Three new cassane-type diterpenoids from Caesalpinia sinensis

Yuan-Kai Chen; Miao-Yin Fan; Ya-Mei Zhang; Pu-Zhao Zhang; Ren-Geng Shu

doi:10.1080/10286020.2022.2026933

Three new cassane-type diterpenoids from Caesalpinia sinensis

J Asian Nat Prod Res. 2022 Dec;24(12):1134-1140. doi: 10.1080/10286020.2022.2026933. Epub 2022 Jan 17.

Authors

Yuan-Kai Chen^{1

2}, Miao-Yin Fan¹, Ya-Mei Zhang¹, Pu-Zhao Zhang¹, Ren-Geng Shu²

Affiliations

¹ Key Laboratory of Modern Preparation of TCM, Ministry of Education, Jiangxi University of Chinese Medicine, Nanchang 330004, China.
² College of Pharmacy, Jiangxi University of Chinese Medicine, Nanchang 330004, China.

PMID: 35037543
DOI: 10.1080/10286020.2022.2026933

Abstract

Three new cassane-type diterpenoids, namely, (4S)-6β,12α,19-trihydroxy-cass-13(15)-en-16,12-olide (1), cass-13(15)-en-16,12-olide (2), and 12α-hydroxy-cass-13(15)-en-16,12-olide (3), were isolated from the seeds of Caesalpinia sinensis. The structures of 1-3 were established by extensive spectroscopic analysis, and their absolute configurations were assigned by electronic circular dichroism (ECD) calculations. The inhibitory activities against PTP1B of the isolated compounds were evaluated. The results showed that compound 2 possessed PTP1B inhibitory activity with an IC₅₀ value of 217.45 ± 36.4 μM.

Keywords: Caesalpinia sinensis; Fabaceae; PTP1B; cassane diterpenoids.

MeSH terms

Caesalpinia* / chemistry
Diterpenes* / chemistry
Diterpenes* / pharmacology
Molecular Structure
Seeds / chemistry

Substances

6-chloropenicillanic acid S-sulfoxide
Diterpenes