Issue 19, 2019

Officinalins A and B, a pair of C23 terpenoid epimers with a tetracyclic 6/7/5/5 system from Salvia officinalis

Abstract

A pair of novel C23 terpenoid epimers, officinalins A (1) and B (2), together with a biogenetically related known diterpenoid (3), was isolated from the leaves of Salvia officinalis. The epimers feature an unprecedented carbon skeleton with a tetracycline-[9.6.0.03,8.012,16]-heptadecane core and a peroxide bridge. Their structures were unequivocally established by extensive spectroscopic analyses, including electronic circular dichroism (ECD) calculations and ROESY correlation analogy with model compounds for the configuration assignment. Possible biosynthetic pathways of 1 and 2 were proposed. Compound 1 exhibited potent NO inhibitory activity with an IC50 value of 2.02 ± 0.87 μM.

Graphical abstract: Officinalins A and B, a pair of C23 terpenoid epimers with a tetracyclic 6/7/5/5 system from Salvia officinalis

Supplementary files

Article information

Article type
Research Article
Submitted
06 Jul 2019
Accepted
20 Aug 2019
First published
21 Aug 2019

Org. Chem. Front., 2019,6, 3369-3373

Officinalins A and B, a pair of C23 terpenoid epimers with a tetracyclic 6/7/5/5 system from Salvia officinalis

L. Li, X. Liu, D. Zhu, C. Chen, Y. Lin, W. Wang, L. Zhu, J. Luo and L. Kong, Org. Chem. Front., 2019, 6, 3369 DOI: 10.1039/C9QO00861F

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