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Journal ArticleDOI

The structure and stereochemistry of murrangatin : A new monomeric coumarin from Murraya elongata Alph. DC.☆

01 Jan 1973-Tetrahedron (Pergamon)-Vol. 29, Iss: 18, pp 2811-2814
TL;DR: The structure of murrangatin, a monomeric coumarin isolated from the leaves of Murraya elongata, has been elucidated by spectroscopic and chemical evidence, and confirmed by its chemical correlation with phebalosin this article.
About: This article is published in Tetrahedron.The article was published on 1973-01-01. It has received 20 citations till now.
Citations
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Journal ArticleDOI
TL;DR: The biogenesis, structural diversity and distribution of simple, furano- and pyranocoumarins in the Rutaceae is reviewed and the potential value of these compounds as taxonomic markers and their possible functions are discussed.

134 citations

Book ChapterDOI
TL;DR: 7-hydroxycoumarin [umbelliferone, (2)], one of the most widely distributed coumarins, is often regarded as the parent, in a structural sense and also biogenetically, of a large number of the structurally more complex coumarin.
Abstract: Over the past 150 years, since Vogel in 1820 isolated the parent oxygen heterocycle, coumarin (1) from Coumarouna odorata = Dipteryx odorata (1), coumarins have been recognized as widely distributed plant products. The vast majority carry an oxygen substituent at C-7; consequently 7-hydroxycoumarin [umbelliferone, (2)], one of the most widely distributed coumarins, is often regarded as the parent, in a structural sense and also biogenetically, of a large number of the structurally more complex coumarins. A number of review articles on natural plant coumarins have appeared (154, 302, 344, 420, 525, 541, 548) since the last in this series (153), the most comprehensive, albeit dealing solely with coumarins of the Umbelliferae, being that of Nielsen in 1970 (419).

77 citations

Journal ArticleDOI
TL;DR: The structural determination of five new coumarins: murralonginol isovalerate (1b), isomurralonlin isovalite (2b), murrangatin isovaline (6b), minumicrolin isomorphine (7b), chloculol (4a), and paniculoline (18) is described in this article.
Abstract: The structural determination of five new coumarins: murralonginol isovalerate (1b), isomurralonginol isovalerate (2b), murrangatin isovalerate (6b), minumicrolin isovalerate (7b), chloculol (4a), and a new indole alkaloid, paniculol (18), is described.The relative configurations hitherto reported for the α-glycol moieties in murrangatin (erythro) and minumicrolin (threo) have been revised to threo for compound (6a) and erythro for compound (7a), respectively on the basis of NOE experiments performed on the acetonides (6e) and (7e). Furthermore, the absolute configuration of (–)-murrangatin (6a) has been shown to be [R,R] by analysis of the CD spectrum of tetrahydromurrangatin dibenzoate (16b). The reaction of phebalosin (8) with hydrochloric acid has also been re-examined.

46 citations

Journal ArticleDOI
TL;DR: An examination of the roots of Murraya for the presence of the dimeric indole yuehchukene has revealed a dichotomy in the genus between species producing this alkaloid and those producing the carbazole alkaloids girinimbine, with no apparent overlap between the two groups of species.

43 citations

References
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Journal ArticleDOI
TL;DR: In this article, 7-Methoxy-8-(2-hydroxy)-3-methyl-3-butenyl)-coumarin has been isolated from bitter orange oil and named auraptenol.

31 citations

Journal ArticleDOI
TL;DR: In this article, the coumarin phebalosin, obtained from Phebalium tuberculosum and P. drummondii, has been assigned to the structure (II) of the Coumarin.
Abstract: The structure (II) has been assigned to the coumarin phebalosin, obtained from Phebalium tuberculosum and P. drummondii.

31 citations

Journal ArticleDOI
TL;DR: NMR, IR, UV, mass spectral and analytical data are presented in support of the constitution of Coumarin and(3,6-dimethyl-6-formyl-2-heptenyl)oxyl-psoralen and 7-methoxy-8-methyl-propyl-coumarin.

25 citations