Two stilbenoids from the orchid arundina bambusifolia
TL;DR: Arundin and arundinin were shown to be 3-hydroxy-2,6-bis-( p -hydroxybenzyl)-5-methoxybibenzyl and 3,3′-dihydroxy-4-( p-HydroxybenZyl)- 5-mETHoxybiberenzyl, respectively, mainly from spectral evidence.
Abstract: From the orchid, Arundina bambusifolia, were isolated two new stilbenoids, arundin and arundinin, besides p-hydroxybenzaldehyde, batatasin III, lusianthridin, flavanthrin, flavidin and the polyphenyl propanoid-malonate-derived compound 3,3′-dihydroxy-2,6-bis-(p-hydroxybenzyl)-5-methoxybibenzyl of previously known structures. Arundin and arundinin were shown to be 3-hydroxy-2,6-bis-(p-hydroxybenzyl)-5-methoxybibenzyl and 3,3′-dihydroxy-4-(p-hydroxybenzyl)-5-methoxybibenzyl, respectively, mainly from spectral evidence.
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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...
49 citations
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TL;DR: Nine new phenanthrenes (1-9) and a new benzyl glycoside (10) together with 45 known compounds were isolated from the rhizomes of Bletilla formosana for their anti-inflammatory activities and inhibition of superoxide anion generation and elastase release.
Abstract: Nine new phenanthrenes (1–9) and a new benzyl glycoside (10) together with 45 known compounds were isolated from the rhizomes of Bletilla formosana. The structures of 1–10 were elucidated primarily on the basis of their 1D and 2D NMR spectroscopic data. Most of the isolated compounds were evaluated for their anti-inflammatory activities. The results showed that IC50 values for the inhibition of superoxide anion generation and elastase release ranged from 0.2 to 6.5 μM and 0.3 to 5.7 μM, respectively. Structure–activity relationships of the isolated compounds were also investigated. The inhibitory potencies were determined as phenanthrenes > bibenzyls > biphenanthrenes.
27 citations
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TL;DR: A chemical investigation of the Orchidaceae Arundina gramnifolia has led to the isolation of a novel stilbenoid, named arundinan, which has been elucidated as 2-hydroxybenzyl)-3-Hydroxy-5-methoxybibenzyl on the basis of physical and chemical evidence and spectral analysis.
Abstract: A chemical investigation of the Orchidaceae Arundina gramnifolia has led to the isolation of a novel stilbenoid, named arundinan (1). The structure of 1 has been elucidated as 2-(p-hydroxybenzyl)-3-hydroxy-5-methoxybibenzyl on the basis of physical and chemical evidence and spectral analysis.
26 citations
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TL;DR: A review of the literature on orchids that are used in traditional medicine has been reviewed in this work indicating a great potential of such organisms as source of chemical entities for the development of new drugs as mentioned in this paper.
Abstract: The Orchidaceae family is the largest group of flowering plants in the Angiosperm monocotyledons spread on our planet. Its members, called orchids, are herbs or epiphytes with showy flowers distributed mainly in tropical regions. Several classes of phytoconstituents have been so far isolated from therapeutically-used orchids showing a great chemical diversity. Among them, phenolic derivatives have been studied for their biological activities, especially in the field of cancer, inflammation, and neurodegeneration. On the other hand, limited information has been so far obtained on the numerous alkaloids and terpenoids isolated from several orchid species. Recent articles revealed pronounced effects of some alkaloids on the CNS. Published literature on orchids that are used in traditional medicine has been reviewed in this work indicating a great potential of such organisms as source of chemical entities for the development of new drugs.
25 citations
References
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TL;DR: In this paper, three new bibenzyls and two dihydrophenanthrenes, which exhibit antimicrobial activity, were isolated from tubers of Bletilla striata.
Abstract: Three new bibenzyls and two new dihydrophenanthrenes, which exhibit antimicrobial activity, were isolated from tubers of Bletilla striata. They were identified by various spectroscopic methods.
107 citations
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TL;DR: Moscatilin, a new bibenzyl derivative isolated from the orchid Dendrobium moscatum, was shown to have the structure 4,4′-dihydroxy-3,3′,5-trimethoxybibensyl.
Abstract: Moscatilin, a new bibenzyl derivative isolated from the orchid Dendrobium moscatum , was shown to have the structure 4,4′-dihydroxy-3,3′,5-trimethoxybibenzyl.
76 citations
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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.
Abstract: Two 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, coelonin and gigantol have been isolated and characterized. The three new compounds are 1-(4′-hydroxy-3′,5′-dimethoxyphenyl)-2-(3″-hydroxyphenyl)ethane, 1-(4′-hydroxy-3′,5′-dimethoxyphenyl)-2-(4″-hydroxy-3″-methoxyphenyl)ethane and 2,7-dihydroxy-4,6-dimethoxy-9,10-dihydrophenanthrene.
64 citations
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TL;DR: Lusianthrin and lusian-thridin, two new stilbenoids, were isolated from the orchid Lusia indivisa.
Abstract: Lusianthrin and lusianthridin, two new stilbenoids, were isolated from the orchid Lusia indivisa . The structures of lusianthrin and lusianthridin were established from detailed spectral and chemical evidence.
61 citations
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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.
Abstract: Flavanthrin, the first dimeric 9,10-dihydrophenanthrene derivative, was isolated from the orchid Eria flava which also yielded the previously reported 9,10-dihydrophenanthrene coelonin ( 2a ). The structure of flavanthrin was established as the 1.1'-dimer ( 1a ) of its congener coelonin from spectral and chemical evidence.
51 citations