Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells

Kyo Bin Kang; Jin Bum Jun; Jung Wha Kim; Hyun Woo Kim; Sang Hyun Sung

doi:10.1016/j.phytochem.2017.06.014

Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells

Kyo Bin Kang, Jin Bum Jun, Jung Wha Kim, Hyun Woo Kim, Sang Hyun Sung

Department of Pharmacy

Seoul National University

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

19 Scopus citations

Abstract

Three ceanothane-type and three lupane-type triterpenoids, as well as three known compounds, were isolated from the roots of Hovenia dulcis (Rhamnaceae), based on LC–MS dereplication. The previously undescribed compounds were determined to be 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid, 27-O-protocatechuoyl-3-dehydroxycolubrinic acid, 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid, 27-O-protocatechuoylbetulinic acid, 27-O-p-hydroxybenzoylbetulinic acid, and 27-O-syringoylbetulinic acid by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. The isolates were examined for their antiproliferative activity in HSC-T6 hepatic stellate cells; compounds 1, 2, 3, and 6 showed IC₅₀ values in the range of 15–50 μM.

Original language	English
Pages (from-to)	60-67
Number of pages	8
Journal	Phytochemistry
Volume	142
DOIs	https://doi.org/10.1016/j.phytochem.2017.06.014
State	Published - Oct 2017

Keywords

Antiproliferative activity
HSC-T6
Hovenia dulcis
Rhamnaceae
Triterpenoid

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10.1016/j.phytochem.2017.06.014

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title = "Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells",

abstract = "Three ceanothane-type and three lupane-type triterpenoids, as well as three known compounds, were isolated from the roots of Hovenia dulcis (Rhamnaceae), based on LC–MS dereplication. The previously undescribed compounds were determined to be 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid, 27-O-protocatechuoyl-3-dehydroxycolubrinic acid, 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid, 27-O-protocatechuoylbetulinic acid, 27-O-p-hydroxybenzoylbetulinic acid, and 27-O-syringoylbetulinic acid by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. The isolates were examined for their antiproliferative activity in HSC-T6 hepatic stellate cells; compounds 1, 2, 3, and 6 showed IC50 values in the range of 15–50 μM.",

keywords = "Antiproliferative activity, HSC-T6, Hovenia dulcis, Rhamnaceae, Triterpenoid",

author = "Kang, {Kyo Bin} and Jun, {Jin Bum} and Kim, {Jung Wha} and Kim, {Hyun Woo} and Sung, {Sang Hyun}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

month = oct,

doi = "10.1016/j.phytochem.2017.06.014",

language = "English",

volume = "142",

pages = "60--67",

journal = "Phytochemistry",

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T1 - Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells

AU - Kang, Kyo Bin

AU - Jun, Jin Bum

AU - Kim, Jung Wha

AU - Kim, Hyun Woo

AU - Sung, Sang Hyun

PY - 2017/10

Y1 - 2017/10

N2 - Three ceanothane-type and three lupane-type triterpenoids, as well as three known compounds, were isolated from the roots of Hovenia dulcis (Rhamnaceae), based on LC–MS dereplication. The previously undescribed compounds were determined to be 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid, 27-O-protocatechuoyl-3-dehydroxycolubrinic acid, 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid, 27-O-protocatechuoylbetulinic acid, 27-O-p-hydroxybenzoylbetulinic acid, and 27-O-syringoylbetulinic acid by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. The isolates were examined for their antiproliferative activity in HSC-T6 hepatic stellate cells; compounds 1, 2, 3, and 6 showed IC50 values in the range of 15–50 μM.

AB - Three ceanothane-type and three lupane-type triterpenoids, as well as three known compounds, were isolated from the roots of Hovenia dulcis (Rhamnaceae), based on LC–MS dereplication. The previously undescribed compounds were determined to be 27-O-protocatechuoyl-3-dehydroxyisoceanothanolic acid, 27-O-protocatechuoyl-3-dehydroxycolubrinic acid, 27-O-protocatechuoyl-3-dehydroxyepicolubrinic acid, 27-O-protocatechuoylbetulinic acid, 27-O-p-hydroxybenzoylbetulinic acid, and 27-O-syringoylbetulinic acid by 1D and 2D NMR spectroscopic and HR mass spectrometric data analysis. The isolates were examined for their antiproliferative activity in HSC-T6 hepatic stellate cells; compounds 1, 2, 3, and 6 showed IC50 values in the range of 15–50 μM.

KW - Antiproliferative activity

KW - HSC-T6

KW - Hovenia dulcis

KW - Rhamnaceae

KW - Triterpenoid

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U2 - 10.1016/j.phytochem.2017.06.014

DO - 10.1016/j.phytochem.2017.06.014

M3 - Article

C2 - 28686899

AN - SCOPUS:85021651332

SN - 0031-9422

VL - 142

SP - 60

EP - 67

JO - Phytochemistry

JF - Phytochemistry

ER -

Ceanothane- and lupane-type triterpene esters from the roots of Hovenia dulcis and their antiproliferative activity on HSC-T6 cells

Abstract

Keywords

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