Alkaloidal constituents ofpeganum harmala and synthesis of the minor alkaloid deoxyvascinone
TL;DR: In this paper, a new synthesis of deoxyvascinone has been achieved from anthranilic acid and γ-aminobutyric acid, for which a plausible structure has been postulated from spectral evidences.
About: This article is published in Phytochemistry.The article was published on 1968-02-01. It has received 30 citations till now. The article focuses on the topics: Harmine & Harmaline.
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TL;DR: The simple β-carbolines are presented as a distinct group of alkaloids displaying structural modification of three basic ring systems and aspects of their metabolism, pharmacological properties and taxonomic significance are briefly summarized.
253 citations
TL;DR: A facile synthesis of bronchodilatory pyrrolo[2,1-b]quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast and synthesis and resolution of vasicinone has been carried out by employing different lipases.
Abstract: A facile synthesis of bronchodilatory pyrrolo[2,1-b]quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl−NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.
78 citations
TL;DR: One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinone-derived alkaloids from anthranilic acid, corresponding lactam and SOCl(2) is described, which can be applicable to the synthesis of simple 4( 3H)quinazolone- derived alkalids, such as lu serotonin A, tryptanthrin, and rutaecarpine.
Abstract: One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl(2) is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.
50 citations
TL;DR: This study revealed that total alkaloids from seeds of the medicinal plant Peganum harmala L. harmala possessed significant growth inhibitory effect on four treated plants, with dicot plants being more sensitive than the tested monocot plants.
Abstract: 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.
42 citations
TL;DR: Glycosidic patterns elucidated range from mono- to tri-glycosides, five of which are novel in plants, and the importance of those cited in the literature has been surveyed in relation to the chemosystematics of the Zygophyllaceae.
37 citations
References
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TL;DR: Reserpine, C33H40O9N2, has been isolated from Rauwolfia serpentina Benth as discussed by the authors and is an ester alkaloid yielding reserpic acid, 3,4,5-trimethoxybenzoic acid and methanol on hydrolysis.
Abstract: Reserpine, C33H40O9N2, has been isolated from Rauwolfia serpentina Benth. Reserpine is an ester alkaloid yielding reserpic acid, 3,4,5-trimethoxybenzoic acid and methanol on hydrolysis. Degradation products of reserpic acid make it likely that reserpic acid is a yohimbane derivate, and a hypothetical structure for reserpine has been put forward which is in agreement with the facts known so far.
62 citations
TL;DR: In this paper, three minor alkaloids from Glycosmis arborea (Roxb) DC, viz glycosmicine, glycorine and glycosminine, have been assigned the following structures: 1-methyl-2-keto-1,2-dihydro-4-quinazolone (II), 1 -methyl-4 -quinazolate (V) and 2-benzyl -4 -quinazolate(XIII), respectively.
49 citations
33 citations
24 citations