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Norditerpenoid alkaloids from the roots of Aconitum heterophyllum Wall with antibacterial activity.  


Two new aconitine-type norditerpenoid alkaloids 6-dehydroacetylsepaconitine (1) and 13-hydroxylappaconitine (2), along with three known norditerpenoid alkaloids lycoctonine, delphatine and lappaconitine were isolated from the roots of the Aconitum heterophyllum Wall. These compounds exhibited significant antibacterial activity. The structure of compound 1 and 2 were deduced on the basis of their spectral data. PMID:18608773

Ahmad, Manzoor; Ahmad, Waqar; Ahmad, Mansoor; Zeeshan, Muhammad; Obaidullah; Shaheen, Farzana



Highly Conjugated Norditerpenoid and Pyrroloquinoline Alkaloids with Potent PTP1B Inhibitory Activity from Nigella glandulifera.  


Three norditerpenoid alkaloids, nigelladines A-C (1-3), and one pyrroloquinoline alkaloid, nigellaquinomine (4), all possessing new skeletons with highly conjugated systems, were isolated from Nigella glandulifera. The 8aS-configuration for 1 and 2 was determined by comparison of the experimental and calculated electronic circular dichroism spectra. These alkaloids exhibited potent protein tyrosine phosphatase 1B (PTP1B) inhibitory activity but are devoid of cytotoxicity against the A431 cell line at 100 ?M. PMID:24593120

Chen, Qi-Bin; Xin, Xue-Lei; Yang, Yi; Lee, Shoei-Sheng; Aisa, H A



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

Microsoft Academic Search

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

K. S. Khetwal; Sunita Pande



Norditerpenoids and diterpenoids from Salvia multicaulis with antituberculous activity.  


From the roots of Salvia multicaulis, four new aromatic norditerpenoids, multicaulin (1), 12-demethylmulticauline (2), multiorthoquinone (3), and 12-demetylmultiorthoquinone (4), two new abietane diterpenoids, 12-methyl-5-dethydrohorminone (5) and 12-methyl-5-dehydroacetylhorminone (6), as well as a new pimarane diterpenoid, salvipimarone (7), were isolated. Also obtained in this investigation were the known compounds alpha-amyrin, hinokione, horminone, lupeol, manool, 1-oxoferruginol, 18-oxoferruginol, pisiferal, and sempervirol. The structures of compounds 1-7 were established by 1D and 2D NMR techniques and by chemical methods. The antituberculous activity of 1-7 was tested against Mycobacterium tuberculosis strain H37Rv, and all compounds were found to be significantly active, with 2 and 4-6 being the most potent substances. Six of these novel compounds were evaluated against a number of additional bacterial cultures. PMID:9428161

Ulubelen, A; Topcu, G; Johansson, C B



Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima.  


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

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



Transformations of manool. tri- and tetracyclic norditerpenoids with in vitro activity against Plasmodium falciparum.  


The known 17-norisopimar-15-ene-8beta,13beta-diol (5) and five new semisynthetic norditerpenoids, ethyl 17-norabiet-13(15)-E-en-8beta-ol-16-oate (6), ethyl 17-norabiet-13(15)-Z-en-8beta-ol-16-oate (7), 17-norpimaran-13alpha-ethoxy-8,16-olactone (8), 17-norisopimarane-8beta,15-diol (9), and 17-norarabiet-13(15)-ene-8beta,16-diol (10), were prepared from manool (11). Standard spectroscopic data including X-ray crystal analysis were used to determine the structures of 5-10. All five compounds exhibited in vitro antiplasmodial activity against the malarial parasite Plasmodium falciparum at varying microg mL(-1) concentrations. PMID:17625894

van Wyk, Albert W W; Lobb, Kevin A; Caira, Mino R; Hoppe, Heinrich C; Davies-Coleman, Michael T



Isoquinoline alkaloids  

Microsoft Academic Search

Representatives of eleven different classes of isoquinoline alkaloids inhibit Na+, K+-ATPase and Mg2+-ATPase in rat brain microsomal preparations. In most cases the Na+, K+-ATPase is more sensitive than Mg2+-ATPase to inhibition by the alkaloids. The classes of alkaloids can be ranked according to potency of inhibition of Na+, K+-ATPase. Protoberberines are most effective, followed in decreasing order by benzophenanthridines, benzylisoquinolines,

Laurence R. Meyerson; Kenneth D. McMurtrey; Virginia E. Davis



Alkaloids in Marine Algae  

PubMed Central

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

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



Aromatic alkaloids from ascidians  

Microsoft Academic Search

More than 200 aromatic alkaloids isolated from marine tunicates are grouped into structural types and discussed in terms of their reported pharmacological activity. The major groups of alkaloids which are discussed in detail include the benzopentathiepins and trithianes, lamellarins and related structures, ecteinascidins, ?-carboline alkaloids, and the pyridoacridines. References to reported syntheses are also included. Effects of substituent changes within

Bruce F. Bowden



Alkaloids from Sarcomelicope megistophylla.  


Two new alkaloids were isolated from the bark of Sarcomelicope megistophylla. Cyclomegistine B (1), a new quinolone alkaloid, that possesses a rare cyclobuta[b]quinoline ring system and sarcomejine B (2) which is a quinolone alkaloid with an unusual side chain. The structure of both compounds was elucidated on the basis of MS data and extensive NMR studies. PMID:17207940

Mitaku, Sofia; Fokialakis, Nikolas; Magiatis, Prokopios; Tillequin, François



Alkaloids from Papaver coreanum.  


The alkaloid pattern of the endemic plant Papaver coreanum Nakai (Papaveraceae) was determined for the first time. Eight alkaloids could be identified by LC/ESI-MS/MS and high-resolution mass spectrometry. Among them, protopine and allocryptopine represent the main components. Besides norsanguinarine, sanguinarine, dihydrosanguinarine, oxysanguinarine, lincangenine, and cryptopine, some other trace alkaloids were found whose structures remain unknown. PMID:22224268

Lee, Dong-Ung; Park, Jong Hee; Wessjohann, Ludger; Schmidt, Jürgen



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



Alkaloids of Datura ceratocaula.  


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

Berkov, Strahil



Polyamines and plant alkaloids.  


Naturally occurring alkaloids are nitrogenous compounds that constitute the pharmacogenically active basic principles of flowering plants. Alkaloids are classified into several biogenically related groups. Tobacco alkaloids are metabolised from polyamines and diamines putrescine and cadaverine. N-methyl transferase is the first enzyme in alkaloid biosynthetic pathway which drives the flow of nitrogen away from polyamine biosynthesis to alkaloid biosynthesis. Arginine decarboxylase has been suggested to be primarily responsible for providing putrescine for nicotine synthesis. Tryptophan is the precursor of indole alkaloids. However, the biosynthetic pathway of tropane and isoquinoline alkaloids are not clear. Genes for several key biosynthetic enzymes like arginine decarboxylase, ornithine decarboxylase, putrescine N-methyl transferase and spermidine synthase, hyoscyamine 6 beta hydroxylase,tryptophan decarboxylase etc have been cloned from different plant species. These genes are regulated by plant hormones, light, different kinds of stress and elicitors like jasmonates and their strong expression is primarily in the cultured roots. In view of this, the axenic hairy root cultures induced by Agrobacterium rhizogenes have been utilised to synthesise secondary metabolites. The current development in the knowledge of alkaloid biosynthesis, particularly molecular analysis, has been discussed in this review that may help to open up new avenues of investigation for the researchers. PMID:11395950

Ghosh, B



[Alkaloids of Annonaceae. XXIX. Alkaloids of Annona muricata].  


From leaves, root - and stem - barks of Annona muricata L., seven isoquinoline alkaloids have been isolated: reticuline (main alkaloid), coclaurine, coreximine, atherosperminine, stepharine. Anomurine and anomuricine, two minor alkaloids, are new tetrahydrobenzylisoquinolines, with 5, 6, 7 substituted ring A. The phytochemical significance of these alkaloids is discussed. PMID:17401878

Leboeuf, M; Legueut, C; Cavé, A; Desconclois, J F; Forgacs, P; Jacquemin, H



Alkaloids from Lindera aggregata.  


Eight alkaloids, including a new compound, (+)-norboldine acetate (1), and seven known ones, (+)-norboldine (2), (+)-boldine (3), (+)-laurotetanine (4), (+)-N-methyllaurotetanine (5), (+)-reticuline (6), (-)-pronuciferine (7), and pallidine (8) were isolated from the roots of Lindera aggregata. The structures of these alkaloids were determined by spectroscopic and chemical methods, especially 2D NMR techniques, which also allowed the first full NMR assignments of alkaloids 2, 4 and 5. Among them, the 1D NMR chemical shifts of (+)-norboldine (2) showed a remarkable environmental sensitive behavior. All the alkaloids were tested in cytotoxicity assays against L1210 and K562 tumor cell lines; only (+)-norboldine (2) showed weak activity against the L1210 cell line. PMID:19370873

Gan, Li-She; Yao, Wei; Mo, Jian-Xia; Zhou, Chang-Xin



Alkaloids from Sternbergia colchiciflora.  


Twenty-one alkaloids and related compounds were found in Sternbergia colchiciflora (Amaryllidaceae), a hitherto not studied plant species. Twenty of them were detected by GC-MS in the crude extracts of this plant species. Ten alkaloids were isolated and their structures confirmed by NMR, MS and CD measurements. Many of the compounds found in this species, such as lycorine, tazettine, haemanthidine, are known to possess strong bioactivity. Variations in the alkaloid pattern were found during the phenological cycle of the plant. Lycorine-type compounds were dominant in the plant organs during both the flowering period and dormancy. The alkaloid pattern during both periods of leaf development and fructification was dominated by haemanthamine-type in the leaves and lycorine-type compounds in the bulbs, respectively. PMID:19678530

Berkov, Strahil; Bastida, Jaume; Tsvetkova, Reneta; Viladomat, Francesc; Codina, Carles



Occurrence of halogenated alkaloids.  


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



Alkaloids of Papaver fugax  

Microsoft Academic Search

Papaver fugax growing on the shore of Lake Kazenoi Am in the Checheno-Ingushskii ASSR at the boundary with the Dagestan ASSR has yielded\\u000a 0.39% of alkaloids. Seven alkaloids have been isolated, of which cheilanthifoline, scoulerine, and reticuline have been detected\\u000a in this species for the first time, while it is the first time that d-remeroline has been found in a

V. A. Chelombut'ko; I. A. Israilov



Cyclopeptide alkaloids from Zizyphus jujuba  

Microsoft Academic Search

A new cyclopeptide alkaloid, jubanine-C (1), together with known alkaloids scutianine-C (4) and zizyphine-A (5), have been isolated from the stem bark of Zizyphus jujuba and identified by spectral analysis.

M. Tripathi; M. B. Pandey; R. N. Jha; V. B. Pandey; P. N. Tripathi; J. P. Singh



Alkaloids from Balanites aegyptiaca.  


High performance liquid chromatographic (HPLC) analysis of a dichloromethane extract of the stem-barks of Balanites aegyptiaca has yielded two known alkaloids, N-trans-feruloyltyramine (1) and N-cis-feruloyltyramine (2), and three common metabolites, vanillic acid, syringic acid and 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone. PMID:10844174

Sarker, S D; Bartholomew, B; Nash, R J



Alkaloids from Balanites aegyptiaca  

Microsoft Academic Search

High performance liquid chromatographic (HPLC) analysis of a dichloromethane extract of the stem-barks of Balanites aegyptiaca has yielded two known alkaloids, N-trans-feruloyltyramine (1) and N-cis-feruloyltyramine (2), and three common metabolites, vanillic acid, syringic acid and 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone.

S. D Sarker; B Bartholomew; R. J Nash



Alkaloids from Alstonia scholaris  

Microsoft Academic Search

Three new indole alkaloids, nareline ethyl ether, 5-epi-nareline ethyl ether and scholarine-N(4)-oxide, in addition to nareline methyl ether, picrinine and scholaricine were isolated from the leaf extract of Alstonia scholaris. © 1997 Elsevier Science Ltd. All rights reserved

Kam Toh-Seok; Nyeoh Kok-Tih; Sim Kooi-Mow; K. Yoganathan



The Vinca Alkaloids  

Microsoft Academic Search

\\u000a The periwinkle plant, Cantharanthus roseus G. Don (Vinca rosea Linn.) is endemic to the island of Madagascar, and has long been ascribed a wide assortment of medicinal properties ranging\\u000a from the treatment of diabetes to wound healing. Of the over fifty alkaloids present in minute quantities within the plant,\\u000a only two (vincristine and vinblastine) have been isolated, synthesized, and are

Nicole Coufal; Lauge Farnaes


Quinolizidine alkaloids from Lupinus lanatus  

NASA Astrophysics Data System (ADS)

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

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



Automatic alkaloid removal system.  


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

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



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.

Schiff, Paul L.



Antimicrobially active alkaloids from Tabernaemontana chippii.  


From Tabernaemontana chippii root bark, forty-five alkaloids were isolated; thirty-four were fully characterized by means of their spectral data and/or co-tlc; eight alkaloids were new, four of them being 3-hydroxy derivatives of known dimeric voacamine type alkaloids. Most of the twenty-six known alkaloids belonged to the corynanthean, ibogan, or bisindole classes. The structures of eleven other alkaloids--all minor--were only partially elucidated, most of them being new alkaloids. All the dimeric alkaloids were shown to possess strong antimicrobial activity against gram-positive bacteria and moderate to weak activity against gram-negative bacteria. PMID:4031898

Van Beek, T A; Verpoorte, R; Svendsen, A B; Fokkens, R



Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid.  


The alkaloid composition of the giant cactus, Carnegiea gigantea Br. & R., was studied. Chromatographic separation led to the isolation of four tetrahydroisoquinoline alkaloids: carnegine, salsolidine, gigantine and arizonine. The structure of the new natural product, arizonine, was establihsed by spectroscopic data and total synthesis via two independent routes. Salsolidine is reported for the first time in the cacti. Also new to this species are 3-methoxytyramine and 3,4-dimethoxypenethylamine, which were identified in the alkaloid extract by gas chromatography-mass spectrometry. Dopamine was isolated from fresh plant material. PMID:957908

Bruhn, J G; Lundström, J



Cyclopeptide Alkaloids from Ziziphus apetala.  


Six novel Ia?-type cyclopeptide alkaloids (1-6) were isolated from stems of Ziziphus apetala. Compound 5 and the known compounds mauritine A (7) and mauritine F (8) were isolated from the roots. Their structures were determined by spectroscopic analyses and chemical methods. The total alkaloids from the roots and the isolated cyclopeptide alkaloids were tested for antidepressant behavior on mice, cytotoxicity, and 11?-hydroxysteroid dehydrogenase (11?-HSD) inhibition in vitro. Only mauritine A (7) showed inhibitory activity on 11?-HSD1, with IC?? values of 52.0 (human) and 31.2 ?g/mL (mouse). PMID:22148241

Han, Jing; Ji, Chang-Jiu; He, Wen-Jun; Shen, Yu; Leng, Ying; Xu, Wen-Yan; Fan, Jun-Ting; Zeng, Guang-Zhi; Kong, Ling-Dong; Tan, Ning-Hua



Tropane alkaloids from Latua pubiflora.  


Four known tropane alkaloids were isolated from the leaves of the endemic Chilean plant Latua pubiflora (Solanaceae). For the first time; 3alpha-cinnamoyloxitropane and apoatropine are reported in this plant. Scopolamine and hyoscyamine were previously reported. PMID:14577619

Muńoz, Orlando; Casale, John F



Cyclopeptide alkaloids of Scutia buxifolia  

Microsoft Academic Search

Two new peptide alkaloids, scutianines-K and -L were isolated from Scutia buxifolia, a plant growing in Brazil, Argentina and Uruguay. Their structures have been determined on the basis of spectroscopic studies. The stereochemistry of the N,N-dimethyl amino acid side-chain and the ring amino acid residues in both alkaloids have been assigned by gas chromatography employing modified cyclodextrins as chiral stationary

Ademir F. Morel; Emilia C. S. Machado; Jane J. Moreira; Antonio S. Menezes; Marco A. Mostardeiro; Nilo Zanatta; Ludger A. Wessjohann



Benzylisoquinoline alkaloids from gnetum parvifolium  


The investigation of the chemical constituents from the lianas of Gnetum parvifolium resulted in the isolation of three new benzylisoquinoline alkaloids, (+/-)-N-methylhigenamine (1), (-)-N-methylhigenamine N-oxide (2), and (+/-)-8-(p-hydroxybenzyl)-2, 3,10,11-tetrahydroxyprotoberberine (3), together with two known alkaloids, higenamine and trigonelline. The structures of 1-3 were determined by chemical methods and spectral analysis including 2D NMR and NOE studies. PMID:10425133

Xu; Lin



Analysis of tropane and related alkaloids.  


The current methods for tropane alkaloid chromatographic separation and determination are summarised. The alkaloids included are: the medicinally applied tropic acid esters hyoscyamine and scopolamine and their derivatives, cocaine and derivatives, the metabolites and degradation products of these compounds occurring in plant material, calystegines as nortropane alkaloids, anatoxins as homonortropane alkaloids, pelletierines and pseudopelletierines as alkaloids with isomeric structures. Developments in GC, HPLC, CE and TLC are presented and the advantages of each method for plant analysis are discussed. A summary for each chromatographic method lists the instrumentation and parameters applied for tropane alkaloids. PMID:12458942

Dräger, Birgit



Three new cyclopeptide alkaloids from Zizyphus species  

Microsoft Academic Search

Two new cyclopeptide alkaloids, xylopyrine-D and xylopyrine-E, from Zizyphus xylopyra and a new alkaloid, jubanine-E, from Zizyphus jujuba have been isolated and their structures were established by chemical and spectral evidences.

Manoj B. Pandey; Ashok K. Singh; Jagdish P. Singh; Virendra P. Singh; Vidya B. Pandey



I. Cyclopeptide Alkaloids; II. Phycocyanobilipeptides.  

National Technical Information Service (NTIS)

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 pat...

J. C. Lagarias



Curare Alkaloids from Chondodendron Tomentosum  

Microsoft Academic Search

Crystalline d-tubocurarine has been isolated in good yield from curare prepared from a single plant species, namely, Chondodendron tomentosum. This result establishes with certainty the botanical origin of this compound and substantiates the supposition that it is this species which furnishes the active constituent in certain types of curare. The extract from this plant furthermore yielded two new tertiary alkaloids

O. Wintersteiner; J. D. Dutcher



Alkaloids from Boophone haemanthoides (Amaryllidaceae).  


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

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



Study on the Alkaloids of Melodinus tenuicaudatus.  


Fourteen alkaloids were isolated from the stem bark of MELODINUS TENUICAUDATUS Tsiang et P. T. Li. Eleven of them were identified as known alkaloids, namely, scandine ( 2), Delta (14)-eburnamine ( 4), vindolinine N(b)-oxide ( 5), 11-methoxytabersonine ( 6), vindolinine ( 7), EPI-vindolinine N(b)-oxide ( 8), hazuntine ( 9), compactinervine ( 10), 11-hydroxytabersonine ( 11), Delta (14)-vincine ( 12), and normacusine B ( 14). Two alkaloids were new: 10-hydroxyscandine ( 1), and the dimer, tenuicausine ( 3); their structures were elucidated by spectroscopic and chemical methods. One alkaloid ( 13) occurring in trace amounts, could not be identified. PMID:17265274

Zhou, Y L; Ye, J H; Li, Z M; Huang, Z H



27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2010 CFR

...increase the temperature to 110° and dry to a constant weight before taking melting point. Note. Brucine alkaloid tetrahydrate melts at 105 °C. while the anhydrous form melts at 178 °C. (c) Strychnine test. Brucine alkaloid shall be...



Phenylalkylamine alkaloids from Stapelia hirsuta L.  


Four alkaloids of the phenethylamine derivatives have been isolated from the n-butanol fraction of the aerial parts of Stapelia hirsuta L. The structures of the isolated alkaloids were determined as N-acetyl hordenine (a new natural compound), hordenine, candicine and hordenine-1-O-beta-D-glucoside, in addition to luteolin-7-O-beta-D-glucopyranoside. PMID:16753902

Shabana, Marwan; Gonaid, Mariam; Salama, Maha Mahmoud; Abdel-Sattar, Essam



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.



Megistolactone, a new alkaloid from Sarcomelicope megistophylla.  


A new quinolone alkaloid, megistolactone (1) was isolated from the bark of Sarcomelicope megistophylla. Its structure has been elucidated on the basis of MS and NMR data. From a biogenetic point of view, this compound should be considered as an oxidation product of 1,2,3,4-tetra-O-subsituted acridone alkaloids, which are also present in the bark. PMID:11204188

Fokialakis, N; Magiatis, P; Skaltsounis, A L; Tillequin, F; Sévenet, T



A new indole alkaloid from Alstonia scholaris.  


A new indole alkaloid, N-formylscholarine, together with picrinine, strictamine and nareline has been isolated from the fruit pods of Alstonia scholaris, and their structures were established by various spectral data. This is the first report of these alkaloids in A. scholaris fruit pods. PMID:19851925

Jain, Luna; Pandey, M B; Singh, Sarita; Singh, A K; Pandey, V B



A new indole alkaloid from Alstonia scholaris  

Microsoft Academic Search

A new indole alkaloid, N-formylscholarine, together with picrinine, strictamine and nareline has been isolated from the fruit pods of Alstonia scholaris, and their structures were established by various spectral data. This is the first report of these alkaloids in A. scholaris fruit pods.

Luna Jain; M. B. Pandey; Sarita Singh; A. K. Singh; V. B. Pandey



Halogenated Indole Alkaloids from Marine Invertebrates  

PubMed Central

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

Pauletti, Patricia Mendonca; Cintra, Lucas Silva; Braguine, Caio Guedes; da Silva Filho, Ademar Alves; Silva, Marcio Luis Andrade e; Cunha, Wilson Roberto; Januario, Ana Helena



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.

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



Piperidine alkaloids: human and food animal teratogens.  


Piperidine alkaloids are acutely toxic to adult livestock species and produce musculoskeletal deformities in neonatal animals. These teratogenic effects include multiple congenital contracture (MCC) deformities and cleft palate in cattle, pigs, sheep, and goats. Poisonous plants containing teratogenic piperidine alkaloids include poison hemlock (Conium maculatum), lupine (Lupinus spp.), and tobacco (Nicotiana tabacum) [including wild tree tobacco (Nicotiana glauca)]. There is abundant epidemiological evidence in humans that link maternal tobacco use with a high incidence of oral clefting in newborns; this association may be partly attributable to the presence of piperidine alkaloids in tobacco products. In this review, we summarize the evidence for piperidine alkaloids that act as teratogens in livestock, piperidine alkaloid structure-activity relationships and their potential implications for human health. PMID:22449544

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



Angustinine--a new benzopyridoquinolizine alkaloid from Alangium lamarckii.  


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



Three new pyridoacridine type alkaloids from a singaporean ascidian.  


Two new pyridoacridine alkaloids, kuanoniamines E and F, and a new ring-opened pyridoacridine alkaloid, subarine, were isolated from a Singaporean ascidian. Also isolated were known pyridoacridine alkaloids ascididemin and kuanoniamines A and D. The structures of the alkaloids were determined by spectroscopic methods. PMID:12193032

Nilar, Nilar; Sidebottom, Philip J; Carté, Brad K; Butler, Mark S



Variabines A and B: new ?-carboline alkaloids from the marine sponge Luffariella variabilis.  


Two new ?-carboline alkaloids, variabines A (1) and B (2), were isolated from the Indonesian marine sponge Luffariella variabilis. Their structures were elucidated from spectral data, and 1 was found to be a sulfonated derivative of 2. Although numerous ?-carboline alkaloids have been isolated from natural sources to date, 1 is the first ?-carboline derivative containing a sulfate group. Compound 2 inhibited chymotrypsin-like activity of the proteasome and Ubc13 (E2)-Uev1A interaction with IC50 values of 4 and 5 ?g/mL, respectively, whereas 1 had little effect on the activity or interaction. PMID:23686294

Sakai, Eriko; Kato, Hikaru; Rotinsulu, Henki; Losung, Fitje; Mangindaan, Remy E P; de Voogd, Nicole J; Yokosawa, Hideyoshi; Tsukamoto, Sachiko



4-Quinolone alkaloids from Melochia odorata.  


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

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



Antiprotozoal sesquiterpene pyridine alkaloids from Maytenus ilicifolia.  


As part of a bioprospecting program aimed at the discovery of antiprotozoal agents from the Brazilian flora, two new sesquiterpene pyridine alkaloids, ilicifoliunines A (1) and B (2), along with the known alkaloids aquifoliunine E-I (3) and mayteine (4), were isolated from the root bark of Maytenus ilicifolia. The structures of 1 and 2 were established on the basis of spectroscopic data interpretation. Alkaloid 3 displayed potent in vitro antiprotozoal activity against Leishmania chagasi and Trypanosoma cruzi, with IC(50) values of 1.4 and 41.9 ?M, respectively, as well as low cytotoxicity against murine peritoneal macrophages (IC(50) of 1.8 mM). PMID:22559947

Santos, Vânia A F F M; Regasini, Luis O; Nogueira, Cláudio R; Passerini, Gabriela D; Martinez, Isabel; Bolzani, Vanderlan S; Graminha, Márcia A S; Cicarelli, Regina M B; Furlan, Maysa



Bioactive acridone alkaloids from Swinglea glutinosa.  


A new prenylated acridone alkaloid, 1,3,5-trihydroxy-2,8-bis(3-methylbut-2-enyl)-10-methyl-9-acridone (1), was isolated from the stembark of Swinglea glutinosa, along with three known acridone alkaloids, 5-hydroxynoracronycine (2), 1,3,5-trihydroxy-4-methoxy-2-(3-methylbut-2-enyl)-10-methyl-9-acridone (3), and 1,3,5-trihydroxy-4-methoxy-10-methylacridone (4). The isolated alkaloids were assessed in vitro against chloroquine-sensitive and -resistant Plasmodium falciparum strains and for cytotoxicity using HeLa cells. PMID:11575960

Weniger, B; Um, B H; Valentin, A; Estrada, A; Lobstein, A; Anton, R; Maillé, M; Sauvain, M



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


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

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



Alkaloids from Portulaca oleracea L.  


Five alkaloids (oleraceins A, B, C, D and E) were isolated from Portulaca oleracea L., and their structures determined by spectroscopic methods as 5-hydroxy-1-p-coumaric acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-ferulic acyl-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-(p-coumaric acyl-7'-O-beta-D-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside, 5-hydroxy-1-(ferulic acyl-7'-O-beta-D-glucopyranose)-2,3-dihydro-1H-indole-2-carboxylic acid-6-O-beta-D-glucopyranoside and 8,9-dihydroxy-1,5,6,10b-tetrahydro-2H-pyrrolo[2,1-a]isoquinolin-3-one, respectively. PMID:16203019

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



Cyclopeptide alkaloids from stems of Paliurus ramossisimus  

Microsoft Academic Search

Three 13-membered cyclopeptide alkaloids, paliurines G, H and I, together with six known alkaloids, nummularine H, daechuine-S3, paliurines A–C and F, were isolated from the stem of Paliurus ramossisimus by a combination of centrifugal partition chromatography and preparative TLC. Their structures were characterized and established on the basis of spectral analysis. A preliminary study indicated that nummularine H could shorten

Shoei-Sheng Lee; Whei-Chuan Su; Karin C. S. Chen Liu



Two Alangium alkaloids from Alangium lamarckii.  


Two new Alangium alkaloids, 1',2'-dehydrotubulosine (1) and alangine (2), were isolated from the dried fruits of Alangium lamarckii along with tubulosine (3), isotubulosine (4), deoxytubulosine, cephaeline, isocephaeline, psychotrine, neocephaeline, 10-O-demethylcephaeline, 2'-N-(1"-deoxy-1" -beta-D-fructopyranosyl)cephaeline, protoemetine, protoemetinol, salsoline, and alangiside. The structures of the new alkaloids (1 and 2) were determined by spectroscopic and chemical means. PMID:10843602

Itoh, A; Ikuta, Y; Tanahashi, T; Nagakura, N




Microsoft Academic Search

Epichloë species and their anamorphs, Neotyphodium species, are fungal endophytes that inhabit cool-season grasses and often produce bioprotective alkaloids. These alkaloids include lolines, which are insecticidal and insect feeding deterrents. Lolines are exo-1-aminopyrrolizidines with an oxygen bridge between carbons 2 and 7, and are usually methylated and formylated or acetylated on the 1-amine. In previously published studies lolines were shown

Jerome Ralph Faulkner



Lycopodium alkaloids: isolation and asymmetric synthesis.  


Lycopodium alkaloids have attracted the attention of many natural product chemists and synthetic organic chemists due to their important biological activities and unique skeletal characteristics. In this review we describe isolation and asymmetric syntheses of several new alkaloids such as lycoposerramines-C, -V, -W, and cernuine, and show that asymmetric total synthesis played a key role in elucidating the structures of these complex natural products. PMID:21452079

Kitajima, Mariko; Takayama, Hiromitsu



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


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



Multicomponent therapeutics of berberine alkaloids.  


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



Antimicrotubule properties of benzophenanthridine alkaloids.  


Chelidonine, sanguinarine, and chelerythrine are natural benzophenanthridine alkaloids that inhibit taxol-mediated polymerization of rat brain tubulin in the micromolar range. Chelidonine is a weak, competitive inhibitor of colchicine binding to tubulin but does not inhibit podophyllotoxin binding. On the other hand, sanguinarine inhibits both colchicine and podophyllotoxin binding to tubulin with I50 values of 32 and 46 microM, respectively, and chelerythrine inhibits with I50 values of 55 and 60 microM, respectively. The inhibition by these two agents is of the mixed type. Tubulin forms an acid-reversible pseudobase with the imminium ion of sanguinarine, probably through several of its sulfhydryl groups, as shown by the loss of the yellow color of sanguinarine and its 596-nm fluorescence emission peak. Chelidonine, on the other hand, cannot undergo such pseudobase formation, and we conclude that it acts by a different mechanism. A number of previously described pharmacologic effects of these agents may be due to their inhibition of microtubule function. PMID:7902132

Wolff, J; Knipling, L



Mauritine J, a cyclopeptide alkaloid from Zizyphus mauritiana  

Microsoft Academic Search

A new cyclopeptide alkaloid, mauritine J, besides known alkaloids, was isolated from the root bark of Zizyphus mauritiana. Its structure was established by homo- and hetero-nuclear 2D NMR analysis and compared with that of amphibine E.

Akino Jossang; Abdellatif Zahir; Dandio Diakite



Cyclopeptide alkaloids from the bark of Waltheria douradinha  

Microsoft Academic Search

Two peptide alkaloids, waltherine-A and waltherine-B were isolated from Waltheria douradinha, together with two known peptide alkaloids, adouetine-Y? and scutianine-B. Their structures were elucidated on the basis of spectroscopic analyses.

Ademir F Morel; Ilaine T. S Gehrke; Marco A Mostardeiro; Eduardo M Ethur; Nilo Zanatta; Emilia C. S Machado



Xylopyrine-C, a new cyclopeptide alkaloid from Zizyphus xylopyra  

Microsoft Academic Search

Xylopyrine-C, a new 14-membered ring cyclopeptide alkaloid, has been isolated from the root bark of Zizyphus xylopyra together with a known alkaloid scutianine-C, and their structures were established by chemical and spectral evidences.

Ashok K. Singh; Manoj B. Pandey; Virendra P. Singh; Vidya B. Pandey



An Acetylenic Alkaloid from the Calcareous Sponge Leucetta sp.  

PubMed Central

A new acetylenic alkaloid was isolated from the sponge Leucetta sp. The structure was established by analyzing spectroscopic data. The alkaloid showed cytotoxicity IC50 2.5 ?g/mL against NBT-T2 cells.

Hermawan, Idam; de Voogd, Nicole J.; Tanaka, Junichi



Benzylisoquinoline alkaloid biosynthesis in opium poppy.  


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



Hemlock alkaloids from Socrates to poison aloes.  


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



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

PubMed Central

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

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



Occurrence of pyrrolizidine alkaloids in three Ethiopian Solanecio species  

Microsoft Academic Search

Three Ethiopian Solanecio species, namely Solanecio angulatus (Vahl) C. Jeffrey, Solanecio mannii (Hook. f.) C. Jeffrey, and Solanecio tuberosus (Sch. Bip. ex A. Rich.) C. Jeffrey var. tuberosus were analysed by capillary gas chromatography–mass spectrometry (GLS–MS) for their pyrrolizidine alkaloid content. All the extracts investigated contain pyrrolizidine alkaloids. Whilst only traces of alkaloids could be detected in the leaf extract

Kaleab Asres; Frank Sporer; Michael Wink



Secondary and tertiary isoquinoline alkaloids from Xylopia parviflora.  


From the secondary and tertiary alkaloidal fractions of the root and the bark of Xylopia parviflora (Annonaceae), the isoquinoline alkaloids, 10,11-dihydroxy-1,2-dimethoxynoraporphine and parvinine were isolated, along with 39 known alkaloids. Their structures were determined on the basis of analysis of spectroscopic data. PMID:16963092

Nishiyama, Yumi; Moriyasu, Masataka; Ichimaru, Momoyo; Iwasa, Kinuko; Kato, Atsushi; Mathenge, Simon G; Chalo Mutiso, Patrick B; Juma, Francis D



Antimicrobially active isoquinoline alkaloids from Litsea cubeba.  


Bioassay-guided fractionation of the alkaloidal extract of the aerial part of Litsea cubeba led to the isolation of two new isoquinoline alkaloids, (+)- N-(methoxycarbonyl)-N-norboldine (1) and (+)-isoboldine beta-N-oxide (2), together with 11 known analogues (3-13). Their structures were established by extensive spectroscopic techniques and by comparing spectroscopic data with those in the literature. Compounds 1 and 4 showed antimicrobial activities. This is the first report on the presence of compounds 1, 2, 6, 8, 9, 11, and 12 in this plant and on the antimicrobial activities of 1 and 4. The bioactivities of isoquinoline alkaloids are also at least partly responsible for the pharmacological function of the folk medicinal plant Litsea cubeba. PMID:18991207

Feng, Tao; Xu, Yan; Cai, Xiang-Hai; Du, Zhi-Zhi; Luo, Xiao-Dong



An efficient synthesis of loline alkaloids  

NASA Astrophysics Data System (ADS)

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

Cakmak, Mesut; Mayer, Peter; Trauner, Dirk



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

Microsoft Academic Search

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

Nurgun Erdemoglu; Semiha Ozkan; Fatma Tosun




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



Antitussive indole alkaloids from Kopsia hainanensis.  


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

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



New quinoline alkaloids from Ruta chalepensis.  


The roots of Ruta chalepensis, collected from the northern Saudi desert, yielded two new quinoline alkaloids, namely, 2-ż6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexylż-hydroquinolin-4-one (1) and 2-ż6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexylż-4-methoxy-quinoline (2). Nine previously reported alkaloids, dictamnine, pteleine, skimmianine, rutacridone, isogravacridonechlorine, maculosidine, graveoline, graveolinine, and 4-methoxy-1-methyl-2(1H)-quinolinone, and coumarins, chalepensin, and umbelliferone were also isolated. Structure elucidations were based primarily on 1D and 2D NMR analyses and chemical transformations. Antimicrobial activity of these compounds is discussed. PMID:10924184

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



Insecticidal sesquiterpene pyridine alkaloids from Maytenus chiapensis.  


The new sesquiterpene pyridine alkaloids chiapenines ES-I (1), ES-II (2), ES-III (3), and ES-IV (4), in addition to the known alkaloids wilfordine (5), alatamine (6), wilforidine (7), alatusinine (8), euonine (9), euonymine (10), ebenifoline E-I (11), forrestine (12), mayteine (13), and 4-hydroxy-7-epi-chuchuhuanine E-V (14), were isolated from the leaves of Maytenus chiapensis. Their structures were elucidated by 1D and 2D NMR spectroscopy, including homonuclear and heteronuclear correlation (COSY, ROESY, HSQC, and HMBC) experiments. Wilfordine, alatusinine, and euonine exhibited strong antifeedant activity against Spodoptera littoralis. PMID:14738378

Núńez, Marvin J; Guadańo, Ana; Jiménez, Ignacio A; Ravelo, Angel G; González-Coloma, Azucena; Bazzocchi, Isabel L



Evaporative light scattering detection of pyrrolizidine alkaloids.  


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



Tropane alkaloids of Datura innoxia from Morocco.  


Fifty three alkaloids were identified in the organs (roots, stems, leaves, flowers, and seeds) of Datura innoxia by GC/MS. Seventeen of them are reported for the first time for this species and one nor-derivative, 3-phenylacetoxynortropane (28), for the genus Datura. Furthermore, four new tropane esters were tentatively identified as 3-acetoxy-6,7-epoxytropane (acetylscopine) (10), 3-acetoxy-6-propionyloxy-7-hydroxytropane (15), 6,7-dehydro-3-phenylacetoxytropane (25), and 3-(2'-phenylpropionyloxy)-6,7-epoxynortropane (dihydroaponorscopolamine) (37) on the basis of their mass spectral data. Hyoscyamine (44) and scopolamine (48) figure as main alkaloids in the roots and aerial parts, respectively. PMID:22486036

El Bazaoui, Ahmed; Bellimam, My Ahmed; Soulaymani, Abdelmajid



Quaternary isoquinoline alkaloids from Xylopia parviflora.  


From the quaternary alkaloidal fraction of the bark and the root of Xylopia parviflora (Annonaceae), four isoquinoline alkaloids, xylopinidine, dehydrocoreximine, N, N-dimethylanomurine and N-methylphoebine were isolated along with the known compounds, pycnarrhine, lotusine, 6,7-dimethoxy-2-methyl-isoquinolinium salt, 1,2-dehydroreticuline, (-)-phellodendrine, (+)-tembetarine, (-)-litcubine, (+)-magnoflorine, tetradehydroreticuline, (-)-oblongine, (+)-menisperine, (+)-N-methylcorydine, stepharanine, (+)-xanthoplanine, dehydrodiscretine, jatrorrhizine and palmatine. 3,4-Dihydro-6,7-dimethoxy-2-methyl-isoquinolinium and N-methylpurpuerine were isolated as natural products for the first time. Their structures were determined on the basis of spectroscopic evidence. PMID:15081299

Nishiyama, Yumi; Moriyasu, Masataka; Ichimaru, Momoyo; Iwasa, Kinuko; Kato, Atsushi; Mathenge, Simon G; Chalo Mutiso, Patrick B; Juma, Francis D



Antimicrobial properties of alkaloids from Xanthorhiza simplicissima.  


The organic extract of the whole plant Xanthorhiza simplicissima was found to exhibit good activity against the AIDS-related opportunistic pathogens Candida albicans, Cryptococcus neoformans, and Mycobacterium intracellularae. Bioassay-directed fractionation of the extract led to the isolation of the known alkaloid berberine as the major active component. A second alkaloid of the isohomoprotoberberine family, puntarenine, was isolated from this plant family for the first time. Puntarenine also showed marginal activity against the dermatophytic fungus Trichophyton mentagrophytes and the yeast Saccharomyces cerevisiae. PMID:8207690

Okunade, A L; Hufford, C D; Richardson, M D; Peterson, J R; Clark, A M



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



Probing chemical space with alkaloid-inspired libraries.  


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

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



Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae  

Microsoft Academic Search

The benzylisoquinoline alkaloids (BIAs) are a diverse class of metabolites that exhibit a broad range of pharmacological activities and are synthesized through plant biosynthetic pathways comprised of complex enzyme activities and regulatory strategies. We have engineered yeast to produce the key intermediate reticuline and downstream BIA metabolites from a commercially available substrate. An enzyme tuning strategy was implemented that identified

Kristy M Hawkins; Christina D Smolke



Photochemical N-demethylation of alkaloids.  


Certain alkaloids were observed to undergo N-demethylation processes under photochemical conditions. Tropine, acetyltropine, tropinone, and atropine were cleanly N-demethylated upon treatment with tetraphenylporphin, oxygen, and light. Dextromethorphan also underwent a N-demethylation reaction, but reacted further to afford an imine. In contrast, 14-acyloxycodeinones underwent a photochemically induced tandem N-demethylation acyl migration. PMID:11229743

Ripper, J A; Tiekink, E R; Scammells, P J



A new alkaloid antibiotic tetrazomine. Structure determination.  


A new alkaloid antibiotic tetrazomine was isolated from the culture broth of Saccharothrix mutabilis subsp. chichijimaensis subsp. nov., and its structure was determined to be I by means of spectroscopic measurements. It has an unusual structure which consists of six rings, including piperidine, piperazine, oxazole, and pyrrolidine rings. PMID:1778788

Sato, T; Hirayama, F; Saito, T; Kaniwa, H



Bioactive heterocycle alkaloids and methods of use  

US Patent & Trademark Office Database

Novel heterocyclic alkaloids were isolated from a marine sponge. These compounds, and derivatives thereof, are useful antifungal and antitumor compounds. The novel compounds have the following structures: ##STR1## wherein R.sub.1 =H, alkyl, alkenyl, aryl, benzyl, acyl, benzoyl, or alkali metal; R.sub.2 and R'.sub.2 =O, S, NOX, or NNHX, wherein X is alkyl or aryl.



Four new Amaryllidaceae alkaloids from Zephyranthes candida.  


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



Pharmacokinetics of Hoasca alkaloids in healthy humans.  


N,N-Dimethyltryptamine (DMT), harmine, harmaline and tetrahydroharmine (THH) are the characteristic alkaloids found in Amazonian sacraments known as hoasca, ayahuasca, and yajč. Such beverages are characterized by the presence of these three harmala alkaloids, where harmine and harmaline reversibly inhibit monoamine oxidase A (MAO-A) while tetrahydroharmine weakly inhibits the uptake of serotonin. Together, both actions increase central and peripheral serotonergic activity while facilitating the psychoactivity of DMT. Though the use of such 'teas' has be known to western science for over 100 years, little is known of their pharmacokinetics. In this study, hoasca was prepared and administered in a ceremonial context. All four alkaloids were measured in the tea and in the plasma of 15 volunteers, subsequent to the ingestion of 2 ml hoasca/kg body weight, using gas (GC) and high pressure liquid chromatographic (HPLC) methods. Pharmacokinetic parameters were calculated and peak times of psychoactivity coincided with high alkaloid concentrations, particularly DMT which had an average Tmax of 107.5 +/- 32.5 min. While DMT parameters correlated with those of harmine, THH showed a pharmacokinetic profile relatively independent of harmine's. PMID:10404423

Callaway, J C; McKenna, D J; Grob, C S; Brito, G S; Raymon, L P; Poland, R E; Andrade, E N; Andrade, E O; Mash, D C



Cytotoxic isoquinoline alkaloids from Xanthorhiza simplicissima.  


Two cytotoxic isoquinoline alkaloids, liriodenine and palmatine, were isolated from the Xanthorhiza simplicissima Marsh. Liriodenine, isolated for the second time from the family of Ranunculaceae, demonstrated potent cytotoxicity against KB, A-549, HCT-8, P-388, and L-1210 tumor cells, while palmatine showed marginal cytotoxicity against KB cells. PMID:2810448

Wu, Y C; Yamagishi, T; Lee, K H



27 CFR 21.99 - Brucine alkaloid.  

Code of Federal Regulations, 2013 CFR

...d) Sulfate test. No white precipitate is formed that is not dissolved by hydrochloric acid when several drops of a 1 N barium chloride solution are added to 10 ml of a solution of the alkaloid. [T.D. ATF-133, 48 FR 24673, June 2, 1983....



Fluorescence lifetimes of some Rauwolfia alkaloids  

NASA Astrophysics Data System (ADS)

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

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



Amides and an alkaloid from Portulaca oleracea.  


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

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



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


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

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



Alkaloids isolated from natural herbs as the anticancer agents.  


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

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



Alkaloids Isolated from Natural Herbs as the Anticancer Agents  

PubMed Central

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

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



Pyrrolizidine alkaloid profiles of some Senecio species from Egypt.  


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



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.

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



Synthesis of the Marine Pyrroloiminoquinone Alkaloids, Discorhabdins  

PubMed Central

Many natural products with biologically interesting structures have been isolated from marine animals and plants such as sponges, corals, worms, etc. Some of them are discorhabdin alkaloids. The discorhabdin alkaloids (discorhabdin A-X), isolated from marine sponges, have a unique structure with azacarbocyclic spirocyclohexanone and pyrroloiminoquinone units. Due to their prominent potent antitumor activity, discorhabdins have attracted considerable attention. Many studies have been reported toward the synthesis of discorhabdins. We have accomplished the first total synthesis of discorhabdin A (1), having the strongest activity in vitro among discorhabdins in 2003. In 2009, we have also accomplished the first total synthesis of prianosin B (2), having the 16,17-dehydropyrroloiminoquinone moiety, by a novel dehydrogenation reaction with a catalytic amount of NaN3. These synthetic studies, as well as syntheses of the discorhabdins by various chemists to-date, are reviewed here.

Wada, Yasufumi; Fujioka, Hiromichi; Kita, Yasuyuki



Cyclopeptide alkaloids from Scutia buxifolia Reiss.  


Scutianene E (1), 3,4,28-tris-epi-scutiaene E (2), 28-epi-scutianene E (3) and scutianene L (4), four neutral cyclopeptide alkaloids, were isolated from Scutia buxifolia Reiss, together with four known cyclopeptide alkaloids, scutianines B, C, D and E. Scutianenes 1-3 are diastereoisomeric compounds, with 3-hydroxyleucine as a ?-hydroxy amino acid unit, which is connected to the styryl fragment via an ether bridge, ?-phenylserine, as a common ring-bonded amino acid residue. Attached to the amino group of ?-hydroxyamino acid is a side chain [trans-CH=CH-Ph]. The structures of the peptides were elucidated by means of spectroscopic analysis, including extensive 2D NMR studies. The stereochemistry for the diastereomeric 3,4,28-tris-epi-scutiaene E and 28-epi-scutianene E was confirmed by X-ray diffraction analysis of their O-acetyl derivatives. PMID:21420695

Maldaner, Graciela; Marangon, Patricia; Ilha, Vinicius; Caro, Miguel S Balparda; Burrow, Robert A; Dalcol, Ionara Irion; Morel, Ademir F



Total synthesis of the Daphniphyllum alkaloid daphenylline  

NASA Astrophysics Data System (ADS)

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

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



A new cyclopeptide alkaloid from the bark of waltheria douradinha  

Microsoft Academic Search

Waltherine-C (5), a novel 14-membered cyclopeptide alkaloid has been isolated, together with four known cyclopeptide alkaloids, waltherine-A (1) and -B (2), scutianine-B (3) and adouetine-Y' (4), from the bark of Waltheria douradinha (Sterculiaceae) from Rio Grande do Sul, Brazil. The structure and NMR assignments of this new alkaloid were determined by 1D and 2D NMR techniques. The stereochemistry of the

Ademir F. Morel; Adriana Flach; Nilo Zanatta; Eduardo M. Ethur; Marco A. Mostardeiro; Ilaine T. S. Gehrke



Antiplasmodial sesquiterpene alkaloids from the roots of Maytenus mekongensis.  


Eight new sesquiterpene alkaloids (1-8) and four known sesquiterpene alkaloids (9-12) have been isolated from the roots of Maytenus mekongensis. Structures were determined using extensive spectroscopic methods. The relative configuration of 7-epi-mekongensine (2) was established by single-crystal X-ray crystallographic analysis. The alkaloids were evaluated for antiplasmodial activity against Plasmodium falciparum, K1 strain, and for cytotoxicity using a panel of cell lines. PMID:21634414

Lhinhatrakool, Thitima; Prabpai, Samran; Kongsaeree, Palangpon; Sutthivaiyakit, Somyote



A new monoterpenoid oxindole alkaloid from Hamelia patens micropropagated plantlets.  


Chemical studies on Hamelia patens (Rubiaceae) micropropagated plantlets allowed production of a new monoterpenoid oxindole alkaloid, named (-)-hameline (7), together with eight known alkaloids, tetrahydroalstonine (1), aricine (2), pteropodine (3), isopteropodine (4), uncarine F (5), speciophylline (6), palmirine (8), and rumberine (9). The structure of the new alkaloid was assigned on the basis of 1D and 2D NMR spectroscopy, mass spectrometry, and molecular modeling. PMID:23285803

Paniagua-Vega, David; Cerda-García-Rojas, Carlos M; Ponce-Noyola, Teresa; Ramos-Valdivia, Ana C



Piperidine alkaloids from Chinese mangrove Sonneratia hainanensis.  


A new diphenacyl-piperidine alkaloid, sonneratine A (2), identified as a piperidine ring bearing two phenacyl substitutes at C-2 and C-6, and a known related derivative, (+/-)1-(2-piperidyl)-4-( P-methoxyphenyl)-butanone-2 (3), were isolated from the leaves and stems of the Hainan mangrove Sonneratia hainanensis. The structure of the new compound was determined by extensive analysis of its spectroscopic data and by comparison of its NMR data with those reported in the literature. PMID:20108179

Liu, Hai-Li; Huang, Xiao-Yin; Dong, Mei-Ling; Xin, Guo-Rong; Guo, Yue-Wei



A new benzophenanthridine alkaloid from Zanthoxylum buesgenii.  


A new benzophenanthridine alkaloid, 6-[2'-ethoxy-2'-(2'',4'',5''-trimethoxyphenyl)] ethyl-7,8-dimethoxy-5-methyl-2,3-methylenedioxy-5,6-dihydrobenzo[c]phenanthridine named buesgeniine (1), as well as the known decarine, were isolated from the extract of the stem bark of Zanthoxylum buesgenii. In addition, three known lignans, sesamine, matairesinol dimethylether, and methylpluviatilol, were also identified. The structure of 1 was elucidated using spectroscopic methods. PMID:16242267

Tane, Pierre; Wabo, Hippolyte K; Connolly, Joseph D



Berberine: A naturally occurring phototoxic alkaloid  

Microsoft Academic Search

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

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



Unique monoterpenoid indole alkaloids from Alstonia scholaris.  


[structure: see text] A pair of geometrically isomeric monoterpenoid indole alkaloids with a skeleton rearrangement and two additional carbons, named (19,20) E-alstoscholarine (1) and (19,20) Z-alstoscholarine (2), were obtained from the leaf extract of Alstonia scholaris. Their structures were elucidated on the basis of spectroscopic methods and then confirmed by X-ray crystal diffraction. The biogenesis of these compounds was also proposed. PMID:17391042

Cai, Xiang-Hai; Du, Zhi-Zhi; Luo, Xiao-Dong



A new diketopiperazine alkaloid from Aspergillus oryzae.  


Investigation of bioactive secondary metabolites from terrestrial Aspergillus oryzae sp. MMAO1 using M2 medium afforded a new diketopiperazine alkaloid, 7,9-dihydroxy-3-(1H-indol-3-ylmethyl)-8-methoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione (1a), containing the unusual amino acid L-6,8-dihydroxy-7-methoxyphenylalanine. This was co-isolated with ditryptophenaline (2), cyclo-(Tryp,Tyr) (4), cyclo-(Pro,Val), ?-cyclopiazonic acid (3), kojic acid and uridine. Re-cultivation of the fungal strain on Dox medium led to the production of bisdethio(bismethylthio)gliotoxin (5), pseurotin A (6) along with linoleic acid, ?-cyclopiazonic acid (3) and kojic acid. The chemical structure of the new diketopiperazine alkaloid including the relative configuration was determined by 1D and 2D NMR spectroscopy and HR-ESI-MS spectrometry, and by comparison with the related literature. The new alkaloid (1a) showed no antimicrobial activity or cytotoxicity against brine shrimps. PMID:24116376

Shaaban, Mohamed; El-Metwally, Mohammad Magdy; Nasr, Hamdi



Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla.  


A total of seventeen alkaloids, comprising six macroline (including alstofolinine A, a macroline indole incorporating a butyrolactone ring-E), two ajmaline, one sarpagine, and eight akuammiline alkaloids, were isolated from the stem-bark and leaf extracts of the Malayan Alstonia macrophylla. The structure and relative configurations of these alkaloids were established using NMR, MS and in several instances, confirmed by X-ray diffraction analysis. Six of these alkaloids were effective in reversing multidrug-resistance (MDR) in vincristine-resistant KB cells. PMID:24342109

Lim, Siew-Huah; Low, Yun-Yee; Sinniah, Saravana Kumar; Yong, Kien-Thai; Sim, Kae-Shin; Kam, Toh-Seok



Indole alkaloids from the leaves of Philippine Alstonia scholaris.  


The first seco-uleine alkaloids, manilamine (1) (18-hydroxy-19,20-dehydro-7,21-seco-uleine) and N4-methyl angustilobine B (2), were isolated from the (pH 5) alkaloid extract of Philippine Alstonia scholaris leaves together with the known indole alkaloids 19,20-(E)-vallesamine (3), angustilobine B N4-oxide (4), 20(S)-tubotaiwine (5), and 6,7-seco-angustilobine B (6). The structure of the alkaloids was established from MS and NMR experiments. PMID:15924920

Macabeo, Allan Patrick G; Krohn, Karsten; Gehle, Dietmar; Read, Roger W; Brophy, Joseph J; Cordell, Geoffrey A; Franzblau, Scott G; Aguinaldo, Alicia M



Indole alkaloids from the leaves of Philippine Alstonia scholaris  

Microsoft Academic Search

The first seco-uleine alkaloids, manilamine (1) (18-hydroxy-19,20-dehydro-7,21-seco-uleine) and N4-methyl angustilobine B (2), were isolated from the (pH 5) alkaloid extract of Philippine Alstonia scholaris leaves together with the known indole alkaloids 19,20-(E)-vallesamine (3), angustilobine B N4-oxide (4), 20(S)-tubotaiwine (5), and 6,7-seco-angustilobine B (6). The structure of the alkaloids was established from MS and NMR experiments.

Allan Patrick G. Macabeo; Karsten Krohn; Dietmar Gehle; Roger W. Read; Joseph J. Brophy; Geoffrey A. Cordell; Scott G. Franzblau; Alicia M. Aguinaldo



Bioactive alkaloid extracts from Narcissus broussonetii: mass spectral studies.  


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

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



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


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



Reduction of venom alkaloids in Solenopsis richteri×Solenopsis invicta hybrid: an attempt to identify new alkaloidal components.  


The alkaloid chemistry of the venom of hybrid fire ant, Solenopsis richteri × Solenopsis invicta, was investigated using silica gel chromatography and GC-MS techniques. In addition to most cis alkaloids of parental species, S. richteri Forel and S. invicta Buren, the cis alkaloid fraction of the body extract of hybrid fire ants also contains five significant new alkaloids. Hydrogenation of the cis alkaloid fraction yielded only five piperidines, 4', 12', 12, 20', and 20. Sodium borohydride and lithium aluminum hydride selectively reduced C?N double bond in piperideine alkaloids to give a mixture of cis and trans piperidines. However, reduction of the five new components yielded several new peaks with much longer retention times and increasing molecular weights over 30. It is evident that the chemical identities of the five new peaks are quite different from those known piperidines or piperideines found in Solenopsis fire ants. PMID:20964344

Chen, Li; Hu, Qiong-Bo; Fadamiro, Henry Y



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


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



Cyclopeptide alkaloids. Phencyclopeptines from the polymorphic species Ceanothus integerrimus  

Microsoft Academic Search

Seven cyclopeptide alkaloids, phencyclopeptines 1-7, have been found distributed among three forms of the shrub Ceanothus integerrimus. Chemical degradation, mass spectroscopy, and ÂąH nmr spectroscopy have established structures for these seven compounds, three of which have been previously reported. The use of cyclopeptide alkaloid structure and distribution for chemotaxonomic assignments is discussed.

J. Clark Lagarias; Dane Goff; Frederick K. Klein; Henry Rapoport



Total syntheses and antimicrobial activities of pyridine alkaloids from Rubiaceae  

Microsoft Academic Search

Pyridine alkaloids from Rubiaceae were prepared by palladium-catalyzed cross-coupling reactions of methyl 5-bromonicotinate (6) with various organometallic reagents. Baker's yeast reduction of the ketone8 gave the levorotatory alcohol (S)-1. On this basis, the naturally occurring alcohol (+)-1 was assigned to be (R)-configurated. The alkaloids1 and4 show weak antimicrobial activities.

F. Bracher; T. Papke



Carbazole alkaloid with antimicrobial activity from clausena heptaphylla  

Microsoft Academic Search

A new carbazole alkaloid designated as clausenal was isolated from the leaves of Clausena heptaphylla and its structure established as 1,8-dimethoxy-3-formylcarbazole from physical, chemical and synthetic evidence. The alkaloid was found to be active against both Gram-positive and Gram-negative bacteria, and fungi.

A. Chakraborty; C. Saha; G. Podder; B. K. Chowdhury; P. Bhattacharyya



Indole alkaloids from leaves and twigs of Rauvolfia verticillata.  


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

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



A new alkaloid isolated from Abies webbiana leaf  

PubMed Central

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

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



A cyclized didemnimide alkaloid from the caribbean ascidian didemnumconchyliatum  


A novel, cyclized alkaloid of the didemnimide class, 5, has been isolated from extracts of the Caribbean ascidian Didemnum conchyliatum. The structure of 5 was assigned using combined spectral methods that emphasized one- and two-dimensional NMR methods. The new alkaloid is the cyclization product of didemnimide A (1) formed via a C-2 indole condensation with the imidazole nitrogen. PMID:10075798

Vervoort; Fenical; Keifer



A cage-monoterpene indole alkaloid from Alstonia scholaris.  


An unprecedented cage-like alkaloid, scholarisine A was isolated from the leaves of Alstonia scholaris and its structure determined on the basis of 1D and 2D NMR, FTIR, UV, and high-resolution mass spectroscopic data. This alkaloid might be derived from picrinine via oxygenation, rearrangement, and lactonization. PMID:18205369

Cai, Xiang-Hai; Tan, Qin-Gang; Liu, Ya-Ping; Feng, Tao; Du, Zhi-Zhi; Li, Wei-Qi; Luo, Xiao-Dong



New monoterpenoid alkaloids from the aerial parts of Uncaria hirsuta.  


To investigate the chemical constituents of medicinal plant Uncaria hirsuta, three new monoterpenoid alkaloids, named hirsutanines A-C (1-3), were isolated. Their structures with absolute configurations were elucidated by means of NMR, X-ray diffraction and CD analysis. Compound 3 was the first dimeric monoterpenoid alkaloid obtained from genus Uncaria. PMID:24684175

Jia, Jun-Feng; Zhang, Yuan; Huang, Xiao-Jun; Zhang, Sheng-Yuan; Tian, Hai-Yan; Wang, Lei; Ye, Wen-Cai



Aporphine alkaloids of Cinnamomum mollissimum and their bioactivities.  


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

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



Anti-inflammatory activity of diterpene alkaloids from Aconitum baikalense.  


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

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



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


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



Bioactive alkaloids from endophytic Aspergillus fumigatus.  


Two new alkaloids, named 9-deacetylfumigaclavine C (1) and 9-deacetoxyfumigaclavine C (2), along with 12 known compounds (3-14), were isolated from the culture of Aspergillus fumigatus. The structures of the new compounds were elucidated by comprehensive spectroscopic analyses. Compound 2 showed selectively potent cytotoxicity against human leukemia cells (K562) with an IC(50) value of 3.1 microM, which was comparable to that of doxorubicin hydrochloride, a presently prescribed drug for the treatment of leukemia. Furthermore, 14-norpseurotin (4) significantly induced neurite outgrowth of rat pheochromocytoma cells (PC12) at a 10.0 microM concentration. PMID:19256529

Ge, Hui Ming; Yu, Zhi Guo; Zhang, Jie; Wu, Jun Hua; Tan, Ren Xiang



Total synthesis of the biphenyl alkaloid (-)-lythranidine.  


A sequence comprising a ring-closing alkyne metathesis of a propargyl alcohol derivative, followed by a ruthenium-catalyzed redox isomerization of the derived cycloalkyne and a transannular aza-Michael addition allowed the formation of the distinguishing piperidine-metacyclophane framework of the Lythraceum alkaloid lythanidine in a few high-yielding steps. This application attests to the excellent functional-group tolerance of a molybdenum alkylidyne complex endowed with triphenylsilanolate ligands, which enabled the macrocyclization even in the presence of protic functionalities, and thus illustrates the power of contemporary catalytic acetylene chemistry for target-oriented synthesis. PMID:24821137

Gebauer, Konrad; Fürstner, Alois



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.


Elimination of ergoline alkaloids following treatment of Ipomoea asarifolia (Convolvulaceae) with fungicides  

Microsoft Academic Search

Ergoline alkaloids are constituents of Clavicipitaceous fungi living on Poaceae plants. Ergoline alkaloids as well as volatile oil are also present in Ipomoea asarifolia Roem. & Schult (Convolvulaceae). Treatment of this plant with two fungicides (Folicur, Pronto Plus) eliminates the ergoline alkaloids but not the volatile oil. Elimination of ergoline alkaloids occurs concomitantly with loss of fungal hyphae associated with

Sabine Kucht; Julia Groß; Yasser Hussein; Torsten Grothe; Ullrich Keller; Simla Basar; Wilfried A. König; Ulrike Steiner; Eckhard Leistner



[Cytotoxic alkaloids from stems of Nelumbo nucifera].  


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

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



A new cytotoxic carbazole alkaloid and two new other alkaloids from Clausena excavata.  


One new carbazole alkaloid, excavatine A (1), and two additional new alkaloids, excavatine B (2) and excavatine C (3), were isolated from the stems and leaves of Clausena excavata Burm.f. (Rutaceae). Their structures were determined on the basis of detailed spectroscopic analyses, especially 2D-NMR and HR-EI-MS data. Compounds 1-3 were tested for their cytotoxic activities against A549, HeLa, and BGC-823 cancer cell lines, and for their antimicrobial activities against Candida albicans and Staphylococcus aureus. Only 1 exhibited cytotoxicity against A549 and HeLa cell lines with the IC50 values of 5.25 and 1.91??g/ml, respectively. PMID:23847076

Peng, Wen-Wen; Zeng, Guang-Zhi; Song, Wei-Wu; Tan, Ning-Hua



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.

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



New indole alkaloids from the bark of Alstonia scholaris.  


A new indole alkaloid, akuammiginone (1), and a new glycosidic indole alkaloid, echitamidine-N-oxide 19-O-beta-d-glucopyranoside (2), together with the five known alkaloids, echitaminic acid (3), echitamidine N-oxide (4), N(b)-demethylalstogustine N-oxide (5), akuammicine N-oxide (6), and N(b)-demethylalstogustine (7), were isolated from the trunk bark of Alstonia scholaris collected in Timor, Indonesia. The structures of all compounds were elucidated by spectroscopic methods. This is the first report of compounds 3-5and 7 in A. scholaris. Some NMR assignments of the known compounds were revised. PMID:15387668

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



Cytotoxic Alangium alkaloids from Alangium longiflorum.  


Seven alkaloids (1-7) were isolated from the stem bark of Alangium longiflorum. Compound 1, (-)-10-O-demethylisocephaeline, was isolated for the first time as a naturally occurring product from a plant source. All structures were elucidated by detailed spectroscopic analysis. Biological evaluation showed that 2, 10-O-demethylcephaeline, exhibited potent cytotoxic activity against human lung carcinoma (A549) and breast adenocarcinoma (MCF-7) with ED(50) values of 0.013 and 0.062 microM, respectively. The stereoisomer 1 was less potent than 2, and related compounds with different hydroxy/methoxy substitution patterns were also less potent or inactive. Thus, compound 2 merits attention as a cytotoxic lead for further study. PMID:16530796

Sakurai, Nobuko; Nakagawa-Goto, Kyoko; Ito, Junko; Sakurai, Yojiro; Nakanishi, Yuka; Bastow, Kenneth F; Cragg, Gordon; Lee, Kuo-Hsiung



Synthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids  

PubMed Central

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

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



Total Synthesis and Study of Myrmicarin Alkaloids  

PubMed Central

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

Ondrus, Alison E.



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.

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



Bioactive isoquinoline alkaloids from Corydalis saxicola.  


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

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



Benhamycin, novel alkaloid from terrestrial Streptomyces sp.  


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

Shaaban, Mohamed; Abdel-Aziz, Mohamed S



Pyrrolidonyl and pyridyl alkaloids in Lymantria dispar.  


The occurrence and metabolism of nicotine and related N-containing compounds in body fluids of the gipsy moth were addressed. Thin layer chromatographic studies clearly showed the simultaneous presence of GABA and 2-pyrrolidone but not of GABamide in the larval haemolymph and osmeterial secretion of Lymantria dispar as well as in the corresponding body fluids of the saturniids, Saturnia pavonia and Attacus atlas. Furthermore, feeding and injection experiments using alkylated precursors and combined gas chromatography/mass spectrometry gave evidence of the transformation of 2-pyrrolidone to nicotine and of nicotinic acid to nicotinamide in caterpillars of L. dispar. Based on these results, on the earlier described variation of the secondary-compound patterns of L. dispar during its development, and on literature data, metabolic pathways for the hitherto detected pyridyl and pyrrolidonyl alkaloids in Lymantriidae (and possibly Saturniidae) are proposed. PMID:14713166

Deml, Reinhold



Two new 14-membered cyclopeptide alkaloids from Zizyphus xylopyra.  


The phytochemical investigation of the bark of Zizyphus xylopyra resulted in the isolation of two new 14-membered ring cyclopeptide alkaloids, xylopyrine-G and xylopyrine H. Their structures have been established by chemical and spectral evidences. PMID:21995325

Pandey, Manoj B; Singh, Sarita; Malhotra, Meenakshi; Pandey, Vidya B; Singh, Tryambak D



Huperzine P, a novel Lycopodium alkaloid from Huperzia serrata  

Microsoft Academic Search

Huperzine P (1), a new irregular fawcettimine-type Lycopodium alkaloid, was isolated from Huperziaserrata and the absolute stereostructure was established by 2D NMR and X-ray crystallographic analysis.

Chang-Heng Tan; Shan-Hao Jiang; Da-Yuan Zhu



Structure-cardiac activity relationship of C19-diterpenoid alkaloids.  


Thirty three C19-diterpenoid alkaloids, twenty-two prepared from known C19-diterpenoid alkaloids and eleven isolated from Aconitum and Delphinium spp. were evaluated for their cardiac activity in the isolated bullfrog heart assay. Among them, eleven compounds exhibited cardiac activity, with average rate of amplitude increase in the range of 16-118%. Compound 7, mesaconine (17), hypaconine (25), and beiwutinine (26) exhibited strong cardiac activities relative to the reference drug. The structure-activity relationship data acquired indicated that an alpha-hydroxyl group at C-15, a hydroxyl group at C-8, an alpha-methoxyl or hydroxyl group at C-1, and a secondary amine or N-methyl group in ring A are important structure features necessary for the cardiac activities of the aconitine-type C19-diterpenoid alkaloids without any ester groups. In addition, an alpha-hydroxyl group at C-3 is also helpful for the cardiac activity of these alkaloids. PMID:22816290

Jian, Xi-Xian; Tang, Pei; Liu, Xiu-Xiu; Chao, Ruo-Bing; Chen, Qiao-Hong; She, Xue-Ke; Chen, Dong-Lin; Wang, Feng-Peng



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.



Marine bromopyrrole alkaloids: synthesis and diverse medicinal applications.  


Marine organisms have been found to be a very rich source of bioactive molecules. Among marine organisms, sponges have been proven to be excellent producers of secondary metabolites. More than 5,300 compounds have been isolated from sponges with around 200 new molecules reported each year. Bromopyrrole alkaloids constitute a family of exclusively marine alkaloids and represent a fascinating example of the large variety of compounds formed by marine sponges which exhibit different biological activities such as antifeedent, anti-biofilm, anticancer, antiinflammatory, antimicrobial, immunomodulatory, analgesic, antiserotonergic, antiangiogenic, antihistaminic, chitinase inhibitor and actimyosin ATPase activator. More than 140 derivatives with different structures and biological activities, have been isolated from more than 20 different sponges. Most of these alkaloids share a key building block, pyrrole-imidazole with oroidin being their underlying structural motif. In this review detailed account of isolation and medicinal application of marine bromopyrrole alkaloids and their synthetic derivatives are discussed. PMID:24359195

Rane, Rajesh; Sahu, Niteshkumar; Shah, Chetan; Karpoormath, Rajshekhar



Structure revision of the marine pentacyclic aromatic alkaloid: cystodamine  

Microsoft Academic Search

The structure of cystodamine, a polycyclic aromatic alkaloid from the mediterranean ascidian Cystodytes delle chiajei has been revised to be 11-hydroxyascididemin, by comparison of the spectroscopic data with those of synthetic cystodamine, meridine and 11-hydroxyascididemin.

Evelyne Delfourne; Nataly Bontemps-Subielos; Jean Bastide



Two new alkaloids from the bark of Sarcomelicope megistophylla.  


Two new alkaloids, megistophylline I (1) and megistophylline II (2), were isolated from the bark of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of MS and NMR data. PMID:10757725

Papageorgiou, M; Fokialakis, N; Mitaku, S; Skaltsounis, A L; Tillequin, F; Sévenet, T



Megistosarcimine and megistosarconine, two alkaloids from Sarcomelicope megistophylla.  


Two new alkaloids, megistosarcimine and megistosarconine, were isolated from the aerial parts of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of their spectral data and molecular modeling. PMID:10647223

Fokialakis, N; Mitaku, S; Mikros, E; Skaltsounis, A L; Tillequin, F; Sevenet, T



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


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

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



Tambjamine alkaloids and related synthetic analogs: efficient transmembrane anion transporters.  


The tambjamine alkaloids and related synthetic analogs are potent transmembrane anion tranporters promoting bicarbonate/chloride exchange in model phospholipid liposomes and discharging pH gradients in living cells. PMID:21528145

Iglesias Hernández, Paulina; Moreno, Daniel; Javier, Anatalia Araujo; Torroba, Tomás; Pérez-Tomás, Ricardo; Quesada, Roberto



Leishmanicidal evaluation of tetrahydroprotoberberine and spirocyclic erythrina-alkaloids.  


Leishmaniasis is one of the World's most problematic diseases in developing countries. Traditional medicines to treat leishmaniasis have serious side effects, as well as significant parasite resistance problems. In this work, two alkaloids 1 and 2 were obtained from Corydalis govaniana Wall and seven alkaloids 3-9, were obtained from Erythrina verna. The structures of the compounds were confirmed by mass spectrometry and 1D- and 2D-NMR spectroscopy. The leishmanicidal activity of compounds 1-9 against Leishmania amazonensis was tested on promastigote forms and cytotoxicity against J774 (macrophage cell line) was assessed in vitro. Compound 1 showed potent activity (IC50 = 0.18 µg/mL), compared with the standard amphotericin B (IC50 = 0.20 µg/mL). The spirocyclic erythrina-alkaloids showed lower leishmanicidal activity than dibenzoquinolizine type alkaloids. PMID:24802983

Callejon, Daniel R; Riul, Thalita B; Feitosa, Luis G P; Guaratini, Thais; Silva, Denise B; Adhikari, Achyut; Shrestha, Ram L S; Marques, Lucas M M; Baruffi, Marcelo D; Lopes, Joăo L C; Lopes, Norberto P



Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine  

Microsoft Academic Search

The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alcohol to a ketone.

Alessio Barilli; Francesca Belinghieri; Daniele Passarella; Giordano Lesma; Sergio Riva; Alessandra Silvani; Bruno Danieli



Concentrations of ephedra alkaloids and caffeine in commercial dietary supplements.  


Dietary supplements that contain Ma Huang (ephedra alkaloids) and guarana (caffeine) are widely marketed and used in the U.S. for weight loss and athletic performance enhancement, despite a lack of adequate research on the pharmacology of these botanical stimulants. We developed and applied a novel liquid chromatography-tandem mass spectrometry (LC-MS-MS) method to quantitate the various ephedra alkaloids found in dietary supplements that contain Ephedra species. The quantities of ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, methylephedine, methylpseudoephedrine, and caffeine were determined for 35 commercial dietary supplements and compared with the amounts listed on the product labels. The total ephedra alkaloid content ranged from 5.97 mg to 29.3 mg per serving. Two supplement brands did not list the quantity of ephedra alkaloids on the label, and four did not list the amount of caffeine per serving. Of the products tested, 31% contained > 110% of the total ephedra alkaloids listed on the label, and 6% of the supplements contained < 90% of the listed amount. For caffeine, 86% of the product lots that listed the caffeine amount contained less than 90% of the labeled quantity. No products contained > 110% of the declared caffeine content. The total ephedra alkaloid content varied significantly from lot to lot in 5 of 9 products. Three product brands contained proportions of alkaloids that exceeded amounts reported for E. sinica, including one that was 98% ephedrine, one that had 10% norpseudoephedrine, and one that contained an average of 13% methylephedrine. We conclude that product inconsistency is common among some commercially available dietary supplements that contain ephedra alkaloids and caffeine. PMID:15107143

Haller, Christine A; Duan, Minjing; Benowitz, Neal L; Jacob, Peyton



Detection and quantification of pyrrolizidine alkaloids in antibacterial medical honeys.  


In recent years, there has been an increasing interest in antibacterial honey for wound care ranging from minor abrasions and burns to leg ulcers and surgical wounds. On the other hand, several recent studies demonstrated that honey for human consumption was contaminated with natural occurring, plant derived pyrrolizidine alkaloids.1,2-Unsaturated pyrrolizidine alkaloids are a group of secondary plant metabolites that show developmental, hepato-, and geno-toxicity as well as carcinogenic effects in animal models and in in vitro test systems. Hence, it was of particular interest to analyze the pyrrolizidine alkaloid content of medical honeys intended for wound care.19 different medical honey samples and/or batches were analyzed by applying a recently established pyrrolizidine alkaloid sum parameter method. 1,2-Unsaturated pyrrolizidine alkaloids were converted into the common necin backbone structures and were analyzed and quantified by GC-MS in the selected ion monitoring mode.All but one medical honey analyzed were pyrrolizidine alkaloid positive. The results ranged from 10.6?µg retronecine equivalents per kg to 494.5?µg retronecine equivalents/kg medical honey. The average pyrrolizidine alkaloid content of all positive samples was 83.6?µg retronecine equivalents/kg medical honey (average of all samples was 79.3?µg retronecine equivalents/kg medical honey). The limit of detection was 2.0?µg retronecine equivalents/kg medical honey, while the limit of quantification was 6.0?µg retronecine equivalents/kg medical honey (S/N?>?7/1).Based on the data presented here and considering the fact that medical honeys can be applied to open wounds, it seems reasonable to discuss the monitoring of 1,2-unsaturated pyrrolizidine alkaloids in honey intended for wound treatment. PMID:23161425

Cramer, Luise; Beuerle, Till



Alkaloids from roots of Stemona sessilifolia and their antitussive activities.  


Protostemonamide ( 1), a new protostemonine-type alkaloid, and 12 known compounds were isolated from the roots of Stemona sessilifolia. Their structures were elucidated by 1 D and 2 D NMR spectral and other spectroscopic studies. The main alkaloidal constituents, protostemonine ( 2), stemospironine ( 4), and maistemonine ( 7), showed significant antitussive activity in a citric acid-induced guinea pig cough model following peripheral administration; stemonamine ( 11) had antitussive activity following i. c. v. administration. PMID:19031364

Yang, Xin-Zhou; Zhu, Jian-Yu; Tang, Chun-Ping; Ke, Chang-Qiang; Lin, Ge; Cheng, Tin-Yan; Rudd, John A; Ye, Yang



Microcalorimetric study on the bacteriostatic activity of isoquinoline alkaloids  

Microsoft Academic Search

The isoquinoline alkaloids were isolated from traditional Chinese drugs of Phellodendri Cortex, Radix Stephaniae Tetrandrae,\\u000a Corydalis Yanhusuo and Corydalis Bungeana. The power-time curves of growth of E. coli at different concentrations of isoquinoline alkaloid at 37?C were determined by a 2277 Thermal Activity Monitor. The rate\\u000a constant of bacteriostastic activity was calculated. The relationship between growth rate constant and concentration

X. J. Liu; H. L. Zhang; Z.-C. Tan; K. L. Han; L. X. Sun



Inhibition of acetyl cholinesterase by solanaceous glycoalkaloids and alkaloids  

Microsoft Academic Search

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

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



Quaternary Benzo[C]Phenanthridine Alkaloids — Biological Activities  

Microsoft Academic Search

\\u000a Quarternary benzo[c]phenanthridine alkaloids (QBA) are a small class of compounds commonly isolated from Caprifoliaceae, Fumariaceae,\\u000a Meliacea, Papaveraceae and Rutaceae plants. QBA belong to the elicitor-inducible secondary metabolites and are considered\\u000a phytoalexines because of their antifungal and nematocidal activities. Quaternary benzo[c]phenanthridine alkaloids whose most\\u000a studied representatives are sanguinarine (SA), chelerythrine (CHE), and fagaronine (FA) (Fig. 1) display a wide spectrum of

V. Šimánek; R. Vespalec; A. Šedo; J. Ulrichová; J. Vi?ar


Anticholinesterase inhibitory activity of quaternary alkaloids from Tinospora crispa.  


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

Yusoff, Mashitah; Hamid, Hazrulrizawati; Houghton, Peter



The effects of a selection of alkaloids on the invertase activity of some higher plants.  


The effects of several alkaloids on the invertase activities of Ricinus communis, Solanum tuberosum, Oryza sativa and Carica papaya were studied. The following alkaloids: caffeine, berberine, strychnine, morphine, ethyl-narceine and nornicotine, have different inhibitory effects on invertase activity. Kinetic studies of the alkaloid inhibition revealed that different alkaloids exhibited diverse types of inhibition of invertase. It was found that alkaloids form reversible complexes with invertases. However cocaine and potato glycoalkaloids were activators of some invertase. The sugar moiety of potato glycoalkaloids were also activators. It is concluded that alkaloids may be effectors of higher plant invertase activity. PMID:9442928

Rojo, H P; Quiroga, E N; Vattuone, M A; Sampietro, A R



Total synthesis of indoline alkaloids: A cyclopropanation strategy.  


Indoline alkaloids constitute a large class of natural products; their diverse and complex structures contribute to potent biological activities in a range of molecules. Designing an appropriate strategy for the total synthesis of indoline alkaloids is a difficult task that depends on being able to efficiently assemble the core architectures. The best strategies allow access to a variety of different indoline alkaloid structures in a minimum of steps. The cyclopropanation of simple olefins and the subsequent synthetic transformation of the resulting cyclopropyl intermediates has been intensively studied in recent decades. In contrast, the cyclopropanation of enamines, especially for the construction of complex nitrogen-containing ring systems, remained relatively unexplored. Previous success with the cyclopropanation of simple indoles to form stable indolylcyclopropanocarboxylates encouraged us to explore the assembly of indoline alkaloid skeletons with cyclopropanation as a key reaction. Theoretically, indolylcyclopropanocarboxylates are doubly activated by a vicinally substituted amino group and carboxyl group; that is, they are typical donor-acceptor cyclopropanes. Accordingly, they tend to yield an active iminium intermediate, which can undergo inter- and intramolecular nucleophilic reactions to form the core structure of indoline alkaloids with an expanded ring system. In this Account, we summarize our efforts to develop a cascade or stepwise reaction of cyclopropanation/ring-opening/iminium cyclization (the CRI reaction) on tryptamine derivatives for assembling indoline alkaloid skeletons. With the CRI approach, three types of indoline alkaloid skeletons have been efficiently constructed: (i) hexahydropyrrolo[2,3-b]indoline (type I), (ii) tetrahydro-9a,4a-iminoethano-9H-carbazole (type II), and (iii) tetrahydroquinolino[2,3-b]indoline (type III). The effects of substituents on tryptamine derivatives were carefully investigated for inter- and intramolecular CRI reactions during construction of type I and type II skeletons. These results provided a basis for the further design and synthesis of complex natural products containing nitrogen. The usefulness of the CRI reaction is well demonstrated by our total synthesis of structurally intriguing indoline alkaloids such as N-acetylardeemin, minfiensine, vincorine, and communesin F. In addition, we highlight advances by other groups in construction of the three types of skeletons as well as their total syntheses of these indoline alkaloids. Discussion of the total syntheses of these indoline alkaloids focuses on comparing the individual synthetic strategies for forming the ring systems embedded in the final products. We also describe the total synthesis of perophoramidine, which has the same type III skeleton as communesin F. The observation of a retro Diels-Alder reaction during our synthesis of communesin F inspired the hetero Diels-Alder reaction on which our total synthesis of perophoramidine was based. PMID:21491859

Zhang, Dan; Song, Hao; Qin, Yong



Pyrrolizidine alkaloids in honey and bee pollen.  


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



Isolation, Biosynthesis and Biological Activity of Alkaloids of Tylophora Asthmatica, a Versatile Medicinal Plant.  

National Technical Information Service (NTIS)

Tylophorine and related new alkaloids have been isolated from Tylophora asthmatics, Pergularia pallida and Ficus hispida plants. Biosynthesis of this group of alkaloids has been carried out using various labelled precursors for the first time and from the...

N. B. Mulchandani



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


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



Actions of piperidine alkaloid teratogens at fetal nicotinic acetylcholine receptors.  


Teratogenic alkaloids are found in many species of plants including Conium maculatum L., Nicotiana glauca, Nicotiana tabaccum, and multiple Lupinus spp. Fetal musculoskeletal defects produced by alkaloids from these plants include arthrogyropisis, scoliosis, torticollis, kyposis, lordosis, and cleft palate. A pharmacodynamic comparison of the alkaloids ammodendrine, anabasine, anabaseine, anagyrine, and coniine in SH-SY5Y cells and TE-671 cells was made. These alkaloids and their enantiomers were more effective in depolarizing TE-671 cells which express the human fetal-muscle type nicotinic acetylcholine receptor (nAChR) relative to SH-SY5Y cells which predominately express autonomic nAChRs. The rank order of potency in TE-671 cells was: anabaseine>(+)-anabasine>(-)-anabasine > (+/-)-anabasine>anagyrine>(-)-coniine > (+/-)-coniine>(+)-coniine>(+/-)-ammodendrine>(+)-ammodendrine. The rank order potency in SH-SY5Y cells was: anabaseine>(+)-anabasine>(-)-coniine>(+)-coniine>(+)-ammodendrine>anagyrine>(-)-anabasine>(+/-)-coniine>(+/-)-anabasine>(-)-ammodendrine. The actions of these alkaloids at nAChRs in both cell lines could be distinguished by their maximum effects in depolarizing cell membrane potential. The teratogenic action of these compounds may be related to their ability to activate and subsequently desensitize nAChRs. PMID:20116429

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



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.

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



In vitro organogenesis and alkaloid accumulation in Datura innoxia.  


The kinetics of tropane alkaloids accumulation in different organs such as roots, leaves, stems, flowers and seeds of Datura innoxia was investigated by GC-MS. Twenty-six tropane alkaloids were detected. The ester derivatives of tropine (3alpha-tigloyloxytropine and 3-tigloyloxy-6-hydroxytropine) are the major compounds. Undifferentiated callus were established from the stem explants of Datura innoxia using Murashige and Skoog (MS) medium supplied with 6-benzylaminopurine (BA, 1 mg l(-10) and indole-3-acetic acid (IAA, 0.5 mg l(-1)) in combination for 6 weeks. Callus differentiation was initiated by subculture onto solid MS medium, free from hormones, for more than 10 months. Initially, shoots were formed after four weeks from subculture. Further subculturing in basal MS medium without growth regulators initiated the rooting of a shooty callus after 6 weeks. Investigation of the alkaloid content of the unorganized and organized callus revealed that callus (either green or brown) yielded only trace amounts of alkaloids. On the other hand, re-differentiated shoots contained mainly scopolamine while re-differentiated roots biosynthesized hyoscyamine as the main alkaloid. PMID:16989317

Zayed, Rawia; Wink, Michael; El-Shamy, Hesham



Geographic distribution of three alkaloid chemotypes of Croton lechleri.  


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

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



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


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



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

Microsoft Academic Search

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

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



Furomegistines I and II, two furanopyridine alkaloids from the bark of Sarcomelicope megistophylla.  


Two alkaloids, furomegistine I (1) and furomegistine II (2), were isolated from the bark of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of MS and NMR data. Both belong to the category of furanopyridine alkaloids and should be considered as oxidation products of a furo[2,3-b]quinoline precursor. The two alkaloids exhibited moderate cytotoxic activity. PMID:11394864

Fokialakis, N; Magiatis, P; Aligiannis, N; Mitaku, S; Tillequin, F; Sévenet, T



Bioactive alkaloids of frog skin: Combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source  

Microsoft Academic Search

Nearly 500 alkaloids have been detected in skin extracts from frogs of the family Dendrobatidae. All seem to have been sequestered unchanged into skin glands from alkaloid-containing arthropods. Ants, beetles, and millipedes seem to be the source of decahydroquinolines, certain izidines, coccinellines, and spiropyrrolizidine oximes. But the dietary source for a major group of frog-skin alkaloids, namely the pumiliotoxins (PTXs),

John W. Daly; Tetsuo Kaneko; Jason Wilham; H. Martin Garraffo; Thomas F. Spande; Alex Espinosa; Maureen A. Donnelly



Alkaloids of Ochrosia poweri Bail, The Stereochemistry of Poweridine and the Identity of Elliptamine and Reserpiline  

Microsoft Academic Search

The alkaloid poweridine from Ochrosia poweri Bail. has been shown to have the same relative con- figuration as yohimbine. Elliptamine, previously obtained from 0. poweri, has been identified as reserpiline. A study of the proton and 13C nuclear magnetic resonance spectra of the alkaloid poweridine, isolated previously from the leaves of Ochrosia powevi Bail.,' has shown that this alkaloid has



Isodiplamine, cystodytin K and lissoclinidine: novel bioactive alkaloids from the New Zealand ascidian Lissoclinum notti  

Microsoft Academic Search

A study of the bioactive crude extract of the New Zealand ascidian Lissoclinum notti led to the isolation of the new pyridoacridine alkaloids isodiplamine (4), cystodytin K (5) and lissoclinidine (6), as well as the known pyridoacridine alkaloids diplamine (7) and cystodytin J (8) and the benzopentathiepin varacin (3) and related trithiane varacin A. The new alkaloids were characterised using

David R Appleton; A. Norrie Pearce; Gretchen Lambert; Russell C Babcock; Brent R Copp



Carboline alkaloids from Psammosilene tunicoides and their cytotoxic activities.  


Five new carboline alkaloids, tunicoidines A-E ( 1- 5), and two known carboline alkaloids, 1-acetyl-?-carboline-3-carboxylic acid ( 6) and 1-acetyl-3-carbomethoxyl- ?-carboline ( 7), were isolated for the first time from the root of Psammosilene tunicoides. The structures of the new carboline alkaloids were established on the basis of 1D- and 2D-NMR, and HR-MS spectroscopic analyses. The seven compounds were evaluated for cytotoxicity against A549, HCT116, ZR-75-30, and HL-60 cell lines. However, only compound 7 had potent cytotoxic activity against the HCT116 cell line with an IC (50) value of 9.67 µg/mL, while the others showed no cytotoxic activities against the four tested cell lines. PMID:22411729

Tian, Junmian; Shen, Yunheng; Li, Huiliang; Liu, Runhui; Shan, Lei; Gao, Jinming; Zhang, Weidong



A new alkaloid from the fruit of Nandina domestica Thunb.  


A new steroidal alkaloid, (20S,22R,24R)-24-ethyl-3-oxocholest-4-en-22-amino, named as nandsterine (1), together with 10 known alkaloids, palmatine (2), O-methylbulbocapnine (3), nantenine (4), dehydronantenine (5), glaucine (6), didehydroglaucine (7), dehydrocorydaline (8), jatrorrhizine (9), magnoflorine (10) and berberine (11), was isolated from the fruit of Nandina domestica Thunb. Their structures were elucidated by using spectroscopic methods as well as by comparing with the published data. Compound 1 was a new class of steroidal alkaloid isolated from the family Berberidaceae, meanwhile compounds 2, 3, 6-8 and 10 were obtained from N. domestica for the first time. Compound 1 exhibited cytotoxicity against HL-60 cells (human leukaemia) with IC50 values of 52.1 ?M. PMID:24897106

Peng, Cai-Ying; Liu, Jian-Qun; Zhang, Rui; Shu, Ji-Cheng



Alkaloid content of the seeds from Erythroxylum Coca var. Coca.  


Alkaloid extracts from the seeds of Erythroxylum Coca var. Coca grown in the Chapare Valley of Bolivia were subjected to gas and liquid chromatographic-mass spectrometric analyses. Several alkaloids from these seeds were detected and characterized, including methylecgonidine, tropine, 3alpha-acetoxytropane, ecgonine methyl ester, cuscohygrine, N-norbenzoyltropine, benzoyltropine, hexanoylecgonine methyl ester, cocaine, cis-cinnamoylcocaine, and trans-cinnamoylcocaine. Methylecgonidine was determined to be the primary constituent and not an analytical artifact. Additionally, two significant new uncharacterized alkaloids were established as present. Recent evidence suggests that some cocaine processors are adding this seed extraction material to cocaine extracted from coca leaf and may impact cocaine impurity signature profiles. PMID:16382835

Casale, John F; Toske, Steven G; Colley, Valerie L



Aza-tryptamine substrates in monoterpene indole alkaloid biosynthesis  

PubMed Central

Biosynthetic pathways can be hijacked to yield novel compounds by introduction of novel starting materials. Here we have altered tryptamine, which serves as the starting substrate for a variety of alkaloid biosynthetic pathways, by replacing the indole with one of four aza-indole isomers. We show that two aza-tryptamine substrates can be successfully incorporated into the products of the monoterpene indole alkaloid pathway in Catharanthus roseus. Use of unnatural heterocycles in precursor directed biosynthesis, in both microbial and plant natural product pathways, has not been widely demonstrated, and successful incorporation of starting substrate analogs containing the aza-indole functionality has not been previously reported. This work serves as a starting point to explore fermentation of aza-alkaloids from other tryptophan and tryptamine derived natural product pathways.

Lee, Hyang-Yeol; Yerkes, Nancy; O'Connor, Sarah E.



Cytotoxic and Anti-HIV Phenanthroindolizidine Alkaloids from Cryptocarya chinensis  

PubMed Central

Bioassay-guided fractionation of the cytotoxic ethanol extract of Cryptocarya chinensis has led to the isolation of 11 compounds, including two phenanthroindolizidine alkaloids [(?)-antofine (1) and dehydroantofine (2)], five pavine alkaloids (3–7), and four proaporphine alkaloids (8–11). The structures of the isolated compounds were determined by means of NMR spectroscopic methods, and supported by HRMS and optical rotation data. Compounds 1 and 2 showed cytotoxic activity against four cancer cell lines, L1210, P388, A549, and HCT-8, with 1 being the most potent against A549 and HCT-8 with EC50 values of 0.002 and 0.001 ?g/mL, respectively. In addition, 2 is first reported to exhibit significant anti-HIV activity.

Wu, Tian-Shung; Su, Chung-Ren; Lee, Kuo-Hsiung



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.

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



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.



Alkaloid-fullerene systems through photocycloaddition reactions.  


The photocycloaddition of tertiary amines to ż60fullerene (C(60)) is an interesting and useful reaction. We wished to extend the applications of this type of reaction through an investigation of the photoaddition of alkaloids to C(60) for the purpose of synthesizing novel and complex photoadducts that are difficult to obtain by usual methods. Irradiation of tazettine (2) or gramine (3) with C(60) in toluene leads to formation of one monoadduct (6 or 7), whereas scandine (1a) or 10-hydroxyscandine (1b) reacts with C(60) photochemically to give two products, the expected ż6,6 monoadduct (5a, 5b) and a new type of monoadduct with a bis-ż6, 6 closed structure (4a, 4b). These new structures were characterized by UV-vis, FT-IR, (1)H NMR, (13)C NMR, (1)H-(1)H COSY, ROESY, HMQC (heteronuclear multiple-quantum coherence), and HMBC (heteronuclear multiple-bond connectivity) spectroscopy. The techniques of time-of-flight secondary ion MS (TOF-SIMS) and field desorption MS (FD-MS) were used for the mass determination. (3)He NMR analysis of the product mixture from photoaddition of 1a to C(60) containing a (3)He atom ((3)He@C(60)) led to two peaks at -9.091 and -11.090 ppm relative to gaseous (3)He, consistent with formation of a ż6, 6-closed monoadduct and a bis-ż6,6 closed adduct. Presumably, the bis-ż6, 6 closed adducts are formed by an intramolecular ż2 + 2 cycloaddition of the vinyl group to the adjacent 6,6-ring junction of C(60) after the initial photocycloaddition. PMID:10864768

Guo, L W; Gao, X; Zhang, D W; Wu, S H; Wu, H M; Li, Y J; Wilson, S R; Richardson, C F; Schuster, D I



New indole N-oxide alkaloids from Evodia fargesii.  


Three new indole N-oxide alkaloids, fargesine (5-hydroxy-12-methyl-10,11,12,13-tetrahydro-1 H-azepino[5,4,3-cd]indole N(12)-oxide, 1), plectocomine 12-methyl-5- O-beta-D-glucopyranoside N(12)-oxide (2), and bufotenine 5-O-beta-D-glucopyranoside N(12)-oxide (3), were isolated from the root and stem of Evodia fargesii Dode along with five known compounds. The structures of the new alkaloids were elucidated on the basis of spectroscopic analysis. PMID:16534733

Qu, Shi-Jin; Liu, Quan-Wen; Tan, Chang-Heng; Jiang, Shan-Hao; Zhu, Da-Yuan



3-Methoxysampangine, a novel antifungal copyrine alkaloid from Cleistopholis patens.  

PubMed Central

Further examination of the active ethanolic extract of the root bark of Cleistopholis patens by using bioassay-directed fractionation resulted in the isolation of a new alkaloid, 3-methoxysampangine (compound I), together with three known alkaloids, eupolauridine (compound II), liriodenine (compound III), and eupolauridine N-oxide (compound IV). The proposed structure of compound I was based on its physicochemical properties and spectral data. 3-Methoxysampangine exhibited significant antifungal activity against Candida albicans, Aspergillus fumigatus, and Cryptococcus neoformans. This is the first report of the isolation of liriodenine (compound III) from the root bark of C. patens.

Liu, S C; Oguntimein, B; Hufford, C D; Clark, A M



Mechanisms of regeneratory effects of baikal aconite diterpene alkaloids.  


Regeneratory activities of Baikal aconite alkaloids were studied on the excision skin wound model. Manifest wound healing effects of songorine, napelline, and hypaconitine were detected. The therapeutic efficiency was based on activation of residual mesenchymal progenitor elements. The development of this phenomenon was explained by the direct effects of alkaloids on precursors and by higher production of growth factors by the skin stromal cells. Songorine exhibited the most pronounced specific activity due to more significant stimulation of progenitor cell differentiation associated with maximum activation of the secretory function of the microenvironment cells. PMID:23113300

Zyuz'kov, G N; Krapivin, A V; Nesterova, Yu V; Povetieva, T N; Zhdanov, V V; Suslov, N I; Fomina, T I; Udut, E V; Miroshnichenko, L A; Simanina, E V; Semenov, A A; Kravtsova, S S; Dygai, A M



Total synthesis of the Securinega alkaloid (-)-secu'amamine A.  


The first enantioselective total synthesis of the rearranged Securinega alkaloid (-)-secu'amamine A is reported starting from D-proline as the source of absolute chirality. The synthesis requires 15 steps starting from D-proline-derived N-trityl aldehyde 11 and proceeds in approximately 9% overall yield. Key steps include a stereoselective conjugate addition of pyrrolidino enedione 19 to afford indolizidine 24 as the major product and cyclization/lactonization of diketoester 25 to produce tetracycle 26. In addition, 1H NMR NOE studies and X-ray analysis on the synthetic alkaloid have established that the indolizidine moiety is trans-fused. PMID:18491903

Liu, Peng; Hong, Sungwoo; Weinreb, Steven M



New 14-Membered Cyclopeptide Alkaloids from Zizyphus oxyphylla Edgew.  


Two new 14-membered cyclopeptide alkaloids, Oxyphylline B (4) and Oxyphylline C (5), along with three known 13-membered cyclopeptide alkaloids, were isolated from stem and roots of Zizyphus oxyphylla Edgew. The compounds were tested for antibacterial activity. Oxyphylline B (4) showed comparatively better antibacterial activities against Escherichia coli (MIC, 5 ?g/mL) than other compounds. This compound also exhibited weak antimicrobial activities against Staphylococcus aureus (MIC, 25 ?g/mL), Pseudomonas aeruginosa (MIC, 50 ?g/mL) and Salmonella typhi (MIC, 50 ?g/mL). PMID:23109868

Kaleem, Waqar Ahmad; Nisar, Muhammad; Qayum, Mughal; Zia-Ul-Haq, Muhammad; Adhikari, Achyut; De Feo, Vincenzo



Glutarimide alkaloids and a terpenoid benzoquinone from Cordia globifera.  


Three new compounds, a meroterpene (2) having a cyclopropane moiety named globiferane and glutarimide alkaloids named cordiarimides A (3) and B (4), were isolated from the roots of Cordia globifera. Compounds 2-4 exhibited weak cytotoxic activity. Cordiarimide B (4) exhibited radical scavenging activity, as it inhibited superoxide anion radical formation in the xanthine/xanthine oxidase (XXO) assay, and also suppressed superoxide anion generation in differentiated HL-60 human promyelocytic leukemia cells when induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). This is the first report on the presence of glutarimide alkaloids in the genus Cordia. PMID:20384317

Parks, Joshua; Gyeltshen, Thinley; Prachyawarakorn, Vilailak; Mahidol, Chulabhorn; Ruchirawat, Somsak; Kittakoop, Prasat



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


Urinary and Biliary Excretion of Ergot Alkaloids from Steers That Grazed Endophyte-Infected Tall Fescue1  

Microsoft Academic Search

Ergot alkaloids cause fescue toxicosis when livestock graze endophyte-infected (E+) tall fescue. Little is known about the bioavailability of the ergot alkaloid classes (lysergic acid, lysergic acid amides, or ergopeptine alkaloids) in livestock, and this hampers development of pharmacological strate- gies to ameliorate the toxicosis. One method used to determine bioavailability of ergot alkaloids is to examine urinary and biliary

J. A. Stuedemann; N. S. Hill; F. N. Thompson; R. A. Fayrer-Hosken; W. P. Hay; D. L. Dawe; D. H. Seman; S. A. Martin



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


An analysis of a commercial sample of Symphyti radix originating from Poland with a total alkaloid content of 0.07% revealed the presence of 7 pyrrolizidine alkaloid-N-oxides: 7-acetyl intermedine, 7-acetyl lycopsamine as the main constituents and lycopsamine, intermedine, symphytine and traces of 2 further not yet identified alkaloids. The percutaneous absorption of these alkaloids was investigated in rats, using a crude alcoholic extract of the plant corresponding to a dose of 194 mg alkaloid-N-oxides/kg b.wt. The excretion of N-oxides in the urine during 2 days was in the range of 0.1-0.4% of the dose. The dermally absorbed N-oxides are not or only to a small extent converted to the free alkaloids in the organism. The oral application led to a 20-50 times higher excretion of N-oxides and free alkaloids in the urine. PMID:7128756

Brauchli, J; Lüthy, J; Zweifel, U; Schlatter, C



Analysis, separation, and bioassay of pyrrolizidine alkaloids from comfrey (Symphytum officinale).  


Pyrrolizidine alkaloids have been linked to liver and lung cancers and a range of other deleterious effects. As with many natural toxicants, major problems arise in determining the effects of the different members of the class and the importance of various forms of ingestion. In this study we have investigated the levels of pyrrolizidine alkaloids in comfrey (Symphytum officinale), determined the levels in different parts of the plant and in herbal remedies, separated the alkaloids into two main groups--the principal parent alkaloids and the corresponding N-oxides--and, finally, carried out a simple bioassay based upon the mutagenic capability of the separated compounds in a human cell line. We conclude that the part of the plant ingested is important in terms of alkaloid challenge and that the effect of two of the major groups of alkaloids individually is different from that of alkaloids in the whole plant extract. PMID:8887946

Couet, C E; Crews, C; Hanley, A B



Pyrroloquinoline and pyridoacridine alkaloids from marine sources.  


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

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



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.

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



Antibacterial cyclopeptide alkaloids from the bark of Condalia buxifolia  

Microsoft Academic Search

The cyclopeptide alkaloid, named condaline-A, was isolated from the root bark of Condalia buxifolia Reissek (Rhamnaceae), along with the known compounds adouetine-Y?, scutianine-B, and scutianine-C. Their structures were determined by spectroscopic analyses, with their antibacterial activities being evaluated by use of a direct bioautography method.

Ademir F Morel; Carla A Araujo; Ubiratan F da Silva; Solange C. S. M Hoelzel; Renato Záchia; Nelci R Bastos



An immunosuppressive tryptophan-derived alkaloid from Lepidagathis cristata  

Microsoft Academic Search

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

V Ravikanth; V. L Niranjan Reddy; P Ramesh; T Prabhakar Rao; P. V Diwan; Ashok Khar; Y Venkateswarlu



Biosynthesis of the defensive alkaloid cicindeloine in Stenus solutus beetles  

NASA Astrophysics Data System (ADS)

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

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



Alkaloid profiling and anticholinesterase activity of South American Lycopodiaceae species.  


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

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



Pyrrolizidine alkaloids, flavonoids and volatile compounds in the genus Eupatorium  

Microsoft Academic Search

Within the scope of a study of antitumour compounds in higher plants a survey is given concerning the presence of pyrrolizidine alkaloids, flavonoids and volatile compounds inEupatorium species. Preliminary results of a phytochemical study of these compounds inE. cannabinum are also presented.

H. Hendriks; Th M. Malingré; E. T. Elema



Cyclopeptide alkaloids from Scutia buxifolia Reiss and their antimicrobial activity  

Microsoft Academic Search

The present study reports a cyclopeptide alkaloid, scutianine M, isolated from the methanolic root bark extract of Scutia buxifolia Reiss (Rhamnaceae) along with six known compounds, scutianines-B, -C, -D, -E, -F, and scutianene D. Its structure was established on the basis of spectroscopic analyses, including application of 2D NMR spectroscopic techniques. As part of a study of the bioactive compounds

Ademir F. Morel; Graciela Maldaner; Vinicius Ilha; Fabiana Missau; Ubiratan F. Silva; Ionara I. Dalcol



Two new C19-diterpenoid alkaloids from Aconitum transsectum.  


Two new C(19)-diterpenoid alkaloids, named aconitramines D (1) and E (2), were isolated from the roots of Aconitum transsectum. Based on comprehensive spectroscopic analyses including IR, ESI-MS, HR-ESI-MS, and 1D and 2D NMR, their structures were elucidated as 18-demethoxyltransconitine A (1) and 8-O-anisoyl-14-hydroxylacoforesticine (2). PMID:22251154

Shen, Yong; Ai, Hong-Lian; Zi, Shu-Hui; Wang, Jian-Jun; Zhang, Xue-Mei; Chen, Ji-Jun



Mechanisms of hemostimulating effect of Aconitum baicalense diterpene alkaloids.  


A mixture of diterpene alkaloids of Aconitum baicalense exhibited pronounced regenerative hemostimulating properties on the model of cytostatic myelosuppression. The therapeutic effect is based on activation of hemopoietic progenitor cells against the background of increased feeder capacity of stromal compartment of the hemopoiesis-inducing microenvironment and decreased count of mesenchymal stem cells in the bone marrow. PMID:24137601

Zyuz'kov, G N; Zhdanov, V V; Miroshnichenko, L A; Udut, E V; Simanina, E V; Stavrova, L A; Agafonov, V I; Chaikovskiy, A V; Minakova, M Yu; Povet'eva, T N; Suslov, N I; Krapivin, A V; Nesterova, Yu V; Semenov, A A; Reykhart, D V; Dygai, A M




Microsoft Academic Search

Loline alkaloids (LA) are secondary metabolites produced by Epichloandamp;euml; (anamorph, Neotyphodium) grass endophytes. They are toxic and deterrent to a broad range of herbivorous insects but not to livestock. This protective bioactivity has spurred considerable research into the LA biosynthetic pathway. LOL, the gene cluster containing nine genes, is required for LA biosynthesis. The regulation of LOL genes during LA




Hypoglycemic activity of alkaloidal fraction of Tinospora cordifolia.  


The stem of Tinospora cordifolia (TC) is widely used in the therapy of diabetes in traditional folk medicine of India. In the present study, isoquinoline alkaloid rich fraction (AFTC) derived from stem of TC and three alkaloids viz., palmatine, jatrorrhizine and magnoflorine were evaluated for insulin-mimicking and insulin-releasing effect in vitro and in vivo. Their effect on hepatic gluconeogenesis was examined in rat hepatocytes. Insulin releasing effect was detected in vitro using rat pancreatic ?-cell line, RINm5F. Furthermore, effects of AFTC and isolated alkaloids on serum glucose and insulin level were studied in fasted and glucose challenged normal rats. AFTC significantly decreased gluconeogenesis in rat hepatocytes as insulin did and it increases insulin secretion in RINm5F cells similar to tolbutamide. In acute 30 min test in vitro, AFTC, palmatine, jatrorrhizine and magnoflorine stimulated insulin secretion from the RINm5F cell line. As in vivo results, administration of AFTC (50, 100, and 200 mg/kg), palmatine, jatrorrhizine and magnoflorine (10, 20 and 40 mg/kg each) orally significantly decreased fasting serum glucose, and suppressed the increase of blood glucose levels after 2 g/kg glucose loading in normal rats. In vivo study further justified their insulin secreting potential by raising the serum insulin level in glucose fed rats. These results demonstrate the alkaloid present in TC contributed for antihyperglycemic activity. AFTC may have hypoglycemic effects via mechanisms of insulin releasing and insulin-mimicking activity and thus improves postprandial hyperglycemia. PMID:21665451

Patel, Mayurkumar B; Mishra, Shrihari



The impact of structural biology on alkaloid biosynthesis research.  


In the recent past, macromolecular crystallography has gone through substantial methodological and technological development. The purpose of this review is to provide a general overview of structural biology and its impact on enzyme structure/function analysis and illustrate how it is modifying the focus of research relevant to alkaloid biosynthesis. PMID:22907740

Panjikar, Santosh; Stoeckigt, Joachim; O'Connor, Sarah; Warzecha, Heribert



Novel triterpenoid acyl esters and alkaloids from Anoectochilus roxburghii.  


Two novel sorghumol acyl esters, sorghumol 3-O-Z-p-coumarate and sorghumol 3-O-E-p-coumarate, and a novel alkaloid, anoectochine, were isolated from the whole plants of Anoectochilus roxburghii along with one known triterpenoid, sorghumol. Their structures were established by their detailed spectral studies, including two-dimensional NMR ((1)H-(1)H COSY, HSQC and HMBC). PMID:18435530

Han, Mei-Hua; Yang, Xiu-Wei; Jin, Yan-Ping



Monoterpenoid indole alkaloids from the bark of Alstonia scholaris.  


Six new monoterpenoid indole alkaloids, scholarisines B-G (1- 6), together with 15 known analogues (7- 21), were isolated from the bark of Alstonia scholaris. Their structures were determined by 1D and 2D NMR spectra and MS analyses. The structure of 1 was further supported by the single-crystal X-ray. PMID:19609839

Feng, Tao; Cai, Xiang-Hai; Zhao, Pei-Ji; Du, Zhi-Zhi; Li, Wei-Qi; Luo, Xiao-Dong



Indole alkaloid production by hairy root cultures of Catharanthus roseus  

Microsoft Academic Search

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

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



Sagitol, a pyridoacridine alkaloid from the sponge Oceanapia sagittaria  

Microsoft Academic Search

The sponge Oceanapia sagittaria from Palau contained the known sponge metabolite dercitamide (1) and a new pyridoacridine alkaloid sagitol (2). The structure of sagitol (2) was determined by interpretation of spectral data and confirmed by oxidation of dercitamide (1). CD measurements suggest that sagitol (2) is not an artifact.

Christine E. Salomon; D. John Faulkner



Total synthesis of the marine pyridoacridine alkaloid sebastianine A  

Microsoft Academic Search

The synthesis of the marine alkaloid sebastianine A and of a regioisomer has been accomplished via hetero-Diels–Alder reaction of indole-4,7-dione or N-tosylindole-4,7-dione with trifluoroacetamidocinnamaldehyde dimethylhydrazone, and subsequent cyclisation in alkaline conditions.

Laurent Legentil; Jean Bastide; Evelyne Delfourne



Qualitative variation of alkaloids in color morphs of Cystodytes (Ascidiacea)  

Microsoft Academic Search

Despite their great variability, particularly of color, Mediterranean specimens of the genus Cystodytes are usually attributed to the cosmopolitan species Cystodytes dellechiajei. In this study, we used MALDI-TOF and HPLC techniques to assess alkaloid distribution in the four most abundant color morphs of Cystodytes in the western Mediterranean (green, purple, brown and blue). The intraspecimen location of these compounds (either

Susanna López-Legentil; Ralf Dieckmann; Nataly Bontemps-Subielos; Xavier Turon; Bernard Banaigs



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


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

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



Antiplasmodial alkaloids from the stem bark of Strychnos malacoclados.  


From the stem bark of Strychnos malacoclados, one new bisindole alkaloid, 3-hydroxylongicaudatine Y (1), was isolated along with the known alkaloids vomicine (2), bisnordihydrotoxiferine (3), divarine (4), longicaudatine (5), longicaudatine Y (6), and longicaudatine F (7). All the compounds were tested for their antimalarial activity against the chloroquine-sensitive 3D7 and -resistant W2 strains of Plasmodium falciparum. Longicaudatine was the most active compound with IC?? values of 0.682 and 0.573 µM, respectively. The activity of compounds 1, 3, 4, 6, and 7 against the two strains ranged from 1.191 to 6.220 µM and 0.573 to 21.848 µM, respectively. Vomicine (2), the only monomer isolated, was inactive. The alkaloids of the longicaudatine-type ( 1, 5-7) were more active than those of the caracurine-type (3- 4). The presence of the ether bridge in the molecule seems to increase the antiplasmodial activity. Compounds 1, 5, and 7 were tested against the WI-38 human fibroblast cell line. Longicaudatine was the most cytotoxic compound with an IC?? of 2.721 µM. Longicaudatine F was 40-46 times more active against the two strains of P. falciparum than against the human fibroblasts and was thus considered as the more selective alkaloid. The structures of the compounds were determined based on the analysis of their spectral data. PMID:22193980

Tchinda, Alembert T; Ngono, Annie R N; Tamze, Victorine; Jonville, Marie-Caroline; Cao, Martine; Angenot, Luc; Frédérich, Michel



Daphmacromines K-O, alkaloids from Daphniphyllum macropodum.  


Five new yuzurimine-type Daphniphyllum alkaloids, daphmacromines K-O (1-5), were isolated from the leaves and stems of Daphniphyllum macropodum. Their structures were elucidated by extensive spectroscopic techniques, including 2D NMR spectroscopy and mass spectrometry. Daphmacromine O (5) showed moderate cytotoxic activity against brine shrimp. PMID:23756191

Cao, Ming-Ming; Wang, Lei; Zhang, Yu; He, Hong-Ping; Gu, Yu-Cheng; Zhang, Qiang; Li, Yan; Yuan, Chun-Mao; Li, Shun-Lin; Di, Ying-Tong; Hao, Xiao-Jiang



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


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



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


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

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



Diterpenoid alkaloids from the Chinese traditional herbal "Fuzi" and their cytotoxic activity.  


Ten diterpenoid alkaloids, including eight aconitine-type C??-diterpenoid alkaloids and two hetisine-type C??-diterpenoid alkaloids, were isolated from the secondary roots of Aconitum carmichaeli Debx., known as "Fuzi" in Chinese traditional herbal medicine. Their structures were established on the basis of their spectroscopic data and comparison with those of the literature. Among these alkaloids, chasmanine, oxonitine and 15-acetylsongoramine were isolated for the first time from this medicinal plant. The cytotoxic activity of the alkaloids were tested against several cell lines by the MTT method in which aconitine, hypaconitine, mesaconitne and oxonitine were found to strongly inhibit the growth of the HePG2 cell line, which showed that the existence and quantity of the ester groups have a significant influence on the cytotoxicity of the diterpenoid alkaloids. PMID:22628040

Gao, Feng; Li, Yuan-Yuan; Wang, Dan; Huang, Xing; Liu, Qian



Java Numerics  

NSDL National Science Digital Library

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


NMR determination of pKa values of indoloquinoline alkaloids.  


Malaria is one of the most serious global health problems. Isolating new therapeutic agents with potential antimalarial activity from natural sources or preparing such agents either semisynthetically or synthetically is one strategy for solving the problem of resistance constantly evolving to the drugs currently in use. For alkaloids, the acid-base dissociation constant, pK(a), is an important characteristic, thought to be associated with biological activity. In this contribution, pK(a) values for several indoloquinoline alkaloids were determined by using (1)H NMR spectroscopy in a mixture of solvents. The data were recalculated for water solutions using the correction factors reported previously. The structural dependence of the pK(a) values for cryptolepine and its isomers neocryptolepine, isocryptolepine and isoneocryptolepine as well as some substituted neocryptolepine derivatives is discussed. PMID:19653253

Grycová, Lenka; Dommisse, Roger; Pieters, Luc; Marek, Radek



[Extraction of pharmacologically active alkaloids from Vinca species].  


From the Genius Vinca the drugs have been received, arbitrally named: Vingerbin- with anthyarithmic activity, Vincabral-for improvement of brain blood circulation and leicobetin-as stimulator of leicopoesis. The investigations has been performed for creation of rational, resource saving, rentable phyto technologies. As a result, the liquid extraction general schema is provided for receipt of indolic alkaloids from plants V. herbaceae and V.minor. Analyses have shown that extraction with diluent gaz gives the possibility to receive the sums rich with alkaloids:Vingerbin and Vincabral. The advantage of extraction with diluent gaz is exclusion of high volumes of organic and non organic chemicals on the stage of extraction from raw material and liquid extraction, and remain and lipofil fraction converse to new phytosubtances for receipt of biologically active flavonoids, amino acids etc. PMID:21778554

Gagua, N D; Bakuridze, A D; Vachnadze, N S; Berashvili, D T; Vachnadze, V Iu



Suppression of ochratoxin biosynthesis by naturally occurring alkaloids.  


The effects of four alkaloids on the biosynthesis of ochratoxin A (OTA), ochratoxin B (OTB) and citrinin were examined on four OTA-producing aspergilli: Aspergillus auricomus, A. sclerotiorum and two isolates of A. alliaceus. Piperine and piperlongumine, natural alkaloids of Piper longum, significantly inhibited OTA production at 0.001% (w/v) for all aspergilli examined. Piperine and piperlongumine affected the polyketide synthesis step of OTA production and inhibited production of citrinin. Curcumin, a constituent of tumeric, completely inhibited mycelial growth of A. alliaceus isolate 791 at 0.1% (w/v) and decreased OTA production by approximately 70% at 0.01% (w/v). Sesamin, a constituent of sesame oil, inhibited OTA and OTB production by 60 and 45%, respectively, at 0.1% (w/v), showing its effect was on chloroperoxidase and polyketide synthase activity. The potential advantage of these natural products to reduce ochratoxin contamination of agricultural commodities is discussed. PMID:17454112

Lee, S E; Park, B S; Bayman, P; Baker, J L; Choi, W S; Campbell, B C



Antileishmanial Activity of an Indole Alkaloid from Peschiera australis  

PubMed Central

In this study, we show the leishmanicidal effects of a chloroform fraction (CLF) and a purified indole alkaloid obtained from crude stem extract of Peschiera australis against Leishmania amazonensis, a causative agent of cutaneous leishmaniasis in the New World. In a bioassay-guided chemical fractionation, the leishmanicidal activity in CLF completely and irreversibly inhibited promastigote growth. This fraction was also active against amastigotes in infected murine macrophages. Chemical analysis of CLF identified an iboga-type indole alkaloid coronaridine as one of its major compounds. Coronaridine showed potent antileishmanial activity, inhibiting promastigote and amastigote growth. Promastigotes and amastigotes treated with CLF or coronaridine showed pronounced alterations in their mitochondria as assessed by transmission electron microscopy.

Delorenzi, Jan Carlo; Attias, Marcia; Gattass, Cerli R.; Andrade, Marcelo; Rezende, Claudia; da Cunha Pinto, Angelo; Henriques, Amelia T.; Bou-Habib, Dumith C.; Saraiva, Elvira M. B.



Antiparasitic activity of marine pyridoacridone alkaloids related to the ascididemins.  


A series of pyridoacridone alkaloids, including the marine alkaloid ascididemin were tested in vitro for antiparasitic activity against P. falciparum (K1, NF54), L. donovani, T. cruzi, T. b. rhodesiense and two mammalian cell lines (L6, RAW 264.7). Most compounds showed high antiplasmodial activity, moderate antileishmanial activity against both extra- and intracellular forms, and significant trypanocidal effects against T. cruzi and T. b. brucei. However, when tested against mammalian cell lines, most of the compounds were also toxic for macrophage-like RAW 264.7 cells and skeletal muscle myoblast L6 cells. Correlations between molecular structures and antiparasitic activity are discussed in detail. Specific compounds are illustrated with emphasis on their potential as new antiparasitic drug leads. PMID:12865971

Copp, Brent R; Kayser, Oliver; Brun, Reto; Kiderlen, Albrecht F



New diterpenoid alkaloids from Aconitum heterophyllum Wall: Selective butyrylcholinestrase inhibitors.  


Two new diterpenoid alkaloids, heterophyllinine-A (1) and heterophyllinine-B (2), along with two known alkaloids dihydroatisine (3) and lycoctonine (4) were isolated from the roots of Aconitum heterophyllum Wall. The structure of (1) and (2), were deduced on the basis of spectral data. Compounds 1-2 inhibited acetylcholinesterase (AChE, EC and butyrylcholinesterase (BChE, EC enzymes in a concentration-dependent manner with percent inhibition ranging between 4.24% and 6.94 % and 79.1 % and 82.75 % for AChE and BChE, respectively indicating that compounds 1 and 2 are about thirteen times more specific to BChE than AChE. PMID:18615279

Nisar, Muhammad; Ahmad, Manzoor; Wadood, Noreen; Lodhi, Muhammad Arif; Shaheen, Farzana; Choudhary, M Iqbal



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.

Wink, Michael; Hartmann, Thomas



Tropane alkaloids in auxin-independent root cultures of Physochlaina physaloides.  


Adventitious and hairy root cultures of Physochlaina physaloides were established. These roots grew well and produced high amounts of tropane alkaloids (particularly hyoscyamine and 6 beta-hydroxyhyoscyamine) in auxin-free culture medium. The effects of basal media and temperature on the growth and alkaloid production of these roots were investigated. Both root cultures produced highest amount of tropane alkaloids in B5 medium though the optimum temperature for hairy roots were lower than that for adventitious roots. PMID:12638187

Shimomura, Koichiro; Hirose, Makoto; Natori, Shinsaku; Satake, Motoyoshi; Yoshimatsu, Kayo; Ishimaru, Kanji



Effect of Tween 80 on alkaloid-producing cultures of Claviceps paspali  

Microsoft Academic Search

Addition of Tween 80 to submerged cultures ofClaviceps paspali (Stevens and Hall) growing in a simple defined medium increased biomass formation and caused a temporary change in alkaloid\\u000a synthesis intensity. The Tween-supplemented culture reached maximal alkaloid yields four days earlier than the control. The\\u000a shift of alkaloid production was associated with a shift of organic acids and amino acids in

Z. ?ehá?ek



Effect of Agrobacterium rhizogenes T-DNA on alkaloid production in Solanaceae plants  

Microsoft Academic Search

Inoculation of leaf sections of tobacco, Duboisia hybrid and Datura metel Solanaceae plants with A4 strain of Agrobacterium rhizogenes, induced transformed roots with the capacity to produce putrescine-derived alkaloids. In general, the hairy roots obtained showed two morphologies: typical hairy roots with high capacity to produce alkaloids and callus-like roots with faster growth capacity and lower alkaloid production. The aux1

E. Moyano; S. Fornalé; J. Palazón; R. M. Cusidó; M. Bonfill; C. Morales; M. T. Pińol



Total synthesis of securinega alkaloids (-)-norsecurinine, (-)-niruroidine and (-)-flueggine A.  


A consecutive synthetic strategy was developed toward the total synthesis of securinega alkaloids. (-)-Norsecurinine was concisely assembled by addition of a methoxyallene to a ketone for efficient side-chain installation. Ring-closing metathesis was also utilized as a key step. The first total synthesis of (-)-niruroidine was achieved from (-)-norsecurinine in three steps, while the route to (-)-flueggine A featured a 1,3-dipolar cycloaddition to forge the core structure. PMID:25000877

Ma, Nan; Yao, Yiwu; Zhao, Bing-Xin; Wang, Ying; Ye, Wen-Cai; Jiang, Sheng



Amaryllidaceae Isocarbostyril Alkaloids and Their Derivatives as Promising Antitumor Agents  

PubMed Central

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

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



Cynthichlorine: a bioactive alkaloid from the tunicate Cynthia savignyi.  


From ether extracts of the tunicate Cynthia savignyi, collected in Morocco, a new alkaloid-cynthichlorine-has been isolated. The structure of cynthichlorine has been characterized by extensive 2D-NMR data. Cynthichlorine possesses antifungal activity against two tomato pathogenic fungi: Botrytis cinerea and Verticillium albo atrum and antibacterial activity against Agrobacterium radiobacter, Escherichia coli and Pseudomonas aeruginosa and cytotoxicity against Artemia salina larvae. PMID:14630251

Abourriche, A; Abboud, Y; Maoufoud, S; Mohou, H; Seffaj, T; Charrouf, M; Chaib, N; Bennamara, A; Bontemps, N; Francisco, C



Alistonitrine A, a caged monoterpene indole alkaloid from Alstonia scholaris.  


Alistonitrine A, a new monoterpene indole alkaloid incorporating a third nitrogen atom, was isolated from the leaves of Alstonia scholaris and found to possess an unprecedented caged skeleton with a unique 6/5/6/5/5/6 ring system. Its structure and absolute configuration were established by extensive spectroscopic analyses and electron circular dichroism calculations. A plausible biogenetic pathway has been proposed for the biosynthesis of alistonitrine A from picrinine. PMID:24491148

Zhu, Guo-Yuan; Yao, Xiao-Jun; Liu, Liang; Bai, Li-Ping; Jiang, Zhi-Hong



Zoaramine, a Zoanthamine-like Alkaloid with a New Skeleton.  


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



Lodopyridone, a Structurally Unprecedented Alkaloid from a Marine Actinomycete  

PubMed Central

Chemical examination of the secondary metabolites of a marine Saccharomonospora sp., isolated from marine sediments collected at the mouth of the La Jolla Submarine Canyon, yielded the unprecedented alkaloid lodopyridone (1). The low proton-to-carbon ratio of 1 precluded structure elucidation by NMR spectroscopic methods, thus the structure was defined by X-ray crystallography. Lodopyridone is cytotoxic to HCT-116 human colon cancer cells with IC50 = 3.6 ?M.

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



Beta-carboline alkaloids derived from the ascidian Synoicum sp.  


Six ?-carboline alkaloids (1-6) of the eudistomin Y class were isolated from the Korean ascidian Synoicum sp. These compounds were chemically converted to a known compound, eudistomin Y(1) (7) and six new derivatives, designated eudistomins Y(8)-Y(13) (8-13). Several of these natural and synthetic compounds exhibited moderate to significant antimicrobial activity, weak cytotoxic activity, and inhibitory activities toward sortase A, isocitrate lyase, and Na(+)/K(+)-ATPase. Structure-activity relationships were also deduced. PMID:22652254

Won, Tae Hyung; Jeon, Ju-Eun; Lee, So-Hyoung; Rho, Boon Jo; Oh, Ki-Bong; Shin, Jongheon



Photoassisted Synthesis of Enantiopure Alkaloid Mimics Possessing Unprecedented Polyheterocyclic Cores  

PubMed Central

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

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



Direct Methoxypyridine Functionalization Approach to Magellanine-Type Lycopodium Alkaloids  

PubMed Central

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

Murphy, Rebecca A.; Sarpong, Richmond



Interrupted Fischer Indolization Approach toward the Communesin Alkaloids and Perophoramidine  

PubMed Central

A concise approach toward the total synthesis of the communesin alkaloids and perophoramidine is reported. The strategy relies on the use of the interrupted Fischer indolization to build the tetracyclic indoline core of the natural products. Studies to probe the scope and limitations of this plan are presented. Although the methodology does not tolerate a C8-allyl substituent en route to the challenging vicinal quaternary stereocenters, variation at C7 and on the C ring is permitted.

Schammel, Alex W.; Chiou, Grace; Garg, Neil K.



Antileishmanial activity of indole alkaloids from Aspidosperma ramiflorum  

Microsoft Academic Search

The present study was designated to evaluate the antileishmanial activity of acid and basic fractions that were obtained after acid-basic extraction, from ethanolic 70% crude extract and pure compounds from the stem bark of Aspidosperma ramiflorum. The basic alkaloidal fraction presented a good activity against the extracellular form (promastigotes) of Leishmania (L.) amazonensis (LD50 value<47?g\\/ml). Based on these findings, the

J. C. A. Tanaka; C. C. da Silva; I. C. P. Ferreira; G. M. C. Machado; L. L. Leon; A. J. B. de Oliveira



Update on analytical methods for toxic pyrrolizidine alkaloids  

Microsoft Academic Search

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

Colin Crews; Franz Berthiller; Rudi Krska



Antitrypanosomal pyridoacridine alkaloids from the Australian ascidian Polysyncraton echinatum  

Microsoft Academic Search

Bioassay-guided fractionation of the crude CH2Cl2\\/MeOH extract from the Australian ascidian Polysyncraton echinatum led to the isolation of a new pyridoacridine alkaloid, 12-deoxyascididemin (1), along with two known analogues, ascididemin (2) and eilatin (3). The structure of 1 was determined following extensive analysis of 1D\\/2D NMR and MS data. Biological evaluation showed that compounds 1–3 are potent antitrypanosomal agents with

Yunjiang Feng; Rohan A. Davis; Melissa L. Sykes; Vicky M. Avery; Anthony R. Carroll; David Camp; Ronald J. Quinn



A Torquoselective 6? Electrocyclization Approach to Reserpine Alkaloids  

PubMed Central

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

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



A torquoselective 6? electrocyclization approach to reserpine alkaloids.  


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

Barcan, Gregg A; Patel, Ashay; Houk, K N; Kwon, Ohyun



Aristolactam-Type Alkaloids from Orophea enterocarpa and Their Cytotoxicities  

PubMed Central

A new aristolactam, named enterocarpam-III (10-amino-2,3,4,6-tetramethoxy phenanthrene-1-carboxylic acid lactam, 1) together with the known alkaloid stigmalactam (2), were isolated from Orophea enterocarpa. Their structures were elucidated on the basis of interpretation of their spectroscopic data. Compounds 1 and 2 exhibited significant cytotoxicities against human colon adenocarcinoma (HCT15) cell line with IC50 values of 1.68 and 1.32 ?M, respectively.

Nayyatip, Sanchai; Thaichana, Pak; Buayairaksa, Mongkol; Tuntiwechapikul, Wirote; Meepowpan, Puttinan; Nuntasaen, Narong; Pompimon, Wilart



Antimalarial diterpene alkaloids from the seeds of Caesalpinia minax.  


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

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



Isoquinoline alkaloids from Tinospora cordifolia inhibit rat lens aldose reductase.  


The inhibitory activity of Tinospora cordifolia stem-derived alkaloids was evaluated against lens aldose reductase (AR) isolated from male Wistar rats. Anticataract potential of the alkaloids of T. cordifolia was evaluated in vitro in rat lenses, considering the activity of normal rat lenses as 100%. The biologically active constituents of T. cordifolia extract were characterized as the isoquinoline alkaloids, jatrorrhizine, palmatine and magnoflorine, by spectral analysis. The inhibitory effects varied with all chemicals and concentrations used. The inhibitory concentration (IC??) values of jatrorrhizine, palmatine and magnoflorine are 3.23, 3.45 and 1.25?µg/mL respectively. The concentration of maximum activity was selected for its effect on galactose-induced polyol accumulation in vitro. The percentage inhibition of galactose-induced polyol accumulation was 62.6, 58.8 and 27.7% in the presence of jatrorrhizine, palmatine and magnoflorine, respectively. Magnoflorine may be useful as lead compounds and new agents for AR inhibition. PMID:22294283

Patel, Mayurkumar B; Mishra, Shrihari



The Alkaloid Alstonine: A Review of Its Pharmacological Properties  

PubMed Central

Indole compounds, related to the metabolism of tryptophan, constitute an extensive family, and are found in bacteria, plants and animals. Indolic compounds possess significant and complex physiological roles, and especially indole alkaloids have historically constituted a class of major importance in the development of new plant derived drugs. The indole alkaloid alstonine has been identified as the major component of a plant-based remedy, used in Nigeria to treat mental illnesses by traditional psychiatrists. Although it is certainly difficult to compare the very concept of mental disorders in different cultures, the traditional use of alstonine is remarkably compatible with its profile in experimental animals. Even though alstonine in mice models shows a psychopharmacological profile closer to the newer atypical antipsychotic agents, it also shows important differences and what seems to be an exclusive mechanism of action, not entirely clarified at this point. Considering the seemingly unique mode of action of alstonine and that its traditional use can be viewed as indicative of bioavailability and safety, this review focuses on the effects of alstonine in the central nervous system, particularly on its unique profile as an antipsychotic agent. We suggest that a thorough understanding of traditional medical concepts of health and disease in general and traditional medical practices in particular, can lead to true innovation in paradigms of drug action and development. Overall, the study of this unique indole alkaloid may be considered as another example of the richness of medicinal plants and traditional medical systems in the discovery of new prototypic drugs.

Elisabetsky, E.; Costa-Campos, L.



Absence of alkaloids in Psychotria carthagenensis Jacq. (Rubiaceae).  


Psychotria viridis and P. carthagenensis are often discussed in relation to the hallucinogenic beverage Ayahuasca, used for religious, medicinal and social purposes. The significance of including Psychotria species in this beverage has been understood on the basis of substantial amounts of tryptamine alkaloids detected on leaves of both P. viridis and P. carthagenensis. Nevertheless, there is a long lasting debate over the identification of which Psychotria species are actually traditionally employed. We here report that a P. carthagenensis leaf ethanol extract was found to be devoid of alkaloids. The extract significantly decreased mice body temperature (350 and 500 mg/kg). Toxicity assessment revealed that the extract induced sedation and slight ptoses (75% of animals treated with 1000 mg/kg). Lethality was not observed within 48 h. The data indicate that P. carthagenensis does have bioactive compound(s), possibly active at the central nervous system, but unlikely to be tryptamine alkaloids as in the case of P. viridis. Therefore, if P. carthagenensis is indeed used by ayahuasqueros, its chemical and pharmacological significance have yet to be elucidated. PMID:8941866

Leal, M B; Elisabetsky, E



Effects of alkaloidal extract of Phyllanthus niruri on HIV replication.  


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

Naik, A D; Juvekar, A R



Activities of naphthylisoquinoline alkaloids and synthetic analogs against Leishmania major.  


The current treatments for leishmaniasis are unsatisfactory due to their toxic side effects, high costs, and increasing problems with drug resistance. Thus, there is an urgent need for alternative drugs against leishmaniasis. Different approaches have been used to identify novel pharmacophores against Leishmania sp. parasites, and one strategy has been the analysis of naturally occurring plant-derived compounds, including naphthylisoquinoline alkaloids. In the present study, we examined the abilities of these alkaloids to inhibit the growth of Leishmania major promastigotes and evaluated their effects on macrophages, dendritic cells, and fibroblasts. Furthermore, we determined the efficacy of selected compounds in decreasing the infection rate of macrophages and regulating their production of cytokines and nitric oxide. Our results demonstrate that the naphthylisoquinoline alkaloids ancistrocladiniums A and B (compounds 10 and 11) and the synthetic isoquinolinium salt (compound 14) were effective against intracellular amastigotes in the low submicromolar range, while toxicity against mammalian cells was observed at concentrations that were significantly higher than those needed to impair parasite replication. The activities of compounds 11 and 14 were mainly directed against the amastigote stage of L. major. This effect was not associated with the stimulation of host macrophages to produce nitric oxide or secrete cytokines relevant for the leishmanicidal function. In conclusion, our data suggest that ancistrocladiniums A and B (compounds 10 and 11) and the synthetically prepared isoquinolinium salt (compound 14) are promising candidates to be considered as lead compounds for leishmanicidal drugs. PMID:17088484

Ponte-Sucre, Alicia; Faber, Johan H; Gulder, Tanja; Kajahn, Inga; Pedersen, Sarah E H; Schultheis, Martina; Bringmann, Gerhard; Moll, Heidrun



Activities of Naphthylisoquinoline Alkaloids and Synthetic Analogs against Leishmania major?  

PubMed Central

The current treatments for leishmaniasis are unsatisfactory due to their toxic side effects, high costs, and increasing problems with drug resistance. Thus, there is an urgent need for alternative drugs against leishmaniasis. Different approaches have been used to identify novel pharmacophores against Leishmania sp. parasites, and one strategy has been the analysis of naturally occurring plant-derived compounds, including naphthylisoquinoline alkaloids. In the present study, we examined the abilities of these alkaloids to inhibit the growth of Leishmania major promastigotes and evaluated their effects on macrophages, dendritic cells, and fibroblasts. Furthermore, we determined the efficacy of selected compounds in decreasing the infection rate of macrophages and regulating their production of cytokines and nitric oxide. Our results demonstrate that the naphthylisoquinoline alkaloids ancistrocladiniums A and B (compounds 10 and 11) and the synthetic isoquinolinium salt (compound 14) were effective against intracellular amastigotes in the low submicromolar range, while toxicity against mammalian cells was observed at concentrations that were significantly higher than those needed to impair parasite replication. The activities of compounds 11 and 14 were mainly directed against the amastigote stage of L. major. This effect was not associated with the stimulation of host macrophages to produce nitric oxide or secrete cytokines relevant for the leishmanicidal function. In conclusion, our data suggest that ancistrocladiniums A and B (compounds 10 and 11) and the synthetically prepared isoquinolinium salt (compound 14) are promising candidates to be considered as lead compounds for leishmanicidal drugs.

Ponte-Sucre, Alicia; Faber, Johan H.; Gulder, Tanja; Kajahn, Inga; Pedersen, Sarah E. H.; Schultheis, Martina; Bringmann, Gerhard; Moll, Heidrun



Quassidines A-D, bis-beta-carboline alkaloids from the stems of Picrasma quassioides.  


Four new bis-beta-carboline alkaloids, quassidines A-D (1-4), together with a known alkaloid, picrasidine C (5), were isolated from the stems of Picrasma quassioides. Quassidine A (1) is the first reported bis-beta-carboline alkaloid possessing a novel cyclobutane moiety. The structures of the new compounds were determined on the basis of their 1D and 2D NMR and X-ray diffraction data. A possible biogenetic pathway for these alkaloids was proposed, and all compounds were evaluated for anti-inflammatory activity. Only quassidine A (1) showed weak activity. PMID:20095629

Jiao, Wei-Hua; Gao, Hao; Li, Chen-Yang; Zhao, Feng; Jiang, Ren-Wang; Wang, Ying; Zhou, Guang-Xiong; Yao, Xin-Sheng



Alkaloid spectrum in diploid and tetraploid hairy root cultures of Datura stramonium.  


Hairy root cultures were obtained from diploid and induced tetraploid plants of Datura stramonium and analyzed by gas chromatography/mass spectrometry. Twenty alkaloids (19 for diploid and 9 for tetraploid hairy root cultures) were identified. A new tropane ester 3-tigloyloxy-6-propionyloxy-7-hydroxytropane was identified on the basis of mass spectral data. Hyoscyamine was the main alkaloid in both diploid and tetraploid cultures. In contrast to diploid hairy roots, the percentage contributions of the alkaloids, with exceptions for hyoscyamine and apoatropine, were higher in the total alkaloid mixture of tetraploid hairy roots. PMID:12622224

Berkov, Strahil; Pavlov, Atanas; Kovatcheva, Petia; Stanimirova, Pepa; Philipov, Stefan



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


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



[Studies on the effect of an alkaloid extract of Symphytum officinale on human lymphocyte cultures].  


An alkaloid extract of Symphytum officinale was investigated for its chromosome-damaging effect in human lymphocytes in vitro. In concentrations of 1.4 micrograms/ml and 14 micrograms/ml the alkaloids had no effect, in concentrations of 140 micrograms/ml and 1400 micrograms/ml the alkaloids induced sister chromatid exchanges (SCE) as well as chromosome aberrations. Additionally, the influence of rat liver enzymes (S9) was tested. The SCE-inducing capacity and the clastogenic effect of Symphytum alkaloids was increased by simultaneous application of S9-Mix. PMID:2616671

Behninger, C; Abel, G; Röder, E; Neuberger, V; Göggelmann, W



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



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

PubMed Central

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

Conner, William E.; Boada, Ruth; Schroeder, Frank C.; Gonzalez, Andres; Meinwald, Jerrold; Eisner, Thomas



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


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

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



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


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

Conner, W E; Boada, R; Schroeder, F C; González, A; Meinwald, J; Eisner, T



Two new amide alkaloids from the flower of Datura metel L  

Microsoft Academic Search

Two new amide alkaloids were isolated from the alkaloidal fraction of Datura metel L. Their structures were elucidated as (E)-methyl 4-(3-(4-hydroxyphenyl)-N-methylacrylamido) butanoate and 6,7-dimethyl-1-D-ribityl-quinoxaline-2,3(1H,4H)-dione-5?-O-?-D-glucopyranoside on the basis of spectroscopic methods including HRESIMS, 1D and 2D NMR. Tropane alkaloids have for a long time been considered as characteristic ingredients of D. metel. However, the presence of amide alkaloids in D. metel

Bing-You Yang; Yong-Gang Xia; Qiu-Hong Wang; De-Qiang Dou; Hai-Xue Kuang



Two new amide alkaloids from the flower of Datura metel L.  


Two new amide alkaloids were isolated from the alkaloidal fraction of Datura metel L. Their structures were elucidated as (E)-methyl 4-(3-(4-hydroxyphenyl)-N-methylacrylamido) butanoate and 6,7-dimethyl-1-D-ribityl-quinoxaline-2,3(1H,4H)-dione-5'-O-?-D-glucopyranoside on the basis of spectroscopic methods including HRESIMS, 1D and 2D NMR. Tropane alkaloids have for a long time been considered as characteristic ingredients of D. metel. However, the presence of amide alkaloids in D. metel was reported for the first time in this study. PMID:20600686

Yang, Bing-You; Xia, Yong-Gang; Wang, Qiu-Hong; Dou, De-Qiang; Kuang, Hai-Xue



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


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 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



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



Polycyclic aromatic alkaloids. XII: In vitro- and in vivo-investigations of the cytotoxic marine alkaloid 2-bromoleptoclinidinone.  


Aminoquinone 2a, the tetracyclic quinone 3b, and the pentacyclic alkaloid 2-bromoleptoclinidinone (4a) were submitted to the NCl standard in vitro assay using 60 tumor cell lines. Compound 4a showed very high in vitro cytotoxicity and was therefore selected for further evaluation. In the in vivo screening 4a was tested at maximally tolerated doses in four models, but no significant antitumor activity could be found. PMID:9035236

Bracher, F



Alkaloid production in Catharanthus roseus (L.) G. Don cell cultures. XIII. Effects of bioregulators on indole alkaloid biosynthesis  

Microsoft Academic Search

A study on the effect of various bioregulators on the biosynthesis of ajmalicine (8) and catharanthine (9) in plant tissue cultures of Catharanthus roseus is described. It is shown that 1,1-dimethylpiperidine bromide (3) and 2-diethylaminoethyl-3,4-dimethylphenylether (7) are effective in increasing these alkaloid levels in the cell line PRL #200. Such studies may prove beneficial in larger scale experiments designed for

James P. Kutney; Barbara Aweryn; Kenneth B. Chatson; Lewis S. L. Choi; Wolfgang G. W. Kurz



[Effect produced by the alkaloid fraction of Mimosa tenuiflora (tepescohuite) on the peristaltic reflex of the guinea pig ileum].  


An alkaloidal fraction was obtained from Mimosa tenuiflora (Willd.) Poir (tepescohuite) trunk bark. The product contained mainly an indolealkylamine and three minor alkaloids. This fraction inhibited the peristaltic reflex in the guinea-pig isolated ileum in vitro. PMID:2103706

Meckes-Lozoya, M; Lozoya, X; González, J L; Martínez, M



Analysis of Alkaloids from Physalis peruviana by Capillary GC, Capillary GC-MS, and GC-FTIR.  


The alkaloid composition of the aerial parts and roots of PHYSALIS PERUVIANA was analysed by capillary GC (GC (2)), GC (2)-MS and GC (2)-FTIR. Eight alkaloids were identified, three of those alkaloids are 3beta-acetoxytropane and two N-methylpyrrolidinylhygrine isomers, which were not previously found in the genus PHYSALIS. A reproduction of the identification of alkaloids detected in the plant by the use of retention indices has been proposed. PMID:17230349

Kubwabo, C; Rollmann, B; Tilquin, B



[Expression pattern of genes involved in tropane alkaloids biosynthesis and tropane alkaloids accumulation in Atropa belladonna].  


Atropa belladonna is a medicinal plant and main commercial source of tropane alkaloids (TAs) including scopolamine and hyoscyamine, which are anticholine drugs widely used clinically. Based on the high throughput transcriptome sequencing results, the digital expression patterns of UniGenes representing 9 structural genes (ODC, ADC, AIH, CPA, SPDS, PMT, CYP80F1, H6H, TRII) involved in TAs biosynthesis were constructed, and simultaneously expression analysis of 4 released genes in NCBI (PMT, CYP80F1, H6H, TRII) for verification was performed using qPCR, as well as the TAs contents detection in 8 different tissues. Digital expression patterns results suggested that the 4 genes including ODC, ADC, AIH and CPA involved in the upstream pathway of TAs, and the 2 branch pathway genes including SPDS and TRII were found to be expressed in all the detected tissues with high expression level in secondary root. While the 3 TAs-pathway-specific genes including PMT, CYP80F1, H6H were only expressed in secondary roots and primary roots, mainly in secondary roots. The qPCR detection results of PMT, CYP80F1 and H6H were consistent with the digital expression patterns, but their expression levels in primary root were too low to be detected. The highest content of hyoscyamine was found in tender stems (3.364 mg x g(-1)), followed by tender leaves (1.526 mg x g(-1)), roots (1.598 mg x g(-1)), young fruits (1.271 mg x g(-1)) and fruit sepals (1.413 mg x g(-1)). The highest content of scopolamine was detected in fruit sepals (1.003 mg x g(-1)), then followed by tender stems (0.600 mg x g(-1)) and tender leaves (0.601 mg x g(-1)). Both old stems and old leaves had the lowest content of hyoscyamine and scopolamine. The gene expression profile and TAs accumulation indicated that TAs in Atropa belladonna were mainly biosynthesized in secondary root, and then transported and deposited in tender aerial parts. Screening Atropa belladonna secondary root transcriptome database will facilitate unveiling the unknown enzymatic reactions and the mechanisms of transcriptional control. PMID:24754168

Qiang, Wei; Wang, Ya-Xiong; Zhang, Qiao-Zhuo; Li, Jin-Di; Xia, Ke; Wu, Neng-Biao; Liao, Zhi-Hua



Peroxidase and the biosynthesis of terpenoid indole alkaloids in the medicinal plant Catharanthus roseus (L.) G. Don  

Microsoft Academic Search

The leaves of Catharanthus roseus (L.) G. Don produce the first natural drugs used in cancer therapy – the dimeric terpenoid indole alkaloids vinblastine and vincristine. The study of C. roseus further revealed two other terpenoid indole alkaloids with important pharmacological activity: ajmalicine, used as an antihypertensive, and serpentine, used as sedative. The biosynthetic pathway of the medicinal alkaloids has

M. Sottomayor; I. Lopes Cardoso; L. G. Pereira; A. Ros Barceló



Cyclopeptide alkaloids. Synthesis of the ring system and its ion affinity  

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 occurring cyclopeptide alkaloid, ceanothine B, bind

J. Clark Lagarias; Richard A. Houghten; Henry Rapoport



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



[Preparative separation of alkaloids from Cortex Phellodendri by high speed countercurrent chromatography].  


High speed countercurrent chromatography was successfully applied to the separation of alkaloids from Cortex Phellodendri with a two-phase solvent system composed of CHCl3-CH3OH-0.5 mol/L HCl (2:1:1, volume ratio). Some alkaloid components were obtained, and identification of berberine was made by thin-layer chromatography. PMID:12541982

Yuan, Li-Ming; Wu, Ping; Xia, Tao; Chen, Xue-Xian



Effect of feeding fescue seed containing ergot alkaloid toxins on stallion spermatogenesis and sperm cells.  


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; De La Fuente, R; Baumann, C; Jones, L



Recyclable fluorous cinchona alkaloid ester as a chiral promoter for asymmetric fluorination of ?-ketoesters  

PubMed Central

Summary A fluorous cinchona alkaloid ester has been developed as a chiral promoter for the asymmetric fluorination of ?-ketoesters. It has comparable reactivity and selectivity to the nonfluorous versions of cinchona alkaloids and can be easily recovered from the reaction mixture by simple fluorous solid-phase extraction (F-SPE) and used for the next round of reaction without further purification.

Huang, Xin; Zhang, Zijuan; Zhu, Dian-Rong; Cai, Chun



[Plants from New Caledonia. Alkaloids from Sarcomelicope dogniensis Hartley stem bark].  


Two new pyranofuroquinoline alkaloids, cis-1,2-dihydroxy-1,2 dihydroacronydine 2 and trans-1,2-dihydroxy-1,2-dihydroacronydine 3 have been isolated from Sarcomelicope dogniensis stem bark. Their structures have been elucidated by spectral analysis and chemical correlations. In addition, 11 other alkaloids have been isolated from the stem bark of this species. PMID:2634931

Mitaku, S; Skaltsounis, A L; Tillequin, F; Koch, M; Pusset, J



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

PubMed Central

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

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



Cytochromes P450 in the biosynthesis of glucosinolates and indole alkaloids  

Microsoft Academic Search

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

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



Terpenoid indole alkaloid biosynthesis and enzyme activities in two cell lines of Tabernaemontana divaricata  

Microsoft Academic Search

The possible limitation of the rate of biosynthesis of terpenoid indole alkaloids by low enzyme levels was investigated in two cell lines of Tabernaemontana divaricata with different terpenoid indole alkaloid biosynthetic capacities. The activities of tryptophan decarboxylase (TDC), strictosidine synthase (SSS), strictosidine glucosidase (SG), isopentenyl pyrophosphate isomerase (IPP isomerase) and geraniol 10-hydroxylase (G10H) of both cell lines were compared. The

Denise Dagnino; Jan Schripsema; Robert Verpoorte



Petrosamine, a potent anticholinesterase pyridoacridine alkaloid from a Thai marine sponge Petrosia n. sp  

Microsoft Academic Search

Two pyridoacridine alkaloids, including a known petrosamine and a new 2-bromoamphimedine were isolated from a Thai marine sponge Petrosia n. sp. The alkaloids were characterized on the basis of 1D and 2D NMR, MS, and IR spectroscopy. Only petrosamine showed strong acetylcholinesterase inhibitory activity approximately six times higher than that of the reference galanthamine. A computational docking study of petrosamine

Veena S. Nukoolkarn; Suwipa Saen-oon; Thanyada Rungrotmongkol; Supot Hannongbua; Kornkanok Ingkaninan; Khanit Suwanborirux



Pyridoacridine Alkaloids Inducing Neuronal Differentiation in a Neuroblastoma Cell Line, from Marine Sponge Biemna fortis  

Microsoft Academic Search

A new and three known pyridoacridine alkaloids were isolated from the Indonesian marine sponge Biemna fortis as neuronal differentiation inducers against a murine neuroblastoma cell line, Neuro 2A. The chemical structure of the new compound, labuanine A (1), was determined by spectroscopic study and chemical conversion. These pyridoacridine alkaloids induced multipolar neuritogenesis in more than 50% of cells at 0.03–3

Shunji Aoki; Hong Wei; Kouhei Matsui; Rachmaniar Rachmat; Motomasa Kobayashi



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

PubMed Central

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

Ondrus, Alison E.; Movassaghi, Mohammad



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.

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



Effect of Colchicine Treatment on the Alkaloidal Content of Datura metel  

Microsoft Academic Search

As a result of the work of Rowson1, who found that the induced polyploids of various Solanaceous plants possessed higher alkaloidal contents than the normal varieties, we have investigated during the past two years the effect of colchicine treatment on the alkaloidal content of Datura metel, a commercial source of hyoscine.

A. E. Beesley; G. E. Foster



Radiation effects on growth and concentration of total alkaloids in Datura metel L  

Microsoft Academic Search

Seeds of D. metel were irradiated with 10 to 30 kR of gamma rays with ; a view to studying their effect on the morphological characters and the ; concentration of total alkaloids. There were several morphological and ; cytological abnormalities and the concentration of total alkaloids showed a ; remarkable increase (maximum increase was found at 10 kR). (auth);

B. L. Kaul; C. Singh; U. Zutshi; K. L. Dhar



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.

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



Identification of Topoisomerase I as the Cytotoxic Target of the Protoberberine Alkaloid Coralyne1  

Microsoft Academic Search

Protoberberine alkaloids (coralyne and its derivatives), which exhibit antileukemic activity in animal models, have been shown to be potent inducers of topoisomerase (topo) I-DNA cleavable complexes using pun- lied recombinant human DNA topo I. Different from the structurally similar benzophenanthridine alkaloid nitidine (a dual poison of both topos I and II), coralyne and its derivatives have marginal poisoning activity against

Barbara Gatto; Marilyn M. Sanders; Chiang Yu; Hong-Yan Wu; Darshan Makhey; Edmond J. LaVoie; Leroy F. Liu


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


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



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

NASA Astrophysics Data System (ADS)

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

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



Supercritical carbon dioxide extraction of colchicine and related alkaloids from seeds of Colchicum autumnale L.  


A method for the extraction of the alkaloids colchicine, 3-demethylcolchicine and colchicoside from seeds of Colchicum autumnale by supercritical carbon dioxide has been established. Several parameters such as pressure, temperature, percentage of modifier and extraction time have been examined. Two extraction steps with constant carbon dioxide density (0.90 g/mL) and flux (1.5 mL/min) were required to extract the alkaloids in 110 min using 3% methanol as modifier. The quantitative determination of the alkaloids was performed by HPLC; the percentages of recovery were higher than 98% for the three alkaloids. This extraction procedure was compared with a conventional method involving maceration and sonication, and the same levels of alkaloids were obtained in each case. The supercritical carbon dioxide method is, however, very efficient, more rapid and more environmentally friendly than conventional methods. PMID:12793464

Ellington, Ernesto; Bastida, Jaume; Viladomat, Francesc; Codina, Caries



Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase.  


Putrescine N-methyltransferase (PMT) is the first alkaloid-specific enzyme for nicotine and tropane alkaloid formation. The pmt gene from Nicotiana tabacum was fused to the CaMV 35S promoter and integrated into the Atropa belladonna genome. Transgenic plants and derived root cultures were analysed for gene expression and for levels of alkaloids and their precursors. Scopolamine, hyoscyamine, tropine, pseudotropine, tropinone, and calystegines were found unaltered or somewhat decreased in pmt-overexpressing lines compared to controls. When root cultures were treated with 5% sucrose, calystegine levels were elevated in control roots, but were not affected in pmt-overexpressing roots. 1 microM auxin reduced calystegine levels in control roots, while in pmt-overexpressing roots all alkaloids remained unaltered. Expression level of pmt alone is apparently not limiting for tropane alkaloid formation in A. belladonna. PMID:12885861

Rothe, Grit; Hachiya, Akira; Yamada, Yasuyuki; Hashimoto, Takashi; Dräger, Birgit



Quinolizidine alkaloid profiles of Lupinus varius orientalis, L. albus albus, L. hartwegii, and L. densiflorus.  


Alkaloid profiles of two Lupinus species growing naturally in Egypt (L. albus albus [synonym L. termis], L. varius orientalis) in addition to two New World species (L. hartwegii, L. densiflorus) which were cultivated in Egypt were studied by capillary GLC and GLC-mass spectrometry with respect to quinolizidine alkaloids. Altogether 44 quinolizidine, bipiperidyl and proto-indole alkaloids were identified; 29 in L. albus, 13 in L. varius orientalis, 15 in L. hartwegii, 6 in L. densiflorus. Some of these alkaloids were identified for the first time in these plants. The alkaloidal patterns of various plant organs (leaves, flowers, stems, roots, pods and seeds) are documented. Screening for antimicrobial activity of these plant extracts demonstrated substantial activity against Candida albicans, Aspergillus flavus and Bacillus subtilis. PMID:11302208

El-Shazly, A; Ateya, A M; Wink, M



Advanced treatment of high strength opium alkaloid industry effluents.  


The purpose of this study was to investigate an effective treatment system which can be applicable to treat opium alkaloid industry (OAI) effluents characterised with high COD, TKN, dark color and non-biodegradable organic pollutants. In the first phase of the study, lab-scale anaerobic (UASBR) + aerobic (SBR) treatability studies were carried out on opium processing industry effluents. Effluent CODs from the two staged biological treatment system were relatively high (-700 mg l(-1)) and additional post treatment was required. Physico-chemical treatability studies previously carried out on the effluent of opium alkaloid wastewater treatment plant, were not effective in removing residual COD and color. In the second phase of the study, the refractory organics causing higher inert COD values in the SBR effluent were additionally treated by using Fenton's Oxidation. The batch tests were performed to determine the optimum operating conditions including pH, H2O2 dosage, molar ratio of Fe2+/H2O2 and reaction time. It was found that removal efficiencies of COD and color for 30 minutes reaction time were about 90% and 95%, respectively. The ratio of H2O2/FeSO4 was determined as 200 mg l(-1)/600 mg l(-1) for the optimum oxidation and coagulation process at pH 4. Experimental results of the present study have clearly indicated that the Fenton's oxidation technology is capable to treat almost all parts of the organics which consist of both soluble initial and microbial inert fractions of COD for opium alkaloid industry effluents. Effluents from the Fenton's Oxidation process can satisfy effluent standards for COD and color in general. PMID:12448485

Aydin, A F; Altinbas, M; Sevimli, M F; Ozturk, I; Sarikaya, H Z



Alkaloids from an endophytic streptomyces sp. YIM66017.  


Three alkaloids, flavensomycinoic acid (1), a linear polyketide, alpiniamide (2), and cyclo (L-Trp-L-Ala) (3), were isolated from the culture filtrate of endophytic Streptomyces sp. YIM66017 from Alpinia oxyphylla. Their structures were elucidated by spectroscopic analysis and the structure of 1 was confirmed by X-ray crystallographic analysis. Compound 1 was isolated from a natural source for the first time, and compound 2 is a new compound. Compound 1 showed cytotoxicity to MCF-7 with an IC50 value of 17.0 microM. PMID:24354182

Zhou, Hao; Yang, Yabin; Zhang, Jucheng; Peng, Tianfeng; Zhao, Lixing; Xu, Lihua; Ding, Zhongtao



Cytotoxic azaphilone alkaloids from Chaetomium globosum TY1.  


Three novel azaphilone alkaloids, namely chaetomugilides A-C (1-3), together with three related compounds (4-6) were isolated from the methanol extract of Chaetomium globosum TY1, an endophytic fungus isolated from Ginkgo biloba. Their structures were elucidated on the basis of extensive 1D and 2D NMR as well as HRESI-MS spectroscopic data analysis. The isolated compounds exhibited highly cytotoxic activities against human cancer cell line HePG2 with the IC50 values range from 1.7 to 53.4?M. PMID:23562244

Li, Xiang; Tian, Ye; Yang, Sheng-Xiang; Zhang, Ya-Mei; Qin, Jian-Chun



Anti-HIV and cytotoxic alkaloids from Buchenavia capitata.  


The anti-HIV activity in the organic solvent extract of leaves of Buchenavia capitata was traced to a series of known flavonoid alkaloids, which represent a new chemotype for anti-HIV activity. The 13C-nmr assignments for this series of compounds have been revised. O-Demethylbuchenavianine [1] was the most active compound of the series but produced only moderate cytoprotective effects against HIV in cultured human lymphoblastoid (CEM-SS) cells. Compound 1 was cytotoxic also in the NCI human disease-oriented in vitro tumor screening panel and produced a pattern of modest differential cellular sensitivity. PMID:1624941

Beutler, J A; Cardellina, J H; McMahon, J B; Boyd, M R; Cragg, G M



Evaluation of pyridoacridine alkaloids in a zebrafish phenotypic assay.  


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



Evaluation of Pyridoacridine Alkaloids in a Zebrafish Phenotypic Assay  

PubMed Central

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 ?M. No phenotype other than death was observed for compounds 1–3, 5, 6.

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.



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


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

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



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


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



Numerical Errors: Reliable Numerical Simulations.  

National Technical Information Service (NTIS)

Understanding numerical errors in long calculations is a very subtle science and is critical to understanding the reliability of the final answer. We will carefully examine the accumulation of numerical errors over time and discuss how these can lead to r...

L. Jameson



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


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

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



Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy  

PubMed Central

The phenanthroindolizidine and phenanthroquinolizidine alkaloids, typified by tylophorine and cryptopleurine, are a family of plant-derived small molecules with significant therapeutic potential. The plant extracts have been used in herbal medicine and the isolated compounds have displayed a range of promising therapeutic activity such as anti-ameobicidal, anti-viral, anti-inflammatory and anti-cancer activity. Despite their therapeutic protential, no compounds in this class have fully passed clinical trials. Drawbacks include low in vivo anti-cancer activity, central nervous system toxicity and low natural availability. A number of biological effects of these compounds, such as protein and nucleic acid synthesis suppression, have been identified, but the specific biomolecular targets have not yet been identified. Significant effort has been expended in the synthesis and structure-activity-relationship (SAR) studies of these compounds with the hope that a new drug will emerge. This review will highlight important contributions to the isolation, synthesis, SAR and mechanism of action of the phenanthroindolizidine and pheanthroquinolizidine alkaloids.

Chemler, Sherry R.



Beta-carboline alkaloids from the stems of Picrasma quassioides.  


Five new beta-carboline alkaloids, 6,12-dimethoxy-3-(2-hydroxylethyl)-beta-carboline (1), 3,10-dihydroxy-beta-carboline (2), 6,12-dimethoxy-3-(1-hydroxylethyl)-beta-carboline (3), 6,12-dimethoxy-3-(1,2-dihydroxylethyl)-beta-carboline (4), and 6-methoxy-3-(2-hydroxyl-1-ethoxylethyl)-beta-carboline (5), and two new natural products, 6-methoxy-12-hydroxy-3-methoxycarbonyl-beta-carboline (6) and 3-hydroxy-beta-carboline (7) were isolated from the stems of Picrasma quassioides along with 16 known beta-carboline alkaloids (8-23). The structures of new compounds were determined by extensive spectroscopic analyses, and the 1D and 2D NMR data of compounds 6, 7 and 10 were reported for the first time. The bioassays showed that only compounds 14 and 16 could enhance the differentiation of 3T3-L1 preadiocytes accompanied by secretion of adiponectin proteins among these 23 compounds. PMID:20474029

Jiao, Wei-Hua; Gao, Hao; Li, Chen-Yang; Zhou, Guang-Xiong; Kitanaka, Susumu; Ohmura, Atsuko; Yao, Xin-Sheng



Cytotoxic Alkaloids from the Whole Plants of Zephyranthes candida  

PubMed Central

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

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



The total synthesis of the Galbulimima alkaloid GB 13.  


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

Mander, Lewis N; McLachlan, Matthew M



Bioactive pyridoacridine alkaloids from the micronesian sponge Oceanapia sp.  


The Micronesian sponge Oceanapia sp. afforded three pyridoacridine alkaloids: the known compounds kuanoniamine C (1) and kuanoniamine D (2), as well as the new N-deacyl derivative (3) of the kuanoniamines. Compounds 1 and 2 exhibited insecticidal activity toward neonate larvae of the polyphagous pest insect Spodoptera littoralis (LC50 of 156 and 59 ppm, respectively), when incorporated into artificial diet. Both compounds also showed toxicity in the brine shrimp lethality test with a LC50 of 37 micrograms/mL (compound 1) and 19 micrograms/mL (compound 2), respectively. The N-deacyl derivative did not show any remarkable effect in both bioassays. Cytotoxcity of the alkaloids was studied in vitro, using two human cell lines. The new derivative (3) appeared to be active in the same range of concentrations as kuanoniamine C (1) and D (2). The IC50 of 3 was 1.2 micrograms/mL toward HeLa cells and 2.0 micrograms/mL toward MONO-MAC 6 cells. In receptor binding assays compound 2 showed affinity to A1- and A2A-adenosine receptors with Ki values of 2.94 and 13.7 microM, respectively. Compound 1 was less active than compound 2, whereas compound 3 showed no affinity toward adenosine receptors. In addition, compounds 1-3 exhibited moderate affinity to benzodiazepine binding sites of GABAA receptors. PMID:9514015

Eder, C; Schupp, P; Proksch, P; Wray, V; Steube, K; Müller, C E; Frobenius, W; Herderich, M; van Soest, R W



Acridone alkaloids as potent inhibitors of cathepsin V.  


Cathepsin V is a lysosomal cysteine peptidase highly expressed in thymus, testis and corneal epithelium. Eleven acridone alkaloids were isolated from Swinglea glutinosa (Bl.) Merr. (Rutaceae), with eight of them being identified as potent and reversible inhibitors of cathepsin V (IC(50) values ranging from 1.2 to 3.9 ?M). Detailed mechanistic characterization of the effects of these compounds on the cathepsin V-catalyzed reaction showed clear competitive inhibition with respect to substrate, with dissociation constants (K(i)) in the low micromolar range (2, K(i)=1.2 ?M; 6, K(i)=1.0 ?M; 7, K(i)=0.2 ?M; and 11, K(i)=1.7 ?M). Molecular modeling studies provided important insight into the structural basis for binding affinity and enzyme inhibition. Experimental and computational approaches, including biological evaluation, mode of action assessment and modeling studies were successfully employed in the discovery of a small series of acridone alkaloid derivatives as competitive inhibitors of catV. The most potent inhibitor (7) has a K(i) value of 200 nM. PMID:21277783

Severino, Richele P; Guido, Rafael V C; Marques, Emerson F; Brömme, Dieter; da Silva, M Fátima das G F; Fernandes, Joăo B; Andricopulo, Adriano D; Vieira, Paulo C



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


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

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



Binding of plant alkaloids berberine and palmatine to serum albumins: a thermodynamic investigation.  


The thermodynamics of the interaction of two pharmaceutically important isoquinoline alkaloids berberine and palmatine with bovine and human serum albumin was investigated using calorimetric techniques, and the data was supplemented with fluorescence and circular dichroism studies. Thermodynamic results revealed that there was only one class of binding sites for both alkaloids on BSA and HSA. The equilibrium constant was of the order of 10(4) M(-1) for both the alkaloids to serum albumins but the magnitude was slightly higher with HSA. Berberine showed higher affinity over palmatine to both proteins. The binding was enthalpy dominated and entropy favoured for both the alkaloids to BSA and HSA. Salt dependent studies suggested that electrostatic interaction had a significant role in the binding process, the binding affinity reduced as the salt concentration increased. Temperature dependent calorimetric data yielded heat capacity values that suggested the involvement of different molecular forces in the complexation of the two alkaloids with BSA and HSA. 3D fluorescence, synchronous fluorescence and circular dichroism data suggested that the binding of the alkaloids changed the conformation of proteins by reducing their helicity. Destabilization of the protein conformation was also revealed from differential scanning calorimetry studies. Overall, the alkaloids bound strongly to serum albumins, but berberine was a better binder to both serum proteins compared to palmatine. PMID:23065224

Khan, Asma Yasmeen; Hossain, Maidul; Kumar, Gopinatha Suresh



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


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



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


The medicinally applied tropane alkaloids hyoscyamine and scopolamine are produced in Atropa belladonna L. and in a small number of other Solanaceae. Calystegines are nortropane alkaloids that derive from a branching point in the tropane alkaloid biosynthetic pathway. In A. belladonna root cultures, calystegine molar concentration is 2-fold higher than that of hyoscyamine and scopolamine. In this study, two tropinone reductases forming a branching point in the tropane alkaloid biosynthesis were overexpressed in A. belladonna. Root culture lines with strong overexpression of the transcripts contained more enzyme activity of the respective reductase and enhanced enzyme products, tropine or pseudotropine. High pseudotropine led to an increased accumulation of calystegines in the roots. Strong expression of the tropine-forming reductase was accompanied by 3-fold more hyoscyamine and 5-fold more scopolamine compared with control roots, and calystegine levels were decreased by 30-90% of control. In some of the transformed root cultures, an increase of total tropane alkaloids was observed. Thus, transformation with cDNA of tropinone reductases successfully altered the ratio of tropine-derived alkaloids versus pseudotropine-derived alkaloids. PMID:15642710

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



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


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

Zayed, Rawia; Wink, Michael



Quantitative analysis of tropane alkaloids in biological materials by gas chromatography-mass spectrometry.  


A simple and rapid method for quantitation of tropane alkaloids in biological materials has been developed using an Extrelut column with gas chromatography-mass spectrometry (GC-MS). Biological materials (serum and urine) were mixed with a borate buffer and then applied to an Extrelut column. The adsorbed tropane alkaloids were eluted with dichloromethane before a GC-MS analysis. Atropine-d(3) was used as an internal standard. The extracted tropane alkaloids were converted to trimethylsilyl derivatives prior to GC analysis, to improve the instability of tropane alkaloids from heating and the property of them for a GC column. The recoveries of the compounds, which had been spiked to biological materials, were more than 80%. The GC separation of the derivatives from endogenous impurities was generally satisfactory with the use of a semi-polar capillary column. Tropane alkaloids showed excellent linearity in the range of 10-5000 ng/ml and the limit of detection was 5.0 ng/ml for biological materials. The present method is simple and more rapid than those previously reported, and was applied to a poisoning case. It is useful for the routine analysis of tropane alkaloids in cases of suspected tropane alkaloids poisoning. PMID:12427448

Namera, Akira; Yashiki, Mikio; Hirose, Yasuo; Yamaji, Seiichi; Tani, Tadato; Kojima, Tohru



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


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



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


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



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


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



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.

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.



An atypical pattern of accumulation of scopolamine and other tropane alkaloids and expression of alkaloid pathway genes in Hyoscyamus senecionis.  


A cDNA encoding hyoscyamine 6?-hydroxylase (H6H, EC, a bifunctional enzyme catalyzing the last two steps in the scopolamine biosynthetic pathway, was isolated from Hyoscyamus senecionis, a medicinal plant endemic to the Iranian plateau. Expression analysis indicates that Hsh6h is expressed in all tested organs of H. senecionis including roots, rhizomes, leaves, stems and flowers unlike the other tropane alkaloid producing species. In parallel to this, in leaves, levels of scopolamine, the product of H6H, were higher than the substrate hyoscyamine. These data suggest that not only does the conversion of hyoscyamine to scopolamine take place in the root, followed by translocation to aerial parts, but also accumulated hyoscyamine in the aerial parts may be converted to scopolamine by activity of HsH6H. Analysis of expression profiles of putrescine N-methyltransferase and tropinone reductase I and II genes also indicates the organ-independent expression of these genes. Here we also introduce H. senecionis as an important tropane alkaloid producing species with its thick underground parts as a source of hyoscyamine, while its leaves can be considered as a source of scopolamine. PMID:23786817

Dehghan, Esmail; Shahriari Ahmadi, Farajollah; Ghotbi Ravandi, Elnaz; Reed, Darwin W; Covello, Patrick S; Bahrami, Ahmad Reza



Canthin-6-one alkaloids from Picrasma quassioides and their cytotoxic activity.  


A new alkaloid, 4,5-dimethoxy-10-hydroxycanthin-6-one (1), was isolated from the stem of Picrasma quassioides Bennet (Simaroubaceae) together with four known canthin-6-one alkaloids, 8-hydroxycanthin-6-one (2), 4,5-dimethoxycanthin-6-one (3), 5-hydroxy-4-methoxycanthin-6-one (4), and 3-methylcanthin-5,6-dione (5). Their structures were elucidated on the basis of spectroscopic data. The cytotoxic activity of the canthin-6-one alkaloids was evaluated using human nasopharyngeal carcinoma (CNE2) and human liver cancer (Bel-7402) cell lines. Among these isolates, compounds 1-4 exhibited significant cytotoxic activity against CNE2 cell line. PMID:19031238

Jiang, Mei-Xiang; Zhou, Ying-Jun



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

PubMed Central

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

Pan, Guojun; Williams, Robert M.



Megistoquinones I and II, two quinoline alkaloids with antibacterial activity from the bark of Sarcomelicope megistophylla.  


Two alkaloids, megistoquinone I (1) and megistoquinone II (2), were isolated from the bark of Sarcomelicope megistophylla. Their structures have been elucidated on the basis of MS and NMR data. Both belong to quinoline alkaloid series and should be considered as oxidation products of a furo[2,3-b]quinoline precursor. The two alkaloids showed antibacterial properties with minimum inhibitory concentration (MIC) ranging from 2.35 to 5.25 mg/ml for 1 and 0.73 to 1.23 mg/ml for 2. PMID:11911210

Fokialakis, Nikolas; Magiatis, Prokopios; Chinou, Ioanna; Mitaku, Sofia; Tillequin, François



Additional cytotoxic pyridoacridine alkaloids from the ascidian Cystodytes violatinctus and biogenetic considerations.  


The extraction and purification of the bioactive extract of Cystodytes violatinctus (Solomon Islands) led to the isolation and identification of six pyridoacridine alkaloids. The structures of four new members of this family, shermilamine F (1), dehydrokuanoniamine F (2), and arnoamines C (3) and D (4), were elucidated on the basis of NMR and MS data and by comparison with data of known compounds isolated from this genus. A general hypothetical biogenetic pathway is then proposed for pyridoacridine alkaloids that contain a fused pyrrole ring. Comparison of the biological properties of the isolated alkaloids is also discussed. PMID:23961991

Bontemps, Nataly; Gattacceca, Florence; Long, Christophe; Thomas, Olivier P; Banaigs, Bernard



Neonaucline, a new indole alkaloid from the leaves of Ochreinauclea maingayii (Hook. f.) Ridsd. (Rubiaceae).  


A new indole alkaloid; neonaucline (1), along with six known compounds-Cadamine (2), naucledine (3), harmane, benzamide, cinnamide and blumenol A-were isolated from the leaves of Ochreinauclea maingayii (Rubiaceae). In addition to that of compound 1, (13)C-NMR data of cadamine (2) and naucledine (3) were also reported. Structural elucidations of these alkaloids were performed using spectroscopic methods especially 1D- and 2D-NMR, IR, UV and LCMS-IT-TOF. The excellent vasorelaxant activity on isolated rat aorta was observed for the alkaloids 1-3 after injection of each sample at 1 × 10(-5) M. PMID:22205092

Muktar, Mat Ropi; Osman, Norfaizah; Awang, Khalijah; Hazni, Hazrina; Qureshi, Ahmad Kaleem; Hadi, A Hamid A; Zaima, Kazuma; Morita, Hiroshi; Litaudon, Marc



Influence of Some Heavy Metals on Growth, Alkaloid Content and Composition in Catharanthus roseus L.  

PubMed Central

Shoot biomass production, alkaloid content and composition as influence by cadmium, manganese, nickel and lead at uniform dose of 5 mM were investigated in Catharanthus roseus plants grown in sand culture. Treatment with Mn, Ni, and Pb significantly enhanced total root alkaloid accumulation. Cd and Ni treatment resulted in two-fold where as Pb treatment resulted in three fold increase in serpentine content of roots. The non-significant affect on biomass suggests that plants can withstand metal stress at the level tested with positive affect on root alkaloid content.

Srivastava, N. K.; Srivastava, A. K.



Study of alkaloids from Adhatoda vasica Nees on their antiinflammatory activity.  


Adhatoda vasica Nees is a shrub widespread throughout the tropical regions of southeast Asia. It possesses a wide spectrum of medicinal properties including positive effects on inflammatory diseases. The antiinflammatory activity of the methanol extract, the non-alkaloid fraction, the saponins and the alkaloids was evaluated by the modified hen's egg chorioallantoic membrane test. The alkaloid fraction showed potent activity at a dose of 50 microg/pellet equivalent to that of hydrocortisone while the MeOH extract and the other fractions showed less activity. PMID:11536385

Chakraborty, A; Brantner, A H



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.


Numerical Relativity  

NASA Technical Reports Server (NTRS)

Recent advances in numerical relativity have fueled an explosion of progress in understanding the predictions of Einstein's theory of gravity, General Relativity, for the strong field dynamics, the gravitational radiation wave forms, and consequently the state of the remnant produced from the merger of compact binary objects. I will review recent results from the field, focusing on mergers of two black holes.

Baker, John G.



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.

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



Design, synthesis and antistaphylococcal activity of marine pyrrole alkaloid derivatives.  


A novel set of 16 hybrids of bromopyrrole alkaloids with aroyl hydrazone were designed, synthesized and evaluated for antibacterial and antibiofilm activities against methicillin-resistant Staphylococcus aureus (MRSA; ATCC 43866), methicillin-susceptible Staphylococcus aureus (MSSA; ATCC 35556) and Staphylococcus epidermidis (SE, S. epidermidis ATCC 35984). Of the 16 tested hybrids, 14 exhibited equal or superior antibiofilm activity against MSSA and MRSA relative to standard vancomycin. Compound 4m showed highest potency with antibiofilm activity of 0.39?µg/mL and 0.78?µg/mL against MSSA and MRSA, respectively. Thus, this compound could act as a potential lead for further development of new antistaphylococcal drugs. PMID:23663080

Rane, Rajesh A; Sahu, Niteshkumar U; Shah, Chetan P; Shah, Nishant K



Cytochrome P450 as dimerization catalyst in diketopiperazine alkaloid biosynthesis.  


As dimeric natural products frequently exhibit useful biological activities, identifying and understanding their mechanisms of dimerization is of great interest. One such compound is (?)-ditryptophenaline, isolated from Aspergillus flavus, which inhibits substance P receptor for potential analgesic and anti-inflammatory activity. Through targeted gene knockout in A. flavus and heterologous yeast gene expression, we determined for the first time the gene cluster and pathway for the biosynthesis of a dimeric diketopiperazine alkaloid. We also determined that a single cytochrome P450, DtpC, is responsible not only for pyrroloindole ring formation but also for concurrent dimerization of N-methylphenylalanyltryptophanyl diketopiperazine monomers into a homodimeric product. Furthermore, DtpC exhibits relaxed substrate specificity, allowing the formation of two new dimeric compounds from a non-native monomeric precursor, brevianamide F. A radical-mediated mechanism of dimerization is proposed. PMID:24677498

Saruwatari, Takayoshi; Yagishita, Fumitoshi; Mino, Takashi; Noguchi, Hiroshi; Hotta, Kinya; Watanabe, Kenji



Alkaloids from Xylariaceae sp., a marine-derived fungus.  


A new pyridine derivative, 5-(2'-hydroxypropyl)pyridin-3-ol (1), with seven known alkaloids, 3-hydroxy-5-methyl-5,6-dihydro-7H-cyclopenta[b]pyridin-7-one (2), penicillenol A1 (3), penicillenol A2 (4), a mixture of quinolactacin AI (5a) and quinolactacin A2 (5b), and a mixture of quinolactacin C1 (6a) and quinolactacin C2 (6b), were isolated from the culture broth of a marine-derived fungus Xylariaceae sp. SCSGAF0086. Their structures were elucidated by spectroscopic methods. Compound 2 showed weak antimicrobial activity against Bacillus subtilis, and a mixture of 6a and 6b exhibited strong antifouling activity toward Bugula neritina larval settlement. PMID:24868856

Nong, Xu-Hua; Zhang, Xiao-Yong; Xu, Xin-Ya; Sun, Yun-Lin; Qi, Shu-Hua



Dihydroagarofuran alkaloid and triterpenes from Maytenus heterophylla and Maytenus arbutifolia.  


The antimicrobially active EtOH extracts of Maytenus heterophylla yielded a new dihydroagarofuran alkaloid,1beta-acetoxy-9alpha-benzoyloxy-2beta,6alpha-dinicotinoyloxy-beta-dihydroagarofuran, together with the known compounds beta-amyrin, maytenfolic acid, 3alpha-hydroxy-2-oxofriedelane-20alpha-carboxylic acid, lup-20(29)-ene-1beta,3beta-diol, (-)-4'-methylepigallocatechin, and (-)-epicatechin. In addition, beta-amyrin, (-)-epicatechin and (-)-4'-methylepigallocatechin were isolated from Maytenus arbutifolia. The structure elucidation of the isolated compounds was based primarily on 1D and 2D NMR analyses, including HMQC, HMBC, and NOESY correlations. Maytenfolic acid showed moderate antimicrobial activity by inhibiting the growth of Candida albicans, Cryptococcus neoformans, Staphylococcus aureus and Pseudomonas aeruginosa. PMID:11557080

Orabi, K Y; Al-Qasoumi, S I; El-Olemy, M M; Mossa, J S; Muhammad, I



Vitiquinolone--a quinolone alkaloid from Hibiscus vitifolius Linn.  


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

Ramasamy, D; Saraswathy, A



Hydrogenation of cinchona alkaloids over supported Pt catalyst.  


The heterogeneous catalytic hydrogenation of two isomeric cinchona alkaloids, cinchonidine and cinchonine, was studied over Pt/Al(2)O(3) in 1N H(2)SO(4) solution under 100 bar H(2) at 25 degrees C. Cinchonidine was transformed into two diastereomeric hexahydroderivatives by hydrogenation of ring A (with N) of the quinoline moiety (yield over 95%, diastereomeric ratio 2/3), whereas hydrogenation of cinchonine resulted in the formation of three products, the major one being formed by the hydrogenation of ring B (without N) (yield 60%). The isolated hexahydroderivatives were investigated by (1)H-, (13)C-NMR, (1)H-(1)H COSY, (1)H-(13)C HetCOSY, and NOESY spectroscopy and were used as modifiers in the heterogeneous enantioselective hydrogenation of ethyl pyruvate and as catalysts in the Michael addition of ethyl 2-oxocyclopentanecarboxylate to methyl vinyl ketone. PMID:12884378

Szöllosi, György; Forgó, Péter; Bartók, Mihály



Analytical aspects of diterpene alkaloid poisoning with monkshood.  


A sensitive and specific method for aconitine extraction from biological samples was developed. Aconitine, the main toxic alkaloid from plants belonging to Aconitum species (family Ranunculaceae), was determined in plant material by an external standard method, and by a standard addition calibration method in biological fluids. Described here is one fatal case and five intoxications of accidental aconitine poisoning following the ingestion of aconite mistaken for an edible grass, Aruncus dioicus (Walt.) Fernald, "mountain asparagus", and Cicerbita alpina (L.) Wallroth. The aconitine content in urine was in the range 2.94 microg/mL (dead patient)-0.20 microg/mL (surviving patients), which was almost two to four times higher than that in plasma. PMID:19967988

Colombo, Maria Laura; Bugatti, Carlo; Davanzo, Franca; Persico, Andrea; Ballabio, Cinzia; Restani, Patrizia



Pyrroloacridine Alkaloids from Plakortis quasiamphiaster: Structures and Bioactivity  

PubMed Central

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

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



[A new indole alkaloid from the stems of Brucea mollis].  


Eight compounds were isolated from the stems of Brucea mollis by various chromatographic techniques such as column chromatography on silica gel and Sephadex LH-20, and preparative HPLC, and their structures were elucidated as bruceolline O (1), 1-(1-beta-glucopyranosyl)-1H-indole-3-carbaldehyde (2), canthin-6-one (3), 11-hydroxycanthin-6-one (4), 9-methoxycanthin-6-one (5), 4-methoxycanthin-6-one (6), infractin (7), and beta-carboline-1-propionic acid (8). The cytotoxic activities of compounds 1-8 against HCT-8 and A549 human cell lines were determined, but none of them exhibited significant activity (IC 50 > 10 micromol x L(-1)). Among them, compound 1 is a new indole alkaloid, and compounds 2 and 5-7 were isolated from this plant for the first time. PMID:24761613

Chen, Hui; Shuang-Gang, M A; Fang, Zhen-Feng; Zhang, Gui-Jie; Yu, Shi-Shan; Chen, Xiao-Guang



Degradation of quinolizidine alkaloids of lupin by Rhizopus oligosporus.  


Rhizopus oligosporus has proven beneficial in the detoxification of lupin seeds. The fermentation process is mainly affected by the initial pH in the medium. In the range of growth of mold, there are maximum enzymatic activities in pH of 3.5 and 5.5. Metabolism change occurs at these pH levels; therefore, we studied the growth, pH changes, dry matter intake, and alkaloid degradation within 48 h of fermentation. Cultures of lupin agar (LA) with pH of 3.5 and 5.5 were made in Petri dishes with lupin flour. Results showed pH directly affects the degradation of alkaloids and fungal growth. Detoxification levels achieved were 16.58 and 63.23 % in treatments LA 3.5 and LA 5.5, respectively. Fungal growth was 0.919 mg/cm(2) in LA 3.5 and 1.081 mg/cm(2) in LA 5.5. Maximum degradation rate in LA 5.5 was given between 16 and 20 h, which coincided with maximum fungal growth. Despite having similar dry matter intake in both treatments, a pH of 3.5 did not show the same degree of detoxification. The analysis with exponential, yield of growth, yield of dry matter intake and luedeking and piret equations, confirm the relation between intake and growth with detoxification. Dry matter intake equation predicts with R (2) of 0.94 the detoxification in LA 5.5. A pH of 5.5 is directly related with detoxification and fungal development. PMID:23435939

Ortega-David, Eduar; Rodríguez-Stouvenel, Aida



Mw Systematic Study of Alkaloids: the Distorted Tropane of Scopoline  

NASA Astrophysics Data System (ADS)

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

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



The carbon-skeleton rearrangement in tropane alkaloid biosynthesis.  


High-level quantum chemistry calculations have been performed to examine the carbon-skeleton rearrangement of the tropane alkaloid littorine to hyoscyamine. Two pathways involving radical and carbocation intermediates have been investigated in this regard, namely, stepwise (or fragmentation-recombination) and concerted. The fragmentation products are calculated to be of high energy for both the radical- and carbocation-based mechanisms (136.3 and 170.9 kJ mol(-1), respectively). Similarly, the rearrangement barrier for the radical-based concerted pathway is calculated to be quite high (135.6 kJ mol(-1)). In contrast, the carbocation-based concerted pathway is found to be associated with a relatively low barrier (47.4 kJ mol(-1)). The ionization energy of the substrate-derived radical 3a is calculated to be 7.01 eV, suggesting that its oxidation to generate the substrate-derived carbocation 3b ought to be facile. In an attempt to investigate how an enzyme might modulate the rearrangement barriers, the separate and combined influences of partially protonating the migrating group and partially deprotonating the spectator OH group of the substrate were investigated. Such interactions can lead to significant reductions in the rearrangement barrier for both the radical- and carbocation-based concerted pathways, although the carbocation pathway continues to have significantly lower energy requirements. Also, the relatively high (gas-phase) acidity of the OH group of the product-related carbocation 4b indicates that the direct formation of hyoscyamine aldehyde (6) is a highly exothermic process. Although we would not wish to rule out alternative possibilities, our calculations suggest that a concerted rearrangement mechanism involving carbocations constitutes a viable low-energy pathway for the carbon-skeleton rearrangement in tropane alkaloid biosynthesis. PMID:18627156

Sandala, Gregory M; Smith, David M; Radom, Leo



Determination of protoberberine alkaloids in medicinal plants based on acidic potassium permanganate chemiluminescence system.  


A simple method was established to determine protoberberine alkaloids in Cortex Phellodendri and Rhizoma Coptidis based on an acidic potassium permanganate chemiluminescence (CL) system. The optimum conditions for the CL reaction between protoberberine alkaloids and potassium permanganate were studied in detail. Under the optimum conditions, the linear response ranges for berberine, palmatine and jatrorrhizine were 0.038-7.27, 0.031-18.1 and 0.012-3.61??g/mL with detection limits of 0.005, 0.004 and 0.0007??g/mL, respectively. This method was successfully applied to determine the content of protoberberine alkaloids (calculated using berberine as an index) in Cortex Phellodendri and Rhizoma Coptidis. In addition, a possible mechanism of this CL reaction was proposed on the basis of the investigation of CL, UV and fluorescent spectra of protoberberine alkaloids in acidic solution containing potassium permanganate. PMID:19743526

Xu, Xueqin; Lin, Qiang; He, Xiaoyan; Fu, FengFu; Chen, Guonan



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.

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



Chaetoglobins A and B, two unusual alkaloids from endophytic Chaetomium globosum culture.  


Chaetoglobins A (1) and B (2), two azaphilone alkaloid dimers with an unprecedented skeleton, were characterized from an endophytic fungus Chaetomium globosum with the former ascertained to be a significant cytotoxin valuable for anti-tumor drug discovery. PMID:19030558

Ming Ge, Hui; Yun Zhang, Wei; Ding, Gang; Saparpakorn, Patchareenart; Chun Song, Yong; Hannongbua, Supa; Tan, Ren Xiang



Production of tropane alkaloids during de-differentiation of Scopolia parviflora calli.  


The production of tropane alkaloids during differentiation and de-differentiation of Scopolia parviflora calli was studied. Tropane alkaloid production drastically decreased during calli de-differentiation. Scopolamine (1) production decreased after 10 days of culture, whereas that of hyoscyamine (2) decreased during de-differentiation of root to calli. The production of 1 was enhanced in calli undergoing differentiation to shoot after 60 days of culture, reaching a maximum by 80 days. However, production of hyoscyamine in regenerated plants was lower. The expression level of hyoscyamine 6beta-hydroxylase (H6H), a key biosynthetic enzyme for tropane alkaloids, was significantly increased in 4-week-old calli. This study suggests that the biosynthesis of tropane alkaloids is regulated inversely in de-differentiating Scopolia parviflora calli. PMID:20141164

Kim, Yong Duck; Kang, Seung Mi; Min, Ji Yun; Choi, Won Kyun; Jeong, Mi Jin; Karigar, Chandrakant S; Choi, Myung Suk



Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS.  


Sixty seven tropane alkaloids were identified in the organs of Datura stramonium L. by GC/MS. Nine new tropane alkaloids, 3,7-dihydroxy-6-propionyloxytropane, 6,7-dehydro-3-tigloyloxytropane, 3-tigloyloxy-6,7-epoxytropane, 3,7-dihydroxy-6-(2'-methylbutyryloxy)tropane, 6,7-dehydroapoatropine, 3-(3'-methoxytropoyloxy)tropane, 3-tigloyloxy-6-isobutyryloxy-7-hydroxytropane, 3-tropoyloxy-6-isobutyryloxytropane, 3?-tropoyloxy-6?-isovaleroyloxytropane were tentatively identified. The alkaloids cyclotropine, dihydroaposcopolamine, 6,7-dehydrohyoscyamine and 4'-hydroxylittorine are reported for the first time for the genus Datura and 6,7-dehydrotropine for the family Solanaceae. Hyoscyamine and scopolamine figure as the major tropane alkaloids in the plant organs. PMID:20858536

El Bazaoui, Ahmed; Bellimam, My Ahmed; Soulaymani, Abdelmajid



Evolutionary ecology of the tropane alkaloids of Datura stramonium L. (Solanaceae).  


Although insect herbivory is frequently assumed to be responsible for the maintenance of plant secondary metabolites such as alkaloids, the assumption is controversial and experimental evidence for this assumption is sparse. We examined natural selection on the two major alkaloids present in the leaves of Datura stramonium and found that both alkaloids came under active selection. We found negative directional selection for scopolamine (natural selection acting to reduce scopolamine levels) and stabilizing selection for hyoscyamine (natural selection acting to maintain an intermediate level of hyoscyamine). We also present evidence that insect herbivores act as the agents of selection on these alkaloids. Finally, we show that there were no trade-offs in resistance to different species of insects. PMID:10937252

Shonle, I; Bergelson, J



An iminophosphorane-mediated efficient synthesis of the alkaloid eudistomin U of marine origin  

Microsoft Academic Search

The first synthesis of the alkaloid eudistomin U, by a four-step sequence is described. The key step, formation of the ?-carboline ring, involves a tandem aza Wittig \\/ electrocyclic ring closure process.

Pedro Molina; Pilar M. Fresneda; Sagrario García-Zafra



Eudistomin U and isoeudistomin U, new alkaloids from the Caribbean ascidian Lissoclinum fragile.  


Chemical investigations of the Caribbean ascidian Lissoclinum fragile (Didemnidae) have resulted in the isolation of new alkaloids which we have designated eudistomin U [1] and isoeudistomin U [2]. Their structures were determined by spectrometric and chemical means. PMID:8021654

Badre, A; Boulanger, A; Abou-Mansour, E; Banaigs, B; Combaut, G; Francisco, C



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


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



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

Microsoft Academic Search

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

Martina Herrmann; Holger Joppe; Gerhard Schmaus



Differential effect of the benzophenanthridine alkaloids sanguinarine and chelerythrine on glycine transporters.  


Glycine transporter inhibitors modulate the transmission of pain signals. Since it is well known that extracts from medicinal plants such as Chelidonium majus exhibit analgesic properties, we investigated the effects of alkaloids typically present in this plant on glycine transporters. We found that chelerythrine and sanguinarine selectively inhibit the glycine transporter GlyT1 with comparable potency in the low micromolar range while berberine shows no inhibition at all. At this concentration both alkaloids only minimally affected transport of the closely related glycine transporter GlyT2, suggesting that the effect is not mediated by the inhibitory activity of these alkaloids on the Na(+)/K(+) ATPase. GlyT1 inhibition was time-dependent, noncompetitive and increased with glycine concentration. While chelerythrine inhibition was reversible, the effect of sanguinarine was resistant to wash out. These results suggest that benzophenanthridine alkaloids interact with glycine transporters and at low micromolar range selectively target glycine transporter GlyT1. PMID:21315125

Jursky, Frantisek; Baliova, Martina



Copper-catalyzed arylation of o-bromoanilides: highly flexible synthesis of hexahydropyrroloindole alkaloids.  


In the presence of catalytic amount of copper iodide, a remote amide-assisted intramolecular arylation followed by alkylation leads to a general and flexible synthetic method toward the synthesis of medicinally interesting hexahydropyrroloindole alkaloids. PMID:22667443

Zhou, Yongyun; Xi, Yongkai; Zhao, Jingfeng; Sheng, Xianfu; Zhang, Shuqin; Zhang, Hongbin



[Effect of processing on the alkaloids in Strychnos nux-vomica L].  


The contents of strychnine, brucine, isostrychnine and isobrucine in different processed products of Strychnos nux-vomica were determined by TLC-densitometry. The relationship of the contents of strychnos alkaloids with processing methods was studied. PMID:7945866

Wu, H; Cai, B C; Zheng, P X; Zhao, C Z; Yuan, Z R



The first synthesis of the pentacyclic pyridoacridine marine alkaloids: arnoamines A and B.  


The synthesis of the marine pyridoacridine alkaloids arnoamines A and B has been accomplished in six and seven steps from 4-chloro-8-methoxy-5-nitroquinoline in 13% and 4% overall yield, respectively. PMID:10970284

Delfourne, E; Roubin, C; Bastide, J



Structures and antimicrobial activities of pyridoacridine alkaloids isolated from different chromotypes of the ascidian Cystodytes dellechiajei.  


Three new pentacyclic alkaloids were isolated from different chromotypes of the western Mediterranean ascidian Cystodytes dellechiajei. The purple color morph collected in Catalonia contained the known compounds kuanoniamine D (1), shermilamine B (2), N-deacetylkuanoniamine D (3), and styelsamine C (4) and a new alkaloid named N-deacetylshermilamine B (5). The green color morph collected in the Balearic Islands contained the known compounds 11-hydroxyascididemin (6) and 8,9-dihydro-11-hydroxyascididemin (7) and two new alkaloids named cystodimine A (8) and cystodimine B (9). The blue color morph collected in Catalonia yielded the known compound ascididemin (10). The structures of all compounds were elucidated on the basis of spectroscopic data, mainly 1D and 2D NMR data. The antimicrobial potential of the pyridoacridine alkaloids isolated from each color morph was evaluated and compared. PMID:20491501

Bontemps, N; Bry, D; López-Legentil, S; Simon-Levert, A; Long, C; Banaigs, B



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

NASA Astrophysics Data System (ADS)

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

Rogers, Kevin; Milnes, John; Gormally, John



The Structure of Ipalbine, a New Hexahydroindolizine Alkaloid, Isolated from Ipomoea Alba L..  

National Technical Information Service (NTIS)

Recent phytochemical studies have shown that the seeds of several members of the Convolvulaceae family, in particular certain Rivea, Ipomoea, and Argyreia species contain significant amounts of ergoline alkaloids. The isolation and structural determinatio...

J. M. Gourley R. A. Heacock A. G. McInnes B. Nikolin D. G. Smith



Desoxoprosopinine: A Model for the Total Asymmetric Synthesis of Prosopis Alkaloids.  

National Technical Information Service (NTIS)

This work develops a general synthesis of the Prosopis africana alkaloids, using a chiral auxiliary-mediated process. Enantiopure N- acyldihydropyridones were produced and used as intermediates, targeting (+)- desoxoprosopinine as a synthetic model for th...

M. J. Sandelier



Recent Progress in the Metabolic Engineering of Alkaloids in Plant Systems  

PubMed Central

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

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



Quantitative analysis of alkaloidal constituents in imported fire ants by gas chromatography.  


A method based on silica gel chromatography and GC-MS/GC-FID analyses was developed for the quantitation of alkaloidal compounds in imported fire ants, Solenopsis richteri, S. invicta, and their hybrid found in the southern United States. The cis and trans alkaloids from fire ant body extracts were successfully separated by silica gel chromatography, identified by GC-MS, and quantitated by GC-FID. Piperideine compounds were eluted together with the cis and trans piperidines, but were well-resolved on a nonpolar GC column. Eight pairs of piperidine isomers and 12 piperideines were quantitated. The ratios of trans alkaloids to corresponding cis isomers ranged from 87 to 378:1 in S. invicta and were significantly higher than in S. richteri and hybrid ants. The results were discussed in relation to the evolution of fire ant venom alkaloids and their role as host location cues for parasitic Pseudacteon phorid flies. PMID:24873743

Yu, Yu-Ting; Wei, Hong-Yi; Fadamiro, Henry Y; Chen, Li



Effects of phthalimide on growth and alkaloid formation of Datura metel L  

Microsoft Academic Search

Summary When administered toDatura metel L. by foliar or root application, the new plant growth regulator phthalimide exercises a favorable effect on the vegetative growth and also stimulates the formation of tropane alkaloids.

M. P. Fasulo; A. M. Forestieri; E. M. Galati; G. Tumino




Microsoft Academic Search

Some endophytes in mutualistic associations with Festuca, Lolium and other grass species produce insecticidal loline alkaloids (1-aminopyrrolizidines; LA). These loline alkaloids have a saturated pyrrolizidine ring system (two-rings sharing a carbon and nitrogen atom), a 1-amine substituted with methyl, acetyl, or formyl groups, and an oxygen bridge between C-2 and C-7. The development of a reliable system of production of

Jimmy Douglas Blankenship



A new quaternary protoberberine alkaloid isolated from Dicranostigma leptopodum (Maxim) Fedde.  


Phytochemical investigation of the whole plants of Dicranostigma leptopodum (Maxim) Fedde has led to the isolation of two quaternary protoberberine alkaloids 5-hydroxy-coptisine (1) and berberrubine (2). This type of alkaloids was isolated from the genus Dicranostigma for the first time and the new compound structure (1) was elucidated by various spectroscopic methods including 2D NMR techniques (gCOSY, HMQC and HMBC) and HR-ESI-MS. PMID:24499388

Zhong, Mei; Ma, Yu-Xi; Liu, Jun-Xi; Di, Duo-Long



Biophysical aspects and biological implications of the interaction of benzophenanthridine alkaloids with DNA  

Microsoft Academic Search

Benzophenanthridine alkaloids represent a very interesting and significant group of natural products that exhibit a broad\\u000a range of biological and pharmacological properties. Among this group of alkaloids, sanguinarine, nitidine, fagaronine, and\\u000a chelerythrine have the potential to form molecular complexes with DNA structures and have attracted recent attention for their\\u000a possible clinical and pharmacological utility. This review focuses on the interaction

Motilal Maiti; Gopinatha Suresh Kumar



Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida  

Microsoft Academic Search

Two new alkaloids, hypserpanines A and B (1, 11), together with eleven known compounds, phenolbetain (2), acutumine (3), acutumidine (4), dechloroacutumine (5), dauricumine (6), dauricumidine (7), pronuciferine (8), glaziovine (9), S-reticuline (10), magnoflorine (12) and laurifoline(13), were isolated from Hypserpa nitida Miers. (Menispermaceae) and chemically elucidated through spectral analyses. All the isolated alkaloids were evaluated for their anti-HBV activities in

Pi Cheng; Yun-bao Ma; Shu-ying Yao; Quan Zhang; En-jun Wang; Meng-hong Yan; Xue-mei Zhang; Feng-xue Zhang; Ji-jun Chen



A benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial activity  

Microsoft Academic Search

A benzoisofuranone derivative, 3?-(1?-hydroxyethyl)-7-hydroxy-1-isobenzofuranone, and a dimeric carbazole alkaloid, 3,3?-[oxybis(methylene)]bis(9-methoxy-9H-carbazole), along with six known carbazole alkaloids and three known steroids were isolated from the stem bark of Murraya koenigii. The structures of these compounds were established unambiguously by UV, IR, MS and a series of 1D and 2D NMR analyses. The minimum inhibitory concentrations (MIC) of these compounds were found

M. Mukhlesur Rahman; Alexander I. Gray



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.

Sacher, Joshua R.; Weinreb, Steven M.



Alkaloids and ascidian chemical defense: Evidence for the ecological role of natural products from Eudistoma olivaceum  

Microsoft Academic Search

The surface of the colonial ascidianEudistoma olivaceum (Van Name) is almost completely free of fouling organisms. I provide evidence that this epibiont-free surface is maintained by the alkaloids, Eudistomins G and H. These alkaloids were extracted from colonies collected in the shallow subtidal of Indian River Lagoon, Florida. USA, in November 1987. Concentrations of less than one-fifth of those found

A. R. Davis



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

Microsoft Academic Search

The N-oxides of pyrrolizidine alkaloids such as senecionine or monocrotaline are rapidly taken up and accumulated by cell suspension cultures obtained from plants known to produce pyrrolizidines, i.e. Senecio vernalis, vulgaris, viscosus (Asteraceae) and Symphytum officinale (Boraginaceae). The transport of the N-oxides into the cells is a specific and selective process. Other alkaloid N-oxides such as sparteine N-oxide are not

Kirsten Borstel; Thomas Hartmann



Production of steroidal alkaloids by hairy roots of Solanum aviculare and the effect of gibberellic acid  

Microsoft Academic Search

Cultures of Solanum aviculare hairy roots were established after transformation with Agrobacterium rhizogenes A4. High levels of steroidal alkaloids measured as solasodine equivalents were produced in shake-flasks and bioreactor, even though relatively low concentrations are found in roots in vivo. In shake flasks the maximum alkaloid yield was 32 mg g-1 dry weight; in a 3-1 air-driven bioreactor the yield

M. Ahkam Subroto; Pauline M. Doran



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

PubMed Central

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

Cheng, Xiayun; Waters, Stephen P.



Nordehydrocyclodercitin, a hexacyclic pyridoacridine alkaloid from the marine ascidian, Aplidium sp.  


A new hexacyclic pyridoacridine alkaloid, nordehydrocyclodercitin (1), from an ascidian, Aplidium sp., cf. Aplidium cratiferum collected at Arab Reef, Great Barrier Reef, Australia is reported. Nordehydrocyclodercitin is structurally related to stellettamine (2) and cyclodercitin (3), which are sponge metabolites, and cycloshermilamine D (4) which was isolated from the marine tunicate Cystodytes violatinctus. The structure of nordehydrocyclodercitin was determined by interpretation of spectroscopic data, particularly those obtained from HMBC correlations, and by comparison with reported data for known related pyridoacridine alkaloids. PMID:17763101

Agrawal, Madhavi S; Bowden, Bruce F



Screening species of Pilocarpus (Rutaceae) as sources of pilocarpine and other imidazole alkaloids  

Microsoft Academic Search

Plants of the Pilocarpus genus (Rutaceae) are popularly known as jaborandi and are the only source of pilocarpine, an imidazole alkaloid used in eye-drops for the treatment of glaucoma as well as\\u000a for the stimulation of sweat and lachrymal glands. Alkaloid extracts from leaf samples of seven species of Pilocarpus, from the states of Săo Paulo and Maranhăo in Brazil,

Alexandra Christine Helena Frankland Sawaya; Boniek Gontijo Vaz; Marcos Nogueira Eberlin; Paulo Mazzafera



Direct analysis of aromatic diene Erythrina alkaloids by capillary GC-MS  

Microsoft Academic Search

Alkaloids extracted from Erythrina crista-galli seedlings by 0.025 M HCl were resolved, without prior derivatization, by capillary gas chromatography-mass spectrometry. 8-oxo-Erythraline, erythraline, erysotrine and crystamidine, in deceasing order of abundance, were recognized by their EI-mass spectral fragmentation pattern. Applying the technique to E. pallida, erysotrine was the principal alkaloid in seed, and seedling leaves contained 8-oxo-erythraline, erysotrine, erythraline and erysovine.

Peter G. Mantle



Measurement of antiphotooxidative properties of isoquinoline alkaloids using transient thermal lens spectroscopy  

NASA Astrophysics Data System (ADS)

The antiphotooxidative properties of boldine and chloride berberine were studied by time-resolved thermal lensing technique. These compounds belong to isoquinoline alkaloids possessing interesting biological activity (e.g. antibacterial, antimalarial, antitumor). Antiphotooxidative properties of the alkaloids were studied by mechanism of energy transference between powerful oxidizing agents such as singlet oxygen. Singlet oxygen was produced by energy transfer from chlorophyll-sensitized photooxidation of oil by exposure of high light intensities like laser. The lifetimes of singlet oxygen in dimethylsulfoxide, methanol and water were determined to confirm the assignment of the singlet molecular oxygen O II (1? g) in the experiments. In order to understand the effect of the alkaloids on active oxygen species, we carried out in detail an analysis of the thermal lensing signal. It was shown that the alkaloids can act as quenchers of singlet oxygen. To demonstrate the ability of the alkaloids to act efficient singlet oxygen acceptors, we have measured the fluorescence spectra of the studied alkaloids in the presence and in the absence of singlet oxygen. The antiphotooxidative activity of boldine and chloride berberine can be explained by the ability to quench singlet oxygen.

Hung, J.; Castillo, J.; Laboren, I.; Rodríguez, M.; Hassegawa, M.



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


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



Effects of different elicitors on yield of tropane alkaloids in hairy roots of Anisodus acutangulus.  


The four tropane alkaloids have played a pivotal role in controlling diseases such as the toxic and septic shock, the organophosphorus poison and the acute lung injury. Here, the elicitation effect of different elicitors on the production of tropane alkaloids and the molecular mechanism of enzyme genes in the pathway was firstly demonstrated in hairy roots of Anisodus acutangulus. The results showed ethanol, methyl jasmonate and Ag(+) could improve the accumulation of tropane alkaloids up to 1.51, 1.13 and 1.08 times after 24 h treatment, respectively (P < 0.05), whereas salicylic acid decreased the average content of tropane alkaloids. Furthermore, expression profile analysis results revealed that up-regulation of hyoscyamine-6b-hydroxylase (AaH6H) and little regulation of tropinone reducase II (AaTR2) elicited by ethanol, increased expression of putrescine N-methyltransferase I (AaPMT1) elicited by Ag(+), elevated expression of tropinone reducase I (AaTR1) elicited by methyl jasmonate, respectively, resulted in tropane alkaloids improvement. Our results showed that hairy root culture of A. acutangulus in combination with elicitors was a promising way for production of tropane alkaloids in the future. PMID:21625855

Kai, Guoyin; Yang, Sheng; Zhang, Yan; Luo, Xiuqin; Fu, Xueqing; Zhang, Ang; Xiao, Jianbo



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.

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



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.

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



Identification and quantification of hepatotoxic pyrrolizidine alkaloids in the Ethiopian medicinal plant Solanecio gigas (Asteraceae).  


The pyrrolizidine alkaloid content of Solanecio gigas (Vatke) C. Jeffrey (Asteraceae), an Ethiopian medicinal plant widely used for the treatment of colic, diarrhea, gout, otitis media, typhoid fever, and noted for its wound dressing and antiabortifacient activities was studied. The flower and leaf extracts contained 0.19% and 0.14% alkaloids (dry weight), respectively. GLC-MS analysis indicated that all the alkaloids in the flowers are pyrrolizidine alkaloids (PAs), whereas the leaves contain other type of alkaloids with PAs occurring in low concentrations. Roughly, 80% and 90% of the total PAs in the flowers and the leaves, respectively, were shown to occur as N-oxides. Eighteen alkaloids were detected in the flower extract with the retronecine type twelve-membered macrocyclic diesters integerrimine, senecionine and usaramine comprising 82% of the total PA content. Analysis of the PA profile of the leaves indicated that it has a simpler pattern than the one observed for the flowers. Only five PAs were detected in the leaves with integerrimine making up about 50% of the total PAs. Quantification of the PA content by GLC showed that the flowers and leaves contain 3321.21 and 84.84 microg per 10 g of dried plant material, respectively. These results indicate that users of this herb are at high risk of poisoning since the most toxic twelve membered macrocyclics of the retronecine type are the dominant PAs in the plant. PMID:17944327

Asres, K; Sporer, F; Wink, M



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


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



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


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



Comparative study of fourteen alkaloids from Uncaria rhynchophylla hooks and leaves using HPLC-diode array detection-atmospheric pressure chemical ionization/MS method.  


The purpose of the study is to compare alkaloid profile of Uncaria rhynchophylla hooks and leaves. Ten oxindole alkaloids and four glycosidic indole alkaloids were identified using HPLC-diode array detection (DAD) or LC-atmospheric pressure chemical ionization (APCI)-MS method, and a HPLC-UV method for simultaneous quantification of major alkaloids was validated. The hooks are characterized by high levels of four oxindole alkaloids rhynchophylline (R), isorhynchophylline (IR), corynoxeine (C) and isocorynoxeine (IC), while the leaves contained high level of two glycosidic indole alkaloids vincoside lactam (VL) and strictosidine (S). The presented methods have proven its usefulness in chemical characterization of U. rhynchophylla hooks and leaves. PMID:22223371

Qu, Jialin; Gong, Tianxing; Ma, Bin; Zhang, Lin; Kano, Yoshihiro; Yuan, Dan



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



Voatinggine and tabertinggine, pentacyclic indole alkaloids derived from an iboga precursor via a common cleavamine-type intermediate.  


Two new indole alkaloids, voatinggine (1) and tabertinggine (2), which are characterized by previously unencountered natural product skeletons, were isolated from a Malayan Tabernaemontana species. The structures and absolute configuration of these alkaloids were determined using NMR and MS analysis, and X-ray diffraction analysis. A possible biogenetic pathway to these novel alkaloids from an iboga precursor, and via a common cleavamine-type intermediate, is presented. PMID:23991636

Nge, Choy-Eng; Gan, Chew-Yan; Low, Yun-Yee; Thomas, Noel F; Kam, Toh-Seok



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

Microsoft Academic Search

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

Jian Zhao; Robert Verpoorte



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



Evidence of maternal provisioning of alkaloid-based chemical defenses in the strawberry poison frog Oophaga pumilio.  


Many organisms use chemical defenses to reduce predation risk. Aposematic dendrobatid frogs sequester alkaloid-based chemical defenses from a diet of arthropods, but research on these defenses has been limited to adults. Herein, we investigate chemical defense across development in a dendrobatid frog, Oophaga pumilio. This species displays complex parental care: at hatching, mothers transport tadpoles to phytotelmata, and then return to supply them with an obligate diet of nutritive eggs for about six weeks. We collected eggs, tadpoles, juveniles, and adults of O. pumilio, and detected alkaloids in all life stages. The quantity and number of alkaloids increased with frog and tadpole size. We did not detect alkaloids in the earliest stage of tadpoles, but alkaloids were detected as trace quantities in nutritive eggs and as small quantities in ovarian eggs. Tadpoles hand-reared with eggs of an alkaloid-free heterospecific frog did not contain alkaloids. Alkaloids that are sequestered from terrestrial arthropods were detected in both adults and phytotelm-dwelling tadpoles that feed solely on nutritive eggs, suggesting that this frog may be the first animal known to actively provision post-hatch offspring with chemical defenses. Finally, we provide experimental evidence that maternally derived alkaloids deter predation of tadpoles by a predatory arthropod. PMID:24804437

Stynoski, Jennifer L; Torres-Mendoza, Yaritbel; Sasa-Marin, Mahmood; Saporito, Ralph A



Antiplasmodial and antioxidant isoquinoline alkaloids from Dehaasia longipedicellata.  


The crude extract of the bark of Dehaasia longipedicellata exhibited antiplasmodial activity against the growth of Plasmodium falciparum K1 isolate (resistant strain). Phytochemical studies of the extract led to the isolation of six alkaloids: two morphinandienones, (+)-sebiferine (1) and (-)-milonine (2); two aporphines, (-)-boldine (3) and (-)-norboldine (4); one benzlyisoquinoline, (-)-reticuline (5); and one bisbenzylisoquinoline, (-)-O-O-dimethylgrisabine (6). Their structures were determined on the basis of 1D and 2D?NMR, IR, UV, and LCMS spectroscopic techniques and upon comparison with literature values. Antiplasmodial activity was determined for all of the isolated compounds. They showed potent to moderate activity with IC50 values ranging from 0.031 to 30.40?µM. (-)-O-O-dimethylgrisabine (6) and (-)-milonine (2) were the two most potent compounds, with IC50 values of 0.031 and 0.097?µM, respectively, that were comparable to the standard, chloroquine (0.090?µM). The compounds were also assessed for their antioxidant activities with di(phenyl)-(2,4,6-trinitrophenyl)iminoazanium (IC50?=?18.40-107.31?µg/mL), reducing power (27.40-87.40?%), and metal chelating (IC50?=?64.30 to 257.22?µg/mL) having good to low activity. (-)-O-O-dimethylgrisabine (6) exhibited a potent antioxidant activity of 44.3?% reducing power, while di(phenyl)-(2,4,6-trinitrophenyl)iminoazanium and metal chelating activities had IC50 values of 18.38 and 64.30?µg/mL, respectively. Thus it may be considered as a good reductant with the ability to chelate metal and prevent pro-oxidant activity. In addition to the antiplasmodial and antioxidant activities, the isolated compounds were also tested for their cytotoxicity against a few cancer and normal cell lines. (-)-Norboldine (4) exhibited potent cytotoxicity towards pancreatic cancer cell line BxPC-3 with an IC50 value of 27.060?±?1.037?µM, and all alkaloids showed no toxicity towards the normal pancreatic cell line (hTERT-HPNE). PMID:24723007

Zahari, Azeana; Cheah, Foo Kit; Mohamad, Jamaludin; Sulaiman, Syazreen Nadia; Litaudon, Marc; Leong, Kok Hoong; Awang, Khalijah



The Only African Wild Tobacco, Nicotiana africana: Alkaloid Content and the Effect of Herbivory  

PubMed Central

Herbivory in some Nicotiana species is known to induce alkaloid production. This study examined herbivore-induced defenses in the nornicotine-rich African tobacco N. africana, the only Nicotiana species indigenous to Africa. We tested the predictions that: 1) N. africana will have high constitutive levels of leaf, flower and nectar alkaloids; 2) leaf herbivory by the African bollworm Helicoverpa armigera will induce increased alkaloid levels in leaves, flowers and nectar; and 3) increased alkaloid concentrations in herbivore-damaged plants will negatively affect larval growth. We grew N. africana in large pots in a greenhouse and exposed flowering plants to densities of one, three and six fourth-instar larvae of H. armigera, for four days. Leaves, flowers and nectar were analyzed for nicotine, nornicotine and anabasine. The principal leaf alkaloid was nornicotine (mean: 28 µg/g dry mass) followed by anabasine (4.9 µg/g) and nicotine (0.6 µg/g). Nornicotine was found in low quantities in the flowers, but no nicotine or anabasine were recorded. The nectar contained none of the alkaloids measured. Larval growth was reduced when leaves of flowering plants were exposed to six larvae. As predicted by the optimal defense theory, herbivory had a localized effect and caused an increase in nornicotine concentrations in both undamaged top leaves of herbivore damaged plants and herbivore damaged leaves exposed to one and three larvae. The nicotine concentration increased in damaged compared to undamaged middle leaves. The nornicotine concentration was lower in damaged leaves of plants exposed to six compared to three larvae, suggesting that N. africana rather invests in new growth as opposed to protecting older leaves under severe attack. The results indicate that the nornicotine-rich N. africana will be unattractive to herbivores and more so when damaged, but that potential pollinators will be unaffected because the nectar remains alkaloid-free even after herbivory.

Marlin, Danica; Nicolson, Susan W.; Yusuf, Abdullahi A.; Stevenson, Philip C.; Heyman, Heino M.; Kruger, Kerstin



The Only African Wild Tobacco, Nicotiana africana: Alkaloid Content and the Effect of Herbivory.  


Herbivory in some Nicotiana species is known to induce alkaloid production. This study examined herbivore-induced defenses in the nornicotine-rich African tobacco N. africana, the only Nicotiana species indigenous to Africa. We tested the predictions that: 1) N. africana will have high constitutive levels of leaf, flower and nectar alkaloids; 2) leaf herbivory by the African bollworm Helicoverpa armigera will induce increased alkaloid levels in leaves, flowers and nectar; and 3) increased alkaloid concentrations in herbivore-damaged plants will negatively affect larval growth. We grew N. africana in large pots in a greenhouse and exposed flowering plants to densities of one, three and six fourth-instar larvae of H. armigera, for four days. Leaves, flowers and nectar were analyzed for nicotine, nornicotine and anabasine. The principal leaf alkaloid was nornicotine (mean: 28 µg/g dry mass) followed by anabasine (4.9 µg/g) and nicotine (0.6 µg/g). Nornicotine was found in low quantities in the flowers, but no nicotine or anabasine were recorded. The nectar contained none of the alkaloids measured. Larval growth was reduced when leaves of flowering plants were exposed to six larvae. As predicted by the optimal defense theory, herbivory had a localized effect and caused an increase in nornicotine concentrations in both undamaged top leaves of herbivore damaged plants and herbivore damaged leaves exposed to one and three larvae. The nicotine concentration increased in damaged compared to undamaged middle leaves. The nornicotine concentration was lower in damaged leaves of plants exposed to six compared to three larvae, suggesting that N. africana rather invests in new growth as opposed to protecting older leaves under severe attack. The results indicate that the nornicotine-rich N. africana will be unattractive to herbivores and more so when damaged, but that potential pollinators will be unaffected because the nectar remains alkaloid-free even after herbivory. PMID:25025217

Marlin, Danica; Nicolson, Susan W; Yusuf, Abdullahi A; Stevenson, Philip C; Heyman, Heino M; Krüger, Kerstin



Mutation in the Plasmodium falciparum CRT Protein Determines the Stereospecific Activity of Antimalarial Cinchona Alkaloids  

PubMed Central

The Cinchona alkaloids are quinoline aminoalcohols that occur as diastereomer pairs, typified by (?)-quinine and (+)-quinidine. The potency of (+)-isomers is greater than the (?)-isomers in vitro and in vivo against Plasmodium falciparum malaria parasites. They may act by the inhibition of heme crystallization within the parasite digestive vacuole in a manner similar to chloroquine. Earlier studies showed that a K76I mutation in the digestive vacuole-associated protein, PfCRT (P. falciparum chloroquine resistance transporter), reversed the normal potency order of quinine and quinidine toward P. falciparum. To further explore PfCRT-alkaloid interactions in the malaria parasite, we measured the in vitro susceptibility of eight clonal lines of P. falciparum derived from the 106/1 strain, each containing a unique pfcrt allele, to four Cinchona stereoisomer pairs: quinine and quinidine; cinchonidine and cinchonine; hydroquinine and hydroquinidine; 9-epiquinine and 9-epiquinidine. Stereospecific potency of the Cinchona alkaloids was associated with changes in charge and hydrophobicity of mutable PfCRT amino acids. In isogenic chloroquine-resistant lines, the IC50 ratio of (?)/(+) CA pairs correlated with side chain hydrophobicity of the position 76 residue. Second-site PfCRT mutations negated the K76I stereospecific effects: charge-change mutations C72R or Q352K/R restored potency patterns similar to the parent K76 line, while V369F increased susceptibility to the alkaloids and nullified stereospecific differences between alkaloid pairs. Interactions between key residues of the PfCRT channel/transporter with (?) and (+) alkaloids are stereospecifically determined, suggesting that PfCRT binding plays an important role in the antimalarial activity of quinine and other Cinchona alkaloids.

Griffin, Carol E.; Hoke, Jonathan M.; Samarakoon, Upeka; Duan, Junhui; Mu, Jianbing; Ferdig, Michael T.; Warhurst, David C.



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

PubMed Central

The evolution of cactophily in the genus Drosophila was a major ecological transition involving over a hundred species in the Americas that acquired the capacity to cope with a variety of toxic metabolites evolved as feeding deterrents in Cactaceae. D. buzzatii and D. koepferae are sibling cactophilic species in the D. repleta group. The former is mainly associated with the relatively toxic-free habitat offered by prickly pears (Opuntia sulphurea) and the latter has evolved the ability to use columnar cacti of the genera Trichocereus and Cereus that contain an array of alkaloid secondary compounds. We assessed the effects of cactus alkaloids on fitness-related traits and evaluated the ability of D. buzzatii and D. koepferae to exploit an artificial novel toxic host. Larvae of both species were raised in laboratory culture media to which we added increasing doses of an alkaloid fraction extracted from the columnar cactus T. terschekii. In addition, we evaluated performance on an artificial novel host by rearing larvae in a seminatural medium that combined the nutritional quality of O. sulphurea plus amounts of alkaloids found in fresh T. terschekii. Performance scores in each rearing treatment were calculated using an index that took into account viability, developmental time, and adult body size. Only D. buzzatii suffered the effects of increasing doses of alkaloids and the artificial host impaired viability in D. koepferae, but did not affect performance in D. buzzatii. These results provide the first direct evidence that alkaloids are key determinants of host plant use in these species. However, the results regarding the artificial novel host suggest that the effects of alkaloids on performance are not straightforward as D. koepferae was heavily affected. We discuss these results in the light of patterns of host plan evolution in the Drosophila repleta group.

Soto, Ignacio M.; Carreira, Valeria P.; Corio, Cristian; Padro, Julian; Soto, Eduardo M.; Hasson, Esteban



Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models.  


Alkaloids from the plant family of Amaryllidaceae, such as galantamine (GAL) and lycorine (LYC), are known to exhibit numerous promising biological and pharmacological activities like antibacterial, antiviral or anti-inflammatory effects. Nonetheless, studies on the biotransformation pathway are rare for this substance class, unless approval for use as medication exists. While GAL has become a prescription drug used to alleviate and delay the symptoms of Alzheimer's disease, LYC exhibits potential antitumor properties. However, it has also been linked to toxic effects resulting in nausea and emesis. Whereas there are few publications available describing the metabolic pathway of GAL in animals and humans, the metabolism of LYC is unknown. Therefore, this study is concerned with the investigation of the oxidative metabolism of GAL and LYC, which was achieved by means of three different approaches: electrochemical (EC) simulation coupled on-line to liquid chromatography (LC) with electrospray mass spectrometric (ESI-MS) detection was applied in addition to in vivo experiments in beagle dog analyzing plasma (BP) and in vitro incubations with rat liver microsomes (RLM). This way, it should be investigated if electrochemistry can be used to predict the oxidative metabolism of alkaloids. For GAL, the EC model was capable of predicting most metabolites observed during microsomal and plasma studies, including N-demethylated, dehydrogenated and oxygenated products or a combination of these. LYC was found to be metabolized far less than GAL in the animal-based approaches, but several EC oxidation products were generated. Some principal metabolic routes could successfully be correlated for this alkaloid as well, comprising dehydrogenation, dehydration to ungeremine and oxygenation reactions. PMID:23176740

Jahn, Sandra; Seiwert, Bettina; Kretzing, Sascha; Abraham, Getu; Regenthal, Ralf; Karst, Uwe



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


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



Sesquiterpenes and alkaloids from the roots of Alangium chinense.  


Four new sesquiterpenes (1-4), four new alkaloids (5a, 6a, 6b, and 7), and nine known compounds (5b and 8-15) were isolated from an ethanolic extract of roots of Alangium chinense. The structure of 1 was confirmed by X-ray crystallography. The configurations of 5 and 6 were assigned by chiral HPLC analysis and CD spectra. Compounds 3, 4, 8-13, and 15 exhibited antiviral activity against Coxsackie virus B3 with IC50 values of 1.4-15.4 ?M. Compounds 2-4, 7, and 9-13 showed antioxidant activities against Fe(2+)-cysteine-induced rat liver microsomal lipid peroxidation, with IC50 values of 3.8-45.7 ?M. Compound 5b displayed neuritis inhibitory activity against microglial inflammation factor, with an IC50 value of 6.7 ?M. None of the compounds exhibited detectable cytotoxic activity toward any of five tumor cell lines (A549, Be-17402, BGC-823, HCT-8, and A2780) in the MTT assay. PMID:23734721

Zhang, Yan; Liu, Yun-Bao; Li, Yong; Ma, Shuang-Gang; Li, Li; Qu, Jing; Zhang, Dan; Chen, Xiao-Guang; Jiang, Jian-Dong; Yu, Shi-Shan



Pumiliotoxin alkaloids: a new class of sodium channel agents.  


Pumiliotoxin B (PTX-B) and a variety of congeneric alkaloids and synthetic analogs stimulated sodium flux and phosphoinositide breakdown in guinea pig cerebral cortical synaptoneurosomes. The effects of PTX-B and active congeners and analogs on sodium flux in synaptoneurosomes were potentiated markedly by scorpion venom (Leiurus quinquestriatus). In neuroblastoma cells, PTX-B and active congeners had no effect on sodium flux unless synergized by alpha-scorpion toxin or scorpion venom. Certain inactive congeners, lacking hydroxyl groups in the 6-alkylidene side chain, inhibited sodium flux elicited by PTX-B, scorpion venom, or the sodium channel activator batrachotoxin. Such inhibition appeared different from inhibition by local anesthetics, since pumiliotoxins, unlike local anesthetics, had little or no effect on binding of [3H]batrachotoxinin A benzoate to sodium channels. Thus, it appears likely that some "inactive" congeners bind to the PTX-B binding site, but do not activate sodium channels. In the absence of scorpion venom the stimulation of phosphoinositide breakdown in synaptoneurosomes was consonant with the stimulatory effects of these compounds on sodium flux through voltage-dependent sodium channels. PMID:2165404

Daly, J W; Gusovsky, F; McNeal, E T; Secunda, S; Bell, M; Creveling, C R; Nishizawa, Y; Overman, L E; Sharp, M J; Rossignol, D P



Cytotoxic Epipolythiodioxopiperazine Alkaloids from Filamentous Fungi of the Bionectriaceae  

PubMed Central

Bioactivity-directed fractionation of the organic extracts of two filamentous fungi of the Bionectriaceae, strains MSX 64546 and MSX 59553 from the Mycosynthetix library, led to the isolation of a new dimeric epipolythiodioxopiperazine alkaloid, verticillin H (1), along with six related analogues, Sch 52900 (2), verticillin A (3), gliocladicillin C (4), Sch 52901 (5), 11?-deoxyverticillin A (6), and gliocladicillin A (7). The structures of compounds 1–7 were determined by extensive NMR and HRMS analyses, as well as by comparisons to the literature. All compounds (1–7) were evaluated for cytotoxicity against a panel of human cancer cell lines, displaying IC50 values ranging from 1.2 µM to 10 nM. Compounds 1–5 were examined for activity in the NF-?B assay, where compounds 2 and 3 revealed activity in the sub-micromolar range. Additionally, compounds 1, 3, and 4 were tested for EGFR inhibition using an enzymatic assay, while compound 3 was examined against an overexpressing EGFR+ve cancer cell line.

Figueroa, Mario; Graf, Tyler N.; Ayers, Sloan; Adcock, Audrey F.; Kroll, David J.; Yang, Jilai; Swanson, Steven M.; Munoz-Acuna, Ulyana; Carcache de Blanco, Esperanza J.; Agrawal, Rajesh; Wani, Mansukh C.; Darveaux, Blaise A.; Pearce, Cedric J.; Oberlies, Nicholas H.



New lamellarin alkaloids from the australian ascidian, didemnum chartaceum  


Five novel lamellarin-class alkaloids have been isolated from a Great Barrier Reef ascidian, Didemnum chartaceum. The structures of the 20-sulfated derivatives of lamellarins B, C, and L (1-3); the 8-sulfated derivative of lamellarin G (4), plus a nonsulfated compound, lamellarin Z (5), were identified by interpretation of spectroscopic data. Lamellarin G 8-sulfate (4) is the first example of this class of compounds sulfated at the C-8 position, while lamellarin Z (5) is the first example of a dimethoxylated lamellarin. The known lamellarins A, B, C, E, G, and L (6-11), plus the triacetate derivatives of lamellarins D (12) and N (13), were also isolated. An aberration in the integration of signals in the 1H NMR spectra of the 20-sulfated derivatives of lamellarins B, C, and L (1-3) led to NMR relaxation studies. T1 values were calculated for all protons in the sulfated lamellarins (1-4) and their corresponding nonsulfated derivatives (7, 8, 10, 11). Interestingly, the protons ortho to the sulfate group in compounds (1-4) had T1 values up to five times larger than the corresponding protons in their nonsulfated derivatives (7, 8, 10, 11). PMID:10096849

Davis; Carroll; Pierens; Quinn



Datura metel: in vitro production of tropane alkaloids.  


Hairy root lines of Datura metel were established following infection of aseptic stem segments with Agrobacterium rhizogenes strain A4 and cultured in hormone-free B5 solid medium. The growth and production of hyoscyamine and scopolamine (mg/g dry wt.) of these root cultures was encouraged by using B5 liquid medium with half-strength salts. In these culture conditions, the capacity of the highest productive root line 25 to excrete scopolamine into the culture medium rose from 8.7% to 70% when the permeabilizing agent Tween 20 was added for 24 h to the medium, after 2 and 4 weeks of culture. Using an airlift bioreactor (41) with modifications in order to increase root anchorage, the Tween 20 treatment encouraged both growth and alkaloid productivity of cultured root line 25. After 4 weeks their biomass yield was 2.3 mg/l/day and 0.84 mg/l/day of scopolamine was produced (70% extracellular). The scopolamine released into the culture medium was separated with an Amberlite XAD-2 column located in the media exit. PMID:10193206

Cusido, R M; Palazón, J; Pińol, M T; Bonfill, M; Morales, C



Genotypes and alkaloid contents of Datura metel varieties.  


Datura metel L. var. muricata (BERNH.) DANERT was found to be double recessive with respect to the genes concerning the color and form of the corolla by breeding experiments involving four varieties, i.e. var. metel (white, simple corolla), var. rubra (purple, simple), var. fastuosa (purple, double or triple) and var. muricata (white, purple). The results support the proposal by Danert and others that these variants should be considered as varieties or forms of a single species, Datura metel. The analysis of tropane alkaloids in the seeds, flowers, and leaves of these four varieties showed that scopolamine was always dominant over hyoscyamine. The range of the scopolamine content (% of dry weight) of seeds, flowers, and leaves was 0.294 (var. rubra)-0.631 (var. fastuosa), 0.190 (var. metel)-0.698 (var. rubra), and 0.042 (var. rubra)-0.255 (var.metel), respectively. These findings proved that all the varieties, including var. muricata, which exhibited medium scopolamine content among the varieties, can be utilized as sources of scopolamine. PMID:8874823

Hiraoka, N; Tashimo, K; Kinoshita, C; Hiro'oka, M



Binding of isoquinoline alkaloids berberine, palmatine and coralyne to hemoglobin: structural and thermodynamic characterization studies.  


Berberine, palmatine and coralyne, the isoquinoline alkaloids distributed in many botanical families, are extensively investigated due to their potential therapeutic actions and clinical utilities. In this work, their binding characteristics to hemoglobin (Hb) were studied by UV-vis absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy, isothermal calorimetric titration and differential scanning calorimetric techniques. The results indicated that all the three alkaloids caused strong fluorescence quenching of Hb by the static quenching mechanism, but with differing quenching efficiencies. There was a single binding site on Hb for these alkaloids. According to the theory of Förster resonance energy transfer, the binding distances between ?-Trp37 of Hb and berberine, palmatine and coralyne were evaluated to be 2.78 nm, 2.64 nm and 3.29 nm, respectively. The result of synchronous fluorescence, circular dichroism and 3D fluorescence revealed that the polarity around Trp residues experienced a significant increase in the presence of alkaloids. The binding was favoured by enthalpy and entropy changes. Results of circular dichroism, 3D and synchronous fluorescence studies confirmed that the binding of the alkaloids significantly changed the secondary structure of Hb. The studies revealed that berberine and palmatine bound to a site near to the ?1?2 interface on Hb different than coralyne but the affinity of coralyne was one order higher than that of berberine and palmatine. PMID:23147244

Hazra, Soumitra; Hossain, Maidul; Suresh Kumar, Gopinatha



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


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



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.

Madaan, Reecha; Kumar, S.



How polyamine synthesis inhibitors and cinnamic acid affect tropane alkaloid production.  


Hairy roots of Brugmansia candida produce the tropane alkaloids scopolamine and hyoscyamine. In an attempt to divert the carbon flux from competing pathways and thus enhance productivity, the polyamine biosynthesis inhibitors cyclohexylamine (CHA) and methylglyoxal-bis-guanylhydrazone (MGBG) and the phenylalanine-ammonia-lyase inhibitor cinnamic acid were used. CHA decreased the specific productivity of both alkaloids but increased significantly the release of scopolamine (approx 500%) when it was added in the mid-exponential phase. However, when CHA was added for only 48 h during the exponential phase, the specific productivity of both alkaloids increased (approx 200%), favoring scopolamine. Treatment with MGBG was detrimental to growth but promoted release into the medium of both alkaloids. However, when it was added for 48 h during the exponential phase, MGBG increased the specific productivity (approx 200%) and release (250- 1800%) of both alkaloids. Cinnamic acid alone also favored release but not specific productivity. When a combination of CHA or MGBG with cinnamic acid was used, the results obtained were approximately the same as with each polyamine biosynthesis inhibitor alone, although to a lesser extent. Regarding root morphology, CHA inhibited growth of primary roots and ramification. However, it had a positive effect on elongation of lateral roots. PMID:17416978

Marconi, Patricia L; Alvarez, María A; Pitta-Alvarez, Sandra I



Determination of caffeine and sympathomimetic alkaloids in weight loss supplements by high-performance liquid chromatography.  


Reversed-phase high-performance liquid chromatography utilizing photodiode array detection is used for the simultaneous determination of caffeine and nine alkaloids from Citrus aurantium (CA) and ephedra (EA) contained in dietary weight loss products. Since the Food and Drug Administration (FDA) ban of EA, manufacturers have substituted CA in their weight loss formulations, usually combined with high levels of caffeine. The alkaloids contained in CA have some physiological effects similar to those of the EA alkaloids and are, therefore, cause for concern. Caffeine has been shown to potentiate the toxicity of the EA alkaloids. Recently, a federal judge overturned the absolute ban and allowed marketing of low levels (<10 mg/day) of total EA alkaloids. To support an absolute ban, the FDA is now compelled to perform dose-dependent toxicology studies to determine the toxic dose(s) of EA. The toxicity of the CA compounds is largely unknown, especially in combination with caffeine. The described method enables quantitation over a wide range of product formulations. Recoveries range from 91% to 100% from a variety of fortified plant matrices. PMID:18218190

Evans, Ronald L; Siitonen, Paul H



Optimization of Extraction and Enrichment of Steroidal Alkaloids from Bulbs of Cultivated Fritillaria cirrhosa  

PubMed Central

The bulbs of cultivated Fritillaria cirrhosa (BCFC) are used in China both for food and folk medicine due to its powerful biological activities. The aim of this study is to optimize the extraction and enrichment conditions of alkaloids from BCFC. Firstly, the orthogonal experimental design was used to optimize and evaluate four variables (ethanol concentration, solid-liquid ratio, extraction time, and temperature). Thereafter, resin adsorption was as a means to enrich alkaloids. Among 16 tested resins, H-103 resin presented higher adsorption capacity and desorption ratio. The equilibrium experimental data of the adsorption of total alkaloids, imperialine, and peimisine were well-fitted to the pseudo-first-order kinetics model, Langmuir and Freundlich isotherms models. Finally, in order to optimize the parameters for purifying alkaloids, dynamic adsorption and desorption tests were carried out. After one run treatment with H-103 resin, the contents of total alkaloids, imperialine, and peimisine in the product were 21.40-, 18.31-, and 22.88-fold increased with recovery yields of 94.43%, 90.57%, and 96.16%, respectively.

Wang, Shu; Du, Qingdan; Wang, Nanyi; Liu, Simei; Wang, Xiaoxia; Jiang, Jinghui



Alkaloid defenses of co-mimics in a putative M?llerian mimetic radiation  

PubMed Central

Background Polytypism in aposematic species is unlikely according to theory, but commonly seen in nature. Ranitomeya imitator is a poison frog species exhibiting polytypic mimicry of three congeneric model species (R. fantastica, R. summersi, and two morphs of R. variabilis) across four allopatric populations (a "mimetic radiation"). In order to investigate chemical defenses in this system, a key prediction of Müllerian mimicry, we analyzed the alkaloids of both models and mimics from four allopatric populations. Results In this study we demonstrate distinct differences in alkaloid profiles between co-mimetic species within allopatric populations. We further demonstrate that R. imitator has a greater number of distinct alkaloid types than the model species and more total alkaloids in all but one population. Conclusions Given that R. imitator is the more abundant species in these populations, R. imitator is likely driving the majority of predator-learned avoidance in these complexes. The success of Ranitomeya imitator as a putative advergent mimic may be a direct result of differences in alkaloid sequestration. Furthermore, we propose that automimicry within co-mimetic species is an important avenue of research.



Dietary alkaloids and the development of androconial organs in Estigmene acrea  

PubMed Central

Male salt marsh moths, Estigmene acrea (Lepidoptera: Arctiidae), possess inflatable androconial organs called coremata. Prior to mating males form aggregations and inflate their coremata en masse. The communal display attracts additional males and females for the purpose of mating. The coremata are known to carry the plant-derived dihydropyrrolizine, hydroxydanaidal. This pheromonal substance is derived from secondary plant chemicals called pyrrolizidine alkaloids found in the larval diet. When E. acrea larvae were raised on semi-synthetic diets containing different levels of the pyrrolizidine alkaloid precursors the alkaloids triggered a pronounced morphogenetic effect. Adult males that fed on high levels of the pyrrolizidine alkaloid monocrotaline N-oxide (2500 µg) developed the largest coremata. Males that fed on lower levels of monocrotaline N-oxide (500 µg) or no alkaloid, while normal in body weight, had coremata that were progressively smaller and less robust. The size of the coremata and their commensurate pheromonal charge may have behavioral consequences in the unusual mating system of this species.

Davenport, Jason W.; Conner, William E.



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


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 10(5)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. PMID:22613127

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



Alkaloid metabolism in thrips-Papaveraceae interaction: recognition and mutual response.  


Frankliniella occidentalis (Pergande), the Western Flower Thrips (WFT), is a polyphagous and highly adaptable insect of the order Thysanoptera. It has a broad host range but is rarely found on Papaveraceae, which might be due to deterrent effects of alkaloids present in most species of this family. In order to test the adaptive potential of WFT, we investigated its interaction with two Papaveraceae offered as sole feeding source. We found that WFT are able to live and feed on leaves of Eschscholzia californica and Chelidonium majus. Both plants respond to thrips feeding by the enhanced production of benzophenanthridine alkaloids. Furthermore, cell cultures of E. californica react to water insoluble compounds prepared from adult thrips with enhanced alkaloid production. During feeding, WFT take up benzophenanthridine alkaloids from either plant and from an artificial feeding medium and convert them to their less toxic dihydroderivatives. This was shown in detail with sanguinarine, the most cytotoxic benzophenanthridine. A similar conversion is used in plants to prevent self-intoxication by their own toxins. We conclude that WFT causes a phytoalexin-like response in Papaveraceae, but is able to adapt to such host plants by detoxification of toxic alkaloids. PMID:24331426

Schütz, Ingeborg; Moritz, Gerald B; Roos, Werner



Antiplasmodial activity of extracts and alkaloids of three Alstonia species from Thailand.  


Methanol extracts prepared from various parts of Alstonia scholaris, A. macrophylla and A. glaucescens, collected from Thailand, have been assessed for antiplasmodial activity against multidrug-resistant K1 strain of Plasmodium falciparum cultured in human erythrocytes. Pronounced antiplasmodial activity was exhibited by methanol extract of the root bark of A. macrophylla with an IC50 value of 5.7 micrograms/ml. Thirteen indole alkaloids were isolated from the active extract. These alkaloids and a semisynthetic bisindole O-acetylmacralstonine were subsequently tested against the K1 strain of P. falciparum. Pronounced antiplasmodial activity was observed mainly among the bisindole alkaloids, particularly villalstonine and macrocarpamine with IC50 values of 0.27 and 0.36 microM, respectively. The potent alkaloids were further tested against T9-96, the chloroquine-sensitive strain of P. falciparum. It has been found that the active alkaloids, in contrast to chloroquine, have significantly higher affinity to the K1 strain than to the T9-96 strain. PMID:10630106

Keawpradub, N; Kirby, G C; Steele, J C; Houghton, P J



Seasonal accumulation of major alkaloids in organs of pharmaceutical crop Narcissus Carlton.  


Narcissus pseudonarcissus (L.) cv. Carlton is being cultivated as a main source of galanthamine from the bulbs. After galanthamine, haemanthamine and narciclasine are the next most abundant alkaloids in this cultivar. Both these compounds are promising chemical scaffolds for potential anticancer drugs. For further research and drug development, a reliable supply of these compounds will be needed. In this study a field experiment was conducted to investigate the levels of galanthamine, haemanthamine and narciclasine in plants of N. pseudonarcissus cv. Carlton. In a field experiment alkaloids in the bulbs, leaves and roots were analyzed by quantitative (1)H NMR to monitor the variations during the growing season. Major primary and secondary metabolites were identified in the various plant parts. Multivariate data analysis was performed on the (1)H NMR spectra to investigate how metabolites changed in the plant organs over time. The results show that the leaves have relatively high concentrations of the alkaloids before flowering. The bulbs had lower concentrations of the compounds of interest but would have a higher total yield of alkaloids due to bigger biomass. Narcissus pseudonarcissus cv. Carlton represents a good source of galanthamine, and can potentially be a source of the other major alkaloids depending on choice of organ and harvest time. PMID:23318143

Lubbe, Andrea; Gude, Henk; Verpoorte, Robert; Choi, Young Hae



Lupin alkaloids from teratogenic and nonteratogenic lupins. III. Identification of anagyrine as the probable teratogen by feeding trials  

Microsoft Academic Search

Alkaloidal extracts from teratogenic lupins produced congenital deformities in calves typical of crooked calf disease when the extracts were administered to pregnant cows during the susceptible gestational period. These data and previous epidemiologic studies suggest that one of the four alkaloids in the preparation, anagyrine, is the responsible teratogen. Severity of the malformations was directly related to the level of

Richard F. Keeler



Enzymatic and chemo-enzymatic approaches towards natural and non-natural alkaloids: indoles, isoquinolines, and others.  


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. Enzyme crystallisation, 3D analyses and site-directed mutation allowed rational engineering of enzyme substrate acceptance, which in turn can be used for reprogramming in vivo alkaloid biosynthesis and for the design of biomimetic alkaloid syntheses. These strategies broaden structural diversity and allow the creation of large libraries of unnatural alkaloid with expected optimised or novel biological activities. The chemo-enzymatic syntheses of the above-mentioned alkaloid groups and their precursors (in addition to selected examples of other alkaloid families) provides an overview of how enzyme reactions are integrated into the development of total chemical syntheses. PMID:21495257

Stöckigt, Joachim; Chen, Zhong; Ruppert, Martin



Antioxidant and antimicrobial activities of aporphinoids and other alkaloids from the bark of Annona salzmannii A. DC. (Annonaceae)  

Microsoft Academic Search

The antioxidant capacity by oxygen radical absorbance capacity (ORAC)-FL method and antimicrobial activity using the broth microdilution method of aporphinoids (liriodenine 1, anonaine 2 and asimilobine 3) and other alkaloids (reticuline 4 and cleistopholine 5) isolated from the bark of Annona salzmannii A. DC. (Annonaceae) were evaluated. For antioxidant activity, the most active alkaloid was asimilobine with ORAC value of

Emmanoel Vilaça Costa; Pedro Ernesto Oliveira da Cruz; Caroline Caramano de Lourenço; Valéria Regina de Souza Moraes; Paulo Cesar de Lima Nogueira; Marcos José Salvador



In vitro vasodilator mechanisms of the indole alkaloids rhynchophylline and isorhynchophylline, isolated from the hook of Uncaria rhynchophylla (Miquel)  

Microsoft Academic Search

Rhynchophylline (Rhy) and isorhynchophylline (Isorhy), indole alkaloids from Uncaria hooks, reportedly exert hypotensive and vasodilatory effects, but the mechanism of action is unclear. We therefore investigated the relaxant effects of these two isomeric alkaloids in rat arteries in vitro, in particular in respect of the various functional Ca2+ pathways. Both Rhy and Isorhy relaxed aortic rings precontracted with phenylephrine (PE,

Wen-Bo Zhang; Chang-Xun Chen; Si-Mui Sim; Chiu-Yin Kwan



Antiplasmodial and antimycobacterial cyclopeptide alkaloids from the root of Ziziphus mauritiana.  


Investigation of the MeOH extract obtained from the root of the Ziziphus mauritiana grown in Thailand resulted in the isolation of two 14- and 13-membered cyclic alkaloids, mauritine L (1) and mauritine M (2), and three known cyclopeptide alkaloids, nummularines H (3), B (4) and hemsine A (5). Their structures were elucidated on the basis of extensive NMR spectroscopic analysis. The first single crystal X-ray diffraction study of the 13-membered ring cyclopeptide, nummularine B methiodide (4'), revealed all S configurations on the amino acid residues. The isolated alkaloids exhibited potent antiplasmodial activity against the parasite Plasmodium falciparum with the inhibitory concentration (IC(50)) ranging from 3.7 to 10.3?M. Compounds 2 and 3 also demonstrated antimycobacterial activity against Mycobacterium tuberculosis with the MIC of 72.8 and 4.5?M, respectively. PMID:21450320

Panseeta, Panomwan; Lomchoey, Kanlaya; Prabpai, Samran; Kongsaeree, Palangpon; Suksamrarn, Apichart; Ruchirawat, Somsak; Suksamrarn, Sunit



Main alkaloids of Peganum harmala L. and their different effects on dicot and monocot crops.  


Alkaloids with allelopathic activity are not as well-known as other allelochemicals. Our study revealed that total alkaloids from seeds of the medicinal plant Peganum harmala L. possessed significant growth inhibitory effect on four treated plants, with dicot plants (lettuce and amaranth) being more sensitive than the tested monocot plants (wheat and ryegrass). Further investigation led to the isolation of harmaline and harmine as the main active ingredients in the total alkaloids of P. harmala seeds. Harmaline exerted potent inhibitory effects on seedling growth of treated plants, especially dicots, inhibiting root elongation of lettuce and amaranth by 31% and 47% at a very low concentration (5 µg/mL), whereas harmine exhibited much weaker non-selective inhibitory effect on the plants. Considering the high yield and poor utilization of P. harmala in China, we anticipate that this plant could be exploited as an alternative weed management tool in the future. PMID:23446919

Shao, Hua; Huang, Xiaoli; Zhang, Yuanming; Zhang, Chi



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


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



Berberine: a plant alkaloid with therapeutic potential for central nervous system disorders.  


Berberine, an isoquinoline alkaloid of the protoberberine type found in an array of plants, has been used in Indian and Chinese medicines as an antimicrobial, stomachic, bitter tonic and in the treatment of oriental sores. Although pharmacological investigations of berberine have been reported by many in the past, there is renewed interest in berberine because of its reported beneficial effect in various neurodegenerative and neuropsychiatric disorders. The alkaloid is reported to modulate neurotransmitters and their receptor systems in the brain. This review attempts to discuss the pharmacological basis of the use of berberine in various central nervous system and related disorders. Its protective effect in Alzheimer's, cerebral ischemia, mental depression, schizophrenia and anxiety are highlighted. However, more detailed clinical trials along with a safety assessment of berberine are warranted for positioning the alkaloid in the treatment of neurological disorders. PMID:19998323

Kulkarni, S K; Dhir, Ashish



Subcellular Localization of Enzymes Involved in Indole Alkaloid Biosynthesis in Catharanthus roseus1  

PubMed Central

The subcellular localization of enzymes involved in indole alkaloid biosynthesis in leaves of Catharanthus roseus has been investigated. Tryptophan decarboxylase and strictosidine synthase which together produce strictosidine, the first indole alkaloid of this pathway, are both cytoplasmic enzymes. S-Adenosyl-l-methionine: 16-methoxy-2,3-dihydro-3-hydroxytabersonine-N-methyltransferase which catalyses the third to last step in vindoline biosynthesis could be localized in the chloroplasts of Catharanthus leaves and is specifically associated with thylakoids. Acetyl-coenzyme-A-deacetylvindoline-O-acetyltransferase which catalyses the last step in vindoline biosynthesis could also be localized in the cytoplasm. The participation of the chloroplast in this pathway suggests that indole alkaloid intermediates enter and exit this compartment during the biosynthesis of vindoline.

De Luca, Vincenzo; Cutler, Adrian J.



Hainanerectamines A-C, Alkaloids from the Hainan Sponge Hyrtios erecta  

PubMed Central

Two new indole alkaloids, hainanerectamines A (1) and B (2), and one new ?-carboline alkaloids, hainanerectamines C (4), along with five known related alkaloids (3, 5–8), have been isolated from the Hainan marine sponge Hyrtios erecta. The structures of new compounds 1, 2 and 4 were determined by detailed analysis of their 1D and 2D NMR spectra and by comparison of their spectroscopic data with those of related model compounds. Compounds 2–4 exhibited moderate inhibitory activity against Aurora A, a member of serine/threonine kinase family involving in the regulation of cell division and a new target in cancer treatment, with IC50 values of 24.5, 13.6, and 18.6 ?g/mL, respectively.

He, Wen-Fei; Xue, Duo-Qing; Yao, Li-Gong; Li, Jing-Ya; Li, Jia; Guo, Yue-Wei



Ningalins A-D: Novel Aromatic Alkaloids from a Western Australian Ascidian of the Genus Didemnum.  


Four aromatic alkaloids, ningalins A-D (1-4), three of which possess new carbon skeletons, were isolated from an undescribed ascidian of the genus Didemnumcollected in Western Australia near Ningaloo Reef. The structures of these new alkaloids were elucidated by interpretation of overall spectral data and by 2D NMR correlation methods. Ningalins A-D are composed of C(18), C(25), C(32), and C(40) condensed aromatic systems with the unifying theme that all appear derived via the condensation of the amino acid 3,4-dihydroxyphenylalanine (DOPA). In these highly condensed alkaloids, steric crowding forces several catechol rings into twisted configurations, resulting in unexpected shielding and deshielding of several proton shifts in their NMR spectra. Because the ningalins are related to other metal binding o-catechols, it is conceivable that they too participate in the metal chelation phenomena characteristic of this class of marine invertebrates. PMID:11671712

Kang, Heonjoong; Fenical, William



Induction of endogenous avian tumor virus gene expression by pyrrolizidine alkaloids.  


The pyrrolizidine alkaloids (PA) are toxic compounds which occur naturally in plant species throughout the world. They have been implicated as both carcinogenic and mutagenic agents. An active metabolite of the alkaloids, the pyrrole, which is a strong alkylating agent, is thought to be the toxicant. The naturally occurring alkaloid, jacobine , is able to induce the production of endogenous avian RNA tumor virus particles in cultured chick embryo fibroblasts (CEF). When jacobine was modified to form retronecine it no longer induced virus particles. Conversion of retronecine to its pyrrole resulted in a compound capable of inducing virus particle production. The isobutyryl monoester of retronecine was also able to induce virus particle production, but the isobutyryl monoester pyrrole was unexpectedly inactive as an inducer. This type of viral induction system is useful for studying the effect of modification of the inducer on its biological activity. PMID:6202431

Pearson, M N; Karchesy, J J; Deeney, A O; Deinzer, M L; Beaudreau, G S



Phenolic alkaloids as a new class of antioxidants in Portulaca oleracea.  


Antioxidant activities of three phenolic alkaloids, i.e., oleracein A (OA), oleracein B (OB) and oleracein E (OE), isolated from Portulaca oleracea were determined, based on scavenging activity against 1,1-diphenyl- 2-picryl-hydrazyl (DPPH) radical and inhibitory effect on hydrogen peroxide-induced lipid peroxidation in rat brain homogenates. The DPPH radical scavenging activities of these phenolic alkaloids were lower than caffeic acid but higher than ascorbic acid and alpha-tocopherol, being in the following order: OB > OA > OE. OE was most potent in preventing formation of malondialdehyde (MDA) with an EC(50) value of 73.13 microM, close to that of caffeic acid (72.09 microM). It was demonstrated that phenolic alkaloids served as a new class of antioxidant agents in this plant. PMID:19140117

Yang, Zijuan; Liu, Cejia; Xiang, Lan; Zheng, Yinan



Preparative isolation of guaipyridine sesquiterpene alkaloid from Artemisia rupestris L. flowers using high-speed counter-current chromatography.  


Although the medicinal plant Artemisia rupestris L. has been widely researched for several decades, its alkaloids have never been isolated before. To our surprise, the alkaloids in the plant were not detected in the stems but detected in the flowers. Herein, a novel and strange guaipyridine sesquiterpene alkaloid with a carboxyl group named rupestine was purified successfully from the total alkaloids extracted from the flowers by high-speed counter-current chromatography (HSCCC). The two-phase solvent system used was composed of ethyl acetate-methanol-water (8:1:7, v/v/v). Fifty six milligrams of rupestine was obtained at over 97% purity and 95% recovery from 200 mg of the total alkaloids in one-step separation. Its structure was elucidated by spectroscopic methods including high resolution ESI-MS, (1)H NMR, (13)C NMR, Heteronuclear Multiple Bond Correlation (HMBC), Heteronuclear Single Quantum Coherence (HSQC), and Nuclear Overhauser Enhancement Spectroscopy (NOESY). PMID:18546395

Su, Zhen; Wu, Hankui; Yang, Yi; Aisa, Haji Akber; Slukhan, Usmanova; Aripova, Salimakhon



Pharmacochemistry and integrated pharmacokinetics of six alkaloids after oral administration of Huang-Lian-Jie-Du-Tang decoction.  


Pharmacochemistry and integrated pharmacokinetics of six alkaloids (groenlandicine, berberine, palmatine, epiberberine, jatrorrhizine, and columbamine) after oral administration of Huang-Lian-Jie-Du-Tang (HLJDT) decoction were investigated in this paper. The method of plasma pharmacochemistry was applied to predict the potential bioactive components in HLJDT decoction. Based on the accurate molecular weight, 10 components including 2 flavonoids (baicalin and wogonoside), 1 iridoid glycoside (geniposide), and 7 alkaloids (above-mentioned 6 alkaloids and coptisine) were structurally identified. Then, integrated pharmacokinetics of the alkaloids in Sprague-Dawley rats after oral administration of HLJDT decoction was investigated by HPLC method. The results showed that the pharmacokinetic behaviors of the alkaloids were different although their chemical structures were similar. This study developed a method to predict the potential bioactive components in HLJDT decoction and research the pharmacokinetic behaviors of the potential bioactive components. PMID:24797560

Ma, Zhao-Tang; Yang, Xiu-Wei; Zhang, Ying; Liu, Jian-Xun



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.

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



In vitro permeation of mesembrine alkaloids from Sceletium tortuosum across porcine buccal, sublingual, and intestinal mucosa.  


Sceletium tortuosum is an indigenous South African plant that has traditionally been used for its mood-enhancing properties. Recently, products containing S. tortuosum have become increasingly popular and are commonly administered as tablets, capsules, teas, decoctions, or tinctures, while traditionally the dried plant material has been masticated. This study evaluated the in vitro permeability of the four major S. tortuosum alkaloids (i.e., mesembrine, mesembrenone, mesembrenol, and mesembranol) across porcine intestinal, sublingual, and buccal tissues in their pure form and in the form of three different crude plant extracts, namely water, methanol, and an acid-base alkaloid-enriched extract. The permeability of mesembrine across intestinal tissue was higher than that of the highly permeable reference compound caffeine (which served as a positive control for membrane permeability) both in its pure form, as well as in the form of crude extracts. The intestinal permeability of mesembranol was similar to that of caffeine, while those of mesembrenol and mesembrenone were lower than that of caffeine, but much higher than that of the poorly permeable reference compound atenolol (which served as a negative control for membrane permeability). In general, the permeabilities of the alkaloids were lower across the sublingual and the buccal tissues than across the intestinal tissue. However, comparing the transport of the alkaloids with that of the reference compounds, there are indications that transport across the membranes of the oral cavity may contribute considerably to the overall bioavailability of the alkaloids, depending on pre-systemic metabolism, when the plant material is chewed and kept in the mouth for prolonged periods. The results from this study confirmed the ability of the alkaloids of S. tortuosum in purified or crude extract form to permeate across intestinal, buccal, and sublingual mucosal tissues. PMID:22105579

Shikanga, Emmanuel A; Hamman, Josias H; Chen, Weiyang; Combrinck, Sandra; Gericke, Nigel; Viljoen, Alvaro M



Chemometric approach for development, optimization, and validation of different chromatographic methods for separation of opium alkaloids.  


The excessive and continuously growing interest in the simultaneous determination of poppy alkaloids imposes the development and optimization of convenient high-throughput methods for the assessment of the qualitative and quantitative profile of alkaloids in poppy straw. Systematic optimization of two chromatographic methods (gas chromatography (GC)/flame ionization detector (FID)/mass spectrometry (MS) and reversed-phase (RP)-high-performance liquid chromatography (HPLC)/diode array detector (DAD)) for the separation of alkaloids from Papaver somniferum L. (Papaveraceae) was carried out. The effects of various conditions on the predefined chromatographic descriptors were investigated using chemometrics. A full factorial linear design of experiments for determining the relationship between chromatographic conditions and the retention behavior of the analytes was used. Central composite circumscribed design was utilized for the final method optimization. By conducting the optimization of the methods in very rational manner, a great deal of excessive and unproductive laboratory research work was avoided. The developed chromatographic methods were validated and compared in line with the resolving power, sensitivity, accuracy, speed, cost, ecological aspects, and compatibility with the poppy straw extraction procedure. The separation of the opium alkaloids using the GC/FID/MS method was achieved within 10 min, avoiding any derivatization step. This method has a stronger resolving power, shorter analysis time, better cost/effectiveness factor than the RP-HPLC/DAD method and is in line with the "green trend" of the analysis. The RP-HPLC/DAD method on the other hand displayed better sensitivity for all tested alkaloids. The proposed methods provide both fast screening and an accurate content assessment of the six alkaloids in the poppy samples obtained from the selection program of Papaver strains. PMID:22318699

Acevska, J; Stefkov, G; Petkovska, R; Kulevanova, S; Dimitrovska, A



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.

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



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.

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



Plant-Symbiotic Fungi as Chemical Engineers: Multi-Genome Analysis of the Clavicipitaceae Reveals Dynamics of Alkaloid Loci  

PubMed Central

The fungal family Clavicipitaceae includes plant symbionts and parasites that produce several psychoactive and bioprotective alkaloids. The family includes grass symbionts in the epichloae clade (Epichloë and Neotyphodium species), which are extraordinarily diverse both in their host interactions and in their alkaloid profiles. Epichloae produce alkaloids of four distinct classes, all of which deter insects, and some—including the infamous ergot alkaloids—have potent effects on mammals. The exceptional chemotypic diversity of the epichloae may relate to their broad range of host interactions, whereby some are pathogenic and contagious, others are mutualistic and vertically transmitted (seed-borne), and still others vary in pathogenic or mutualistic behavior. We profiled the alkaloids and sequenced the genomes of 10 epichloae, three ergot fungi (Claviceps species), a morning-glory symbiont (Periglandula ipomoeae), and a bamboo pathogen (Aciculosporium take), and compared the gene clusters for four classes of alkaloids. Results indicated a strong tendency for alkaloid loci to have conserved cores that specify the skeleton structures and peripheral genes that determine chemical variations that are known to affect their pharmacological specificities. Generally, gene locations in cluster peripheries positioned them near to transposon-derived, AT-rich repeat blocks, which were probably involved in gene losses, duplications, and neofunctionalizations. The alkaloid loci in the epichloae had unusual structures riddled with large, complex, and dynamic repeat blocks. This feature was not reflective of overall differences in repeat contents in the genomes, nor was it characteristic of most other specialized metabolism loci. The organization and dynamics of alkaloid loci and abundant repeat blocks in the epichloae suggested that these fungi are under selection for alkaloid diversification. We suggest that such selection is related to the variable life histories of the epichloae, their protective roles as symbionts, and their associations with the highly speciose and ecologically diverse cool-season grasses.

Schardl, Christopher L.; Young, Carolyn A.; Hesse, Uljana; Amyotte, Stefan G.; Andreeva, Kalina; Calie, Patrick J.; Fleetwood, Damien J.; Haws, David C.; Moore, Neil; Oeser, Birgitt; Panaccione, Daniel G.; Schweri, Kathryn K.; Voisey, Christine R.; Farman, Mark L.; Jaromczyk, Jerzy W.; Roe, Bruce A.; O'Sullivan, Donal M.; Scott, Barry; Tudzynski, Paul; An, Zhiqiang; Arnaoudova, Elissaveta G.; Bullock, Charles T.; Charlton, Nikki D.; Chen, Li; Cox, Murray; Dinkins, Randy D.; Florea, Simona; Glenn, Anthony E.; Gordon, Anna; Guldener, Ulrich; Harris, Daniel R.; Hollin, Walter; Jaromczyk, Jolanta; Johnson, Richard D.; Khan, Anar K.; Leistner, Eckhard; Leuchtmann, Adrian; Li, Chunjie; Liu, JinGe; Liu, Jinze; Liu, Miao; Mace, Wade; Machado, Caroline; Nagabhyru, Padmaja; Pan, Juan; Schmid, Jan; Sugawara, Koya; Steiner, Ulrike; Takach, Johanna E.; Tanaka, Eiji; Webb, Jennifer S.; Wilson, Ella V.; Wiseman, Jennifer L.; Yoshida, Ruriko; Zeng, Zheng



Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox.  


A methanol extract of the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, five dimeric pyrrolidinoindoline alkaloids and four sesquiterpenes were isolated, together with 16 known compounds. Among them, (-)-chimonanthine (1, IC50 = 0.93 ?M), (-)-folicanthine (2, 1.4 ?M), and (-)-calycanthidine (3, 1.8 ?M) showed potent inhibitory effects without notable cytotoxicity at the effective concentrations. The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable. PMID:24668298

Morikawa, Toshio; Nakanishi, Yusuke; Ninomiya, Kiyofumi; Matsuda, Hisashi; Nakashima, Souichi; Miki, Hisako; Miyashita, Yu; Yoshikawa, Masayuki; Hayakawa, Takao; Muraoka, Osamu



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


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



Short pathways to complexity generation: fungal peptidyl alkaloid multicyclic scaffolds from anthranilate building blocks.  


Complexity generation in naturally occurring peptide scaffolds can occur either by posttranslational modifications of nascent ribosomal proteins or through post assembly line tailoring of nonribosomal peptides. Short enzymatic pathways utilizing bimodular and trimodular nonribosomal peptide synthetase (NRPS) assembly lines, followed by tailoring oxygenases and/or prenyltransferases, efficiently construct complex fungal peptidyl alkaloid scaffolds in Aspergilli, Neosartorya, and Penicillium species. Use of the nonproteinogenic amino acid anthranilate as chain-initiating building block and chain-terminating intramolecular nucleophile leads efficiently to peptidyl alkaloid scaffolds with two to seven fused rings. PMID:23659680

Walsh, Christopher T; Haynes, Stuart W; Ames, Brian D; Gao, Xue; Tang, Yi



Isolation and characterization of antineoplastic alkaloids from Catharanthus roseus L. Don. cultivated in Egypt.  


Vinblastine and vincristine (the antileukemic agents) were isolated, in a pure form, from Catharanthus roseus L. Don., cultivated in Egypt, by several chromatographic techniques. Five modified methods for the preparation of total alkaloids were carried out. All the isolated mixtures were evaluated by HPLC and HPTLC analyses. The antineoplastic alkaloids; vinblastine and vincristine, were isolated by the use of vacuum liquid chromatographic column on silica gel : aluminium oxide (1:1) mixed bed vacuum liquid chromatography (VLC), Charcoal column, and finally purified by centrifugally accelerated radial chromatography (Chromatotrone). PMID:20209002

Shams, Khaled A; Nazif, Naglaa M; Abdel Azim, Nahla S; Abdel Shafeek, Khaled A; El-Missiry, Mostafa M; Ismail, Shams I; Seif El Nasr, Medhat M



Evolution of a Strategy for Total Synthesis of the Marine Fungal Alkaloid (?)-Communesin F  

PubMed Central

A new synthetic strategy for construction of the heptacyclic marine fungal alkaloid (±)-communesin F has been devised. Key reactions include an intramolecular Heck cyclization of a tetrasubstituted alkene to generate a tetracyclic enamide bearing one of the quaternary carbon centers (C7) of the alkaloid, an intramolecular reductive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework containing the southern aminal, a stereoselective N-Boc-lactam enolate C-allylation to introduce the second quaternary carbon center (C8), and an azide reduction/N-Boc-lactam-opening cascade leading to the northern aminal.

Seo, Jae Hong; Liu, Peng; Weinreb, Steven M.



Alkaloids from the Roots of Stichoneuron caudatum and Their Acetylcholinesterase Inhibitory Activities.  


Four new stichoneurine-type alkaloids, stichoneurines F and G (1-2) and sessilistemonamines E and F (3-4), have been isolated from the root extracts of Stichoneuron caudatum. The structures and relative configurations of these alkaloids have been determined by spectroscopic methods and molecular modeling experiments. Compounds 1-4 were tested for their acetylcholinesterase (AChE) inhibitory activities against human AChE. Compound 3 showed significant inhibitory activity with an IC50 value of 9.1 ± 0.15 ?M. PMID:24606395

Ramli, Rosdayati A; Lie, Wilford; Pyne, Stephen G



New lamellarin alkaloids from the Indian ascidian Didemnum obscurum and their antioxidant properties.  


Three new lamellarin alkaloids, lamellarins gamma (1), alpha (2), and epsilon (3), along with eight known lamellarin alkaloids, lamellarins M (4), K (5), K-diacetate (6), K-triacetate (7), U (8), I (9), C-diacetate (10), and X-triacetate (11), have been isolated from the Indian ascidian Didemnum obscurum. The structures of 1-11 were established using standard spectroscopic techniques. The structure of lamellarin K-triacetate (7) was further confirmed by X-ray crystallographic analysis. The antioxidant properties of lamellarin gamma, lamellarin gamma-monoacetate, lamellarins K, U, and I, and lamellarin C-diacetate were evaluated. PMID:15270574

Krishnaiah, P; Reddy, V L N; Venkataramana, G; Ravinder, K; Srinivasulu, M; Raju, T V; Ravikumar, K; Chandrasekar, D; Ramakrishna, S; Venkateswarlu, Y



Regiospecific, Enantiospecific Total Synthesis of C-19 Methyl Substituted Sarpagine Alkaloids Dihydroperaksine-17-al and Dihydroperaksine  

PubMed Central

The optically active tetracyclic ketone 8 was converted into the pentacylic core 14 of the C-19 methyl substituted Na-H sarpagine and ajmaline alkaloids via a critical haloboration reaction. The ketone 14 was then employed in the total synthesis of 19(S),20(R)-dihydroperaksine-17-al (1) and 19(S),20(R)-dihydroperaksine (2). The key regioselective hydroboration and controlled oxidation-epimerization sequence developed in this approach should provide a general method to functionalize the C(20)-C(21) double bond in the ajmaline-related indole alkaloids.

Edwankar, Rahul V.; Edwankar, Chitra R.; Deschamps, Jeffrey



Aporphine alkaloids and feruloylamides from the bark of Xylopia benthamii R.E. Fries (Annonaceae).  


The bark of Xylopia benthamii R.E. Fries was investigated in a search for new bioactive compounds. The ethanolic extract of the air-dried bark of X. benthamii was obtained and submitted to an acidic extraction procedure to obtain an alkaloid mixture. Chromatographic fractionation led to the isolation of two aporphine alkaloids, nornantenine and laurotetanine, and a mixture of trans- and cis-feruloyltyramine, isolated for the first time in this genus. Structures were established by spectroscopic methods as NMR (1D and 2D) and mass spectrometry (ESI-MS). PMID:22007762

Pimenta, L P S; Mendonça, D D



Sebastianines A and B, novel biologically active pyridoacridine alkaloids from the Brazilian ascidian Cystodytes dellechiajei.  


Fractionation of the crude methanol extract of the ascidian Cystodytes dellechiajei collected in Brazil yielded two novel alkaloids, sebastianine A (1) and sebastianine B (2). The structures of both 1 and 2 were established by analysis of spectroscopic data, indicating an unprecedented ring system for both compounds, comprising a pyridoacridine system fused with a pyrrole unit in sebastianine A (1) and a pyridoacridine system fused with a pyrrolidine system condensed with alpha-hydroxyisovaleric acid in sebastianine B (2). Both alkaloids displayed a cytotoxic profile against a panel of HCT-116 colon carcinoma cells indicative of a p53 dependent mechanism. PMID:12126446

Torres, Yohandra R; Bugni, Tim S; Berlinck, Roberto G S; Ireland, Chris M; Magalhăes, Alviclér; Ferreira, Antonio G; Moreira Da Rocha, Rosana



Petrosamine, a potent anticholinesterase pyridoacridine alkaloid from a Thai marine sponge Petrosia n. sp.  


Two pyridoacridine alkaloids, including a known petrosamine and a new 2-bromoamphimedine were isolated from a Thai marine sponge Petrosia n. sp. The alkaloids were characterized on the basis of 1D and 2D NMR, MS, and IR spectroscopy. Only petrosamine showed strong acetylcholinesterase inhibitory activity approximately six times higher than that of the reference galanthamine. A computational docking study of petrosamine with the enzyme from the electric eel Torpedo californica (TcAChE) showed the major contribution to the petrosamine-TcAChE interaction to be arising from the quaternary ammonium group of petrosamine. PMID:18538575

Nukoolkarn, Veena S; Saen-oon, Suwipa; Rungrotmongkol, Thanyada; Hannongbua, Supot; Ingkaninan, Kornkanok; Suwanborirux, Khanit



Pyridoacridine alkaloids inducing neuronal differentiation in a neuroblastoma cell line, from marine sponge Biemna fortis.  


A new and three known pyridoacridine alkaloids were isolated from the Indonesian marine sponge Biemna fortis as neuronal differentiation inducers against a murine neuroblastoma cell line, Neuro 2A. The chemical structure of the new compound, labuanine A (1), was determined by spectroscopic study and chemical conversion. These pyridoacridine alkaloids induced multipolar neuritogenesis in more than 50% of cells at 0.03-3 micro M concentration. Compound 3, which showed the strongest neuritogenic activity among them, also induced increase of acetylcholinesterase, a neuronal marker in Neuro 2A and arrested cell cycle at the G2/M phase. PMID:12670647

Aoki, Shunji; Wei, Hong; Matsui, Kouhei; Rachmat, Rachmaniar; Kobayashi, Motomasa



Antibacterial benzofuran neolignans and benzophenanthridine alkaloids from the roots of Zanthoxylum capense.  


Two new 2-arylbenzofuran neolignans and a new benzophenanthridine alkaloid, together with six known benzophenanthridine alkaloids, namely, decarine, norchelerythrine, dihydrochelerythrine, 6-acetonyldihydrochelerythrine, tridecanonchelerythrine, and 6-acetonyldihydronitidine, have been isolated from the MeOH extract of the roots of Zanthoxylum capense. Their structures were elucidated by means of spectroscopic techniques including 2D NMR experiments. All the isolated compounds were evaluated for their in vitro antibacterial activity against gram-positive and gram-negative bacteria. Some compounds showed significant inhibitory activity against Staphylococcus aureus ATCC 6538 with MIC values ranging from 12.5 to 50 ?g/mL. PMID:22002848

Luo, Xuan; Pedro, Liliana; Milic, Vladimir; Mulhovo, Silva; Duarte, Aida; Duarte, Noélia; Ferreira, Maria-José U



Left, right, or both? On the configuration of the phenanthroindolizidine alkaloid tylophorine from Tylophora indica.  


The alkaloid (-)-tylophorine was isolated from a sample of Tylophora indica, and the crude extract was analyzed by HPLC/MS(n) and chiral HPLC/MS. While the literature states that the naturally occurring form of this alkaloid is the R-enantiomer and that its S-antipode is usually not found in nature, we confirmed the hypothesis of Govindachari and Nagarajan that natural levorotatory tylophorine is indeed a nearly racemic mixture with a slight excess of the R-enantiomer. PMID:23369033

Stoye, Alexander; Peez, Theodor Edmund; Opatz, Till



Indole Alkaloids from Marine Sources as Potential Leads against Infectious Diseases  

PubMed Central

Indole alkaloids comprise a large and complex class of natural products found in a variety of marine sources. Infectious diseases remain a major threat to public health, and in the absence of long-term protective vaccines, the control of these infectious diseases is based on a small number of chemotherapeutic agents. Furthermore, the emerging resistance against these drugs makes it urgently necessary to discover and develop new, safe and, effective anti-infective agents. In this regard, the aim of this review is to highlight indole alkaloids from marine sources which have been shown to demonstrate activity against infectious diseases.

Franca, Paulo H. B.; Barbosa, Daniel P.; da Silva, Daniel L.; Ribeiro, Eurica A. N.; Santana, Antonio E. G.; Santos, Barbara V. O.; Barbosa-Filho, Jose M.; Quintans, Jullyana S. S.; Barreto, Rosana S. S.; Quintans-Junior, Lucindo J.; de Araujo-Junior, Joao X.



A review on indole alkaloids isolated from Uncaria rhynchophylla and their pharmacological studies.  


Uncaria rhynchophylla (Miq.) Jacks, Rubiaceae, is one of the original plants of the important Chinese crude drug, Gou-teng, mainly used for the treatment of convulsion, hypertension, epilepsy, eclampsia, and cerebral diseases. The pharmacological activities of this plant are related to the presence of active compounds predominantly indole alkaloids. In this article, we have reviewed some reports about the pharmacological activities of the main indole alkaloids isolated from U. rhynchophylla. This review paper will contribute to the studies on the chemistry, safety and quality control of medicinal preparations containing Uncaria species. PMID:23376412

Ndagijimana, Andre; Wang, Xiaoming; Pan, Guixiang; Zhang, Fan; Feng, Hong; Olaleye, Olajide



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.

Naumann, Claudia; Hartmann, Thomas; Ober, Dietrich



Alkaloids from the Mangrove-Derived Actinomycete Jishengella endophytica 161111  

PubMed Central

A new alkaloid, 2-(furan-2-yl)-6-(2S,3S,4-trihydroxybutyl)pyrazine (1), along with 12 known compounds, 2-(furan-2-yl)-5-(2S,3S,4-trihydroxybutyl)pyrazine (2), (S)-4-isobutyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (3), (S)-4-isopropyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (4), (4S)-4-(2-methylbutyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (5), (S)-4-benzyl-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde (6), flazin (7), perlolyrine (8), 1-hydroxy-?-carboline (9), lumichrome (10), 1H-indole-3-carboxaldehyde (11), 2-hydroxy-1-(1H-indol-3-yl)ethanone (12), and 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (13), were isolated and identified from the fermentation broth of an endophytic actinomycetes, Jishengella endophytica 161111. The new structure 1 and the absolute configurations of 2–6 were determined by spectroscopic methods, J-based configuration analysis (JBCA) method, lactone sector rule, and electronic circular dichroism (ECD) calculations. Compounds 8–11 were active against the influenza A virus subtype H1N1 with IC50 and selectivity index (SI) values of 38.3(±1.2)/25.0(±3.6)/39.7(±5.6)/45.9(±2.1) ?g/mL and 3.0/16.1/3.1/11.4, respectively. The IC50 and SI values of positive control, ribavirin, were 23.1(±1.7) ?g/mL and 32.2, respectively. The results showed that compound 9 could be a promising new hit for anti-H1N1 drugs. The absolute configurations of 2–5, 13C nuclear magnetic resonance (NMR) data and the specific rotations of 3–6 were also reported here for the first time.

Wang, Pei; Kong, Fandong; Wei, Jingjing; Wang, Yi; Wang, Wei; Hong, Kui; Zhu, Weiming



Enrichment and purification of six Aconitum alkaloids from Aconiti kusnezoffii radix by macroporous resins and quantification by HPLC-MS.  


Aconitine, mesaconitine, hypaconitine, benzoylaconine, benzoylmesaconine and benzoylhypaconine are six main Aconitum alkaloids from traditional Chinese medicine, Aconiti kusnezoffii radix, which possess highly bioactive as well as highly toxic character for medicinal use. In the present study, for the purpose of better utilizing the toxic herbal material, the performance characteristics of NKA-II, D101, X-5, AB-8, S-8, HPD722 and HPD750 macroporous resins for the enrichment and purification of these six Aconitum alkaloids were critically evaluated. Results showed that NKA-II offered the best adsorption and desorption capacities for six Aconitum alkaloids among the seven macroporous resins tested, which were affected significantly by the pH value. Subsequently, dynamic adsorption and desorption experiments had been carried out with the column packed by NKA-II resin to optimize the separation process of six Aconitum alkaloids. After one run treatment with NKA-II resin, the content of total six Aconitum alkaloids were increased from 5.87% to 60.3%, the recovery was 75.8%. Meanwhile, a validated HPLC-MS method had been developed to qualitative and quantitative these six Aconitum alkaloids. This method would provide scientific references to the large-scale production of six Aconitum alkaloids from Aconiti kusnezoffii radix or other plants and might also expand the secure application of these highly toxic components for pharmacy. PMID:24814003

Liu, Jingjing; Li, Qing; Liu, Ran; Yin, Yidi; Chen, Xiaohui; Bi, Kaishun



Towards a Molecular Understanding of the Biosynthesis of Amaryllidaceae Alkaloids in Support of Their Expanding Medical Use  

PubMed Central

The alkaloids characteristically produced by the subfamily Amaryllidoideae of the Amaryllidaceae, bulbous plant species that include well know genera such as Narcissus (daffodils) and Galanthus (snowdrops), are a source of new pharmaceutical compounds. Presently, only the Amaryllidaceae alkaloid galanthamine, an acetylcholinesterase inhibitor used to treat symptoms of Alzheimer’s disease, is produced commercially as a drug from cultivated plants. However, several Amaryllidaceae alkaloids have shown great promise as anti-cancer drugs, but their further clinical development is restricted by their limited commercial availability. Amaryllidaceae species have a long history of cultivation and breeding as ornamental bulbs, and phytochemical research has focussed on the diversity in alkaloid content and composition. In contrast to the available pharmacological and phytochemical data, ecological, physiological and molecular aspects of the Amaryllidaceae and their alkaloids are much less explored and the identity of the alkaloid biosynthetic genes is presently unknown. An improved molecular understanding of Amaryllidaceae alkaloid biosynthesis would greatly benefit the rational design of breeding programs to produce cultivars optimised for the production of pharmaceutical compounds and enable biotechnology based approaches.

Takos, Adam M.; Rook, Fred



Cyclopeptide alkaloid fraction from Zizyphi Spinosi Semen enhances pentobarbital-induced sleeping behaviors  

Microsoft Academic Search

This study aimed to investigate effects of cyclopeptide alkaloid fraction of ZSS (CAFZ) on pentobarbital-induced sleeping behaviors and to determine whether these effects were mediated by ?-aminobutyric acid (GABA) receptors Cl? channel activation, using a Western blot technique and Cl? sensitive fluorescence probe. GABA receptors subunits expression and Cl? influx were investigated in cultured cerebellar granule cells. CAFZ shortened sleeping

Yuan Ma; Huishan Han; Sang-Yoon Nam; Yun-Bae Kim; Jin-Tae Hong; Yeo-Pyo Yun; Ki-Wan Oh



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


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