Herpetosin A, a nor-cucurbitane triterpenoid with a 5/6/6/5 ring system from Herpetospermum pedunculosum

Qianyu Chen; Yingxiong Ma; Zhaoyue Dong; Bing Xu; Guowei Wang; Xiaozhong Lan; Zhihua Liao; Min Chen

doi:10.1080/14786419.2024.2424399

Herpetosin A, a nor-cucurbitane triterpenoid with a 5/6/6/5 ring system from Herpetospermum pedunculosum

Nat Prod Res. 2024 Nov 5:1-7. doi: 10.1080/14786419.2024.2424399. Online ahead of print.

Authors

Qianyu Chen^{1

2}, Yingxiong Ma¹, Zhaoyue Dong^{1

2}, Bing Xu¹, Guowei Wang¹, Xiaozhong Lan³, Zhihua Liao^{4

5}, Min Chen^{1

2}

Affiliations

¹ Chongqing Key Laboratory of New Drug Screening from Traditional Chinese Medicine, Integrative Science Center of Germplasm Creation in Western China (Chongqing) Science City & Southwest University, SWU-TAAHC Medicinal Plant Joint R&D Centre, College of Pharmaceutical Sciences, Southwest University, Chongqing, P.R. China.
² Key Laboratory of Luminescence Analysis and Molecular Sensing, Ministry of Education, College of Pharmaceutical Sciences, Southwest University, Chongqing, P.R. China.
³ TAAHC-SWU Medicinal Plant R&D Center, Xizang Agriculture and Animal Husbandry College, Nyingchi, P.R. China.
⁴ The Provincial and Ministerial Cofounded Collaborative Innovation Center for R & D in Tibet Characteristic Agricultural and Animal Husbandry Resources, TAAHC-SWU Medicinal Plant Joint R&D Centre, School of Life Sciences, Southwest University, Chongqing, China.
⁵ Integrative Science Center of Germplasm Creation in Western China (CHONGQING) Science City & Southwest University, Chongqing, China.

PMID: 39497678
DOI: 10.1080/14786419.2024.2424399

Abstract

Two previously undescribed triterpenoids, herpetosin A (1) and herpetosin B (2), together with two known compounds, cucurbitacin B (3) and dihydrocucurbitacin E (4), were isolated from the seeds of Herpetospermum pedunculosum. Their structures were elucidated by analysis of the NMR, HR-ESI-MS, X-ray data and quantum chemical calculation. Compound 1 featured an unprecedented nor-cucurbitane triterpenoid skeleton with a 5/6/6/5 ring system. Among all the isolates, compound 4 exhibited anti-proliferative effect with IC₅₀ values of 4.5 ± 0.1 μM against A549 cells, 8.2 ± 0.5 μM against MDA-MB-231 cells, and 2.4 ± 0.3 μM against HepG2 cells, respectively.

Keywords: Herpetospermum pedunculosum; cytotoxicity; herpetosins A and B; nor-cucurbitane triterpenoid.