Dimeric phenanthrenes from the orchid Bulbophyllum reptans
TL;DR: In this paper, Reptanthrin and isoreptanthrin, two new dimeric phenanthrenes, were isolated from the orchid Bulbophyllum reptans which also afforded nine known stilbenoids, viz.
About: This article is published in Phytochemistry.The article was published on 1999-03-10. It has received 41 citations till now. The article focuses on the topics: Bulbophyllum reptans & Gymnopusin.
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TL;DR: The present study furnishes an overview of the hydroxy or/and methoxy-substituted 9,10-dihydro/phenanthrene, methylated, prenylated and other monomeric derivatives, dimeric and trimeric phenanthrenes and their biological activities.
282 citations
TL;DR: Compounds 1-3 and denthyrsinin (1,5,7-trimethoxyphenanthrene-2,6-diol; 4) showed significant cytotoxic activities against Hela (13.5, 9.5 and 4.8 microM, respectively) cell lines.
79 citations
Cites background from "Dimeric phenanthrenes from the orch..."
...an asymmetrical dimeric phenanthrene derivative by comparison with analogous compounds (Majumder and Lahiri, 1990; Majumder et al., 1998, 1999 )....
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...A fairly large number of phenanthrenes and 9,10dihydrophenanthrenes were reported from a series of orchids, e.g., Dendrobium (Lee et al., 1995), Bulbophyllum ( Majumder et al., 1999 ), Eria (Bhandari et al., 1985), Lusia (Majumder and Lahiri, 1990), Maxillaria (Estrada et al., 1999) et al. Four symmetric dimeric phenanthrenes were reported early from Orchid Cirrhopetalum maculosum (Majumder et al., 1990), Bulbophyllum reptans (Majumder et ......
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TL;DR: Six newphenanthrene derivatives, including three monophenanthrenes (1-3), two biphenanholdes (4 and 5), and a triphenanthrene (6), have been isolated from an ethanolic extract of the tubers of Cremastra appendiculata.
Abstract: Six newphenanthrene derivatives, including three monophenanthrenes (1-3), two biphenanthrenes (4 and 5), and a triphenanthrene (6), have been isolated from an ethanolic extract of the tubers of Cremastra appendiculata. Using spectroscopic methods, the structures of compounds 1-6 were determined as 1-hydroxy-4,7-dimethoxy-1-(2-oxopropyl)-1H-phenanthren-2-one (1), 1,7-dihydroxy-4-methoxy-1-(2-oxopropyl)-1H-phenanthren-2-one (2), 2-hydroxy-4,7-dimethoxyphenanthrene (3), 2,7,2'-trihydroxy-4,4',7'-trimethoxy-1,1'-biphenanthrene (4), 2,2'-dihydroxy-4,7,4',7'-tetramethoxy-1,1'-biphenanthrene (5), and 2,7,2',7',2' '-pentahydroxy-4,4',4' ',7' '-tetramethoxy-1,8,1',1' '-triphenanthrene (6), respectively. Compounds 1-6 and two known compounds, cirrhopetalanthin (7) and flavanthrinin (8), obtained previously from this plant, were evaluated against six human cancer cells and a normal cell line.
77 citations
TL;DR: Stilbenoids are formed by a particular branch of the flavonoid biosynthetic pathway and are of special interest to natural product researchers for their roles in plant resistance to fungal pathogens and their biological effects as discussed by the authors.
Abstract: Stilbenoids are formed by a particular branch of the flavonoid biosynthetic pathway. They are of special interest to natural product researchers for their roles in plant resistance to fungal pathogens and their biological effects. This review in the volume of Bioactive Natural Products provides a comprehensive account of the occurrence, chemistry, biological roles and activities of the stilbenoids. Nearly 800 stilbenoids, isolated from natural sources in the recent 12 years, are grouped into structural types and discussed in terms of their reported pharmacological activity. The major groups of stilbenoids which are discussed in detail include stilbenes, bibenzyls, bisbibenzyls, phenanthrenoids, stilbene oligomers etc. Detailed tables and figures list the occurrence of stilbenoids in major plant species, and methods used for extracting and analyzing stilbenoids are discussed. Biosynthetic pathways and chemical synthesis are reviewed and the biological activities of stilbenoids are also addressed. The coverage of the new structures is from 1994 to 2006.
75 citations
References
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TL;DR: 2,7-Dihydroxy-4-methoxy-9,10-dihydrophenanthrene was isolated and identified from the whole plant of Coelogyne ochracea and C. elata.
77 citations
TL;DR: Three new substituted bibenzyls (1,2-diarylethanes) aloifol I and aloIFol II and a new substituted 9,10-dihydrophenanthrene, 6-O-methylcoelonin in addition to batatasin III, coel onin and gigantol have been isolated and characterized.
70 citations
TL;DR: Lusianthrin and lusian-thridin, two new stilbenoids, were isolated from the orchid Lusia indivisa.
66 citations
TL;DR: Flavanthrin, the first dimeric 9,10-dihydrophenanthrene derivative, was isolated from the orchid Eria flava which also yielded the previously reported 9, 10-dibhrenanthrene coelonin this paper.
54 citations
TL;DR: Cumulatin and tristin, two new bibenzyl derivatives, were isolated from the orchids Dendrobium cumulatum and Bulbophyllum triste, respectively.
53 citations