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Novel Diarylheptanoids of Alpinia blepharocalyx

[ Vol. 3 , Issue. 2 ]


Shigetoshi Kadota, Yasuhiro Tezuka, Jeevan Kumar Prasain, Mohammad Shawkat Ali and A. H. Banskota   Pages 203 - 225 ( 23 )


The seeds of Alpinia blepharocalyx K. Schum. (Zingiberaceae) is used in Chinese traditional medicine for the treatment of stomach disorders. From the ether fraction of a 95% ethanolic extract, which showed hepatoprotective and antiproliferative activities, we isolated 16 novel diarylheptanoids bearing a chalcone or a flavanone moiety [calyxins A-H; epicalyxins B-D, G, and H, 6-hydroxycalyxin F; and blepharocalyxins A and B] together with seven known compounds, while the residual fraction of the ethanolic extract gave 32 novel diarylheptanoids namely, calyxins A, E-G, and I-M, epicalyxins B, F, I-K, and M, deoxycalyxin A, blepharocalyxins C-E, neocalyxins A and B, (3S,5S)- and (3S,5R)-3-hydroxy-1-(4- hydroxyphenyl)-5-methoxy-7-phenyl-6E-heptene, (3S,5S)- and (3S,5R)-3-hydroxy-1-(4-hydroxyphenyl)-5- ethoxy-7-phenyl-6E-heptene, (3S)-3-methoxy-1,7-bis(4-hydroxyphenyl)-6E-hepten-5-one, 1,7-bis(4- hydroxyphenyl)-hepta-4E,6E-dien-3-one, (3S,7R)-5,6-dehydro-1,7-bis(4-hydroxy-phenyl)-4“-de-O-methylcentrolobine, (3S,5S,6S,7R)-5,6-dihydroxy-1,7-bis(4-hydroxyphenyl)-4“-de-O-me-thylcentrolobine, (3S,5R,6S,7R)- and (3S,5S,6R,7R)-5,6-dihydroxy-1,7-bis(4-hydroxyphenyl)-4“-de-O-methyl-centrolobine, 1,2- dihydro-bis(de-O-methyl)curcumin, and (3S,7S)-5,6-dehydro-4-de-O-methylcentrolobine, and one known diarylheptanoid [(3S,5S)-3,5-dihydroxy-1,7-bis(4-hydroxyphenyl)heptane] together with 12 other known phenolic compounds. Moreover, in vitro NO inhibitory and antiproliferative activities of the isolated compounds were also tested and the active constituents identified.


Novel Diarylheptanoids, Alpinia blepharocalyx, methylcentrolobine, 4-hydroxyphenyl, diarylheptanoid, epicalyxins, ntiproliferative


Department of Natural Products Chemistry, Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, 2630-Sugitani, Toyama 930-0194, Japan

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