Showing papers on "Indole alkaloid published in 2011"
62 citations
TL;DR: Phytochemical research on Alstonia rostrata revealed a potential new precursor for monoterpenoid indole alkaloids and isolated the alstrostines A and B, and it was determined that they were derived from tryptophan and secologanin in a 1:2 ratio, which supported the presence of a new type of MIA precursor.
49 citations
TL;DR: Three indole alkaloids and a new alkaloid, 5-hydroxy-3,6-oxidovoacangine, isolated from Voacanga africana were found to exhibit potent cannabinoid CB1 receptor antagonistic activity, the first example of CB1 antagonists derived from natural alkal steroids.
30 citations
TL;DR: In this paper, the first asymmetric total synthesis of cyclopiazonic acid by a modification of the Knight synthesis was reported, which is the most efficient route to CPA.
25 citations
Journal Article•
TL;DR: The low light treatment with plastic film accelerated the accumulation of V BL in the leaves of C. roseus seedlings, which may have practical significance in the production of VBL.
Abstract: Catharanthus roseus (L.) G. Don, an important medicinal plant, produces the powerful alkaloids vinblastine (VBL) and vincristine (VCR), which are known for their remarkable inhibitory activity against tumor cells. This paper is the result of a study on the effects of low light/UV light on the contents of chlorophyll and alkaloids, and on the expression of terpenoid indole alkaloids (TIAs) biosynthesis pathway genes in the leaves of aseptic C. roseus seedlings. A plastic film treatment first induced a slight increase and then a significant decrease (p＜0.05) in the total chlorophyll content, and a lower chlorophyll a/b ratio. The amounts of vindoline (VIN) and catharanthine (CAT) followed the identical pattern under plastic film but the content of VBL, generated by its precursors VIN and CAT, increased gradually until reaching a maximum (0.028 mg g^(-1)±0.0051) on the 15th day of treatment. The plastic film also induced the expression changes of TIA biosynthesis pathway genes. The further correlation analysis between alkaloid content and these genes transcriptional levels indicated that VIN accumulation was significantly correlated with the gene expression of desacetoxyvindoline-4-hydroxylase (D4h) and deacetylvindoline-4-O-acetyl transferase (Dat), and CAT accumulation was significantly correlated with strictosidine synthase (Str) gene expression (p＜0.05). Therefore, the low light treatment with plastic film accelerated the accumulation of VBL in the leaves of C. roseus seedlings, which may have practical significance in the production of VBL.
19 citations
TL;DR: The leaves of Mitragyna inermis (Willd.) O. Kuntze have been examined for alkaloids and shown to contain routundifoline, isorotund ifoline, rhynchophylline, isorbethine, ciliaphylline, Rhynchociline, speciophyllines, and traces of a second indole alkaloid which appears to be of the corynanthine type.
Abstract: The leaves of Mitragyna inermis (Willd.) O. Kuntze have been examined for alkaloids and shown to contain routundifoline, isorotundifoline, rhynchophylline, isorhynchophylline, ciliaphylline, rhynchociline, speciophylline, a small amount of uncarine F, mitraciliatine and traces of a second indole alkaloid which appears to be of the corynanthine type. There is also a polar compound present, Dragendorff positive, which remains on the base line when subjected to thin-layer chromatography with the usual solvent systems used for the mitragyna alkaloids.
18 citations
TL;DR: Two new indole alkaloids, bisnicalaterines and nicalaterine A, consisting of an eburnane and a corynanthe type of skeletons, showed potent antiplasmodial activity against Plasmodium falciparum 3D7.
17 citations
TL;DR: Two new monoterpenoid indole alkaloid derivatives and 11-methoxyjavaniside were found to effect relaxation of the supercoiled pBR322 plasmid DNA in the presence of Cu²+.
Abstract: Two new monoterpenoid indole alkaloid derivatives, turpiniside (1) and 11-methoxyjavaniside (2), along with the known alkaloids, vincosamide (3), (3 R)-pumiloside (4), and paratunamide C (5), were isolated from the leaves of Turpinia arguta (Lindl.) Seem. Their structures were determined on the basis of spectroscopic data. Compounds 1 and 3-5 were found to effect relaxation of the supercoiled pBR322 plasmid DNA in the presence of Cu²+.
16 citations
TL;DR: A new indole alkaloid; neonaucline (1), along with six known compounds–Cadamine, naucledine, harmane, benzamide, cinnamide and blumenol A–were isolated from the leaves of Ochreinauclea maingayii.
Abstract: 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.
15 citations
14 citations
TL;DR: A 3-alkylpyridinium-indole-2-carboxylate scaffold was found to exhibit antimicrobial activity against Bacillus subtilis.
TL;DR: The results show that biomimetic cyclization gave new polycyclic compounds similar to natural indole terpene alkaloids, and conclude that the stability of cation intermediates should determine the preference for product formation when using a Lewis acid.
Abstract: Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7-Epoxygeranyl)indole (11), 3-(10,11-epoxyfarnesyl)indole (2) and 3-(14,15-epoxygeranylgeranyl)indole (3) were respectively synthesized from geraniol, farnesol and geranylgeraniol in 6 or 7 steps. Four Lewis acids (MeAlCl(2), BF(3)·OEt(2), TiCl(4) and SnCl(4)) were applied for biomimetic cyclization of the synthesized epoxide precursors. The cyclization products (one product from 11, four products from 2, and three products from 3) were isolated after separation by chromatography. Their structures were determined by using NMR (COSY, HSQC, HMBC, NOESY, etc.) and HRMS analyses. The results show that biomimetic cyclization gave new polycyclic compounds similar to natural indole terpene alkaloids. We conclude that the stability of cation intermediates should determine the preference for product formation by biomimetic cyclization when using a Lewis acid.
TL;DR: One rare tetracyclic macroline-type indole alkaloid, named rauvoyunine A (1), and two new picraline-type alkaloids rauvonunines B and C (2 and 3) were isolated from the aerial parts of Rauvolfia yunnanensis and their structures were elucidated on the basis of extensive spectroscopic analysis as discussed by the authors.
Abstract: One rare tetracyclic macroline-type indole alkaloid, named rauvoyunine A (1), and two new picraline-type alkaloids rauvoyunines B and C (2 and 3) were isolated from the aerial parts of Rauvolfia yunnanensis. Their structures were elucidated on the basis of extensive spectroscopic analysis. Compounds 2 and 3 were evaluated for their in vitro cytotoxicity against five human tumor cell lines.
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TL;DR: Two pairs of epimeric indole alkaloids with a chlorine atom were isolated from the aerial part of Catharanthus roseus and their structures were established on the basis of the spectroscopic data including UV, IR, HRESIMS, NMR, and X-ray diffraction analyses.
Abstract: Two pairs of epimeric indole alkaloids (1- 4) with a chlorine atom were isolated from the aerial part of Catharanthus roseus. Their structures were established on the basis of the spectroscopic data including UV, IR, HRESIMS, NMR, and X-ray diffraction analyses. The cytotoxic activities of 1-4 against the HepG2 cell line were evaluated.
TL;DR: One bis(monoterpenoid) indole alkaloid glucoside, hirsutaside D (1), along with three known compounds, bahienoside A (2), bahienside B (3) and neonaucleoside B(4), were isolated from the leaves of U. hirsuta and the structure of compound 1 was elucidated on the basis of extensive spectroscopic data analysis and chemical means.
TL;DR: Deformylflustrabromine, a marine indole alkaloid, was synthesized from 6-bromotryptamine, a plausible biosynthetic precursor, without protection of the amino group by a two-step reverse prenylation.
Abstract: Deformylflustrabromine, a marine indole alkaloid, was synthesized from 6-bromotryptamine, a plausible biosynthetic precursor, without protection of the amino group by a two-step reverse prenylation...
Patent•
16 Nov 2011TL;DR: The use of indole alkaloid compounds of formula I, for example, pubescine, and the use of such compounds and compositions thereof to promote melanogenesis and pigmentation is discussed in this article.
Abstract: Provided are indole alkaloid compounds of formula I, for example, pubescine, and the use of such compounds and compositions thereof to promote (e.g., enhance) melanogenesis and pigmentation. Also provided are plant extracts containing a compound of formula I, for example, pubescine, and the use of such a plant extract to promote (e.g., enhance) melanogenesis and pigmentation. The compound or plant extract may be prepared as pharmaceutical and cosmetic compositions, and may be used for the prevention and treatment of conditions that are related to aberrant melanogenesis activity.