Callnudoids A-H: Highly modified labdane diterpenoids with anti-inflammation from the leaves of Callicarpa nudiflora.

Abstract

Eight undescribed 3,4-seco-norlabdane diterpenoids, callnudoids A-H, as well as two known analogues were isolated from the leaves of Callicarpa nudiflora. The structures were elucidated using spectroscopic methods and were compared with published NMR spectroscopic data. The absolute configurations of callnudoids D and E were defined based on ECD data or single-crystal X-ray diffraction. Callnudoids A-C are the highly modified labdane diterpenoids featuring rearranged 3,4-seco-ring and the formation of an undescribed cyclohexene moiety via C2-C18 cyclization. They only contain 15 carbon atoms on the carbon skeleton. Callnudoid D represents the unusual 3,4-seco-15,16-norlabdane diterpenoid with C13-C17 cyclization, and a putative biosynthesis pathway for callnudoids A, B, D, and E was proposed. All compounds were evaluated for their anti-inflammatory activities by inhibiting the lipopolysaccharide (LPS)-induced nitric oxide (NO) released in RAW264.7 cells; callnudoids A-E and H, and methylcallicarpate obviously inhibited pro-inflammatory cytokines TNF-α and IL-1β in a dose-dependent manner.

• Authors: Zhang-Xin Yu, Can-Hong Wang, Xu-Hua Nong, De-Li Chen, Meng-Ling Xu, Xiao-Bao Li, Yang-Yang Liu, Guang-Ying Chen
• Journal: Phytochemistry (Phytochemistry) Vol. 201 Pg. 113253 (Sep 2022) ISSN: 1873-3700 [Electronic] England
• PMID: 35644486 (Publication Type: Journal Article)
• Copyright: Copyright © 2022. Published by Elsevier Ltd.

Chemical References

• Anti-Inflammatory Agents
• Diterpenes
• Carbon

Topics

• Anti-Inflammatory Agents (chemistry, pharmacology)
• Callicarpa (chemistry)
• Carbon
• Diterpenes (chemistry, pharmacology)
• Molecular Structure