populations

Frank R. Stermitz; Guy H. Harris

1987-01-01

221

Antiplatelet aggregation activity of diterpene alkaloids from Spiraea japonica.  

PubMed

Six diterpene alkaloids with an atisine-type C(20)-skeleton isolated from the Chinese herbal medicines Spiraea japonica var. acuta and S. japonica var. ovalifolia, as well as eight derivatives of spiramine C and spiradine F were evaluated for the ability to inhibit aggregation of rabbit platelets induced by arachidonic acid, ADP, and platelet-activating factor (PAF) in vitro. The results showed that 12 of the 14 atisine-type diterpene alkaloids significantly inhibited PAF-induced platelet aggregation in a concentration-dependent manner, but had no effect on ADP- or arachidonic acid-induced aggregation, exhibiting a selective inhibition. It is the first report that C(20)-diterpene alkaloids inhibit PAF-induced platelet aggregation. However, spiramine C1 concentration-dependently inhibited platelet aggregation induced by PAF, ADP and arachidonic acid with IC(50) values of 30.5+/-2.7, 56.8+/-8.4 and 29.9+/-9.9 microM, respectively, suggesting a non-selective antiplatelet aggregation action. The inhibitory effect of spiramine C1 on arachidonic acid was as potent as that of aspirin. Primary studies of the structure-activity relationships for inhibition of PAF-induced aggregation showed that the oxygen substitution at the C-15 position and the presence of an oxazolidine ring in spiramine alkaloids were essential to their antiplatelet aggregation effects. These results suggest that the atisine-type alkaloids isolated from S. japonica are a class of novel antiplatelet aggregation agents. PMID:12163102

Li, Ling; Shen, Yue-Mao; Yang, Xiao-Sheng; Zuo, Guo-Ying; Shen, Zhi-Qiang; Chen, Zhi-He; Hao, Xiao-Jiang

2002-08-01

222

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

223

Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors.  

PubMed

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 cleft palate. A pharmacodynamic comparison of the alkaloids ammodendrine, anabasine, anabaseine, anagyrine, and coniine in SH-SY5Y cells and TE-671 cells was made. These alkaloids and their enantiomers were more effective in depolarizing TE-671 cells which express the human fetal-muscle type nicotinic acetylcholine receptor (nAChR) relative to SH-SY5Y cells which predominately express autonomic nAChRs. The rank order of potency in TE-671 cells was: anabaseine>(+)-anabasine>(-)-anabasine > (+/-)-anabasine>anagyrine>(-)-coniine > (+/-)-coniine>(+)-coniine>(+/-)-ammodendrine>(+)-ammodendrine. The rank order potency in SH-SY5Y cells was: anabaseine>(+)-anabasine>(-)-coniine>(+)-coniine>(+)-ammodendrine>anagyrine>(-)-anabasine>(+/-)-coniine>(+/-)-anabasine>(-)-ammodendrine. The actions of these alkaloids at nAChRs in both cell lines could be distinguished by their maximum effects in depolarizing cell membrane potential. The teratogenic action of these compounds may be related to their ability to activate and subsequently desensitize nAChRs. PMID:20116429

Green, Benedict T; Lee, Stephen T; Panter, Kip E; Welch, Kevin D; Cook, Daniel; Pfister, James A; Kem, William R

2010-01-01

224

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

225

Ornithine decarboxylase, polyamines, and pyrrolizidine alkaloids in senecio and crotalaria.  

PubMed

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, H; Birecki, M; Cohen, E J; Bitonti, A J; McCann, P P

1988-01-01

226

Pronuciferine N-oxide, a proaporphine N-oxide alkaloid from Berberis coletioides.  

PubMed

Pronuciferine N-oxide (1), a proaporphine N-methyl-N-oxide alkaloid, along with the parent alkaloid pronuciferine (2) were isolated from Berberis coletioides. The structure of the new compound was determined by spectroscopic evidence. Compound 1 is the first naturally occurring proaporphinoid alkaloid with an N-oxide functionality. PMID:19469512

Fajardo, Víctor; Araya, Marisel; Cuadra, Pedro; Oyarzun, Alejandra; Gallardo, Amalia; Cueto, Mercedes; Diaz-Marrero, Ana R; Darias, José; Villarroel, Luís; Alvarez, Celina; Mora-Pérez, Yolanda; Joseph-Nathan, Pedro

2009-07-01

227

Serratezomines D and E, new Lycopodium alkaloids from Lycopodium serratum var. serratum  

Microsoft Academic Search

Two new Lycopodium alkaloids, serratezomines D (1) and E (2), were isolated from the club moss Lycopodium serratum var. serratum. Serratezomine D (1) is a new lucidine-type alkaloid, while serratezomine E (2) is a new phlegmarane-type alkaloid. The structures and relative stereochemistry of 1 and 2 were elucidated on the basis of spectroscopic data. Serratezomine D (1) exhibited an inhibitory

Takaaki Kubota; Hiroko Yahata; Sunao Yamamoto; Shigeki Hayashi; Toshiro Shibata; Jun’ichi Kobayashi

2009-01-01

228

Genetic diversity and alkaloid production in Catharanthus roseus, C. trichophyllus and their hybrids  

Microsoft Academic Search

Inter and intraspecific variation was analyzed in two Catharanthus species with regard to isozyme polymorphism and indole alkaloid content in roots and leaves. No significant differences in alkaloid production were observed in three groups of C. roseus plants individualized for their flower color. Conversely, comparisons between C. trichophyllus and C. roseus, showed large differences of alkaloid profiles in both roots

M. Sevestre-Rigouzzo; C. Nef-Campa; A. Ghesquière; H. Chrestin

1992-01-01

229

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

230

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

231

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

232

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

233

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.

234

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

235

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.

236

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

237

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

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

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

240

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

241

Capillary electrophoretic studies of acid–base properties of sanguinarine and chelerythrine alkaloids  

Microsoft Academic Search

Capillary zone electrophoresis with UV detection was used for determination of dissociation constants of alkaloids sanguinarine and chelerythrine. Despite the limited solubility of the uncharged forms of the alkaloids resulting in insufficient analytical signal at higher pH the reliable dissociation constants were obtained when acidified samples containing low amount of the alkaloid were injected into the capillary. The precipitation of

Markéta Vl?ková; Petr Barták; Vlastimil Kubá?

2004-01-01

242

Methyljasmonate accelerates catabolism of monoterpenoid indole alkaloids in Catharanthus roseus during leaf processing  

Microsoft Academic Search

Variations in alkaloid pattern during drying of leaves (leaf processing) showed that treatment with methyljasmonate can induce formation of bisindole alkaloids as a result of catabolism of the monomeric alkaloids catharanthine and vindoline. A twofold increase in 3?,4?-anhydrovinblastine was shown in treated leaves especially from day 8 until day 21. Serpentine also increased in the same period under the treatment

Magdi El-Sayed; Rob Verpoorte

2005-01-01

243

A virus-induced gene silencing approach to understanding alkaloid metabolism in Catharanthus roseus  

Microsoft Academic Search

The anticancer agents vinblastine and vincristine are bisindole alkaloids derived from coupling vindoline and catharanthine, monoterpenoid indole alkaloids produced exclusively by the Madagascar periwinkle (Catharanthus roseus). Industrial production of vinblastine and vincristine currently relies on isolation from C. roseus leaves, a process that affords these compounds in 0.0003–0.01% yields. Metabolic engineering efforts to either improve alkaloid content or provide alternative

David K. Liscombe; Sarah E. O’Connor

2011-01-01

244

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...

245

tRNA binding with anti-cancer alkaloids-nature of interaction and comparison with DNA-alkaloids adducts.  

PubMed

Vincristine and vinblastine are potent anti-proliferative compound whose mechanism of action inside a cell is not well elucidated and the basis of their differential cellular effect is also unknown. This work focuses towards understanding the interaction of vincristine and vinblastine with tRNA using spectroscopic approach. Fourier transform infrared (FTIR) spectroscopy, Fourier transform infrared difference spectroscopy and UV-visible spectroscopy were used to study the binding parameters of tRNA-alkaloids interaction. Both the vinca alkaloids interact with tRNA through external binding with some degree of intercalation into the nitrogenous bases. The alkaloids adduct formation did not alter the A-conformation of the biopolymer and vincristine-tRNA complexes were found to be more stable than that of vinblastine-tRNA complexes. The binding constants (K) estimated for VCR-tRNA and VBS-tRNA complexation are 3×10(2)M(-1) and 2.5×10(2)M(-1) respectively, which suggests low affinity of alkaloids to tRNA. The study recognizes tRNA binding properties of vital vinca alkaloids and contributes to a better understanding of their mechanism of action and could also help in identifying the reason behind their diverse action in a cell. PMID:25574589

Tyagi, Gunjan; Agarwal, Shweta; Mehrotra, Ranjana

2015-01-01

246

Monoterpene indole alkaloids from the twigs of Kopsia arborea.  

PubMed

The phytochemistry of Kopsia arborea Blume has received considerable attention, which has resulted in the isolation of a number of new unusual indole alkaloids with intriguing structures. In this study, a new eburnane-type alkaloid, phutdonginin (1), together with eight known alkaloids: 19-OH-(-)- eburnamonine (2), melodinine E (3), kopsinine (4), kopsilongine (5), kopsamine (6), (-)-methylenedioxy-1 1,12-kopsinaline (7), decarbomethoxykopsiline (8), and vincadifformine (9), were isolated from the twigs of K. arborea. Their structures were characterized extensively by 1D and 2D NMR spectroscopy and HR-ESI-MS. All compounds were submitted to TLC screening for acetylcholinesterase inhibitory activities. Only kopsamine and decarbomethoxykopsiline showed AChE inhibition with MIR values of 12.5 and 6.25 ?g, respectively, compared with galanthamine (positive control, 0.004 ?g). In addition, compounds 1 and 2 inhibited moderate antibacterial activity against E. coli TISTR 780 with the MIC value of 32 .g/mL. PMID:25522533

Cheenpracha, Sarot; Raksat, Achara; Ritthiwigrom, Thunwadee; Laphookhieo, Surat

2014-10-01

247

Activity of alkaloids on peptic ulcer: what's new?  

PubMed

Peptic ulcer is a common disease characterized by lesions that affect the mucosa of the esophagus, stomach and/or duodenum, and may extend into the muscular layer of the mucosa. Natural products have played an important role in the process of development and discovery of new drugs, due to their wide structural diversity and present, mostly specific and selective biological activities. Among natural products the alkaloids, biologically active secondary metabolites, that can be found in plants, animals or microorganisms stand out. The alkaloids are compounds consisting of a basic nitrogen atom that may or may not be part of a heterocyclic ring. This review will describe 15 alkaloids with antiulcer activity in animal models and in vitro studies. PMID:25580688

do Nascimento, Raphaela Francelino; de Sales, Igor Rafael Praxedes; de Oliveira Formiga, Rodrigo; Barbosa-Filho, José Maria; Sobral, Marianna Vieira; Tavares, Josean Fechine; Diniz, Margareth de Fátima Formiga Melo; Batista, Leônia Maria

2015-01-01

248

Pharmaceutical applications of the benzylisoquinoline alkaloids from Argemone mexicana L.  

PubMed

Argemone mexicana L. (Papaveraceae), accumulates benzylisoquinoline alkaloids, (BIA) derived from tyrosine. Although it was originated in the western region of the USA-Mexico border, it has spread to tropical and subtropical areas around the world. Today, it is used to treat different ailments, given to its antimicrobial, antiparasitic, antimalarial, pesticide, cytotoxic and neurological properties. These effects are related to the presence of different types of BIA's, such as benzophenanthridines (sanguinarine, chelerythrine), protoberberines (berberine) and protopines (protopine, allocryptopine). This review covers the historical medicinal uses of A. mexicana, as well as its current applications. The chemical bases of such effects are discussed in relation to the occurrence of the different types of alkaloids. The biochemical process involved in the synthesis of these types of alkaloids is also described. PMID:23978133

Rubio-Pina, Jorge; Vazquez-Flota, Felipe

2013-01-01

249

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

250

Pyrrolizidine alkaloids crosslink DNA with actin.  

PubMed

Pyrrolizidine alkaloids (PAs) are toxic constituents of hundreds of plant species, some of which people are exposed to in herbal products and traditional remedies. The bioactivity of PAs are related, at least in part, to their ability to form DNA-protein complexes (DPC). Previous studies from our laboratory indicated a possible role for actin in PA-induced DPCs. Nuclei prepared from Madin-Darby bovine kidney (MDBK) and human breast carcinoma (MCF-7) cells were treated with the pyrrolic PAs dehydrosenecionine (DHSN) and dehydromonocrotaline (DHMO). DPCs were purified and then analyzed by Western immunoblotting. Actin was found in DPCs induced by both DHSN and DHMO, but not in those from control nuclei. Actin was also present in DPCs induced by cisplatinum and mitomycin C, two bifunctional cross-linkers. In separate experiments, DHSN and DHMO were crosslinked to a mixture of HindIII digested lambda phage with varying amounts of glutathione (GSH), cysteine, or methionine to identify the stoichiometry of competition between DNA and alternate nucleophiles for crosslink formation with pyrroles. GSH and cysteine, but not methionine, competed with lambda phage for DNA crosslinking, indicating that reduced thiols may have a role in nucleophilic reactions with pyrroles in the cell. While actin involvement in cisplatinum-induced DPCs is documented, the discovery of actin crosslinking in PA or mitomycin C-treated cells or nuclei is, to our knowledge, novel. Pyrrole-induced DPC formation with actin, a protein with structural and/or regulatory importance proteins, may be a significant mechanism for PA toxicity and bioactivity. PMID:9925804

Coulombe, R A; Drew, G L; Stermitz, F R

1999-01-15

251

Carbazole alkaloids from the peels of Clausena lansium.  

PubMed

A new carbazole alkaloid, claulansine K (1), together with six known carbazole alkaloids (2-7), was isolated from the peels of Clausena lansium (Lour.) Skeels. The new compound was elucidated using a combination of 1D and 2D NMR (HMQC, HMBC, COSY, and ROESY) techniques, and HR-EI-MS analyses. Compound 1 showed in vitro ?-glucosidase inhibitory activity with the IC50 value of 0.11 mM. Compound 2 exhibited moderate antibacterial activity against Staphylococcus aureus with the diameter of inhibition zone of 14.2 mm. PMID:24993293

Deng, Hui-Dong; Mei, Wen-Li; Wang, Hui; Guo, Zhi-Kai; Dong, Wen-Hua; Wang, Hao; Li, Shao-Peng; Dai, Hao-Fu

2014-10-01

252

Adlumiceine methyl ester, a new alkaloid from Fumaria vaillantii.  

PubMed

A new alkaloid, adlumiceine methyl ester (1), together with two known alkaloids, parfumine (2) and N-methylhydrastine methyl ester (3), was isolated from aerial parts of Fumaria vaillantii. The structures of compounds were determined by 1D/2D NMR and MS data. All three compounds were tested for cytotoxic activity against PC3 and MCF7 cell lines using Alamar blue assay. The tested compounds showed no significant cytotoxic activity (IC50>50 ?M) against PC3 and MCF7 cell lines. PMID:25359679

Iranshahy, Milad; Javidi-Shirazi, Hamideh; Pham, Ngoc B; Quinn, Ronald J; Sadeghian, Hamid; Iranshahi, Mehrdad

2014-12-01

253

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

254

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

255

Butyrylcholinesterase, lipoxygenase inhibiting and antifungal alkaloids from Isatis tinctoria.  

PubMed

Phytochemical investigations on the alkaloidal fraction of the whole plant of the Isatis tinctoria led to the isolation of the alkaloids 1-6. Compounds 3, 2 were found to be potent butyrylcholinesterase and lipoxygenase enzymes inhibitors in a concentration-dependent manner with the IC(50) values 16.3 +/- 0.06 and 19.7 +/- 0.03 microM against BChE and 30.6 +/- 0.02 and 33.7 +/- 0.05 microM against LOX, respectively. The compounds (1-6) showed significant antifungal activity against Trichophyton schoen leinii, Aspergillus niger, Candida albicans, Trichophyton simii, and Macrophomina phaseolina. PMID:18569333

Ahmad, Ijaz; Fatima, Itrat

2008-06-01

256

Chemiluminescence detection of opium poppy (Papaver somniferum) alkaloids.  

PubMed

A review with 98 references. The determination of the opium poppy (Papaver somniferum) alkaloids and their semi-synthetic derivatives has important applications in industrial process monitoring, clinical analysis and forensic science. Liquid-phase chemiluminescence reagents such as tris(2,2'-bipyridyl)ruthenium(II) and acidic potassium permanganate exhibit remarkable sensitivity and complementary selectivity for many P. somniferum alkaloids, which has been exploited in the development of a range of analytical procedures using flow analysis, high-performance liquid chromatography, capillary electrophoresis and microfluidic instrumentation. PMID:18707837

Francis, Paul S; Adcock, Jacqui L; Costin, Jason W; Purcell, Stuart D; Pfeffer, Frederick M; Barnett, Neil W

2008-11-01

257

Quinolone and indole alkaloids from the fruits of Euodia rutaecarpa and their cytotoxicity against two human cancer cell lines.  

PubMed

Four quinolone alkaloids (1-4) and three indole alkaloids (20-22), together with 30 known alkaloids (5-19, 23-37), were isolated from the fruits of Euodia rutaecarpa. Their structures were established by spectroscopic analyses. The in vitro cytotoxic activities of these alkaloids against leukaemia HL-60 and prostate cancer PC-3 cell lines were evaluated. PMID:25457491

Zhao, Nan; Li, Zhan-Lin; Li, Da-Hong; Sun, Ya-Ting; Shan, Dong-Ting; Bai, Jiao; Pei, Yue-Hu; Jing, Yong-Kui; Hua, Hui-Ming

2015-01-01

258

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

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

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

261

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

262

Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids.  

PubMed

The communesins are a prominent class of indole alkaloids isolated from Penicillium species. Owing to their daunting structural framework and potential as pharmaceuticals, communesins have inspired numerous synthetic studies. However, the genetic and biochemical basis of communesin biosynthesis has remained unexplored. Herein, we report the identification and characterization of the communesin (cns) biosynthetic gene cluster from Penicillium expansum. We confirmed that communesin is biosynthesized by the coupling of tryptamine and aurantioclavine, two building blocks derived from L-tryptophan. The postmodification steps were mapped by targeted-gene-deletion experiments and the structural elucidation of intermediates and new analogues. Our studies set the stage for the biochemical characterization of communesin biosynthesis. This knowledge will aid our understanding of how nature generates remarkable structural complexity from simple precursors. PMID:25571861

Lin, Hsiao-Ching; Chiou, Grace; Chooi, Yit-Heng; McMahon, Travis C; Xu, Wei; Garg, Neil K; Tang, Yi

2015-03-01

263

Tobacco nicotine uptake permease (NUP1) affects alkaloid metabolism  

PubMed Central

An effective plant alkaloid chemical defense requires a variety of transport processes, but few alkaloid transporters have been characterized at the molecular level. Previously, a gene fragment encoding a putative plasma membrane proton symporter was isolated, because it was coordinately regulated with several nicotine biosynthetic genes. Here, we show that this gene fragment corresponds to a Nicotiana tabacum gene encoding a nicotine uptake permease (NUP1). NUP1 belongs to a plant-specific class of purine uptake permease-like transporters that originated after the bryophytes but before or within the lycophytes. NUP1 expressed in yeast cells preferentially transported nicotine relative to other pyridine alkaloids, tropane alkaloids, kinetin, and adenine. NUP1-GFP primarily localized to the plasma membrane of tobacco Bright Yellow-2 protoplasts. WT NUP1 transcripts accumulated to high levels in the roots, particularly in root tips. NUP1-RNAi hairy roots had reduced NUP1 mRNA accumulation levels, reduced total nicotine levels, and increased nicotine accumulation in the hairy root culture media. Regenerated NUP1-RNAi plants showed reduced foliar and root nicotine levels as well as increased seedling root elongation rates. Thus, NUP1 affected nicotine metabolism, localization, and root growth. PMID:22006310

Hildreth, Sherry B.; Gehman, Elizabeth A.; Yang, Haibing; Lu, Rong-He; K C, Ritesh; Harich, Kim C.; Yu, Shi; Sandoe, Jackson L.; Okumoto, Sakiko; Murphy, Angus S.; Jelesko, John G.

2011-01-01

264

Identification and quantitation of alkaloids in coca tea  

Microsoft Academic Search

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

Amanda J. Jenkins; Teobaldo Llosa; Ivan Montoya; Edward J. Cone

1996-01-01

265

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

266

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

267

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

268

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

269

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...

270

Determination of Hepatotoxic Pyrrolizidine Alkaloids in Gynura segetum by MEKC  

Microsoft Academic Search

A novel, rapid and sensitive micellar electrokinetic capillary chromatography method was developed for the separation and\\u000a determination of two hepatotoxic pyrrolizidine alkaloids in Gynura segetum (Lour.) Merr. (Jusanqi) within 8 min. The method was successfully applied to the simultaneous determination of seneciphylline\\u000a and senecionine in a Jusanqi sample.

Xueyong Qi; Shufang Wang; Bin Wu; Haibin Qu

2009-01-01

271

Three new carbazole alkaloids and biological activities of Murraya koenigii.  

PubMed

Three new carbazole alkaloids, mukoenigatin (1), bikoeniquinonine (2) and murrayadinal (3), were isolated from the aerial parts of Murraya koenigii, along with mukeonine-B (4). Their molecular structures were determined on the basis of spectral analysis including UV, IR, MS, and 2D NMR spectroscopy. The antimicrobial activity of different fractions of plant extract was also determined. PMID:25291407

Naz, Shaista; Saied, Sumayya; Ahmed, Afifa; Shahid, Syed Muhammad

2015-01-01

272

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

273

Lyconesidines A–C, new alkaloids from Lycopodium chinense  

Microsoft Academic Search

Three new alkaloids, lyconesidines A (1), B (2), and C (3), have been isolated from the club moss Lycopodium chinense, and the structures and absolute stereochemistry were elucidated on the basis of 2D NMR data, X-ray analysis, and modified Mosher's method.

Yusuke Hirasawa; Hiroshi Morita; Jun'ichi Kobayashi

2002-01-01

274

Diversification of ergot alkaloids in natural and modified fungi.  

PubMed

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

275

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

276

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

277

Alkaloids from leaves and stems of Vallesia glabra.  

PubMed

Eleven known indole alkaloids: vallesine, aspidospermine, 11-methoxydichotine, apparicine, tubotaïwine, vincadifformine, condylocarpine, (-)-rhazinilam, aspidospermatine, haplocidine, and 18-oxohaplocidine, have been isolated from leaves and stems of Vallesia glabra (Cav.) Link. (Apocynaceae) from Bolivia. Analysis of 2 D NMR spectra complete previous 1H and 13C data for vallesine, aspidospermine, and 11-methoxydichotine. PMID:17238065

Zèches, M; Mesbah, K; Richard, B; Moretti, C; Nuzillard, J M; Men-Olivier, L L

1995-02-01

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

[Plant from New-Caledonia. Alkaloids of Melodinus reticulatus].  

PubMed

(-)Tabersonine and (-)-11-methoxytabersonine were isolated from fruits of Melodinus reticulatus. Stems and leaves contain uvaol and eight alkaloids, five of which were previously described: (-)tabersonine, venalstonidine, kopsinine, venalstonine and its 3-oxoderivative. Three are new: 19-hydroxyvenalstonine, 19-hydroxyvenalstonidine and 3-oxovenalstonidine. PMID:17404953

Mehri, H; Rochat, C; Baassou, S; Sevenet, T; Plat, M

1983-06-01

280

Pyrrolizidine alkaloid toxicity in livestock: A paradigm for human poisoning  

Technology Transfer Automated Retrieval System (TEKTRAN)

Livestock poisoning, primarily liver damage, caused by consumption of plants containing 1,2-dehydropyrro-lizidine ester alkaloids (dehydroPAs), and the corresponding N-oxides, is a relatively common occurrence worldwide. Because of the economic impact, extensive investigations...

281

DIFFERENCES IN EFFECTS OF PYRROLIZIDINE ALKALOIDS ON FIVE GENERALIST INSECT  

E-print Network

understood. Many secondary metabolites act as defense against herbivores, and it is often postulatedDIFFERENCES IN EFFECTS OF PYRROLIZIDINE ALKALOIDS ON FIVE GENERALIST INSECT HERBIVORE SPECIES MIRKA in plant secondary compounds is often thought to be driven by insect herbivores, although there is little

Klinkhamer, Peter

282

AUSTRALINE AND RELATED ALKALOIDS: EASY STRUCTURAL CONFIRMATION AND BIOLOGICAL ACTIVITIES  

Technology Transfer Automated Retrieval System (TEKTRAN)

The first polyhydrroxylated pyrrolizidine alkaloid with a hydroxymethyl group at C-3 was isolated from pods of Alexa leiopetala (leguminosae) and designated alexine (1). The Australian legume Castanospermum australe is also known to produce the same structural type of pyrrolizidines. There are repor...

283

The alkaloid profiles of Sophora nuttalliana and Sophora stenophylla  

Technology Transfer Automated Retrieval System (TEKTRAN)

Sophora is a diverse genus in the family Fabaceae, comprised of herbs, shrubs, and trees that occurs throughout the world, primarily in the northern hemisphere. Species of Sophora are known to contain quinolizidine alkaloids that are toxic and potentially teratogenic. Two perennial herbaceous spec...

284

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

285

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

286

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

287

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

288

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...

289

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

290

Suppression of angiogenesis by the plant alkaloid, sanguinarine  

Microsoft Academic Search

Sanguinarine is a benzophenanthridine alkaloid derived from the root of Sanguinaria canadensis. Its principal pharmacologic use is in dental products where it has antibacterial, antifungal, and anti-inflammatory activities that reduce gingival inflammation and supragingival plaque formation. Angiogenesis is indispensable for inflammation, and most angiogenesis is dependent on vascular endothelial growth factor (VEGF). However, the effect of sanguinarine on angiogenesis is

Jong-Pil Eun; Gou Young Koh

2004-01-01

291

Indole alkaloid production by hairy root cultures of Catharanthus roseus  

Microsoft Academic Search

Hairy root cultures of Catharanthus roseus were established by infection with six different Agrobacterium rhizogenes strains. Two plant varieties were used and found to exhibit significantly different responses to infection. Forty-seven hairy root clones derived from normal plants and two derived from the flowerless variety were screened for their growth and indole alkaloid production. The growth rate and morphological appearance

L. Toivonen; J. Balsevich; W. G. W. Kurz

1989-01-01

292

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

293

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

294

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

295

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

296

Indole alkaloids of Rauwolfia reflexa. Carbon13 nuclear magnetic resonance structural analysis of the bis(indole) alkaloid flexicorine  

Microsoft Academic Search

The ¹³C 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.

A. Chatterjee; A. K. Ghosh; E. W. Hagaman

1982-01-01

297

Biochemistry of hemlock (Conium maculatum L.) alkaloids and their acute and chronic toxicity in livestock. A review.  

PubMed

The literature on Conium maculatum biochemistry and toxicology, dispersed in a large number of scientific publications, has been put together in this review. C. maculatum is a weed known almost worldwide by its toxicity to many domestic animals and to human beings. It is an Umbelliferae, characterized by long, hollow stems, reaching up to 2 m height at maturity, producing a large amount of lush foliage during its vegetative growth. Its flowers are white, grouped in umbels formed by numerous umbellules. It produces a large number of seeds that allow the plant to form thick stands in modified soils, sometimes encroaching on cultivated fields, to the extent of impeding the growth of any other vegetation inside the C. maculatum area of growth. Eight piperidinic alkaloids have been identified in this species. Two of them, gamma-coniceine and coniine are generally the most abundant and they account for most of the plant acute and chronic toxicity. These alkaloids are synthesized by the plant from eight acetate units from the metabolic pool, forming a polyketoacid which cyclises through an aminotransferase and forms gamma-coniceine as the parent alkaloid via reduction by a NADPH-dependent reductase. The acute toxicity is observed when animals ingest C. maculatum vegetative and flowering plants and seeds. In a short time the alkaloids produce a neuromuscular blockage conducive to death when the respiratory muscles are affected. The chronic toxicity affects only pregnant animals. When they are poisoned by C. maculatum during the fetuses organ formation period, the offspring is born with malformations, mainly palatoschisis and multiple congenital contractures (MCC; frequently described as arthrogryposis). Acute toxicity, if not lethal, may resolve in the spontaneous recovery of the affected animals provided further exposure to C. maculatum is avoided. It has been observed that poisoned animals tend to return to feed on this plant. Chronic toxicity is irreversible and although MCC can be surgically corrected in some cases, most of the malformed animals are lost. Since no specific antidote is available, prevention is the only way to deal with the production loses caused by this weed. Control with herbicides and grazing with less susceptible animals (such as sheep) have been suggested. C. maculatum alkaloids can be transferred to milk and to fowl muscle tissue through which the former can reach the human food chain. The losses produced by C. maculatum chronic toxicity may be largely underestimated, at least in some regions, because of the difficulty in associate malformations in offspring with the much earlier maternal poisoning. PMID:10340826

López, T A; Cid, M S; Bianchini, M L

1999-06-01

298

Phytochemical investigation and in vitro cytotoxic evaluation of alkaloids from Abuta rufescens.  

PubMed

A phytochemical investigation of Abuta rufescens was performed to authenticate plant material reported previously and to assess the cytotoxicity of the alkaloids obtained from the plant. Three alkaloids which have not previously been reported from this species, two phenolic (subsessiline, an oxoaporphine, and telitoxine, an azafluoranthene) and one non-phenolic (isoimerubrine, a tropoloisoquinoline), were isolated and identified. These alkaloids, along with others previously isolated from this and another Abuta species (grandirubrine, a tropoloisoquinoline), were evaluated for cytotoxic activity against several human cancer cell lines (HCT-116 colon adenocarcinoma, ACHN renal carcinoma, and A549 lung carcinoma). The tropoloisoquinoline alkaloids (grandirubrine, imerubrine, and isoimerubrine) exhibited the greatest cytotoxicity against the cell lines, especially ACHN and HCT-116 cells. The azafluoranthene alkaloid imeluteine exhibited lesser cytotoxicity, as did one of the oxoaporphine alkaloids. PMID:22109836

Swaffar, Diane S; Holley, Chad J; Fitch, Richard W; Elkin, Kyle R; Zhang, Clarice; Sturgill, Jennifer P; Menachery, Mary D

2012-02-01

299

[Use of polymerase chain reaction for searching for producers of ergot alkaloids from among microscopic fungi].  

PubMed

The potential of the polymerase chain reaction for the detection of ergot alkaloid producers among microscopic fungi of the genera Penicillium and Claviceps was evaluated. Twenty-three strains of various species of fungi with a previously studied capacity for alkaloid production were used. The internal fragment of the gene encoding 4-dimethylallyltryptophan synthase, the enzyme catalyzing the first step in the biosynthesis of ergot alkaloids, was amplified using degenerated primers. This approach revealed an about 1.2-kb specific DNA fragment in micromycetes synthesizing ergot alkaloids with complete tetracyclic ergoline system. Microorganisms that produce alkaloids with modified C or D ergoline rings, as well as alpha-cyclopiazonic acid, did not yield the PCR fragment of the expected size. This fragment was also not found in fungi incapable of ergot alkaloid production. PMID:11450458

Bo?chenko, L V; Bo?chenko, D M; Vinokurova, N G; Reshetilova, T A; Arinbasarov, M U

2001-01-01

300

Ma Huang and the Ephedra Alkaloids  

Microsoft Academic Search

Ephedra has been used as a natural medicine for thousands of years by numerous cultures with very little concern about toxicity.\\u000a Its most recent popularity is related to its purported “weight loss” or “performance enhancing” attributes. In spite of that\\u000a in 2004, concerns over safety resulted in the banning of all over-the-counter (OTC) sales of ephedra-containing dietary supplements\\u000a by the

Steven B. Karch

301

Localization of the Enzymes of Quinolizidine Alkaloid Biosynthesis in Leaf Chloroplasts of Lupinus polyphyllus1  

PubMed Central

Studies with purified chloroplasts of Lupinus polyphyllus LINDL. leaflets indicate that the first two enzymes of quinolizidine alkaloid biosynthesis, lysine decarboxylase and 17-oxosparteine synthase, are localized in the chloroplast stroma. Thus, both enzymes share the same subcellular compartment as the biosynthetic pathway of lysine, the precursor of quinolizidine alkaloids. The activity of diaminopimelate decarboxylase, the final enzyme in lysine biosynthesis, is about two to three orders of magnitude higher than that of the enzymes of alkaloid formation. PMID:16662483

Wink, Michael; Hartmann, Thomas

1982-01-01

302

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

303

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

304

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

305

A new alkaloid and other anti-implantation principles from Tabernaemontana heyneana.  

PubMed

A new alkaloid designated as ervatine, in addition to seven known alkaloids, viz. tabersonine, coronaridine, heyneanine, voacristine, voacristine hydroxyindolenine, hydroxyibogamine, and coronaridine hydroxyindolenine, were isolated from the fruit of Tabernaemontana heyneana Wall. Characterisation and structure elucidation of these compounds was made on the basis of their spectral analyses. The ethanolic extract and isolated alkaloids heyneanine and voacristine prevented pregnancy when administered during the preimplantation period in Sprague-Dawley rats. These were, however, found to possess significant uterotrophic activity. PMID:11509989

Srivastava, S; Singh, M M; Kulshreshtha, D K

2001-08-01

306

Sequestration of Veratrum alkaloids by specialist Rhadinoceraea nodicornis konow (Hymenoptera, Tenthredinidae) and its ecoethological implications  

Microsoft Academic Search

The larvae of the specialist sawflyRhadinoceraea nodicornis Konow (Hymenoptera, Tenthredinidae) store in their hemolymph ceveratrum alkaloids originating from the host plantVeratrum album L. (Liliales, Melanthiaceae). The major alkaloid found in the hemolymph is 3-acetyl-zygadenine. Qualitative and quantitative data showed that the plant alkaloid 3-angeloylzygadenine is most probably metabolized in the larval gut to zygadenine and then acetylated. A still unidentified

Urs Schaffner; Jean-Luc Boevé; Hans Gfeller; Urs P. Schlunegger

1994-01-01

307

Short?term toxicity studies of Sanguinarine and of two alkaloid extracts of Sanguinaria Canadensis L  

Microsoft Academic Search

The short?term toxicity of sanguinarine, a benzophenanthridine alkaloid, and of two alkaloid extracts of Sanguinaria canadensis L. are presented. The acute oral LD50 in rats of sanguinarine was calculated to be 1658 mg\\/kg, and of the two alkaloid extracts, 1440 and 1250 mg\\/kg. The acute iv LD50 in rats of sanguinarine was found to be 29 mg\\/kg. No toxic effects

Peter J. Becci; Harold Schwartz; Hamlin H. Barnes; G. Lee Southard

1987-01-01

308

Brominated pyrrole alkaloids from marine Agelas sponges reduce depolarization-induced cellular calcium elevation  

Microsoft Academic Search

Seven pyrrole alkaloids isolated from Agelas sponges were tested for interactions with the cellular calcium homeostasis. Brominated pyrrole alkaloids reduced voltage dependent calcium elevation in PC12 cells. Dibromosceptrin was the most potent alkaloid with a half maximal concentration of 2.8 ?M followed by sceptrin (67.5 ?M) and oroidin (75.8 ?M). 4,5-Dibromopyrrole-2-carboxylic acid reduced calcium elevation at concentrations exceeding 30 ?M

Ulf Bickmeyer; Christoph Drechsler; Matthias Köck; Michael Assmann

2004-01-01

309

Distribution of morphinan and benzo[ c]phenanthridine alkaloid gene transcript accumulation in Papaver somniferum  

Microsoft Academic Search

The opium poppy Papaver somniferum L. produces the antimicrobial benzo[c]phenanthridine alkaloid sanguinarine and the narcotic analgesic morphinan alkaloid morphine. Transcripts of three genes of alkaloid biosynthesis in P. somniferum in developing seedlings, mature plants and plant cell suspension culture were monitored for temporal\\/spatial or for methyl jasmonate-induced accumulation by RNA gel blot analysis. These genes encoded (S)-N-methylcoclaurine 3?-hydroxylase (CYP80B1) that

Fong-Chin Huang; Toni M Kutchan

2000-01-01

310

Approach to the biosynthesis of atisine-type diterpenoid alkaloids.  

PubMed

To determine the biosynthesis pathway of the atisine-type diterpenoid alkaloids spiramines A/B and C/D, feeding experiments in in vitro cultured plantlets and enzymatic transformations in cell-free extracts were performed in combination with LCMS and tandem MS analyses. L-[2-(13)C,(15)N]Serine was used in the feeding experiments and enzymatic transformations, and the diterpene spiraminol was identified as a biosynthetic precursor of spiramine alkaloids. The LCMS and tandem MS spectra of the extracts from these experiments indicated that L-[2-(13)C,(15)N]serine was incorporated into spiramines A/B and C/D. The labeled reaction products show that l-serine is the one possible nitrogen source involved in the biosynthesis of atisine-type DAs. PMID:19275222

Zhao, Pei-Ji; Gao, Suo; Fan, Li-Ming; Nie, Jing-Lei; He, Hong-Ping; Zeng, Ying; Shen, Yue-Mao; Hao, Xiao-Jiang

2009-04-01

311

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

312

Biogenetically inspired synthesis and skeletal diversification of indole alkaloids.  

PubMed

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. PMID:24345948

Mizoguchi, Haruki; Oikawa, Hideaki; Oguri, Hiroki

2014-01-01

313

Opioid peptides and opiate alkaloids in immunoregulatory processes.  

PubMed

Among the various non-neuronal cell types known to express and utilize neuropeptides, those of the immune system have received much attention in recent years. In particular, comparative studies in vertebrates and invertebrates have shown that endogenous opioid peptides are engaged in receptor mediated autoregulatory immune and neuroendocrine processes. The majority of these immune processes are stimulatory, as determined by their effects on conformational changes indicative of immunocyte activation, cellular motility, and phagocytosis. Endogenous opioid peptides form an effective network of messenger molecules in cooperation with cytokines, opiate alkaloids, and certain regulatory enzymes (neutral endopeptidase 24.11). Peptide-mediated immunostimulatory effects observed in this system are operationally counteracted by the inhibitory effects of morphine and related opiates. Opioid/opiate signaling processes are mediated by several types of receptors with different degrees of selectivity. Among them the recently identified, opioid insensitive µ(3) receptor deserves attention on account of its specificity for opiate alkaloids. PMID:22371785

Stefano, George B; Kream, Richard M

2010-06-30

314

Vinflunine: a fluorinated vinca alkaloid for bladder cancer therapy.  

PubMed

Vinflunine is a novel third-generation bifluorinated semisynthetic vinca alkaloid that has been shown to have activity against a variety of solid tumor types including advanced transitional cell carcinoma of the urothelium. In contrast to other vinca alkaloids, vinflunine shows superior antitumor activity and an excellent safety profile. Vinflunine interacts with tubulin and has a lower affinity to tubulin; it has a high intracellular accumulation rate and therefore significant effects on microtubule dynamics. A large, phase III trial comparing vinflunine with best supportive care versus best supportive care alone showed an improvement in overall survival in the vinflunine arm in preplanned secondary analyses. In addition, the drug has shown a moderate adverse event profile in the phase II and III trials. In September 2009, vinflunine was approved as a second-line treatment for patients with urothelial carcinoma resistant to first-line platinum-containing chemotherapy by the European Medicines Agency. PMID:21373647

Gerullis, H

2011-01-01

315

Stereoselective interaction of cinchona alkaloid isomers with bovine serum albumin.  

PubMed

The dependence of the interaction between bovine serum albumin (BSA) and two cinchona alkaloids, quinine (QN) and quinidine (QD), on the absolute configuration of these stereoisomers has been comprehensively studied. The FTIR spectra showed that QN and QD interacted with both CO and C-N groups of BSA, resulting in changes to the secondary structure of the protein. Fluorescence quenching of BSA by the stereoisomers revealed lower efficiency for QD in quenching the Trp emission of BSA when compared to QN. Further analysis accurately described the different binding behaviors and recognition discrepancies of QN and QD towards BSA, which was reflected through binding affinities, driving forces, energy changes and conformational changes during the ligand-protein interactions. Synchronous fluorescence further proved that QD was farther from Trp and Tyr than that of QN. This work could provide basic data for clarifying the binding interaction, metabolism and distribution of cinchona alkaloid stereoisomers in vivo. PMID:25794736

Liu, Yan; Chen, Mingmao; Jiang, Longguang; Song, Ling

2015-08-15

316

Photoreduction and ketone-sensitized reduction of alkaloids.  

PubMed

The photoprocesses of berberine, palmatine, coralyne, sanguinarine, flavopereirine and ellipticine were studied in several solvents. The quantum yields ?(?) of singlet molecular oxygen formation of berberine, palmatine and sanguinarine are moderate in dichloromethane (0.2-0.6) and much smaller in acetonitrile or trifluoroethanol. For the other alkaloids examined, ?(?) is rather independent of solvent polarity. The direct and ketone-sensitized photolysis, using steady-state irradiation at 313 nm or 248/308 nm laser pulses, was studied by absorption and fluorescence spectroscopy. Thereby, radicals were observed yielding eventually dihydro derivatives as major products, which are thermally back-converted on admission of oxygen. The quantum yield of conversion of alkaloids to dihydroalkaloids is enhanced in the presence of triethylamine. The reaction in the presence of ketones and electron or H-atom donors has a quantum yield of close to unity. PMID:21182530

Görner, Helmut; Miskolczy, Zsombor; Megyesi, Mónika; Biczók, László

2011-01-01

317

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

318

Calystegines in Calystegia sepium derive from the tropane alkaloid pathway.  

PubMed

Calystegines were measured in roots and aerial parts of Calystegia sepium. The accumulation appears developmentally regulated. Calystegine accumulation in hairy root cultures follows growth and reaches maximal values of 1,5 mg/g dry mass. 15N-Labelled tropinone was fed to root cultures and the incorporation of label into calystegines and further metabolites of the tropane alkaloid pathway was measured after 2, 4 and 6 days. Pseudotropine was completely labelled after 2 days, and calystegine A(3) was labelled faster than the calystegines of the B-group. 2,7-Dihydroxynortropane also incorporated 15N from tropinone and is suggested to be a by-product of the tropane alkaloid pathway leading to calystegines. PMID:11684185

Scholl, Y; Höke, D; Dräger, B

2001-11-01

319

Non-competitive inhibition of acetylcholinesterase by bromotyrosine alkaloids.  

PubMed

Fifteen bromotyrosine-derived alkaloids were isolated from the sponge Pseudoceratina cf. purpurea. The acetylcholinesterase-inhibiting activity of all the isolated compounds were examined; to purealidin Q, isoanomoian A, aplyzanzine A, and aplysamine 2 were active with IC50 values of 1.2, 70, 104, and 1.3 ?M, respectively. On the other hand, antiproliferative activity against MCF-7 cells of aerophobin 1 gave an IC50 value of 0.8 ?M. The Michaelis-Menten plots of the active alkaloids indicated that all the four compounds inhibited acetylcholinesterase in a non-competitive manner. The structures of the active compounds suggested that the N,N-dimethylaminopropyloxydibromotyramine moiety may play an important role in the enzyme-inhibiting activity, presumably on the anionic and hydrophobic binding sites. PMID:25532280

Olatunji, Opeyemi J; Ogundajo, Akintayo L; Oladosu, Ibrahim A; Changwichit, Kanokwan; Ingkaninan, Kornkanok; Yuenyongsawad, Supreeya; Plubrukarn, Anuchit

2014-11-01

320

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

321

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

322

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

323

?-Agarofurans and Sesquiterpene Pyridine Alkaloids from Maytenus spinosa.  

PubMed

Nine new ?-dihydroagarofurans (1-9) and four new sesquiterpene pyridine alkaloids (10-13) were isolated from the leaves of Maytenus spinosa. Their structures were determined mainly by 1D- and 2D-NMR spectroscopic studies. The absolute configuration of compound 6 was established using CD spectroscopy. Several derivatives (14-20) were prepared from the sesquiterpene 13. Most of the sesquiterpenoids were tested for anti-HIV activity, but only compound 1 was found to be active. PMID:25057904

Gutiérrez-Nicolás, Fátima; Oberti, Juan C; Ravelo, Angel G; Estévez-Braun, Ana

2014-07-24

324

Update on analytical methods for toxic pyrrolizidine alkaloids  

Microsoft Academic Search

Methods for the determination of toxic pyrrolizidine alkaloids in plants and foods are described with emphasis on the important\\u000a aspects of sample extraction and clean-up and the now preferred determination by liquid chromatography–mass spectrometry.\\u000a The efficiencies of different extraction solvents and methods are described, as are the methods of reduction of N-oxides. Appropriate liquid chromatography–mass spectrometry conditions are tabulated. This

Colin Crews; Franz Berthiller; Rudi Krska

2010-01-01

325

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

326

2-substituted quinoline alkaloids as potential antileishmanial drugs.  

PubMed Central

Ten 2-substituted quinoline alkaloids isolated from a plant used for treatment of New World cutaneous leishmaniasis have antileishmanial in vitro activities against the extracellular forms of Leishmania spp. BALB/c mice infected with Leishmania amazonensis PH8 or H-142 or Leishmania venezuelensis were treated 1 day after the parasitic infection with a quinoline alkaloid (100 mg/kg of body weight per day) or with reference drug N-methylglucamine antimonate (Glucantime) (56 mg of pentavalent antimony [Sbv] per kg per day) for 14 days. Lesion development was the criterium used to assess disease severity. Two three-carbon chain quinolines [2-n-propylquinoline and 2-(1',2'-trans-epoxypropyl)quinoline (chimanine D)] were more potent than N-methylglucamine antimonate against L. amazonensis PH8, and five quinoline alkaloids [2-(3,4-methylenedioxyphenylethyl)quinoline, cusparine, 2-(3,4-dimethoxyphenylethyl)quinoline, 2-(E)-prop-1'-enylquinoline (chimanine B), and skimmianine] were as effective as the reference drug. Single treatment near the site of infection, 14 days after infection with L. amazonensis, with 2-n-propylquinoline or chimanine B reduced the severity of lesions but less notably than N-methylglucamine antimonate. 2-n-Propylquinoline exhibited significant activity against the virulent strain L. venezuelensis. The active products did not show any apparent toxicities during the experiment. This study is, to our knowledge, the first to show the activity of 2-substituted quinoline alkaloids for experimental treatment of New World cutaneous leishmaniasis. Further investigations of these compounds might yet prove helpful for the development of new antileishmanial drugs. PMID:8494383

Fournet, A; Barrios, A A; Muñoz, V; Hocquemiller, R; Cavé, A; Bruneton, J

1993-01-01

327

New unusual alkaloids from the ascidian Eudistoma vannamei.  

PubMed

The MeOH extract of the ascidian Eudistoma vannamei was found to contain three novel compounds, the adenine alkaloid derivatives 9-[N-(leucyl)-isoleucyl]- adenine (1) and 8-hydroxy-8-isopentyl-7,8-dihydroadenine (2), and the phenylalanine peptide derivative N-[N-(leucyl)-isoleucyl]phenethylamine (3). Other previously related compounds isolated from this extract include thymidine, 2'-deoxyuridine and phenylalanine. The structures of the new compounds were elucidated through the use of NMR and mass spectrometry. PMID:25632465

Pimenta, Antônia Torres Avila; Jimenez, Paula Christine; Costa-Lotufo, Leticia Veras; Braz-Filhoc, Raimundo; Lima, Mary Anne Sousa

2014-12-01

328

Amaryllidaceae Isocarbostyril Alkaloids and Their Derivatives as Promising Antitumor Agents  

PubMed Central

This review covers the isolation, total synthesis, biologic activity, and more particularly the in vitro and in vivo antitumor activities of naturally occurring isocarbostyril alkaloids from the Amaryllidaceae family. Starting from these natural products, new derivatives have been synthesized to explore structure-activity relationships within the chemical class and to obtain potential candidates for preclinical development. This approach appears to be capable of providing novel promising anticancer agents. PMID:18607503

Ingrassia, Laurent; Lefranc, Florence; Mathieu, Véronique; Darro, Francis; Kiss, Robert

2008-01-01

329

Lycotetrastine A, a novel hexacyclic alkaloid from Huperzia tetrasticha  

Microsoft Academic Search

A novel C20N-type Lycopodium alkaloid with an unprecedented fused-hexacyclic ring system consisting of a ?-lactone, an aza-cycloheptene, an aza-cyclohexane, a cyclohexane, a cyclopentane, and tetrahydrofuran rings, lycotetrastine A (1) was isolated from the club moss of Huperzia tetrasticha. The structure and absolute stereochemistry were elucidated on the basis of 2D NMR correlations and X-ray analysis.

Yusuke Hirasawa; Adil Astulla; Motoo Shiro; Hiroshi Morita

2011-01-01

330

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

331

The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.  

PubMed

Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramolecular Diels-Alder reaction of a silicon-tethered acrylate; an efficient Stille carbonylation of a sterically encumbered vinyl triflate; a one-pot Nazarov cyclization/proto-desilylation sequence; and the chemoselective hydrogenation of a fully substituted diene ester. PMID:25756504

Shvartsbart, Artem; Smith, Amos B

2015-03-18

332

Calystegines in Calystegia sepium derive from the tropane alkaloid pathway  

Microsoft Academic Search

Calystegines were measured in roots and aerial parts of Calystegia sepium. The accumulation appears developmentally regulated. Calystegine accumulation in hairy root cultures follows growth and reaches maximal values of 1,5 mg\\/g dry mass. 15N-Labelled tropinone was fed to root cultures and the incorporation of label into calystegines and further metabolites of the tropane alkaloid pathway was measured after 2, 4

Yvonne Scholl; Dirk Höke; Birgit Dräger

2001-01-01

333

Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing Unprecedented Polyheterocyclic Cores  

PubMed Central

Enantiopure alkaloid mimics are synthesized via high yielding intramolecular cycloadditions of photogenerated azaxylylenes tethered to pyrroles, with further growth of molecular complexity via post-photochemical transformations of primary photoproducts. This expeditious access to structurally unprecedented polyheterocyclic cores is being developed in the context of diversity-oriented synthesis, as the modular design allows for rapid “pre-assembly” of diverse photoprecursors from simple building blocks/diversity inputs. PMID:23789841

Bhuvan Kumar, N.N.; Mukhina, Olga A.; Kutateladze, Andrei G.

2013-01-01

334

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

335

A new cytotoxic ?-carboline alkaloid from Galianthe thalictroides.  

PubMed

A cytotoxicity-guided fractionation of the roots of Galianthe thalictroides afforded a new ?-carboline alkaloid, 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H- ?-carbolin-1-yl)cyclopentanol, which exhibited strong cytotoxic activity against three human cancer cell lines (MCF-7, 786-0, and UACC62). Its structure was established on the basis of 1D- and 2D-NMR spectroscopic techniques supported by HRMS data. PMID:21638245

Figueiredo, Patrícia O; Garcez, Fernanda R; Matos, Maria de Fátima C; Perdomo, Renata T; Queiroz, Lyara M M; Pott, Arnildo; Garcez, Airton J S; Garcez, Walmir S

2011-11-01

336

Antimalarial diterpene alkaloids from the seeds of Caesalpinia minax.  

PubMed

Two new diterpene alkaloids, caesalminines A (1) and B (2), possessing a tetracyclic cassane-type furanoditerpenoid skeleton with ?-lactam ring, were isolated from the seeds of Caesalpinia minax. Their structures were determined by different spectroscopic methods and ECD calculation. The plausible biosynthetic pathway of caesalminines A and B was proposed. The anti-malarial activity of compounds 1 and 2 is presented with IC50 values of 0.42 and 0.79 ?M, respectively. PMID:24727083

Ma, Guoxu; Sun, Zhaocui; Sun, Zhonghao; Yuan, Jingquan; Wei, Hua; Yang, Junshan; Wu, Haifeng; Xu, Xudong

2014-06-01

337

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

338

Comparative DNA Cross-linking by Activated Pyrrolizidine Alkaloids  

Microsoft Academic Search

The toxicity and bioactivity of pyrrolizidine alkaloids (PAs), common constituents of hundreds of plant species, and in herbal remedies and folk medicines prepared thereof, are probably due to their ability to form DNA cross-linking. We investigated DNA cross-linking activity by chemically-activated PAs from four different structural classes in Madin–Darby bovine kidney (MDBK) cells and in pBR322 DNA. In cell culture,

H.-Y. Kim; F. R. Stermitz; J. K.-K. Li; R. A. Coulombe

1999-01-01

339

In vitro production of adaline and coccinelline, two defensive alkaloids from ladybird beetles (Coleoptera: Coccinellidae).  

PubMed

In vitro experiments using [1-(14)C] and [2-(14)C]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 demonstrate that these two alkaloids are most likely biosynthesised through a fatty acid rather than a polyketide pathway, that glutamine is the preferred source of the nitrogen atom and that alkaloid biosynthesis takes place in the insect fat body. PMID:12213238

Laurent, Pascal; Braekman, Jean-Claude; Daloze, Désiré; Pasteels, Jacques M

2002-09-01

340

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

2015-04-01

341

Chemical defense: Bestowal of a nuptial alkaloidal garment by a male moth on its mate  

PubMed Central

Males of the moth Cosmosoma myrodora (Arctiidae) acquire pyrrolizidine alkaloid by feeding on the excrescent fluids of certain plants (for instance, Eupatorium capillifolium). They incorporate the alkaloid systemically and as a result are protected against spiders. The males have a pair of abdominal pouches, densely packed with fine cuticular filaments, which in alkaloid-fed males are alkaloid laden. The males discharge the filaments on the female in bursts during courtship, embellishing her with alkaloid as a result. The topical investiture protects the female against spiders. Alkaloid-free filaments, from alkaloid-deprived males, convey no such protection. The males also transmit alkaloid to the female by seminal infusion. The systemic alkaloid thus received, which itself may contribute to the female's defense against spiders, is bestowed in part by the female on the eggs. Although paternal contribution to egg defense had previously been demonstrated for several arctiid moths, protective nuptial festooning of a female by its mate, such as is practiced by C. myrodora, appears to be without parallel among insects. PMID:11114202

Conner, William E.; Boada, Ruth; Schroeder, Frank C.; González, Andrés; Meinwald, Jerrold; Eisner, Thomas

2000-01-01

342

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

343

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

344

Distribution of opiate alkaloids in brain tissue of experimental animals  

PubMed Central

The present study examined regional distribution of opiate alkaloids from seized heroin in brain regions of experimental animals in order to select parts with the highest content of opiates. Their analysis should contribute to resolve causes of death due to heroin intake. The tests were performed at different time periods (5, 15, 45 and 120 min) after male and female Wistar rats were treated with seized heroin. Opiate alkaloids (codeine, morphine, acetylcodeine, 6-acetylmorphine and 3,6-diacetylmorphine) were quantitatively determined in brain regions known for their high concentration of µ-opiate receptors: cortex, brainstem, amygdala and basal ganglia, by using gas chromatography–mass spectrometry (GC–MS). The highest content of opiate alkaloids in the brain tissue of female animals was found 15 min and in male animals 45 min after treatment. The highest content of opiates was determined in the basal ganglia of the animals of both genders, indicating that this part of brain tissue presents a reliable sample for identifying and assessing contents of opiates after heroin intake. PMID:23554560

Pilija, Vladimir; Mimica-Dukic, Neda; Budakov, Branislav; Cvjeticanin, Stanko

2012-01-01

345

Effects of alkaloidal extract of Phyllanthus niruri on HIV replication.  

PubMed

Phyllanthus niruri has been found to exhibit marked inhibitory effect on hepatitis B virus evident by its exhaustive utility in cases of chronic jaundice. However, till date, research has not been focused on identification and validation of active pharmacophores of Phyllanthus niruri responsible for the reported inhibitory effect of its aqueous extract on anti-human immunodeficiency virus. The present investigation examines the anti-HIV effects of the alkaloidal extract of Phyllanthus niruri in human cell lines. The inhibitory effect on HIV replication was monitored in terms of inhibition of virus induced cytopathogenecity in MT-4 cells. The alkaloidal extract of Phyllanthus niruri showed suppressing activity on strains of HIV-1 cells cultured on MT-4 cell lines. The CC50 for the extract was found to be 279.85 microgmL(-1) whereas the EC50 was found to be 20.98 microgmL(-1). Interestingly the Selectivity Index (SI) was found to be 13.34, which showed a clear selective toxicity of the extract for the viral cells. The alkaloidal extract of Phyllanthus niruri was thus found to exhibit sensitive inhibitory response on cytopathic effects induced by both the strains of human immunodeficiency virus on human MT-4 cells in the tested concentrations. PMID:14515028

Naik, A D; Juvekar, A R

2003-09-01

346

Detoxification of pyrrolizidine alkaloids by the harvestman Mitopus morio (Phalangidae) a predator of alkaloid defended leaf beetles  

Microsoft Academic Search

Summary. The harvestman Mitopus morio (Phalangidae) is a generalist predator. It is known to prey on larvae of the chrysomelid leaf beetle Oreina cacaliae defended by plant acquired pyrrolizidine alkaloids (PAs). Tracer feeding experiments were performed to determine how harvestmen tolerate protoxic PAs. Minced meat containing either [ 14C]senecionine or [ 14C]senecionine N-oxide was fed to M. morio and subsequently

Thomas Hartmann; Håkan Häggström; Claudine Theuring; Rainer Lindigkeit; Martine Rahier

2003-01-01

347

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

348

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

349

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...

350

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

351

Plant-symbiotic fungi as chemical engineers: multi-genome analysis of the Clavicipitaceae reveals dynamics of alkaloid loci  

Technology Transfer Automated Retrieval System (TEKTRAN)

The fungal family Clavicipitaceae includes plant symbionts and pathogens that produce neurotropic alkaloids with diverse effects on vertebrate and invertebrate animals. For example, ergot alkaloids are historically linked to mass poisonings (St. Anthony's fire) and sociological effects such as the ...

352

Characterization of a Suspension Culture of Tabernaemontana elegans on Growth, Nutrient Uptake, and Accumulation of Indole Alkaloids*.  

PubMed

A suspension culture of TABERNAEMONTANA ELEGANS was characterized on growth, nutrient uptake (carbohydrate, nitrogen, and phosphate), and on accumulation of indole alkaloids. Besides tryptamine seven indole alkaloids were isolated and identified: vobasine, vobasinol, perivine, isositsirikine, apparicine, tubotaiwine, and O-acetylvallesamine. In spite of the presence of vobasinol as major product, only trace amounts of dimeric indole alkaloids could be detected. Alkaloid formation started at the early stationary phase. PMID:17262332

van der Heijden, R; Louwe, C L; Verhey, E R; Harkes, P A; Verpoorte, R

1989-04-01

353

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

354

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

355

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

356

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

357

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

358

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.

359

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

360

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...

361

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

362

Method validation for determination of alkaloid content in goldenseal root powder.  

PubMed

A fast, practical ambient extraction methodology followed by isocratic liquid chromatography (LC) analysis with UV detection was validated for the determination of berberine, hydrastine, and canadine in goldenseal (Hydrastis canadensis L.) root powder. The method was also validated for palmatine, a major alkaloid present in the possible bioadulterants Coptis, Oregon grape root, and barberry bark. Alkaloid standard solutions were linear over the evaluated concentration ranges. The analytical method was linear for alkaloid extraction using 0.3-2 g goldenseal root powder/100 mL extraction solvent. Precision of the method was demonstrated using 10 replicate extractions of 0.5 g goldenseal root powder, with percent relative standard deviation for all 4 alkaloids < or = 1.6. Alkaloid recovery was determined by spiking each alkaloid into triplicate aliquots of neat goldenseal root powder. Recoveries ranged from 92.3% for palmatine to 101.9% for hydrastine. Ruggedness of the method was evaluated by performing multiple analyses of goldenseal root powder from 3 suppliers over a 2-year period. The method was also used to analyze Coptis root, Oregon grape root, barberry bark, and celandine herb, which are possible goldenseal bioadulterants. The resulting chromatographic profiles of the bioadulterants were significantly different from that of goldenseal. The method was directly transferred to LC with mass spectrometry, which was used to confirm the presence of goldenseal alkaloids tetrahydroberberastine, berberastine, canadaline, berberine, hydrastine, and canadine, as well as alkaloids from the bioadulterants, including palmatine, jatrorrhizine, and coptisine. PMID:12852562

Weber, Holly A; Zart, Matthew K; Hodges, Andrew E; White, Kellie D; Barnes, Sarah M; Moody, Leslie A; Clark, Alice P; Harris, Roger K; Overstreet, J Diane; Smith, Cynthia S

2003-01-01

363

Livestock Poisoning with Pyrrolizidine Alkaloid Containing Plants (Senecio, Crotalaria, Cynoglossum, Amsinckia, Heliotropium and Echium spp.)  

Technology Transfer Automated Retrieval System (TEKTRAN)

Pyrrolizidine alkaloids (PAs) are potent liver toxins that have been identified in over 6,000 plants throughout the world. Alkaloids are nitrogen-based compounds with potent biological activity. About half of the identified PAs are toxic and several cause cancer (carcinogenic). PA-containing plants...

364

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

365

Synthesis and pharmacological activity of alkaloids from embryo of lotus, Nelumbo nucifera.  

PubMed

Bisbenzylisoquinoline alkaloid, nelumboferine which was recently isolated from the embryo of Nelumbo nucifera, and stereoisomers of neferine, which is a major alkaloid of the embryo of N. nucifera, were stereoselectively synthesized. Pharmacological activity of nelumboferine, stereoisomers of neferine, liensinine, isoliensinine, and O-methylneferine were evaluated. PMID:23117579

Nishimura, Katsumi; Horii, Shinji; Tanahashi, Takao; Sugimoto, Yumi; Yamada, Jun

2013-01-01

366

The toxicity of Poison Dart Frog alkaloids against the Fire Ant (Solenopsis invicta)  

Technology Transfer Automated Retrieval System (TEKTRAN)

Hundreds of alkaloids, representing over 20 structural classes, have been identified from the skin of neotropical poison frogs (Dendrobatidae). These alkaloids are derived from arthropod prey of the frogs, and are generally are believed to deter vertebrate predators. We developed a method to put ind...

367

Dietary exposure to ergot alkaloids decreases contractility of bovine mesenteric vasculature  

Technology Transfer Automated Retrieval System (TEKTRAN)

Ergot alkaloids are hypothesized to cause vasoconstriction in the midgut, and prior exposure may affect the vasoactivity of these compounds. The objectives of this study were to profile vasoactivity of ergot alkaloids in bovine mesenteric artery (MA) and vein (MV) and determine if previous exposure ...

368

Repeated Evolution of the Pyrrolizidine Alkaloid-Mediated Defense System in Separate Angiosperm Lineages  

Microsoft Academic Search

Species of several unrelated families within the angiosperms are able to constitutively produce pyrrolizidine alkaloids as a defense against herbivores. In pyrrolizidine alkaloid (PA) biosynthesis, homospermidine synthase (HSS) catalyzes the first specific step. HSS was recruited during angiosperm evolution from deoxyhypusine synthase (DHS), an enzyme involved in the posttranslational activation of eukaryotic initiation factor 5A. Phylogenetic analysis of 23 cDNA

Andreas Reimann; Niknik Nurhayati; Anita Backenkohler; Dietrich Ober

2004-01-01

369

Attract and deter: a dual role for pyrrolizidine alkaloids in plant–insect interactions  

Microsoft Academic Search

Pyrrolizidine alkaloids (PAs) are the major defense compounds of plants in the Senecio genus. Here I will review the effects of PAs in Senecio on the preference and performance of specialist and generalist insect herbivores. Specialist herbivores have evolved adaptation\\u000a to PAs in their host plant. They can use the alkaloids as cue to find their host plant and often

Mirka Macel

2011-01-01

370

Evidence for the monophyletic evolution of benzylisoquinoline alkaloid biosynthesis in angiosperms  

Microsoft Academic Search

Benzylisoquinoline alkaloids (BIAs) consist of more than 2500 diverse structures largely restricted to the order Ranunculales and the eumagnoliids. However, BIAs also occur in the Rutaceae, Lauraceae, Cornaceae and Nelumbonaceae, and sporadically throughout the order Piperales. Several of these alkaloids function in the defense of plants against herbivores and pathogens – thus, the capacity for BIA biosynthesis is expected to

David K. Liscombe; Benjamin P. MacLeod; Natalia Loukanina; Owi I. Nandi; Peter J. Facchini

2005-01-01

371

Effect of ergot alkaloids from fungal endophyte-infected grasses on fall armyworm ( Spodoptera frugiperda )  

Microsoft Academic Search

Ergot alkaloids produced by endophytic fungi in the tribe Balansiae (Clavicipitaceae, Ascomycetes), which infect grasses, may provide plant defense against herbivores. This study examined the effects of six ergot alkaloids on survivorship, feeding, and growth of larvae of the fall armyworm (Spodoptera frugiperda, Lepidoptera: Noctuidae), a generalist herbivore of grasses. Corn leaf disks were soaked in solutions of individual ergot

Keith Clay; Gregory P. Cheplick

1989-01-01

372

Pyrrolizidine alkaloid biosynthesis, evolution of a pathway in plant secondary metabolism  

Microsoft Academic Search

The system of pyrrolizidine alkaloids has proven to be a powerful system for studying the evolution of a biosynthetic pathway in plant secondary metabolism. Pyrrolizidine alkaloids are typical plant secondary products produced by the plant as a defense against herbivores. The first specific enzyme, homospermidine synthase, has been shown to have evolved by duplication of the gene encoding deoxyhypusine synthase,

Dietrich Ober; Elisabeth Kaltenegger

2009-01-01

373

Plant alkaloids that cause developmental defects through the disruption of cholinergic neurotransmission  

Technology Transfer Automated Retrieval System (TEKTRAN)

The exposure of a developing embryo or fetus to alkaloids from plants, plant products, or plant extracts has the potential to cause developmental defects in humans and animals. These defects may have multiple causes but those induced by piperidine and quinolizidine alkaloids arise from the inhibiti...

374

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...

375

Heterozygous P53 knockout mouse model for dehydropyrrolizidine alkaloid-induced carcinogenesis  

Technology Transfer Automated Retrieval System (TEKTRAN)

Dehydropyrrolizidine alkaloids are a large, structurally diverse group of plant-derived protoxins that are potentially carcinogenic. With worldwide significance, these alkaloids can contaminate or be naturally present in the human food supply. To develop a small animal model that may be used to com...

376

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

377

Role of the LolP Cytochrome P450 Monooxygenase in Loline Alkaloid Biosynthesis  

Technology Transfer Automated Retrieval System (TEKTRAN)

The insecticidal loline alkaloids, produced by Neotyphodium uncinatum and related endophytes, are exo-1-aminopyrrolizidines with an ether bridge between C-2 and C-7. Loline alkaloids vary in methyl, acetyl, and formyl substituents on the 1-amine, which affect their biological activity. Enzymes for k...

378

New quinolizidine and diaza-adamantane alkaloids from Acosmium dasycarpum (Vog.) Yakovlev—Fabaceae  

Microsoft Academic Search

The phytochemical investigation of the methanol crude extract obtained from Acosmium dasycarpum (Vog.) Yakovlev root bark led to the isolation of the quinolizidine alkaloids lupanine, acosmine, acosminine and lupanacosmine, as well as the diaza-adamantane alkaloids panacosmine and dasycarpumine. Lupanacosmine (4) and dasycarpumine (6) have been described for the first time herein.

Tânia Cecília Trevisan; Eliane A. Silva; Evandro Luiz Dall’Oglio; Luiz Everson da Silva; Eudes da Silva Velozo; Paulo Cezar Vieira; Paulo Teixeira de Sousa Jr.

2008-01-01

379

Ten new fawcettimine-related alkaloids from three species of Lycopodium  

Microsoft Academic Search

Ten new fawcettimine-related alkaloids, i.e., lycopoclavamines, lycoposquarrosamine-A, and other hydroxylated fawcettimine derivatives, were isolated from three species of Lycopodium (Lycopodium clavatum, Lycopodium serratum, and Lycopodium squarrosum). The structures of the new alkaloids were elucidated by spectroscopic methods and chemical correlation.

Kazuaki Katakawa; Hiroko Mito; Noriyuki Kogure; Mariko Kitajima; Sumphan Wongseripipatana; Munehisa Arisawa; Hiromitsu Takayama

2011-01-01

380

Purealidin S and purpuramine J, bromotyrosine alkaloids from the Fijian marine sponge Druinella sp.  

PubMed

Two bromotyrosine alkaloids, purealidin S (2) and purpuramine J (5), were isolated from the Fijian marine sponge Druinella sp. Eight known bromotyrosine compounds were also isolated. This is the first report of a bromotyrosine N-oxide containing alkaloid. These two compounds were found to have moderate cytotoxic activity. In addition, bioassay data for the eight known bromotyrosine metabolites are reported. PMID:12502317

Tabudravu, Jioji N; Jaspars, Marcel

2002-12-01

381

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

382

Functional characterisation of genes involved in pyridine alkaloid biosynthesis in tobacco  

Microsoft Academic Search

Although secondary metabolism in Nicotiana tabacum (L.) (tobacco) is rather well studied, many molecular aspects of the biosynthetic pathways and their regulation remain to be disclosed, even for prominent compounds such as nicotine and other pyridine alkaloids. To identify players in tobacco pyridine alkaloid biosynthesis a functional screen was performed, starting from a tobacco gene collection established previously by means

Suvi T. Häkkinen; Sofie Tilleman; Agnieszka Šwi?tek; Valerie De Sutter; Heiko Rischer; Isabelle Vanhoutte; Harry Van Onckelen; Pierre Hilson; Dirk Inzé; Kirsi-Marja Oksman-Caldentey; Alain Goossens

2007-01-01

383

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

384

Alkaloid Accumulation in Catharanthus roseus Increases with Addition of Seawater Salts to the Nutrient Solution  

Microsoft Academic Search

A sand culture experiment was conducted to determine the effects of different seawater (5% and 10%) treatments on plant growth, inorganic ions, indole alkaloid concentrations and yields of Catharanthus roseus, in an effort to increase the alkaloid yield by artificial cultivation. The total fresh and dry weights and tissue K+ concentrations decreased, but Na+ concentrations increased in the plant roots,

Jing-Yan WANG; Zhao-Pu LIU

2010-01-01

385

Transcriptome analysis in Catharanthus roseus leaves and roots for comparative terpenoid indole alkaloid profiles  

Microsoft Academic Search

In Catharanthus roseus (L.) G. Don each tissue is known to produce a distinct spectrum of terpenoid indole alkaloids. Since the invaluable antineoplastic bisindole alkaloids are restricted to the aerial parts of the plant and do not occur in its underground tissues, identification of the structural and regulatory factors operating distinctly in the shoot\\/leaf of the plant will be a

Ashutosh K. Shukla; Ajit K. Shasany; Madan M. Gupta; Suman P. S. Khanuja

2006-01-01

386

Genetic Variability and Interrelationship Among Opium and its Alkaloids in Opium Poppy ( Papaver Somniferum L.)  

Microsoft Academic Search

Summary  The plant species Papaver somniferum L. (opium poppy) is grown commercially in several countries under secure area to produce opium and its major alkaloids i.e. morphine, codeine, thebaine, narcotine and papaverine for pharmaceutical industries. In recent years the global demand for these alkaloids and its derivatives are growing. Seeing the global demand there is urgent need to develop high opium

Hemant K. Yadav; S. Shukla; S. P. Singh

2006-01-01

387

O-Demethylation as a Biosynthetic Pattern in the Formation of Opium Alkaloids  

Microsoft Academic Search

COMPARATIVE rates of incorporation of carbon dioxide labelled with carbon-14 led to the proposal1 that, in Papaver somniferum, thebaine is the first octahydrophenanthrene alkaloid formed, and is converted by successive O-demethylations to codeine and finally to morphine. Although this sequence seemed best to explain the labelling ratio among these three alkaloids, conclusive proof was lacking. The results described here, considered

Frank R. Stermitz; Henry Rapoport

1961-01-01

388

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

389

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

390

Pyrrolizidine alkaloids in Crotalaria taxa from northern Australia: risk to grazing livestock.  

PubMed

Crotalaria species containing hepatotoxic pyrrolizidine alkaloids grow widely in pastures in northern Australia and have sporadically poisoned grazing livestock. The diverse Crotalaria taxa present in these pastures include varieties, subspecies, and chemotypes not previously chemically examined. This paper reports the pyrrolizidine alkaloid composition and content of 24 Crotalaria taxa from this region and assesses the risk of poisoning in livestock consuming them. Alkaloids present in C. goreensis , C. aridicola subsp. densifolia, and C. medicaginea var. neglecta lack the esterified 1,2-unsaturated functionality required for pyrrole adduct formation, and these taxa are not hepatotoxic. Taxa with high levels of hepatotoxic alkaloids, abundance, and biomass pose the greatest risk to livestock health, particularly C. novae-hollandiae subsp. novae-hollandiae, C. ramosissima , C. retusa var. retusa, and C. crispata . Other species containing moderate alkaloid levels, C. spectabilis and C. mitchellii , also pose significant risk when locally abundant. PMID:19061310

Fletcher, Mary T; McKenzie, Ross A; Blaney, Barry J; Reichmann, Keith G

2009-01-14

391

Biogenetically-inspired total synthesis of epidithiodiketopiperazines and related alkaloids.  

PubMed

Natural products chemistry has historically been the prime arena for the discovery of new chemical transformations and the fountain of insights into key biological processes. It remains a fervent incubator of progress in the fields of chemistry and biology and an exchange mediating the flow of ideas between these allied fields of science. It is with this ethos that our group has taken an interest in and pursued the synthesis of a complex family of natural products termed the dimeric epipolythiodiketopiperazine (ETP) alkaloids. We present here an Account of the highly complex target molecules to which we pegged our ambitions, our systematic and relentless efforts toward those goals, the chemistry we developed in their pursuit, and the insight we have gained for their translational potential as potent anticancer molecules. The dimeric ETP alkaloids are fungal metabolites that feature a highly complex molecular architecture comprising a densely functionalized core structure with many stereogenic centers, six of which are fully substituted, and a pair of vicinal quaternary carbon stereocenters, decorated on polycyclic architectures in addition to the unique ETP motif that has been recognized as acid-, base-, and redox-sensitive. A cyclo-dipeptide consisting of an essential tryptophan residue and a highly variable ancillary amino acid lies at the core of these structures; investigation of the transformations that take this simplistic core to the complex alkaloids lies at the heart of our research program. The dimeric epidithiodiketopiperazine alkaloids have largely resisted synthesis on account of their complexity since the 1970s when the founding members of this class, chaetocin A ( Hauser , D. et al. Helv. Chim. Acta 1970 , 53 , 1061 ) and verticillin A ( Katagiri , K. et al. J. Antibiot. 1970 , 23 , 420 ), were first isolated. This was despite their potent cytotoxic and bacteriostatic activities, which were well appreciated at the time of their discovery. In the past decade, an increasing number of studies have uncovered powerful new biological processes that these molecules can uniquely effect, such as the inhibition of histone methyltransferases by chaetocin A ( Greiner , D. et al. Nat. Chem. Biol. 2005 , 1 , 143 ). In fact, the complete collection of hexahydropyrroloindoline alkaloids features a diverse range of potent biological properties including cytotoxic, antitumor, antileukemic, antiviral, antibiotic, and antinematodal activities ( Jiang , C.-S. ; Guo , Y.-W. Mini-Rev. Med. Chem. 2011 , 11 , 728 ). This mélange of activities is reflective of their structural diversity. Under the precepts of retrobiosynthetic analysis, we have accomplished the syntheses of more than a dozen natural products, including members of the bionectin, calycanthaceous, chaetocin, gliocladin, naseseazine, and verticillin alkaloids. More importantly, these molecules have acted as venerable venues for the development of new strategies to address structural challenges including, but not limited to, C3-C3' vicinal quaternary centers, heterodimeric linkages, C3-Csp(2) linkages, diketopiperazine oxidation, stereoselective thiolation, homologue-specific polysulfidation, and C12-hydroxyl incorporation. Synthesis of these natural products has resulted in the structural confirmation, and sometimes revision such as the case of (+)-naseseazines A and B, as well as access to many plausible biogenetically relevant intermediates and new synthetic ETP derivatives. Furthermore, our studies have paved the way for the formulation of a comprehensive SAR profile and the identification of lead compounds with in vitro subnanomolar IC50's against a broad range of cancer types. PMID:25843276

Kim, Justin; Movassaghi, Mohammad

2015-04-21

392

Bromopyrrole Alkaloids as Lead Compounds against Protozoan Parasites  

PubMed Central

In the present study, 13 bromopyrrole alkaloids, including the oroidin analogs hymenidin (2), dispacamide B (3) and dispacamide D (4), stevensine (5) and spongiacidin B (6), their derivatives lacking the imidazole ring bromoaldisin (7), longamide B (8) and longamide A (9), the dimeric oroidin derivatives sceptrin (10) and dibromopalau’amine (11), and the non-oroidin bromopyrrolohomoarginin (12), manzacidin A (13), and agelongine (14), obtained from marine sponges belonging to Axinella and Agelas genera have been screened in vitro against four parasitic protozoa, i.e., two Trypanosoma species (T. brucei rhodesiense and T. cruzi), Leishmania donovani and Plasmodium falciparum (K1 strain, a chloroquine resistant strain), responsible of human diseases with high morbidity and, in the case of malaria, high mortality. Our results indicate longamide B (8) and dibromopalau’amine (11) to be promising trypanocidal and antileishmanial agents, while dispacamide B (3) and spongiacidin B (6) emerge as antimalarial lead compounds. In addition, evaluation of the activity of the test alkaloids (2–14) against three different enzymes (PfFabI, PfFabG, PfFabZ) involved in the de novo fatty acid biosynthesis pathway of P. falciparum (PfFAS-II) identified bromopyrrolohomoarginin (12) as a potent inhibitor of PfFabZ. The structural similarity within the series of tested molecules allowed us to draw some preliminary structure-activity relationships. Tests against the mammalian L6 cells revealed important clues on therapeutic index of the metabolites. This is the first detailed study on the antiprotozoal potential of marine bromopyrrole alkaloids. PMID:20714430

Scala, Fernando; Fattorusso, Ernesto; Menna, Marialuisa; Taglialatela-Scafati, Orazio; Tierney, Michelle; Kaiser, Marcel; Tasdemir, Deniz

2010-01-01

393

Tall fescue seed extraction and partial purification of ergot alkaloids  

NASA Astrophysics Data System (ADS)

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. 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) and the hexane fraction was discarded. 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.

Bush, Lowell

2014-12-01

394

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

395

Tyrosine aminotransferase contributes to benzylisoquinoline alkaloid biosynthesis in opium poppy.  

PubMed

Tyrosine aminotransferase (TyrAT) catalyzes the transamination of L-Tyr and ?-ketoglutarate, yielding 4-hydroxyphenylpyruvic acid and L-glutamate. The decarboxylation product of 4-hydroxyphenylpyruvic acid, 4-hydroxyphenylacetaldehyde, is a precursor to a large and diverse group of natural products known collectively as benzylisoquinoline alkaloids (BIAs). We have isolated and characterized a TyrAT cDNA from opium poppy (Papaver somniferum), which remains the only commercial source for several pharmaceutical BIAs, including codeine, morphine, and noscapine. TyrAT belongs to group I pyridoxal 5'-phosphate (PLP)-dependent enzymes wherein Schiff base formation occurs between PLP and a specific Lys residue. The amino acid sequence of TyrAT showed considerable homology to other putative plant TyrATs, although few of these have been functionally characterized. Purified, recombinant TyrAT displayed a molecular mass of approximately 46 kD and a substrate preference for L-Tyr and ?-ketoglutarate, with apparent K(m) values of 1.82 and 0.35 mm, respectively. No specific requirement for PLP was detected in vitro. Liquid chromatography-tandem mass spectrometry confirmed the conversion of L-Tyr to 4-hydroxyphenylpyruvate. TyrAT gene transcripts were most abundant in roots and stems of mature opium poppy plants. Virus-induced gene silencing was used to evaluate the contribution of TyrAT to BIA metabolism in opium poppy. TyrAT transcript levels were reduced by at least 80% in silenced plants compared with controls and showed a moderate reduction in total alkaloid content. The modest correlation between transcript levels and BIA accumulation in opium poppy supports a role for TyrAT in the generation of alkaloid precursors, but it also suggests the occurrence of other sources for 4-hydroxyphenylacetaldehyde. PMID:21949209

Lee, Eun-Jeong; Facchini, Peter J

2011-11-01

396

Opium poppy and Madagascar periwinkle: model non-model systems to investigate alkaloid biosynthesis in plants.  

PubMed

Alkaloids represent a large and diverse group of compounds that are related by the occurrence of a nitrogen atom within a heterocyclic backbone. Unlike other types of secondary metabolites, the various structural categories of alkaloids are unrelated in terms of biosynthesis and evolution. Although the biology of each group is unique, common patterns have become apparent. Opium poppy (Papaver somniferum), which produces several benzylisoquinoline alkaloids, and Madagascar periwinkle (Catharanthus roseus), which accumulates an array of monoterpenoid indole alkaloids, have emerged as the premier organisms used to study plant alkaloid metabolism. The status of these species as model systems results from decades of research on the chemistry, enzymology and molecular biology responsible for the biosynthesis of valuable pharmaceutical alkaloids. Opium poppy remains the only commercial source for morphine, codeine and semi-synthetic analgesics, such as oxycodone, derived from thebaine. Catharanthus roseus is the only source for the anti-cancer drugs vinblastine and vincristine. Impressive collections of cDNAs encoding biosynthetic enzymes and regulatory proteins involved in the formation of benzylisoquinoline and monoterpenoid indole alkaloids are now available, and the rate of gene discovery has accelerated with the application of genomics. Such tools have allowed the establishment of models that describe the complex cell biology of alkaloid metabolism in these important medicinal plants. A suite of biotechnological resources, including genetic transformation protocols, has allowed the application of metabolic engineering to modify the alkaloid content of these and related species. An overview of recent progress on benzylisoquinoline and monoterpenoid indole alkaloid biosynthesis in opium poppy and C. roseus is presented. PMID:18476877

Facchini, Peter J; De Luca, Vincenzo

2008-05-01

397

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

398

One-pot synthesis of vinca alkaloids-phomopsin hybrids.  

PubMed

Hybrids of vinca alkaloids and phomopsin A have been elaborated with the aim of interfering with the "vinca site" and the "peptide site" of the vinca domain in tubulin. They were synthesized by an efficient one-pot procedure that directly links the octahydrophomopsin lateral chain to the velbenamine moiety of 7'-homo-anhydrovinblastine. In their modeled complexes with tubulin, these hybrids were found to superimpose nicely on the tubulin-bound structures of vinblastine and phomopsin A. This good matching can account for the fact that two of them are very potent inhibitors of microtubules assembly and are cytotoxic against four cancer cell lines. PMID:24871162

Gherbovet, Olga; Coderch, Claire; García Alvarez, María Concepción; Bignon, Jérôme; Thoret, Sylviane; Guéritte, Françoise; Gago, Federico; Roussi, Fanny

2014-06-26

399

The Effect of Polyhydroxylated Alkaloids on Maltase-Glucoamylase  

PubMed Central

One of the most important carbohydrate-splitting enzymes is themaltase-glucoamylase which catalyzes the hydrolysis of alpha-glucosidic linkages. Maltase-glucoamylase inhibitors during the last few years have aroused medical interests in the treatment of diabetes. They contribute to a better understanding of the mechanism of maltase-glucoamylase. At present there are many different classes of maltase-glucoamylase inhibitors. This paper focuses on alkaloidal inhibitors of maltase-glucoamylase and structure-activity relationship (SAR) studies between them in order to discover some drugs with better efficiency and lower toxicity for treating diabetes. PMID:23967118

Shang, Qian; Xiang, Junfeng; Zhang, Hong; Li, Qian; Tang, Yalin

2013-01-01

400

Total Synthesis of a Marine Alkaloid—Rigidin E  

PubMed Central

In the present paper, we report an efficient total synthesis of a marine alkaloid, rigidin E. The key tetrasubstituted 2-amino-3-carboxamidepyrrole intermediate was synthesized by cascade Michael addition/intramolecular cyclization between N-(2-(4-(benzyloxy)phenyl)-2-oxoethyl)methanesulfonamide and 3-(4-(benzyloxy)phenyl)-2-cyano-N-methylacrylamide. Subsequent carbonylation with triphosgene catalyzed by I2 and deprotection of benzyl groups afforded rigidin E in 21% overall yield. This strategy has the merits of metal-free reactions, low cost, mild reaction protocols, and easy access to diversity-oriented derivatives for potential structure-activity relationship investigation. PMID:22822382

Cao, Banpeng; Ding, Haixin; Yang, Ruchun; Wang, Xiaoji; Xiao, Qiang

2012-01-01

401

New selective acetylcholinesterase inhibitors designed from natural piperidine alkaloids.  

PubMed

Five new piperidine alkaloids were designed from natural (-)-3-O-acetyl-spectaline and (-)-spectaline that were obtained from the flowers of Senna spectabilis (sin. Cassia spectabilis, Leguminosae). Two semi-synthetic analogues (7 and 9) inhibited rat brain acetylcholinesterase, showing IC50 of 7.32 and 15.1 microM, and were 21 and 9.5 times less potent against rat brain butyrylcholinesterase, respectively. Compound 9 (1mg/kg, i.p.) was fully efficacious in reverting scopolamine-induced amnesia in mice. The two active compounds (7 and 9) did not show overt toxic effects at the doses tested in vivo. PMID:15878668

Viegas, Cláudio; Bolzani, Vanderlan S; Pimentel, Luísa S B; Castro, Newton G; Cabral, Rafael F; Costa, Rodrigo S; Floyd, Corinne; Rocha, Mônica S; Young, Maria C M; Barreiro, Eliezer J; Fraga, Carlos A M

2005-07-01

402

Asymmetric total synthesis of apocynaceae hydrocarbazole alkaloids (+)-deethylibophyllidine and (+)-limaspermidine.  

PubMed

An unprecedented asymmetric catalytic tandem aminolysis/aza-Michael addition reaction of spirocyclic para-dienoneimides has been designed and developed through organocatalytic enantioselective desymmetrization. A unified strategy based on this key tandem methodology has been divergently explored for the asymmetric total synthesis of two natural Apocynaceae alkaloids, (+)-deethylibophyllidine and (+)-limaspermidine. The present studies not only enrich the tandem reaction design concerning the asymmetric catalytic assembly of a chiral all-carbon quaternary stereocenter contained in the densely functionalized hydrocarbazole synthons but also manifest the potential for the application of the asymmetric catalysis based on the para-dienone chemistry in asymmetric synthesis of natural products. PMID:25767939

Du, Ji-Yuan; Zeng, Chao; Han, Xiao-Jie; Qu, Hu; Zhao, Xian-He; An, Xian-Tao; Fan, Chun-An

2015-04-01

403

Alkaloid production by hairy root cultures in Atropa belladonna.  

PubMed

Hairy roots were induced by inoculation of stems of sterile plants of Atropa belladonna with Agrobacterium rhizogenes. The axenic culture of the hairy roots isolated from the stems proliferated 60 fold as based on the initial fresh weight after one month of culture. The presence of atropine and scopolamine in hairy roots were examined by TLC and HPLC. Their amounts were analyzed by GLC. The results show that the amount of the two alkaloids in the axenic cultures was the same as or even higher than those of normal plants grown in the field. PMID:24248236

Kamada, H; Okamura, N; Satake, M; Harada, H; Shimomura, K

1986-08-01

404

Aconitum and Delphinium alkaloids of curare-like activity. QSAR analysis and molecular docking of alkaloids into AChBP.  

PubMed

Early studies have shown that some of diterpenoid alkaloids, found in highly toxic plants of the genera Aconitum and Delphinium, act at neuronal nicotinic acetylcholine receptors (nAChRs) and exhibit potent N-cholinolytic activity. In the current study, GA-MLRA and GA-PLS approaches have been used to build QSAR models to predict N-cholinolytic activity measured in vivo (blockade of neuromuscular conductivity, BNMC and third eyelid relaxing activity, TYRA) and in vitro (suppression of frog's abdominal straight muscles on acetylcholine, SAM) for a series of diterpenoid alkaloids. Random splitting of a data set (five trials in total) produced QSAR models of a good level of correlation between experimental in vitro/in vivo and calculated N-cholinolytic activity expressed as log(1/ED(50)) with following average statistical parameters: log BNMC (r(2) = 0.87, s = 0.14, q(2) = 0.82), log TYRA (r(2) = 0.80, s = 0.29, q(2) = 0.67), log SAM (r(2) = 0.84, s = 29, q(2) = 0.64). QSAR results suggest descriptors accounting for H-bond capability of molecules influence all three type of N-cholinolytic activity with additional contribution of steric and reactivity features as identified for TYRA and SAM data, respectively. The alkaloid-receptor complexes were further analyzed by means of AutoDock Vina docking program using the binding site of MLA complexed with AChBP (homolog of the ligand binding domain of nAChRs) as template. All compounds were shown to be well fitted in the binding pocket of native MLA with good correlation exhibited between their ED(50) and AutoDock Vina binding free energy. An analysis of the possible factors significant for the ligand recognition has been enhanced by comparative docking studies performed for structurally related lycoctonine-type alkaloids (lappaconitine and aconitine) that are known to bind to voltage-gated Na(+) channel, but not to nAChRs. PMID:20594622

Turabekova, M A; Rasulev, B F; Dzhakhangirov, F N; Leszczynska, D; Leszczynski, J

2010-09-01

405

Geographic and seasonal variation in alkaloid-based chemical defenses of Dendrobates pumilio from Bocas del Toro, Panama.  

PubMed

Poison frogs contain an alkaloid-based chemical defense that is derived from a diet of certain alkaloid-containing arthropods, which include mites, ants, beetles, and millipedes. Variation in population-level alkaloid profiles among species has been documented, and more than 800 different alkaloids have been identified. In the present study, we examine individual alkaloid variation in the dendrobatid poison frog Dendrobates pumilio among seven populations and between two seasons on Isla Bastimentos, located in the Bocas del Toro archipelago of Panama. Alkaloid profiles vary among populations and between seasons, illustrating that chemical defense in this species can vary on a small spatial and temporal scale. Alkaloid variation among populations is marginally correlated with geographic distance, and close populations have profiles more similar to each other than to distant populations. Individuals within populations also vary in alkaloid profiles. Differences are attributed to both spatial and temporal variations in the availability of alkaloid-containing arthropods. Many of the alkaloids present in the skin of D. pumilio appear likely to be of ant origin, supporting the importance of myrmecophagy in chemical defense among poison frogs. However, a variety of frog skin alkaloids was recently detected in mites, suggesting that mites may also play an important role in chemical defense. PMID:16718571

Saporito, Ralph A; Donnelly, Maureen A; Garraffo, H Martin; Spande, Thomas F; Daly, John W

2006-04-01

406

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

407

The total synthesis of the Galbulimima alkaloid GB 13.  

PubMed

This contribution describes a synthetic approach to alkaloid GB 13, previously isolated from the North Australian and Papua New Guinean rain forest tree Galbulimima belgraveana. A Birch reductive alkylation of 2,5-dimethoxybenzoic acid by 3-methoxybenzyl bromide, followed by an acid-catalyzed cyclization was used to synthesize the [3.3.1]bicyclononane 8. A ring contraction performed on the diazo derivative 9 of the [3.3.1]bicyclononane led to [3.2.1]bicyclooctane 10. This [3.2.1]bicyclooctane was converted into a dienophile and subjected to a Diels-Alder reaction to generate a pentacyclic intermediate 13 with a carbon skeleton closely resembling the target alkaloid. The surplus substituent, required for activation and regioselectivity in the Diels-Alder reaction, was removed using Birch reductive conditions to effect a decyanation. It was discovered that a Birch reduction of the aromatic ring also present in the molecule could be performed at the same time to give the enone 15, which was cleaved by means of an Eschenmoser fragmentation. The piperidine ring found in the natural product was formed by reductive cyclization of the bis-oxime 18 derived from the alkynyl ketone 17 and the resulting material further elaborated to GB 13 (1) via ketone 20. PMID:12603121

Mander, Lewis N; McLachlan, Matthew M

2003-03-01

408

Isoquinoline alkaloid production by transformed cultures of Papaver somniferum.  

PubMed

Three clones of transformed cultures of opium poppy (Papaver somniferum L.) were established by infection with Agrobacterium rhizogenes MAFF 03-01724. MAFF clone 1 being capable of forming somatic embryos was selected and its growth and isoquinoline alkaloid production was investigated. The illumination, temperature and nutrient medium composition greatly affected growth, cell morphology and alkaloid accumulation. The MAFF clone 1 cultured in Root Culture medium in the dark at 22 degrees C accumulated a high quantity of sanguinarine (652 micrograms/g dry weight) though the growth was poor (4.4 fold as fresh weight basis after 2 months of culture). The MAFF clone 1 cultured in a quarter macro salt strength Woody Plant medium under 14 h/day light at 22 degrees C developed into plantlets and accumulated significant quantity of codeine (648 micrograms/g dry wt) together with papaverine, noscapine, and sanguinarine. This clone was applied to a rotating drum fermenter (2 L working volume), and ca. 0.3 mg codeine and 0.06 mg sanguinarine were obtained after 4 weeks of culture. One quarter of the codeine produced was found in the culture medium. PMID:11915285

Yoshimatsu, K; Shimomura, K

2001-01-01

409

Induction of tropane alkaloid formation in transformed root cultures of Brugmansia suaveolens (Solanaceae).  

PubMed

Hairy root cultures of Brugmansia suaveolens were set up by infection of root tips with Agrobacterium rhizogenes. The successful transformation was confirmed by analysing rolC and virC genes using polymerase chain reaction (PCR). Hairy root cultures were employed to study the formation of tropane alkaloids, such as hyoscyamine. The transformed cultures were incubated with potential elicitors, such as methyljasmonate, quercetin and salicylic acid in order to stimulate the biosynthesis of tropane alkaloids. Profile and amounts of tropane alkaloids were analysed using capillary GLC-MS. At least 18 different tropane alkaloids could be identified. Treatment of the cultures with 200 microM methyljasmonate increased the alkaloid accumulation 25-fold up to a level of 1 mg/g fresh weight as compared to untreated controls. Quercetin enhanced the alkaloid production 10 fold (0.4 mg/g fresh weight) within 24 h. In contrast 100 microM salicylic acid decreased alkaloids to a level of 1 microg/g fresh weight. PMID:15666547

Zayed, Rawia; Wink, Michael

2004-01-01

410

Chemical and antiviral study on alkaloids from Papaver pseudocanescens M. Pop.  

PubMed

The phytochemical investigation of the aerial parts of Papaver pseudocanescens M. Pop. of Mongolian origin resulted in the isolation and structural elucidation of 8 alkaloids of the isoquinoline and promorphinane type. 8,14-Dihydroamurine, 8,14-dihydroflavinantine, and flavinantine are promorphinanes. Alborine, mecambridine, and mecambridine methohydroxide are retroprotoberberines. Amurensinine is an isopavine alkaloid and O-methylarmepavine is a benzylisoquinoline alkaloid. O-Methylarmepavine is a new alkaloid for the genus Papaver. Promorphinane-type alkaloids have been found for the first time in the species. All structures were established by physical and spectral analysis. As a first attempt to describe some of the biological activities of these alkaloids, the antiviral effect was tested against the in vitro replication of several viruses which belong to different taxonomic groups and represent significant human pathogens. Based on the results, the conclusion could be drawn that particular alkaloids from P. pseudocanescens possess selective antiviral effects against the replication of poliovirus 1 and human rhinovirus 14, two viruses from the Enterovirus genus of the Picornaviridae family. PMID:22486038

Istatkova, Ralitsa; Nikolaeva-Glomb, Lubomira; Galabov, Angel; Yadamsuren, Gerelt-Od; Samdan, Javzan; Dangaa, Selenge; Philipov, Stefan

2012-01-01

411

Root-to-shoot translocation of alkaloids is dominantly suppressed in Nicotiana alata.  

PubMed

In tobacco (Nicotiana tabacum), nicotine and related pyridine alkaloids are produced in the root, and then transported to the aerial parts where these toxic chemicals function as part of chemical defense against insect herbivory. Although a few tobacco transporters have been recently reported to take up nicotine into the vacuole from the cytoplasm or into the cytoplasm from the apoplast, it is not known how the long-range translocation of tobacco alkaloids between organs is controlled. Nicotiana langsdorffii and N. alata are closely related species of diploid Nicotiana section Alatae, but the latter does not accumulate tobacco alkaloids in the leaf. We show here that N. alata does synthesize alkaloids in the root, but lacks the capacity to mobilize the root-borne alkaloids to the aerial parts. Interspecific grafting experiments between N. alata and N. langsdorffii indicate that roots of N. alata are unable to translocate alkaloids to their shoot system. Interestingly, genetic studies involving interspecific hybrids between N. alata and N. langsdorffii and their self-crossed or back-crossed progeny showed that the non-translocation phenotype is dominant over the translocation phenotype. These results indicate that a mechanism to retain tobacco alkaloids within the root organ has evolved in N. alata, which may represent an interesting strategy to control the distribution of secondary products within a whole plant. PMID:22555816

Pakdeechanuan, Phattharaporn; Shoji, Tsubasa; Hashimoto, Takashi

2012-07-01

412

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

413

Alkaloid biosynthesis in Papaver sp. cells in culture and during organogenesis.  

PubMed

In vitro cell cultures of two Papaver species, P. somniferum and P. bracteatum initiated from mature seeds were screened for their ability to produce alkaloids. Protocols for callus induction, somatic embryogenesis and organogenesis were established. The alkaloid contents were analysed by high-performance-liquid chromatography, thin-layer chromatography and spectrophotometric assays. Undifferentiated callus produced small amounts of sanguinarine, which increased with the degree of tissue differentiation. Embryogenic calli were maintained in culture for more than 2 years, retaining a high regeneration capability. Thin-layer chromatography analysis revealed variations in alkaloid spectrum between parallel cell lines. The morphinan alkaloid, thebaine, was found to be accumulated exclusively in morphogenous strains of P. bracteatum, and morphine was the major alkaloid in the spectrum of P. somniferum dedifferentiated callus. Regenerant plants synthesized thebaine and sanguinarine at the same level as juvenile plants grown from P. bracteatum seeds. We revealed differences in the ability to produce different types of alkaloids: seed-derived plants were able to accumulate thebaine while undifferentiated primary cell cultures produced only sanguinarine. The production of either sanguinarine and morphinan alkaloids are found in regenerants showing that both metabolic pathways were active in young plantlets. PMID:12035546

Alkhimova, O G; Kyrylenko, T K; Vagyn, Y V; Heslop-Harrison, J S

2001-01-01

414

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

415

The Biogeographical Distribution of Duncecap Larkspur (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...

416

Serum Elimination Profiles of Methyllycaconitine and Deltaline in Cattle Following Oral Administration of Larkspur (Delphinium barbeyi)  

Technology Transfer Automated Retrieval System (TEKTRAN)

The objectives of this study were to describe the simple elimination kinetics of two abundant norditerpenoid alkaloids in larkspur, MLA and deltaline, and measure the heart rate response of intoxicated cattle over 96 hours. Five Angus steers halter broke, gentled, and habituated to metabolism crate...

417

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.

418

Structure-Activity Relationship of Benzophenanthridine Alkaloids from Zanthoxylum rhoifolium Having Antimicrobial Activity  

PubMed Central

Zanthoxylum rhoifolium (Rutaceae) is a plant alkaloid that grows in South America and has been used in Brazilian traditional medicine for the treatment of different health problems. The present study was designed to evaluate the antimicrobial activity of the steam bark crude methanol extract, fractions, and pure alkaloids of Z. rhoifolium. Its stem bark extracts exhibited a broad spectrum of antimicrobial activity, ranging from 12.5 to 100 µg/mL using bioautography method, and from 125 to 500 µg/mL in the microdilution bioassay. From the dichloromethane basic fraction, three furoquinoline alkaloids (1–3), and nine benzophenanthridine alkaloids (4–12) were isolated and the antimicrobial activity of the benzophenanthridine alkaloids is discussed in terms of structure-activity relationships. The alkaloid with the widest spectrum of activity was chelerythrine (10), followed by avicine (12) and dihydrochelerythrine (4). The minimal inhibitory concentrations of chelerythrine, of 1.50 µg/mL for all bacteria tested, and between 3.12 and 6.25 µg/mL for the yeast tested, show this compound to be a more powerful antimicrobial agent when compared with the other active alkaloids isolated from Z. rhoifolium. To verify the potential importance of the methylenedioxy group (ring A) of these alkaloids, chelerythrine was selected to represent the remainder of the benzophenanthridine alkaloids isolated in this work and was subjected to a demethylation reaction giving derivative 14. Compared to chelerythrine, the derivative (14) was less active against the tested bacteria and fungi. Kinetic measurements of the bacteriolytic activities of chelerythrine against the bacteria Bacillus subtilis (Gram-positive) and Escherichia coli (Gram-negative) were determined by optical density based on real time assay, suggesting that its mechanism of action is not bacteriolytic. The present study did not detect hemolytic effects of chelerythrine on erythrocytes and found a protective effect considering the decrease in TBARS and AOPP (advanced oxidized protein products) levels when compared to the control group. PMID:24824737

Tavares, Luciana de C.; Zanon, Graciane; Weber, Andréia D.; Neto, Alexandre T.; Mostardeiro, Clarice P.; Da Cruz, Ivana B. M.; Oliveira, Raul M.; Ilha, Vinicius; Dalcol, Ionara I.; Morel, Ademir F.

2014-01-01

419

Naturally-occurring tetrahydro-?-carboline alkaloids derived from tryptophan are oxidized to bioactive ?-carboline alkaloids by heme peroxidases.  

PubMed

?-Carbolines are indole alkaloids that occur in plants, foods, and endogenously in mammals and humans, and which exhibit potent biological, psychopharmacological and toxicological activities. They form from naturally-occurring tetrahydro-?-carboline alkaloids arising from tryptophan by still unknown way and mechanism. Results in this research show that heme peroxidases catalyzed the oxidation of tetrahydro-?-carbolines (i.e. 1,2,3,4-tetrahydro-?-carboline-3-carboxylic acid and 1-methyl-1,2,3,4-tetrahydro-?-carboline-3-carboxylic acid) into aromatic ?-carbolines (i.e. norharman and harman, respectively). This oxidation followed a typical catalytic cycle of peroxidases through redox intermediates I, II, and ferric enzyme. Both, plant peroxidases (horseradish peroxidase, HRP) and mammalian peroxidases (myeloperoxidase, MPO and lactoperoxidase, LPO) catalyzed the oxidation in an efficient manner as determined by kinetic parameters (VMAX and KM). Oxidation of tetrahydro-?-carbolines was inhibited by peroxidase inhibitors such as sodium azide, ascorbic acid, hydroxylamine and excess of H2O2. The formation of aromatic ?-carbolines by heme peroxidases can help to explain the presence and activity of these compounds in biological systems. PMID:25035927

Herraiz, Tomás; Galisteo, Juan

2014-08-15

420

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

421

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

422

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

423

Naturally occurring plant isoquinoline N-oxide alkaloids: their pharmacological and SAR activities.  

PubMed

The present review describes research on novel natural isoquinoline alkaloids and their N-oxides isolated from different plant species. More than 200 biological active compounds have shown confirmed antimicrobial, antibacterial, antitumor, and other activities. The structures, origins, and reported biological activities of a selection of isoquinoline N-oxides alkaloids are reviewed. With the computer program PASS some additional SAR (structure-activity relationship) activities are also predicted, which point toward new possible applications of these compounds. This review emphasizes the role of isoquinoline N-oxides alkaloids as an important source of leads for drug discovery. PMID:25636889

Dembitsky, Valery M; Gloriozova, Tatyana A; Poroikov, Vladimir V

2015-01-15

424

Acquisition, transformation and maintenance of plant pyrrolizidine alkaloids by the polyphagous arctiid Grammia geneura.  

PubMed

The polyphagous arctiid Grammia geneura appears well adapted to utilize for its protection plant pyrrolizidine alkaloids of almost all known structural types. Plant-acquired alkaloids that are maintained through all life-stages include various classes of macrocyclic diesters (typically occurring in the Asteraceae tribe Senecioneae and Fabaceae), macrocyclic triesters (Apocynaceae) and open-chain esters of the lycopsamine type (Asteraceae tribe Eupatorieae, Boraginaceae and Apocynaceae). As in other arctiids, all sequestered and processed pyrrolizidine alkaloids are maintained as non-toxic N-oxides. The only type of pyrrolizidine alkaloids that is neither sequestered nor metabolized are the pro-toxic otonecine-derivatives, e.g. the senecionine analog senkirkine that cannot be detoxified by N-oxidation. In its sequestration behavior, G. geneura resembles the previously studied highly polyphagous Estigmene acrea. Both arctiids are adapted to exploit pyrrolizidine alkaloid-containing plants as "drug sources". However, unlike E. acrea, G. geneura is not known to synthesize the pyrrolizidine-derived male courtship pheromone, hydroxydanaidal, and differs distinctly in its metabolic processing of the plant-acquired alkaloids. Necine bases obtained from plant acquired pyrrolizidine alkaloids are re-esterified yielding two distinct classes of insect-specific ester alkaloids, the creatonotines, also present in E. acrea, and the callimorphines, missing in E. acrea. The creatonotines are preferentially found in pupae; in adults they are largely replaced by the callimorphines. Before eclosion the creatonotines are apparently converted into the callimorphines by trans-esterification. Open-chain ester alkaloids such as the platynecine ester sarracine and the orchid alkaloid phalaenopsine, that do not possess the unique necic acid moiety of the lycopsamine type, are sequestered by larvae but they need to be converted into the respective creatonotines and callimorphines by trans-esterification in order to be transferred to the adult stage. In the case of the orchid alkaloids, evidence is presented that during this processing the necine base (trachelanthamidine) is converted into its 7-(R)-hydroxy derivative (turneforcidine), indicating the ability of G. geneura to introduce a hydroxyl group at C-7 of a necine base. The creatonotines and callimorphines display a striking similarity to plant necine monoesters of the lycopsamine type to which G. geneura is well adapted. The possible function of insect-specific trans-esterification in the acquisition of necine bases derived from plant acquired alkaloids, especially from those that cannot be maintained through all life-stages, is discussed. PMID:16102415

Hartmann, T; Theuring, C; Beuerle, T; Bernays, E A; Singer, M S

2005-10-01

425

Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis  

Microsoft Academic Search

Syntheses of (2S,12?R)-2-(12?-aminotridecyl)-pyrrolidine (1) and (2S,12?R)-1-(2?-hydroxyethyl)-2-(12?-aminotridecyl)-pyrrolidine (2), two defensive alkaloids recently isolated from the Mexican bean beetle, Epilachna varivestis, are described. By a comparison of 1H NMR data of MTPA derivatives of natural alkaloid 2 with those of the synthetic standard, we confirm the (2S,12?R) configuration previously suggested for this alkaloid. Further support of these assignments was provided by the

Xiongwei Shi; Athula B. Attygalle; Ferrold Meinwald

1997-01-01

426

Unified Total Syntheses of Fawcettimine Class Alkaloids: Fawcettimine, Fawcettidine, Lycoflexine, and Lycoposerramine B  

PubMed Central

The total syntheses of the lycopodium alkaloids: fawcettimine, fawcettidine, lycoflexine, and lycoposerramine B have been accomplished through an efficient, unified, and stereocontrolled strategy, which 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.

2012-01-01

427

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

428

Methods for regeneration and transformation in Eschscholzia californica: A model plant to investigate alkaloid biosynthesis.  

PubMed

Eschscholzia californica Cham. (California poppy) is a plant species that accumulates pharmacologically active alkaloids biosynthetically related to the morphinan alkaloids of Papaver somniferum. This, in combination with the relative ease with which it is propagated in vitro, makes it a key model for benzylisoquinoline biosynthesis. Transformation techniques are an important tool for these studies and for metabolic engineering attempts. Agrobacterium mediated transformation techniques for this model species have been developed in our lab and used for modulation of transcript levels relevant to the biosynthesis of these alkaloids. Here we describe the techniques used in our lab for production of transgenic callus, hairy root cultures, and whole plants. PMID:16673930

MacLeod, Benjamin P; Facchini, Peter J

2006-01-01

429

Alkaloids of young ponderosa pine seedlings and late steps in the biosynthesis of pinidine  

Microsoft Academic Search

The pattern of ponderosa pine (Pinus ponderosa) piperidine alkaloid accumulation from seeds to 28-day-old seedlings was assessed. Seeds were devoid of alkaloids but eight-day-old seedlings contained several alkaloids whose concentrations remained low with continued growth, while the concentration of pinidine [cis-2-methyl-6-(2-propenyl)-piperidine] steadily increased. 13C-Labelled cis-pinidinone [cis-2-methyl-6-(2-oxopropyl)-piperidine] was taken up through seedling roots and was incorporated into pinidine.

Jeanne N. Tawara; Frank R. Stermitz; Andrei V. Blokhin

1995-01-01

430

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.

Dr Gene Tagliarini

431

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

432

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.

433

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

434

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

2014-01-01

435

Alkaloids from the Australian rainforest tree Ochrosia moorei.  

PubMed

High-throughput screening of a plant and marine invertebrate extract library to find natural products that down-regulate expression of pro-inflammatory genes associated with the glucocorticoid receptor ligand complex led to the identification of bioactive CH2Cl 2 extracts from stems and leaves of the Queensland tree Ochrosia moorei. Bioassay-guided purification of the stem extract enabled the isolation of four alkaloids including two new compounds, ochrosamines A (1) and B (2), and the known compounds ellipticine (3) and 9-methoxyellipticine (4). The leaf extract also afforded 3 and 4 as well as apparicine (5) and desoxycordifoline (6). The structures of the two new compounds were assigned from interpretation of 2D NMR and high-resolution ESIMS data. Ellipticine and 9-methoxyellipticine were the most active components, and both displayed IC 50 values of 90 microM. Apparicine and desoxycordifoline were only very weakly active, and ochrosamines A and B were inactive. PMID:18412397

Carroll, Anthony R; Addepalli, Rama; Fechner, Gregory; Smith, Jill; Guymer, Gordon P; Forster, Paul I; Quinn, Ronald J

2008-06-01

436

New Quinolinone Alkaloids from Chestnut (Castanea crenata Sieb) Honey.  

PubMed

Two new quinolinone alkaloids and 13 known compounds were isolated from chestnut (Castanea crenata Sieb) honey. Two new compounds were determined to be 3-dihydro-spiro[2(1H),3'(1'H)-diquinoline]-3',4,4'-trione (spirodiquinolinone) and 3-(2'-piperidine)-kynurenic acid. In addition, 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one was identified for the first time from nature. In addition, 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one was newly identified from chestnut honey, although this compound has been synthesized before. The structures were determined by the NMR and electrospray ionization-mass spectroscopy (ESI-MS). Three compounds were qualified and quantitated in chestnut honey by selective multiple reaction monitoring (MRM) detection of LC-ESI-MS using the isolated compounds as external standards. PMID:25797069

Cho, Jeong-Yong; Bae, Sun-Hee; Kim, Hye-Kyung; Lee, Myeong-Lyeol; Choi, Yong-Soo; Jin, Byung-Rae; Lee, Hyoung Jae; Jeong, Hang Yeon; Lee, Yu Geon; Moon, Jae-Hak

2015-04-01

437

Canthinone alkaloids are novel protein tyrosine phosphatase 1B inhibitors.  

PubMed

Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes. Screening of a natural compound library resulted in six canthinone alkaloids, namely, picrasidine L (1), 3,4-dimethyl-canthin-5,6-dione (2), 4-ethyl-3-methyl-canthin-5,6-dione (3), eurycomine E (4), 5-methoxy-canthin-6-one (5), and 5-acethoxy-canthin-6-one (6), as novel PTP1B inhibitors. Among these, 1 is the competitive PTP1B inhibitor with the best inhibitory selectivity between PTP1B and other PTPs and was shown to promote activity in the insulin signaling pathway in cell-based assays. Molecular docking simulations and structure-activity relationship analysis of 1 will add to its potential as a lead compound in future anti-insulin-resistant drug developments. PMID:25819098

Sasaki, Tatsunori; Li, Wei; Higai, Koji; Koike, Kazuo

2015-05-01

438

A concise total synthesis of the azaphenanthrene alkaloid eupolauramine.  

PubMed

A six-step total synthesis of the azaphenanthrene alkaloid eupolauramine 1 has been achieved using combinational metalation-cyclization tactics. The synthetic route involved first the construction of the azaisoindolinone 9 by aryne-mediated cyclization of he phosphorylated pyridocarboxamide 7 and subsequent dephosphorylation. Metalation of 9 followed by connection of the hydroxybenzyl appendage and E(1)CB anti-elimination allowed the formation of the halogenoarylmethylene azaisoindolinone 4 in the exclusive E-form. Oxidative radical cyclization gave rise to the azaphenanthrene skeleton and regioselective bromination of 3 induced the incorporation of the bromine atom at the 6-position of the azaphenanthrene lactam. Ultimate replacement of the bromine atom of 2 by the methoxy functionality by sequential transmetalation, in situ oxidation, and O-methylation of the phenolic derivative 14 completed the synthesis of the target natural product eupolauramine. PMID:11722206

Hoarau, C; Couture, A; Cornet, H; Deniau, E; Grandclaudon, P

2001-11-30

439

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

440

Development of Transcriptomic Resources for Interrogating the Biosynthesis of Monoterpene Indole Alkaloids in Medicinal Plant Species  

E-print Network

The natural diversity of plant metabolism has long been a source for human medicines. One group of plant-derived compounds, the monoterpene indole alkaloids (MIAs), includes well-documented therapeutic agents used in the ...

Gongora-Castillo, Elsa

441

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

E-print Network

compounds. Introduction Plants in the Amaryllidaceae family have been used for thousands of years as herbal remedies; the ancient Greeks knew their medicinal value.2 The alkaloids from their extracts have been

Hudlicky, Tomas

442

Variability in the yield of benzophenanthridine alkaloids in wildcrafted vs cultivated bloodroot (Sanguinaria canadensis L.).  

PubMed

Populations of bloodroot [Sanguinaria canadensis L. (Papaveraceae)] are found throughout the eastern forests of North America, with particular abundance in the southern Appalachian Mountains. Increasingly, it is finding use in Europe as a nonantibiotic animal feed supplement to promote weight gain. As efforts to cultivate this herb are underway, there is a need to understand the effect of agronomic permutations on both the dry mass rhizome yield and the yield of benzophenanthridine alkaloids. Month-to-month variability of the concentration of the alkaloids sanguinarine and chelerythrine in both cultivated and wildcrafted bloodroot was examined. The alkaloid yield was consistently higher, but more variable, in wildcrafted plants. On average, cultivated rhizomes were both larger and more consistently sized than those that were wildcrafted. The concentration of a suite of trace elements was measured in soil that was collected concomitantly with each plant accession. Differences in element profiles were compared against alkaloid yields. PMID:17253712

Graf, Tyler N; Levine, Keith E; Andrews, Margaret E; Perlmutter, Jason M; Nielsen, Samara Joy; Davis, Jeanine M; Wani, Mansukh C; Oberlies, Nicholas H

2007-02-21

443

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

444

Effect of certain elicitors on production of pyrrolizidine alkaloids in hairy root cultures of Echium rauwolfii.  

PubMed

Hairy root cultures of Echium rauwolfii were obtained by infection of sterile apical shoots with Agrobacterium rhizogenes. The linear increase in fresh weight was found to be parallel to the alkaloids production. The transformed cultures were exposed to different elicitors, such as methyl jasmonate (MJ), quercetin and salicylic acid in order to increase their productivity. Pyrrolizidine alkaloids were quantitatively determined by HPLC. Estimation of total alkaloids was achieved by peak area calculations. MJ at a concentration of 100 microM induced the accumulation of total alkaloids about 19-fold compared to the untreated control. The flavonoid quercetin (Q) at a concentration of 50 microM enhanced the pyrrolizidine accumulation approximately 6-fold. The induction effect of both MJ and Q can be suppressed by pre-incubation of hairy root cultures with salicylic acid. PMID:20383945

Abd El-Mawla, A M A

2010-03-01

445

Poor alkaloid sequestration by arrow poison frogs of the genus Phyllobates from Costa Rica.  

PubMed

Frogs of the genus Phyllobates from Colombia are known to contain the highly toxic alkaloid batrachotoxin, but species from Central America exhibit only very low levels or are entirely free of this toxin. In the present study alcohol extracts from 101 specimens of Phyllobates lugubris and Phyllobates vittatus and 21 of three sympatric species (Dendrobates pumilio, Dendrobates auratus, Dendrobates granuliferus) from Costa Rica were analyzed by gas chromatography-mass spectrometry. Whereas the extracts of the Dendrobates species exhibited typical profiles of toxic alkaloids, those of the two Phyllobates species contained low levels of few alkaloids only, batrachotoxin was not detected. Although the feeding pattern of the Dendrobates and Phyllobates species are similar as revealed by examination of their stomach content (mainly ants and mites), the Phyllobates species are poorly sequestering alkaloids from their food source in contrast to the Dendrobates frogs. PMID:24467995

Mebs, Dietrich; Alvarez, Joseph Vargas; Pogoda, Werner; Toennes, Stefan W; Köhler, Gunther

2014-03-01

446

Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.  

PubMed

The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis. PMID:12031432

Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

2002-06-01

447

Thesinine-4?- O-?- d-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis  

Microsoft Academic Search

The glycosylated pyrrolizidine alkaloid, thesinine-4?-O-?-d-glucoside, has been isolated from the aqueous methanolic extract of dried seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analyses.

Martina Herrmann; Holger Joppe; Gerhard Schmaus

2002-01-01

448

Indolizidine 239Q and Quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus)  

PubMed Central

Alkaloid profiles in skin of poison frogs/toads (Dendrobatidae, Mantellidae, Bufonidae, and Myobatrachidae) are highly dependent on diet and hence on the nature of habitat. Extracts of the two species of toads (Melanophryniscus klappenbachi and M. cupreuscapularis) from similar habitats in the Corrientes/Chaco Provinces of Argentina have similar profiles of alkaloids, which differ considerably from profiles from other Melanophryniscus species from Brazil, Uruguay and Argentina. Structures of two major alkaloids 239Q (1) and 275I (2) were determined by mass, FTIR, and NMR spectral analysis as 5Z,9Z-3-(1-hydroxybutyl)-5-propylindolizidine and 6Z,10E-4,6-di(pent-4-enyl) quinolizidine, respectively. A third alkaloid, 249F (3), is postulated to be a homopumiliotoxin with an unprecedented conjugated exocyclic diene moiety. PMID:18848574

Daly, John W.; Garraffo, H. Martin; Spande, Thomas F.; Yeh, Herman J. C.; Peltzer, Paola M.; Cacivio, Pedro; Baldo, J. Diego; Faivovich, Julián

2008-01-01

449

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

450

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

451

Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species  

PubMed Central

Background The growing popularity of Chinese herbal medicine in the United States has prompted large-scale import of raw herbs from Asia. Many of the Asian herbs have phylogenetically related North American species. We compared three phylogenetically related species, namely Coptis chinensis (Huanglian), Hydrastis canadensis and Coptis trifolia to show whether they can be substituted by one another in terms of alkaloid content. Methods We used microwave assisted extraction to obtain alkaloids berberine, coptisine, palmatine and hydrastine. High performance liquid chromatography (HPLC) was used to quantify each alkaloid. Results Hydrastis canadensis has the most berberine, whereas Coptis trifolia has the most coptisine. Hydrastine and palmatine were unique to Hydrastis canadensis and Coptis chinensis respectively. Conclusion Neither Hydrastis canadensis nor Coptis trifolia contains all the alkaloids found in Coptis chinensis used in Chinese medicine. Substitutes of this Chinese species by its American relatives are not recommended. PMID:19703289

Kamath, Shreya; Skeels, Matthew; Pai, Aswini

2009-01-01

452

The laser desorption/laser ionization mass spectra of some indole derivatives and alkaloids  

NASA Astrophysics Data System (ADS)

The laser desorption and laser ionization mass spectra of some indole derivatives and alkaloids are described with particular reference to their modes of fragmentation. Mass spectra of yohimbine, reserpine, quinine and quinidine are presented. Full experimental details are given.

Rogers, Kevin; Milnes, John; Gormally, John

1992-06-01

453

In vivo antimalarial efficacy of acetogenins, alkaloids and flavonoids enriched fractions from Annona crassiflora Mart.  

PubMed

Annona crassiflora and Annonaceae plants are known to be used to treat malaria by traditional healers. In this work, the antimalarial efficacy of different fractions of A. crassiflora, particularly acetogenin, alkaloids and flavonoid-rich fractions, was determined in vivo using Plasmodium berghei-infected mice model and toxicity was accessed by brine shrimp assay. The A. crassiflora fractions were administered at doses of 12.5 mg/kg/day in a 4-day test protocol. The results showed that some fractions from woods were rich in acetogenins, alkaloids and terpenes, and other fractions from leaves were rich in alkaloids and flavonoids. The parasitaemia was significantly (p < 0.05, p < 0.001) reduced (57-75%) with flavonoid and alkaloid-rich leaf fractions, which also increased mean survival time of mice after treatment. Our results confirm the usage of this plant in folk medicine as an antimalarial remedy. PMID:24678811

Pimenta, Lúcia Pinheiro Santos; Garcia, Giani Martins; Gonçalves, Samuel Geraldo do Vale; Dionísio, Bárbara Lana; Braga, Erika Martins; Mosqueira, Vanessa Carla Furtado

2014-01-01

454

Reconstitution of a 10-gene pathway for synthesis of the plant alkaloid dihydrosanguinarine in Saccharomyces cerevisiae.  

PubMed

Benzylisoquinoline alkaloids (BIAs) represent a large class of plant secondary metabolites, including pharmaceuticals such as morphine, codeine and their derivatives. Large-scale production of BIA-based pharmaceuticals is limited to extraction and derivatization of alkaloids that accumulate in planta. Synthesis of BIAs in microbial hosts could bypass such limitations and transform both industrial production of BIAs with recognized value and research into uncharacterized BIAs. Here we reconstitute a 10-gene plant pathway in Saccharomyces cerevisiae that allows for the production of dihydrosanguinarine and its oxidized derivative sanguinarine from (R,S)-norlaudanosoline. Synthesis of dihydrosanguinarine also yields the side-products N-methylscoulerine and N-methylcheilanthifoline, the latter of which has not been detected in plants. This work represents the longest reconstituted alkaloid pathway ever assembled in yeast and demonstrates the feasibility of the production of high-value alkaloids in microbial systems. PMID:24513861

Fossati, Elena; Ekins, Andrew; Narcross, Lauren; Zhu, Yun; Falgueyret, Jean-Pierre; Beaudoin, Guillaume A W; Facchini, Peter J; Martin, Vincent J J

2014-01-01

455

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

456

In vitro screening for antiplasmodial activity of isoquinoline alkaloids from Brazilian plant species.  

PubMed

In the search for new antimalarial agents, nine Brazilian plant species were selected, from the Annonaceae (6), Menispermaceae (2) and Siparunaceae (1) families naturally occurring at the cerrado and Atlantic rainforest regions, in order to investigate their in vitro antiplasmodial activity. The ethanol and the alkaloid extracts were tested against K1, chloroquine-resistant, and Palo Alto, chloroquine-sensitive, strains of Plasmodium falciparum. The majority of the alkaloid extracts were more active than the ethanol ones, with IC(50) ranging 0.3-8.2 microg/mL. The crude Guatteria australis alkaloids were the most active against K1 with an IC(50) = 0.3 microg/mL. The most promising total alkaloid fractions for further bioguided isolation are those with the IC(50) < or = 5 microg/mL: G. australis, Cissampelos ovalifolia and Duguetia lanceolata. PMID:15533296

Fischer, Dominique Corinne Hermine; de Amorim Gualda, Nilton Carlos; Bachiega, Danielle; Carvalho, Cyntia Salerno; Lupo, Fernanda Nogueira; Bonotto, Sonia Valéria; Alves, Mariana de Oliveira; Yogi, Alvaro; Santi, Silvia Maria Di; Avila, Priscilla Elisangela; Kirchgatter, Karin; Moreno, Paulo Roberto Hrihorowitsch

2004-01-01

457

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...

Krejsa, Beverly Blohowiak

1981-01-01

458

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

459

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

460

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

461

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

462

Applications of 1 H and 13 C NMR spectroscopy in structural investigations of Vinca indole alkaloids  

Microsoft Academic Search

This review considers the laws connecting the parameters of the1H and13C NMR spectra with the structure of the substances and the use of these laws for solving structural and stereochemical problems of theVinca indole alkaloids and other compounds of closely related structure. For each type of alkaloids, characteristic features of the PMR and13C NMR spectra are given that permit the

M. R. Yagudaev

1986-01-01

463

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

464

Alkaloid Production in Tissue Cultures of Papaver somniferum L. cv. Office-95  

E-print Network

The capacity of alkaloid synthesis was examined in embryogenic callus tissues of Turkish opium poppy, Papaver somniferum L cv. office-95. Eight months old cultures grown in hormone-free MS were examined for alkaloid content. They were found to produce codeine at a level of 1.2 × 10-2, the baine 2.5 × 10-3, noscapine 2.2 × 10-3, morphine 1.6 × 10-3 and papaverine 5.2 × 10-4 % FW.

Esin Akçam Oluk

465

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

466

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

467

Concise Total Syntheses of the Lycopodium Alkaloids (±)-Nankakurines A and B via Luciduline  

PubMed Central

Total syntheses of the Lycopodium alkaloids nankakurines A and B have been accomplished in 6 and 7 steps, respectively, via a sequence that passes through a third Lycopodium alkaloid, luciduline, and forgoes the use of protecting groups on nitrogen. Key features include a short preparation of luciduline followed by a concise and stereoselective aminoallylation/ring-closing metathesis protocol to fashion the spiropiperidine ring common to nankakurines A and B. PMID:20014779

Cheng, Xiayun; Waters, Stephen P.

2009-01-01

468

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

469

Indole alkaloids from cell suspension cultures of Tabernaemontana divaricata and Tabernanthe iboga.  

PubMed

From cell suspension cultures of Tabernaemontana divaricata and Tabernanthe iboga grown under standard conditions, six monoterpenoid indole alkaloids have been isolated and identified. T. divaricata synthesized apparicine, catharanthine, coronaridine, conoflorine, tubotaiwine and vinervine, whereas T. iboga produced tubotaiwine and conoflorine. Both cultures are a reasonable source for conoflorine, which is expected to be a good candidate for studying the mechanism of Aspidosperma type alkaloid formation at the cell-free level. PMID:24257961

Pawelka, K H; Stöckigt, J

1983-04-01

470

A PIP-family protein is required for biosynthesis of tobacco alkaloids  

Microsoft Academic Search

Plants in the Nicotiana genus produce nicotine and related pyridine alkaloids as a part of their chemical defense against insect herbivores. These\\u000a alkaloids are formed by condensation of a derivative of nicotinic acid, but the enzyme(s) involved in the final condensation\\u000a step remains elusive. In Nicotiana tabacum, an orphan reductase A622 and its close homolog A622L are coordinately expressed in

Masataka Kajikawa; Nobuhiro Hirai; Takashi Hashimoto

2009-01-01

471

Antisense RNA-Mediated Suppression of Benzophenanthridine Alkaloid Biosynthesis in Transgenic Cell Cultures of California Poppy  

Microsoft Academic Search

California poppy (Eschscholzia californica Cham.) cell cultures produce several benzophenanthridine alkaloids, such as sanguinarine, chelirubine, and macarpine, with potent pharmacological activity. Antisense constructs of genes encoding two enzymes involved in benzophenanthridine alkaloid biosynthesis, the berberine bridge enzyme (BBE) and N-methylcoclaurine 3-hydroxylase (CYP80B1), were introduced separately into California poppy cell cultures. Transformed cell lines expressing antisense BBE or antisense CYP80B1 constructs

Sang-Un Park; Min Yu; Peter J. Facchini

2002-01-01

472

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

Microsoft Academic Search

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

Kirsten Borstel; Thomas Hartmann

1986-01-01

473

Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from the Icelandic Lycopodium annotinum ssp. alpestre  

Microsoft Academic Search

The aim of this study was to investigate structures and acetylcholinesterase inhibitory activities of lycopodane-type alkaloids isolated from an Icelandic collection of Lycopodium annotinum ssp. alpestre. Ten alkaloids were isolated, including annotinine, annotine, lycodoline, lycoposerramine M, anhydrolycodoline, gnidioidine, lycofoline, lannotinidine D, and acrifoline, as well as a previously unknown N-oxide of annotine. 1H and 13C NMR data of several of

Elsa Steinunn Halldorsdottir; Jerzy W. Jaroszewski; Elin Soffia Olafsdottir

2010-01-01

474

Geissoschizine methyl ether N-oxide, a new alkaloid with antiacetylcholinesterase activity from Uncaria rhynchophylla.  

PubMed

Geissoschizine methyl ether N-oxide, a new oxindole alkaloid, along with 14 known alkaloids, was isolated from the aerial part of Uncaria rhynchophylla. Their structures were identified by comprehensive spectral methods, including 2D NMR experiments, and confirmed by comparing with the literature data. In vitro acetylcholinesterase (AChE) inhibitory activity assay showed that the new compound exhibited anti-AChE activity with IC50 value of 23.4 ?M. PMID:25496282

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

2015-05-01

475

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

476

A novel quinoline alkaloid possessing a 7-benzyl group from the centipede, Scolopendra subspinipes.  

PubMed

The novel quinoline alkaloid scolopendrine was isolated from the centipede, Scolopendra subspinipes mutilans L. Koch. The structure was determined to be 2-hydroxy-7-[(4-hydroxy-3-methoxyphenyl)methyl]-3-methoxy-8-quinolyl sulfate on the basis of high-resolution electron-spray ionization mass spectroscopy and two-dimensional NMR spectral data. Unlike quinoline alkaloids so far reported, scolopendrine is unique in having a 7-benzyl moiety in the quinoline ring. PMID:11456108

Noda, N; Yashiki, Y; Nakatani, T; Miyahara, K; Du, X M

2001-07-01

477

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

478

Chemical Composition and Pharmacological Activity of Alkaloids from the Common Periwinkle Cultured in Georgia  

Microsoft Academic Search

periwinkle to the field of the Experimental Center of Medicinal Plants (Shiraki, East Kakhetia) was successful, leading to an increase in the alkaloid content. The total alkaloid yield reached up to 1 and 0.8%, in which the vincamine content amounted to 0.06 and 0.04%, in the blooming and fruitage stages, respectively. The purpose of this study was to refine the

V. Yu. Vachnadze; É. Z. Dzhakeli; Z. V. Robakidze; G. V. Chkhikvadze; M. M. Mudzhiri; G. V. Abuladze; N. A. Chuchulashvili

2001-01-01

479

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

480

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

481

Rapid construction of the ABC ring system in the Daphniphyllum alkaloid daphniyunnine C.  

PubMed

An efficient and scalable synthesis of the ABC ring system common to the calyciphylline A-type alkaloids has been developed. The tricyclic core of the alkaloids features a bowl-shaped [6-6-5] skeleton with five stereogenic centers including an all-carbon quaternary center. It was constructed rapidly from a readily available carvone derivative through a seven-step sequence involving an aza-Michael addition and Pd-catalyzed enolate ?-vinylation as key steps. PMID:23095081

Yao, Yanmin; Liang, Guangxin

2012-11-01

482

Potential of gamma radiation enhancing the biosynthesis of tropane alkaloids in black henbane (Hyoscyamus niger L.)  

Microsoft Academic Search

A productive yellow flowered mutant with high tropane alkaloid content was isolated in the M2 generation of gamma irradiated (Co60 at 40 kr) progenies ofHyoscyamus niger. Mutant progenies, on an average, were capable of synthetising more than twice crude alkaloid (0.147% to 0.221%) in M3 through M6 generations compared to the parental control (0.065 to 0.106%). In pilot scale trial

J. R. Sharma; R. K. Lal; H. O. Misra; M. M. Gupta; R. S. Ram

1989-01-01

483

Induction of pyridine alkaloid formation in transformed root cultures of Nicotiana tabacum.  

PubMed

Hairy root cultures of Nicotiana tabacum were set up by excised root tips with Agrobacterium rhizogenes. The successful transformation was confirmed by analyzing rolC and virC genes using polymerase chain reaction (PCR). Hairy root cultures were employed to study the formation of pyridine alkaloids, mainly nicotine. The transformed cultures were incubated with potential elicitors, such as methyljasmonate, quercetin and salicylic acid, in order to stimulate the biosynthesis of pyridine alkaloids. Profile and amounts of pyridine alkaloids were analyzed using capillary GLC-MS. Treatment of the cultures with methyljasmonate (50 microM) increased the alkaloid accumulation ca. 7-fold up to a level of 0.58 mg/g fresh weight as compared to untreated controls. Quercetin (200 microM) enhanced the alkaloid production ca. 4-fold (0.34 mg/g fresh weight) within 24 h. In contrast salicylic acid in all tested concentrations decreased the alkaloid level to 1 microg/g fresh weight. Also the inhibitory effect of salicylic acid on the elicitation effect of methyljasmonate and quercetin was investigated. PMID:20158160

Zayed, Rawia; Wink, Michael

2009-01-01

484

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

485

Acetylcholinesterase inhibitory activity of lycopodane-type alkaloids from the Icelandic Lycopodium annotinum ssp. alpestre.  

PubMed

The aim of this study was to investigate structures and acetylcholinesterase inhibitory activities of lycopodane-type alkaloids isolated from an Icelandic collection of Lycopodium annotinum ssp. alpestre. Ten alkaloids were isolated, including annotinine, annotine, lycodoline, lycoposerramine M, anhydrolycodoline, gnidioidine, lycofoline, lannotinidine D, and acrifoline, as well as a previously unknown N-oxide of annotine. 1H and 13C NMR data of several of the alkaloids were provided for the first time. Solvent-dependent equilibrium constants between ketone and hemiketal form of acrifoline were determined. Conformation of acrifoline was characterized using NOESY spectroscopy and molecular modelling. The isolated alkaloids were evaluated for their in vitro inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Ligand docking studies based on mutated 3D structure of Torpedo californica acetylcholinesterase provided rationale for low inhibitory activity of the isolated alkaloids as compared to huperzine A or B, which are potent acetylcholinesterase inhibitors belonging to the lycodine class. Based on the modelling studies the lycopodane-type alkaloids seem to fit well into the active site gorge of the enzyme but the position of their functional groups is not compatible with establishing strong hydrogen bonding interactions with the amino acid residues that line the binding site. The docking studies indicate possibilities of additional functionalization of the lycopodane skeleton to render potentially more active analogues. PMID:19939421

Halldorsdottir, Elsa Steinunn; Jaroszewski, Jerzy W; Olafsdottir, Elin Soffia

2010-02-01

486

Variation in the expression of ergot alkaloids between individual tillers of perennial ryegrass  

NASA Astrophysics Data System (ADS)

Epichloë fungal endophytes of cool season grasses are well known to produce a range of alkaloids of benefit to the host. Some of these compounds are advantageous to agriculture due to qualities that promote pasture persistence (e.g. the loline class of alkaloids confer insect protection) while others are detrimental to the wellbeing of grazing livestock. The ergot alkaloids (e.g. ergovaline), produced in ryegrass and tall fescue associations, causes poor animal health in farming regions in many countries around the world and further study is required to improve our knowledge on this class of compounds. Here we present the application of a quantitative LC-MS/MS (liquid chromatography coupled to mass spectrometry) method measuring eight ergot alkaloids (chanoclavine, agroclavine, elymoclavine, lysergol, lysergic acid, ergine, lysergyl alanine, ergovaline) produced by endophyte infected grasses, to monitor levels in individual tillers from multiple plants of a single cultivar of perennial ryegrass (Lolium perenne cv. ‘Grasslands Samson’) infected with a common toxic endophyte strain (Epichloë festucae var. lolii). Monitoring the expression in individual tillers allows an estimation of the variability within a plant (between tillers) as well as between plants. The study showed that there is significant variation in the concentration of the ergot alkaloids between tillers of a single plant, at or exceeding the level of variation observed between individual plants of a population. This result emphasizes the fundamental importance of robust experimental design and sampling procedures when alkaloid expression assessment is required and these need to be rigorously tailored to the hypothesis being tested.

Mace, Wade; Lunn, Kristy; Lloyd-West, Catherine

2014-11-01

487

Currencies of Mutualisms: Sources of Alkaloid Genes in Vertically Transmitted Epichloae  

PubMed Central

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

2013-01-01

488

Comparative analysis of Papaver somniferum genotypes having contrasting latex and alkaloid profiles.  

PubMed

Papaver somniferum produces therapeutically useful benzylisoquinoline alkaloids (BIAs) like papaverine, thebaine, codeine, and morphine that accumulate in its capsular latex. Morphine is a potent analgesic but is also abused as a narcotic, which has increased the demand for non-narcotic thebaine that can be converted into various analgesics. To curtail the narcotic menace, many distinct genotypes of the plant have been developed that are deficient in morphine and/or latex. Sujata is one such latex-less low alkaloid-producing variety developed from the alkaloid-rich gum harvest variety Sampada. Its utility for gene prospecting and studying differential gene regulation responsible for its low alkaloid, nutritive seed oil, and latex-less phenotype has been exploited in this study. BIA profiling of Sujata and Sampada capsules at the early and late stages indicated that except for thebaine, Sujata had a depressed alkaloid phenotype as compared to Sampada. Comparative transcript-based analysis of the two genotypes was carried out in the early stage capsule (higher thebaine) using subtractive hybridization and microarray. Interrogation of a P. somniferum array yielded many differentially expressing transcripts. Their homology-based annotation classified them into categories--latex related, oil/lipid related, alkaloid related, cell wall related, and others. These leads will be useful to characterize the highly sought after Sujata phenotype. PMID:24306419

Chaturvedi, Nidarshana; Singh, Mridula; Shukla, Ashutosh K; Shasany, Ajit K; Shanker, Karuna; Lal, Raj K; Khanuja, Suman P S

2014-07-01

489

Leaf alkaloid contents of Tabernaemontana pachysiphon as influenced by endogenous and environmental factors in the natural habitat.  

PubMed

Indole alkaloid contents were investigated in leaves of Tabernaemontana pachysiphon (Apocynaceae) trees in the natural habitat, Shimba Hills National Reserve, Kenya. The contents of the major alkaloids apparicine, tubotaiwine, tubotaiwine- N-oxide, and isovoacangine varied with site, leaf age, leaf growth form, position in the crown, and plant age. Alkaloid contents were highest in young leaves. Trees bearing aberrant small dwarf-leaves showed similar alkaloid patterns as young leaves from healthy trees. At single trees, the contents were found to increase from the top to the bottom of the crown. Tree age had little influence on leaf alkaloid contents. In even aged leaves of trees from different forest sites, alkaloid contents were highest at the site with highest soil cation exchange capacity (CEC) and base saturation. PMID:17253230

Höft, M; Verpoorte, R; Beck, E

1998-03-01

490

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

491

Manipulating indole alkaloid production by Catharanthus roseus cell cultures in bioreactors: from biochemical processing to metabolic engineering  

Microsoft Academic Search

Catharanthus roseus plants produce many pharmaceutically important indole alkaloids, of which the bisindole alkaloids vinblastine and vincristine\\u000a are antineoplastic medicines and the monoindole alkaloids ajmalicine and serpentine are antihypertension drugs. C. roseus cell cultures have been studied for producing these medicines or precursors catharanthine and vindoline for almost four decades\\u000a but so far without a commercially successful process due to

Jian Zhao; Robert Verpoorte

2007-01-01

492

Quantitative 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy.  

PubMed

Opium poppy (Papaver somniferum) produces a diverse array of bioactive benzylisoquinoline alkaloids and has emerged as a versatile model system to study plant alkaloid metabolism. The plant is widely cultivated as the only commercial source of the narcotic analgesics morphine and codeine. Variations in plant secondary metabolism as a result of genetic diversity are often associated with perturbations in other metabolic pathways. As part of a functional genomics platform, we used (1)H nuclear magnetic resonance (NMR) metabolite profiling for the analysis of primary and secondary metabolism in opium poppy. Aqueous and chloroform extracts of six different opium poppy cultivars were subjected to chemometric analysis. Principle component analysis of the (1)H NMR spectra for latex extracts clearly distinguished two varieties, including a low-alkaloid variety and a high-thebaine, low-morphine cultivar. Distinction was also made between pharmaceutical-grade opium poppy cultivars and a condiment variety. Such phenotypic differences were not observed in root extracts. Loading plots confirmed that morphinan alkaloids contributed predominantly to the variance in latex extracts. Quantification of 34 root and 21 latex metabolites, performed using Chenomx NMR Suite version 4.6, showed major differences in the accumulation of specific alkaloids in the latex of the low-alkaloid and high-thebaine, low-morphine varieties. Relatively few differences were found in the levels of other metabolites, indicating that the variation was specific for alkaloid metabolism. Exceptions in the low-alkaloid cultivar included an increased accumulation of the alkaloid precursor tyramine and reduced levels of sucrose, some amino acids, and malate. Real-time polymerase chain reaction analysis of 42 genes involved in primary and secondary metabolism showed differential gene expression mainly associated with alkaloid biosynthesis. Reduced alkaloid levels in the condiment variety were associated with the reduced abundance of transcripts encoding several alkaloid biosynthetic enzymes. PMID:18550684

Hagel, Jillian M; Weljie, Aalim M; Vogel, Hans J; Facchini, Peter J

2008-08-01

493

Hindi Numerals.  

ERIC Educational Resources Information Center

In most languages encountered by linguists, the numerals, considered as a paradigmatic set, constitute a morpho-syntactic problem of only moderate complexity. The Indo-Aryan language family of North India, however, presents a curious contrast. The relatively regular numeral system of Sanskrit, as it has developed historically into the modern…

Bright, William

494

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

495

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

496

Heterologous Expression of Lysergic Acid and Novel Ergot Alkaloids in Aspergillus fumigatus  

PubMed Central

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.

2014-01-01

497

Identification and Quantification of the Main Active Anticancer Alkaloids from the Root of Glaucium flavum  

PubMed Central

Glaucium flavum is used in Algerian folk medicine to remove warts (benign tumors). Its local appellations are Cheqiq el-asfar and Qarn el-djedyane. We have recently reported the anti-tumoral activity of Glaucium flavum root alkaloid extract against human cancer cells, in vitro and in vivo. The principal identified alkaloid in the extract was protopine. This study aims to determine which component(s) of Glaucium flavum root extract might possess potent antitumor activity on human cancer cells. Quantitative estimation of Glaucium flavum alkaloids was realized by HPLC-DAD. Glaucium flavum effect on human normal and cancer cell viability was determined using WST-1 assay. Quantification of alkaloids in Glaucium flavum revealed that the dried root part contained 0.84% of protopine and 0.07% of bocconoline (w/w), while the dried aerial part contained only 0.08% of protopine, glaucine as the main alkaloid, and no bocconoline. In vitro evaluation of the growth inhibitory activity on breast cancer and normal cells demonstrated that purified protopine did not reproduce the full cytotoxic activity of the alkaloid root extract on cancer cell lines. On the other hand, bocconoline inhibited strongly the viability of cancer cells with an IC50 of 7.8 ?M and only a low cytotoxic effect was observed against normal human cells. Our results showed for the first time that protopine is the major root alkaloid of Glaucium flavum. Finally, we are the first to demonstrate a specific anticancer effect of Glaucium flavum root extract against breast cancer cells, which can be attributed, at least in part, to bocconoline. PMID:24317429

Bournine, Lamine; Bensalem, Sihem; Wauters, Jean-Noël; Iguer-Ouada, Mokrane; Maiza-Benabdesselam, Fadila; Bedjou, Fatiha; Castronovo, Vincent; Bellahcène, Akeila; Tits, Monique; Frédérich, Michel

2013-01-01

498

Differences in Tolerance to Host Cactus Alkaloids in Drosophila koepferae and D. buzzatii  

PubMed Central

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

499

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

500

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