Spiro-meroterpenoids, Syzygioblanes D–H, Isolated from Indonesian Medicinal Plant <i>Syzygium oblanceolatum</i>
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.
Authors
- Katsunori Miyake (ORCID: https://orcid.org/0000-0001-6199-8781)
- Tomoya Nishida
- Ahmad Najib (ORCID: https://orcid.org/0000-0001-5055-7964)
- Kyoko Nakagawa‐Goto (ORCID: https://orcid.org/0000-0002-1642-6538)
- Gemini Alam (ORCID: https://orcid.org/0000-0001-7721-9658)
- Atsushi Mizokami (ORCID: https://orcid.org/0000-0002-5643-2182)
- Shuichi Fukuyoshi (ORCID: https://orcid.org/0000-0002-9015-0920)
- Abdul Rahim (ORCID: https://orcid.org/0000-0003-1409-7619)
- K. KAWASHIMA
- Saidanxia Amuti
- Nobuyuki Tanaka (ORCID: https://orcid.org/0000-0002-3003-7782)
- Yohei Saito (ORCID: https://orcid.org/0000-0003-2313-8339)
- Chihiro Ito
- N. Koga
Institutions
- Kanazawa University (JP)
- University of North Carolina at Chapel Hill (US)
- Tokyo University of Pharmacy and Life Sciences (JP)
- Life Science Institute (JP)
- National Museum of Nature and Science (JP)
- Pharmaceutical Biotechnology (Czechia) (CZ)
- Eastman Chemical Company (Germany) (DE)
- Hasanuddin University (ID)
Publication Details
- Journal
- Journal of Natural Products
- Published
- 2024-12-13
- DOI
- https://doi.org/10.1021/acs.jnatprod.4c01154
- Citations
- 3
- Primary Topic
- Ethnobotanical and Medicinal Plants Studies
- Type
- article
- Field-Weighted Citation Impact
- 1.80
Funders
- Mitani Foundation for Research and Development