Thunalbene, a stilbene derivative from the orchid Thunia alba
TL;DR: Thunalbene, a new stilbene derivative, was isolated from the orchid Thunia alba which also afforded six known stilbenoids: batatasin-III, lusianthridin, 3,7-dihydroxy-2,4-dimethoxyphenanthrene, 3.5methoxystilbenoid and flavanthrin this paper.
About: This article is published in Phytochemistry.The article was published on 1998-12-20. It has received 50 citations till now.
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TL;DR: This review focuses on the distribution of stilbenes and 2-arylbenzofuran derivatives in the plant kingdom, the chemical structure of stILbenes in the Vitaceae family and their taxonomic implication.
288 citations
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: 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
TL;DR: It was found that blestriarene C and its 7,7'-diisopropyl ether 2 underwent rapid photoracemization even under ambient light exposure.
Abstract: A naturally occurring 1,1‘-biphenanthrene, blestriarene C (1), was prepared in 13 steps and 30% overall yield. The key steps are the ester-mediated nucleophilic aromatic substitution on 2,6-di-tert-butyl-4-methoxyphenyl 5-isopropoxy-2-methoxybenzoate (4) by 2-methoxy-4-methoxymethoxy-6-methylphenylmagnesium bromide (5) and a novel intramolecular cyclization of the resulting 4-isopropoxy-2‘-methoxy-4‘-methoxymethoxy-6‘-methylbiphenyl-2-carboxylic ester 14 to 7-isopropoxy-4-methoxy-2-(methoxymethoxy)phenanthren-9-ol (15). The racemic blestriarene C was optically resolved by chiral HPLC on a preparative scale to give several 10-mg yields of both the enantiomers in up to 95% ee. The absolute stereochemistry was determined to be Sa-(−) by the axial chirality recognition method, which was based on the stereospecific formation of a 12-membered cyclic diester containing two biaryl-o,o‘-diyl unites joined by ester −CO2− linkages. The validity of the method was confirmed by an X-ray crystallographic analysis and ab...
52 citations
TL;DR: The structures of coelogsinanthridin and coeloginanthrin were established as 3,5,7-trihydroxy-1,2-dimethoxy-9,10-dihydrophenanthrene and 3,4,5-triHydroxy-2,4-dimETHoxyphenanthene, respectively, which may have biological activities of phytoalexins and endogenous plant growth regulators.
45 citations
References
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19 citations
TL;DR: From stems of Phoenix dactylifera trans-3,5,3′,5′-tetrahydroxy-4-methoxystilbene has been isolated as a major component; cis-3.5, 3′, 5′-trans-5, 4′-trihydroxystilbenes were isolated as minor components.
19 citations
TL;DR: Isoflaccidinin and isooxoflaccidINin, new phenanthropyrone derivatives, isolated from the orchid Coelogyne flaccida were shown to be 2,7-dihydroxy-6-methoxy-5H-phenanthro [4,5-bcd] pyran-5-one and 2.7-dimethylpyrone pyron-5 -one, respectively, from spectral and chemical evidence as mentioned in this paper.
17 citations
TL;DR: Gnetin, a new stilbene isolated from Gnetum ula is assigned the structure 3,4-methylenedioxy-4′-methoxy- trans -stilbenes, 3 on the basis of spectroscopic data and synthesis as mentioned in this paper.
17 citations
TL;DR: A new dihydrochalcone derivative, lusianin, two other known chalcones and a phenanthrene derivative were isolated from the orchid Lusia volucris as mentioned in this paper.
17 citations