A ring-B oxygenated phenanthrene derivative from the orchid Bulbophyllum gymnopus
TL;DR: Gymnopusin, the first naturally occurring phenanthrene derivative having a hydroxyl group at C-9, was isolated from the orchid Bulbophyllum gymnopus.
Abstract: Gymnopusin, the first naturally occurring phenanthrene derivative having a hydroxyl group at C-9, was isolated from the orchid Bulbophyllum gymnopus . It was shown to be 7,9-dihydroxy-2,3,4-trimethoxyphenanthrene ( 1a ) mainly from the spectral data of the compound and those of its diacetyl ( 1b ) and dimethyl ether ( 1c ) derivatives.
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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.
Abstract: The aim of this review is to survey the various naturally occurring phenanthrene compounds that have been isolated from different plants. Only one review has previously been published on this topic. Gorham (1989) reviewed the structures, biosynthesis, separations and spectroscopy of stilbenes and phenanthrenes.
The present study furnishes an overview of the hydroxy or/and methoxy-substituted 9,10-dihydro/phenanthrenes, methylated, prenylated and other monomeric derivatives, dimeric and trimeric phenanthrenes and their biological activities.
A fairly large number of phenanthrenes have been reported from higher plants, mainly in the Orchidaceae family, in the species Dendrobium, Bulbophyllum, Eria, Maxillaria, Bletilla, Coelogyna, Cymbidium, Ephemerantha and Epidendrum. A few phenanthrenes have been found in the Hepaticae class and Dioscoreaceae, Combretaceae and Betulaceae families. Their distribution correlates strongly with the taxonomic divisions.
These plants have often been used in traditional medicine, and phenanthrenes have therefore been studied for their cytotoxicity, antimicrobial, spasmolytic, anti-inflammatory, antiplatelet aggregation, antiallergic activities and phytotoxicity.
On the basis of 120 references, this review covers the phytochemistry and pharmacology of phenanthrenes, describing 252 compounds. This contribution stems from our work on the medicinal plant Tamus communis.
282 citations
TL;DR: Two new phenanthrenes (4,9-dimethoxyphenanthrene-2,5-diol and 4,6-dimethyltoxymethylhexane-1,3,7-triol) and two new 9,10-dihydrophenanthreness (4methoxy-9, 10-dibenzyls and the triterpenoid friedelin were isolated and characterized from the hexane extract of the orchid Bulbophyllum vaginatum) were determined by spectroscopic analyses
Abstract: Two new phenanthrenes (4,9-dimethoxyphenanthrene-2,5-diol and 4,6-dimethoxyphenanthrene-2,3,7-triol) and two new 9,10-dihydrophenanthrenes (4-methoxy-9,10-dihydrophenanthrene-2,3,7-triol and 4,6-dimethoxy-9,10-dihydrophenanthrene-2,3,7-triol), along with six known phenanthrenes, four known 9,10-dihydrophenanthrenes no known bibenzyls and the triterpenoid friedelin were isolated and characterized from the hexane extract of the orchid Bulbophyllum vaginatum. The structures of these compounds were determined by spectroscopic analyses.
94 citations
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.
66 citations
TL;DR: A phytochemical study of the whole plant of Bulbophyllum odoratissimum (J.E. Smith) Lindl (Orchidaceae) and cytotoxicity measurement of its isolated compounds have been carried out and all compounds, except for 9, have not been reported in this plant before.
Abstract: A phytochemical study of the whole plant of Bulbophyllum odoratissimum (J.E. Smith) Lindl (Orchidaceae) and cytotoxicity measurement of its isolated compounds have been carried out. The ethyl acetate extract yielded nine phenolics, identified as moscatin ( 1 ), 7-hydroxy-2,3,4-trimethoxy-9,10-dihydrophenanthrene ( 2 ), coelonin ( 3 ), densiflorol B ( 4 ), gigantol ( 5 ), batatasin III ( 6 ), tristin ( 7 ), vanillic acid ( 8 ) and syringaldehyde ( 9 ). Compounds 4 and 8 were discovered in the Bulbophyllum genus for the first time and all compounds, except for 9, have not been reported in this plant before. The isolated compounds were evaluated in vitro for their inhibitory ability against the growth of human leukaemia cell lines K562 and HL-60, human lung adenocarcinoma A549, human hepatoma BEL-7402 and human stomach cancer SGC-7901. Densiflorol B ( 4) the most active compound, exhibited IC 50 values of 0.08–3.52 μg/ml against the five tested cell lines.
66 citations
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...…ygchen48@hotmail.com (Y. Chen), qingchenhh@ yeah.net (C. Qing). rison, 2004; Leong, Harrison, & Powell, 1999; Leong, Kang, Harrison, & Powell, 1997; Majumder & Banerjee, 1989; Majumder, Kar, & Shoolery, 1985; Majumder, Pal, & Majumder, 1999; Majumder, Roychowdhury, & Chakraborty, 1997; Wu, He, &…...
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References
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TL;DR: In this article, the 13 C NMR spectra of 15 neolignans of several structural types and two lignans were analyzed and their carbon shifts assigned, and the shifts of pyrogallol ether and ethyl phenyl carbinyl ether models were used in this connection.
Abstract: The 13 C NMR spectra of 15 neolignans of several structural types and two lignans were analyzed and their carbon shifts assigned. The shifts of pyrogallol ether and ethyl phenyl carbinyl ether models were used in this connection. The stereochemistry of a dimeric sideproduct in the preparation of the latter models was determined by 13 C NMR analysis.
96 citations
TL;DR: An amorphous phenanthrene, named nudol has been isolated from Eulophia nuda, Eria carinata and E. stricta and was identified as 2,7-dihydroxy-3,4-dimethoxyphenanthrene.
Abstract: An amorphous phenanthrene, named nudol has been isolated from Eulophia nuda , Eria carinata and E. stricta . It was identified as 2,7-dihydroxy-3,4-dimethoxyphenanthrene. Synthesis of nudol and its dimethyl ether is described.
74 citations
TL;DR: Two new polyoxygenated phenanthrene derivatives, confusarin and confusaridin, are isolated from the orchid Eria confusa and are shown to be 2,7-dihydroxy-3,4,8-trimethoxyphenanthrene and 2,6- dihydrox-2,6,7, 8-tetramethoxyrene, respectively.
Abstract: From the orchid Eria confusa were isolated two new polyoxygenated phenanthrene derivatives, confusarin and confusaridin, which were shown to be 2,7-dihydroxy-3,4,8-trimethoxyphenanthrene and 2,6-dihydroxy-3,4,7,8-tetramethoxyphenanthrene, respectively.
46 citations
TL;DR: Bulbophyllanthrin, a novel phenanthrene derivative from the orchid B. leopardium, was shown to have the structure 1a mainly on the basis of spectral evidence including 13 C and 2D NMR spectra as discussed by the authors.
Abstract: Bulbophyllanthrin, a novel phenanthrene derivative from the orchid Bulbophyllum leopardium , was shown to have the structure 1a mainly on the basis of spectral evidence including 13 C and 2D NMR spectra.
43 citations
37 citations