Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities

Phytochemical investigation of the leaf extract of <i>Uvaria grandiflora</i> Roxb. ex Hornem led to the isolation and identification of two new highly oxygenated cyclohexenes, uvariagrandols A (<b>1</b>) and B (<b>2</b>), together with seven known compounds (<b>3</b>-<b>9</b>). Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. The (1<i>S</i>,2<i>S</i>,3<i>R</i>,6<i>S</i>) absolute configuration of uvariagrandols A and B was established by the comparison of the experimental and calculated electronic circular dichroism (ECD). (+)-Grandifloracin (<b>9</b>) displayed cytotoxicity against SW480 and K562 cell lines with IC<sub>50</sub> values of 154.9 and 60.9 μM, respectively. 6-Methoxyzeylenol (<b>5</b>) had <i>α</i>-glucosidase inhibitory activity with the IC<sub>50</sub> value of 34.1 μM.

Authors

Institutions

Publication Details

Journal
Heliyon
Published
2024-12-18
DOI
https://doi.org/10.1016/j.heliyon.2024.e41326
Primary Topic
Traditional and Medicinal Uses of Annonaceae
Type
article
Field-Weighted Citation Impact
0.00

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities

Passakorn Teerapongpisan, Virayu Suthiphasilp, Raymond J. Andersen, Phunrawie Promnart et al.
Heliyon
Traditional and Medicinal Uses of Annonaceae
article

Highly oxygenated cyclohexenes from the leaves of Uvaria grandiflora Roxb. ex Hornem and their cytotoxic and α-glucosidase inhibitory activities

Passakorn Teerapongpisan, Virayu Suthiphasilp, Raymond J. Andersen, Phunrawie Promnart, Surat Laphookhieo, Tharakorn Maneerat, Sarawut Tontapha, Pakit Kumboonma, Narawadee Rujanapun, Boonyanoot Chaiyosang, Thidarat Duangyod, Moses Egoh Betangah, Rawiwan Charoensup, Brian O. Patrick
article en

Abstract

Phytochemical investigation of the leaf extract of <i>Uvaria grandiflora</i> Roxb. ex Hornem led to the isolation and identification of two new highly oxygenated cyclohexenes, uvariagrandols A (<b>1</b>) and B (<b>2</b>), together with seven known compounds (<b>3</b>-<b>9</b>). Their structures were elucidated by spectroscopic methods as well as comparisons made from the literature. The (1<i>S</i>,2<i>S</i>,3<i>R</i>,6<i>S</i>) absolute configuration of uvariagrandols A and B was established by the comparison of the experimental and calculated electronic circular dichroism (ECD). (+)-Grandifloracin (<b>9</b>) displayed cytotoxicity against SW480 and K562 cell lines with IC<sub>50</sub> values of 154.9 and 60.9 μM, respectively. 6-Methoxyzeylenol (<b>5</b>) had <i>α</i>-glucosidase inhibitory activity with the IC<sub>50</sub> value of 34.1 μM.

HeliyonVol. 11(1)
Rajamangala University of Technology Isan (TH), University of British Columbia (CA), Khon Kaen University (TH), Thailand Graduate Institute of Science and Technology (TH), Mae Fah Luang University (TH), Walailak University (TH)
Mae Fah Luang University, National Research Council of Thailand, Thailand Science Research and Innovation
Zero hunger
Openalex Percentile: Top 76%
Traditional and Medicinal Uses of Annonaceae
DOIOpen Access PDFOpenAlex
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.