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1

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

PubMed

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

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

1998-09-01

2

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

Microsoft Academic Search

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

Michelle D. Marko; Frank R. Stermitz

1997-01-01

3

Three new toxic norditerpenoid alkaloids from the low larkspur Delphinium nuttallianum.  

PubMed

Three new N-(methylsuccinimido)anthranoyllycoctonine norditerpenoids, given the names bearline (1), 14-acetylbearline (2), and 16-deacetylgeyerline (3), were isolated from the extract of the low larkspur Delphinium nuttallianum. The structures of the individual alkaloids were determined by (1)H and (13)C NMR spectroscopy and HRMS. These alkaloids are structurally related to the neurotoxic alkaloid methyllycaconitine (4) and may be important in establishing the toxicity of low larkspurs to cattle. A mouse bioassay was used to measure the LD(50) values for two of the new alkaloids (1 and 2), as sufficient quantities of 3 were not available for toxicity testing. A structurally related alkaloid, geyerline (7), was isolated from D. geyeri in sufficient quantities for toxicity testing. The toxicities of 1, 2, and 7 were found to be comparable to that of 4, with calculated LD(50) values in mice of 5.7, 3.3, and 6.2 mg/kg, respectively. PMID:10978210

Gardner, D R; Manners, G D; Panter, K E; Lee, S T; Pfister, J A

2000-08-01

4

A toxicokinetic comparison of norditerpenoid alkaloids from Delphinium barbeyi and D. glaucescens in cattle.  

PubMed

Cattle are poisoned by N-(methylsuccinimido) anthranoyllycoctonine type (MSAL-type) and 7,8-methylenedioxylycoctonine type (MDL-type) norditerpenoid alkaloids in Delphinium spp. Alkaloids in D. glaucescens are primarily of the MSAL-type, while D. barbeyi is a mixture of MSAL and MDL-types. The objectives of this study were to determine and compare the toxicokinetics of selected alkaloids from D. glaucescens and D. barbeyi in cattle. The two species of larkspur were dosed to three groups of Angus steers via oral gavage at doses of 8?mg?kg?¹ MSAL-type alkaloids for D. barbeyi and either 8.0 or 17.0?mg?kg?¹ MSAL-type alkaloids for D. glaucescens. In cattle dosed with D. barbeyi, serum deltaline (MDL-type) concentrations peaked at 488 ± 272?ng?ml?¹ at 3?h and serum methyllycaconitine (MSAL-type) concentrations peaked at 831 ± 369?ng?ml?¹ at 6?h. Deltaline was not detected in the serum of cattle dosed with D. glaucescens. Serum methyllycaconitine concentrations peaked at 497 ± 164?ng?ml?¹ at 18?h, and 1089 ± 649?ng?ml?¹ at 24?h for the 8?mg?kg?¹ and 17?mg?kg?¹ doses of D. glaucescens respectively. There were significant differences between the maximum serum concentrations and the area under the curve for the two doses of D. glaucescens but not D. barbeyi. Results from this experiment support the recommendation that approximately 7 days are required to clear 99% of the toxic alkaloids from the serum of animals orally dosed with D. barbeyi or D. glaucescens, and that MDL-type alkaloids play an important role in the toxicity of Delphinium spp. in cattle. PMID:20635330

Green, Benedict T; Welch, Kevin D; Gardner, Dale R; Stegelmeier, Bryan L; Pfister, James A; Cook, Daniel; Davis, T Zane

2011-01-01

5

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

PubMed

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

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

1999-12-01

6

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.; Nordstr?m, Lars Ulrik; Tan, Derek S.; Gin, David Y.

2013-01-01

7

Influence of Light and Photosynthesis on Alkaloid Concentration in Larkspur  

Microsoft Academic Search

Concentrations of toxic norditerpenoid alkaloids vary greatly in tall larkspur (Delphinium barbeyi) and may be influenced by environmental stress. We evaluated the effect of shade, darkness, and inhibition of photosynthesis on toxic alkaloid concentration. In plants treated with metribuzin to inhibit photosynthesis, alkaloid concentration increased, but dry weight of the plants decreased as growth ceased, leaving absolute alkaloid content similar

M. H. Ralphs; G. D. Manners; D. R. Gardner

1998-01-01

8

Vinca alkaloids.  

PubMed

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

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

2013-11-01

9

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

10

Indolizidine and quinolizidine alkaloids.  

PubMed

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including ants, amphibians and beetles; indolizidine alkaloids from the genera Polygonatum, Prosopis and Elaeocarpus; indolizidine and phenanthroindolizidine alkaloids; alkylquinolizidine alkaloids, including myrtine, epimyrtine, plumerinine and Lycopodium metabolites; Lythraceae and Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 150 references are cited. PMID:17268613

Michael, Joseph P

2007-02-01

11

Indolizidine and quinolizidine alkaloids.  

PubMed

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including arthropods and amphibians; alkaloids from the genera Polygonatum, Prosopis and Poranthera; phenanthroindolizidine and phenanthroquinolizidine alkaloids; Nuphar alkaloids; lupine alkaloids; and alkaloids from marine sources. 130 references are cited. PMID:18250900

Michael, Joseph P

2008-02-01

12

Pyrrolizidine alkaloids.  

PubMed

Covering: July 2001 to December 2012This 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

13

Indolizidine and quinolizidine alkaloids.  

PubMed

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from animal sources, including ants, amphibians and beetles; ipalbidine, phenanthroindolizidines and related alkaloids; Lycopodium alkaloids; lupine alkaloids; and alkaloids from bacterial and marine sources. The literature from July 2002 to June 2003 is reviewed, and 174 references are cited. PMID:15459758

Michael, Joseph P

2004-10-01

14

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

15

In vitro ruminal metabolism of larkspur alkaloids.  

PubMed

Larkspur (Delphinium sp) poisoning of range cattle is a serious, recurring problem in the western United States. Numerous stratagems have been recommended to ameliorate larkspur intoxication, but none are completely effective. Previous studies in this laboratory indicated bovine ruminal microflora are capable of chemically modifying Delphinium alkaloids. Research reported herein was undertaken to further evaluate whether differences in ovine and bovine rumen metabolism might explain differences in susceptibility to larkspur intoxication and whether existing metabolic activity can be enhanced by sustained exposure to Delphinium alkaloids. Comparison of ovine and bovine rumen metabolism of Delphinium geyeri alkaloids in vitro failed to demonstrate differences in the rate of alkaloid metabolism. Rumen liquor collected sequentially from a fistulated cow dosed with dried Delphinium geyeri did not vary in ability to metabolize larkspur alkaloids. PMID:1609485

Siemion, R S; Raisbeck, M F; Waggoner, J W; Tidwell, M A; Sanchez, D A

1992-06-01

16

Indolizidine and quinolizidine alkaloids.  

PubMed

This review covers the isolation, structure determination, synthesis, chemical transformations and biological activity of indolizidine and quinolizidine alkaloids from microbial, plant and animal sources. Included in the review are slaframine; the hydroxylated indolizidines lentiginosine, swainsonine, castanospermine and their analogues; alkaloids from amphibians and marine sources; plumerinine; ipalbidine, phenanthroindolizidines and related alkaloids; lasubine-II: and lupin alkaloids. The literature from July 2001 to June 2002 is reviewed, and 142 references are cited. PMID:14620842

Michael, Joseph P

2003-10-01

17

A New Strychnos Alkaloid  

Microsoft Academic Search

As part of a survey of the chemical constituents of the Australian flora, we have examined the alkaloids of Strychnos psilosperma F. Muell. Leaves collected at Dalmar, near Rockhampton, contained approximately 1 per cent total alkaloid from which a new alkaloid, now named `strychnospermine', was readily isolated. It formed colourless needles of melting point 209°, had [alpha]D + 58° (c

F. A. L. Anet; G. K. Hughes; E. Ritchie

1950-01-01

18

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

19

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

20

Alkaloids of Glaucium corniculatum  

Microsoft Academic Search

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

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

1983-01-01

21

Alkaloids of Ocotea brachybotra.  

PubMed

Aporphine, proaporphine and morphinane alkaloids were isolated from the leaves of a Brazilian Lauracea, Ocotea brachybotra (Meiss.) Mez. The known alkaloids were identified through their physico-chemical properties as: (I) (+/-)-glaziovine, (II) dicentrine, (III) ocopodine, (IV) cassynthicine, (V) predicentrine, (VI) leucoxine, (IX) sinacutine and (X) pallidine. The structure of (VI) leucoxine was confirmed by a detailed analysis of the N.M.R. spectra recorded in various conditions. New morphinane alkaloids, (XI) ocobotrine and (XII) 14-espisinomenine, having the unusual B/C-trans configuration were also isolated. Their structures were determined using spectroscopic methods and chemical correlations. PMID:923790

Vecchietti, V; Casagrande, C; Ferrari, G

1977-11-01

22

Synthesizing an Alkaloid  

NSDL National Science Digital Library

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

Foundation, Wgbh E.

2007-02-12

23

Occurrence of halogenated alkaloids.  

PubMed

Once considered to be isolation artifacts or chemical "mistakes" of nature, the number of naturally occurring organohalogen compounds has grown from a dozen in 1954 to >5000 today. Of these, at least 25% are halogenated alkaloids. This is not surprising since nitrogen-containing pyrroles, indoles, carbolines, tryptamines, tyrosines, and tyramines are excellent platforms for biohalogenation, particularly in the marine environment where both chloride and bromide are plentiful for biooxidation and subsequent incorporation into these electron-rich substrates. This review presents the occurrence of all halogenated alkaloids, with the exception of marine bromotyrosines where coverage begins where it left off in volume 61 of The Alkaloids. Whereas the biological activity of these extraordinary compounds is briefly cited for some examples, a future volume of The Alkaloids will present full coverage of this topic and will also include selected syntheses of halogenated alkaloids. Natural organohalogens of all types, especially marine and terrestrial halogenated alkaloids, comprise a rapidly expanding class of natural products, in many cases expressing powerful biological activity. This enormous proliferation has several origins: (1) a revitalization of natural product research in a search for new drugs, (2) improved compound characterization methods (multidimensional NMR, high-resolution mass spectrometry), (3) specific enzyme-based and other biological assays, (4) sophisticated collection methods (SCUBA and remote submersibles for deep ocean marine collections), (5) new separation and purification techniques (HPLC and countercurrent separation), (6) a greater appreciation of traditional folk medicine and ethobotany, and (7) marine bacteria and fungi as novel sources of natural products. Halogenated alkaloids are truly omnipresent in the environment. Indeed, one compound, Q1 (234), is ubiquitous in the marine food web and is found in the Inuit from their diet of whale blubber. Given the fact that of the 500,000 estimated marine organisms--which are the source of most halogenated alkaloids--only a small percentage have been investigated for their chemical content, it is certain that myriad new halogenated alkaloids are awaiting discovery. For example, it is estimated that nearly 4000 species of bryozoans have not been examined for their chemical content. The few species that have been studied contain some extraordinary halogenated alkaloids, such as hinckdentine A (610) and the chartellines (611-613). Of the estimated 1.5 million species of fungi, secondary metabolites have been characterized from only 5000 species. The future seems bright for the collector of halogenated alkaloids! PMID:23189746

Gribble, Gordon W

2012-01-01

24

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

25

Pyrrolizidine alkaloids from Senecio nevadensis.  

PubMed

Two toxic pyrrolizidine alkaloids were isolated from Senecio nevadensis and their structures determined by spectroscopic methods. For the first time, a very complete structural assignment of all spectral data of alkaloid usaramine is given. PMID:9689604

Bourauel, T; Plassmeier, C; Roeder, E

1998-02-01

26

Alkaloids from Egyptian Papaver rhoeas.  

PubMed

N-methylasimilobine was isolated as the major alkaloid from an Egyptian sample of P. RHOEAS L. Other alkaloids isolated from the same plant material were stylopine, coptisine, isocorydine and rhoeadine. Chromatography indicated the presence of at least nine other minor alkaloids. PMID:17401817

El-Masry, S; El-Ghazooly, M G; Omar, A A; Khafagy, S M; Phillipson, J D

1981-01-01

27

Pyrrolizidine alkaloids from Cynoglossum furcatum.  

PubMed

Two new pyrrolizidine alkaloids have been isolated from the roots of Cynoglossum furcatum. On the basis of chemical and spectroscopic evidence, structures of the compounds have been elucidated. They are lactodine (3), a monoster alkaloid and viridinatine (4), a pyrrolizidine diester alkaloid. The structure of lactodine is elucidated as 9-O-(-)lactyl heliotridine and viridinatine as 7-O-(-)viridifloryl echinatine. PMID:18348059

Ravi, S; Ravikumar, R; Lakshmanan, A J

2008-01-01

28

Polyhydroxy alkaloids: chromatographic analysis.  

PubMed

Polyhydroxy alkaloids are a burgeoning category of natural products that encompass several structural types and generally exhibit potent activity as inhibitors of glycosidases. As presently defined the group consists of monocyclic or bicyclic aLkaloids of the pyrrolidine, piperidine, pyrrolizidine, indolizidine and tropane classes, bearing two or more hydroxyl groups. These structural features render the compounds highly water soluble and frequently quite insoluble in non-hydroxylic solvents, so that their isolation and analysis by chromatographic means are consequently difficult. This problem is further confounded by the lack of a chromophore which would permit their detection by UV absorption. This review presents chromatographic techniques that have been successfully applied to the problem of isolating, purifying, detecting and analyzing polyhydroxy alkaloids. PMID:12219930

Molyneux, Russell J; Gardner, Dale R; James, Lynn F; Colegate, Steven M

2002-08-16

29

New alkaloids from Pandanus amaryllifolius.  

PubMed

Three new alkaloids, the two pyrrolidine type alkaloids (1 and 2) and 6E-pandanamine (3), together with five known alkaloids (4-8), were isolated from the leaves of Pandanus amaryllifolius collected in West Java, Indonesia. All the new alkaloids have two alpha-methyl alpha,beta-unsaturated gamma-lactone moieties, while compound 2 also has an additional seven-membered ring, which has not been encountered before in Pandanus alkaloids. Two different extraction methods, namely, a solvent partitioning extraction and acid-base treatment, were tested, giving secondary and tertiary amines, respectively. Spectroscopic and chemical studies showed that the tertiary amines isolated from the acid-base treatment were artifacts formed during the extraction process. This finding suggests that the use of conventional acid-base treatment in isolating Pandanus alkaloids should be reviewed since it can introduce artifacts. PMID:14738386

Salim, Angela A; Garson, Mary J; Craik, David J

2004-01-01

30

Quaternary alkaloids of Argemone mexicana.  

PubMed

Four quaternary isoquinoline alkaloids, dehydrocorydalmine, jatrorrhizine, columbamine, and oxyberberine, have been isolated from the whole plant of Argemone mexicana Linn. (Papaveraceae) and their structures established by spectral evidence. This is the first report of these alkaloids (dehydrocorydalmine, jatrorrhizine, columbamine, and oxyberberine) from Argemone mexicana and the Argemone genus. PMID:20645832

Singh, Sarita; Singh, Tryambak Deo; Singh, Virendra Pratap; Pandey, Vidya Bhushan

2010-02-01

31

I. Cyclopeptide alkaloids; II. Phycocyanobilipeptides  

Microsoft Academic Search

Several examples of the 14-membered, para-bridged ring system of the cyclopeptide alkaloids have been synthesized via an active ester cyclization. The yield of monomeric cyclopeptide varied from 1 to 33% and was affected by the amino acid substitution pattern and amide conformation of the linear peptide precursors. Both the synthetic models and a naturally cyclopeptide alkaloid, ceanothine B, bind monovalent

Lagarias

1979-01-01

32

Ergot and Its Alkaloids  

PubMed Central

This manuscript reviews the history and pharmacognosy of ergot, and describes the isolation/preparation, chemistry, pharmacodynamics, and pharmacotherapeutics of the major ergot alkaloids and their derivatives. A brief discussion of the hallucinogenic properties of lysergic acid diethylamide is also featured. An abbreviated form of the material found in this paper is presented in a 4-hour didactic format to third-professional year PharmD students as part of their study of vascular migraine headaches, Parkinson's disease, and naturally occurring hallucinogens/hallucinogen derivatives in the modular course offering Neurology/Psychiatry. PMID:17149427

Schiff, Paul L.

2006-01-01

33

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

...false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119...119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an...

2014-04-01

34

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2013 CFR

...false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119...119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an...

2013-04-01

35

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2011 CFR

...false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119...119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an...

2011-04-01

36

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2010 CFR

...false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119...119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an...

2010-04-01

37

21 CFR 119.1 - Dietary supplements containing ephedrine alkaloids.  

Code of Federal Regulations, 2012 CFR

...false Dietary supplements containing ephedrine alkaloids. 119.1 Section 119...119.1 Dietary supplements containing ephedrine alkaloids. Dietary supplements containing ephedrine alkaloids present an...

2012-04-01

38

Cytotoxic activity of Amaryllidaceae alkaloids.  

PubMed

25 Amaryllidaceae alkaloids belonging to different skeletal types were evaluated for their cytotoxic activity against one murine non-tumoral cell line (LMTK) and two human tumoral cell lines (Molt4 and HepG2) according to established protocols. Significant differences of activity related with the type of skeleton of the tested alkaloids could be observed. Pretazettine (22) was among the most active compound among the 25 tested alkaloids on the Molt4 lymphoid cells, but was inactive against HepG2 hepatoma. On the other hand, lycorenine (11) was found to be the most cytotoxic compound against HepG2 hepatoma, even though it appears to be active against Molt4 cells. Almost all of the tested alkaloids showed cytotoxic activity against fibroblastic LMTK cells. Only mesembrenone (25) showed some specificity against Molt4 cells in comparison to LMTK cells. PMID:7701000

Weniger, B; Italiano, L; Beck, J P; Bastida, J; Bergoñon, S; Codina, C; Lobstein, A; Anton, R

1995-02-01

39

Alkaloids of Rauwolfia species growing in Vietnam  

Microsoft Academic Search

Reserpine, ajmaline, serpentine, ajmalicine, isoreserpiline, and other alkaloids have been isolated from the roots ofRauwolfia cambodiana Pierre ex Pitard,R. verticillata Baill. andR. serpentina Benth.R. vomitoria Afz. was the richest in alkaloids.

Nguen Kim Kan; L. A. Nikolaeva

1991-01-01

40

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

41

Stem bark alkaloids of Rauwolfia vomitoria.  

PubMed

Forty-three indole alkaloids were isolated from 7 kg Rauwolfia vomitoria stem bark; 39 were identified and 2 partially characterised. At least 72 alkaloids classified into 19 types occur in the plant and the interrelationship of the alkaloids and their distribution throughout the plant has been discussed. The major alkaloids of the stems were heteroyohimbines (especially reserpiline) and N (a)-demethyldihydroindoles. PMID:17396795

Iwu, M M; Court, W E

1982-06-01

42

A new benzylisoquinoline alkaloid from Argemone mexicana.  

PubMed

A new benzylisoquinoline alkaloid, argemexirine, together with two known protoberberine alkaloids, dl-tetrahydrocoptisine and dihydrocoptisine, have been isolated from the methanolic extract of the whole plant of Argemone mexicana L. The compounds were identified by spectral and chemical evidence. This is the first report of these alkaloids in this plant species. PMID:20013474

Singh, Sarita; Singh, T D; Singh, V P; Pandey, V B

2010-01-01

43

Diterpenoid Alkaloids as Plant Growth Inhibitors  

Microsoft Academic Search

WE report here preliminary studies on the plant growth inhibitory activity of two diterpenoid alkaloids isolated from the common larkspur, Delphinium ajacis. Little is known about the possible metabolic or physiological action on plants of either terpenoids or alkaloids. The diterpenoid alkaloids are an unusual group of ``secondary metabolites'' produced by plants; they can be derived biogenetically from an isoprenoid

George R. Waller

1969-01-01

44

Alkaloids of some Asian Sedum species  

Microsoft Academic Search

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

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

1996-01-01

45

Biosynthesis of monoterpene indole alkaloids  

E-print Network

the configuration of isovincoside. A cell-free system from Rhazia Stricta 33' 34 wnich is a natural source of 31 strictosidine confirmed the above findings. Thus, strictosidine (3c, ) and not vincoside (38) is the true intermediate in Corynanthe type alkaloid... the configuration of isovincoside. A cell-free system from Rhazia Stricta 33' 34 wnich is a natural source of 31 strictosidine confirmed the above findings. Thus, strictosidine (3c, ) and not vincoside (38) is the true intermediate in Corynanthe type alkaloid...

Ahluwalia, Madhu Ramnarain

2012-06-07

46

Indole Alkaloids from Quassia amara.  

PubMed

Three beta-carboline alkaloids have been isolated for the first time from the wood of QUASSIA AMARA L. (Simarubaceae) and their structures were determined to be 1-vinyl-4,8-dimethoxy-beta-carboline ( 1), 1-methoxycarbonyl-beta-carboline ( 2), and 3-methylcantin-2,6-dione ( 3) by spectral and chemical means. PMID:17269024

Barbetti, P; Grandolini, G; Fardella, G; Chiappini, I

1987-06-01

47

Pyrrolizidine alkaloids from Heliotropium megalanthum.  

PubMed

Two pyrrolizidine alkaloids, megalanthonine (1) and lycopsamine (2), have been isolated from Heliotropium megalanthum. The structure of the novel compound 1 was determined by spectroscopic methods. The insecticidal, antifeedant, and antifungal effects of compounds 1 and 2 have been evaluated. PMID:9834169

Reina, M; Gonzalez-Coloma, A; Gutierrez, C; Cabrera, R; Henriquez, J; Villarroel, L

1998-11-01

48

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

49

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

50

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

51

New aporphine alkaloids of Ocotea minarum.  

PubMed

Fourteen aporphine alkaloids were isolated from the leaves of a Brazilian Lauracea, Ocotea minarum Nees (Mez). The known alkaloids were identified through their physico-chemical properties as: leucoxylonine (VII), dicentrine (IV), ocoteine (V), leucoxine (VI), ocopodine (VIII), predicentrine (IX), dicentrinone (XIV) and thalicminine (XV). Six new aporphine alkaloids were also isolated: ocotominarine (I), ocominarine (III), nor-leucoxylonine (XI), iso-oconovine (xii), 4-hydroxydicentrine (XIII) and ocominarone (XVI). Their structures were determined using spectroscopic methods and chemical correlations. PMID:510527

Vecchietti, V; Casagrande, C; Ferrari, G; Severini Ricca, G

1979-10-01

52

Guanidine alkaloids from Plumbago zeylanica.  

PubMed

Eleven new guanidine alkaloids, plumbagines A-G (2-8) and plumbagosides A-D (9-12), as well as two known analogues (1, 13), were isolated from the aerial parts of Plumbago zeylanica. Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR, MS, IR, and CD methods. The absolute configuration of 1 was determined by single-crystal X-ray diffraction of its derivative (1a). PMID:23848163

Cong, Hai-Jian; Zhang, Shu-Wei; Shen, Yu; Zheng, Yong; Huang, Yu-Jie; Wang, Wen-Qiong; Leng, Ying; Xuan, Li-Jiang

2013-07-26

53

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

54

Cytotoxic aporphine alkaloids from Ocotea acutifolia.  

PubMed

Two new aporphinoid alkaloids, (+)-6 S-ocoteine N-oxide and (+)-norocoxylonine, were isolated from the leaves and trunk bark of OCOTEA ACUTIFOLIA (Lauraceae) along with thirteen aporphine analogues, one morphinan alkaloid, and one flavonoid. The aporphine alkaloids (+)-thalicsimidine and (+)-neolitsine are reported for the first time for the genus OCOTEA. The structures of all compounds were established on the basis of 1D- and 2D-NMR spectroscopic techniques, optical rotation and/or mass spectrometry data. The cytotoxic potential of eight of the aporphine alkaloids against four human cancer cell lines (Hep-2, MCF-7, B16-F10 and 786-0) was also evaluated. PMID:20922653

Garcez, Fernanda R; Francisca da Silva, Ana G; Garcez, Walmir S; Linck, Gabriela; de Fatima Matos, Maria C; Santos, Evelyn C S; Queiroz, Lyara M M

2011-03-01

55

Separation of three ephedra alkaloids using GC-MS.  

E-print Network

??Ephedra, a plant extract, is known to contain six alkaloids – ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, methylephedrine, and methylpseudoephedrine. Of these six alkaloids, ephedrine and pseudoephedrine are… (more)

Tokarz, Kira Bailey

2011-01-01

56

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

57

Ergot alkaloid transport across ruminant gastric tissues  

Microsoft Academic Search

Ergot alkaloids cause fescue toxicosis when livestock graze endophyte-infected tall fescue. It is generally accepted that ergovaline is the toxic compo- nent 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

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

58

Microbial production of plant benzylisoquinoline alkaloids.  

PubMed

Benzylisoquinoline alkaloids, such as the analgesic compounds morphine and codeine, and the antibacterial agents berberine, palmatine, and magnoflorine, are synthesized from tyrosine in the Papaveraceae, Berberidaceae, Ranunculaceae, Magnoliaceae, and many other plant families. It is difficult to produce alkaloids on a large scale under the strict control of secondary metabolism in plants, and they are too complex for cost-effective chemical synthesis. By using a system that combines microbial and plant enzymes to produce desired benzylisoquinoline alkaloids, we synthesized (S)-reticuline, the key intermediate in benzylisoquinoline alkaloid biosynthesis, from dopamine by crude enzymes from transgenic Escherichia coli. The final yield of (S)-reticuline was 55 mg/liter within 1 h. Furthermore, we synthesized an aporphine alkaloid, magnoflorine, or a protoberberine alkaloid, scoulerine, from dopamine via reticuline by using different combination cultures of transgenic E. coli and Saccharomyces cerevisiae cells. The final yields of magnoflorine and scoulerine were 7.2 and 8.3 mg/liter culture medium. These results indicate that microbial systems that incorporate plant genes cannot only enable the mass production of scarce benzylisoquinoline alkaloids but may also open up pathways for the production of novel benzylisoquinoline alkaloids. PMID:18492807

Minami, Hiromichi; Kim, Ju-Sung; Ikezawa, Nobuhiro; Takemura, Tomoya; Katayama, Takane; Kumagai, Hidehiko; Sato, Fumihiko

2008-05-27

59

Microbial production of plant benzylisoquinoline alkaloids  

PubMed Central

Benzylisoquinoline alkaloids, such as the analgesic compounds morphine and codeine, and the antibacterial agents berberine, palmatine, and magnoflorine, are synthesized from tyrosine in the Papaveraceae, Berberidaceae, Ranunculaceae, Magnoliaceae, and many other plant families. It is difficult to produce alkaloids on a large scale under the strict control of secondary metabolism in plants, and they are too complex for cost-effective chemical synthesis. By using a system that combines microbial and plant enzymes to produce desired benzylisoquinoline alkaloids, we synthesized (S)-reticuline, the key intermediate in benzylisoquinoline alkaloid biosynthesis, from dopamine by crude enzymes from transgenic Escherichia coli. The final yield of (S)-reticuline was 55 mg/liter within 1 h. Furthermore, we synthesized an aporphine alkaloid, magnoflorine, or a protoberberine alkaloid, scoulerine, from dopamine via reticuline by using different combination cultures of transgenic E. coli and Saccharomyces cerevisiae cells. The final yields of magnoflorine and scoulerine were 7.2 and 8.3 mg/liter culture medium. These results indicate that microbial systems that incorporate plant genes cannot only enable the mass production of scarce benzylisoquinoline alkaloids but may also open up pathways for the production of novel benzylisoquinoline alkaloids. PMID:18492807

Minami, Hiromichi; Kim, Ju-Sung; Ikezawa, Nobuhiro; Takemura, Tomoya; Katayama, Takane; Kumagai, Hidehiko; Sato, Fumihiko

2008-01-01

60

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

61

New pyrrolizidine alkaloids from Heliotropium crassifolium.  

PubMed

Heliotropium crassifolium Boiss, (Boraginaceae) from a population of Ilam, western region of Iran was studied for pyrrolizidine alklaoids (PAs). Four alkaloids have been identified: europine 1, europine N-oxide 2 and a new pyrrolizidine alkaloids ilamine 3 and its N-oxide 4, respectively. Their structures were elucidated by IR, 1H-NMR and EIMS data. PMID:10865467

Farsam, H; Yassa, N; Sarkhail, P; Shafiee, A

2000-05-01

62

Sesquiterpenoid alkaloid from Acroptilon repens.  

PubMed

One new sesquiterpenoid alkaloid, namely 3 beta,8 alpha-dihydroxy-13-pyrrolidine-4(15),10(14)-(1 alpha H,5 alpha H,6 beta H,11 beta H)-guaiadien-12,6-olide (1), together with two known guaiane-type sesquiternoids (2-3) was isolated from the aerial part of Acroptilon repens. The structure of 1 was established by spectroscopic methods, especially 2D NMR (HMQC, HMBC, and NOESY). Cytotoxic activity against tumor cell line was assessed for compounds 2-3, and found to show potent cytotoxic activities against tumor cell line P-388. PMID:18266151

Zhan, Zha-Jun; Hou, Xiao-Rong

2008-02-15

63

Sesquiterpenoid alkaloid from Acroptilon repens  

Microsoft Academic Search

One new sesquiterpenoid alkaloid, namely 3?,8?-dihydroxy-13-pyrrolidine-4(15),10(14)-(1?H,5?H,6?H,11?H)-guaiadien-12,6-olide (1), together with two known guaiane-type sesquiternoids (2?3) was isolated from the aerial part of Acroptilon repens. The structure of 1 was established by spectroscopic methods, especially 2D NMR (HMQC, HMBC, and NOESY). Cytotoxic activity against tumor cell line was assessed for compounds 2?3, and found to show potent cytotoxic activities against tumor cell

Zha-Jun Zhan; Xiao-Rong Hou

2008-01-01

64

Quinazoline Alkaloids and Related Chemistry  

Microsoft Academic Search

Recent progress in quinazoline alkaloids and related chemistry was reviewed focusing on developments\\u000a of the synthetic methodologies and their synthetic applications. A brief historical background,\\u000a aza–Wittig methodology, microwave-assisted synthesis, solid-phase synthesis, and a variety\\u000a of new syntheses of quinazoline compounds by organometallic reagents, metal-catalyzed reactions, heterocyclizations,\\u000a pericyclic reactions, etc. are briefly reviewed. Selected topics of total synthesis of various types\\u000a of quinazoline

Shoji Eguchi

65

Angustinine--a new benzopyridoquinolizine alkaloid from Alangium lamarckii.  

PubMed

A new benzopyridoquinolizine alkaloid, designated as angustinine (1), was isolated from the root bark of Alangium lamarckii Thwaites, along with the known ipecac alkaloid, emetine. Investigation of the stem bark of the same plant resulted in the isolation of another known ipecac alkaloid, cephaeline. The structure of the new alkaloid (1) was elucidated on the basis of 2D NMR spectralanalysis. PMID:23074898

Chakraborty, Mumu; Mukhopadhyay, Sibabrata

2012-09-01

66

Amide alkaloids from Scopolia tangutica.  

PubMed

Four new hydroxycinnamic acid amides, scotanamines A-D (1-4), and seven known alkaloids, including N (1),N (10)-di-dihydrocaffeoylspermidine (5), scopolamine (6), anisodamine (7), hyoscyamine (8), anisodine (9), caffeoylputrescine (10), and N (1)-caffeoyl-N (3)-dihydrocaffeoylspermidine (11), were obtained from the roots of Scopolia tangutica. The present study represents the first recognition of hydroxycinnamic acid amides containing putrescine or spermidine in S. tangutica. Compound 1, in particular, contains a moiety resulting from the condensation of nortropinone and putrescine. Compound 2 exhibited moderate agonist activity at the µ-opioid receptor (EC50=7.3 µM). Compound 2 was tested in vivo and induced analgesia in mice. The analgesic effect was recorded using the tail-flick assay and was reversed by naloxone. PMID:25127021

Long, Zhen; Zhang, Yan; Guo, Zhimou; Wang, Lien; Xue, Xingya; Zhang, Xiuli; Wang, Shisheng; Wang, Zhiwei; Civelli, Olivier; Liang, Xinmiao

2014-08-01

67

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

68

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

69

Metabolic engineering of plant alkaloid biosynthesis  

PubMed Central

Plant alkaloids, one of the largest groups of natural products, provide many pharmacologically active compounds. Several genes in the biosynthetic pathways for scopolamine, nicotine, and berberine have been cloned, making the metabolic engineering of these alkaloids possible. Expression of two branching-point enzymes was engineered: putrescine N-methyltransferase (PMT) in transgenic plants of Atropa belladonna and Nicotiana sylvestris and (S)-scoulerine 9-O-methyltransferase (SMT) in cultured cells of Coptis japonica and Eschscholzia californica. Overexpression of PMT increased the nicotine content in N. sylvestris, whereas suppression of endogenous PMT activity severely decreased the nicotine content and induced abnormal morphologies. Ectopic expression of SMT caused the accumulation of benzylisoquinoline alkaloids in E. californica. The prospects and limitations of engineering plant alkaloid metabolism are discussed. PMID:11134522

Sato, Fumihiko; Hashimoto, Takashi; Hachiya, Akira; Tamura, Ken-ichi; Choi, Kum-Boo; Morishige, Takashi; Fujimoto, Hideki; Yamada, Yasuyuki

2001-01-01

70

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

71

Alkaloids of the herb Sedum acre L  

Microsoft Academic Search

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

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

1977-01-01

72

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.

73

Evaluation of antinociceptive effects of Galipea longiflora alkaloid extract and major alkaloid 2-phenylquinoline.  

PubMed

The present study evaluated the antinociceptive properties of an alkaloid extract and 2-phenylquinoline obtained from the bark of Galipea longiflora Krause (Rutaceae) against different models of pain in mice. The results demonstrate that the alkaloid extract caused a pronounced antinociceptive effect with the main alkaloid detected, 2-phenylquinoline, exhibiting moderate activity. The alkaloid extract had a calculated ID50 value of 20.3 mg/kg i.p. and less than 50 mg/kg p.o. against the writhing test which proved to be more effective than the reference drugs when administered by both routes. The ID50 of 2-phenylquinoline was 52.8 mg/kg i.p. with an inhibition of 24.5% when administered orally at 100 mg/kg. In the formalin test the alkaloid extract, but not 2-phenylquinoline, significantly inhibited both phases of pain (neurogenic and inflammatory) at 10 mg/kg i.p. with inhibitions of 37.4% and 58.3%, respectively. The alkaloid extract and 2-phenylquinoline caused only a modest effect in the capsaicin and glutamate tests. In the hot plate test, the alkaloid extract increased the latency time by 25.6% at 10 mg/kg i.p. compared to 2-phenylquinoline which was less effective. It appears that the antinociceptive effects of this plant may be attributed, at least in part, to the presence of some antinociceptive alkaloids in minor concentrations. PMID:21225005

Campos-Buzzi, F; Fracasso, M; Clasen, B K; Ticona, J C; Gimenez, A; Cechinel-Filho, V

2010-12-01

74

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

75

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

76

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

77

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

78

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

79

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

80

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

81

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

82

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

83

Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt)  

Microsoft Academic Search

Altogether 40 pyrrolizidine alkaloids were detected in the alkaloid extracts of Paracaryum rugulosum, P. intermedium, Anchusa milleri, Gastrocotyle hispida (syn. Anchusa hispida), Anchusa arvensis, Lappula spinocarpos, Trichodesma africanum, Alkanna orientalis, and Alkanna tuberculata (syn. A. tinctoria) which were analyzed by capillary GLC and GLC-MS. 24 alkaloids were unambiguously identified by comparing their specific retention indices and mass fragmentations with those

Assem El-Shazly; Maher El-Domiaty; Ludger Witte; Michael Wink

1998-01-01

84

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

85

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

86

Supramolecular adsorption of alkaloids by metallosalphen complexes.  

PubMed

Mono and bis-zinc(II)-centered salphen derivatives 1-5 are presented as efficient adsorption materials for pyridine-based alkaloid derivatives. The different alkaloid assemblies were studied by UV-vis and NMR spectroscopy, and high binding constants (Ks approximately 10(5)) were additionally determined for the supramolecular complexes based on nicotine. X-ray analyses furthermore revealed, together with spectroscopic solution data, a preferential positioning of the nicotine guest(s). Upon binding to bis-Zn(II)-bis-salphen complexes, the dinicotine assembly provokes a colorimetric change that may be useful for colorimetric analyses. The adsorption/desorption process of nicotine was studied using a polymeric bis-Zn(salphen) complex (5) and showed a recycling potential of this type of complexes in the binding of alkaloid compounds. PMID:18410090

Escudero-Adán, Eduardo C; Benet-Buchholz, Jordi; Kleij, Arjan W

2008-05-19

87

Evaporative light scattering detection of pyrrolizidine alkaloids.  

PubMed

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

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

2004-01-01

88

Pyrrolizidine alkaloids from Echium glomeratum (Boraginaceae).  

PubMed

The methanolic extract of the whole plant of Echium glomeratum Poir. (Boraginaceae) has afforded five pyrrolizidine alkaloids, three that were (7S, 8R)-petranine (1), (7S, 8S)-petranine (2), and (7R, 8R)-petranine (3a) or (7R, 8S)-petranine (3b), comprising a tricyclic pyrrolizidine alkaloids subclass; and two that were known but to the species: 7-angeloylretronecine (4) and 9-angeloylretronecine (5). All compounds were tested against a human tumor panel for cytotoxicity; no activity was observed (EC50 values>20microg/ml). PMID:18691727

Alali, Feras Q; Tahboub, Yahya R; Ibrahim, Eyad S; Qandil, Amjad M; Tawaha, Khaled; Burgess, Jason P; Sy, Arlene; Nakanishi, Yuka; Kroll, David J; Oberlies, Nicholas H

2008-09-01

89

GENOTOXIC PYRROLIZIDINE ALKALOIDS AND PYRROLIZIDINE ALKALOID N-OXIDES—MECHANISMS LEADING TO DNA ADDUCT FORMATION AND TUMORIGENICITY  

Microsoft Academic Search

Plants that contain pyrrolizidine alkaloids and pyrrolizidine alkaloid N-oxides are widely distributed in the world. These plants are probably the most common poisonous plants affecting livestock, wildlife, and humans. Although pyrrolizidine alkaloids have been shown to be genotoxic, including tumorigenic in experimental animals, the mechanisms of tumor formation have not been fully understood. Our recent studies on riddelliine, riddelline N-oxide,

P. P. Fu; M. W. Chou; Q. Xia; Y.-C. Yang; J. Yan; D. R. Doerge; P. C. Chan

2001-01-01

90

Physiologisch - Chemische Grundlagen der Chinolizidin-Alkaloid - Biosynthese (Physiological - Chemical Bases of Quinolizidine Alkaloid - Biosynthesis).  

National Technical Information Service (NTIS)

Callus cultures were established from 14 alkaloid plants. Cultivation as a suspension culture was possible for 10 of these. Growth conditions were optimized for Lupinus polyphyllus, Sarothamnus scoparius, Baptisia australis, Conium maculatum and Symphytum...

M. Wink

1980-01-01

91

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

Microsoft Academic Search

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

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

1998-01-01

92

New spermidine alkaloids from Capparis spinosa roots  

Microsoft Academic Search

Three new spermidine alkaloids capparispine (1), capparispine 26-O-?-d-glucoside (2) and cadabicine 26-O-?-d-glucoside hydrochloride (3) were isolated from the roots of Capparis spinosa. Their structures were established on the basis of spectroscopic analysis, including 1D and 2D NMR experiments (1H–1H COSY, HSQC, HMBC).

Xiao Pu Fu; Tao Wu; Miriban Abdurahim; Zhen Su; Xue Ling Hou; Haji Akber Aisa; Hankui Wu

2008-01-01

93

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

94

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

95

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

96

Four new Amaryllidaceae alkaloids from Zephyranthes candida.  

PubMed

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

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

2014-07-01

97

Pyrrolizidine alkaloids from Ageratum houstonianum Mill.  

PubMed

Four pyrrolizidine alkaloids (PA) were isolated from Ageratum houstonianum and their structures elucidated by spectroscopical methods. Besides the already known lycopsamine three new PA were found. Their structures are the 2S-2-hydroxy-2,3-dimethyl-butanoyl-O(9) as well as the O(7) esters of retronecine and the O(9) derivative of heliotridine. PMID:11454357

Wiedenfeld, H; Andrade-Cetto, A

2001-08-01

98

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

99

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

100

Adsorption chromatography of alkaloids of fumaria officinalis  

Microsoft Academic Search

Seven alkaloids of Fumaria officinalis, difficult to separate by partition chromatography and countercurrent distribution, were separated by column chromatography using silica gel developed with mixtures of propanol or methanol with nonpolar solvents. Suitable solvent systems for column chromatography were chosen on the basis of thin layer chromatography data.

W. Golkiewicz; T. Wawrzynowicz

1970-01-01

101

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

102

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.; Aube, Jeffrey

2014-01-01

103

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

104

Alkaloid formation by habituated and tumorous cell suspension cultures of Catharanthus roseus  

Microsoft Academic Search

Habituated and tumorous Catharanthus roseus cells grown in the absence of hormones accumulated indole alkaloids. Total alkaloids and alkaloid pattern were the same when cells were cultured in medium without hormones or in alkaloid production medium with and without indole acetic acid. Treatment of cells with Pythium homogenate as elicitor did not increase total alkaloids or change the pattern of

U. Eilert; V. DeLuca; W. G. W. Kurz; F. Constabel

1987-01-01

105

The epichloae: alkaloid diversity and roles in symbiosis with grasses  

PubMed Central

Epichloae (Epichloë and Neotyphodium species; Clavicipitaceae) are fungi that live in systemic symbioses with cool-season grasses, and many produce alkaloids that are deterrent or toxic to herbivores. The epichloae colonize much of the aerial plant tissues, and most benignly colonize host seeds to transmit vertically. Of their four chemical classes of alkaloids, the ergot alkaloids and indole-diterpenes are active against mammals and insects, whereas peramine and lolines specifically affect insects. Comparative genomic analysis of Clavicipitaceae reveals a distinctive feature of the epichloae, namely, large repeat blocks in their alkaloid biosynthesis gene loci. Such repeat blocks can facilitate gene losses, mutations, and duplications, thus enhancing diversity of alkaloid structures within each class. We suggest that alkaloid diversification is selected especially in the vertically transmissible epichloae. PMID:23850071

Schardl, Christopher L; Florea, Simona; Pan, Juan; Nagabhyru, Padmaja; Bec, Sladana; Calie, Patrick J

2013-01-01

106

Quinolizidine alkaloid biosynthesis: recent advances and future prospects  

PubMed Central

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

Bunsupa, Somnuk; Yamazaki, Mami; Saito, Kazuki

2012-01-01

107

Pyrrolizidine alkaloid profiles of some Senecio species from Egypt.  

PubMed

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

El-Shazly, Assem

2002-01-01

108

Chirality and numbering of substituted tropane alkaloids.  

PubMed

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

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

2011-01-01

109

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

Microsoft Academic Search

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

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

1996-01-01

110

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

111

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

Microsoft Academic Search

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

Russell J. Molyneux; M. Benson; Y. T. Pan; J. E. Tropea; G. P. Kaushal; Alan D. Elbein

1991-01-01

112

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

113

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

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

2011-01-01

114

Alkaloids and flavonoids of Argemone mexicana.  

PubMed

A new protopine alkaloid, protomexicine and a new isoflavonoid, mexitin, together with 8-methoxydihydrosanguinarine, 13-oxoprotopine, rutin and quercetrin have been isolated from the aerial part of the methanolic extract of Argemone mexicana. The structures of these compounds have been established by various spectral data. The structure of protomexicine was further confirmed by heteronuclear multiple bond correlation experiment. Protomexicine and mexitin are new compounds, and other compounds are first reported from A. mexicana and genus Argemone. PMID:21722040

Singh, Sarita; Pandey, Vidya Bhushan; Singh, Tryambak Deo

2012-01-01

115

A new Erythrina alkaloid from Erythrina herbacea  

Microsoft Academic Search

A new Erythrina alkaloid, 10-hydroxy-11-oxoerysotrine (1), has been isolated from the flowers of Erythrina herbacea together with five known compounds: erytharbine (2), 10,11-dioxoerysotrine (3), erythrartine (4), erysotramidine (5) and erysotrine-N-oxide (6). The structure of the new compound was elucidated on the basis of its spectral data, including 2-D NMR and mass (MS) spectra.\\u000a The new compound is a rare C-10

Hitoshi Tanaka; Hisanori Hattori; Toshihiro Tanaka; Eiji Sakai; Nobuyuki Tanaka; Aditya Kulkarni; Hideo Etoh

2008-01-01

116

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

2012-06-07

117

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… (more)

Runguphan, Weerawat

2011-01-01

118

Pyrrolizidine alkaloid profiles of the Senecio cineraria group (Asteraceae).  

PubMed

Alkaloid profiles of five Senecio species (Asteraceae), including S. ambiguus subsp. ambiguus, S. ambiguus subsp. nebrodensis, S. gibbosus subsp. bicolor, S. gibbosus subsp. gibbosus, and S. gibbosus subsp. cineraria, were studied. Eleven pyrrolizidine alkaloids were identified and their content was evaluated by GLC-MS and GLC analysis. Otosenine and florosenine were found to be the major alkaloids in all studied species. It is interesting that only S. ambiguus subsp. nebrodensis was characterized by a high content of the alkaloids jacobine, jacoline, jaconine, and jacozine. PMID:17913058

Tundis, Rosa; Loizzo, Monica R; Statti, Giancarlo A; Passalacqua, Nicodemo G; Peruzzi, Lorenzo; Menichini, Francesco

2007-01-01

119

Dietary alkaloid sequestration in a poison frog: an experimental test of alkaloid uptake in Melanophryniscus stelzneri (Bufonidae).  

PubMed

Several lineages of brightly colored anurans independently evolved the ability to secrete alkaloid-containing defensive chemicals from granular glands in the skin. These species, collectively referred to as 'poison frogs,' form a polyphyletic assemblage that includes some species of Dendrobatidae, Mantellidae, Myobatrachidae, Bufonidae, and Eleutherodactylidae. The ability to sequester alkaloids from dietary arthropods has been demonstrated experimentally in most poison frog lineages but not in bufonid or eleutherodactylid poison frogs. As with other poison frogs, species of the genus Melanophryniscus (Bufonidae) consume large numbers of mites and ants, suggesting they might also sequester defensive alkaloids from dietary sources. To test this hypothesis, fruit flies dusted with alkaloid/nutritional supplement powder were fed to individual Melanophryniscus stelzneri in two experiments. In the first experiment, the alkaloids 5,8-disubstituted indolizidine 235B' and decahydroquinoline were administered to three individuals for 104 days. In the second experiment, the alkaloids 3,5-disubstituted indolizidine 239Q and decahydroquinoline were given to three frogs for 153 days. Control frogs were fed fruit flies dusted only with nutritional supplement. Gas chromatography/mass spectrometry analyses revealed that skin secretions of all experimental frogs contained alkaloids, whereas those of all control frogs lacked alkaloids. Uptake of decahydroquinoline was greater than uptake of 5,8-disubstituted indolizidine, and uptake of 3,5-disubstituted indolizidine was greater than uptake of decahydroquinoline, suggesting greater uptake efficiency of certain alkaloids. Frogs in the second experiment accumulated a greater amount of alkaloid, which corresponds to the longer duration and greater number of alkaloid-dusted fruit flies that were consumed. These findings provide the first experimental evidence that bufonid poison frogs sequester alkaloid-based defenses from dietary sources. PMID:24190023

Hantak, Maggie M; Grant, Taran; Reinsch, Sherri; McGinnity, Dale; Loring, Marjorie; Toyooka, Naoki; Saporito, Ralph A

2013-12-01

120

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… (more)

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

2010-01-01

121

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.

122

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

123

Ergot alkaloids--biology and molecular biology.  

PubMed

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

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

2006-01-01

124

Diversification of monoterpene indole alkaloid analogs through cross-coupling.  

PubMed

Catharanthus roseus monoterpene indole alkaloid analogs have been produced via a combination of biosynthetic and chemical strategies. Specifically, introduction of a chemical handle-a chlorine or a bromine-into the target molecule by mutasynthesis, followed by postbiosynthetic chemical derivatization using Pd-catalyzed Suzuki-Miyaura cross-coupling reactions robustly afforded aryl and heteroaryl analogs of these alkaloids. PMID:23713451

Runguphan, Weerawat; O'Connor, Sarah E

2013-06-01

125

Alkaloid production in Catharanthus roseus (L.) G. Don  

Microsoft Academic Search

Analysis of 76 cell clones derived from one leaf of a periwinkle plant (Catharanthus roseus (L.) G. Don) showed the occurrence of Corynanthe-, Strychnos-, and Aspidosperma-type alkaloids. The majority of clones (62%) displayed compounds of all three types. Variation of the alkaloid spectra of the cell clones was low when compared to that found previously with serially subcultured callus and

F. Constabel; S. Rambold; K. B. Chatson; W. G. M. Kurz; J. P. Kutney

1981-01-01

126

Alkaloid production by transformed root cultures of Catharanthus roseus  

Microsoft Academic Search

Transformed roots of Catharanthus roseus were obtained following infection of detached leaves with Agrobacterium rhizogenes. Roots would not grow in full strength Gamborg's B5 medium but would grow satisfactorily if the medium was diluted to one half strength. Little alkaloid appeared in the growth medium but root tissue contained a high level and wide variety of alkaloids. Ajmalicine, serpentine, vindolinine

A. J. Parr; A. C. J. Peerless; J. D. Hamill; N. J. Walton; R. J. Robins; M. J. C. Rhodes

1988-01-01

127

Phenanthropiperidine Alkaloids: Methodology Development, Synthesis and Biological Evaluation  

E-print Network

and analogs 307 .......................................................................................6.5.2 Biological procedures 330 .........................................................................6.5.2.1 Anti-proliferation assay 330... phenanthropiperidine alkaloids, most investigations have focused on the pharmacology of the purified alkaloids rather than on plant-derived mixtures and hence will be discussed later. On the other hand, the efficacy and mode of action of T. indica for the treatment...

Niphakis, Micah James

2010-04-08

128

[Alkaloids of Vinca rosea L. introduced to Western Georgia].  

PubMed

Vinca roseae L. (??tharanthus rosea (L.) G. Don) was introduced at Kobuleti experimental station of medical plants. The object of investigation was the plant material of Vinca roseae L. collected in May, 2005., September, 2006 and October, 2009. Total alkaloids were obtained in accordance with Atta- ur-Rachman method. The variability of the quantitative and qualitative composition of total alkaloids and vincaleikoblastin (VLB) fraction during vegetation was studied. It was established that the maximal content of total alkaloids and VLB fraction of Vinca roseae L. is accumulated in the phase of secondary flowering, hence the collecting of a plant material is recommended to be made during the aforesaid vegetation phase as for this period it is a rather high output of a raw material, alkaloid complex and VLB faction. Alkaloids vinkaleikoblastin, ajmalicine and new epimer tetrahydroalstonine with ?3?-?- orientation were yielded, separated and identified using modern physical-chemical and spectral methods (13? NMR). PMID:24323972

Vachnadze, N S; Kintsurashvili, L G; Suladze, T Sh; Bakuridze, A D; Vachnadze, V Iu

2013-11-01

129

Pyrrolizidine alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae).  

PubMed

Echimidine was isolated from Echium rauwolfii and Echium horridum and identified by MS, 1H- and 13C NMR as a major alkaloid. In addition, structures of 12 minor alkaloids were inferred from GLC and GLC-MS analyses: 7-angeloylretronecine, 7-tigloylretronecine, lycopsamine, 7-acetyllycopsamine, uplandicine, 7-angeloyllycopsamine, 7-tigloyllycopsamine, tigloyl isomer of echimidine, 7-angeloyl-9-(2-methylbutyryl)retronecine, 7-tigloyl-9-(2-methylbutyryl)retronecine, 7-angeloyl-9-(2,3-dihydroxybutyryl)retronecine, and 7-tigloyl-9-(2,3-dihydroxybutyryl)retronecine. Both species had similar alkaloid profiles. Alkaloid extracts exhibited antibacterial effects with a MIC of 1.7 mg/ml in E. coli. Microscopic examination of E. coli treated with different subtoxic alkaloid concentrations (13-52 micrograms/ml) revealed extensive filamentation. PMID:10431383

el-Shazly, A; Abdel-All, M; Tei, A; Wink, M

1999-01-01

130

Ergot alkaloid glycosides with immunomodulatory activities  

Microsoft Academic Search

New glycosides derived from ergot alkaloids elymoclavine and DH-lysergol were synthesized by chemoenzymatic methods. ?-Glucosides were obtained either by chemical method or by transglycosylation (glycosidase from Aspergillus oryzae), lactosides were prepared by further extension of carbohydrate chain using ?-1,4-galactosyltransferase (bovine milk) and ?-5-N-acetylneuraminyl-(2?6)-?-d-galactopyranosyl-(1?4)- 2-acetamido-2-deoxy-?-d-glucopyranosyl-(1?O)-elymoclavine was prepared using ?-2,6-sialyltransferase (rat liver). Immunomodulatory activity of elymoclavine and 9,10-dihydrolysergol and their glycosylated derivatives

Vladimír K?en; Anna Fišerová; Claudine Augé; Petr Sedmera; Vladimír Havlí?ek; Petr Šíma

1996-01-01

131

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.

132

Plants containing pyrrolizidine alkaloids: toxicity and problems.  

PubMed

Pyrrolizidine alkaloids (PA) are toxic for human and livestock. They undergo a metabolic toxication process in the liver which is the first target organ for PA poisoning. Worldwide many episodes of human PA intoxications are well reported. In many cases the reason for these intoxications has been PA contamination in food. The main tools for analysing food and fodder on PA content are based on GC and HPLC separation, followed by MS(-MS) detection. Actual incidents with toxic PA are the 'Jacobaea vulgaris (syn. Senecio jacobaea) problem' in Europe and the 'Ageratum conyzoides problem' in Ethiopia. PMID:21360374

Wiedenfeld, H

2011-03-01

133

Alkaloids of the Sedum acre -group ( Crassulaceae )  

Microsoft Academic Search

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

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

1993-01-01

134

Pyrrolizidine alkaloids from Lithospermum canescens Lehm.  

PubMed

Seven pyrrolizidine alkaloids (PAs) have been isolated from Lithospermum canescens and their structures determined by spectroscopical methods. Besides the known lycopsamine, O7-acetyl-lycopsamine and O7-acetylintermedine four new PAs were found. Their structures are O7-(3-hydroxy-3-methyl-butanoyl)-O9-(+)-trachelanthoyl-heliotridine (= O7-(3-hydroxy-3-methyl-butanoyl)-rinderine = canescine), O7-(3-hydroxy-3-methyl-butanoyl)-O9-(-)-viridifloryl-heliotridine (= O7-(3-hydroxy-3-methyl-butanoyl)-echinatine = canescenine and their O13-acetyl-derivatives (= acetylcanescine; acetylcanescenine). PMID:12710723

Wiedenfeld, Helmut; Pietrosiuk, Agnieszka; Furmanowa, Miroslava; Roeder, Erhard

2003-01-01

135

A new pyrroloquinazoline alkaloid from Linaria vulgaris.  

PubMed

A new alkaloid, 1,2,3,9-tetrahydropyrrolo(2,1-b)quinazolin-1-carboxylic acid (1), together with eight known compounds, 7-hydroxy vasicine (2), benzyl alcohol beta-D-(2'-O-beta-xylopyranosyl)glucopyranoside (3), benzyl alcohol O-beta-D-glucopyranoside (4), benzyl alcohol O-beta-D-primveroside (5), 3,5-dimethyl-4-hydroxy benzaldehyde (6), gluco-syringic acid (7), syringin (8), and liriodendrin (9), were isolated from the plants of Linaria vulgaris. Their structures were established by spectroscopic methods. PMID:12372872

Hua, Huiming; Cheng, Maosheng; Li, Xian; Pei, Yuehu

2002-10-01

136

Ergot alkaloid glycosides with immunomodulatory activities.  

PubMed

New glycosides derived from ergot alkaloids elymoclavine and DH-lysergol were synthesized by chemoenzymatic methods. beta-Glucosides were obtained either by chemical method or by transglycosylation (glycosidase from Aspergillus oryzae), lactosides were prepared by further extension of carbohydrate chain using beta-1,4-galactosyltransferase (bovine milk) and alpha-5-N-acetylneuraminyl-(2-->6)-beta-D-galactopyranosyl-(l-->4)-2- acetamido-2-deoxy-beta-D-glucopyranosyl-(1-->O)-elymoclavine was prepared using alpha-2,6-sialyltransferase (rat liver). Immunomodulatory activity of elymoclavine and 9,10-dihydrolysergol and their glycosylated derivatives on natural killer (NK) cell-mediated cytotoxicity of human resting and activated human peripheral blood mononuclear cells (PBMC) was investigated. Addition of ergot alkaloid glycosides to the mixtures of effector and target cells potentiated the PBMC cytotoxicity against both NK-sensitive and -resistant target cells. The glycoconjugates of elymoclavine enhanced cytotoxicity of PBMC against NK-resistant target cells. The glycoconjugates of DH-lysergol potentiated NK cytotoxicity of PBMC against NK-sensitive target cells. PMID:8818236

Kren, V; Fiserová, A; Augé, C; Sedmera, P; Havlícek, V; Síma, P

1996-06-01

137

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

138

Pyrrolizidine alkaloids of Echium vulgare honey found in pure pollen.  

PubMed

The pyrrolizidine alkaloids previously identified in floral honey attributed to Echium vulgare (Boraginaceae) have been detected (8000-14 000 ppm) in pure pollen collected from the anthers of Echium vulgare. Pyrrolizidine alkaloids and/or their N-oxides were isolated from the aqueous acid extracts of pollen by use of strong cation-exchange, solid-phase extraction and identified by liquid chromatographic/mass spectrometric (LCMS) analysis. The pyrrolizidine alkaloids in the pollen are present mainly as the N-oxides. In addition to seven previously described pyrrolizidine alkaloids and/or their N-oxides (echimidine, acetylechimidine, uplandicine, 9-O-angelylretronecine, echiuplatine, leptanthine, and echimiplatine), one unidentified (echivulgarine), but previously found in honey, and two previously undescribed (vulgarine and 7-O-acetylvulgarine) pyrrolizidine alkaloids and/or their N-oxides were identified in the pollen. Tentative structures for these unidentified pyrrolizidine alkaloids are proposed on the basis of the mass spectrometric data and biogenetic considerations. The implications of these results for identifying the source and subsequent concentrations of pyrrolizidine alkaloids in honeys and commercial bee pollen are briefly discussed. PMID:15686407

Boppré, Michael; Colegate, Steven M; Edgar, John A

2005-02-01

139

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

140

The effect of isoquinoline alkaloids on opiate withdrawal.  

PubMed

Our interest has been centered on isoquinoline alkaloids obtained from Argemone mexicana (Papaveraceae), Aristolochia constricta (Aristolochiaceae) and the opium alkaloid, papaverine. In this respect, the effect of these isoquinoline alkaloids was investigated on contractions induced by naloxone of isolated guinea pig ileum acutely exposed to morphine in vitro. The activity of these alkaloids was compared to the control compound, papaverine. Furthermore, the effect of these isoquinoline alkaloids was also determined on naloxone-precipitated withdrawal in isolated guinea pig ileum exposed to DAMGO (highly selective mu opioid receptor agonist) and U50-488H (highly selective kappa opioid receptor agonist) to test whether the possible interaction of isoquinoline alkaloids on opioid withdrawal involves mu- and/or kappa-opioid receptors. Isoquinoline alkaloids from A. mexicana (from 5 x 10(-6) to 1 x 10(-4) M), from A. constricta (1 x 10(-5) x 10(-5)-1 x 10(-4) M) as well as papaverine treatment (1 x 10(-7)-5 x 10(-6)-1 x 10(-6) M) before or after the opioid agonists were able of both preventing and reversing the naloxone-induced contraction after exposure to mu (morphine and DAMGO) or kappa (U50-488H) opiate receptor agonists in a concentration-dependent manner. Both acetylcholine response and electrical stimulation were also reduced by isoquinoline alkaloids and papaverine treatment as well as the final opiate withdrawal was still reduced. The results of the present study indicate that isoquinoline alkaloids as well as papaverine were able to produce significant influence on the opiate withdrawal in vitro and these compounds were able to exert their effects both at mu and kappa opioid agonists. PMID:16611069

Capasso, A; Piacente, S; De Tommasi, N; Rastrelli, L; Pizza, C

2006-01-01

141

Regulation of the immune response by ergot alkaloids.  

PubMed

We tested the effect of 33 ergot alkaloids (natural and semisynthetic) on the induction of antibody formation in isolated spleen cells by antigen in tissue cultures. The results are quantitatively expressed as the number of antibody-forming cells. The group of natural ergot alkaloids (ergopeptines) exerted an effective inhibitory action on the antibody response. Compounds derived from lysergic acid are completely inactive in this respect. A new, very active semisynthetic drug (Table 1, compounds 2) derived from inactive lysergol was described. The compounds interacting with alpha-adrenergic-receptors on lymphocytes (methoxamine, phentolamine, prazosin act synergistically with the inhibitory effect of ergopeptine alkaloids. PMID:2888605

Sterzl, J; Rehácek, Z; Cudlín, J

1987-01-01

142

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; Hanus, Lumir O; Dembitsky, Valery M

2008-01-01

143

Cytotoxic eburnamine-aspidospermine type bisindole alkaloids from Bousigonia mekongensis.  

PubMed

Four new eburnamine-aspidospermine type bisindole alkaloids, namely, mekongenines C-F (1-4), along with 27 known indole alkaloids were isolated from the twigs and leaves of Bousigonia mekongensis. Their structures with the absolute configurations were elucidated by spectroscopic methods and ECD analyses. All new compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Alkaloids 1-4 exhibited inhibitory effects with IC50 values comparable to those of cisplatin. PMID:25038470

Fu, Yan-Hui; Li, Shun-Lin; Li, Shi-Fei; He, Hong-Ping; Di, Ying-Tong; Zhang, Yu; Hao, Xiao-Jiang

2014-10-01

144

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

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

2008-01-01

145

Total Synthesis of Alkaloid 205B.  

PubMed

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

Tsukanov, Sergey V; Comins, Daniel L

2014-10-01

146

Medicinal plants in China containing pyrrolizidine alkaloids.  

PubMed

Medicinal plants and remedies are widely used for various ailments throughout the world. Many of these plants contain pyrrolizidine alkaloids (PAs) which are hepatotoxic, pneumotoxic, genotoxic, neurotoxic, and cytotoxic. As a result of their use in Traditional Chinese Medicine (TCM), medicinal plants are becoming increasingly important not only in China but also in many other countries. This paper will therefore give, a critical overview of PA-containing plants belonging mainly to the families Boraginaceae, Leguminosae (Tribus Crotalarieae), and Asteraceae (Tribus Senecioneae and Eupatorieae). The PAs contained in the 38 plants described here differ widely in their structure and toxicity. Their metabolism and the resulting toxicity will be discussed, the dehydroalkaloids (DHAlk) produced in the liver playing a key role in cases of intoxications. PMID:11082830

Roeder, E

2000-10-01

147

Pyrrolizidine alkaloids in pollen and pollen products.  

PubMed

Recently, 1,2-dehydropyrrolizidine alkaloid (PA) ester alkaloids, found predominantly as their N-oxides (PANOs, pyrrolizidine N-oxides), have been reported in both honey and in pollen obtained directly from PA plants and pollen loads collected by bees, raising the possibility of health risks for consumers of these products. We confirm these findings in regard to floral pollen, using pollen collected directly from flowers of the known PA plants Senecio jacobaea, S. vernalis, Echium vulgare and pollinia of Phalaenopsis hybrids, and we extend analyses of 1,2-unsaturated PAs and 1,2-unsaturated PANOs to include bee-pollen products currently being sold in supermarkets and on the Internet as food supplements. PA content of floral pollen ranged from 0.5 to 5 mg/g. The highest values were observed in pollen obtained from Senecio species. Up to 95% of the PAs are found as PANOs. Detailed studies with S. vernalis revealed unique PA patterns in pollen and flowers. While seneciphylline was the most prominent PA in S. vernalis pollen, the flowers were dominated by senecionine. To analyze trace amounts of 1,2-unsaturated PAs in pollen products, our previously elaborated method consisting of strong cation exchange-SPE, two reduction steps followed by silylation and subsequent capillary high-resolution GC-MS using SIM mode was applied. In total, 55 commercially available pollen products were analyzed. Seventeen (31%) samples contained 1,2-unsaturated PAs in the range from 1.08 to 16.35 microg/g, calculated as retronecine equivalents. The 1,2-unsaturated PA content of pollen products is expressed in terms of a single sum parameter and no background information such as foraged plants, pollen analysis, etc. was needed to analyze the samples. The detection limit of overall procedure and the reliable quantitation limit were 0.003 and 0.01 microg/g, respectively. PMID:20013884

Kempf, Michael; Heil, Sandra; Hasslauer, Iris; Schmidt, Lukas; von der Ohe, Katharina; Theuring, Claudine; Reinhard, Annika; Schreier, Peter; Beuerle, Till

2010-02-01

148

Reaction of Chloroacetone with Cytisine and d Pseudoephedrine Alkaloids  

Microsoft Academic Search

Alkylation of cytisine and d-pseudoephedrine alkaloids with chloroacetone was performed. The target product of the reaction with cytisine is aminoacetone and of the reaction with d-pseudoephedrine, a morpholine derivative.

O. A. Nurkenov; A. M. Gazaliev; K. M. Turdybekov; A. B. Bukeeva; I. V. Kulakov

2003-01-01

149

[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

150

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

151

Ergot alkaloid from the sea slug Pleurobranchus forskalii.  

PubMed

The sea slug Pleurobranchus forskalii is a carnivorous scavenger that is widely distributed in shallow subtidal areas. Very few investigations of the chemical components of this gastropod have been reported. In this study we performed a comprehensive analysis of an extract of the marine mollusc, P. forskalii, collected off Ishigaki Island, Japan. As a result, an alkaloid was isolated from the chloroform extract. Remarkably, the structure elucidation based on the spectral data revealed that it was an ergot alkaloid peptide, ergosinine. Various ergot alkaloids have previously been isolated mainly from terrestrial higher plants or fungi. This is the first report of the isolation of an ergopeptine from marine life, and thus the known geographical extent of ergot alkaloids now includes both terrestrial and aquatic organisms. PMID:23770424

Wakimoto, Toshiyuki; Tan, Karen Co; Abe, Ikuro

2013-09-01

152

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

153

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

154

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

155

Arginine decarboxylase as the source of putrescine for tobacco alkaloids  

NASA Technical Reports Server (NTRS)

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

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

1986-01-01

156

Thirty years of discovering arthropod alkaloids in amphibian skin.  

PubMed

Amphibian skin has provided a wide range of biologically active alkaloids. During the past 30 years, over 400 alkaloids of over 20 structural classes have been detected. These include the batrachotoxins, which are potent and selective activators of sodium channels, the histrionicotoxins, which are potent noncompetitive blockers of nicotinic receptor-gated channels, the pumiliotoxins and related allo- and homo-pumiliotoxins, which have myotonic and cardiotonic activity due to effects on sodium channels, and epibatidine, which has potent antinociceptive activity due to agonist activity at nicotinic receptors. Further classes of alkaloids from amphibian skin include pyrrolidines and piperidines, decahydroquinolines, pyrrolizidines, various indolizidines, quinolizidines, and tricyclic gephyrotoxins, pyrrolizidine oximes, pseudophrynamines, coccinellines, and cyclopentaquinolizidines. Most alkaloids of amphibian skin appear to be sequestered from dietary arthropods. The source of the batrachotoxins, histrionicotoxins, pumiliotoxins, epibatidine, and certain izidines are unknown. PMID:9461669

Daly, J W

1998-01-01

157

Uptake and metabolism of pyrrolizidine alkaloids in Longitarsus flea beetles (Coleoptera: Chrysomelidae) adapted and non-adapted to alkaloid-containing host plants  

Microsoft Academic Search

Several Longitarsus flea beetle species sequester pyrrolizidine alkaloids acquired from their Asteraceae and Boraginaceae host plants. We carried out feeding and injection experiments using radioactively labeled pyrrolizidine alkaloids to investigate the physiological mechanisms of uptake, metabolism and storage of alkaloids in adult beetles. We examined six Longitarsus species belonging to different phylogenetic clades in a comparative approach. All species that

I. Narberhaus; C. Theuring; T. Hartmann; S. Dobler

2003-01-01

158

Pyrrolizidine Alkaloids of Echium vulgare Honey Found in Pure Pollen  

Microsoft Academic Search

The pyrrolizidine alkaloids previously identified in floral honey attributed to Echium vulgare (Boraginaceae) have been detected (8000-14 000 ppm) in pure pollen collected from the anthers of Echium vulgare. Pyrrolizidine alkaloids and\\/or their N-oxides were isolated from the aqueous acid extracts of pollen by use of strong cation-exchange, solid-phase extraction and identified by liquid chromatographic\\/mass spectrometric (LCMS) analysis. The pyrrolizidine

Michael Boppré; Steven M. Colegate; John A. Edgar

2005-01-01

159

N-Demethylation of N-methyl alkaloids with ferrocene  

Microsoft Academic Search

Under Polonovski-type conditions, ferrocene has been found to be a convenient and efficient catalyst for the N-demethylation of a number of N-methyl alkaloids such as opiates and tropanes. By judicious choice of solvent, good yields have been obtained for dextromethorphan, codeine methyl ether, and thebaine. The current methodology is also successful for the N-demethylation of morphine, oripavine, and tropane alkaloids,

Gaik B. Kok; Peter J. Scammells

2010-01-01

160

Castanospermine and other polyhydroxy alkaloids as inhibitors of insect glycosidases  

Microsoft Academic Search

The inhibition of glycosidase activity by a range of polyhydroxy alkaloids was studied in a number of insect species from the orders Orthoptera, Phasmida, Dictyoptera, Diptera and Coleoptera. Glycosidase activity was inhibited by a number of the alkaloids and the pattern of inhibition of hydrolysis of ?-glucosides and most ?-glucosides (except trehalose) was different from that in mammals. 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine inhibited

A. M. Scofield; P. Witham; R. J. Nash; G. C. Kite; L. E. Fellows

1995-01-01

161

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

162

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

163

Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.  

PubMed

Ergot alkaloids are mycotoxins which are produced among fungi in the family Clavicipitaceae. Poisoning with ergot alkaloids is an important veterinary problem in animal husbandry and has recently also been recognised in wild animals. While the poisoning syndrome observed in domestic animals such as cattle, horses and sheep is usually caused by endophyte-infected grass, the recently observed ergotism among Norwegian cervids is probably due to infection of wild grasses with Claviceps. Mass spectrometry is today the method of choice for the rapid qualitative and quantitative determination of many natural compounds. This study uses tandem quadrupole mass spectrometry as well as ion trap mass spectrometry in connection with electrospray(+) ionisation for the quantification, screening and fragmentation of ergot alkaloids in extracts from Claviceps sclerotia that had been picked from wild grasses from several locations in Norway. Ergotamine, ergovaline, ergonovine and ergocryptine were available as standards and were quantified in the extracts, while ergocrystine, ergocornine, ergonine/ergosine, lysergic acid and lysergol were identified on the basis of their molecular weights and semi-quantified. Ergocrystine dominated the alkaloid spectrum of most extracts. Levels of the quantified alkaloids were in the range 0.2-9300 microg/g. Several unknown ergot alkaloids were found in the extracts. MS(n) experiments identified some as simple lysergic acid amide derivatives, while othes are probably related to ergocrystine and ergocryptine by dehydration, dehydrogenation and/or amino acid substitution at R(1) of the peptide moiety. PMID:17465016

Uhlig, Silvio; Vikøren, Turid; Ivanova, Lada; Handeland, Kjell

2007-01-01

164

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

165

Pyrrolizidine alkaloids in honey and bee pollen.  

PubMed

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

Dübecke, A; Beckh, G; Lüllmann, C

2011-03-01

166

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

167

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

E-print Network

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

Hunt, Diana Katharine

2006-01-01

168

Hydrachine A, a novel alkaloid from the roots of Hydrangea chinensis.  

PubMed

A novel alkaloid, hydrachine A (3), has been isolated, along with 15 known compounds, from the roots of Hydrangea chinensis. The structure and stereochemistry of the new alkaloid 3 was determined using extensive 2D NMR data. PMID:11473431

Patnam, R; Chang, F R; Chen, C Y; Kuo, R Y; Lee, Y H; Wu, Y C

2001-07-01

169

Alkaloids in bufonid toads (melanophryniscus): temporal and geographic determinants for two argentinian species.  

PubMed

Bufonid toads of the genus Melanophryniscus represent one of several lineages of anurans with the ability to sequester alkaloids from dietary arthropods for chemical defense. The alkaloid profile for Melanophryniscus stelzneri from a location in the province of Córdoba, Argentina, changed significantly over a 10-year period, probably indicating changes in availability of alkaloid-containing arthropods. A total of 29 alkaloids were identified in two collections of this population. Eight alkaloids were identified in M. stelzneri from another location in the province of Córdoba. The alkaloid profiles of Melanophryniscus rubriventris collected from four locations in the provinces of Salta and Jujuy, Argentina, contained 44 compounds and differed considerably between locations. Furthermore, alkaloid profiles of M. stelzneri and M. rubriventris strongly differed, probably reflecting differences in the ecosystem and hence in availability of alkaloid-containing arthropods. PMID:17333373

Daly, J W; Wilham, J M; Spande, T F; Garraffo, H M; Gil, R R; Silva, G L; Vaira, M

2007-04-01

170

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

171

Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoquinolizidine alkaloid by using a domino process.  

PubMed

The first enantioselective syntheses of the Ipecacuanha alkaloid emetine (1) and the Alangium alkaloid tubulosine (2) is described employing a domino Knoevenagel/hetero-Diels-Alder reaction and an enantioselective catalytic transfer hydrogenation of imines as key steps. Thus, hydrogenation of the imine 15 with the catalyst (R,R)-16 gives the tetrahydroisoquinoline 14 with 95 % ee which was transformed into the aldehyde (1S)-7. The three-component domino reaction of (1S)-7 with 6 and 8 led to 19, which in a second domino process was treated with K(2)CO(3) in methanol followed by a hydrogenation to give the benzoquinolizidine 4 together with the diastereomers 22 and 23 in a overall yield of 66 %. Further transformation of 4 with the amines 3 and 5 yielded enantiopure emetine (1) and tubulosine (2), respectively. In addition, starting from 19 the novel benzoquinolizidine alkaloid 34 was synthesised; this compound resembles the vallesiachotamine alkaloid dihydroantirhin 31, which has not been isolated so far but probably must also exist in nature. PMID:15195303

Tietze, Lutz F; Rackelmann, Nils; Müller, I

2004-06-01

172

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

173

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

174

Mutagenicity and recombinagenicity of Ocotea acutifolia (Lauraceae) aporphinoid alkaloids.  

PubMed

The somatic mutation and recombination test (SMART) in wing cells of Drosophila melanogaster was used to test the mutagenic and recombinogenic activities of five aporphinoid alkaloids isolated from Ocotea acutifolia: thalicminine (1), (+)-dicentrine (2), (+)-ocoteine (3), (+)-6S-ocoteine N-oxide (4), and (+)-leucoxine (5). Third-stage larvae derived from the standard cross with wing cell markers mwh and/or flr(3) were treated chronically. The frequencies of mutant spots observed in marked heterozygous descendants revealed significant dose-dependent genotoxicity for alkaloids 1-4; compounds 1 and 2 were the most active. Alkaloids 1-4 also induced mitotic recombination. The presence of a methoxyl group at C-3 (as in compound 3) lowers its genotoxic effect relative to that of unsubstituted analogue 2, and the introduction of an N-oxide functionality (3 vs. 4) further reduces genotoxicity. The very planar conformation of oxo-aporphine alkaloid 1 may account for its higher genotoxicity vs. its less-planar analogues 3 and 4. As previously reported for (+)-dicentrine (2), alkaloids 1, 3, and 4 may also be DNA intercalating agents, interfering with the catalytic activity of topoisomerases. PMID:23892138

Guterres, Zaira da Rosa; da Silva, Ana Francisca Gomes; Garcez, Walmir Silva; Garcez, Felipe Rodrigues; Fernandes, Carlos Alexandre; Garcez, Fernanda Rodrigues

2013-09-18

175

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

Microsoft Academic Search

Lupinus leucophyllus is one of many lupine species known to contain toxic and\\/or teratogenic alkaloids that can cause congenital birth defects.\\u000a The concentrations of total alkaloids and the individual major alkaloids were measured in three different years from different\\u000a plant parts over the phenological development of the plant. All of the alkaloids were found in the different plant tissues\\u000a throughout

Stephen T. Lee; Michael H. Ralphs; Kip E. Panter; Daniel Cook; Dale R. Gardner

2007-01-01

176

Cytological changes associated with alkaloid production in cultured cells of Coptis japonica and Thalictrum minus  

Microsoft Academic Search

Cell structures were compared between alkaloid-producing and non-producing cell cultures of Coptis japonica and Thalictrum minus by electron microscopic observation. In alkaloid-producing cells of C. japonica, prior to the onset of alkaloid synthesis, the vacuoles showed a greater volume than in non-producing cells. These were characterized by a number of large starch grains in the cytoplasm. Furthermore, alkaloid-producing cells contained

H. Yamamoto; K. Nakagawa; H. Fukui; M. Tabata

1986-01-01

177

Characterization of Vacuolar Transport of the Endogenous Alkaloid Berberine in Coptis japonica  

Microsoft Academic Search

Alkaloids comprise one of the largest groups of plant secondary metabolites. Many of them exhibit strong biological activities, and, in most cases, they are accumulated in the central vacuole of alkaloid-producing plants after synthesis. However, the mechanisms involved in alkaloid transport across the tonoplast are only poorly understood. In this study, we analyzed the vacuolar transport mechanism of an isoquinoline

Mihoko Otani; Nobukazu Shitan; Kyoko Sakai; Enrico Martinoia; Fumihiko Sato; Kazufumi Yazaki

2005-01-01

178

Alkaloids from bufonid toads (Melanophryniscus): decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines, and quinolizidines.  

PubMed

Skins of bufonid toads of the genus Melanophryniscus contain several classes of alkaloids: decahydroquinolines, pumiliotoxins, allopumiliotoxins, homopumiliotoxins, both 3,5- and 5,8-disubstituted indolizidines, 3,5-disubstituted pyrrolizidines, and a 1,4-disubstituted quinolizidine. Tricyclic alkaloids, including precoccinelline [193A] and alkaloid 236, an oxime methyl ether, are present in one population of Melanophryniscus stelzneri. PMID:8482947

Garraffo, H M; Spande, T F; Daly, J W; Baldessari, A; Gros, E G

1993-03-01

179

Determination of isoquinoline alkaloids contents in two Algerian species of Fumaria (Fumaria capreolata and Fumaria bastardi)  

Microsoft Academic Search

This paper describes a fast and efficient procedure to separate and identify isoquinoline alkaloids from methalonic extract of two Algerian Fumaria (Fumariacea) species (Fumaria capreolata L. and Fumaria bastardi L.) used in traditional medicine in cases of hepatobiliary disfunction and diarrhoea. Total quinolizidine alkaloid contents were 426 mg\\/100 g (F. capreolata) and 521 mg\\/100 g (F. bastardi). The isoquinoline alkaloids,

Fadila Maiza-Benabdesselam; Mohamed Chibane; Khodir Madani; Henry Max; Sandrine Adach

180

A look inside an alkaloid multisite plant: the Catharanthus logistics.  

PubMed

Environmental pressures forced plants to diversify specialized metabolisms to accumulate noxious molecules such as alkaloids constituting one of the largest classes of defense metabolites. Catharanthus roseus produces monoterpene indole alkaloids via a highly elaborated biosynthetic pathway whose characterization greatly progressed with the recent expansion of transcriptomic resources. The complex architecture of this pathway, sequentially distributed in at least four cell types and further compartmentalized into several organelles, involves partially identified inter-cellular and intra-cellular translocation events acting as potential key-regulators of metabolic fluxes. The description of this spatial organization and the inherent secretion and sequestration of metabolites not only provide new insight into alkaloid cell biology and its involvement in plant defense processes but also present new biotechnological challenges for synthetic biology. PMID:24727073

Courdavault, Vincent; Papon, Nicolas; Clastre, Marc; Giglioli-Guivarc'h, Nathalie; St-Pierre, Benoit; Burlat, Vincent

2014-06-01

181

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

182

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

PubMed Central

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

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

2013-01-01

183

Loline alkaloid gene clusters of the fungal endophyte neotyphodium uncinatum  

US Patent & Trademark Office Database

Loline alkaloids (LA), which are 1-aminopyrrolizidines with an oxygen bridge, are produced by Epichloe (anamorph=Neotyphodium) species, endophytes of grasses. LA are insecticidal, thus helping protect host plants from insect herbivory. Suppression subtractive hybridization PCR was used to isolate transcripts up-regulated during loline alkaloid production in cultures of Neotyphodium uncinatum. Subtracted cDNAs were cloned, and a .lamda.-phage cDNA library from an LA-expressing N. uncinatum culture was screened with subtracted cDNA. In BLAST searches, several cDNAs identified had sequence similarities to aspartate kinases, and another with O-acetylhomoserine-(thiol)lyase. Differential expression of these two genes in LA-producing cultures of N. uncinatum was confirmed, and in a survey of 23 isolates from 21 Neotyphodium and Epichloe species these two genes strictly correlated with LA production. Two nucleic acid molecules encoding two loline alkaloid gene clusters have been identified.

2007-02-27

184

Isolation and pharmacological activities of the Tecoma stans alkaloids.  

PubMed

Tecoma stans is a plant traditionally used in Mexico for the control of diabetes. Amongst the alkaloids isolated from the plant harvested in Egypt, Tecomine was shown to be one of the compounds responsible for the hypoglycemic action. Given the interest in substances able to treat type II diabetes, we isolated the main alkaloids present in the plant growing in Egypt and Brazil and tested them in vivo on db/db mice. Contrary to previous literature reports on different animal models, Tecomine was unable to modify glycemia; the only effect seen being a decrease in plasma cholesterol levels. On the contrary, when tested in vitro on glucose uptake in white adipocytes, the compound showed a marked effect. The two other alkaloids isolated, namely 5beta-Hydroxyskitanthine, early called Base C, and Boschniakine were inactive both in vivo and in vitro assays. PMID:13679170

Costantino, Luca; Raimondi, Laura; Pirisino, Renato; Brunetti, Tiziana; Pessotto, Pompeo; Giannessi, Fabio; Lins, Arlete Paulino; Barlocco, Daniela; Antolini, Luciano; El-Abady, Samia A

2003-09-01

185

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

186

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

187

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

188

In vitro inhibitory activities of Lauraceae aporphine alkaloids.  

PubMed

The in vitro anti-inflammatory effect of eight aporphine alkaloids isolated from the leaves of two Lauraceae plants (Pleurothyrium cinereum and Ocotea macrophylla) was evaluated through inhibition of two isozymes of cyclooxygenase (COX-1 and COX-2), 5-lipoxygenase (5-LOX), and platelet aggregation induced by PAF, AA and ADP. All alkaloids exhibited inhibitory activities against COX-2 (IC50 25.9-116 microM range) and PAF- and AA-induced platelet aggregation, while only four and three of them were good COX-1 and 5-LOX inhibitors, respectively. (+)-N-acetyl-nornantenine 6 was the most potent COX-2, 5-LOX, AA and PAF inhibitor. PMID:20420312

Coy Barrera, Ericsson David; Cuca Suárez, Luis Enrique

2010-03-01

189

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

190

Alkaloids from single skins of the Argentinian toad Melanophryniscus rubriventris (ANURA, BUFONIDAE): An unexpected variability in alkaloid profiles and a profusion of new structures.  

PubMed

GC-MS analysis of single-skins of ten Melanophryniscus rubriventris toads (five collections of two toads each) captured during their breeding season in NW Argentina has revealed a total of 127 alkaloids of which 56 had not been previously detected in any frog or toad. Included among these new alkaloids are 23 new diastereomers of previously reported alkaloids. What is particularly distinguishing about the alkaloid profiles of these ten collections is the occurrence of many of the alkaloids, whether known or new to us, in only one of the ten skins sampled, despite two skins being obtained from each breeding site of the five populations. Many of the alkaloids are of classes known to have structures with branched-chains (e.g. pumiliotoxins and tricyclic structures) that are considered to derive from dietary mites. A large number of previously reported and new alkaloids are also of unclassified structures. Only a very few 3,5-disubstituted-indolizidine or -pyrrolizidine alkaloids are observed that have a straight-chain carbon skeleton and are likely derived from ant prey. The possible relationship of these collections made during the toad's brief breeding episodes to sequestration of dietary arthropods and individual alkaloid profiles is discussed. PMID:23596558

Garraffo, H Martin; Andriamaharavo, Nirina R; Vaira, Marcos; Quiroga, María F; Heit, Cecilia; Spande, Thomas F

2012-12-01

191

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

192

Identification of pavinane alkaloids in the genera Argemone and Eschscholzia by GC-MS.  

PubMed

The genera Eschscholtzia and Argemone (Papaveraceae) represent a rich source of pavinane alkaloids, the identification of which in alkaloid extracts is generally problematic without standards. The alkaloid extracts of three Argemone and four Eschscholtzia species were analyzed using GC-MS. The alkaloids were identified based on comparison of their mass spectra with commercial libraries, with reported data in the literature and with spectra of reference compounds. A total of 23 alkaloids of six structural types (pavinane, protopine, benzylisoquinoline, benzophenanthridine, aporphine and protoberberine) were identified. The fragmentation pathway of pavinane alkaloids was used for their identification. O-Methylneocaryachine has been reported for the first time from a natural sources and the alkaloid pattern of Eschscholzia pulchella has been analyzed and described for the first time. PMID:23156990

Cahlíková, Lucie; Kucera, Radim; Host'álková, Anna; Klimes, Jirí; Opletal, Lubomír

2012-10-01

193

Indole alkaloids from the seeds of Centaurea cyanus (Asteraceae)  

Microsoft Academic Search

Preparative RP-HPLC analysis of a methanol extract of the seeds of Centaurea cyanus afforded four indole alkaloids: moschamine, cis-moschamine, centcyamine and cis-centcyamine, the latter two being new natural products. Structures of these compounds were elucidated by comprehensive spectroscopic analyses. General toxicity of the isolates was determined by Brine Shrimp Lethality bioassay.

Satyajit D Sarker; Anuszka Laird; Lutfun Nahar; Yashodharan Kumarasamy; Marcel Jaspars

2001-01-01

194

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

195

Distribution, biosynthesis and turnover of pyrrolizidine alkaloids in Cynoglossum officinale  

Microsoft Academic Search

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

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

1995-01-01

196

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

197

Synthetic Studies toward Lapidilectine-type Kopsia Alkaloids  

PubMed Central

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

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

2012-01-01

198

Cytotoxic benzophenanthridine and benzylisoquinoline alkaloids from Argemone mexicana.  

PubMed

Fractionation of the chloroform extract from the aerial part of Argemone mexicana led to the isolation of two benzophenanthridine-type alkaloids, N-demethyloxysanguinarine and pancorine; three benzylisoquinoline-type alkaloids, (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline, (+)-higenamine and (+)-reticuline. Among them, N-demethyloxysanguinarine is a new compound, and (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxy-isoquinoline was isolated form a natural source for the first time, to which was assigned a trivial name, (+)-argenaxine. In addition, six known non-alkaloidal compounds were also isolated and identified. All compounds were characterized on the basis of their spectral data and chemical evidences. Some isolated alkaloids from this species were evaluated for their cytotoxicity to human nasopharyngeal carcinoma (HONE-1) and human gastric cancer (NUGC) cell lines. Chelerythrine was found to exhibit significant activity against NUGC cell line, while angoline inhibited both types. (+)-Argenaxine showed moderate activity against the NUGC cell line. PMID:12939038

Chang, Yuh-Chwen; Chang, Fang-Rong; Khalil, Ashraf T; Hsieh, Pei-Wen; Wu, Yang-Chang

2003-01-01

199

Instrumental Analytical Techniques Used for Datura Alkaloid Analyses  

Microsoft Academic Search

In the present paper a review of the instrumental techniques used for the analysis of alkaloids in legume seeds, feedstuffs and plants is presented. The analysis is performed by chromatographic techniques. Mainly Thin Layer Chromatography (TLC), Gas Chromatography (GC) and High Performance Liguid Chromatography (HPLC) are applied.

I. N. Papadoyannis

1994-01-01

200

Indole alkaloids from the seeds of Centaurea cyanus (Asteraceae).  

PubMed

Preparative RP-HPLC analysis of a methanol extract of the seeds of Centaurea cyanus afforded four indole alkaloids: moschamine, cis-moschamine, centcyamine and cis-centcyamine, the latter two being new natural products. Structures of these compounds were elucidated by comprehensive spectroscopic analyses. General toxicity of the isolates was determined by Brine Shrimp Lethality bioassay. PMID:11454358

Sarker, S D; Laird, A; Nahar, L; Kumarasamy, Y; Jaspars, M

2001-08-01

201

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

202

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

203

Alkaloid profile of Bulgarian species from genus Senecio L.  

PubMed

Twenty-seven pyrrolizidine alkaloids were identified by a detailed phytochemical study and GC/MS analysis on twelve Bulgarian species from genus Senecio. Twenty of them are new for the corresponding species. Other six structures remain tentatively identified. PMID:12710745

Christov, Veselin; Evstatieva, Liuba

2003-01-01

204

Partition chromatography and countercurrent distribution of alkaloids of Fumaria officinalis  

Microsoft Academic Search

Component alkaloids of Fumaria officinalis were partly separated on a preprative scale by the countercurrent distribution technique, using selective solvent systems of the type chloroform\\/buffer solution and benzene\\/buffer solution, the optimal pH of the aqueous phase being estimated from paper chromatographic data. Good agreement between predicted and experimental separations and sequences of the bands was observed.

T. Wawrzynowicz; A. Waksmundzki

1968-01-01

205

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

PubMed Central

Background and Aims Previous measurements of conifer alkaloids have revealed significant variation attributable to many sources, environmental and genetic. The present study takes a complementary and intensive, common garden approach to examine genetic variation in Pinus ponderosa var. ponderosa alkaloid production. Additionally, this study investigates the potential trade-off between seedling growth and alkaloid production, and associations between topographic/climatic variables and alkaloid production. Methods Piperidine alkaloids were quantified in foliage of 501 nursery seedlings grown from seed sources in west-central Washington, Oregon and California, roughly covering the western half of the native range of ponderosa pine. A nested mixed model was used to test differences among broad-scale regions and among families within regions. Alkaloid concentrations were regressed on seedling growth measurements to test metabolite allocation theory. Likewise, climate characteristics at the seed sources were also considered as explanatory variables. Key Results Quantitative variation from seedling to seedling was high, and regional variation exceeded variation among families. Regions along the western margin of the species range exhibited the highest alkaloid concentrations, while those further east had relatively low alkaloid levels. Qualitative variation in alkaloid profiles was low. All measures of seedling growth related negatively to alkaloid concentrations on a natural log scale; however, coefficients of determination were low. At best, annual height increment explained 19·4 % of the variation in ln(total alkaloids). Among the climate variables, temperature range showed a negative, linear association that explained 41·8 % of the variation. Conclusions Given the wide geographic scope of the seed sources and the uniformity of resources in the seedlings' environment, observed differences in alkaloid concentrations are evidence for genetic regulation of alkaloid secondary metabolism in ponderosa pine. The theoretical trade-off with seedling growth appeared to be real, however slight. The climate variables provided little evidence for adaptive alkaloid variation, especially within regions. PMID:19010800

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

2009-01-01

206

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

207

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

PubMed Central

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

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

2004-01-01

208

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

209

Antiamoebic and antiplasmodial activities of alkaloids isolated from Strychnos usambarensis.  

PubMed

Seven alkaloids isolated from Strychnos usambarensis have been assessed for in vitro activities against Entamoeba histolytica and Plasmodium falciparum and for in vivo activity against Plasmodium berghei in mice. Strychnopentamine and 3',4'-dihydrousambarensine were highly active against P. falciparum in vitro, but were inactive and non-toxic against P. berghei in vivo. Usambarensine, usambarine, and 18,19-dihydrousambarine were highly active against E. histolytica in vitro, but were less active against P. falciparum in vitro. Nb-Methylusambarensine was less active against both protozoa than was usambarensine, and akagerine possessed little antiprotozoal activity. Structure-activity relationships are discussed in the context of the reported cytotoxic and pharmacological properties of these alkaloids. PMID:1775573

Wright, C W; Bray, D H; O'Neill, M J; Warhurst, D C; Phillipson, J D; Quetin-Leclercq, J; Angenot, L

1991-08-01

210

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

211

Pyrrolizidine alkaloids in medicinal plants of Mongolia, Nepal and Tibet.  

PubMed

Pyrrolizidine alkaloids (PAs) are widely distributed in many plant families. Most of them are hazardous for humans and domestic animals. PA also occur in many medicinal plants. This is of importance because in Western countries the use of plants or preparations of them is more and more increasing. Especially plants of the Traditional Chinese Medicine (TCM) have increased in popularity. Similarly, people are also focused on medicinal plants from other traditional medicines. Nowadays the Traditional Mongolian Medicine (TMM), the Traditional Nepalese Medicine (TNM), and the Tibetan System of Medicine (TSM) are becoming more and more of interest. In those countries application of those phytopharmaceutics is based on its traditional use but a scientific investigation--especially for possible toxic side-effects--is often missing. This paper gives an overview on traditionally used plants from Nepal, Mongolia and Tibet with respect to its content or its possible content of pyrrolizidine alkaloids. PMID:20099513

Roeder, E; Wiedenfeld, H

2009-11-01

212

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

213

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

Microsoft Academic Search

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

Thomas Hartmann

1994-01-01

214

Alkaloids of an Ipomoea Seed commonly known as Kaladana in Pakistan  

Microsoft Academic Search

IN an earlier paper, one of us1 reported that a sample of Kaladana seed from Pakistan contained 0.49 per cent of alkaloids, on defatted basis, calculated as elymoclavine. Lysergol constituted 53 per cent and chanoclavine 37 per cent of the total alkaloids. The alkaloids were identified by paper and thin-layer chromatography in seven different solvent systems, by behaviour in ultra-violet

Charles I. Abou-Chaar; George A. Digenis

1966-01-01

215

Allelochemical effects of ergoline alkaloids from Ipomoea parasitica on Heliothis virescens  

Microsoft Academic Search

Lysergol, elymoclavine and three other van Urk-positive alkaloids were identified by 2D chromatography in the seed extract ofIpomoea parasitica. The presence of the same ergoline alkaloids was also demonstrated in vegetative tissue ofI. parasitica. Heliothis virescens larvae reared on a diet containing an alkaloid extract ofI. parasitica showed an increase in the consumption index and a reduction in the effiency

Diego Amor-Prats; Jeffrey B. Harborne

1993-01-01

216

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

Microsoft Academic Search

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

S. Bieganowska; A. Waksmundzki

1976-01-01

217

Toxicity of pyrrolizidine alkaloids to humans and ruminants  

Microsoft Academic Search

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

Helmut Wiedenfeld; John Edgar

2011-01-01

218

Zoaramine, a zoanthamine-like alkaloid with a new skeleton.  

PubMed

Chemical investigation of an Atlantic variety of Zoanthus sp. led to the isolation of two new metabolites, zoaramine and zoarenone. Their structures were deduced by the use of NMR spectroscopy and computational calculation of (1)H and (13)C chemical shifts. The core of these novel compounds resembles the structure of norzoanthamine alkaloids, and their isolation represents an important step toward a better understanding of the biogenetic origin of this group of antiosteoporotic molecules. PMID:24831410

Cen-Pacheco, Francisco; Norte, Manuel; Fernández, José J; Daranas, Antonio Hernández

2014-06-01

219

Anti-invasive activity of alkaloids and polyphenolics in vitro  

Microsoft Academic Search

Invasiveness, the ability of certain tumour cells to migrate beyond their natural tissue boundaries, often leads to metastasis, and usually determines the fatal outcome of cancer. The need for anti-invasive agents has led us to search for possibly active compounds among alkaloids and polyphenolics. One hundred compounds were screened in an assay based on the confrontation of invasive human MCF-7\\/6

Virinder S. Parmar; Marc E. Bracke; Jan Philippe; Jesper Wengel; Subhash C. Jain; Carl E. Olsen; Kirpal S. Bisht; Nawal K. Sharma; Andy Courtens; Sunil K. Sharma; Krist'l Vennekens; Veerle Van Marck; Sanjay K. Singh; Naresh Kumar; Ajay Kumar; Sanjay Malhotra; Rajesh Kumar; Vivek K. Rajwanshi; Rajni Jain; Marc M. Mareel

1997-01-01

220

New Canthin-6-one Alkaloids from Quassia amara.  

PubMed

From the wood of QUASSIA AMARA L. (Simarubaceae) two new canthin-6-one alkaloids have been isolated and their structures determined as 3-methyl-4-methoxy-5-hydroxycanthin-2,6-dione ( 1) and 4-methoxy-5-hydroxycanthin-6-one 3-, N-oxide ( 2) by spectroscopic and chemical methods. 3-Methylcanthin-5,6-dione ( 3) has been also isolated and identified for the first time from this source. PMID:17221398

Barbetti, P; Grandolini, G; Fardella, G; Chiappini, I; Mastalia, A

1990-04-01

221

Microbial transformation of the steroidal alkaloid dictyophlebine by Rhizopus stolonifer.  

PubMed

The microbial transformation of a steroidal alkaloid, dictyophlebine (1) with Rhizopus stolonifer (ATCC 10404) afforded three oxidized metabolites 2-4. Compound 2 was found to be a new product. These metabolites were structurally characterized on the basis of modern spectroscopic techniques. Their inhibitory activity towards acetyl- and butyrylcholinesterase has been evaluated and the new product 2 has been found to be more potent than the parent compound and other metabolites. PMID:17409573

Devkota, Krishna Prasad; Choudhary, Muhammad Iqbal; Nawaz, Sarfaraz Ahmed; Lannang, Alain Meli; Lenta, Bruno Ndjakou; Fokou, Patrice Aime; Sewald, Norbert

2007-04-01

222

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

223

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

224

Thermodynamics of a series of harmine alkaloid derivatives  

Microsoft Academic Search

The enthalpies of solution in water and ethanol of a series of harmine alkaloid derivatives, harminium di(o-carborano-1,2-dimethyl)borate, harminium tosylate, harminium thiocyanate, N(2)-hydroxyharminium hydrogen sulfate, and adduct of harmine N-oxide with phthalic anhydride, were determined by isothermal\\u000a calorimetry. The standard heats of combustion, melting, and formation of these compounds were calculated by approximate methods.

Zh. K. Tukhmetova; I. M. Oskembekov; Sh. B. Kasenova; S. M. Adekenov; B. K. Kasenov; Zh. S. Nurmaganbetov

2010-01-01

225

Alkaloids from Australian frogs (Myobatrachidae): pseudophrynamines and pumiliotoxins.  

PubMed

Australian frogs of the genus Pseudophryne contain two distinct classes of alkaloids. The pseudophrynamine class (3a-prenyl pyrrolo[2,3-b]indoles) are unique to this genus of frogs of the family Myobatrachidae, while the pumiliotoxin-A class (8-hydroxy-8-methyl-6-alkylidene-1-azabicyclo[4.3.0]nonanes) also occur in dendrobatid frogs of the genera Dendrobates, Epipedobates, and Minyobates, in ranid frogs of the genus Mantella, and in bufonid toads of the genus Melanophryniscus. All seven species of Pseudophryne examined contain both classes of alkaloids. The pseudophrynamines were the predominant class in both species (Pseudophryne guentheri and Pseudophryne occidentalis) from Western Australia, while all of the eastern species (Pseudophryne australis, Pseudophryne bibronii, Pseudophryne coriacea, Pseudophryne corroboree, and Pseudophryne semimarmorata) contained significant amounts of both pseudophrynamines and pumiliotoxins. Pumiliotoxins, in particular pumiliotoxin B, were predominant in two eastern species (P. australis and a southern population of P. corroboree), while pseudophrynamines were dominant in P. bibronii, four of six populations of P. coriacea, one population of P. semimarmorata, and a northern population of P. corroboree. Structures are proposed for several new alkaloids of the pseudophrynamine class. PMID:2380714

Daly, J W; Garraffo, H M; Pannell, L K; Spande, T F; Severini, C; Erspamer, V

1990-01-01

226

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

227

Interplant alkaloid variation and Senecio vernalis toxicity in cattle.  

PubMed

Senecio vernalis and other plants containing pyrrolizidine alkaloids (PA) are implicated in the poisoning of cattle. The liver is a known target organ. In this study the content of the alkaloids senecionine (SCO), senkirkin (SKK) and seneciphyllin (SCP) and their toxic effects in cattle were studied. The content of these 3 compounds only varied by a factor of 2 within 10 plant collections at different locations in western Denmark (Jutland). However, individual alkaloids varied 3-fold, and the interplant variation for some of the PA up to 8-fold. SCO and SKK had very short half lives, 20 min and 70 min respectively. In cattle fed dried plant material corresponding to 200 and 400 g of fresh material for 10 d alanine aminotransferase, alkaline phosphatase and g-glutamyl transferase activities remained unchanged. Cattle subsequently fed fresh plant material up to 1 kg/d for 8 d also had no change in liver enzyme activities. Cattle did not show any clinical signs of poisoning, and no morphological liver changes were observed. PMID:11383654

Skaanild, M T; Friis, C; Brimer, L

2001-06-01

228

Metabolic engineering of the terpenoid indole alkaloid pathway of Catharanthus roseus hairy roots.  

E-print Network

??Catharanthus roseus is an important medicinal plant that produces a number of bioactive terpenoid indole alkaloids (TIAs). Specifically, vinblastine and vincristine and their semi-synthetic derivatives… (more)

Peebles, Christie A. M.

2008-01-01

229

Toxicity study of the main alkaloids of Datura ferox in broilers.  

PubMed

Seeds of the weed Datura ferox are frequent contaminants of raw materials used for animal feed. These seeds produce various toxic effects and contain mainly the alkaloids scopolamine and hyoscyamine. In this 3-month toxicity study, a mixture of scopolamine and hyoscyamine (98:2) was incorporated at four total alkaloid levels (1.5, 15, 75 or 150 mg/kg feed) into a control diet fed to 100 broilers. Alkaloid feeding caused significant reductions in the body weight gain of birds, especially of those fed a dose of 150 mg alkaloid/kg feed. Growth-retarding effects, however, were transient, as no changes in body weight gain were noted after 52 days of alkaloid feeding. Alkaloid-treated broilers showed no significant differences from controls with respect to the cardiac rate and breathing frequency nor in relation to plasma aspartate aminotransferase, alanine aminotransferase and alkaline phosphatase activities. In contrast, plasma leucine aminopeptidase activity was significantly reduced after 3 months in all alkaloid-fed birds. Autopsy and histological examination of tissues by light and electron microscopy revealed no pathological changes associated with alkaloid feeding. Broilers appeared generally healthy and behaved normally throughout. These data should be considered in the formulation of new, improved regulations defining the maximum allowable alkaloid content of D. ferox seeds contaminating raw materials destined for use as broiler feed. PMID:8258413

Kovatsis, A; Flaskos, J; Nikolaidis, E; Kotsaki-Kovatsi, V P; Papaioannou, N; Tsafaris, F

1993-11-01

230

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

PubMed

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

von Borstel, K; Hartmann, T

1986-02-01

231

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

232

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

NASA Astrophysics Data System (ADS)

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

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

2006-03-01

233

Diterpene alkaloids from Aconitum anthora and assessment of the hERG-inhibiting ability of Aconitum alkaloids.  

PubMed

A new norditerpene alkaloid, 10-hydroxy-8- O-methyltalatizamine (1), was isolated from the whole plant of ACONITUM ANTHORA L. besides the known isotalatizidine (2) and hetisinone (3). The structures were determined by means of HR-ESI-MS, 1D and 2D NMR spectroscopy, including ¹H-¹H COSY, NOESY, HSQC and HMBC experiments, resulting in complete ¹H and ¹³C chemical shift assignments for 1- 3, and revision of some earlier ¹³C-NMR data. The effects of the isolated compounds, together with twenty-one other ACONITUM alkaloids with different skeletal types and substitution patterns, on hERG channels were studied by the whole-cell patch clamp technique, using the QPatch-16 automated patch clamp system. At 10 µM, aconitine, 14-benzoylaconine 8- O-palmitate, songoramine, gigactonine and neolinine demonstrated significant hERG K+ channel inhibition; all other compounds exerted only low (6-21%) inhibitory activity. PMID:20862641

Forgo, Peter; Borcsa, Botond; Csupor, Dezso; Fodor, László; Berkecz, Róbert; Molnár V, Attila; Hohmann, Judit

2011-03-01

234

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

235

Perspectives of the metabolic engineering of terpenoid indole alkaloids in Catharanthus roseus hairy roots.  

PubMed

This review looks back on how the terpenoid indole alkaloid pathway and the regulatory factors in Catharanthus roseus were identified and characterized, and how metabolic engineering, including genetic engineering and metabolic profiling, was conducted based on the gained knowledge. In addition, further examination of the terpenoid indole alkaloid pathway is proposed. PMID:23576053

Zhao, Le; Sander, Guy W; Shanks, Jacqueline V

2013-01-01

236

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

237

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

238

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

239

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

PubMed Central

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

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

2014-01-01

240

Alkaloid profiles, concentration, and pools in velvet lupine (Lupinus leucophyllus) over the growing season.  

PubMed

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 phenological development of the plant. All of the alkaloids were found in the different plant tissues throughout the growing season, although their levels varied in different tissues. Concentrations of total alkaloids and the individual alkaloids varied on an annual basis and in their distribution in the different tissues. Anagyrine levels were highest in the floral tissue, lupanine and unknown F accumulated to the greatest level in the vegetative tissue, and 5,6-dehydrolupanine accumulated to the highest level in the stem. These alkaloids appear to be in a metabolically active state with the teratogenic alkaloid anagyrine accumulating to its highest level in the developing seed. The latter is, thus, the phenological stage posing the greatest danger to grazing livestock. PMID:17146716

Lee, Stephen T; Ralphs, Michael H; Panter, Kip E; Cook, Daniel; Gardner, Dale R

2007-01-01

241

An analysis of Sorghum halepense's behavior in presence of tropane alkaloids from Datura stramonium extracts  

PubMed Central

Background This study aimed to quantify the allelopathic potential of Datura stramonium (Jimson weed). Sorghum halepense (Johnsongrass) tolerance was assessed by germinating, seed and growing seedlings, dosing of photo-synthesis pigments, followed by treatment with D. stramonium extract tropane alkaloids. Results Preliminary chemical analysis of the extracts showed the presence of alkaloids. The presence of alkaloids was confirmed through HPLC–UV system analysis. Various concentrations of analytic purity alkaloids had similar effects on germination and development of S. halepense’s root systems with those of extracts from of D. stramonium. Germination was not affected by any of the tested extracts, but growth was inhibited by the presence of tropane alkaloids. Extracts had effects at higher alkaloid concentrations. Seedlings of S. halepense developed toxicity symptoms in the presence of alkaloid extracts, but the occurrence of several chlorotic and necrotic areas was noticed in the flower extract biotest. Conclusions Results show that the tested species is sensitive to alkaloids in their growth environment. This research justifies the fact that aqueous extracts from D. stramonium are adequate to the situations in which S. halepense becomes damaging. PMID:22839364

2012-01-01

242

Alkaloid Formation in Hairy Roots and Cell Suspensions of Rauwolfia serpentina Benth  

Microsoft Academic Search

Growth and alkaloid formation of hairy roots of Rauwolfia serpentina and Rauwolfia vomitoria were compared with that of well established cell suspension cultures of Rauwolfia serpentina and differentiated plants. Cell suspensions revealed clearly better growth - twice of the dry weight observed for the root culture. The hairy roots do not produce the major indole alkaloids typical for the root

Heike Falkenhagen; Inna N. Kuzovkina; Irina E. Alterman; Lubov A. Nikolaeva; Joachim Stöckigt

1993-01-01

243

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

PubMed Central

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

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

2012-01-01

244

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

245

Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives  

Microsoft Academic Search

There are three types of opiate alkaloids. First, the poppy alkaloids: morphine, codeine, thebaine, noscapine and papaverine; then, the semi-synthetic and synthetic derivatives used in therapy as antitussives and analgesics, such as pholcodine, ethylmorphine and dextromethorphan; at last narcotic compounds, diacetylmorphine (heroin) and opiates employed as substitutes in treatment of addiction: buprenorphine and methadone. For classical thin-layer chromatography (TLC) of

Jacques Pothier; Nicole Galand

2005-01-01

246

Refractory Period and Strophanthin Actions, as Influenced by Four Indole Alkaloids and Two Synthetic Azepinoindoles  

Microsoft Academic Search

The harmala alkaloids har mane and harmine, the iboga alkaloids ibogamine and tabernanthine, and two synthetic azepinoindoles prolong the functional re fractory period of isolated left guinea pig atria. Actions of k-strophanthin in vitro are modified by these drugs, e.g. concentrations for maximal inotropic action and those forcontracture or standstill are increased. Harmane and the azepinoindoles reduce the inotropic activity

G. Zetler; W. Lessau

1972-01-01

247

Polymethyleneamine Alkaloids of Animal Origin: I. Metabolites of Marine and Microbial Organisms  

Microsoft Academic Search

This review, issued in two parts, describes the information on the structure and biological activity of animal alkaloids derived from polymethyleneamines and produced by marine organisms, wasps, spiders, and microorganisms. Animal alkaloids are outstanding models for developing methods and drugs for the treatment of many human diseases. In the first part, we consider compounds produced by marine and microbial organisms.

L. N. Rogosa; N. F. Salakhutdinov; G. A. Tolstikov

2005-01-01

248

Iontophoretic release and transport of alkaloids from Catharanthus roseus cells in a ceramic hollow fiber reactor  

Microsoft Academic Search

Summary An iontophoretic device with a configuration similar to that of a single hollow fiber reactor was found to enhance the release and transport of intracellular alkaloids fromCatharanthus roseus cells. As the applied current increased from 1 to 2 milliamperes, the rate of release and transport of alkaloids almost doubled. Pretreatment of the cells with DMSO further enhanced the production.

H. T. Pu; R. Y. K. Yang; F. L. Saus

1989-01-01

249

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

250

Changes in the steroidal alkaloid solasodine during development of Solanum nigrum and Solanum incanum  

Microsoft Academic Search

All tested organs of Solanum nigrum and Solanum incanum elaborated solasodine, but the levels varied widely. In both species, the smallest leaves showed the highest alkaloid concentration. Maximum levels in S. incanum leaves were greater than twice those in S. nigrum. The absolute amount of alkaloid per leaf increased during leaf development whereas the concentration declined. The pattern of change

Elsadig A. Eltayeb; Alia S. Al-Ansari; James G. Roddick

1997-01-01

251

Optimisation of conditions for extracting pesticidal alkaloids from Cynanchum komarovii (Maxim.)  

Microsoft Academic Search

The methodology of a new OA9 (3) matrix and an analysis of variance technique were developed during the optimisation of extracting pesticidal alkaloids from Cynanchum komarovii. Many factors were found to affect the amount of alkaloids extracted: which parts of the plant were used – roots gave the highest yield; particle size of the material – highest yield when the

Zhen Congai; Guo Yanyan; Zhang Xuechang; Miao Jing; Shi Wangpeng

2012-01-01

252

Furoquinoline alkaloids isolated from Balfourodendron riedelianum as photosynthetic inhibitors in spinach chloroplasts.  

PubMed

In the search for natural inhibitors of plant growth, we investigate the mechanism of action of the natural furoquinoline alkaloids isolated from Balfourodendron riedelianum (Rutaceae): evolitrine (1), kokusaginine (2), ?-fagarine (3), skimmianine (4) and maculosidine (5) on the photosynthesis light reactions. Their effect on the electron transport chain on thylakoids was analyzed. Alkaloids 1, 2, 4 and 5 inhibited ATP synthesis, basal, phosphorylating and uncoupled electron transport acting as Hill reaction inhibitors on spinach chloroplasts. Alkaloid 3 was not active. The inhibition and interaction site of alkaloids 1, 2, 4 and 5 on the non-cyclic electron transport chain was studied by polarography and fluorescence of the chlorophyll a (Chl a). The results indicate that the target for 1 was localized on the donor and acceptor side of PS II. In addition alkaloids 2 and 5 affect the PS I electron acceptors on leaf discs. PMID:23416711

Veiga, Thiago André Moura; King-Díaz, Beatriz; Marques, Anna Sylvia Ferrari; Sampaio, Olivia Moreira; Vieira, Paulo Cezar; da Silva, Maria Fátima das Graças Fernandes; Lotina-Hennsen, Blas

2013-03-01

253

Antimicrobial and cytotoxic activity of the alkaloids of Amlaki (Emblica officinalis).  

PubMed

Alkaloids are important sources of drug that's why we have conducted our research to find out the biological activity of the alkaloids of a plant that is the Amlaki. Alkaloids were extracted from the methanolic extract of the fresh ripe fruits of Amlaki (Emblica officinalis) through solvent-solvent partitioning method with n-hexane and chloroform. The chloroform soluble fraction of the crude methanolic extract of the ripe fruits of Amlaki containing alkaloids was subjected to antimicrobial activity and brine shrimp lethality bioassay for observing cytotoxic activity. The chloroform soluble fraction of the methanolic extract exhibited significant antimicrobial activity against some Gram positive and Gram negative pathogenic bacteria and strong cytotoxicity having a LC50 of 10.257 +/- 0.770 microg mL(-1). It is concluded that the chloroform soluble fraction of the ripe fruits of Amlaki containing alkaloids are biologically active. PMID:19899327

Rahman, S; Akbor, M M; Howlader, A; Jabbar, A

2009-08-15

254

Characterization of protoberberine alkaloids in Coptidis Rhizoma (Huanglian) by HPLC with ESI-MS/MS.  

PubMed

This study aims to qualitatively analyze protoberberine alkaloids in crude extract of Coptidis Rhizoma using HPLC with ESI-MS/MS. Possible specific molecular weights of protoberberine alkaloids were firstly deduced according to literatures and were adopted to screen the alkaloids in the HPLC with ESI-MS of crude extract of Coptidis Rhizoma. As a result, 21 protoberberine alkaloids were found, including compounds of very low concentration and compounds coeluted in one peak. Among these, two compounds were positively identified and verified by comparison with standards. Ten of these compounds were first reported in this study for Coptidis Rhizoma. In addition, chromatographic retention parameters a and c of all compounds were obtained using their retention times under five gradient conditions and were applied to confirm the deduction about the structures of protoberberine alkaloids by tandem mass data. PMID:23505147

Ren, Lingling; Xue, Xingya; Liang, Xinmiao

2013-04-01

255

Structural elucidation and identification of alkaloids in Rhizoma Coptidis by electrospray ionization tandem mass spectrometry.  

PubMed

Simple, convenient, sensitive and accurate analytical methods are needed for the structural characterization and identification of alkaloid components in Rhizoma Coptidis in traditional Chinese herbal medicine, which has important bioactivity. In this work, the identification of alkaloid compounds in Rhizoma Coptidis was investigated by obtaining molecular mass information using electrospray ionization mass spectrometry (ESI-MS). Multi-stage tandem mass spectrometric (ESI-MS(n)) data for the alkaloid compounds were used for detailed structural characterization, then structure information was obtained by comparison of the fragmentation mechanisms of both alkaloids in Rhizoma Coptidis and standard samples of berberine, palmatine, coptisine and jatrorrhizine by MS. Based on the results obtained, the structure of a novel compound was elucidated. The results of the experiments demonstrate that ESI-MS(n) is a sensitive, selective and effective tool for the rapid determination of alkaloids in Rhizoma Coptidis. PMID:15532075

Wang, Daowu; Liu, Zhiqiang; Guo, Mingquan; Liu, Shuying

2004-11-01

256

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

257

Aaptamines, marine spongean alkaloids, as anti-dormant mycobacterial substances.  

PubMed

A new aaptamine class alkaloid, designated 2-methoxy-3-oxoaaptamine (1), together with seven known aaptamines (2-8) were isolated from a marine sponge of Aaptos sp. as anti-mycobacterial substances against active and dormant bacilli. The chemical structure of 1 was determined on the basis of spectroscopic analysis. Compound 1 was anti-mycobacterial against Mycobacterium smegmatis in both active growing and dormancy-inducing hypoxic conditions with a minimum inhibitory concentration (MIC) of 6.25 ?g/ml, and compounds 2, 5, 6, and 7 showed anti-mycobacterial activities under hypoxic condition selectively, with MIC values of 1.5-6.25 ?g/ml. PMID:24414399

Arai, Masayoshi; Han, Chisu; Yamano, Yoshi; Setiawan, Andi; Kobayashi, Motomasa

2014-04-01

258

Evaluation of pyridoacridine alkaloids in a zebrafish phenotypic assay.  

PubMed

Three new minor components, the pyridoacridine alkaloids 1-hydroxy-deoxyamphimedine (1), 3-hydroxy-deoxyamphimedine (2), debromopetrosamine (3), and three known compounds, amphimedine (4), neoamphimedine (5) and deoxyamphimedine (6), have been isolated from the sponge Xestospongia cf. carbonaria, collected in Palau. Structures were assigned on the basis of extensive 1D and 2D NMR studies as well as analysis by HRESIMS. Compounds 1-6 were evaluated in a zebrafish phenotype-based assay. Amphimedine (4) was the only compound that caused a phenotype in zebrafish embryos at 30 muM. No phenotype other than death was observed for compounds 1-3, 5, 6. PMID:20631869

Wei, Xiaomei; Bugni, Tim S; Harper, Mary Kay; Sandoval, Imelda T; Manos, Elizabeth J; Swift, Jennifer; Van Wagoner, Ryan M; Jones, David A; Ireland, Chris M

2010-01-01

259

The alkaloid of Acacia berlandieri, N-methyl-B-phenylethylamine  

E-print Network

LfSRARY * A M LfSSRAR fY NR-ME LfS RAYRAN-M NE RTRT-R HSXARPM-SX-B N-METHXL-S-PHBNTLETHYLAMIKB A Dissertation B.y Bennie Joe Camp Submitted to the Graduate School of the Agricultural and Mechanical College of Texas in partial fulfillment... of the requirements for the degree of DOCTOR OF PHILOSOPHY August 1956 Major Subject: Biochemistry and Nutrition ?THE ALKALOID OF ACACIA BEKLAflD IER I, N-METHYL-[3 -PHEBYLETHILAM IEE A Dissertation 3y Bennie Joe Camp August 1956 ACKNOWLEDGMENTS The author...

Camp, Bennie Joe

2013-10-04

260

Acridone alkaloids from Glycosmis chlorosperma as DYRK1A inhibitors.  

PubMed

Two new acridone alkaloids, chlorospermines A and B (1 and 2), were isolated from the stem bark of Glycosmis chlorosperma, together with the known atalaphyllidine (3) and acrifoline (4), by means of bioguided isolation using an in vitro enzyme assay against DYRK1A. Acrifoline (4) and to a lesser extent chlorospermine B (2) and atalaphyllidine (3) showed significant inhibiting activity on DYRK1A with IC50's of 0.075, 5.7, and 2.2 ?M, respectively. Their selectivity profile was evaluated against a panel of various kinases, and molecular docking calculations provided structural details for the interaction between these compounds and DYRK1A. PMID:24798019

Beniddir, Mehdi A; Le Borgne, Erell; Iorga, Bogdan I; Loaëc, Nadège; Lozach, Olivier; Meijer, Laurent; Awang, Khalijah; Litaudon, Marc

2014-05-23

261

Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence.  

PubMed

Iteamine, o-aminobenzyl ?-D-glucopyranoside, is the first alkaloid to be isolated from Itea virginica. Itea is the sole plant source of D-psicose, a rare sugar likely to be a major dietary supplement. The structure of iteamine was established by NMR and confirmed by total synthesis. Iteamine and its galacto-analog (which was not found in Itea plants) showed no strong inhibition of any of the 15 glycosidases tested; unnatural galacto-iteamine was a weak inhibitor of chicken liver ?-N-acetylgalactosaminidase. PMID:24534106

Ayers, Benjamin J; Hollinshead, Jacqueline; Saville, Alexander W; Nakagawa, Shinpei; Adachi, Isao; Kato, Atsushi; Izumori, Ken; Bartholomew, Barbara; Fleet, George W J; Nash, Robert J

2014-04-01

262

Indole alkaloids with new skeleton activating neural stem cells.  

PubMed

Alstoscholarisines A-E (1-5), five unprecedented monoterpenoid indole alkaloids with 6/5/6/6/6 fused-bridge rings, were isolated from Alstonia scholaris. They promoted adult neuronal stem cells (NSCs) proliferation significantly, in which the most active one (1) functioned from a concentration of 0.1 ?g/mL in a dosage-dependent manner. Furthermore, 1 enhanced NSC sphere formation and neurogenic fate commitment through activation of a Wnt signaling pathway and promoted NSC differentiation but did not affect proliferation of neuroblastoma cells. PMID:25353160

Yang, Xing-Wei; Yang, Cui-Ping; Jiang, Li-Ping; Qin, Xu-Jie; Liu, Ya-Ping; Shen, Qiu-Shuo; Chen, Yong-Bin; Luo, Xiao-Dong

2014-11-01

263

A New Prenylated Indole Diketopiperazine Alkaloid from Eurotium cristatum.  

PubMed

A new prenylated indole diketopiperazine alkaloid, cristatumin F (1), and four known metabolites, echinulin (2), dehydroechinulin (3), neoechinulin A (4) and variecolorin O (5), were isolated from the crude extract of the fungus Eurotium cristatum. The structure of 1 was elucidated primarily by NMR and MS methods. The absolute configuration of 1 was assigned using Marfey's method applied to its acid hydrolyzate. Cristatumin F (1) showed modest radical scavenging activity against DPPH radicals, and exhibited marginal attenuation of 3T3L1 pre-adipocytes. PMID:25372398

Zou, Xianwei; Li, Ying; Zhang, Xiaona; Li, Qian; Liu, Xuan; Huang, Yun; Tang, Tao; Zheng, Saijing; Wang, Weimiao; Tang, Jintian

2014-01-01

264

New semisynthetic vinca alkaloids: chemical, biochemical and cellular studies  

Microsoft Academic Search

A new semisynthetic anti-tumour bis-indol compound, KAR-2 [3?-(?-chloroethyl)-2?,4?-dioxo-3,5?-spiro-oxazolidino-4-deacetoxy-vinblastine] with lower toxicity than vinca alkaloids used in chemotherapy binds to calmodulin but, in contrast to vinblastine, does not exhibit anti-calmodulin activity. To investigate whether the modest chemical modification of bis-indol structure is responsible for the lack of anti-calmodulin potency and for the different pharmacological effects, new derivatives have been synthesized for

F Orosz; B Comin; B Raïs; J Puigjaner; J Kovács; G Tárkányi; T Ács; T Keve; M Cascante; J Ovádi

1999-01-01

265

Numerical Algorithms  

NSDL National Science Digital Library

CSC 325. (MAT 325) Numerical Algorithms (3) Prerequisite: CSC 112 or 121, MAT 162. An introduction to the numerical algorithms fundamental to scientific computer work. Includes elementary discussion of error, polynomial interpolation, quadrature, linear systems of equations, solution of nonlinear equations and numerical solution of ordinary differential equations. The algorithmic approach and the efficient use of the computer are emphasized.

Tagliarini, Gene

2003-04-21

266

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

PubMed

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

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

2014-03-01

267

Biosynthetic pathway of terpenoid indole alkaloids in Catharanthus roseus.  

PubMed

Catharanthus roseus is one of the most extensively investigated medicinal plants, which can produce more than 130 alkaloids, including the powerful antitumor drugs vinblastine and vincristine. Here we review the recent advances in the biosynthetic pathway of terpenoid indole alkaloids (TIAs) in C. roseus, and the identification and characterization of the corresponding enzymes involved in this pathway. Strictosidine is the central intermediate in the biosynthesis of different TIAs, which is formed by the condensation of secologanin and tryptamine. Secologanin is derived from terpenoid (isoprenoid) biosynthetic pathway, while tryptamine is derived from indole biosynthetic pathway. Then various specific end products are produced by different routes during downstream process. Although many genes and corresponding enzymes have been characterized in this pathway, our knowledge on the whole TIA biosynthetic pathway still remains largely unknown up to date. Full elucidation of TIA biosynthetic pathway is an important prerequisite to understand the regulation of the TIA biosynthesis in the medicinal plant and to produce valuable TIAs by synthetic biological technology. PMID:25159992

Zhu, Xiaoxuan; Zeng, Xinyi; Sun, Chao; Chen, Shilin

2014-09-01

268

Antiplasmodial alkaloids from the bark of Cryptocarya nigra (Lauraceae).  

PubMed

A dichloromethane extract of the stem bark of Cryptocarya nigra showed strong in vitro inhibition of Plasmodium falciparum growth, with an IC50 value of 2.82 ?g/mL. The phytochemical study of this extract has led to the isolation and characterization of four known alkaloids: (+)-N-methylisococlaurine (1), atherosperminine (2), 2-hydroxyathersperminine (3), and noratherosperminine (4). Structural elucidation of all alkaloids was accomplished by means of high field 1D- and 2D-NMR, IR, UV and LCMS spectral data. The isolated extract constituents (+)-N-methylisococlaurine (1), atherosperminine (2) and 2-hydroxy-atherosperminine (3) showed strong antiplasmodial activity, with IC50 values of 5.40, 5.80 and 0.75 ?M, respectively. In addition, (+)-N-methylisocolaurine (1) and atherosperminine (2) showed high antioxidant activity in a DPPH assay with IC50 values of 29.56 ug/mL and 54.53 ug/mL respectively. Compounds 1 and 2 also both showed high antioxidant activity in the FRAP assay, with percentages of 78.54 and 70.66 respectively and in the metal chelating assay, with IC50 values of 50.08 ug/mL and 42.87 ug/mL, respectively. PMID:23884132

Nasrullah, Ayu Afiqah; Zahari, Azeana; Mohamad, Jamaludin; Awang, Khalijah

2013-01-01

269

New polyhydroxylated pyrrolidine, piperidine, and pyrrolizidine alkaloids from Scilla sibirica.  

PubMed

Chromatographic separation of an extract of the bulbs of Scilla sibirica resulted in the isolation of five pyrrolidines, two pyrrolidine glycosides, six piperidines, one piperidine glycoside, and eight pyrrolizidines. 2,5-Dideoxy-2,5-imino-glycero-d-manno-heptitol (homoDMDP, 1) is a common alkaloid in all plants of the Hyacinthaceae examined to date and was also found in S. sibirica. The structures of the new alkaloids were elucidated by spectroscopic methods as 7-deoxy-homoDMDP (4), 2,5-dideoxy-2,5-imino-glycero-d-galacto-heptitol (5), the 4-O-beta-d-mannoside (6) and the 4-O-beta-d-mannobioside (7) of 6-deoxy-homoDMDP (2), 7-deoxyhomonojirimycin (12), 7-deoxyhomomannojirimycin (13), and polyhydroxypyrrolizidines, hyacinthacines A(4) (15), A(5) (16), A(6) (17), A(7) (18), B(4) (20), B(5) (21), and B(6) (22). HomoDMDP (1) is a potent inhibitor of beta-glucosidase and beta-galactosidase, while 6-deoxy-homoDMDP (2) showed significantly less inhibition. However, 7-deoxygenation of 1, leading to 4, showed no effect on the inhibitory activity toward both enzymes. Although 2 is not an inhibitor of alpha-l-fucosidase, the monomannoside of 2 shows inhibitory activity toward alpha-l-fucosidase. Elongation of the beta-mannopyranosyl chain of 6 to give 7 enhanced the inhibitory activity. PMID:12502331

Yamashita, Toru; Yasuda, Kayo; Kizu, Haruhisa; Kameda, Yukihiko; Watson, Alison A; Nash, Robert J; Fleet, George W J; Asano, Naoki

2002-12-01

270

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

271

Hepatotoxic pyrrolizidine alkaloids in pollen and drying-related implications for commercial processing of bee pollen.  

PubMed

Using HPLC-ESI-MS, several saturated and 1,2-dehydropyrrolizidine alkaloids were detected, mainly as their N-oxides, in fresh pollen collected from flowers of the pyrrolizidine alkaloid-producing plants Echium vulgare, E. plantagineum, Senecio jacobaea, S. ovatus, and Eupatorium cannabinum, and/or pollen loads from bees (bee pollen) that foraged on those plants. A major alkaloidal metabolite in S. ovatus was tentatively identified, using its mass spectrometric data and biogenic considerations, as the previously unreported, saturated alkaloid, 2-hydroxysarracine. Heating had very little effect on the 1,2-dehydropyrrolizidine alkaloids and their N-oxides from a variety of sources. Considered in conjunction with international concerns about the adverse effects of these alkaloids, the results strongly indicate a need for monitoring pollen supplies intended for human consumption, at least until conditions for processing and/or selection are clearly defined such as to significantly reduce the hepatotoxic (and potentially carcinogenic and genotoxic) pyrrolizidine alkaloid content of bee pollen. PMID:18553916

Boppré, Michael; Colegate, Steven M; Edgar, John A; Fischer, Ottmar W

2008-07-23

272

Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives.  

PubMed

There are three types of opiate alkaloids. First, the poppy alkaloids: morphine, codeine, thebaine, noscapine and papaverine; then, the semi-synthetic and synthetic derivatives used in therapy as antitussives and analgesics, such as pholcodine, ethylmorphine and dextromethorphan; at last narcotic compounds, diacetylmorphine (heroin) and opiates employed as substitutes in treatment of addiction: buprenorphine and methadone. For classical thin-layer chromatography (TLC) of opium alkaloids, it is necessary to use complex eluents with strong alkaline substances to obtain a clean separation between morphinan and isoquinoline compounds. This study purposes the planar chromatographic analysis of these substances by the automated multiple development (AMD) compared with results obtained by classical TLC method. The aim of this work was to achieve the best separation of these opiate alkaloids and derivatives by this modern technique of planar chromatography. The AMD system provided a clean separation for each of three opiates groups studied and the best results have been obtained with universal gradient: methanol 100, methanol-dichloromethane 50/50, dichloromethane 100, dichloromethane 100, hexane 100 for opium alkaloids and with gradient A: 5% of 28% ammonia in methanol 100, acetone 100, acetone 100, ethyl acetate-dichloromethane 50/50, dichloromethane 100 for antitussives and substitutes. Two reagents were used for the detection of alkaloids by spraying: Dragendorff and iodoplatinate reagents. The detection limits with these two reagents were 1 microg for ethylmorphine, thebaine, papaverine, codeine, and 2 microg for morphine and noscapine and other alkaloids. PMID:16008057

Pothier, Jacques; Galand, Nicole

2005-07-01

273

Rapid selective screening and determination of ephedrine alkaloids using GC-MS footnote mark.  

PubMed

Ephedra (ma huang) has been widely used as an herb or herbal extract in both traditional Chinese medicine and Western world dietary supplements. The effects of Ephedra have been attributed to a series of six ephedrine alkaloids including ephedrine and pseudoephedrine. A GC-MS method for the ephedrine alkaloids is described which couples ammoniacal chloroform as the extraction solvent with a two-stage derivatisation scheme. This scheme produces the O-trimethylsilyl, N-trifluoracetyl derivatives (O-TMS, N-TFA) for the primary and secondary amine alkaloids, and the O-TMS derivatives for the tertiary amine alkaloids. Relatively clean extracts are obtained from complex matrices, and the six ephedrine alkaloids are effectively separated and identified. This approach was also evaluated for quantitative analysis, and was shown to provide quantitative results for ephedrine and pseudoephedrine, and good estimates for the four minor alkaloids. Figures of merit are presented for linearity, detection limits, precision and accuracy. We have applied this approach to the rapid screening and profiling of the ephedrine alkaloids in whole Ephedra plants, liquid plant extracts, dried powder plant extracts and a variety of Ephedra-containing dietary supplements. PMID:17879230

Ranieri, Tracy L; Ciolino, Laura A

2008-01-01

274

Variability for the presence of pyrrolizidine alkaloids in Crotolaria juncea L.  

PubMed

Sunn hemp (Crotalaria juncea L.) is the most widely grown legume used as green manure in the tropics where it is also grown as a fiber and animal fodder crop. It has been reported that sunn hemp seeds contain several pyrrolizidine alkaloids that when ingested in sufficient amount can be toxic to animals and birds. No information is available regarding variability for the presences of the different types of pyrrolizidine alkaloids in the seeds. The objective of this research was to analyze sunn hemp seeds of nine populations that originated in different parts of the world for several pyrrolizidine alkaloids to determine their level of variability for the presence of these compounds and to quantify the total amount of pyrrolizidine alkaloids in the seeds. Of the nine pyrrolizidine alkaloids tested, the sunn hemp populations only had junceine and trichodesmine. PI 207657 had very low levels of both alkaloids and PI 314239, PI 322377, PI 346297, and the US cultivar Tropic Sun had very low levels of trichodesmine. Although juncein was present in higher amounts than trichodesmine in the seeds of most accessions, its value was deemed to be small. The amount of pyrrolizidine alkaloids present in the sunn hemp populations studied was low. PMID:16124407

Ji, Xiuhong; Khan, I; Mosjidis, J A; Wang, Hui; Livant, P

2005-08-01

275

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

276

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

277

Structure-activity relationship of benzophenanthridine alkaloids from Zanthoxylum rhoifolium having antimicrobial activity.  

PubMed

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

278

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

PubMed Central

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

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

2013-01-01

279

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, Andreia 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

280

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

281

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

282

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

283

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

PubMed

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

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

2014-02-01

284

Antitrypanosomal Quinoline Alkaloids from the Roots of Waltheria indica.  

PubMed

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

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

2014-10-24

285

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

PubMed

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

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

2014-11-01

286

Pyrrolizidine alkaloids from Anchusa strigosa and their antifeedant activity.  

PubMed

The pyrrolizidine alkaloid (PA) content of flowers, leaves, and roots of Anchusa strigosa (Boraginaceae) was analysed by ESI-LC-MS. Six PAs, including two new natural compounds, were detected, characterized by NMR spectroscopy, and quantified in each plant organ. The results indicated that the highest total concentration of PAs was in the leaves (23.63 mg/g of dried part), followed by the flowers (19.77 mg/g), and finally by the roots (1.80 mg/g). All PAs isolated were subjected to Spodoptera exigua and Pieris brassicae larvae. Feeding activity by both herbivore species using a bioassay was inhibited up to circa 75% depending on PA and applied concentration. PMID:15963543

Siciliano, Tiziana; Leo, Marinella De; Bader, Ammar; Tommasi, Nunziatina De; Vrieling, Klaas; Braca, Alessandra; Morelli, Ivano

2005-07-01

287

Occurrence of skin alkaloids in non-dendrobatid frogs from Brazil (Bufonidae), Australia (Myobatrachidae) and Madagascar (Mantellinae).  

PubMed

Several taxa of small frogs from the southern hemisphere contain alkaloids similar or identical to compounds previously known only from neotropical poison frogs of the family Dendrobatidae. Skin of the Brazilian toad Melanophryniscus moreirae (family Bufonidae) contains a new alkaloid 8-hydroxy-8-methyl-6-(5'-hydroxy-2'-methyl-hexylidene)-1-azabicycl o-[4.3.0] nonane (C16H29NO2), which is designated pumiliotoxin 267C. Such a structure is typical of the pumiliotoxin-A class of dendrobatid alkaloids. Melanophyryniscus moreirae contains smaller quantities of an alkaloid (C19H33NO3) identical in chromatographic and mass spectral properties to the dendrobatid alkaloid allopumiliotoxin 323B. Allopumiliotoxin 323B and an isomer of 267C occur with unidentified alkaloids in skin of the Australian frog Pseudophryne semimarmorata (family Myobatrachidae) and also in the skin of the Madagascan frog Mantella aurantiaca (family Ranidae, subfamily Mantellinae). In addition to new compounds, Mantella aurantiaca and M. madagascariensis also contain other alkaloids (e.g. histrionicotoxin and pumiliotoxin B) that were known previously only in dendrobatid frogs. Such alkaloids have not been detected in a phylogenetically wide array of other anuran amphibians, and the dendrobatid alkaloids thus become an evolutionary enigma. Certain of these compounds may have arisen convergently from new biosynthetic pathways in several families of frogs, or these alkaloids may represent parallel expression of shared-primitive pathways that are unexpressed or lost in related frogs. PMID:6523513

Daly, J W; Highet, R J; Myers, C W

1984-01-01

288

Biosynthesis and Accumulation of Ergoline Alkaloids in a Mutualistic Association between Ipomoea asarifolia (Convolvulaceae) and a Clavicipitalean Fungus1  

PubMed Central

Ergoline alkaloids occur in taxonomically unrelated taxa, such as fungi, belonging to the phylum Ascomycetes and higher plants of the family Convolvulaceae. The disjointed occurrence can be explained by the observation that plant-associated epibiotic clavicipitalean fungi capable of synthesizing ergoline alkaloids colonize the adaxial leaf surface of certain Convolvulaceae plant species. The fungi are seed transmitted. Their capacity to synthesize ergoline alkaloids depends on the presence of an intact differentiated host plant (e.g. Ipomoea asarifolia or Turbina corymbosa [Convolvulaceae]). Here, we present independent proof that these fungi are equipped with genetic material responsible for ergoline alkaloid biosynthesis. The gene (dmaW) for the determinant step in ergoline alkaloid biosynthesis was shown to be part of a cluster involved in ergoline alkaloid formation. The dmaW gene was overexpressed in Saccharomyces cerevisiae, the encoded DmaW protein purified to homogeneity, and characterized. Neither the gene nor the biosynthetic capacity, however, was detectable in the intact I. asarifolia or the taxonomically related T. corymbosa host plants. Both plants, however, contained the ergoline alkaloids almost exclusively, whereas alkaloids are not detectable in the associated epibiotic fungi. This indicates that a transport system may exist translocating the alkaloids from the epibiotic fungus into the plant. The association between the fungus and the plant very likely is a symbiotum in which ergoline alkaloids play an essential role. PMID:18344419

Markert, Anne; Steffan, Nicola; Ploss, Kerstin; Hellwig, Sabine; Steiner, Ulrike; Drewke, Christel; Li, Shu-Ming; Boland, Wilhelm; Leistner, Eckhard

2008-01-01

289

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

290

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

PubMed Central

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

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

2012-01-01

291

10'-Hydroxyusambarensine, a new antimalarial bisindole alkaloid from the roots of Strychnos usambarensis.  

PubMed

Reinvestigation of Strychnos usambarensis Gilg resulted in the isolation of a tertiary phenolic bisindole alkaloid, 10'-hydroxyusambarensine (1), which was identified by detailed spectroscopic methods. Compound 1 was moderately active against two strains of Plasmodium falciparum in vitro. PMID:10217724

Frédérich, M; Tits, M; Hayette, M P; Brandt, V; Penelle, J; DeMol, P; Llabrès, G; Angenot, L

1999-04-01

292

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

PubMed

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

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

2014-11-01

293

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, Julian

2008-01-01

294

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

295

Dimerization of functional pyrroloindolizines for the synthesis of complex myrmicarin alkaloids  

E-print Network

The union of functionalized pyrroloindolizines for the synthesis of heterodimeric products relevant to myrmicarin alkaloids is described. Design and synthesis of tricyclic substrates and new methods for their union enable ...

Ondrus, Alison E.

296

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

E-print Network

, oripavine, hydrocodone, and oxycodone) were subjected to fermentations with six fungal strains that palladium-catalyzed demethylations seemed to be limited to hydrocodone and a few tropane- type alkaloids

Hudlicky, Tomas

297

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

298

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

299

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

PubMed

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 Melanophryniscus cupreuscapularis) from similar habitats in the Corrientes/Chaco Provinces of Argentina have similar profiles of alkaloids, which differ considerably in 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 M; Baldo, J Diego; Faivovich, Julián

2008-12-15

300

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

301

Induction of micronuclei by alkaloids extracted from Senecio brasiliensis and stored for 23 years.  

PubMed

In the present study, we report the results of an investigation on pyrrolizidine alkaloids extracted from Senecio brasiliensis (Sprengel) Less., which were stored for more than 23 years under variable conditions of temperature and humidity and exposed to light. Both the crude alkaloid (integerrimine+retrorsine+impurities) and pure integerrimine conserved the ability to induce acute toxicity in mice, leading to the death of the animals in less than 24h. The alkaloids also conserved the potential to induce significant increases in micronucleus frequencies in polychromatic erythrocytes of mouse bone marrow compared to the negative control. The administration of alkaloids to lymphocyte cultures blocked with cytochalasin-B showed no significant increase in micronucleus frequency in binucleated cells, probably due to the lack of a metabolic activation mechanism. However, an antimitotic effect was observed. PMID:11943607

Santos-Mello, R; Deimlimg, L I; Lauer Júnior, C M; Almeida, A

2002-04-26

302

Structural elucidation and NMR assignments of a new pyrrolizidine alkaloid from Crotalaria vitellina Ker Gawl.  

PubMed

A new pyrrolizidine alkaloid, named crotavitelin, was isolated from fruits of Crotalaria vitellina, Fabaceae (Papilionoideae). The structure was established by spectroscopic techniques such as one-dimensional and two-dimensional NMR, IR, and MS. PMID:23716472

Casimiro Bezerra, Denise Aline; Fechine Tavares, Josean; dos Santos, Paula Ferreira; Castello Branco, Marianna Vieira Sobral; de Fátima Agra, Maria; Subrinho, Fernanda Lima; Braz-Filho, Raimundo; da Silva, Marcelo Sobral

2013-08-01

303

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

304

Indole alkaloid production by transformed and non-transformed root cultures of Catharanthus roseus  

Microsoft Academic Search

Summary  Ten transformed and two non-transformed root lines ofCatharanthus roseus were established. A systematic study of the growth kinetics and alkaloid content was performed over a culture cycle and showed\\u000a significant differences between transformed and non-transformed cultures. Mean doubling times for transformed and normal root\\u000a lines were 2.8 and 19.5 days, respectively. Alkaloid content in hairy roots was from two- to

R. Ciau-Uitz; M. L. Miranda-Ham; J. Coello-Coello; B. Chí; L. M. Pacheco; V. M. Loyola-Vargas

1994-01-01

305

In Vitro Activities of Strychnos Alkaloids and Extracts against Plasmodium falciparum  

PubMed Central

The in vitro antimalarial activities of 46 alkaloids and extracts from Strychnos species were evaluated. Two types of quasidimeric alkaloids exhibit high and selective activities against Plasmodium. Strychnopentamine and isostrychnopentamine were active against chloroquine-sensitive and -resistant strains (50% inhibitory concentration [IC50] ? 0.15 ?M), while dihydrousambarensine exhibited a 30-fold higher activity against the chloroquine-resistant strain (IC50 = 0.03 ?M) than it did against the chloroquine-sensitive strain. PMID:10471592

Frederich, Michel; Hayette, Marie-Pierre; Tits, Monique; De Mol, Patrick; Angenot, Luc

1999-01-01

306

Qualitative determination of indole alkaloids, triterpenoids and steroids of Tabernaemontana hilariana  

Microsoft Academic Search

This paper reports the separation and identification of indole alkaloids, steroids and triterpenoids from the ethanolic extracts of Tabernaemontana hilariana (Apocynaceae). The alkaloidal fractions from the ethanolic extracts obtained (root barks, green fruits, ripe fruits and seeds) were fractionated and analysed by thin-layer chromatography, capillary gas chromatography–flame ionization detection (cGC–FID) as well as by high-resolution gas chromatography–mass spectrometry (HRGC–MS). 3-Hydroxycoronaridine,

Cláudia A. L Cardoso; Wagner Vilegas; Neli K Honda

1998-01-01

307

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

308

New alkaloids from Capparis spinosa: Structure and X-ray crystallographic analysis  

Microsoft Academic Search

Fruits of Capparis spinosa contain a significant amount of compounds with many health benefits. Three new alkaloids, capparisine A (1), capparisine B (2), capparisine C (3), and two known alkaloids, 2-(5-hydroxymethyl-2-formylpyrrol-1-yl) propionic acid lactone (4), and N-(3?-maleimidy1)-5-hydroxymethyl-2-pyrrole formaldehyde (5) were isolated from the fruits of C. spinosa L. The five compounds were purified by solvent separation, column chromatography, and preparative

Tao Yang; Chang-hong Wang; Gui-xin Chou; Tao Wu; Xue-mei Cheng; Zheng-tao Wang

2010-01-01

309

Cell Type-Specific Localization of Transcripts Encoding Nine Consecutive Enzymes Involved in Protoberberine Alkaloid Biosynthesis  

PubMed Central

Molecular clones encoding nine consecutive biosynthetic enzymes that catalyze the conversion of l-dopa to the protoberberine alkaloid (S)-canadine were isolated from meadow rue (Thalictrum flavum ssp glaucum). The predicted proteins showed extensive sequence identity with corresponding enzymes involved in the biosynthesis of related benzylisoquinoline alkaloids in other species, such as opium poppy (Papaver somniferum). RNA gel blot hybridization analysis showed that gene transcripts for each enzyme were most abundant in rhizomes but were also detected at lower levels in roots and other organs. In situ RNA hybridization analysis revealed the cell type–specific expression of protoberberine alkaloid biosynthetic genes in roots and rhizomes. In roots, gene transcripts for all nine enzymes were localized to immature endodermis, pericycle, and, in some cases, adjacent cortical cells. In rhizomes, gene transcripts encoding all nine enzymes were restricted to the protoderm of leaf primordia. The localization of biosynthetic gene transcripts was in contrast with the tissue-specific accumulation of protoberberine alkaloids. In roots, protoberberine alkaloids were restricted to mature endodermal cells upon the initiation of secondary growth and were distributed throughout the pith and cortex in rhizomes. Thus, the cell type–specific localization of protoberberine alkaloid biosynthesis and accumulation are temporally and spatially separated in T. flavum roots and rhizomes, respectively. Despite the close phylogeny between corresponding biosynthetic enzymes, distinct and different cell types are involved in the biosynthesis and accumulation of benzylisoquinoline alkaloids in T. flavum and P. somniferum. Our results suggest that the evolution of alkaloid metabolism involves not only the recruitment of new biosynthetic enzymes, but also the migration of established pathways between cell types. PMID:15722473

Samanani, Nailish; Park, Sang-Un; Facchini, Peter J.

2005-01-01

310

Antiprostate cancer activity of a ß-carboline alkaloid enriched extract from Rauwolfia vomitoria  

Microsoft Academic Search

The tropical shrub, Rauwolfia vomitoria, is a medicinal plant used traditionally to treat a variety of ailments. A bioactive ß-carboline alkaloid, alstonine, present in this extract was previously shown to have anti-cancer activity against cancer cell lines. This study considers the potential anti-prostate cancer activity of this extract in vitro and in vivo. Rauwolfia vomitoria extract standardized for ß-carboline alkaloids

D. L. BEMIS; J. L. CAPODICE; P. GORROOCHURN; A. E. KATZ; R. BUTTYAN

311

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

312

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

E-print Network

and makes them water soluble. The acidic aqueous extract is then made basic, usually with ammonium hydroxide, deprotonating the basic alkaloids and allowing them to partition into non-polar solvents. Evaporation of the solvent yields a residue which can..., making the sample unsuitable for HPLC analysis. Steps to selectively remove these very non-polar compounds without prematurely removing the alkaloids of interest must be taken when analyzing tissue cultures. The objective of this investigation...

Galewsky, Samuel

2012-06-07

313

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

314

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

315

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

316

Discovery and application of doubly quaternized cinchona-alkaloid-based phase-transfer catalysts.  

PubMed

We report the discovery of novel N,N'-disubstituted cinchona alkaloids as efficient phase-transfer catalysts for the assembly of stereogenic quaternary centers. In comparison to traditional cinchona-alkaloid-based phase-transfer catalysts, these new catalysts afford substantial improvements in enantioselectivity and reaction rate for intramolecular spirocyclization reactions with catalyst loadings as low as 0.3?mol% under mild conditions. PMID:24961909

Xiang, Bangping; Belyk, Kevin M; Reamer, Robert A; Yasuda, Nobuyoshi

2014-08-01

317

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

318

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

319

Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography  

Microsoft Academic Search

A novel fast megabore capillary gas chromatographic (MCGC) method for analysis of 7 nicotine related alkaloids in tobacco and cigarette smoke, including nicotine, nornicotine, myosmine, nicotyrine, anabasine, anatabine and 2,3-dipyridyl, was developed. The use of megabore capillary column GC methodology, equipped with flame ionization detector (FID), provided rapid, unambiguous nicotine related alkaloids analysis. One gram flue-cured tobacco (or Cambridge filter

Jibao Cai; Baizhan Liu; Ping Lin; Qingde Su

2003-01-01

320

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

321

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

322

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

323

Chemical composition of bioactive alkaloid extracts from some Narcissus species and varieties and their biological activity.  

PubMed

Alkaloid extracts of eight Narcissus (Amaryllidaceae) species and varieties were studied with respect to their acetylcholinesterase (HuAChE) and butyrylcholinesterase (HuBuChE) inhibitory activity and alkaloid patterns. Thirty alkaloids were determined by GC/MS, and twenty-five of them identified from their mass spectra, retention times and retention indexes. Promising HuAChE inhibition activity was demonstrated by six Narcissus taxa and HuBuChE inhibition by N. jonquila cv. Double Campernelle and N. nanus cv. Elka with IC50 values of 24.1 +/- 1.9 microg/mL and 25.1 +/- 1.8 microg/mL, respectively. Two alkaloids were isolated in pure form using preparative TLC and identified as the galanthamine type alkaloid narwedine and the lycorine type alkaloid incartine. Both compounds were tested for their biological activity. They were considered inactive in HuAChE/HuBuChE assays, but showed promising prolyl oligopeptidase inhibition activities with IC50 values of 0.95 +/- 0.12 mM and 0.91 ? 0.09 mM, respectively. PMID:25233595

Havlasová, Jana; Safratová, Marcela; Siatka, Tomás; St?pánková, Sárka; Novák, Zden?k; Locárek, Miroslav; Opletal, Lubomír; Hrabinová, Martina; Jun, Daniel; Benesová, Nina; Kunes, Jirí; Cahlíková, Lucie

2014-08-01

324

Aptamer-Based Molecular Recognition of Lysergamine, Metergoline and Small Ergot Alkaloids  

PubMed Central

Ergot alkaloids are mycotoxins produced by fungi of the genus Claviceps, which infect cereal crops and grasses. The uptake of ergot alkaloid contaminated cereal products can be lethal to humans and animals. For food safety assessment, analytical techniques are currently used to determine the presence of ergot alkaloids in food and feed samples. However, the number of samples which can be analyzed is limited, due to the cost of the equipment and the need for skilled personnel. In order to compensate for the lack of rapid tests for the detection of ergot alkaloids, the aim of this study was to develop a specific recognition element for ergot alkaloids, which could be further applied to produce a colorimetric reaction in the presence of these toxins. As recognition elements, single-stranded DNA ligands were selected by using an iterative selection procedure named SELEX, i.e., Systematic Evolution of Ligands by EXponential enrichment. After several selection cycles, the resulting aptamers were cloned and sequenced. A surface plasmon resonance analysis enabled determination of the dissociation constants of the complexes of aptamers and lysergamine. Dissociation constants in the nanomolar range were obtained with three selected aptamers. One of the selected aptamers, having a dissociation constant of 44 nM, was linked to gold nanoparticles and it was possible to produce a colorimetric reaction in the presence of lysergamine. This system could also be applied to small ergot alkaloids in an ergot contaminated flour sample. PMID:23242153

Rouah-Martin, Elsa; Mehta, Jaytry; van Dorst, Bieke; de Saeger, Sarah; Dubruel, Peter; Maes, Bert U. W.; Lemiere, Filip; Goormaghtigh, Erik; Daems, Devin; Herrebout, Wouter; van Hove, Francois; Blust, Ronny; Robbens, Johan

2012-01-01

325

High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.  

PubMed

RP-HPLC is the main method for the analysis of alkaloids. However, peak tailing is a problem that commonly occurs in the separation of alkaloids. In order to overcome this, three kinds of RP columns were compared for the analysis of protoberberine alkaloids in Coptidis Rhizoma and Phellodendri Cortex in this work. XTerra MS C18 column was the best one which gave the best symmetry factor under the same conditions. With this column, a good separation of the crude extracts of C. Rhizoma and P. Cortex was achieved using 0.1% v/v formic acid buffer and methanol as mobile phase. At the same time, the crude extracts of C. Rhizoma and P. Cortex were analyzed by the LC-ESI-MSn and LC-atmospheric pressure chemical ionization (APCI)-MSn methods. In the analysis of HPLC-ESI/MSn, structures of five protoberberine alkaloids were elucidated, compared to authentic standards, and data from the literature. At the same time, the structure of a novel compound was elucidated. In the HPLC-APCI/ MSn analysis, there was an interesting phenomenon that the relative abundance of the ions M+ and [M + 2]+ was different for different alkaloids. The possible fragmentation pathways of protoberberine alkaloids in APCI/MS analysis were studied for the first time in the present work. PMID:17536728

Ren, Lingling; Xue, Xingya; Zhang, Feifang; Xu, Qing; Liang, Xinmiao

2007-04-01

326

Isolation of glycosidase-inhibiting hyacinthacines and related alkaloids from Scilla socialis.  

PubMed

An examination of the bulbs of Scilla socialis has resulted in the isolation of 11 hyacinthacines, two pyrrolidines, and three piperidines. The structures of the new alkaloids were elucidated by spectroscopic methods as beta-1-C-ethyldeoxymannojirimycin (5), hyacinthacines B7 (10), C2 (11), C3 (12), C4 (13), and C5 (14), and alpha-5-C-(3-hydroxybutyl)hyacinthacine A2 (15). Although, beta-l-homofuconojirimycin (3) and alpha-7-deoxyhomonojirimycin (alpha-7-deoxy-HNJ, 4) are previously known alkaloids, this is the first report of their occurrence in the plant family Hyacinthaceae. Alkaloid 11 was found to be a good inhibitor of bacterial beta-glucosidase and human placenta alpha-l-fucosidase, with IC50 values of 13 and 17 microM, respectively, while alkaloid 12 showed no inhibitory activity toward alpha-l-fucosidase but was a more potent inhibitor of bovine liver beta-galactosidase (IC50 = 52 microM) than 11. Alkaloids 13 and 14 were shown to be inhibitory toward mammalian alpha-glucosidase (IC50 = 45 and 77 microM, respectively), and alkaloid 14 was demonstrated as a moderate inhibitor of bacterial beta-glucosidase (IC50 = 48 microM). PMID:17536859

Kato, Atsushi; Kato, Noriko; Adachi, Isao; Hollinshead, Jackie; Fleet, George W J; Kuriyama, Chinami; Ikeda, Kyoko; Asano, Naoki; Nash, Robert J

2007-06-01

327

Numerical Recipes  

NSDL National Science Digital Library

The Numerical Recipes books are developed by Numerical Recipes Software and published by Cambridge University Press. The website provides information on how to purchase the books, which are part of a series entitled "Numerical Recipes: The Art of Scientific Computing." "Numerical Recipes" is also a copyrighted computer software included in those books and sold separately. The books and software are available in a variety of computer languages, such as C++, C, and Fortran, and provide routines and recipes, along with explanations and "tricks and tips for scientific computing." Visitors can download the whole C (or Fortran) book for free, although the publisher hopes that after sampling a few sections people will buy the book. The website also provides news updates on the products as well as access to the Numerical Recipes Forum, where those interested in scientific computing can interact, ask and answer questions, and trade tips and tricks. Registration is free and a prize is offered to encourage people to join and offer valuable comments.

328

Application of analytical and preparative high-speed counter-current chromatography for separation of alkaloids from Coptis chinensis Franch  

Microsoft Academic Search

Analytical high-speed counter-current chromatography (HSCCC) was used for the systematic selection and optimization of the two-phase solvent system to separate alkaloids from Coptis chinensis Franch. The optimum solvent system thus obtained led to the successful separation of alkaloids from C. chinensis Franch by preparative HSCCC. One batch separation yielded four pure alkaloids, including palmatine, berberine, epiberberine and coptisine from the

Fuquan Yang; Tianyou Zhang; Ren Zhang; Yoichiro Ito

1998-01-01

329

Effect of Chromatographic Conditions on the Separation of Selected Alkaloids on Phenyl Stationary Phase by an HPLC Method  

Microsoft Academic Search

Some alkaloid standards and synthetic or natural alkaloid mixtures were chromatographed on phenyl?silica stationary phases using various aqueous eluents: aqueous methanol or acetonitrile mixture, buffered aqueous mobile phases at pH 3 to suppress silanols' ionisation, or at pH 8 to suppress alkaloids' ionisation. Strong silanophilic interactions that can occur with these analytes and the adsorbent surface can lead to poor

Anna Petruczynik

2006-01-01

330

Venom alkaloids of monogyne and polygyne forms of the red imported fire ant, Solenopsis invicta , in Taiwan  

Microsoft Academic Search

.  Both monogyne and polygyne colonies of Solenopsis invicta now occupy Taiwan. Although venom alkaloids of these ants have been described and synthesized, we here report on a quantitative\\u000a analysis of the two social forms for the first time. The alkaloids were studied by gas chromatography coupled to mass spectrometry\\u000a (GC-MS), and six major venom alkaloids were detectable in both types

L.-C. Lai; R.-N. Huang; W.-J. Wu

2008-01-01

331

Application of 1 H-NMR spectroscopy to validation of berberine alkaloid reagents and to chemical evaluation of Coptidis Rhizoma  

Microsoft Academic Search

Berberine, palmatine, and coptisine are major pharmacologically active protoberberine alkaloids in Coptidis Rhizoma, and have\\u000a been used as indices for chemical evaluation of the crude drug. 1H-NMR spectroscopy was applied to determination of purities of commercial reagents of protoberberine alkaloids. The purities\\u000a of the alkaloids were calculated from the ratios of the intensities of the H-13 singlet signal at about

Keiko Hasada; Takamitsu Yoshida; Takeshi Yamazaki; Naoki Sugimoto; Tetsuji Nishimura; Akito Nagatsu; Hajime Mizukami

2011-01-01

332

Quantitative analysis of metabolic pathways in Catharanthus roseus hairy roots metabolically engineered for terpenoid indole alkaloid overproduction.  

E-print Network

??The important anticancer pharmaceuticals, vinblastine and vincristine, are produced by Catharanthus roseus. Given their cytotoxicity, these valuable alkaloids are produced in very small quantities within… (more)

Sander, Guy William

2009-01-01

333

Characterization of two structural forms of otonecine-type pyrrolizidine alkaloids from Ligularia hodgsonii by NMR spectroscopy.  

PubMed

Clivorine (1) and ligularine (2), two hepatotoxic otonecine-type pyrrolizidine alkaloids isolated from Ligularia hodgsonii, an antitussive traditional Chinese medicine, were investigated in CDCl(3) and D(2)O by various NMR techniques to delineate why this type of alkaloid displays uncharacteristic solubility properties by dissolving in both nonpolar organic and aqueous solutions. The results demonstrated that both alkaloids exist in a non-ionized form in CDCl(3), but in an ionized form in D(2)O, suggesting that this unique dual solubility may play a role in the intoxication resultant from consumption of water extracts of herbs, including herbal teas, containing otonecine-type pyrrolizidine alkaloids. PMID:10869221

Lin, G; Rose, P; Chatson, K B; Hawes, E M; Zhao, X G; Wang, Z T

2000-06-01

334

Numerical analysis  

Microsoft Academic Search

1. General Introduction. Numerical analysis is the area of mathematics and computer science that creates, analyzes, and implements algorithms for solving nu- merically the problems of continuous mathematics. Such problems originate generally from real-world applications of algebra, geometry and calculus, and they involve vari- ables which vary continuously; these problems occur throughout the natural sciences, social sciences, engineering, medicine, and

Kendall E. Atkinson

2007-01-01

335

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-Noel; Iguer-Ouada, Mokrane; Maiza-Benabdesselam, Fadila; Bedjou, Fatiha; Castronovo, Vincent; Bellahcene, Akeila; Tits, Monique; Frederich, Michel

2013-01-01

336

Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells.  

PubMed

In our previous studies, voacamine, a bisindolic alkaloid extracted from Peschiera fuchsiaefolia, was examined for its possible capability of enhancing the cytotoxic effect of doxorubicin (DOX) on multidrug resistant (MDR) human osteosarcoma cells (U-2 OS-R). Voacamine induced in resistant cells a significant increase of drug retention and intranuclear location which became comparable to those observed in the parental sensitive counterparts (U-2 OS-WT). In the present study, the cell survival analysis and the electron microscopic observations confirmed the evident cytotoxicity of DOX on MDR cells after pre-treatment with the plant extract. Moreover, an increase of the reactivity of P-glycoprotein (P-gp) with the monoclonal antibody UIC2, which recognizes an epitope of the drug transporter in its functional conformation, was revealed, demonstrating that voacamine is a substrate of P-gp, thus acting as a competitive antagonist of the cytotoxic agent. Moreover, to investigate if the enhancement of the cytotoxic effect induced by voacamine could be due to an apoptotic process, we carried out the analysis of cell morphology after Hoechst staining and the quantification of apoptosis by Annexin V-FITC assay. These evaluations showed a very low rate of apoptosis in U-2 OS-R cells treated with voacamine and DOX given in association. In addition, the combined treatment induced ultrastructural modifications suggestive of autophagic cell death. In particular, transmission electron microscopy observations revealed the presence of numerous lysosomes and the formation of a large number of autophagosomes containing residual digested material. In conclusion, these findings seem to indicate that voacamine is capable of enhancing the cytotoxic effect of DOX on MDR cells by favouring a lethal autophagic process. PMID:17070665

Meschini, S; Condello, M; Marra, M; Formisano, G; Federici, E; Arancia, G

2007-03-01

337

Metabolic fate of depsides and alkaloid constituents in aqueous extracts from Mercurialis perennis L. during fermentation.  

PubMed

Dog's mercury (Mercurialis perennis L.) is an old medicinal plant, nowadays used in complementary medicine. Aqueous fermented extracts of the plant are being mainly applied in remedies to treat external inflammations, but a thorough phytochemical characterization is still lacking. Therefore, the conversion of characteristic compound classes from M. perennis extracts during fermentation and storage was investigated. The microbial transformation of the two main depsides phaselic acid (=(2R)-O-[(E)-caffeoyl]malic acid; 1) and mercurialis acid (=(2R)-[(E)-caffeoyloxy]glutaric acid; 2) was monitored by HPLC-DAD. The degradation followed a second-order kinetic, and the calculated half-life periods of both constituents were 67 and 30?months, respectively. Several depside metabolites were detected by GC/MS in AcOEt extracts as (t) BuMe2 Si (TBDMS) derivatives after derivatization, mainly dihydrocinnamic acids. Moreover, numerous ?-hydroxy acids were found, allegedly as degradation products from amino acids or peptides. The microbial alteration of the main alkaloid hermidin was also examined. After three days of fermentation, three novel N-metabolites were formed and thoroughly assigned in CH2 Cl2 extracts as a mixture of 3-ethylhermidin, 3-ethylhermidin quinone, and (E/Z)-3-ethylidenehermidin by GC/MS and NMR methods, as well as by means of total synthesis. A mechanism for the formation of these N-metabolites starting from dimeric hermidin oxidation products is proposed. The obtained results reveal the complex pathways plant constituents may undergo during the fermentation of the extracts. PMID:24078603

Lorenz, Peter; Conrad, Jürgen; Stintzing, Florian C

2013-09-01

338

Liriodenine alkaloid in Annona diversifolia during early development.  

PubMed

Plants of the Annonaceae family produce a series of alkaloids, including liriodenine oxoaporphine. Its distribution in these primitive angiosperms suggests that it plays an important role, but very little is known about which plant organs it accumulates in, or in which developmental stages it is synthesised. Accordingly, liriodenine production was studied during the early stages of germination and seedling development in Annona diversifolia Saff. Liriodenine samples were obtained from the roots and were characterised on the basis of spectroscopic data. Quantification was done by HPLC in the organs and tissues of newly collected seeds, seeds following 1-, 2-, 5- and 10-day imbibitions, upon emergence of the radicle and at the seedling stage. According to our results, liriodenine could not have originated from the parent plant, nor during embryogenesis because it appears for the first time in the endosperm approximately 5 days after the start of imbibition. Therefore, its synthesis does not depend directly on photosynthesis. During the seedling stage it is found in the root and the stem but it is absent from the cotyledonary leaves and the first true leaves. Liriodenine biosynthesis begins during the early stages of development in the endosperm and seed radicles. PMID:21790492

de la Cruz Chacón, I; González-Esquinca, A R

2012-01-01

339

HPLC and NMR studies of phenoxazone alkaloids from Pycnoporus cinnabarinus.  

PubMed

Crude extracts of the red-orange, bracket fungus Pycnoporus cinnabarinus, collected from five distinct Australian localities were subjected to a chemical and biological profiling study. Subsequent detailed investigation of two of these specimens resulted in the isolation of the new phenoxazone alkaloid, pycnoporin (8), together with cinnabarin (1), tramesanguin (2), and cinnabarinic acid (3). Ergosterol peroxide (11) was also identified from one of the specimens studied. Compounds 1-3 and 8 were elucidated by detailed spectroscopic analyzes, which included the application of elevated temperature-controlled NMR experiments. In addition to the isolation and characterization of 8, this study describes the first successful HPLC purification strategy and complete 2D NMR spectroscopic characterization of compounds 1-3. Also reported are the antioxidant and antiinflammatory activities of the crude extracts of one of the P. cinnabarinus specimens. Compounds 1-3, 8 and 11 displayed varying degrees of antitumor activity while ergosterol peroxide (11) also showed slight antimicrobial and antiviral activities. This is the first report documenting the significant antitumor activity of cinnabarin (1). PMID:19475991

Dias, Daniel A; Urban, Sylvia

2009-04-01

340

Hobartine: a tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui).  

PubMed

The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N-H...N hydrogen bond which is the only significant intermolecular interaction present in the structure. PMID:25370110

Paz Robles, Cristian; Badilla Vidal, Natalia; Suarez, Sebastián; Baggio, Ricardo

2014-11-15

341

Cyclolization of D-lysergic acid alkaloid peptides.  

PubMed

The tripeptide chains of the ergopeptines, a class of pharmacologically important D-lysergic acid alkaloid peptides, are arranged in a unique bicyclic cyclol based on an amino-terminal ?-hydroxyamino acid and a terminal orthostructure. D-lysergyl-tripeptides are assembled by the nonribosomal peptide synthetases LPS1 and LPS2 of the ergot fungus Claviceps purpurea and released as N-(D-lysergyl-aminoacyl)-lactams. We show total enzymatic synthesis of ergopeptines catalyzed by a Fe²?/2-ketoglutarate-dependent dioxygenase (EasH) in conjunction with LPS1/LPS2. Analysis of the reaction indicated that EasH introduces a hydroxyl group into N-(D-lysergyl-aminoacyl)-lactam at ?-C of the aminoacyl residue followed by spontaneous condensation with the terminal lactam carbonyl group. Sequence analysis revealed that EasH belongs to the wide and diverse family of the phytanoyl coenzyme A hydroxylases. We provide a high-resolution crystal structure of EasH that is most similar to that of phytanoyl coenzyme A hydroxylase, PhyH, from human. PMID:24361048

Havemann, Judith; Vogel, Dominik; Loll, Bernhard; Keller, Ullrich

2014-01-16

342

The influence of Datura ferox alkaloids on egg-laying hens.  

PubMed

Seeds of the weed Datura ferox are frequent contaminants of raw materials used for animal feed. In this study a mixture of scopolamine and hyoscyamine (98:2), the 2 main alkaloids of Datura ferox seeds, was incorporated at 4 total alkaloid levels (1.5, 15, 75 or 150 mg/kg feed) into a control diet fed to 100 egg-laying hens for 3 mo. Alkaloid doses of 150 mg/kg feed reduced egg production for the first 5-6 w of feeding, whereas lower doses had no effect. Egg weight, eggshell thickness and body weight of hens were unaffected at all doses. Doses of 150 mg/kg feed produced significant increases in the cardiac rate of hens after 5 w. Breathing frequency at all doses was unaffected. Determination of plasma aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase and leucine aminopeptidase activities, as well as autopsy and histological examinations, revealed no obvious alkaloid-related toxic effects. It was concluded that a total alkaloid dose as high as 75 mg/kg feed can be safely administered to egg-laying hens. PMID:8197722

Kovatsis, A; Kotsaki-Kovatsi, V P; Nikolaidis, E; Flaskos, J; Tzika, S; Tzotzas, G

1994-04-01

343

Screening of Alkaloidal Fraction of Conium maculatum L. Aerial Parts for Analgesic and Antiinflammatory Activity  

PubMed Central

Conium maculatum Linn. (Umbelliferae) has been traditionally used in the treatment of spasmodic disorders, and to relieve nervous excitation, rheumatic pains in the old and feeble, pain in stomach, pain of gastric ulcer, nervousness and restlessness. Alkaloids have long been considered as bioactive group of constituents present in C. maculatum. Despite a long tradition of use, C. maculatum has not been evaluated pharmacologically to validate its traditional claims for analgesic and antiinflammatory activities. Thus, the present investigations were undertaken with an objective to evaluate alkaloidal fraction of C. maculatum aerial parts for analgesic and antiinflammatory activities. Test doses (100 or 200 mg/kg, p.o.) of alkaloidal fraction were evaluated for analgesic activity using tail flick test and antiinflammatory activity using carrageenan-induced paw oedema test in rats. Morphine (5 mg/kg, p.o.) and indomethacin (5 mg/kg, p.o.) were used as standard analgesic and antiinflammatory drugs, respectively. Alkaloidal fraction of the plant exhibited significant analgesic activity at a dose of 200 mg/kg as it showed significant increase in tail flicking reaction time with respect to the control during 2 h intervals of observation. It also exhibited significant antiinflammatory activity at a dose of 200 mg/kg as it inhibited paw oedema in rats to 71% and reduced the paw volume one-fourth to the control during 1st h of the study. The present investigations suggest that alkaloids are responsible for analgesic and antiinflammatory activities of C. maculatum. PMID:23716876

Madaan, Reecha; Kumar, S.

2012-01-01

344

Screening of Alkaloidal Fraction of Conium maculatum L. Aerial Parts for Analgesic and Antiinflammatory Activity.  

PubMed

Conium maculatum Linn. (Umbelliferae) has been traditionally used in the treatment of spasmodic disorders, and to relieve nervous excitation, rheumatic pains in the old and feeble, pain in stomach, pain of gastric ulcer, nervousness and restlessness. Alkaloids have long been considered as bioactive group of constituents present in C. maculatum. Despite a long tradition of use, C. maculatum has not been evaluated pharmacologically to validate its traditional claims for analgesic and antiinflammatory activities. Thus, the present investigations were undertaken with an objective to evaluate alkaloidal fraction of C. maculatum aerial parts for analgesic and antiinflammatory activities. Test doses (100 or 200 mg/kg, p.o.) of alkaloidal fraction were evaluated for analgesic activity using tail flick test and antiinflammatory activity using carrageenan-induced paw oedema test in rats. Morphine (5 mg/kg, p.o.) and indomethacin (5 mg/kg, p.o.) were used as standard analgesic and antiinflammatory drugs, respectively. Alkaloidal fraction of the plant exhibited significant analgesic activity at a dose of 200 mg/kg as it showed significant increase in tail flicking reaction time with respect to the control during 2 h intervals of observation. It also exhibited significant antiinflammatory activity at a dose of 200 mg/kg as it inhibited paw oedema in rats to 71% and reduced the paw volume one-fourth to the control during 1(st) h of the study. The present investigations suggest that alkaloids are responsible for analgesic and antiinflammatory activities of C. maculatum. PMID:23716876

Madaan, Reecha; Kumar, S

2012-09-01

345

Dietary ergot alkaloids as a possible cause of tail necrosis in rabbits.  

PubMed

This study describes the association between tail necrosis in rabbits and mycotoxins in rabbit feed. Clinical cases of tail necrosis were observed in 14 out of 103 rabbits kept in an outdoor group housing, fed with hay and a commercial pelleted feed. The observed clinical symptoms, alopecia, erosions, crusts and necrosis were restricted to the tail area and exclusively occurred in young rabbits aged 113?±?20 days. Dermatological examination suggested that ischemia had caused necrosis. Analysis of blood samples showed an elevated level of creatine kinase. No weight loss occurred in affected rabbits. Trauma caused by injuries or technopathic lesions was also excluded. Histopathologically, the lesions were characterized by acute muscle fibre degeneration and chronic active dermatitis with granulation tissue formation. Necropsy of one rabbit revealed hepatocellular degeneration and necrosis as remarkable findings. Feed analysis for ergot alkaloids by enzyme immunoassays yielded a mean and maximum ergot alkaloid content of 410?±?250 ?g/kg and 1,700 ?g/kg, respectively. Faeces of affected rabbits contained ergot alkaloids at levels up to 200 ?g/kg. The mean and maximum dietary intake of total ergot alkaloids were 17 and 71 ?g/kg bodyweight, respectively. Fusarium toxins (trichothecenes, zearalenone, fumonisins) were also found in the feed, but at levels which did not explain the observed effects. The results indicate that ergot alkaloids may have been the cause of tail necrosis, which is supported by literature data showing that rabbits are especially sensitive towards these toxins. PMID:25234267

Korn, A K; Gross, M; Usleber, E; Thom, N; Köhler, K; Erhardt, G

2014-11-01

346

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

PubMed

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 alkaloids at different concentrations and presented to neonate larvae. At the highest concentrations (77-100 mg/liter) of ergonovine, ergotamine, ergocryptine, agroclavine, and elymoclavine, larval weights and/or leaf area consumed after eight days were reduced relative to controls. Lysergol had no effect on larval weights and leaf consumption at any concentration. Although active concentrations were higher than those reported from two host grasses, in vivo levels of ergot alkaloids have not been quantified for most endophyte-infected grasses. The detrimental effects on fall armyworm observed in this study suggest that ergot alkaloids could be responsible, at least in part, for the greater insect resistance of endophyte-infected grasses. PMID:24271434

Clay, K; Cheplick, G P

1989-01-01

347

Characterization of Vacuolar Transport of the Endogenous Alkaloid Berberine in Coptis japonica1  

PubMed Central

Alkaloids comprise one of the largest groups of plant secondary metabolites. Many of them exhibit strong biological activities, and, in most cases, they are accumulated in the central vacuole of alkaloid-producing plants after synthesis. However, the mechanisms involved in alkaloid transport across the tonoplast are only poorly understood. In this study, we analyzed the vacuolar transport mechanism of an isoquinoline alkaloid, berberine, which is produced and accumulated in the vacuole of cultured cells of Coptis japonica. The characterization of berberine transport using intact vacuoles and a tonoplast vesicle system showed that berberine uptake was stimulated by Mg/ATP, as well as GTP, CTP, UTP, and Mg/pyrophosphate. Berberine uptake was strongly inhibited by NH4+ and bafilomycin A1, while vanadate, which is commonly used to inhibit ATP-binding cassette transporters, had only a slight effect, which suggests the presence of a typical secondary transport mechanism. This is contrary to the situation in the plasma membrane of this plant cell, where the ATP-binding cassette transporter is involved in berberine transport. Model experiments with liposomes demonstrated that an ion-trap mechanism was hardly implicated in berberine transport. Further studies suggested that berberine was transported across the tonoplast via an H+/berberine antiporter, which has a Km value of 43.7 ?m for berberine. Competition experiments using various berberine analogs, as well as other classes of alkaloids, revealed that this transporter is fairly specific, but not exclusive, for berberine. PMID:16024684

Otani, Mihoko; Shitan, Nobukazu; Sakai, Kyoko; Martinoia, Enrico; Sato, Fumihiko; Yazaki, Kazufumi

2005-01-01

348

Characterization of vacuolar transport of the endogenous alkaloid berberine in Coptis japonica.  

PubMed

Alkaloids comprise one of the largest groups of plant secondary metabolites. Many of them exhibit strong biological activities, and, in most cases, they are accumulated in the central vacuole of alkaloid-producing plants after synthesis. However, the mechanisms involved in alkaloid transport across the tonoplast are only poorly understood. In this study, we analyzed the vacuolar transport mechanism of an isoquinoline alkaloid, berberine, which is produced and accumulated in the vacuole of cultured cells of Coptis japonica. The characterization of berberine transport using intact vacuoles and a tonoplast vesicle system showed that berberine uptake was stimulated by Mg/ATP, as well as GTP, CTP, UTP, and Mg/pyrophosphate. Berberine uptake was strongly inhibited by NH4(+) and bafilomycin A1, while vanadate, which is commonly used to inhibit ATP-binding cassette transporters, had only a slight effect, which suggests the presence of a typical secondary transport mechanism. This is contrary to the situation in the plasma membrane of this plant cell, where the ATP-binding cassette transporter is involved in berberine transport. Model experiments with liposomes demonstrated that an ion-trap mechanism was hardly implicated in berberine transport. Further studies suggested that berberine was transported across the tonoplast via an H+/berberine antiporter, which has a Km value of 43.7 microM for berberine. Competition experiments using various berberine analogs, as well as other classes of alkaloids, revealed that this transporter is fairly specific, but not exclusive, for berberine. PMID:16024684

Otani, Mihoko; Shitan, Nobukazu; Sakai, Kyoko; Martinoia, Enrico; Sato, Fumihiko; Yazaki, Kazufumi

2005-08-01

349

Wild Argentinian Amaryllidaceae, a new renewable source of the acetylcholinesterase inhibitor galanthamine and other alkaloids.  

PubMed

The Amaryllidaceae family is well known for its pharmacologically active alkaloids. An important approach to treat Alzheimer’s disease involves the inhibition of the enzyme acetylcholinesterase (AChE). Galanthamine, an Amaryllidaceae alkaloid, is an effective, selective, reversible, and competitive AchE inhibitor. This work was aimed at studying the alkaloid composition of four wild Argentinian Amarillydaceae species for the first time, as well as analyzing their inhibitory activity on acetylcholinesterase. Alkaloid content was characterized by means of GC-MS analysis. Chloroform basic extracts from Habranthus jamesonii, Phycella herbertiana, Rhodophiala mendocina and Zephyranthes filifolia collected in the Argentinian Andean region all contained galanthamine, and showed a strong AChE inhibitory activity (IC50 between 1.2 and 2 µg/mL). To our knowledge, no previous reports on alkaloid profiles and AChEIs activity of wild Argentinian Amarillydaceae species have been publisihed. The demand for renewable sources of industrial products like galanthamine and the need to protect plant biodiversity creates an opportunity for Argentinian farmers to produce such crops. PMID:23149565

Ortiz, Javier E; Berkov, Strahil; Pigni, Natalia B; Theoduloz, Cristina; Roitman, German; Tapia, Alejandro; Bastida, Jaume; Feresin, Gabriela E

2012-01-01

350

Luminescence and binding properties of two isoquinoline alkaloids chelerythrine and sanguinarine with ctDNA  

NASA Astrophysics Data System (ADS)

The binding mode and mechanism of the interactions between two planar cationic alkaloids chelerythrine (Che) and sanguinarine (San) with calf thymus DNA (ctDNA) were systematically investigated at pH 5.40 using UV-vis absorption spectroscopy, fluorescence spectroscopy and cyclic voltammetry. Che and San show strong fluorescence at 570 and 589 nm, respectively. Che displays fluorescence enhancement with ctDNA whereas the fluorescence of San is quenched on interaction with ctDNA. In addition, UV-vis spectra of both alkaloids show apparent hypochromicity and are bathochromic shifted, indicating that they could intercalate into ctDNA bases. The fluorescence polarization of Che and San increases in the presence of ctDNA, again implying the intercalation of two alkaloids with ctDNA. This conclusion was also supported by the results obtained from anion quenching and cyclic voltammetry. The binding constants of both alkaloids with ctDNA were calculated in the order of 105 L/mol. San binds with ctDNA 3-fold stronger than Che. The stoichiometric bindings are five nucleotides per Che or San. Electrostatic binding also exists between the alkaloids and DNA helix. Finally, theoretical calculations show that only certain parts of Che and San molecules intercalate into the DNA helix.

Li, Junfen; Li, Baohong; Wu, Yanbo; Shuang, Shaomin; Dong, Chuan; Choi, Martin M. F.

2012-09-01

351

Protective role of Coptidis Rhizoma alkaloids against peroxynitrite-induced damage to renal tubular epithelial cells.  

PubMed

A study was conducted to elucidate and compare the protective activity of alkaloids from Coptidis Rhizoma (berberine, coptisine, palmatine, epiberberine, jatrorhizine, groenlandicine and magnoflorine) using an LLC-PK(1) cell under peroxynitrite (ONOO(-)) generation model. Treatment with 3-morpholinosydnonimine (SIN-1) led to an increase in cellular ONOO(-) generation in comparison with non-treated cells. However, Coptidis Rhizoma extract and its alkaloids, except for berberine, reduced the cellular ONOO(-) level. In addition, DNA fragmentation induced by SIN-1 was significantly decreased by the extract, and also by coptisine, epiberberine, jatrorhizine, groenlandicine and magnoflorine. Moreover, treatment with berberine, coptisine, palmatine and epiberberine exerted a protective effect against G(0)/G(1)phase arrest of cell cycle induced by SIN-1. The increase in cellular ONOO(-) generation, DNA damage and disturbance of the cell cycle by SIN-1 resulted in a decrease in cell viability. However, Coptidis Rhizoma extract, epiberberine, jatrorhizine, groenlandicine and magnoflorine significantly increased cell viability even at a concentration as low as 10 microg mL(-1). These findings demonstrate that Coptidis Rhizoma extract and its alkaloids can ameliorate the cell damage associated with ONOO(-) generation in renal tubular LLCPK(1) cells, and that the various alkaloids have distinctive mechanisms of action, such as ONOO(-) scavenging, protection from DNA damage and control of the cell cycle. Furthermore, the data suggest that among the Coptidis Rhizoma alkaloids, coptisine is the most effective for protection against SIN-1-induced cellular injury in terms of its potency and content. PMID:15807993

Yokozawa, Takako; Satoh, Akiko; Cho, Eun Ju; Kashiwada, Yoshiki; Ikeshiro, Yasumasa

2005-03-01

352

Cytokinin-enhanced accumulation of indole alkaloids in Catharanthus roseus cell cultures — The factors affecting the cytokinin response  

Microsoft Academic Search

Summary Cytokinins were found to stimulate the alkaloid synthesis induced by removing auxin from the medium of a cell line of Catharanthus roseus. Diluting the mineral salts of the culture medium decreased the alkaloid production but increased the “sensitivity” of the cells. Addition of high levels of Ca2+, Mg2+ or Sr2+ to B5 media in which the mineral salts were

Alain Decendit; Di Liu; Lazhar Ouelhazi; Pierre Doireau; Jean-Michel Mérillon; Marc Rideau

1992-01-01

353

Effect of fungal homogenate, enzyme inhibitors and osmotic stress on alkaloid content of Catharanthus roseus cell suspension cultures  

Microsoft Academic Search

The addition of Aspergillus niger homogenate to Catharanthus roseus cell suspension cultures produced an increment of more than 60% in the alkaloid content of two different cell lines. The use of an inhibitor of phenylalanine ammonia lyase, i. e. cinnamic acid, along with the homogenate, resulted in an appearance of 90% of the alkaloids in the medium. Furthermore, even in

Gregorio Godoy-Hernfindez; Víctor M. Loyola-Vargas

1991-01-01

354

Cytotoxic effects of cigarette smoke alkaloids inhibit the progesterone production and cell growth of cultured MA10 Leydig tumor cells  

Microsoft Academic Search

Inhibition of corpus luteum progesterone synthesis by cigarette smoke alkaloids might, in part, explain the generally poorer outcome of pregnancy in smoking women. The present experiments evaluate the effects of cigarette smoke alkaloids on progesterone biosynthesis and cell growth. Studies were based using the MA-10 Leydig tumor cell line. The steroid pathway in MA-10 cells has only two specific enzymatic

P. M. Gocze; D. A. Freeman

2000-01-01

355

Vaccination Against Ergot Alkaloids and the Effect of Endophyte-Infected Fescue Seed-Based Diets on Rabbits1  

Microsoft Academic Search

Three sequential experiments were conducted with rabbits to 1 ) determine the effect of endophyte-infected (E+) tall fescue seed on rabbit performance and examine the effect of anti-ergot alkaloid immunization on rabbit performance and protectiveness against fescue toxicosis, 2 ) compare immunogens designed to elicit systemic anti-ergot alkaloid antibodies, and 3 ) select a superior adjuvant. In Exp. 1, rabbits

N. M. Filipov; F. N. Thompson; N. S. Hill; D. L. Dawe; J. A. Stuedemann; C. K. Smith

356

Five new alkaloids from Coptidis Rhizoma-Euodiae Fructus couple and their cytotoxic activities against gastrointestinal cancer cells.  

PubMed

A new indoloquinazoline alkaloid, 10-methoxywuchuyuamide I (1), three new benzylisoquinoline alkaloids, named as coptichic aldehyde (2), coptichine (3) and 13-carboxaldehyde-8-oxocoptisine (4), and a new isoindoline alkaloid, named as coptichinamide (5), together with two known alkaloids, wuchuyuamide I (6) and 8-oxocoptisine (7) were isolated from the Coptidis Rhizoma-Euodiae Fructus couple. Their chemical structures were determined by extensive spectroscopic analyses, including IR, UV, EI-MS, HRESI-MS, 1D and 2D NMR data ((1)H NMR, (13)C NMR, (1)H-(1)H COSY, HSQC and HMBC). Cytotoxicities of the isolated alkaloids against NCI-N87 and Caco-2 cell lines were evaluated. Four benzylisoquinoline alkaloids 2-4 and 7 showed inhibitory activities against NCI-N87 cell with IC50 values range from 8.92 to 35.98 ?M. The alkaloid 3 was a new antiproliferation compound against NCI-N87 cells. The results provided valuable information for further investigation of alkaloid 3 as a chemopreventive agent. PMID:24384278

Qian, Ping; Yang, Xiu-Wei

2014-03-01

357

Antisense RNA-Mediated Suppression of Benzophenanthridine Alkaloid Biosynthesis in Transgenic Cell Cultures of California Poppy1  

PubMed Central

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 and displaying low levels of BBE or CYP80B1 mRNAs, respectively, showed reduced accumulation of benzophenanthridine alkaloids compared with control cultures transformed with a ?-glucuronidase gene. Pathway intermediates were not detected in any of the transformed cell lines. The suppression of benzophenanthridine alkaloid biosynthesis using BBE or CYP80B1 antisense RNA constructs also reduced the growth rate of the cultures. Two-dimensional 1H-nuclear magnetic resonance and in vivo 15N-nuclear magnetic resonance spectroscopy showed no difference in the abundance of carbohydrate metabolites in the various transgenic cell lines. However, transformed cells with reduced benzophenanthridine alkaloid levels contained larger cellular pools of several amino acids including alanine, leucine, phenylalanine, threonine, and valine compared with controls. The relative abundance of tyrosine, from which benzophenanthridine alkaloids are derived, was less than 2-fold higher in antisense-suppressed cells relative to controls. These results show that alterations in the metabolic flux through benzophenanthridine alkaloid biosynthesis can affect the regulation of amino acid pools. These data provide new insight into the metabolic engineering of benzophenanthridine alkaloid pathways. PMID:11842172

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

2002-01-01

358

Synthesis of Bis(indole) Alkaloids from Arundo donax: The Ynindole Diels-Alder Reaction, Conformational Chirality, and Absolute Stereochemistry.  

PubMed

Bis(indole) alkaloids from Arundo donax were synthesized using the first ynindole Diels-Alder reaction. The alkaloids are chiral, having stable enantiomeric conformations with half-lives of racemization of t1/2 =4150-25100?seconds at room temperature. Their absolute stereochemistry was determined using the exciton chirality method. PMID:25200279

Chen, Jingjin; Ferreira, Andrew J; Beaudry, Christopher M

2014-10-27

359

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 -bis- glutathionyl spermidine conjugate trypanothione (T[S]2) to dihydrotrypanothione (T[SH]2

Schnaufer, Achim

360

Isolation, structure elucidation and biological activity of hederacine A and B, two unique alkaloids from Glechoma hederaceae  

Microsoft Academic Search

Preparative HPLC purification of a methanol extract of the aerial parts of Glechoma hederaceae has yielded two unique alkaloids, hederacine A (1) and hederacine B (2). The structures of these compounds were established unequivocally by UV, IR, MS and a series of 1D and 2D NMR analyses. These alkaloids were inactive against any of the 11 bacterial species at test

Yashodharan Kumarasamy; Philip J Cox; Marcel Jaspars; Lutfun Nahar; Satyajit D Sarker

2003-01-01

361

The effect of body condition on serum concentrations of two teratogenic alkaloids (anagyrine and ammodendrine) from lupines (Lupinus species) that cause crooked calf disease1  

Microsoft Academic Search

Several species of lupine (Lupinus spp.) are toxic to livestock, causing death losses in sheep and cattle but more commonly crooked calf disease in preg- nant range cows. The major toxic alkaloids in lupine are of the quinolizidine alkaloid group and include the teratogen anagyrine, which is primarily responsible for crooked calf disease. Lupines also contain teratogenic piperidine alkaloids including

S. T. Lee; K. E. Panter; J. A. Pfister; D. R. Gardner; K. D. Welch

362

Alteration of the Alkaloid Profile in Genetically Modified Tobacco Reveals a Role of Methylenetetrahydrofolate Reductase in Nicotine N-Demethylation1[C][W][OA  

PubMed Central

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

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

2013-01-01

363

Two new vinblastine-type N-oxide alkaloids from Catharanthus roseus.  

PubMed

Two new vinblastine-type N-oxide alkaloids, 17-desacetoxyvinblastine N'b-oxide (1) and 20'-deoxyvinblastine N'b-oxide (2), were isolated from the leaves of Catharanthus roseus. The structures of 1 and 2 were established by the analysis of their nuclear magnetic resonance and HR-ESI-MS spectroscopic data. All alkaloids were evaluated for their cytotoxic activities against the human hepatocellular carcinoma (HepG2) cell line, human colorectal carcinoma (Lovo) cell line and human breast carcinoma (MCF-7) cell line by the MTT method in vitro, respectively. The results showed that cytotoxic activities of alkaloids 1 and 2 exhibited moderate inhibitory activity on the proliferation of three cancer cells. PMID:23621523

Zhang, Wei-Ku; Xu, Jie-Kun; Tian, Hai-Yan; Wang, Lei; Zhang, Xiao-Qi; Xiao, Xu-Zhi; Li, Ping; Ye, Wen-Cai

2013-10-01

364

Oxidative stress and production of bioactive monoterpene indole alkaloids: biotechnological implications.  

PubMed

Monoterpene indole alkaloids (MIAs) encompass plant natural products with important pharmacological relevance. They include the anti-tumoral MIAs found in Catharanthus roseus and Camptotheca acuminata. The often low yields of bioactive alkaloids in plants has prompted research to identify the factors regulating MIA production. Oxidative stress is a general response associated with biotic and abiotic stresses leading to several secondary responses, including elicitation of MIA production. These changes in secondary metabolism may take place directly or via second messengers, such as Ca(2+) and reactive oxygen species (ROS). H2O2 is the main ROS that participates in MIA biosynthesis. This review analyzes the links between oxidative stress, elicitation of bioactive MIA production and their potential roles in antioxidant defense, as well as exploring the implications to developing biotechnological strategies relevant for alkaloid supply. PMID:24062135

Matsuura, Hélio Nitta; Rau, Mariana Ritter; Fett-Neto, Arthur Germano

2014-02-01

365

[Mechanisms of the alkaloid aurantioclavine excretion and uptake during Penicillium nalgiovense VKM F-229 growth].  

PubMed

The biphasic dynamics of the alkaloid aurantioclavine in the culture liquid of Penicillium nalgiovense VKM F-229 is shown to be due to the diauxic growth of the fungus on two carbon sources, succinate and mannitol. In the phase of active growth on succinate, the fungus synthesizes aurantioclavine and excretes it into the medium in an energy-independent manner, as a result of which the concentration of the alkaloid in the culture liquid rises. During the phase of metabolic adaptation to the other carbon source, mannitol, the concentration of aurantioclavine in the culture liquid falls, probably due to the energy-dependent uptake of the alkaloid by fungal cells. The reversible excretion of aurantioclavine in P. nalgiovense indicates that these are regulated processes and depend on the growth parameters and the physiological state of the fungus. PMID:12751241

Zhelifonova, V P; Kulakovskaia, T V; Kozlovski?, A G

2003-01-01

366

Assessment of mechanisms involved in antinociception produced by the alkaloid caulerpine.  

PubMed

In previous works we showed that oral administration of caulerpine, a bisindole alkaloid isolated from algae of the genus Caulerpa, produced antinociception when assessed in chemical and thermal models of nociception. In this study, we evaluated the possible mechanism of action of this alkaloid in mice, using the writhing test. The antinociceptive effect of caulerpine was not affected by intraperitoneal (i.p.) pretreatment of mice with naloxone, flumazenil, l-arginine or atropine, thus discounting the involvement of the opioid, GABAergic, l-arginine-nitric oxide and (muscarinic) cholinergic pathways, respectively. In contrast, i.p. pretreatment with yohimbine, an ?2-adrenoceptor antagonist, or tropisetron, a 5-HT3 antagonist, significantly blocked caulerpine-induced antinociception. These results suggest that caulerpine exerts its antinociceptive effect in the writhing test via pathways involving ?2-adrenoceptors and 5-HT3 receptors. In summary, this alkaloid could be of interest in the development of new dual-action analgesic drugs. PMID:25230124

Cavalcante-Silva, Luiz Henrique Agra; Falcão, Maria Alice Pimentel; Vieira, Ana Carolina Santana; Viana, Max Denisson Maurício; de Araújo-Júnior, João Xavier; Sousa, Jéssica Celestino Ferreira; da Silva, Tania Maria Sarmento; Barbosa-Filho, José Maria; Noël, François; de Miranda, George Emmanuel C; Santos, Bárbara Viviana de Oliveira; Alexandre-Moreira, Magna Suzana

2014-01-01

367

Quantification of Fumaria officinalis isoquinoline alkaloids by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry.  

PubMed

A capillary electrophoresis (CE) method using non-aqueous (NA) separation solutions combined with an ion trap mass spectrometer (MS and MS/MS) as detection device is presented for the separation, identification and quantification of isoquinoline alkaloids from Fumaria officinalis. The best results were obtained with a mixture of acetonitrile-methanol (9:1, v/v) containing 60mM ammonium acetate and 2.2M acetic acid as running electrolyte and an applied voltage of 30 kV. Electrospray MS measurements were performed in the positive ionization mode with isopropanol-water (1:1, v/v) as sheath liquid at a flow rate of 3 microl/min. Alkaloids were detected as [M+H](+)-ions and showed typical fragmentation patterns in MS/MS experiments. The developed assay was used for the quantification of seven isoquinoline alkaloids representing different structural subtypes in Fumariae herba extracts and F. herba containing phytopharmaceuticals. PMID:16378615

Sturm, Sonja; Strasser, Eva-Maria; Stuppner, Hermann

2006-04-21

368

Exposure to ergot alkaloids during gestation reduces fetal growth in sheep  

PubMed Central

Tall fescue [Lolium arundinaceum (Schreb.) Darbysh; Schedonorus phoenix (Scop.) Holub] is the primary cool season perennial grass in the eastern U.S. Most tall fescue contains an endophyte (Neotyphodium coenophialum), which produces ergot alkaloids that cause vasoconstriction and could restrict blood flow to the fetus in pregnant animals. The objective of this study was to examine fetal growth during maternal exposure to ergot alkaloids during gestation. Pregnant ewes (n = 16) were randomly assigned to one of two dietary treatments: (1) endophyte-infected (N. coenophialum) tall fescue seed (E+; 0.8 ug of ergovaline /g diet DM) and (2) endophyte-free tall fescue seed (E?; 0.0 ug of ergovaline/g diet DM). Birth weight of lambs was reduced by 37% for E+ compared to E?. Organ and muscle weights were also lighter for E+ than E?. Exposure to ergot alkaloids in utero reduces fetal growth and muscle development. PMID:25191653

Duckett, Susan K.; Andrae, John G.; Pratt, Scott L.

2014-01-01

369

Free radical scavenging activity and lipoxygenase inhibition of Mahonia aquifolium extract and isoquinoline alkaloids  

PubMed Central

Roots and stem-bark of Mahonia aquifolium (Oregon grape) (Berberidaceae) are effectively used in the treatment of skin inflammatory conditions. In the present study, the effect of Mahonia aquifolium crude extract and its two representative alkaloid fractions containing protoberberine and bisbenzylisoquinoline (BBIQ) alkaloids on activity of 12-lipoxygenase (12-LOX), was studied. The reactivity with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), a free stable radical, was evaluated to elucidate the rate of possible lipid-derived radical scavenging in the mechanism of the enzyme inhibition. The results indicate that although the direct radical scavenging mechanism cannot be ruled out in the lipoxygenase inhibition by Mahonia aquifolium and its constituents, other mechanisms based on specific interaction between enzyme and alkaloids could play the critical role in the lipoxygenase inhibition rather than non-specific reactivity with free radicals. PMID:17634120

Rackova, Lucia; Oblozinsky, Marek; Kostalova, Daniela; Kettmann, Viktor; Bezakova, Lydia

2007-01-01

370

Monoterpenoid indole alkaloids from Alstonia rupestris with cytotoxic, antibacterial and antifungal activities.  

PubMed

A chemical investigation of the 80% EtOH extract of the aerial plant of Alstonia rupestris afforded four new monoterpenoid indole alkaloids, 6,7-epoxy-8-oxo-vincadifformine (1), 11-acetyl-6,7-epoxy-8-oxo-vincadifformine (2), 11-hydroxy-14-chloro-15-hydroxy-vincadifformine (3), and perakine N1,N4-dioxide (4), together with two known compounds, 11-hydroxy-6,7-epoxy-8-oxovincadifformine (5) and vinorine N1,N4-dioxide (6). Structural elucidation of all the compounds was performed by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. Alkaloids 1, 2 and 5 showed significant cytotoxicities against all the tested tumor cell lines of the head and neck squamous cell carcinoma with IC50 value less than 20 ?M and antimicrobial activities against two fungi (Alternaria alternata and Phytophthora capsici). Alkaloids 4 and 6 exhibited the activity against bacterium Staphylococcus aureus. PMID:24887700

Zhang, Li; Hua, Zequan; Song, Yan; Feng, Chuanwei

2014-09-01

371

Numerical Dating  

NSDL National Science Digital Library

In this exercise, students investigate methods used by geologists studying active tectonics for determining ages in actual numbers of years. Introductory materials describe the three most-used techniques for dating material formed during the Quaternary Period (approximately the last 1.65 million years), discuss the concepts of radioactive decay and half-life, and explain how these may be used to determine the numerical age of an object or substance. The exercise includes a set of problems in which students calculate isotopic abundance, half-life, decay rate, and absolute age. Example problems and a bibliography are provided.

Pinter, Nicholas

372

Numerical Dating  

NSDL National Science Digital Library

In this exercise, students investigate methods used by geologists studying active tectonics for determining ages in actual numbers of years. Introductory materials describe the three most-used techniques for dating material formed during the Quaternary Period (approximately the last 1.65 million years), discuss the concepts of radioactive decay and half-life, and explain how these may be used to determine the numerical age of an object or substance. The exercise includes a set of problems in which students calculate isotopic abundance, half-life, decay rate, and absolute age. Example problems and a bibliography are provided.

Pinter, Nicholas

2011-07-07

373

Alkaloids of the South African Amaryllidaceae: a review.  

PubMed

The plant family Amaryllidaceae is known for its horticultural and ornamental appeal as well as its medicinal value. In relation to these characteristics, trade in Amaryllid flower varieties (especially daffodils) is a multi-million dollar revenue generator for the floriculture industry. Of greater significance are the medicinal attributes of the family, which has already spawned the Alzheimer's prescription drug galanthamine, a potent and selective inhibitor of the enzyme acetylcholinesterase, of significance in the progression of neurodegeneration associated with motor neuron diseases, with annual global sales of around $150 million. Furthermore, it is anticipated that an anticancer drug target related to the Amaryllidaceae alkaloid pancratistatin, presently under advanced clinical evaluation, will enter commercial circulation within the next decade. Members of the Amaryllidaceae are distributed through both tropical and subtropical regions of the globe, but are of prominence within three distinct geographical locations, including Andean South America, the Mediterranean basin, and southern Africa. The southern African zone is known to harbor at least a third of the worldwide complement of around 1000 species, many of which are widely utilized in the traditional medicinal practices of the indigenous people of the region. Given its therapeutic and economic value, its natural abundance in the southern African region, coupled to its widespread usage in ethnic medicine, the family Amaryllidaceae provides a diverse and accessible platform for phytochemical based drug discovery. A consolidation of its traditional usage as well as its chemical and pharmacological profiles will thus guide efforts aimed at maximizing this potential. In undertaking this survey of the Amaryllidaceae of southern African, we aimed to achieve these goals. PMID:24273880

Nair, Jerald J; Bastida, Jaume; Codina, Caries; Viladomat, Francesc; van Staden, Johannes

2013-09-01

374

Thin-Layer Chromatography/Desorption Electrospray Ionization Mass Spectrometry: Investigation of Goldenseal Alkaloids  

SciTech Connect

Desorption electrospray ionization mass spectrometry was investigated as a means to qualitatively identify and to quantify analytes directly from developed normal-phase thin layer chromatography plates. The atmospheric sampling capillary of a commercial ion trap mass spectrometer was extended to permit sampling and ionization of analytes in bands separated on intact TLC plates (up to 10 cm x 10 cm). A surface positioning software package and the appropriate hardware enabled computer-controlled surface scanning along the length of development lanes or at fixed RF value across the plates versus the stationary desorption electrospray emitter. Goldenseal (Hydrastis canadensis) and related alkaloids and commercial dietary supplements were used as standards and samples. Alkaloid standards and samples were spotted and separated on aluminum- or glass-backed plates using established literature methods. The mass spectral signal levels as a function of desorption spray solvent were investigated with acetonitrile proving superior to methanol. The detection levels (ca. 5 ng each or 14 -28 pmol) in mass spectral full scan mode were determined statistically from the calibration curves (2.5 - 100 pmol) for the standards berberine, palmatine and hydrastinine spotted as a mixture and separated on the plates. Qualitative screening of the major alkaloids present in six different over-the-counter "goldenseal" dietary supplements was accomplished by obtaining full scan mass spectra during surface scans along the development lane in the direction of increasing RF value. In one sample, alkaloids were detected that strongly suggested the presence of at least one additional herb undeclared on the product label. These same data indicated the misidentification of one of the alkaloids in the TLC literature. Quantities of the alkaloids present in two of the samples determined using the mass spectral data were in reasonable agreement with the label values indicating the quantitative ability of the method. The advantage of mass spectral measurements in identifying and quantifying materials within overlapping bands and in providing positive identification for even minor species in a mixture was also demonstrated.

Van Berkel, Gary J [ORNL; Tomkins, Bruce A [ORNL; Kertesz, Vilmos [ORNL

2007-01-01

375

CYP719A subfamily of cytochrome P450 oxygenases and isoquinoline alkaloid biosynthesis in Eschscholzia californica.  

PubMed

Eschscholzia californica produces various types of isoquinoline alkaloids. The structural diversity of these chemicals is often due to cytochrome P450 (P450) activities. Members of the CYP719A subfamily, which are found only in isoquinoline alkaloid-producing plant species, catalyze methylenedioxy bridge-forming reactions. In this study, we isolated four kinds of CYP719A genes from E. californica to characterize their functions. These four cDNAs encoded amino acid sequences that were highly homologous to Coptis japonica CYP719A1 and E. californica CYP719A2 and CYP719A3, which suggested that these gene products may be involved in isoquinoline alkaloid biosynthesis in E. californica, especially in methylenedioxy bridge-forming reactions. Expression analysis of these genes showed that two genes (CYP719A9 and CYP719A11) were preferentially expressed in plant leaf, where pavine-type alkaloids accumulate, whereas the other two showed higher expression in root than in other tissues. They were suggested to have distinct physiological functions in isoquinoline alkaloid biosynthesis. Enzyme assay analysis using recombinant proteins expressed in yeast showed that CYP719A5 had cheilanthifoline synthase activity, which was expected based on the similarity of its primary structure to that of Argemone mexicana cheilanthifoline synthase (deposited at DDBJ/GenBanktrade mark/EMBL). In addition, enzyme assay analysis of recombinant CYP719A9 suggested that it has methylenedioxy bridge-forming activity toward (R,S)-reticuline. CYP719A9 might be involved in the biosynthesis of pavine- and/or simple benzylisoquinoline-type alkaloids, which have a methylenedioxy bridge in an isoquinoline ring, in E. californica leaf. PMID:18854999

Ikezawa, Nobuhiro; Iwasa, Kinuko; Sato, Fumihiko

2009-01-01

376

Analysis of the Dendrobium officinale transcriptome reveals putative alkaloid biosynthetic genes and genetic markers.  

PubMed

Dendrobium officinale Kimura et Migo (Orchidaceae) is a traditional Chinese medicinal plant. The stem contains an alkaloid that is the primary bioactive component. However, the details of alkaloid biosynthesis have not been effectively explored because of the limited number of expressed sequence tags (ESTs) available in GenBank. In this study, we analyzed RNA isolated from the stem of D. officinale using a single half-run on the Roche 454 GS FLX Titanium platform to generate 553,084 ESTs with an average length of 417 bases. The ESTs were assembled into 36,407 unique putative transcripts. A total of 69.97% of the unique sequences were annotated, and a detailed view of alkaloid biosynthesis was obtained. Functional assignment based on Kyoto Encyclopedia of Genes and Genomes (KEGG) terms revealed 69 unique sequences representing 25 genes involved in alkaloid backbone biosynthesis. A series of qRT-PCR experiments confirmed that the expression levels of 5 key enzyme-encoding genes involved in alkaloid biosynthesis are greater in the leaves of D. officinale than in the stems. Cytochrome P450s, aminotransferases, methyltransferases, multidrug resistance protein (MDR) transporters and transcription factors were screened for possible involvement in alkaloid biosynthesis. Furthermore, a total of 1061 simple sequence repeat motifs (SSR) were detected from 36,407 unigenes. Dinucleotide repeats were the most abundant repeat type. Of these, 179 genes were associated with a metabolic pathway in KEGG. This study is the first to produce a large volume of transcriptome data from D. officinale. It extends the foundation to facilitate gene discovery in D. officinale and provides an important resource for the molecular genetic and functional genomic studies in this species. PMID:23756193

Guo, Xu; Li, Ying; Li, Chunfang; Luo, Hongmei; Wang, Lizhi; Qian, Jun; Luo, Xiang; Xiang, Li; Song, Jingyuan; Sun, Chao; Xu, Haibin; Yao, Hui; Chen, Shilin

2013-09-15

377

The New ?-D-Glucosidase in Terpenoid-Isoquinoline Alkaloid Biosynthesis in Psychotria ipecacuanha*S?  

PubMed Central

Ipecac alkaloids produced in the medicinal plant Psychotria ipecacuanha such as emetine and cephaeline possess a monoterpenoid-tetrahydroisoquinoline skeleton, which is formed by condensation of dopamine and secologanin. Deglucosylation of one of the condensed products N-deacetylisoipecoside (1?(S)-epimer) is considered to be a part of the reactions for emetine biosynthesis, whereas its 1?(R)-epimer N-deacetylipecoside is converted to ipecoside in P. ipecacuanha. Here, we isolated a cDNA clone Ipeglu1 encoding Ipecac alkaloid ?-d-glucosidase from P. ipecacuanha. The deduced protein showed 54 and 48% identities to raucaffricine ?-glucosidase and strictosidine ?-glucosidase, respectively. Recombinant IpeGlu1 enzyme preferentially hydrolyzed glucosidic Ipecac alkaloids except for their lactams, but showed poor or no activity toward other substrates, including terpenoid-indole alkaloid glucosides. Liquid chromatography-tandem mass spectrometry analysis of deglucosylated products of N-deacetylisoipecoside revealed spontaneous transitions of the highly reactive aglycons, one of which was supposed to be the intermediate for emetine biosynthesis. IpeGlu1 activity was extremely poor toward 7-O-methyl and 6,7-O,O-dimethyl derivatives. However, 6-O-methyl derivatives were hydrolyzed as efficiently as non-methylated substrates, suggesting the possibility of 6-O-methylation prior to deglucosylation by IpeGlu1. In contrast to the strictosidine ?-glucosidase that stereospecifically hydrolyzes 3?(S)-epimer in terpenoid-indole alkaloid biosynthesis, IpeGlu1 lacked stereospecificity for its substrates where 1?(R)-epimers were preferred to 1?(S)-epimers, although ipecoside (1?(R)) is a major alkaloidal glucoside in P. ipecacuanha, suggesting the compartmentalization of IpeGlu1 from ipecoside. These facts have significant implications for distinct physiological roles of 1?(S)- and 1?(R)-epimers and for the involvement of IpeGlu1 in the metabolic fate of both of them. PMID:18927081

Nomura, Taiji; Quesada, Alfonso Lara; Kutchan, Toni M.

2008-01-01

378

In vitro and in vivo hepatoprotective effects of the total alkaloid fraction of Hygrophila auriculata leaves  

PubMed Central

Objective: To investigate the total alkaloid fraction of the methanol extract of leaves of Hygrophila auriculata for its hepatoprotective activity against CCl4-induced toxicity in freshly isolated rat hepatocytes, HepG2 cells, and animal models. Materials and Methods: Mature leaves of H. auriculata were collected, authenticated, and subjected to methanolic extraction followed by isolation of total alkaloid fraction. Freshly isolated rat hepatocytes were exposed to CCl4 (1%) along with/without various concentrations of the total alkaloid fraction (80–40 µg/ml). Protection of human liver-derived HepG2 cells against CCl4-induced damage was determined by the MTT assay. Twenty-four healthy Wistar albino rats (150–200 g) of either sex were used for the in vivo investigations. Liver damage was induced by administration of 30% CCl4 suspended in olive oil (1 ml/kg body weight, i.p). Results: The antihepatotoxic effect of the total alkaloid fraction was observed in freshly isolated rat hepatocytes at very low concentrations (80–40 µg/ml). A dose-dependent increase in the percentage viability was observed when CCl4-exposed HepG2 cells were treated with different concentrations of the total alkaloid fraction. Its in vivo hepatoprotective effect at 80 mg/kg body weight was comparable with that of the standard Silymarin at 250 mg/kg body weight. Conclusion: The total alkaloid fraction was able to normalize the biochemical levels which were altered due to CCl4 intoxication. PMID:20711375

Raj, Vasanth P.; Chandrasekhar, Raghu H.; P., Vijayan; S. A., Dhanaraj; Rao, Mallikarjuna C.; Rao, Venkata J.; Nitesh, K.

2010-01-01

379

Plant tropane alkaloid biosynthesis evolved independently in the Solanaceae and Erythroxylaceae  

PubMed Central

The pharmacologically important tropane alkaloids have a scattered distribution among angiosperm families, like many other groups of secondary metabolites. To determine whether tropane alkaloids have evolved repeatedly in different lineages or arise from an ancestral pathway that has been lost in most lines, we investigated the tropinone-reduction step of their biosynthesis. In species of the Solanaceae, which produce compounds such as atropine and scopolamine, this reaction is known to be catalyzed by enzymes of the short-chain dehydrogenase/reductase family. However, in Erythroxylum coca (Erythroxylaceae), which accumulates cocaine and other tropane alkaloids, no proteins of the short-chain dehydrogenase/reductase family were found that could catalyze this reaction. Instead, purification of E. coca tropinone-reduction activity and cloning of the corresponding gene revealed that a protein of the aldo-keto reductase family carries out this reaction in E. coca. This protein, designated methylecgonone reductase, converts methylecgonone to methylecgonine, the penultimate step in cocaine biosynthesis. The protein has highest sequence similarity to other aldo-keto reductases, such as chalcone reductase, an enzyme of flavonoid biosynthesis, and codeinone reductase, an enzyme of morphine alkaloid biosynthesis. Methylecgonone reductase reduces methylecgonone (2-carbomethoxy-3-tropinone) stereospecifically to 2-carbomethoxy-3?-tropine (methylecgonine), and has its highest activity, protein level, and gene transcript level in young, expanding leaves of E. coca. This enzyme is not found at all in root tissues, which are the site of tropane alkaloid biosynthesis in the Solanaceae. This evidence supports the theory that the ability to produce tropane alkaloids has arisen more than once during the evolution of the angiosperms. PMID:22665766

Jirschitzka, Jan; Schmidt, Gregor W.; Reichelt, Michael; Schneider, Bernd; Gershenzon, Jonathan; D'Auria, John Charles

2012-01-01

380

Composition and stereochemistry of ephedrine alkaloids accumulation in Ephedra sinica Stapf  

Microsoft Academic Search

Ephedra sinica Stapf (Ephedraceae) is a widely used Chinese medicinal plant (Chinese name: Ma Huang). The main active constituents of E. sinica are the unique and taxonomically restricted adrenergic agonists phenylpropylamino alkaloids, also known as ephedrine alkaloids: (1R,2S)-norephedrine (1S,2S)-norpseudoephedrine, (1R,2S)-ephedrine, (1S,2S)-pseudoephedrine, (1R,2S)-N-methylephedrine and (1S,2S)-N-methylpseudoephedrine. GC–MS analysis of freshly picked young E. sinica stems enabled the detection of 1-phenylpropane-1,2-dione and (S)-cathinone,

Raz Krizevski; Einat Bar; Shalit; Yaron Sitrit; Shimon Ben-Shabat; Efraim Lewinsohn

2010-01-01

381

Chemical structure and pharmacological (curarizing) properties of various indole alkaloids extracted from an African Strychnos.  

PubMed

The chemical separation and identification of ten alkaloids extracted from the roots of Strychnos usambarensis are described. The elucidation of their structure by means of elementary analysis, I. R., U.V, and mass spectrometry allows their classification into bistertiary amines, hybrid and bisquaternary ammonium derivatives. This classification is reflected in the pharmacological properties. One of the tertiary amine alkaloids (usambarensine) presents atopine-like and spasmolytic activities while the bisquaternary ammonium compounds (dihydrotoxiferine, calebassine, C-curarine and afrocurarine) are competitive neuromuscular blocking agents. PMID:126050

Angenot, L; Dubois, M; Ginion, C; van Dorsser, W; Dresse, A

1975-06-01

382

Teratogenic effects in cattle of Conium maculatum and conium alkaloids and analogs.  

PubMed

The plant Conium maculatum produced congenital defects in calves born to cows gavaged the fresh green plant during days 50-75 of gestation. Both arthrogryposis and spinal curvature were produced and were similar to the defects produced by the piperidine alkaloid coniine. The arthrogrypotic manifestations of the condition markedly increased in severity as the animals aged. Animals gavaged dry plant had either normal or equivocally deformed offspring. A number of chain length and ring saturation analogs of coniine were not teratogenic. No congenital defects arose in offspring from maternal inhalation of either the teratogenic alkaloid coniine, or from the teratogenic green plant. PMID:630821

Keeler, R F; Balls, L D

1978-01-01

383

Cynoglossum officinale (hound's-tongue)--a cause of pyrrolizidine alkaloid poisoning in horses.  

PubMed

The death of 10 horses was attributed to feeding dried grass hay containing hound's-tongue, Cynoglossum officinale. Affected horses developed weight loss, icterus, photosensitization, and hepatic encephalopathy. Histologic examination of the liver of 3 of the horses revealed megalocytosis, biliary hyperplasia, and fibrosis characteristic of pyrrolizidine alkaloid poisoning. Hound's-tongue was found to contain large quantities (0.6% to 2.1%, dry matter basis) of toxic pyrrolizidine alkaloids, which, when fed to a pony for 20 days, caused liver fibrosis and biliary hyperplasia. PMID:6490488

Knight, A P; Kimberling, C V; Stermitz, F R; Roby, M R

1984-09-15

384

Ergot alkaloid intoxication in perennial ryegrass (Lolium perenne): an emerging animal health concern in Ireland?  

PubMed

Four primary mycotoxicosis have been reported in livestock caused by fungal infections of grasses or cereals by members of the Clavicipitaceae family. Ergotism (generally associated with grasses, rye, triticale and other grains) and fescue toxicosis (associated with tall fescue grass, Festuca arundinacea) are both caused by ergot alkaloids, and referred to as 'ergot alkaloid intoxication'. Ryegrass staggers (associated with perennial ryegrass Lolium perenne) is due to intoxication with an indole-diperpene, Lolitrem B, and metabolites. Fescue-associated oedema, recently described in Australia, may be associated with a pyrrolizidine alkaloid, N-acetyl norloline. Ergotism, caused by the fungus Claviceps purpurea, is visible and infects the outside of the plant seed. Fescue toxicosis and ryegrass staggers are caused by Neotyphodium coenophalium and N. lolii, respectively. Fescue-associated oedema has been associated with tall fescue varieties infected with a specific strain of N. coenophialum (AR542, Max P or Max Q). The name Neotyphodium refers to asexual derivatives of Epichloë spp., which have collectively been termed the epichloë fungi. These fungi exist symbiotically within the grass and are invisible to the naked eye. The primary toxicological effect of ergot alkaloid involves vasoconstriction and/or hypoprolactinaemia. Ingestion of ergot alkaloid by livestock can cause a range of effects, including poor weight gain, reduced fertility, hyperthermia, convulsions, gangrene of the extremities, and death. To date there are no published reports, either internationally or nationally, reporting ergot alkaloid intoxication specifically associated with perennial ryegrass endophytes. However, unpublished reports from the Irish Equine Centre have identified a potential emerging problem of ergot alkaloid intoxication with respect to equines and bovines, on primarily perennial ryegrass-based diets. Ergovaline has been isolated in varying concentrations in the herbage of a small number of equine and bovine farms where poor animal health and performance had been reported. Additionally, in some circumstances changes to the diet, where animals were fed primarily herbage, were sufficient to reverse adverse effects. Pending additional information, these results suggest that Irish farm advisors and veterinarians should be aware of the potential adverse role on animal health and performance of ergot alkaloids from perennial ryegrass infected with endophytic fungi. PMID:25295161

Canty, Mary J; Fogarty, Ursula; Sheridan, Michael K; Ensley, Steve M; Schrunk, Dwayne E; More, Simon J

2014-01-01

385

Factors affecting total alkaloid and nitrate levels in pearl millet (Pennisetum americanum (L.) Leeke)  

E-print Network

oids and Nitrate Besid. es the simultaneous accumulation of alkaloids and NO in pearl millet (Rouquette et al. , 1980), these compounds have also I p N d t z i t g th ' Phd. ' s t' (N et al. , 1966), and in tall fescue (Festuca arundinacea Schreb...oids and Nitrate Besid. es the simultaneous accumulation of alkaloids and NO in pearl millet (Rouquette et al. , 1980), these compounds have also I p N d t z i t g th ' Phd. ' s t' (N et al. , 1966), and in tall fescue (Festuca arundinacea Schreb...

Krejsa, Beverly Blohowiak

2012-06-07

386

Natural aristolactams and aporphine alkaloids as inhibitors of CDK1/cyclin B and DYRK1A.  

PubMed

In an effort to find potent inhibitors of the protein kinases DYRK1A and CDK1/Cyclin B, a systematic in vitro evaluation of 2,500 plant extracts from New Caledonia and French Guyana was performed. Some extracts were found to strongly inhibit the activity of these kinases. Four aristolactams and one lignan were purified from the ethyl acetate extracts of Oxandra asbeckii and Goniothalamus dumontetii, and eleven aporphine alkaloids were isolated from the alkaloid extracts of Siparuna pachyantha, S. decipiens, S. guianensis and S. poeppigii. Among these compounds, velutinam, aristolactam AIIIA and medioresinol showed submicromolar IC50 values on DYRK1A. PMID:23467012

Marti, Guillaume; Eparvier, Véronique; Morleo, Barbara; Le Ven, Jessica; Apel, Cécile; Bodo, Bernard; Amand, Séverine; Dumontet, Vincent; Lozach, Olivier; Meijer, Laurent; Guéritte, Françoise; Litaudon, Marc

2013-01-01

387

Ergot alkaloid intoxication in perennial ryegrass (Lolium perenne): an emerging animal health concern in Ireland?  

PubMed Central

Four primary mycotoxicosis have been reported in livestock caused by fungal infections of grasses or cereals by members of the Clavicipitaceae family. Ergotism (generally associated with grasses, rye, triticale and other grains) and fescue toxicosis (associated with tall fescue grass, Festuca arundinacea) are both caused by ergot alkaloids, and referred to as ‘ergot alkaloid intoxication’. Ryegrass staggers (associated with perennial ryegrass Lolium perenne) is due to intoxication with an indole-diperpene, Lolitrem B, and metabolites. Fescue-associated oedema, recently described in Australia, may be associated with a pyrrolizidine alkaloid, N-acetyl norloline. Ergotism, caused by the fungus Claviceps purpurea, is visible and infects the outside of the plant seed. Fescue toxicosis and ryegrass staggers are caused by Neotyphodium coenophalium and N. lolii, respectively. Fescue-associated oedema has been associated with tall fescue varieties infected with a specific strain of N. coenophialum (AR542, Max P or Max Q). The name Neotyphodium refers to asexual derivatives of Epichloë spp., which have collectively been termed the epichloë fungi. These fungi exist symbiotically within the grass and are invisible to the naked eye. The primary toxicological effect of ergot alkaloid involves vasoconstriction and/or hypoprolactinaemia. Ingestion of ergot alkaloid by livestock can cause a range of effects, including poor weight gain, reduced fertility, hyperthermia, convulsions, gangrene of the extremities, and death. To date there are no published reports, either internationally or nationally, reporting ergot alkaloid intoxication specifically associated with perennial ryegrass endophytes. However, unpublished reports from the Irish Equine Centre have identified a potential emerging problem of ergot alkaloid intoxication with respect to equines and bovines, on primarily perennial ryegrass-based diets. Ergovaline has been isolated in varying concentrations in the herbage of a small number of equine and bovine farms where poor animal health and performance had been reported. Additionally, in some circumstances changes to the diet, where animals were fed primarily herbage, were sufficient to reverse adverse effects. Pending additional information, these results suggest that Irish farm advisors and veterinarians should be aware of the potential adverse role on animal health and performance of ergot alkaloids from perennial ryegrass infected with endophytic fungi. PMID:25295161

2014-01-01

388

Sanguinarine: its potential as a liver toxic alkaloid present in the seeds of Argemone mexicana.  

PubMed

The alkaloid sanguinarine reported to be responsible for several outbreaks of epidemic dropsy in the tropics was examined for its hepatotoxic potential in rats. The studies showed that a single i.p. dose (10 mg/kg) of sanguinarine not only increased the activity of SGPT and SGOT substantially but also caused a significant loss of microsomal cytochrome P-450 and benzphetamine N-demethylase activity. Furthermore, the treated rats exhibited considerable loss of body and liver weight, peritoneal edema and slightly enlarged livers with fibrinous material. Microscopic examination of the liver tissue showed progressive cellular degeneration and necrosis further substantiating that sanguinarine is a potential hepatotoxic alkaloid. PMID:3967743

Dalvi, R R

1985-01-15

389

A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides.  

PubMed

A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted delta-lactams. The delta-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields. PMID:20376396

Wang, Ning; Zhang, Li-He; Ye, Xin-Shan

2010-06-01

390

Exploratory studies towards a total synthesis of the unusual bridged tetracyclic Lycopodium alkaloid lycopladine H  

PubMed Central

A strategy for a total synthesis of the structurally novel Lycopodium alkaloid lycopladine H has been investigated. Key steps that have been tested include: 1.a regioselective Diels-Alder cycloaddition of nitroethylene with an o-quinone ketal to produce the bicyclo[2.2.2]octane moiety of the alkaloid; 2. a stereoselective Henry reaction to generate the requisite functionality and configuration at C-5; 3. a stereoselective catalytic hydrogenation of a trisubstituted alkene to set the C-15 methyl configuration. PMID:22125345

Sacher, Joshua R.; Weinreb, Steven M.

2011-01-01

391

Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related aspidosperma alkaloids.  

PubMed

We report an efficient and highly stereoselective strategy for the synthesis of Aspidosperma alkaloids based on the transannular cyclization of a chiral lactam precursor. Three new stereocenters are formed in this key step with excellent diastereoselectivity due to the conformational bias of the cyclization precursor, leading to a versatile pentacyclic intermediate. A subsequent stereoselective epoxidation followed by a mild formamide reduction enabled the first total synthesis of the Aspidosperma alkaloids (-)-mehranine and (+)-(6S,7S)-dihydroxy-N-methylaspidospermidine. A late-stage dimerization of (-)-mehranine mediated by scandium trifluoromethanesulfonate completed the first total synthesis of (-)-methylenebismehranine. PMID:25196158

Mewald, Marius; Medley, Jonathan William; Movassaghi, Mohammad

2014-10-20

392

Asymmetric synthetic access to the hetisine alkaloids: total synthesis of (+)-nominine.  

PubMed

A dual cycloaddition strategy for the synthesis of the hetisine alkaloids has been developed, illustrated by a concise asymmetric total synthesis of (+)-nominine (7). The approach relies on an early-stage intramolecular 1,3-dipolar cycloaddition of a 4-oxido-isoquinolinium betaine dipole with an ene-nitrile dipolarophile. Subsequent late-stage pyrrolidine-induced dienamine isomerization/Diels-Alder cascade allows for rapid construction of the carbon--nitrogen polycyclic skeleton within this class of C(20)-diterpenoid alkaloids. PMID:18046691

Peese, Kevin M; Gin, David Y

2008-01-01

393

Opportunities in metabolic engineering to facilitate scalable alkaloid production  

E-print Network

Numerous drugs and drug precursors in the current pharmacopoeia originate from plant sources. The limited yield of some bioactive compounds in plant tissues, however, presents a significant challenge for large-scale drug ...

Leonard, Effendi

394

Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae  

PubMed Central

Larvae of Tyria jacobaeae feed solely upon the pyrrolizidine alkaloid-containing plant Senecio jacobaea. Ingested pyrrolizidine alkaloids (PAs), which are toxic to unspecialized insects and vertebrates, are efficiently N-oxidized in the hemolymph of T. jacobaeae by senecionine N-oxygenase (SNO), a flavin-dependent monooxygenase (FMO) with a high substrate specificity for PAs. Peptide microsequences obtained from purified T. jacobaeae SNO were used to clone the corresponding cDNA, which was expressed in active form in Escherichia coli. T. jacobaeae SNO possesses a signal peptide characteristic of extracellular proteins, and it belongs to a large family of mainly FMO-like sequences of mostly unknown function, including two predicted Drosophila melanogaster gene products. The data indicate that the gene for T. jacobaeae SNO, highly specific for toxic pyrrolizidine alkaloids, was recruited from a preexisting insect-specific FMO gene family of hitherto unknown function. The enzyme allows the larvae to feed on PA-containing plants and to accumulate predation-deterrent PAs in the hemolymph. PMID:11972041

Naumann, Claudia; Hartmann, Thomas; Ober, Dietrich

2002-01-01

395

Increased systemic exposure to rhizoma coptidis alkaloids in lipopolysaccharide-pretreated rats attributable to enhanced intestinal absorption.  

PubMed

Rhizoma coptidis is a rhizome commonly used in traditional Chinese medicine. After oral administration of rhizoma coptidis extract, the plasma concentrations of its effective alkaloid constituents are so low that their systemic therapeutic actions cannot be explained. This study aimed to investigate the influence of lipopolysaccharide (LPS) on the pharmacokinetics of the rhizoma coptidis alkaloids. Pharmacokinetic experiments were performed with rats; both in vitro absorption and efflux experiments were carried out with everted rat gut sacs, whereas in vitro metabolism experiments were conducted with rat liver microsomes and intestinal S9 fractions. Mucosal changes were evaluated with light microscopy and transmission electron microscopy. The results showed that, in rat plasma, LPS pretreatment increased systemic alkaloid exposure. LPS pretreatment increased the in vitro absorption of the alkaloids and decreased their efflux. The efflux of vinblastine and rhodamine 123, P-glycoprotein substrates, also was decreased. The absorption of fluorescein isothiocyanate-labeled dextran (average molecular mass, 4 kDa), a gut paracellular permeability probe, was not influenced. Obvious damage was observed in the mucosa, but the tight junctions between epithelial cells remained intact. Intestinal, rather than hepatic, alkaloid metabolism was decreased. These findings indicated that LPS pretreatment increased systemic exposure to the alkaloids through enhancement of their absorption, which was related to decreased intestinal efflux and metabolism. The results add to the understanding of why rhizoma coptidis is active despite the low plasma concentrations of the rhizoma coptidis alkaloids measured in normal subjects and experimental animals. PMID:22086980

Ma, Bing-Liang; Yao, Meng-Kan; Zhong, Jie; Ma, Yue-Ming; Gao, Cheng-Lu; Wu, Jia-Sheng; Qiu, Fu-Rong; Wang, Chang-Hong; Wang, Xin-Hong

2012-02-01

396

Influence of Precursor Availability on Alkaloid Accumulation by Transgenic Cell Line of Catharanthus roseus  

Microsoft Academic Search

We have used a transgenic cell line of Catharanthus roseus (L.) G. Don to study the relative importance of the supply of biosynthetic precursors for the synthesis of terpenoid indole alkaloids. Line S10 carries a recombinant, constitutively overexpressed version of the endogenous strictosidine synthase (Str) gene. Various concentra- tions and combinations of the substrate tryptamine and of loganin, the immediate

Serap Whitmer; Camilo Canel; Didier Hallard; Cecilia Goncalves; Robert Verpoorte

1998-01-01

397

Large scale fermentation and alkaloid production of cell suspension cultures of Catharanthus roseus  

Microsoft Academic Search

Cell cultures of Catharanthus roseus were scaled up to volumes of 50001 using conventional reactors equipped with flat-blade impellers. The behavior of the fermenter grown cells was compared with corresponding shake flask experiments with respect to growth and indole alkaloid inducibility and production. The limits and problems of transferring shake flask experiments of culture systems such as Catharanthus, in which

Otmar Schiel; Jochen Berlin

1987-01-01

398

Simultaneous determination of Ephedra sinica and Citrus aurantium var. amara alkaloids by ion-pair chromatography  

Microsoft Academic Search

Ephedra sinica (Ma Huang) preparations have recently gained a lot of attention because of serious side effects associated with their prolonged consumption. Citrus aurantium var. amara is now used as an alternative, despite the fact that similar side effects are suspected. We have developed and validated the first analytical procedure for the simultaneous determination of all major alkaloids from both

M. Ganzera; C. Lanser; H. Stuppner

2005-01-01

399

Synthesis of pyridine-containing derivatives of the alkaloids cytisine and d -pseudoephedrine  

Microsoft Academic Search

\\u000a N-(5-Bromopyridyl-2)-2-N?-cytisino-and N?-d-pseudoephedrineoacetamides were synthesized by reaction of the alkaloids cytisine and d-pseudoephedrine with N-(5-bromopyridin-2-yl)-2-bromoacetamide hydrobromide. The compositions and structures of the products were confirmed by IR\\u000a and PMR spectroscopy and mass spectrometry.

I. V. Kulakov

2010-01-01

400

The plant alkaloid usambarensine intercalates into DNA and induces apoptosis in human HL60 leukemia cells.  

PubMed

Usambarensine is a plant alkaloid isolated from the roots of Strychnos usambarensis collected in Central Africa. This bis-indole compound displays potent antiamoebic activities and shows antigardial, antimalarial and cytotoxic effects. Usambarensine is highly toxic to B16 melanoma cells and inhibits the growth of leukemia and carcinoma cells. To date, the molecular basis for its diverse biological effects remains totally unknown. However, its capacity to inhibit nucleic acids synthesis in melanoma cells, on the one hand, and its structural analogy with DNA-binding pyridoindole plant alkaloids recently studied (cryptolepine and matadine), on the other hand, suggested that usambarensine could also bind to DNA. Consequently, we studied the strength and mode of binding to DNA of usambarensine by means of absorption, circular and linear dichroism. The results of the optical measurements indicate that the alkaloid effectively binds to DNA and behaves as a typical intercalating agent. Biochemical experiments indicated that, in contrast to cryptolepine and matadine, usambarensine does not interfere with the catalytic activity of topoisomerase II. Human HL60 leukemia cells were used to assess the cytotoxicity of the alkaloid and its effect on the cell cycle. Usambarensine treatment is associated with a loss of cells in the G1 phase accompanied with a large increase in the sub-G1 region which is characteristic of apoptotic cells. The DNA of usambarensine-treated cells was severely fragmented and the proteolytic activity of DEVD-caspases is enhanced. Usambarensine is thus characterized as DNA intercalator inducing apoptosis in leukemia cells. PMID:10697543

Dassonneville, L; Wattez, N; Mahieu, C; Colson, P; Houssier, C; Frederich, M; Tits, M; Angenot, L; Bailly, C

1999-01-01

401

Genetic variation in constitutive and inducible pyrrolizidine alkaloid levels in Cynoglossum officinale L  

Microsoft Academic Search

The constitutive pyrrolizidine alkaloid (PA) concentration of both shoots and roots differed significantly between 17 selfed families. The broad-sense heritability accounted for 33–43% of the variation in PA levels. Families also differed significantly in the amount and the direction of PA induction in both shoots and roots, 24 h after punching 15 holes in the leaves. We found a significantly

Nicole M. van Dam; Klaas Vrieling

1994-01-01

402

Quantitative analysis of pyrrolizidine alkaloids sequestered from diverse host plants in Longitarsus flea beetles (Coleoptera, Chrysomelidae)  

Microsoft Academic Search

Summary.   Several species of the flea beetles genus Longitarsus are able to sequester pyrrolizidine alkaloids (PAs) from their host plants. In five Longitarsus species we compare the concentration of PAs present in their host plants belonging to the Asteraceae or Boraginaceae with\\u000a those found in the beetles. To get an estimate of the intrapopulation variability, three samples of five beetles

Wolf Haberer; Susanne Dobler

1999-01-01

403

Discorhabdins I and L, cytotoxic alkaloids from the sponge Latrunculia brevis.  

PubMed

Two cytotoxic alkaloids, discorhabdins L (1) and I (2), were isolated from Latrunculia brevis and their structures assigned on the basis of detailed spectroscopic analysis and comparison with the known metabolites discorhabdins R (5), D (6), and B (4). Compounds 1 and 2 showed strong in vitro cytotoxicity against a panel of 14 tumor cell lines. PMID:15043433

Reyes, Fernando; Martín, Rocío; Rueda, Ana; Fernández, Rogelio; Montalvo, David; Gómez, Cristina; Sánchez-Puelles, José M

2004-03-01

404

[Formation of alkaloids from Penicillium species fungi during growth on wheat kernels].  

PubMed

The ability to produce alkaloids has been studied in 13 strains belonging to 10 species of the genus Penicillium. Most of these strains produce identical ranges of alkaloids when grown on wheat grain and synthetic Abe medium. They are roquefortine, 3,12-dihydroroquefortine, and glandicolines A and B in strain P. chrysogenum VKM F-1987; fumigaclavines A and B, festuclavine, and pyroclasine in P. commune VKM F-308, F-3491, and KBP4; agroclavine 1 and epoxyagroclavine 1 in P. fellutanum VKM F-1073; fellutanine A in P. fellutanum F-3020; roquefortine, 3,12-dihydroroquefortine, meleagrin, and glandicolines A and B in P. glandicola VKM F-743; aurantioclavine in P. nalgiovense VKM F-229; isofumigaclavines A and B, festuclavine, roquefortine, and 3,12-dihydroroquefortine in P. roquefortii VKM F-2389; roquefortine, 3,12-dihydroroquefortine, and meleagrin in P. vitale VKM F-3624; roquefortine and oxaline in P. vulpinum VKM F-256; and alpha-cyclopiazonic acid and rugulovasine B in P. viridicatum C-47. No alkaloids were found in P. rugulosum VKM F-352 grown on wheat grain. A simple method is proposed for isolating alkaloids from affected grains. PMID:14520967

Vinokurova, N G; Bo?chenko, L V; Arinbasarov, M U

2003-01-01

405

Antibody binding of circulating ergot alkaloids in cattle grazing tall fescue.  

PubMed

Direct evidence linking alkaloids found in endophyte-infected tall fescue forage with the livestock disorder known as fescue toxicosis is lacking. Physiologic effects of fescue toxicosis include reduced serum prolactin concentration in cattle. A monoclonal antibody specific to the lysergic moiety of ergot alkaloids was developed in mice after creating an immunogen by linking lysergol to human serum albumin. The antibody was specific to the lysergic moiety and, therefore, it cross-reacted with ergot alkaloids, lysergic acid, and lysergol. The antibody did not cross-react with alkaloid derivatives that had bromated or hydrogenated lysergic ring moieties. Fescue toxicosis conditions were elicited in yearling Angus steers by permitting them to graze endophyte-infected tall fescue containing > 650 micrograms/kg of ergovaline for 60 days. Passive immunization of steers by infusion of the monoclonal antibody increased serum prolactin concentration by 7 ng/ml, beginning immediately after infusion. Control steers did not respond to treatment with bovine serum albumin. Active immunization of yearling Angus heifers with immunogens containing lysergol or ergonovine linked to human serum albumin resulted in an antibody response. PMID:8192270

Hill, N S; Thompson, F N; Dawe, D L; Stuedemann, J A

1994-03-01

406

Interspecific hybridization and bioactive alkaloid variation increases diversity in endophytic Epichloë species of Bromus laevipes.  

PubMed

Studying geographic variation of microbial mutualists, especially variation in traits related to benefits they provide their host, is critical for understanding how these associations impact key ecological processes. In this study, we investigate the phylogenetic population structure of Epichloë species within Bromus laevipes, a native cool-season bunchgrass found predominantly in California. Phylogenetic classification supported inference of three distinct Epichloë taxa, of which one was nonhybrid and two were interspecific hybrids. Inheritance of mating-type idiomorphs revealed that at least one of the hybrid species arose from independent hybridization events. We further investigated the geographic variation of endophyte-encoded alkaloid genes, which is often associated with key benefits of natural enemy protection for the host. Marker diversity at the ergot alkaloid, loline, indole-diterpene, and peramine loci revealed four alkaloid genotypes across the three identified Epichloë species. Predicted chemotypes were tested using endophyte-infected plant material that represented each endophyte genotype, and 11 of the 13 predicted alkaloids were confirmed. This multifaceted approach combining phylogenetic, genotypic, and chemotypic analyses allowed us to reconstruct the diverse evolutionary histories of Epichloë species present within B. laevipes and highlight the complex and dynamic processes underlying these grass-endophyte symbioses. PMID:25065688

Charlton, Nikki D; Craven, Kelly D; Afkhami, Michelle E; Hall, Bradley A; Ghimire, Sita R; Young, Carolyn A

2014-10-01

407

Chemotaxis disruption in Pratylenchus scribneri by tall fescue root extracts and alkaloids.  

PubMed

Tall fescue (Festuca arundinacea) forms a symbiotic relationship with the clavicipitalean fungal endophyte Neotyphodium coenophialum. Endophyte-infected grass is tolerant to nematode, but the factors responsible are unknown. One objective of this work was to determine if root extracts of tall fescue effected chemoreceptor activity of Pratylenchus scribneri by using an in vitro chemoreception bioassay. Another objective was to determine if specific ergot alkaloids (ergovaline, ergotamine, a-ergocryptine, ergonovine), and loline alkaloids, all produced by the fungal endophyte, altered chemotaxis with this bioassay. Methanolic extract from roots altered chemotaxis activities in this nematode but only from roots of plants cultured 45 > or = d, which repelled nematodes. Extracts prepared from noninfected grasses were attractants. This assay indicated that the alkaloids were either repellents or attractants. N-formylloline was an attractant at concentrations of 20 microg/ml and lower, while at higher concentrations it was a repellent. Ergovaline, the major ergot alkaloid produced by the endophyte, was repellent at both high and low concentrations and caused complete death of the nematodes. PMID:19575265

Bacetty, Ada A; Snook, Maurice E; Glenn, Anthony E; Noe, James P; Nagabhyru, Padmaja; Bacon, Charles W

2009-07-01

408

Diversity of pyrrolizidine alkaloids in Senecio species does not affect the specialist herbivore Tyria jacobaeae  

Microsoft Academic Search

The evolution of the diversity of related secondary metabolites in plants is still poorly understood. It is often thought that the evolution of plant secondary metabolites is driven by specialist insect herbivores and under this coevolutionary model it is expected that related compounds differ in their effects on specialist herbivores. Here we focus on the diversity of pyrrolizidine alkaloids (PAs)

Mirka Macel; Peter G. L. Klinkhamer; Klaas Vrieling; Ed van der Meijden

2002-01-01

409

Facilitation of memory retrieval by the “anti-addictive” alkaloid, ibogaine  

Microsoft Academic Search

Anecdotal observations in humans indicate that indole alkaloid ibogaine may have antiaddictive properties. It has been suggested that the therapeutic action of ibogaine may depend upon facilitated access to the past experiences, purportedly influencing the initiation of drug addiction. To determine if ibogaine may facilitate memory retrieval, rats were trained in the Morris maze spatial navigation task. It has been

Piotr Popik

1996-01-01

410

Identification of a WRKY Protein as a Transcriptional Regulator of Benzylisoquinoline Alkaloid Biosynthesis in Coptis japonica  

Microsoft Academic Search

Selected cultured Coptis japonica cells produce a large amount of the benzylisoquinoline alkaloid berberine. Previous studies have suggested that berberine productivity is controlled at the transcript level of biosynthetic genes. We have identified a regulator of transcription in berberine biosynthesis using functional genomics with a transient RNA interference (RNAi) and overexpression of the candidate gene. The 24 primary candidate clones

Nobuhiko Kato; Emilyn Dubouzet; Yasuhisa Kokabu; Sayumi Yoshida; Yoshimasa Taniguchi; Joseph Gogo Dubouzet; Kazufumi Yazaki; Fumihiko Sato

2007-01-01

411

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

PubMed Central

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 accompany vascular tissues throughout the plant. However, immunofluorescence labeling using affinity-purified antibodies showed that three key enzymes, (S)-N-methylcoclaurine 3?-hydroxylase (CYP80B1), berberine bridge enzyme (BBE), and codeinone reductase (COR), involved in the biosynthesis of morphine and the related antimicrobial alkaloid sanguinarine, are restricted to the parietal region of sieve elements adjacent or proximal to laticifers. The localization of laticifers was demonstrated using antibodies specific to the major latex protein (MLP), which is characteristic of the cell type. In situ hybridization showed that CYP80B1, BBE, and COR gene transcripts were found in the companion cell paired with each sieve element, whereas MLP transcripts were restricted to laticifers. The biosynthesis and accumulation of alkaloids in opium poppy involves cell types not implicated previously in plant secondary metabolism and dramatically extends the function of sieve elements beyond the transport of solutes and information macromolecules in plants. PMID:14508000

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

2003-01-01

412

Extraction Optimization of Tinospora cordifolia and Assessment of the Anticancer Activity of Its Alkaloid Palmatine  

PubMed Central

Objective. To optimize the conditions for the extraction of alkaloid palmatine from Tinospora cordifolia by using response surface methodology (RSM) and study its anticancerous property against 7,12-dimethylbenz(a)anthracene (DMBA) induced skin carcinogenesis in Swiss albino mice. Methods. The effect of three independent variables, namely, extraction temperature, time, and cycles was investigated by using central composite design. A single topical application of DMBA (100??g/100??L of acetone), followed 2 weeks later by repeated application of croton oil (1% in acetone three times a week) for 16 weeks, exhibited 100 percent tumor incidence (Group 2). Results. The highest yield of alkaloid from Tinospora cordifolia could be achieved at 16 hours of extraction time under 40°C with 4 extraction cycles. Alkaloid administration significantly decreases tumor size, number, and the activity of serum enzyme when compared with the control (Group 2). In addition, depleted levels of reduced glutathione (GSH), superoxide dismutase (SOD), and catalase and increased DNA damage were restored in palmatine treated groups. Conclusion. The data of the present study clearly indicate the anticancer potential of palmatine alkaloid in DMBA induced skin cancer model in mice. PMID:24379740

Ali, Huma; Dixit, Savita

2013-01-01

413

Direct analysis of quaternary alkaloids by in situ reactive desorption corona beam ionization MS.  

PubMed

The direct detection of quaternary alkaloids by atmospheric pressure chemical ionization (APCI)-base ambient MS is difficult because of their poor volatility. In this study, a reactive protocol was developed for the in situ determination of quaternary alkaloids using desorption corona beam ionization (DCBI) mass spectrometry (MS). The model compounds of 8 quaternary alkaloids including sanguinarine, chelerythrine, cyclanoline, nitidine, coptisine, jatrorrhizine, berberine, palmatine and 2 tertiary alkaloids including protopine and allocryptopine were investigated in different states such as on a polytetrafluoroethylene (PTFE) plate, in raw herbal materials, and in silica gel. After various reactive reagents were studied, the mixture of saturated aqueous NaOH solution and CH3OH solvent (3?:?7, v/v) was selected as the optimized reactive reagent for the reactive DCBI-MS detection. All the target molecules can be detected with high sensitivity. On a PTFE plate the limits of detection were 0.0795, 0.1060, 0.4860, 0.9665, 0.8879, 0.3987, 0.5557, 0.4591, 0.0889, and 0.1929 mg L(-1) for sanguinarine, chelerythrine, cyclanoline, nitidine, coptisine, jatrorrhizine, berberine, palmatine, protopine, and allocryptopine, respectively. The reactive protocol was also applied to the direct detection of raw herbal materials and thin layer chromatography successfully. PMID:25118336

Hou, Yulan; Wu, Tingting; Liu, Yaru; Wang, Hua; Chen, Yingzhuang; Chen, Bo; Sun, Wenjian

2014-10-21

414

Inducamides A-C, Chlorinated Alkaloids from an RNA Polymerase Mutant Strain of Streptomyces sp.  

PubMed

Inducamides A-C (1-3), three new chlorinated alkaloids featuring an amide skeleton generated by a tryptophan fragment and a 6-methylsalicylic acid unit, were isolated from a chemically induced mutant strain of Streptomyces sp. with the inducamides only being produced in the mutant strain. Their structures, including stereochemistry, were determined by spectroscopic analysis, Marfey's method, and CD spectroscopy. PMID:25338006

Fu, Peng; Jamison, Matthew; La, Scott; MacMillan, John B

2014-11-01

415

Coordinated regulation of two indole alkaloid biosynthetic genes from Catharanthus roseus by auxin and elicitors  

Microsoft Academic Search

Catharanthus roseus (periwinkle) produces a wide range of terpenoid indole alkaloids, including several pharmaceutically important compounds, from the intermediate strictosidine. The complete mRNA sequence for the enzyme strictosidine synthase (SSS) was determined. Comparison of the primary structure of the encoded protein with the amino-terminal sequence of purified SSS indicated the presence of a signal peptide of 31 amino acids in

Giancarlo Pasquali; Oscar J. M. Goddijn; Anthony Waal; Robert Verpoorte; Rob A. Schilperoort; J. Harry C. Hoge; Johan Memelink

1992-01-01

416

Erythrina mulungu Alkaloids Are Potent Inhibitors of Neuronal Nicotinic Receptor Currents in Mammalian Cells  

PubMed Central

Crude extracts and three isolated alkaloids from Erythrina mulungu plants have shown anxiolytic effects in different animal models. We investigated whether these alkaloids could affect nicotinic acetylcholine receptors and if they are selective for different central nervous system (CNS) subtypes. Screening experiments were performed using a single concentration of the alkaloid co-applied with acetylcholine in whole cell patch-clamp recordings in three different cell models: (i) PC12 cells natively expressing ?3* nicotinic acetylcholine receptors; (ii) cultured hippocampal neurons natively expressing ?7* nicotinic acetylcholine receptors; and (iii) HEK 293 cells heterologoulsy expressing ?4?2 nicotinic acetylcholine receptors. For all three receptors, the percent inhibition of acetylcholine-activated currents by (+)-11á-hydroxyerysotrine was the lowest, whereas (+)-erythravine and (+)-11á-hydroxyerythravine inhibited the currents to a greater extent. For the latter two substances, we obtained concentration-response curves with a pre-application protocol for the ?7* and ?4?2 nicotinic acetylcholine receptors. The IC50 obtained with (+)-erythravine and (+)-11á-hydroxyerythravine were 6 µM and 5 µM for the ?7* receptors, and 13 nM and 4 nM for the ?4?2 receptors, respectively. Our data suggest that these Erythrina alkaloids may exert their behavioral effects through inhibition of CNS nicotinic acetylcholine receptors, particularly the ?4?2 subtype. PMID:24349349

Setti-Perdigao, Pedro; Serrano, Maria A. R.; Flausino, Otavio A.; Bolzani, Vanderlan S.; Guimaraes, Marilia Z. P.; Castro, Newton G.

2013-01-01

417

Chrotacumines G-J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity.  

PubMed

Four new chromone alkaloids, chrotacumines G-J (1-4), have been isolated from the barks of Dysoxylum acutangulum. Their structures and absolute configurations were elucidated on the basis of NMR and CD data. Chrotacumines G and J (1 and 4) showed osteoclast differentiation inhibitory activity in a dose dependent manner. PMID:24767841

Morita, Hiroshi; Nugroho, Alfarius Eko; Nagakura, Yuta; Hirasawa, Yusuke; Yoshida, Haruka; Kaneda, Toshio; Shirota, Osamu; Ismail, Intan Safinar

2014-06-01

418

Colorimetric and spectrophotometric determination of total and non-phenolic alkaloids in ipeca and its formulations.  

PubMed

A simple method, requiring no chromatographic separation, is presented for the determination of the total and non-phenolic alkaloids in ipeca and its preparations. The complex formed between the alkaloid and methyl orange at pH 5.0 is extracted with chloroform and treated with 0.1N NaOH. The liberated dye, determined at 460 nm, is a measure of the total alkaloids. The chloroform phase remaining is treated with 0.1N H2SO4, and the acid extract is measured at 283 nm for the non-phenolic alkaloids, calculated as emetine. The proposed method was successfully applied to samples of ipeca powder, ipeca tincture, and 3 British Pharmaceutical Codex mixtures containing ipeca tincture, namely, ipecacuanha mixture, pediatric; ipecacuanha and ammonia mixture, pediatric; and belladonna and ipecacuanha mixture, pediatric. The proposed method compares favorably with the Egyptian Pharmacopoeia, British Pharmacopoeia, and USP methods and has a relative standard deviation of 1.54%. The present procedure is less time-consuming and requires about 45 and 90 min for the assay of ipeca tincture and powder, respectively. Only a small sample (0.2 mL tincture of 1.0 g powder) is required. PMID:43328

Saleh, M R; El-Masry, S; El-Shaer, N

1979-09-01

419

Pyrrolizidine Alkaloids as Oviposition Stimulants for the Cinnabar Moth, Tyria jacobaeae  

Microsoft Academic Search

In choice experiments with artificial leaves, we tested related pyrrolizidine alkaloids (PAs) for their stimulatory effects on the oviposition of the cinnabar moth, a specialist on the PA-containing plant Senecio jacobaea. The PAs from S. jacobaea that we tested stimulated oviposition. Monocrotaline also stimulated oviposition although this PA is not found in plants of the genus Senecio. The moths preferred

Mirka Macel; Klaas Vrieling

2003-01-01

420

Enantioselective synthesis in carbohydrate-based drug discovery: imino sugars, alkaloids and macrolide antibiotics.  

PubMed

This review is dedicated to enantioselective methods for the generation of carbohydrate-based lead compounds for drug research. Selected examples encompassing imino sugars, bicyclic imino sugar-type alkaloids such as castanospermine, swainsonine, or alexine, as well as macrolide glycosides are covered and discussed. PMID:24758433

Xavier, Nuno M; Rauter, Amélia P

2014-01-01

421

The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in Jacobaea vulgaris  

Microsoft Academic Search

Secondary metabolites such as pyrrolizidine alkaloids (PAs) play a crucial part in plant defense. PAs can occur in plants in two forms: tertiary amine (free base) and N-oxide. PA extraction and detection are of great importance for the understanding of the role of PAs as plant defense compounds, as the tertiary PA form is known for its stronger influence on

Lotte Joosten; Dandan Cheng; Patrick P. J. Mulder; Klaas Vrieling; Johannes A. van Veen; Peter G. L. Klinkhamer

2011-01-01

422

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

E-print Network

extracto alcaloideo. 1 Laboratory of Natural Product and Organic Synthesis, Department of Chemistry). Quinolizidine alkaloids have proved to have an important role as herbivore repellents, and inhibit the growth of various bacteria and fungi pro- viding protection to the plants from herbi- vores such as insects

Paré, Paul W.

423

Lycopladine H, a novel alkaloid with fused-tetracyclic skeleton from Lycopodium complanatum  

Microsoft Academic Search

A novel Lycopodium alkaloid, lycopladine H (1), with a fused-tetracyclic ring system consisting of an azocane ring connected to a [2,2,2]-bicyclooctane ring and a 3-piperidone ring, was isolated from the club moss Lycopodium complanatum. The structure and relative stereochemistry of 1 were elucidated on the basis of spectroscopic data.

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

2009-01-01

424

Lycopladines B-D and lyconadin B, new alkaloids from Lycopodium complanatum.  

PubMed

Four new alkaloids, lycopladines B-D (1-3) and lyconadin B (4), have been isolated from the club moss Lycopodium complanatum and the structures including the stereochemistry were elucidated on the basis of spectral data and modified Mosher's method. Lyconadin B (4) elevated NGF mRNA expression in 1321N1 human astrocytoma cells. PMID:16750373

Ishiuchi, Kan'ichiro; Kubota, Takaaki; Hoshino, Tomohiro; Obara, Yutaro; Nakahata, Norimichi; Kobayashi, Jun'ichi

2006-09-01

425

Lycopladines B–D and lyconadin B, new alkaloids from Lycopodium complanatum  

Microsoft Academic Search

Four new alkaloids, lycopladines B–D (1–3) and lyconadin B (4), have been isolated from the club moss Lycopodium complanatum and the structures including the stereochemistry were elucidated on the basis of spectral data and modified Mosher’s method. Lyconadin B (4) elevated NGF mRNA expression in 1321N1 human astrocytoma cells.

Kan’ichiro Ishiuchi; Takaaki Kubota; Tomohiro Hoshino; Yutaro Obara; Norimichi Nakahata; Jun’ichi Kobayashi

2006-01-01

426

Expression Profiling of Heat Stress Effects on Mice Fed Ergot Alkaloids  

Microsoft Academic Search

Fescue toxicosis affects wild and domestic animals consuming ergot alkaloids contained in tall fescue forage infected with the endophytic fungus, Neotyphodium coenophialum. When animals are consuming infected fescue (E+) forage during periods of elevated ambient temperatures (summer), a range of phenotypic disorders collectively called summer slump is observed. It is characterized by hyperthermia, with an accompanying decrease in feed intake,

Sachin Bhusari; Zhilin Liu; Leonard B. Hearne; Donald E. Spiers; William R. Lamberson; Eric Antoniou

2007-01-01

427

Production of alkaloids by in vitro culture of Erythrina americana Miller  

Microsoft Academic Search

The production of erythroidines and other alkaloids was studied in cotyledons, callus and cell suspension cultures of Erythrina americana Miller. The cell suspension cultures, grown in Murashige & Skoog medium with naphthaleneacetic acid (3 mg l-1) and kinetin (2 mg l-1), produced 89 and 17 µg a- and ß-erythroidines respectively per g dry wt.

Rubén San Miguel-Chávez; Marcos Soto-Hernández; Ana C. Ramos-Valdivia; Geoffrey Kite; Mariano Martínez-Vázquez; Ma. del Rosario M. García; Teresa S. Terrazas

2003-01-01

428

Cyclopamine and related steroidal alkaloid teratogens: their occurrence, structural relationship, and biologic effects.  

PubMed

A spontaneous congenital deformity is produced in lambs whose dams consume Veratrum californicum on the 14th day of gestation. The deformity is generally expressed as cyclopia, cebocephaly, anophthalmia, or microphthalmia. This teratogenic effect is produced by certain steroidal alkaloid teratogens from the plant - most notably the compound cyclopamine. Cyclopamine is a C-nor-D-homo steroid with fused furanopiperidine rings E and F at right angles to the plane of the steroid because of spiro attachment at C-17 of the steroid. Among veratrum alkaloids, only those with an intact furan ring E were teratogenic in sheep, whereas those in which the peperidine ring is not rigidly positioned at right angles to the steroid were not. Many ruminants and laboratory animals are susceptible to the teratogen. It has wide species and tissue specificity and appears to have a direct effect on the embryo, not as a consequence of metabolic alteration of its structure nor as an indirect effect through a maternal influence. Other plant sources, notably potatoes, tomatoes, and eggplant contain related spirosolane steroidal alkaloids. Among naturally occurring spirosolanes, solasodine is teratogenic in hamsters, but neither tomatidine not diosgenin, the non-nitrogen containing analog of solasodine, is teratogenic. Results of these and other studies suggest that a basic nitrogen positioned alpha with respect to the steroidal plane and at appropriate distance beyond the D ring confers the teratogenicity on the molecule. Potato sprouts with high alkaloid content are teratogenic in hamsters, but tubers and peels are not. PMID:723484

Keeler, R F

1978-10-01

429

Isariotins A-D, alkaloids from the insect pathogenic fungus Isaria tenuipes BCC 7831.  

PubMed

Isariotins A-D (1- 4), alkaloids possessing a unique bicyclo[3.3.1]nonane ring, were isolated from the insect pathogenic fungus Isaria tenuipes BCC 7831. The structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses. PMID:17822299

Haritakun, Rachada; Srikitikulchai, Prasert; Khoyaiklang, Punsa; Isaka, Masahiko

2007-09-01

430

A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (-)-cermizine B.  

PubMed

The synthesis of the Lycopodium alkaloid (-)-cermizine B (1), which establishes its absolute configuration, is achieved by combining asymmetric organocatalysis and an uninterrupted eight-step reaction sequence, followed by a final reduction step. This "pot-economy" strategy provides access to the cis-phlegmarine stereoparent embedded in 1 for the first time, rapidly and on a gram-scale. PMID:24727855

Bradshaw, Ben; Luque-Corredera, Carlos; Bonjoch, Josep

2014-07-11

431

Enhanced productivity of tropane alkaloids and fertility in artificial autotetraploids of Hyoscyamus niger L  

Microsoft Academic Search

Genetically stable artificial autotetraploids with over 90% seed set were obtained by colchicine treatment of the solanaceous species Hyoscyamus niger L. (2n=4x=68). The tetraploids were vigorous and yielded 22.5% more tropane alkaloid per individual than the source diploids.

U. C. Lavania; Sangeeta Srivastava

1991-01-01

432

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

PubMed Central

The anticancer agents vinblastine and vincristine are bisindole alkaloids derived from coupling vindoline and catharanthine, monoterpenoid indole alkaloids produced exclusively by Madagascar periwinkle (Catharanthus roseus) plants. 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 improve alkaloid content or provide alternative sources of the bisindole alkaloids ultimately rely on the isolation and characterization of the genes involved. Several vindoline biosynthetic genes have been isolated, and the cellular and subcellular organization of the corresponding enzymes has been well studied. However, due to the leaf-specific localization of vindoline biosynthesis, and the lack of production of this precursor in cell suspension and hairy root cultures of C. roseus, further elucidation of this pathway demands the development of reverse genetics approaches to assay gene function in planta. The bipartite pTRV vector system is a Tobacco Rattle Virus-based virus-induced gene silencing (VIGS) platform that has provided efficient and effective means to assay gene function in diverse plant systems. We have developed a VIGS method to investigate gene function in C. roseus plants using the pTRV vector system. The utility of this approach in understanding gene function in C. roseus leaves is demonstrated by silencing known vindoline biosynthetic genes previously characterized in vitro. PMID:21802100

Liscombe, David K.; O'Connor, Sarah E.

2011-01-01

433

Cellular localization of quinolizidine alkaloids by laser desorption mass spectrometry (LAMMA 1000).  

PubMed

Stem sections of Lupinus polyphyllus and Cytisus scoparius have been analyzed for the distribution of quinolizidine alkaloids by laser desorption mass spectrometry, employing a LAMMA 1000 instrument. Sparteine and lupanine could be recorded and were found to be restricted to the epidermis and probably also to the neighbouring 1 or 2 subepidermal cell layers. PMID:24253573

Wink, M; Heinen, H J; Vogt, H; Schiebel, H M

1984-12-01

434

Steroidal alkaloids in tissue cultures and regenerated plants of Solanum dulcamara  

Microsoft Academic Search

Callus and cell suspension cultures were established with shoots of the soladulcidine variety of the bittersweet Solanum dulcamara L. Plantlets were regenerated from undifferentiated callus. From mixotrophic callus as well as mixotrophic suspension cultures soladulicidine, solasodine and the corresponding neutral spirostanes tigogenin and diosgenin were isolated and identified by thin layer chromatography and mass spectrometry. Total alkaloid concentrations were about

A. Emke; U. Eilert

1986-01-01

435

Alkaloids of the herb sedum acre L. Part II: Separation by countercurrent distribution  

Microsoft Academic Search

Component alkaloids of Sedum acre L. (stonecrop) were partly separated on preparative scale by countercurrent distribution, using selective solvent systems of the type chloroform\\/buffer solution and benzene\\/buffer solution, the optimal pH of the aqueous phase being estimated from paper chromatographic data. Good agreement between predicted and experimental separations was observed.

S. Bieganowska; A. Waksmundzki

1976-01-01

436

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

E-print Network

for testing the state of synthetic effi- ciency (Fig. 1). It is the eponymous member of a family of alkaloids are as toxic to these animals as nicotine, they seem to have relatively few negative effects on mammalian herbivores, including horses. In fact, the toxic affects occasionally associated with tall fescue have been

Trauner, Dirk

437

Curvulamine, a new antibacterial alkaloid incorporating two undescribed units from a curvularia species.  

PubMed

The white croaker (Argyrosomus argentatus) derived Curvularia sp. IFB-Z10 produces curvulamine as a skeletally unprecedented alkaloid incorporating two undescribed extender units. Curvulamine is more selectively antibacterial than tinidazole and biosynthetically unique in the new extenders formed through a decarboxylative condensation between an oligoketide motif and alanine. PMID:25286294

Han, Wen Bo; Lu, Yan Hua; Zhang, Ai Hua; Zhang, Gao Fei; Mei, Ya Ning; Jiang, Nan; Lei, Xinxiang; Song, Yong Chun; Ng, Seik Weng; Tan, Ren Xiang

2014-10-17

438

Alterations in osmoregulation, antioxidant enzymes and indole alkaloid levels in Catharanthus roseus exposed to water deficit  

Microsoft Academic Search

Catharanthus roseus (L.) G. Don plants were grown in different water regimes in order to study the drought induced osmotic stress and proline (PRO) metabolism, antioxidative enzyme activities and indole alkaloid accumulation. The plants under pot culture were subjected to 10, 15 and 20 days interval drought (DID) stress from 30 days after sowing (DAS) and regular irrigation was kept

C. Abdul Jaleel; P. Manivannan; A. Kishorekumar; B. Sankar; R. Gopi; R. Somasundaram; R. Panneerselvam

2007-01-01

439

Pharmacology of ephedra alkaloids and caffeine after single-dose dietary supplement use  

Microsoft Academic Search

Objective: Serious cardiovascular toxicity has been reported in people taking dietary supplements that contain ma huang (Ephedra) and guarana (caffeine). We assessed the pharmacokinetics and pharmacodynamics of a dietary supplement that contains these herbal stimulants.Methods: Eight healthy adults received a single oral dose of a thermogenic dietary supplement labeled to contain 20 mg ephedrine alkaloids and 200 mg caffeine after

Christine A. Haller; Peyton Jacob; Neal L. Benowitz

2002-01-01

440

Influences of Fructus evodiae pretreatment on the pharmacokinetics of Rhizoma coptidis alkaloids  

Microsoft Academic Search

Ethnopharmacological relevanceRhizoma coptidis is a traditional Chinese medicine with pharmacological properties. It is usually prescribed with Fructus evodiae as traditional Chinese medicine (TCM) formulas. Here we report the influences of Fructus evodiae on the pharmacokinetics of the Rhizoma coptidis alkaloids and propose possible mechanisms.

Bing-Liang Ma; Meng-Kan Yao; Xiang-Hui Han; Yue-Ming Ma; Jia-Sheng Wu; Chang-Hong Wang

2011-01-01

441

Determination of protoberberine alkaloids in Rhizoma Coptidis by ERETIC 1H NMR method  

Microsoft Academic Search

An alternative quantification approach called ERETIC (Electronic REference To access In vivo Concentrations) utilizing electronic reference-based proton nuclear magnetic resonance (1H NMR) spectroscopy techniques has been successfully introduced in our present study to simultaneously determine the contents of five major active protoberberine alkaloids (berberine, coptisine, jatrorrhizine, palmatine and epiberberine) in Rhizoma Coptidis, one of the most commonly used traditional Chinese

Pei-Lan Ding; Li-Qin Chen; Yang Lu; Yong-Guo Li

442

[Microcalorimetric investigation on the interaction of six alkaloids from rhizoma coptidis].  

PubMed

How to identify active constituents of traditional Chinese medicines (TCMs) and study their interactions are key problems in the development of TCMs. The inhibitory effect of six alkaloids from Rhizoma Coptidis (RC) on Shigella dysenteriae (S. dysenteria) growth had been investigated by microcalorimetry in this study. Main active constituents of RC were confirmed by comparing their contributions to the bacteriostatic effect, and the interactions among active constituents were further researched. According to the result, in 0.8 mg-mL-1 extract of RC, the contributions of six active alkaloids including berberine, coptisine, epiberberine, palmatine and the combination of jatrorrhizine and columbamine were 52.83%, 36.31%, 2.49%, 4.27% and 3.21%, respectively. Therefore, berberine and coptisine were the main active constituents of RC that inhibited the growth of S. dysenteria. The study of interactions among the six alkaloids indicated that, 1 there were some contstituents antagonizing the inhibitory effect of RC, 2 there was a synergy effect between berberine and coptisine, 3 there were additive effects between other four alkaloids and the main active constituents. These results may provide some useful references for the establishment of the quality standard for RC and the development of multi-component TCMs. PMID:24689238

Li, Jun-Xian; Wang, Jia-Yi; Zhang, Le-Le; Yan, Dan; Wang, Rui-Lin; Li, Bao-Cai; Xiao, Xiao-He

2013-12-01

443

Polymorphic Nucleic Acid Binding of Bioactive Isoquinoline Alkaloids and Their Role in Cancer  

PubMed Central

Bioactive alkaloids occupy an important position in applied chemistry and play an indispensable role in medicinal chemistry. Amongst them, isoquinoline alkaloids like berberine, palmatine and coralyne of protoberberine group, sanguinarine of the benzophenanthridine group, and their derivatives represent an important class of molecules for their broad range of clinical and pharmacological utility. In view of their extensive occurrence in various plant species and significantly low toxicities, prospective development and use of these alkaloids as effective anticancer agents are matters of great current interest. This review has focused on the interaction of these alkaloids with polymorphic nucleic acid structures (B-form, A-form, Z-form, HL-form, triple helical form, quadruplex form) and their topoisomerase inhibitory activity reported by several research groups using various biophysical techniques like spectrophotometry, spectrofluorimetry, thermal melting, circular dichroism, NMR spectroscopy, electrospray ionization mass spectroscopy, viscosity, isothermal titration calorimetry, differential scanning calorimetry, molecular modeling studies, and so forth, to elucidate their mode and mechanism of action for structure-activity relationships. The DNA binding of the planar sanguinarine and coralyne are found to be stronger and thermodynamically more favoured compared to the buckled structure of berberine and palmatine and correlate well with the intercalative mechanism of sanguinarine and coralyne and the partial intercalation by berberine and palmatine. Nucleic acid binding properties are also interpreted in relation to their anticancer activity. PMID:20814427

Maiti, Motilal; Kumar, Gopinatha Suresh

2010-01-01

444

Improved detection of Coptidis alkaloids by field-amplified sample stacking in capillary electrophoresis  

Microsoft Academic Search

To improve the on-line detection of Coptidis alkaloids in capillary electrophoresis the field-amplified sample stacking was studied for them. In this work the peak height enhancements of stacking with hydrodynamic and electrokinetic injections were compared with respect to the conventional sample injection. It was found that the stacking efficiency of electrokinetic injection was more than ten times greater than that

Shao-Wen Sun; Hua-Ming Tseng

2004-01-01

445

Crotalaria medicaginea associated with horse deaths in northern Australia: new pyrrolizidine alkaloids.  

PubMed

Crotalaria medicaginea has been implicated in horse poisoning in grazing regions of central-west Queensland, which resulted in the deaths of more than 35 horses from hepatotoxicosis in 2010. Liver pathology was suggestive of pyrrolizidine alkaloidosis, and we report here the isolation of two previously uncharacterized pyrrolizidine alkaloids from C. medicaginea plant specimens collected from pastures where the horses died. The first alkaloid was shown by mass spectometric and NMR analyses to be 1?,2?-epoxy-7?-hydroxy-1?-methoxymethyl-8?-pyrrolizidine, which, like other alkaloids previously isolated from C. medicaginea, lacks the requisite functionality for hepatotoxcity. The second alkaloid isolated in this investigation was a new macrocyclic diester of otonecine, which we have named cromedine. The (1)H and (13)C NMR spectra of cromedine were fully assigned by 2D NMR techniques and allowed the constitution of the macrocyclic diester to be assigned unambiguously. C. medicaginea specimens implicated in this investigation do not belong to any of the three recognized Australian varieties (C. medicaginea var. neglecta, C. medicaginea var. medicaginea, and C. medicaginea var. linearis) and appear to be a local variant or form, referred to here as C. medicaginea (chemotype cromedine). PMID:21899365

Fletcher, Mary T; Hayes, Patricia Y; Somerville, Michael J; De Voss, James J

2011-11-01

446

Direct determination of alkaloid contents in Fumaria species by GC-MS.  

PubMed

The isoquinoline alkaloids protopine, cryptopine, sinactine, stylopine, bicuculline, adlumine, parfumine, fumariline, fumarophycine, fumaritine, dihydrofumariline, parfumidine and dihydrosanguinarine have been determined and identified by gas chromatography-mass spectrometry in Fumaria agraria, F. bastardii, F. capreolata, F. sepium, F. densiflora, F. faurei, F. officinalis subsp. officinalis, F. parviflora, F. petteri subsp. calcarata and F. macrosepala. The chemotaxonomic significance of the results is discussed. PMID:12494757

Suau, R; Cabezudo, B; Rico, R; Nájera, F; López-Romero, J M

2002-01-01

447

High performance liquid chromatography of selected alkaloids in ion-exchange systems.  

PubMed

A HPLC procedure on strong cation exchange column (SCX) has been developed for the analysis of selected alkaloids from different chemical groups. The retention, separation selectivity, symmetry of peaks and system efficiency were examined in different eluent systems containing different types or concentrations of buffers at various pH and the addition of organic modifiers: methanol (MeOH), acetonitrile (CH3CN), tetrahydrofuran (THF) or dioxane (Dx). The retention factors as the function of the concentration of buffers, the mobile phase pH and the percentage of modifier in the eluents were investigated. More symmetrical peaks and the highest theoretical plate number were obtained in eluents containing acetonitrile or tetrahydrofuran. In most cases, the increase of buffer concentration caused the decrease of alkaloids' retention, the improvement of peaks' symmetry and the increase of theoretical plate number. The improved peak symmetry and the efficiency of system for most investigated alkaloids were observed in the systems containing buffers at strongly acidic pH. The obtained results also reveal a large influence of salt cation used for buffer preparation. The results obtained on SCX column were compared with those obtained on a C18 column. The most efficient and selective systems were used for the separation of alkaloid standard mixture. PMID:24007682

Petruczynik, Anna; Waksmundzka-Hajnos, Monika

2013-10-11

448

Alkaloid presence and brine shrimp (Artemia salina) bioassay of medicinal species of eastern Nicaragua.  

PubMed

We used an alkaloid test and a brine shrimp bioassay to assess the bioactivity of the medicinal plants used by eastern Nicaraguan healers in traditional medicine. Ethnomedicinal uses were obtained from interviews of traditional healers. Aqueous extracts derived from 30 species of angiosperms were assayed for the presence of alkaloids and toxicity. Species tested are distributed in 30 genera and 21 families. Of the 30 species tested for alkaloids with Dragendorff's reagent, 29 contained alkaloids. Toxicological analysis was conducted using the brine shrimp lethal assay (BSLA). Biological activity using BSLA was recorded as the median lethal concentration (LC50) that kills 50% of the larvae within 24 h of contact with the aqueous plant extracts. The LC50 of the shrimp was less than 2500 microg/mL for 3 (10%) species, 2500-5000 microg/mL for 9 (30%), 5001-7500 microg/mL for 7 (23%), 7501-10000 microg/mL for 3 (10%), and greater than 10000 microg/mL for 8 (27%) of the species. The members of the orders Santales and Rubiales in general contained species with greater toxicity than any other group. Struthanthus cassythoides (Struthanthus cassythoides Millsp.(Loranthaceae)). (LC50 1574 microg/mL) and Alibertia edulis (Rich.) A. Rich. (Rubiaceae) (LC50 1741 microg/mL) were the most toxic. PMID:20645724

Coe, Felix G; Parikh, Dimpi M; Johnson, Caley A

2010-04-01

449

Alkaloid analysis by high-performance liquid chromatography-solid phase extraction-nuclear magnetic resonance: new strategies going beyond the standard.  

PubMed

The hyphenated technique HPLC-SPE-NMR is an important tool for rapid dereplication of complex mixtures of in particular small molecules and has been successfully employed in natural product research. However, positively charged alkaloids at low pH are often poorly trapped on the generally used SPE cartridge limiting the general application of the procedure. In this work, two new approaches for efficient SPE trapping of alkaloids and elution efficiencies were evaluated using 24 model alkaloids. Use of a 0.1 M NaOH solution as the post-column dilution greatly enhanced trapping of alkaloids on the commonly used cartridge containing divinylbenzene polymer (GP resin). This procedure, however, was unsuitable for trapping phenolic alkaloids. Severe line broadening and immiscibility with water made chloroform-d(1) unsuited as eluent. None of these problems occurred when methanol-d(4) was used as eluent. Previously, mixed mode cation exchange sorbents have not been used in HPLC-SPE-NMR analysis of natural products. In contrast to GP resin this material showed good retention and elution characteristics for retention and elution of alkaloids. As well the use of methanol-d(4) containing 1% aqueous NaOD (40%) as methanol-d(4) containing 5% aqueous NH(4)OH (30%) as eluents were successful, even though elution of alkaloids with pK(a) of the corresponding acid above 10 proved difficult. Alkaloid extracts of Huperzia selago containing complex aliphatic alkaloids and Triclisia patens containing bisbenzylisoquinoline alkaloids were used for validation of the protocols for analysis of a diverse collection of alkaloids. Mixed mode cation exchange sorbent was efficient for trapping and elution of both types of alkaloids as evidenced by acquisition of 2D NMR data for all trapped compounds. In contrast, GP resin proved only viable for all the H. selago alkaloids whereas trapping and elution of bisbenzylisoquinoline alkaloids were dubious. PMID:23195707

Johansen, Kenneth T; Ebild, Sarah J; Christensen, S Brøgger; Godejohann, Markus; Jaroszewski, Jerzy W

2012-12-28

450

Integration of Transcriptome, Proteome and Metabolism Data Reveals the Alkaloids Biosynthesis in Macleaya cordata and Macleaya microcarpa  

PubMed Central

Background The Macleaya spp., including Macleaya cordata and Macleaya microcarpa, are traditional anti-virus, inflammation eliminating, and insecticide herb medicines for their isoquinoline alkaloids. They are also known as the basis of the popular natural animal food addictive in Europe. However, few studies especially at genomics level were conducted on them. Hence, we performed the Macleaya spp. transcriptome and integrated it with iTRAQ proteome analysis in order to identify potential genes involved in alkaloids biosynthesis. Methodology and Principal Findings We elaborately designed the transcriptome, proteome and metabolism profiling for 10 samples of both species to explore their alkaloids biosynthesis. From the transcriptome data, we obtained 69367 and 78255 unigenes for M. cordata and M. microcarpa, in which about two thirds of them were similar to sequences in public databases. By metabolism profiling, reverse patterns for alkaloids sanguinarine, chelerythrine, protopine, and allocryptopine were observed in different organs of two species. We characterized the expressions of enzymes in alkaloid biosynthesis pathways. We also identified more than 1000 proteins from iTRAQ proteome data. Our results strongly suggest that the root maybe the organ for major alkaloids biosynthesis of Macleaya spp. Except for biosynthesis, the alkaloids storage and transport were also important for their accumulation. The ultrastructure of laticifers by SEM helps us to prove the alkaloids maybe accumulated in the mature roots. Conclusions/Significance To our knowledge this is the first study to elucidate the genetic makeup of Macleaya spp. This work provides clues to the identification of the potential modulate genes involved in alkaloids biosynthesis in Macleaya spp., and sheds light on researches for non-model medicinal plants by integrating different high-throughput technologies. PMID:23326424

Liu, Fuqing; Huang, Peng; Zhu, Pengcheng; Chen, Jinjun; Shi, Mingming; Guo, Fang; Cheng, Pi; Zeng, Jing; Liao, Yifang; Gong, Jing; Zhang, Hong-Mei; Wang, Depeng; Guo, An-Yuan; Xiong, Xingyao

2013-01-01

451

Staphylococcal Enterotoxin A Gene-Carrying Staphylococcus aureus Isolated from Foods and Its Control by Crude Alkaloid from Papaya Leaves.  

PubMed

Staphylococcus aureus is a known pathogen causing intoxication by producing enterotoxins in food. Staphylococcal enterotoxin A is one of the enterotoxins commonly implicated in staphylococcal food poisoning. The ability of crude alkaloid extract from papaya leaves to inhibit the growth of S. aureus and staphylococcal enterotoxin A synthesis was investigated. Staphylococcal enterotoxin A gene-carrying S. aureus was isolated from raw milk and ready-to-eat foods. Crude alkaloid was extracted from ground, dried papaya leaves using ultrasonic-assisted extraction, and a MIC of the alkaloid was determined by the broth macrodilution method. Furthermore, S. aureus isolate was exposed to the crude alkaloid extract at one- and twofold MIC, and the expression of sea was subsequently analyzed using a quantitative reverse transcription real-time PCR. Ten isolates of S. aureus were obtained, and nine of those isolates were sea carriers. The yield of crude alkaloid extract was 0.48 to 1.82% per dry weight of papaya leaves. A MIC of crude alkaloid to S. aureus was 0.25 mg/ml. After exposure to the alkaloid at 0.25 and 0.5 mg/ml for 2 h, a significant increase in cycle threshold values of sea was observed. The sea was expressed 29 and 41 times less when S. aureus was exposed to crude alkaloid at one- and twofold MIC, respectively. This study revealed that crude alkaloid of papaya leaves could control staphylococcal enterotoxin A gene-carrying S. aureus by suppressing the expression of sea, in addition to the ability to inhibit the growth of S. aureus. The expression of sea was successfully quantified. PMID:25364936

Handayani, Lita; Faridah, Didah Nur; Kusumaningrum, Harsi D

2014-11-01

452

Visualizing a plant defense and insect counterploy: alkaloid distribution in Lobelia leaves trenched by a plusiine caterpillar.  

PubMed

Insects that feed on plants protected by latex canals often sever leaf veins or cut trenches across leaves before feeding distal to the cuts. The insects thereby depressurize the canals and reduce latex exudation at their prospective feeding site. How the cuts affect the distribution and concentration of latex chemicals was not known. We modified a microwave-assisted extraction technique to analyze the spatial distribution of alkaloids in leaves of Lobelia cardinalis (Campanulaceae) that have been trenched by a plusiine caterpillar, Enigmogramma basigera (Lepidoptera: Noctuidae). We produced sharp two dimensional maps of alkaloid distribution by microwaving leaves to transfer alkaloids to TLC plates that were then sprayed with Dragendorff's reagent to visualize the alkaloids. The leaf prints were photographed and analyzed with image processing software for quantifying alkaloid levels. A comparison of control and trenched leaves documented that trenching reduces alkaloid levels by approximately 50% both distal and proximal to the trench. The trench becomes greatly enriched in alkaloids due to latex draining from surrounding areas. Measurements of exudation from trenched leaves demonstrate that latex pressures are rapidly restored proximal, but not distal to the trench. Thus, the trench serves not only to drain latex with alkaloids from the caterpillar's prospective feeding site, but also to isolate this section, thereby preventing an influx of latex from an extensive area that likely extends beyond the leaf. Microwave-assisted extraction of leaves has potential for diverse applications that include visualizing the impact of pathogens, leaf miners, sap-sucking insects, and other herbivores on the distribution and abundance of alkaloids and other important defensive compounds. PMID:19468794

Oppel, Craig B; Dussourd, David E; Garimella, Umadevi

2009-06-01

453

Two new protopines argemexicaines A and B and the anti-HIV alkaloid 6-acetonyldihydrochelerythrine from formosan Argemone mexicana.  

PubMed

Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[ c]phenanthridine (+/-)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 microg/mL and 14.6, respectively. PMID:12624820

Chang, Yuh-Chwen; Hsieh, Pei-Wen; Chang, Fang-Rong; Wu, Ru-Rong; Liaw, Chih-Chuang; Lee, Kuo-Hsiung; Wu, Yang-Chang

2003-02-01

454

Enzymatic and Chemo-Enzymatic Approaches Towards Natural and Non-Natural Alkaloids: Indoles, Isoquinolines, and Others  

NASA Astrophysics Data System (ADS)

The multi-step enzyme catalysed biosyntheses of monoterpenoid indole and isoquinoline alkaloids are described. Special emphasis is placed on those pathways leading to alkaloids of pharmacological and medicinal significance which have been fully elucidated at the enzyme level. The successful identification and cloning of cDNAs of single enzymes and their application provides great opportunities to develop novel strategies for both in vitro and in vivo alkaloid production in whole plants or tissue cultures, as well as in microbial systems such as Escherichia coli and yeast.

Stöckigt, Joachim; Chen, Zhong; Ruppert, Martin

455

Structure–activity relationships and the cytotoxic effects of novel diterpenoid alkaloid derivatives against A549 human lung carcinoma cells  

Microsoft Academic Search

The cytotoxicity of three alkaloids from the roots of Aconitum yesoense var. macroyesoense as well as 36 semi-synthetic C20-diterpenoid atisine-type alkaloid derivatives against A549 human lung carcinoma cells was examined. Ten acylated alkaloid\\u000a derivatives, pseudokobusine 11-veratroate (9), 11-anisoate (12), 6,11-dianisoate (14), 11-p-nitrobenzoate (18), 11,15-di-p-nitrobenzoate (22), 11-cinnamate (25) and 11-m-trifluoromethylbenzoate (27), and kobusine 11-p-trifluoromethylbenzoate (35), 11-m-trifluoromethylbenzoate (36) and 11,15-di-p-nitrobenzoate (39), exhibited

Koji Wada; Masaharu Hazawa; Kenji Takahashi; Takao Mori; Norio Kawahara; Ikuo Kashiwakura

2011-01-01

456

Rapid in situ detection of alkaloids in plant tissue under ambient conditions using desorption electrospray ionization.  

PubMed

Desorption electrospray ionization (DESI) mass spectrometry is applied to the in situ detection of alkaloids in the tissue of poison hemlock (Conium maculatum), jimsonweed (Datura stramonium) and deadly nightshade (Atropa belladonna). The experiment is carried out by electrospraying micro-droplets of solvent onto native or freshly-cut plant tissue surfaces. No sample preparation is required and the mass spectra are recorded under ambient conditions, in times of a few seconds. The impact of the sprayed droplets on the surface produces gaseous ions from organic compounds originally present in the plant tissue. The effects of operating parameters, including the electrospray high voltage, heated capillary temperature, the solvent infusion rate and the carrier gas pressure on analytical performance are evaluated and optimized. Different types of plant material are analyzed including seeds, stems, leaves, roots and flowers. All the previously reported alkaloids have been detected in C. maculatum, while fifteen out of nineteen known alkaloids for D. stramonium and the principal alkaloids of A. belladonna were also identified. All identifications were confirmed by tandem mass spectrometry. Results obtained show similar mass spectra, number of alkaloids, and signal intensities to those obtained when extraction and separation processes are performed prior to mass spectrometric analysis. Evidence is provided that DESI ionization occurs by both a gas-phase ionization process and by a droplet pick-up mechanism. Quantitative precision of DESI is compared with conventional electrospray ionization mass spectrometry (after sample workup) and the RSD values for the same set of 25 dicotyledonous C. maculatum seeds (one half of each seed analyzed by ESI and the other by DESI) are 9.8% and 5.2%, respectively. PMID:16284661

Talaty, Nari; Takáts, Zoltán; Cooks, R Graham

2005-12-01

457

Folate-vinca alkaloid conjugates for cancer therapy: a structure-activity relationship.  

PubMed

Vintafolide is a potent folate-targeted vinca alkaloid small molecule drug conjugate (SMDC) that has shown promising results in multiple clinical oncology studies. Structurally, vintafolide consists of 4 essential modules: (1) folic acid, (2) a hydrophilic peptide spacer, (3) a disulfide-containing, self-immolative linker, and (4) the cytotoxic drug, desacetylvinblastine hydrazide (DAVLBH). Here, we report a structure-activity study evaluating the biological impact of (i) substituting DAVLBH within the vintafolide molecule with other vinca alkaloid analogues such as vincristine, vindesine, vinflunine, or vinorelbine; (ii) substituting the naturally (S)-configured Asp-Arg-Asp-Asp-Cys peptide with alternative hydrophilic spacers of varied composition; and (iii) varying the composition of the linker module. A series of vinca alkaloid-containing SMDCs were synthesized and purified by HPLC and LCMS. The SMDCs were screened in vitro against folate receptor (FR)-positive cells, and anti-tumor activity was tested against well-established subcutaneous FR-positive tumor xenografts. The cytotoxic and anti-tumor activity was directly compared to that produced by vintafolide. Among all the folate vinca alkaloid SMDCs tested, DAVLBH-containing SMDCs were active, while those constructed with vincristine, vindesine, or vinorelbine analogues failed to produce meaningful biological activity. Within the DAVLBH series, having a bioreleasable, self-immolative linker system was found to be critical for activity since multiple analogues constructed with thioether-based linkers all failed to produce meaningful activity both in vitro and in vivo. Substitutions of some or all of the natural amino acids within vintafolide's hydrophilic spacer module did not significantly change the in vitro or in vivo potency of the SMDCs. Vintafolide remains one of the most potent folate-vinca alkaloid SMDCs produced to date, and continued clinical development is warranted. PMID:24564229

Leamon, Christopher P; Vlahov, Iontcho R; Reddy, Joseph A; Vetzel, Marilynn; Santhapuram, Hari Krishna R; You, Fei; Bloomfield, Alicia; Dorton, Ryan; Nelson, Melissa; Kleindl, Paul; Vaughn, Jeremy F; Westrick, Elaine

2014-03-19

458

Identification of legal highs--ergot alkaloid patterns in two Argyreia nervosa products.  

PubMed

Nowadays psychoactive plants marketed as "legal highs" or "herbal highs" increase in popularity. One popular "legal high" are the seeds of the Hawaiian baby woodrose Argyreia nervosa (Synonym: Argyreia speciosa, Convolvolus speciosus). At present there exists no study on A. nervosa seeds or products, which are used by consumers. The quality of commercial available A. nervosa seeds or products is completely unknown. In the present study, a commercial available seed collection (five seeds labeled "flash of inspiration", FOI) was analyzed for ergot alkaloids together with an A. nervosa product (two preparations in capsule form, "druids fantasy", DF). For this purpose high performance liquid chromatography high resolution tandem mass spectrometry (HPLC-HRMS/MS) technique was employed. Besides the major ingredients such as lysergic acid amide (LSA) and ergometrine the well known A. nervosa compounds lysergol/elymoclavine/setoclavine, chanoclavine and the respective stereoisomers were detected in DF, while only LSA and ergometrine could be found in FOI. In addition, in DF lysergic acid was found, which has not been reported yet as ingredient of A. nervosa. In both products, DF as well as in FOI, LSA/LSA-isomers were dominant with 83-84% followed by ergometrine/ergometrinine with 10-17%. Therefore, LSA, followed by ergometrine/ergometrinine, could be confirmed to be the main ergot alkaloids present in A. nervosa seeds/products whereas the other ergot alkaloids seemed to be of minor importance (less than 6.1% in DF). The total ergot alkaloid amounts varied considerably between DF and FOI by a factor of 8.6 as well as the LSA concentration ranging from 3 ?g (lowest amount in one FOI seed) to approximately 34 ?g (highest amount in one DF capsule). Among the FOI seeds, the LSA concentration varied from approximately 3-15 ?g per seed. Thus, the quality/potency of seeds/preparations depends on the amount of ergot alkaloids and the intensity of an expected trip is totally unpredictable. PMID:25036782

Paulke, Alexander; Kremer, Christian; Wunder, Cora; Wurglics, Mario; Schubert-Zsilavecz, Manfred; Toennes, Stefan W

2014-09-01

459

Inhibitory activities of the alkaloids from Coptidis Rhizoma against aldose reductase.  

PubMed

As part of our ongoing search of natural sources for therapeutic and preventive agents for diabetic complications, the rat lens aldose reductase (RLAR) inhibitory effect of Coptidis Rhizoma (the rhizome of Coptis chinensis Franch) was evaluated. Its extract and fractions exhibited broad and moderate RLAR inhibitory activities of 38.9 approximately 67.5 microg/mL. In an attempt to identify bioactive components, six quaternary protoberberine-type alkaloids (berberine, palmatine, jateorrhizine, epiberberine, coptisine, and groenlandicine) and one quaternary aporphine-type alkaloid (magnoflorine) were isolated from the most active n-BuOH fraction, and the chemical structures therein were elucidated on the basis of spectroscopic evidence and comparison with published data. The anti-diabetic complications capacities of seven C. chinensis-derived alkaloids were evaluated via RLAR and human recombinant AR (HRAR) inhibitory assays. Although berberine and palmatine were previously reported as prime contributors to AR inhibition, these two major components exhibited no AR inhibitory effects at a higher concentration of 50 microg/ml in the present study. Conversely, epiberberine, coptisine, and groenlandicine exhibited moderate inhibitory effects with IC(50) values of 100.1, 118.4, 140.1 microM for RLAR and 168.1, 187.3, 154.2 microM for HRAR. The results clearly indicated that the presence of the dioxymethylene group in the D ring and the oxidized form of the dioxymethylene group in the A ring were partly responsible for the AR inhibitory activities of protoberberine-type alkaloids. Therefore, Coptidis Rhizoma, and the alkaloids contained therein, would clearly have beneficial uses in the development of therapeutic and preventive agents for diabetic complications and diabetes mellitus. PMID:19023536

Jung, Hyun Ah; Yoon, Na Young; Bae, Hyun Ju; Min, Byung-Sun; Choi, Jae Sue

2008-11-01

460

Establishment of a search library about benzylisoquinoline alkaloids based on selective separation on the binaphthyl column and standard analysis on C18 column.  

PubMed

A search library about benzylisoquinoline alkaloids was established based on preparation of alkaloid fractions from Rhizoma coptidis, Cortex phellodendri, and Rhizoma corydalis. In this work, two alkaloid fractions from each herbal medicine were first prepared based on selective separation on the "click" binaphthyl column. And then these alkaloid fractions were analyzed on C18 column by liquid chromatography coupled with tandem mass spectrometry. Many structure-related compounds were included in these alkaloids fractions, which led to easy separation and good MS response in further work. Therefore, a search library of 52 benzylisoquinoline alkaloids was established, which included eight aporphine, 19 tetrahydroprotoberberine, two protopine, two benzyltetrahydroisoquinoline, and 21 protoberberine alkaloids. The information of the search library contained compound names, structures, retention times, accurate masses, fragmentation pathways of benzylisoquionline alkaloids, and their sources from three herbal medicines. Using such a library, the alkaloids, especially those trace and unknown components in some herbal medicine could be accurately and quickly identified. In addition, the distribution of benzylisoquinoline alkaloids in the herbal medicines could be also summarized by searching the source samples in the library. PMID:23109405