Diplomeroterpenoid G: An unusual meroterpenoid from Mimosa pudica Linn. (Mimosaceae)

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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Cyclic Sesquiterpene–Flavanone [4+2] Hybrids, Syzygioblanes A–C, Found in an Indonesian Traditional Medicine, “Jampu Salo” (Syzygium oblanceolatum)

Koga,

Saito,

Miyake

et al. 2024

Org. Lett.

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A plant used in an Indonesian traditional herbal medicine as a diabetes treatment and known locally as "Jampu Salo" was collected on Sulawesi Island, Indonesia. It was identified as Syzygium oblanceolatum (C. B. Rob.) Merr. (Myrtaceae) and found for the first time in Sulawesi; it was previously reported only in the eastern Philippines and Borneo. A phytochemical study of S. oblanceolatum led to the isolation of three unprecedented meroterpenoids, syzygioblanes A−C (1−3, respectively). These compounds might be biosynthesized through [4+2] cycloaddition of various germacrane-based cyclic sesquiterpenoids with the flavone desmethoxymatteucinol to form a spiro skeleton. The unique and complex structures were elucidated by microcrystal electron diffraction analysis in addition to general analytical techniques such as high-resolution mass spectrometry, various nuclear magnetic resonance methods, and infrared spectroscopy. Synchrotron X-ray diffraction and calculations of electronic circular dichroism spectra helped to determine the absolute configurations. The newly isolated compounds exhibited collateral sensitivity to more strongly inhibit the growth of a multidrug resistant tumor cell line compared to a chemosensitive tumor cell line.

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Diplomeroterpenoid G: An unusual meroterpenoid from Mimosa pudica Linn. (Mimosaceae)

Cited by 3 publications

References 28 publications

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

Cyclic Sesquiterpene–Flavanone [4+2] Hybrids, Syzygioblanes A–C, Found in an Indonesian Traditional Medicine, “Jampu Salo” (Syzygium oblanceolatum)

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