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Pentacyclic and hexacyclic cucurbitacins from Elaeocarpus petiolatus

Cho, Eun Seon; Krishnan, Premanand; Loh, Hwei San; Daly, Janet M.; Leong, Chee Onn; Mai, Chun Wai; Low, Yun Yee; Yong, Kien Thai; Lim, Kuan Hon

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Authors

Eun Seon Cho

Premanand Krishnan

Hwei San Loh

Chee Onn Leong

Chun Wai Mai

Yun Yee Low

Kien Thai Yong

Kuan Hon Lim



Abstract

Four undescribed cucurbitacins, designated as petiolaticins A–D, and four known cucurbitacins were isolated from the bark and leaves of Elaeocarpus petiolatus (Jack) Wall. Their chemical structures were elucidated based on detailed analyses of the NMR and MS data. The absolute configuration of petiolaticin A was also determined by X-ray diffraction analysis. Petiolaticin A represents a cucurbitacin derivative incorporating a 3,4-epoxyfuranyl-bearing side chain, while petiolaticin B possesses a furopyranyl unit fused to the tetracyclic cucurbitane core structure. Petiolaticins A, B, and D were evaluated in vitro against a panel of human breast, pancreatic, and colorectal cancer cell lines. Petiolaticin A exhibited the greatest cytotoxicity against the MDA-MB-468, MDA-MB-231, MCF-7, and SW48 cell lines (IC50 7.4, 9.2, 9.3, and 4.6 μM, respectively). Additionally, petiolaticin D, 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one, and 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one 3-O-β-D-glucopyranoside were tested for their ability to inhibit cell entry of a pseudotyped virus bearing the hemagglutinin envelope protein of a highly pathogenic avian influenza virus. Petiolaticin D showed the highest inhibition (44.3%), followed by 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one (21.0%), and 16α,23α-epoxy-3β,20β-dihydroxy-10αH,23βH-cucurbit-5,24-dien-11-one 3-O-β-D-glucopyranoside showed limited inhibition (9.0%). These preliminary biological assays have demonstrated that petiolaticins A and D possess anticancer and antiviral properties, respectively, which warrant for further investigations.

Citation

Cho, E. S., Krishnan, P., Loh, H. S., Daly, J. M., Leong, C. O., Mai, C. W., Low, Y. Y., Yong, K. T., & Lim, K. H. (2022). Pentacyclic and hexacyclic cucurbitacins from Elaeocarpus petiolatus. Phytochemistry, 193, Article 112988. https://doi.org/10.1016/j.phytochem.2021.112988

Journal Article Type Article
Acceptance Date Oct 18, 2021
Online Publication Date Oct 27, 2021
Publication Date Jan 1, 2022
Deposit Date Oct 20, 2021
Publicly Available Date Oct 28, 2023
Journal Phytochemistry
Print ISSN 0031-9422
Publisher Elsevier
Peer Reviewed Peer Reviewed
Volume 193
Article Number 112988
DOI https://doi.org/10.1016/j.phytochem.2021.112988
Public URL https://nottingham-repository.worktribe.com/output/6504775
Publisher URL https://www.sciencedirect.com/science/article/abs/pii/S003194222100337X?via%3Dihub

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