PACHYOVATAMINE, A BISBENZYLISOQUINOLINE ALKALOID, AND OTHER ALKALOIDS FROM PACHYGONE OVATA
Key Word Index - Pachygone ovata; Menispermaceae; leaves and stems; dibenzo-p-dioxin biphenyl bisbenzylisoquinoline alkaloids; pachiovatamine. - A new dibenzo-p-dioxin biphenyl bisbenzylisoquinoline alkaloid, pachyovatamine, has been isolated from an extract of the leaves and stems of Pachygone ovata from Sri Lanka.The alkaloid was characterized by a consideration of its physicochemical data and conversion to O-acetyltiliacorinine.Pachyigonamine, N-methylpachygonamine and tiliamosine were also isolated from the same extract.
Sultanbawa, M. Uvais S.,Sotheeswaran, Subramaniam,Balasubramaniam, Sinnathamby,El-Kawi, Moustafa Abd,Slatkin, David J.,Schiff, Paul L.
Three known alkaloids, tiliacorinine (1), tiliacorine (2) and nortiliacorinine A (3), together with a new alkaloid, tiliacorinine 2'-N-oxide (4), have been isolated from the roots of Tiliacora triandra Diels (Menispermaceae).
Wiriyachitra, Pichaet,Phuriyakorn, Boondate
p. 2001 - 2004
(2007/10/02)
THE STRUCTURE, ABSOLUTE CONFIGURATION AND BIOSYNTHESIS OF NORTILIACORININE A
The incorporation of (+/-)-norcoclaurine, (+/-)-coclaurine, (+/-)-N-methylcoclaurine and dehydro-N-methylcoclaurine into nortiliacorinine A in Tilicora racemosa colebr has been studied and specific utilisation of the (+/-)-coclaurine demonstrated.The evidence supports oxidative dimerization of two coclaurine units to give nortiliacorinine A.Experiments with (+/-)-N-methylcoclaurine and (+/-)-N-methylcoclaurine established that only one N-methylcoclaurine unit is specifically utilised to constitute that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into nortiliacorine A.Double labelling experiment with (+/-)-N-methylcoclaurine showed that O-Me function of the precursor is lost in the bioconversion into nortiliacorine A.Parallel feedings of (+)-(S)-, and (-)-(R)-N-methyl-coclaurines and (-)-(S)-, and (+)-(R)-coclaurines revealed that the stereo-specificity is maintained in the biosynthesis of nortiliacorinine A from 1-benzylisoquinoline precursors and established S,S'-configuration at the two asymmetric centres in nortiliacorinine A.
Bhakuni, Dewan S,Singh, Awadhesh,Jain, Sudha
p. 2651 - 2655
(2007/10/02)
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