Triterpenoids and steroids with cytotoxic activity from Emmenopterys henryi

Xing De Wu; Juan He; Xing Yao Li; Liao Bin Dong; Xun Gong; Xiu Gao; Liu Dong Song; Yan Li; Li Yan Peng; Qin Shi Zhao

doi:10.1055/s-0033-1350645

Triterpenoids and steroids with cytotoxic activity from Emmenopterys henryi

Xing De Wu
, Juan He
, Xing Yao Li
, Liao Bin Dong
, Xun Gong
, Xiu Gao
, Liu Dong Song
, Yan Li
, Li Yan Peng
, Qin Shi Zhao

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

17 Scopus citations

Abstract

Two new ursane-type triterpenoids, 3β,19α,23-trihydroxyurs-12- en-24-al-28-oic acid (1) and 3β,19α,24-trihydroxy-23-norurs-12-en-28- oic acid (2), two new pregnane derivatives, 3β,12β-dihydroxy-5α- pregnane-14,16-dien-20-one (9) and 12β-hydroxy-5α-pregnane-14,16- dien-3,20-dione (10), and eight known compounds were isolated from the twigs and leaves of Emmenopterys henryi. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR experiments. Compounds 4, 11, and 12 showed cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines with IC₅₀ values in the range of 3.11-20.12 μM.

Original language	English (US)
Pages (from-to)	1356-1361
Number of pages	6
Journal	Planta Medica
Volume	79
Issue number	14
DOIs	https://doi.org/10.1055/s-0033-1350645
State	Published - 2013
Externally published	Yes

Keywords

cytotoxic activity
Emmenopterys henryi
pregnane derivatives
Rubiaceae
ursane-type triterpenoids

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1055/s-0033-1350645

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title = "Triterpenoids and steroids with cytotoxic activity from Emmenopterys henryi",

abstract = "Two new ursane-type triterpenoids, 3β,19α,23-trihydroxyurs-12- en-24-al-28-oic acid (1) and 3β,19α,24-trihydroxy-23-norurs-12-en-28- oic acid (2), two new pregnane derivatives, 3β,12β-dihydroxy-5α- pregnane-14,16-dien-20-one (9) and 12β-hydroxy-5α-pregnane-14,16- dien-3,20-dione (10), and eight known compounds were isolated from the twigs and leaves of Emmenopterys henryi. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR experiments. Compounds 4, 11, and 12 showed cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines with IC50 values in the range of 3.11-20.12 μM.",

keywords = "cytotoxic activity, Emmenopterys henryi, pregnane derivatives, Rubiaceae, ursane-type triterpenoids",

author = "Wu, \{Xing De\} and Juan He and Li, \{Xing Yao\} and Dong, \{Liao Bin\} and Xun Gong and Xiu Gao and Song, \{Liu Dong\} and Yan Li and Peng, \{Li Yan\} and Zhao, \{Qin Shi\}",

year = "2013",

doi = "10.1055/s-0033-1350645",

language = "English (US)",

volume = "79",

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AU - Wu, Xing De

AU - He, Juan

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AU - Dong, Liao Bin

AU - Gong, Xun

AU - Gao, Xiu

AU - Song, Liu Dong

AU - Li, Yan

AU - Peng, Li Yan

AU - Zhao, Qin Shi

PY - 2013

Y1 - 2013

N2 - Two new ursane-type triterpenoids, 3β,19α,23-trihydroxyurs-12- en-24-al-28-oic acid (1) and 3β,19α,24-trihydroxy-23-norurs-12-en-28- oic acid (2), two new pregnane derivatives, 3β,12β-dihydroxy-5α- pregnane-14,16-dien-20-one (9) and 12β-hydroxy-5α-pregnane-14,16- dien-3,20-dione (10), and eight known compounds were isolated from the twigs and leaves of Emmenopterys henryi. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR experiments. Compounds 4, 11, and 12 showed cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines with IC50 values in the range of 3.11-20.12 μM.

AB - Two new ursane-type triterpenoids, 3β,19α,23-trihydroxyurs-12- en-24-al-28-oic acid (1) and 3β,19α,24-trihydroxy-23-norurs-12-en-28- oic acid (2), two new pregnane derivatives, 3β,12β-dihydroxy-5α- pregnane-14,16-dien-20-one (9) and 12β-hydroxy-5α-pregnane-14,16- dien-3,20-dione (10), and eight known compounds were isolated from the twigs and leaves of Emmenopterys henryi. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR experiments. Compounds 4, 11, and 12 showed cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines with IC50 values in the range of 3.11-20.12 μM.

KW - cytotoxic activity

KW - Emmenopterys henryi

KW - pregnane derivatives

KW - Rubiaceae

KW - ursane-type triterpenoids

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Triterpenoids and steroids with cytotoxic activity from Emmenopterys henryi

Abstract

Keywords

ASJC Scopus subject areas

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