Issue 20, 2021

Cunlanceloic acids A–D: unprecedented labdane diterpenoid dimers with AChE inhibitory and cytotoxic activities from Cunninghamia lanceolata

Abstract

Cunlanceloic acid A (1), a symmetric terpenoid peroxide bearing an unprecedented dimeric labdane backbone linked through C-16/C-16′ bonds, and cunlanceloic acids B–D (2–4), three asymmetric diterpenoid dimers with a new carbon skeleton linked through C12/C-13′ and C-15/C-16′ bonds between two labdane units, were isolated from the cones of Cunninghamia lanceolata. Their structures including absolute configurations were determined by extensive NMR spectroscopy, X-ray diffraction analysis, and chemical transformations. Compound 1 exhibited potent AChE inhibitory activity with an IC50 value of 6.14 ± 0.66 μM and compounds 2 and 3 showed remarkable cytotoxic activities against A-549 and SMMC-7721 cell lines with IC50 values of 5.90–9.21 μM.

Graphical abstract: Cunlanceloic acids A–D: unprecedented labdane diterpenoid dimers with AChE inhibitory and cytotoxic activities from Cunninghamia lanceolata

Supplementary files

Article information

Article type
Research Article
Submitted
06 Upu 2021
Accepted
06 Pha 2021
First published
09 Pha 2021

Org. Chem. Front., 2021,8, 5777-5784

Cunlanceloic acids A–D: unprecedented labdane diterpenoid dimers with AChE inhibitory and cytotoxic activities from Cunninghamia lanceolata

X. Wu, L. Ding, B. Chen, X. Li, L. Peng and Q. Zhao, Org. Chem. Front., 2021, 8, 5777 DOI: 10.1039/D1QO00999K

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