Cytotoxic phenylpropanoids and a new triterpene, turformosinic acid, from Turpinia formosana Nakai.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Hui-Chi HuangYao-Haur Kuo

Abstract

One new phenylpropanoid, turformosin A (1), and one new triterpene, turformosinic acid (2), together with 16 known compounds, were isolated from the stems of Turpinia formosana Nakai. All structures were elucidated on the basis of spectroscopic analysis, including 1D- and 2D-NMR techniques and MS analysis. Selected isolated compounds were evaluated for in vitro cytotoxicity against four human cancer cell lines and antioxidant scavenging effects on DPPH. (-)-(7'S,8'S)-threo-carolignan X (3) exhibited cytotoxicity against Hep2, WiDr, Daoy, and MCF-7 cell lines with ED(50) values of 3.60, 4.45, 6.07, and 13.7 μg/mL, respectively. Turformosin A (1), (-)-(7'S,8'S)- threo-carolignan X (3), methoxyhydroquinone-4-β-D-glucopyranoside (5), and methoxy-hydroquinone-1-β-D-glucopyranoside (6), exhibited similar anti-oxidative activity. Hep2 cells treated with 10 μg/mL of 3 showed elevation of sub-G1 population (from 20% at 8 h to 60% at 48 h), and activation of caspase-9/caspase-3/PARP cascade. Compound 3 induced intrinsic apoptotic pathway in Hep2 cells with dose and time dependence (10 μg/mL for 8 h).

References

May 24, 2000·Chemical & Pharmaceutical Bulletin·Y TakedaH Otsuka
Apr 9, 2001·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·F D HorgenN R Farnsworth
Apr 21, 2001·Phytochemistry·A M SecaC Pascoal-Neto
May 31, 2002·Chemical & Pharmaceutical Bulletin·Qian YuYoshio Takeda
Apr 4, 2003·Chemical & Pharmaceutical Bulletin·Yoshihito OkadaToru Okuyama
Apr 15, 2004·Bioorganic & Medicinal Chemistry·Pei-Lin WuTian-Shung Wu
Jul 6, 2005·Chemical & Pharmaceutical Bulletin·Tsutomu NakanishiYoshikazu Sakagami
Jul 6, 2005·Chemical & Pharmaceutical Bulletin·Qian YuYoshio Takeda
Nov 7, 2006·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·F KhalloukiR W Owen
Dec 1, 2006·Journal of Asian Natural Products Research·M-A Ouyang, Y-H Kuo
Jan 18, 2007·Archives of Pharmacal Research·Ki Myun ParkKang Ro Lee
Mar 17, 2007·Natural Product Research·Susan MatthewPedro Abreu
Mar 18, 2010·Journal of Natural Products·Li-Jie ZhangYao-Haur Kuo
Sep 10, 2010·Journal of Natural Products·Chao-Lin ChangYao-Haur Kuo
Sep 22, 2010·Journal of Natural Products·Lynette K LambertMary J Garson

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Citations

Jun 7, 2013·Pharmaceutical Biology·Xueqin MaLuping Qin
Oct 25, 2014·Natural Product Reports·Robert A Hill, Joseph D Connolly
Jan 19, 2019·Chemistry & Biodiversity·Thalía I Ramírez-ReyesJosé A Guerrero-Analco
Jun 30, 2019·International Journal of Molecular Sciences·Zuha ImtiyazMei-Hsien Lee

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Methods Mentioned

BETA
NMR
fluorescence-activated
flow cytometry
column chromatography

Software Mentioned

CellQuest
MM2

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