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A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
Spiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant Syzygium oblanceolatum
Nona Koga1, Kaede Kawashima1, Chihiro Ito1
1School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan.
Abstract:
Syzygioblanes A-C (1-3), isolated from the Indonesian traditional herbal medicine Syzygium oblanceolatum (S. oblanceolatum), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of S. oblanceolatum resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (4-8), 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 (6) and G (7) 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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