( Rel)-1β,2α-di-(2,4-dihydroxy-6-methoxybenzoyl)-3β, 4α-di-(4-methoxyphenyl)-cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii

Abstract

The aerial parts of Goniothalamus gardneri (Annonaceae) has yielded the known flavonoids 2′-hydroxy-4,4′,6′-trimethoxychalcone (flavokawain A), 2′,4′-dihydroxy-4,6′-dimethoxydihydrochalcone, 4,2′,4′-trihydroxy-6′-methoxydihydrochalcone, 5,7,4′-trimethoxyflavanone (naringenin trimethyl ether) and 7-hydroxy-5,4′-dimethoxyflavanone (tsugafolin) together with three novel compounds, the dimer characterised as ( rel)-1β,2α-di-(2,4-dihydroxy-6-methoxybenzoyl)-3β,4α-di-(4-methoxyphenyl)-cyclobutane, 2′,4′-dihydroxy-4,6′-dimethoxychalcone and 2′-hydroxy-4,4′,6′-trimethoxydihydrochalcone. The last two have previously been synthesised but appear to be new natural products. A similar study of the aerial parts of G. thwaitesii led only to the isolation of the known flavonoids myricetin 4′- O-methyl ether-3- O-α- l-rhamnopyranoside (mearnsitrin) and myricetin-3- O-methyl ether (annulatin), together with the triterpenes friedelinol, friedelin and betulinic acid. All compounds were identified by spectroscopic analysis and, for known compounds, by comparison with published data.