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Issue 20, 2016
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ent-Abietane diterpenoids with anti-neuroinflammatory activity from the rare Chloranthaceae plant Chloranthus oldhamii

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Abstract

Twelve new ent-abietane diterpenoids, chlorabietins A–L (1–12), were isolated from the roots of Chloranthus oldhamii. Their structures and absolute configurations were determined by extensive spectroscopic analyses, X-ray diffraction, and experimental/calculated electronic circular dichroism (ECD) spectroscopy. Among the new isolates, chlorabietins D (4) and E (5) are the first two naturally occurring 8-spiro-fused 9,10-seco-ent-abietanes containing an unexpected cis-fused A/B ring system. Chlorabietin F (6) is a rare chinane-type diterpenoid featuring a hitherto unknown C-ring cleavage between C-13 and C-14, which might be derived from a common precursor of the above spiro-diterpenoid epimers 4 and 5, and their biosynthetic relationships are briefly discussed. Meanwhile, chlorabietin I (9) is the first representative of the abietane-type diterpenoids possessing a tetrahydrofurano function bridging C-6 and C-19. Chlorabietins B (2), C (3), F (6), and G (7) showed anti-neuroinflammatory effects by inhibiting the nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine BV-2 microglial cells, with IC50 values ranging from 16.4 to 33.8 μM.

Graphical abstract: ent-Abietane diterpenoids with anti-neuroinflammatory activity from the rare Chloranthaceae plant Chloranthus oldhamii

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Publication details

The article was received on 07 Apr 2016, accepted on 19 Apr 2016 and first published on 19 Apr 2016


Article type: Paper
DOI: 10.1039/C6OB00731G
Org. Biomol. Chem., 2016,14, 4678-4689

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    ent-Abietane diterpenoids with anti-neuroinflammatory activity from the rare Chloranthaceae plant Chloranthus oldhamii

    J. Xiong, Z. Hong, P. Xu, Y. Zou, S. Yu, G. Yang and J. Hu, Org. Biomol. Chem., 2016, 14, 4678
    DOI: 10.1039/C6OB00731G

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