Convergent synthesis and preliminary biological evaluations of the stilbenolignan (±)-aiphanol and various congeners

Banwell, Martin G.; Bezos, Anna; Chand, Satish; Dannhardt, Gerd; Kiefer, Werner; Nowe, Ulrike; Parish, Christopher R.; Savage, G. Paul; Ulbrich, Holger

doi:10.1039/b305106d

Cited by 23 publications

(11 citation statements)

References 16 publications

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“…Stilbenes-or 1,2-diphenylethylenes, of which more than 300 are known-are biologically active compounds that have shown different activities, such as nitric oxide production inhibition and antibacterial, antifungal, antioxidant, anti-inflammatory, anticancer, and antimalarial activities (123)(124)(125)(126)(127)(128). These compounds and/or their glycosides also have attracted much attention for their biological effects, including antioxidant cyclooxygenase-I and -II inhibitory (129), antiplatelet-aggregation (130), antifungal (131), tyrosinase-inhibitory (132), anti-HIV-1, and cytotoxic effects (133), which play an important role in photochemical reactions (134,135). They have been found in many families of higher plants but mainly in Vitaceae, Gnetaceae, Polygonaceae, Liliaceae, Moraceae, and Cyperaceae.…”

Section: Stilbenesmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites

Dembitsky

2005

Lipids

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This review article presents 342 aromatic glycosides, isolated from and identified in plants and microorganisms, that demonstrate different biological activities. They are of great interest, especially for the medicinal and/or pharmaceutical industries. These biologically active natural surfactants are good prospects for the future chemical preparation of compounds useful as antioxidant, anticancer, antimicrobial, and antibacterial agents. These glycosidic compounds have been classified into several groups, including simple aromatic compounds, stilbenes, phenylethanoids, phenylpropanoids, naphthalene derivatives, and anthracene derivatives.

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Section: Stilbenesmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites

Dembitsky

2005

Lipids

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“…The coupling constant (J 7Љ,8Љ ϭ8.5 Hz) between H-7Љ and H-8Љ, and the NOE correlations between H-7Љ/H-9Љ and H-8Љ/H-2Љ, H-6Љ clearly indicated a threo configuration of the chiral centers of the dioxane ring. [7][8][9] The absolute configurations at C-7Љ and C-8Љ were determined based on the rotation direction comparison with synthetic analogs, (Ϫ)-aiphanol and (ϩ)-aiphanol.…”

Section: Notesmentioning

confidence: 99%

Two New Compounds from Dendrobium candidum

Wang

Guo

et al. 2008

Chem. Pharm. Bull.

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NotesThe traditional Chinese medicine "Shi Hu", prepared from the dried or fresh stems of several Dendrobium species (Orchidaceae), is widely used as both traditional Chinese and folk remedies for antipyretic, eyes-benefiting, and tonic purposes.1) Dendrobium candidum WALL. ex LINDL. is one of the most popular and valuable Dendrobium species and has been recorded in the Chinese Pharmacopoeia (2005 Edition) as one of the original materials of "Shi Hu". However, no phytochemical study of D. candidum has been reported to date. So, a phytochemical investigation on D. candidum has been undertaken by our group. As a result, two new compounds (1, 2) were isolated, along with five known compounds (3-7). [2][3][4][5] The known compounds were identified by comparisons with previously reported physical and spectral data. ) and NMR analysis revealed the molecular formula C 17 H 20 O 5 . The structure of 1 was deduced from its 1D-and 2D-NMR data and comparison with those of 3,4-dihydroxy-5,4Ј-dimethoxybibenzyl (4).3) The absolute configuration of 1 was established as (R) on the basis of the negative Cotton effect at 230 nm (De Ϫ1.29) in its circular dichroism (CD) spectrum, which was opposite to those of analogs (notice that the stereodescriptor is (S) in those cases). C-NMR data, a bibenzyl skeleton with two hydroxyl and three methoxyl groups were deduced to the structure of 1. But the significant difference between 1 and the 3,4-dihydroxy-5,4Ј-dimethoxybibenzyl (4) reported 3) was observed at benzylic protons. The four equivalent benzylic proton signals in upfield region of the known bibenzyl were replaced by the signals for one oxygenated methine and two methylene protons in 1. In combination with the 13 C-1 H long-range correlation between d H 3.19 (a-OMe-H 3 ) and d C 85.2 (C-a) in the HMBC spectrum, the fragment of one benzylic proton substituted by a methoxyl group was determined. Other key HMBC correlations are shown in Fig. 2. Thus, the structure of 1 was established as (R)-3,4-dihydroxy-5,4Ј,a-trimethoxybibenzyl. Two new compounds were isolated from the stems of Dendrobium candidum: (R)-3,4-dihydroxy-5,4,a atrimethoxybibenzyl (1), named dendrocandin A; and 4-[2-[(2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-hydroxymethyl-8-methoxy-2,3-dihydrobenzo[1,4]dioxin-6-yl]ethyl]-1-methoxyl benzene (2), dendrocandin B. Five previously known bibenzyls were also identified: 4,4-dihydroxy-3,5-dimethoxybibenzyl (3), 3,4-dihydroxy-5,4-dimethoxybibenzyl (4), 3-O-methylgigantol (5), dendrophenol (6), and gigantol (7).

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“…The ring linked at C-2/C-8Ј via an oxygen atom and at C-3/C-7Ј via another oxygen atom, which was determined definitely by HMBC correlations H-7Ј/C-3 and H-8Ј/C-2. The relative configurations of the chiral centers of dioxane ring were deduced as trans from the coupling constant (J 7Ј,8Ј ϭ 8.0 Hz) between H-7Ј and H-8Ј, [5][6][7] and the correlations of H-7Ј/H-10Ј and H-8Ј/H-4Ј, H-6Ј in rotating frame Overhauser enhancement spectroscopy (ROESY) spectrum.…”

mentioning

confidence: 99%

Four New Bibenzyl Derivatives from Dendrobium candidum

Wang

et al. 2009

Chem. Pharm. Bull.

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Convergent synthesis and preliminary biological evaluations of the stilbenolignan (±)-aiphanol and various congeners

Abstract: Treatment of an equimolar mixture of stilbene 7 and cinnamyl alcohol 8 with silver carbonate in acetone-benzene afforded a ca. 2:1:2:1 mixture of the stilbenolignan (+/-)-aiphanol (1) and congeners 2-4 each of which show significant anti-angiogenic and COX-2 inhibitory properties.

Cited by 23 publications

References 16 publications

Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites

Astonishing diversity of natural surfactants: 5. Biologically active glycosides of aromatic metabolites

Two New Compounds from Dendrobium candidum

Four New Bibenzyl Derivatives from Dendrobium candidum

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