Butanolides and clerodane diterpenes from the twigs of Casearia grewiifolia and their effects on adiponectin secretion

Piseth Nhoek; Seokyoung Hwang; Jungmoo Huh; Pisey Pel; Chan Woong Park; Piseth Khiev; Hyun Woo Kim; Minsoo Noh; Young Won Chin

doi:10.1016/j.bioorg.2024.107890

Butanolides and clerodane diterpenes from the twigs of Casearia grewiifolia and their effects on adiponectin secretion

Piseth Nhoek, Seokyoung Hwang, Jungmoo Huh, Pisey Pel, Chan Woong Park, Piseth Khiev, Hyun Woo Kim, Minsoo Noh, Young Won Chin

Research output: Contribution to journal › Article › peer-review

Abstract

Three butanolides derivatives, grewiifolides A–C, and nine clerodane diterpenes, grewiifolins M-U, as well as a known sterol were isolated from the twigs of Casearia grewiifolia. The chemical structures and configurations of all isolates were established by various spectroscopic means and chemical derivatization. In a cell-based phenotypic assay using the adipogenesis model of human bone marrow mesenchymal stem cells (hBM-MSCs), grewiifolide B significantly promoted adiponectin-secretion with EC₅₀ value of 24.8 µM. In target identification studies, butanolide derivatives were selectively bound to PPARγ with K_i values of 4.65, 0.55, and 17.8 µM, respectively. Further functional analysis and molecular modeling revealed that grewiifolide B promotes adiponectin-secretion through PPARγ full agonism.

Original language	English
Article number	107890
Journal	Bioorganic Chemistry
Volume	153
DOIs	https://doi.org/10.1016/j.bioorg.2024.107890
State	Published - Dec 2024

Keywords

Adiponectin-secretion
Butanolide
Casearia grewiifolia
Clerodane-type diterpene
PPARγ
hBM-MSC

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10.1016/j.bioorg.2024.107890

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@article{559e4cbd5b854377813334200a23191f,

title = "Butanolides and clerodane diterpenes from the twigs of Casearia grewiifolia and their effects on adiponectin secretion",

abstract = "Three butanolides derivatives, grewiifolides A–C, and nine clerodane diterpenes, grewiifolins M-U, as well as a known sterol were isolated from the twigs of Casearia grewiifolia. The chemical structures and configurations of all isolates were established by various spectroscopic means and chemical derivatization. In a cell-based phenotypic assay using the adipogenesis model of human bone marrow mesenchymal stem cells (hBM-MSCs), grewiifolide B significantly promoted adiponectin-secretion with EC50 value of 24.8 µM. In target identification studies, butanolide derivatives were selectively bound to PPARγ with Ki values of 4.65, 0.55, and 17.8 µM, respectively. Further functional analysis and molecular modeling revealed that grewiifolide B promotes adiponectin-secretion through PPARγ full agonism.",

keywords = "Adiponectin-secretion, Butanolide, Casearia grewiifolia, Clerodane-type diterpene, PPARγ, hBM-MSC",

author = "Piseth Nhoek and Seokyoung Hwang and Jungmoo Huh and Pisey Pel and Park, {Chan Woong} and Piseth Khiev and Kim, {Hyun Woo} and Minsoo Noh and Chin, {Young Won}",

note = "Publisher Copyright: {\textcopyright} 2024 Elsevier Inc.",

year = "2024",

month = dec,

doi = "10.1016/j.bioorg.2024.107890",

language = "English",

volume = "153",

journal = "Bioorganic Chemistry",

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T1 - Butanolides and clerodane diterpenes from the twigs of Casearia grewiifolia and their effects on adiponectin secretion

AU - Nhoek, Piseth

AU - Hwang, Seokyoung

AU - Huh, Jungmoo

AU - Pel, Pisey

AU - Park, Chan Woong

AU - Khiev, Piseth

AU - Kim, Hyun Woo

AU - Noh, Minsoo

AU - Chin, Young Won

PY - 2024/12

Y1 - 2024/12

N2 - Three butanolides derivatives, grewiifolides A–C, and nine clerodane diterpenes, grewiifolins M-U, as well as a known sterol were isolated from the twigs of Casearia grewiifolia. The chemical structures and configurations of all isolates were established by various spectroscopic means and chemical derivatization. In a cell-based phenotypic assay using the adipogenesis model of human bone marrow mesenchymal stem cells (hBM-MSCs), grewiifolide B significantly promoted adiponectin-secretion with EC50 value of 24.8 µM. In target identification studies, butanolide derivatives were selectively bound to PPARγ with Ki values of 4.65, 0.55, and 17.8 µM, respectively. Further functional analysis and molecular modeling revealed that grewiifolide B promotes adiponectin-secretion through PPARγ full agonism.

AB - Three butanolides derivatives, grewiifolides A–C, and nine clerodane diterpenes, grewiifolins M-U, as well as a known sterol were isolated from the twigs of Casearia grewiifolia. The chemical structures and configurations of all isolates were established by various spectroscopic means and chemical derivatization. In a cell-based phenotypic assay using the adipogenesis model of human bone marrow mesenchymal stem cells (hBM-MSCs), grewiifolide B significantly promoted adiponectin-secretion with EC50 value of 24.8 µM. In target identification studies, butanolide derivatives were selectively bound to PPARγ with Ki values of 4.65, 0.55, and 17.8 µM, respectively. Further functional analysis and molecular modeling revealed that grewiifolide B promotes adiponectin-secretion through PPARγ full agonism.

KW - Adiponectin-secretion

KW - Butanolide

KW - Casearia grewiifolia

KW - Clerodane-type diterpene

KW - PPARγ

KW - hBM-MSC

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DO - 10.1016/j.bioorg.2024.107890

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SN - 0045-2068

VL - 153

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

M1 - 107890

ER -

Butanolides and clerodane diterpenes from the twigs of Casearia grewiifolia and their effects on adiponectin secretion

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Keywords

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