Puerol B

Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.[Pubmed:26248805]

Bioorg Med Chem Lett. 2015 Sep 15;25(18):3825-30.

A phytochemical investigation of the roots of Ononis angustissima L. (Fabaceae) offered to the bio-guided isolation of new isoflavone 3-(4-(glucopyranosyloxy)-5-hydroxy-2-methoxyphenyl)-7-hydroxy-4H-chromen-4-one 1, together with nine known compounds, ononin 2, formononetin 3, (+)-puerol A-2'-O-beta-D-glucose 4, (-)-Puerol B-2'-O-beta-D-glucopyranose ((-)-sophoraside A) 5, (+)-puerol A 6, (-)-trifolirhizin 7, (-)-trifolirhizin-6'-O-malonate 8, (-)-maackiain 9 and (-)-medicarpin 10. Compounds 2-10 were isolated and identified for the first time in Ononis angustissima. We investigated antioxidant capacities of isolated molecules and results showed that compound 6 exhibited the highest antioxidant activity with IC50 values of 19.53 mug/mL, 28.29 mug/mL and 38.53 mug/mL by DPPH radical, ABTS radical cation and reducing power assay, respectively, and an interesting IC50 (20.45 mug/mL) of 1 against DPPH. In addition, the neuroprotective activity of six isolated molecules (4-7, 9, 10) were evaluated. Following the exposure of PC12 cells to Abeta25-35, compounds 9 and 10 triggered a significant increase of cell viability and in a dose dependent manner.

[Studies on biotransformation of chemical constituents of tongmai formula by human intestinal flora].[Pubmed:24490564]

Zhongguo Zhong Yao Za Zhi. 2013 Oct;38(20):3510-9.

To study the chemical constituents in Tongmai formula (TMF) after biotransformation by human intestinal flora (HIF), water extract of TMF was anaerobically incubated with HIF at 37 degrees C. Column chromatographic methods over silica gel, Sephadex LH-20 and semi-preparative high-performance liquid chromatography as well as recrystallization were used to isolate and purify the chemical constituents in TMF after biotransformation by HIF. The chemical structures of isolated compounds were identified on the basis of MS and NMR data. Twenty-six compounds were obtained and identified as phenylpropionic acid (1), 6"-O-acetylpuerarin (2), formononetin(3), daidzein(4), p-hydroxyphenylpropionic acid (5), 3-indolepropionic acid (6), genistein (7), isoformononetin (8), isoononin (9), a mixture of (-)-Puerol B-2"-O-glucopyranoside (10a) and (+) -Puerol B-2"-O-glucopyranoside (10b), 8-hydroxydaidzein (11), puerol A (12), 3'-methoxy-6"-O-acetylpuerarin (13), 6"-O-acetyldaidzin (14), 3'-methoxydaidzin (15), Puerol B (16), 3-methyluracil (17), genistin (18), daidzin (19), 3'-methoxypuerarin (20), mirificin (21), swertiamarin (22) , daidzein-7, 4'-O-glucoside (23), adenine (24), 3'-hydroxypuerarin (25), and puerarin (26). After biotransformation by HIF, the glycosides in TMF were transformed into aglycone and/or less glycosyl compounds along with some hydroxylation and demethylation reactions. Therefore, the glycosides in the TMF are the pro-drug.

[Chemical constituents from roots of Pueraria lobata].[Pubmed:21355238]

Zhongguo Zhong Yao Za Zhi. 2010 Dec;35(23):3156-60.

OBJECTIVE: To study the chemical constituents in the roots of Pueraria lobata. METHOD: Various chromatographic methods were employed to separate of chemical constituents and the spectroscopic methods were used to elucidate the structure. RESULT: Twenty-two compounds were isolated and characterized as beta-sitosterol palmitate (1), beta-sitosterol (2), lupeol (3), lupeone (4) , puerarol (5), diisobutyl phthalate (6), bis(2-ethylhexyl) phthalate (7), sophoracoumestan A (8), coumestrol (9), allantion (10), dadzein (11), formononetin (12), 3'-methoxy daidzein (13), ononin (14), 3'-hydroxy dadzein (15), genistin (16), dadzin (17), 8-methoxy ononin (18), sissotorin (19), (-)-Puerol B 2-O-glucopyranoside (20), (6S,9R)-roseoside (21) and sucrose (22), respectively. CONCLUSION: Compounds 1, 5-8, 15, 18, 21 and 22 were isolated from P. lobata for the first time, and componds 1, 5-7, 15, 18, 21 and 22 were isolated from the genus Pueraria for the first time.

Phenolic compounds from Pueraria lobata protect PC12 cells against Abeta-induced toxicity.[Pubmed:21052940]

Arch Pharm Res. 2010 Oct;33(10):1651-4.

Bioassay-guided fractionation of the EtOAc-soluble extract of Pueraria lobata based on the inhibition of Abeta-induced toxicity in PC12 cells resulted in the isolation of four known active compounds, genistein (8), biochanin A (9), sissotrin (10), and Puerol B (11). Of these, genistein (8) and biochanin A (9) exhibited potent neuroprotective effects with ED(50) values of 33.7 and 27.8 muM, respectively. In addition, a new coumestan, 2-(alpha,alpha-dimethylallyl)coumestrol (1) was isolated and characterized, but proved to be inactive, as were additional seven known compounds. The structure of new compound 1 was determined using spectroscopic techniques.

Constituents of the roots of Pueraria lobata inhibit formation of advanced glycation end products (AGEs).[Pubmed:17121174]

Arch Pharm Res. 2006 Oct;29(10):821-5.

Two isoflavone C-glucosides, puerarin (1) and PG-3 (2), a but-2-enolide, (+/-)-Puerol B (3), two isoflavone O-glucosides, daidzin (4) and genistin (5), and three pterocarpans, (-)-medicarpin (6), (-)-glycinol (7) and (-)-tuberosin (8), were isolated from a MeOH extract of the roots of Pueraria lobata, using an in vitro bioassay based on the inhibition of the formation of advanced glycation end products (AGEs) to monitor chromatographic fractionation. The structures of 1-8 were determined by spectroscopic data interpretation, particularly by 1D- and 2D-NMR studies, and by comparison of these data with values in the literature. All of the isolates (1-8) were evaluated for their inhibitory activity on AGEs formation in vitro. Of these, puerarin (1), PG-3 (2), and (+/-)-Puerol B (3) exhibited more potent inhibitory activity than the positive control aminoguanidine.