52250-35-8Relevant articles and documents
A PTEROCARPAN AND TWO ISOFLAVANS FROM ALFALFA
Spencer, Gayland F.,Jones, Barry E.,Plattner, Ronald D.,Barnekow, David E.,Brinen, Linda S.,Clardy, Jon
, p. 4147 - 4150 (1991)
(-)-6aR,11aR-Dihydro-3-hydroxy-9,10-dimethoxy-6H-benzofuro-benzopyran (10-methoxymedicarpin), (+)-(2,3,4-trimethoxyphenyl)-2,3-dihydro-7-hydroxy-4H-1-benzopyran (7-hydroxy-2',3',4'-trimethoxyisoflavan) and (+)-(2,3,4-trimethoxy-5-hydroxyphenyl)-
Nitric oxide inhibitory flavonoids from traditional Chinese medicine formula Baoyuan Decoction
Ma, Xiaoli,Yu, Qian,Guo, Xiaoyu,Zeng, Kewu,Zhao, Mingbo,Tu, Pengfei,Jiang, Yong
, p. 252 - 259 (2015/06/08)
Abstract Three new flavonoid glycosides, (3R)-(+)-isomucronulatol-2′-O-β-D-glucopyranoside (1), (3R)-(-)-isomucronulatol-7-O-β-D-apiofuranosyl(1 → 2)-β-D-glucopyranoside (2), and (2S)-(-)-7,8-dihydroxylflavanone-4′-O-β-D-apiofuranosyl(1 → 2)-β-D-glucopyranoside (3), along with eight flavanones (4, 8, 10, 12, 15, 16, 21, and 24), four isoflavones (5, 11, 13, and 23), four chalcones (6, 14, 17, and 18), two isoflavans (19-20), one flavone (7), one flavonol (9), and one dihydrochalcone (22) were isolated from Baoyuan Decoction (BYD), a traditional Chinese medicine formula. The structures of the new compounds were established by detailed analysis of NMR and HRESIMS spectroscopic data, and their absolute configurations were determined by electronic circular dichroism (ECD) data. The inhibitory effects of the isolates were evaluated on nitric oxide production in lipopolysaccharide activated RAW 264.7 macrophage cells. Compounds 6, 9, and 10 showed the significant inhibitory activities, with IC50 values of 1.4, 13.8, and 9.3 μM, respectively, comparable to or even better than the positive control, quercetin (IC50, 16.5 μM). The assignment of these isolated flavonoids was achieved using UPLC-Q-trap-MS, and the results suggested that they were originated from Astragalus membranaceus and Glycyrrhiza uralensis.
Inhibitors of prostaglandin biosynthesis from Dalbergia odorifera
Goda,Kiuchi,Shibuya,Sankawa
, p. 2452 - 2457 (2007/10/02)
The root heartwood of Dalbergia odorifera T. CHEN (Leguminosae) is a Chinese medicinal drug (Japanese name koshinko) used for a stagnant blood syndrome (stagnation of disordered blood; Japanese, oketsu). In addition to 10 known compounds, five new phenolic compounds, isomucronustyrene and hydroxyobtustyrene (cinnamylphenols), (+)-isoduartin (isoflavan), odoriflavene (isoflav-3-ene) and (-)-odoricarpan (pterocarpan) were isolated and their structures were elucidated on the basis of chemical and spectroseopic methods. Of the fifteen compounds isolated, cinnamylphenols, isoflavans, isoflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.
Biosynthesis of the isoflavan isomucronulatol: Origin of the 2′,3′,4′-oxygenation pattern
Al-Ani, Hakim A.M.,Dewick, Paul M.
, p. 55 - 61 (2007/10/02)
Feeding experiments with 14C-labelled isoflavones in seedlings and pods of bladder senna (Colutea arborescens) have demonstrated that 7-hydroxy-4′-methoxyisoflavone (formononetin), 7,3′-dihydroxy-4′-methoxyisoflavone (calycosin), 7,2′,3′-trihydroxy-4′-methoxyisoflavone (koparin) and 7,2′-dihydroxy-3′,4′-dimethoxyisoflavone are excellent precursors of (3R)-isomucronulatol (7,2′-dihydroxy-3′,4′-dimethoxyisoflavan). 7,2′-Dihydroxy- 4′-methoxyisoflavone (2′-hydroxyformononetin) and 7-hydroxy-3′,4′-dimethoxyisoflavone (cladrin) were, however, poor substrates. Thus, the biosynthetic sequence to isomucronulatol from formononetin involves 3′-hydroxylation, 2′-hydroxylation and then 3′-O-methylation, followed presumably by stereospecific reduction of 7,2′-dihydroxy-3′,4′-dimethoxyisoflavone. Treatment of 2′,3′,4′-trimethoxyisoflavones with aluminium chloride in acetonitrile gives modest yields of 2′,3′-dihydroxy derivatives rather than 2′-monohydroxyisoflavones, and thus provides a convenient access to 2′,3′-dihydroxyisoflavones and related pterocarpans.
