Spiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant Syzygium oblanceolatum

Abstract

Syzygioblanes A-C (<b>1</b>-<b>3</b>), isolated from the Indonesian traditional herbal medicine <i>Syzygium oblanceolatum</i> (<i>S. oblanceolatum</i>), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of <i>S. oblanceolatum</i> resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (<b>4</b>-<b>8</b>), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule. The isolated syzygioblanes F (<b>6</b>) and G (<b>7</b>) demonstrated collateral sensitivity by inhibiting the growth of multidrug-resistant tumor cell lines more than the related chemosensitive tumor cell lines.

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