Eun Seon Cho
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
Authors
Premanand Krishnan
Hwei San Loh
Professor JANET DALY janet.daly@nottingham.ac.uk
PROFESSOR OF VIRAL ZOONOSES
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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