Cytotoxic cardenolides and sesquiterpenoids from the fruits of Reevesia formosana

Pei-Yu Hsiao; Shiow-Ju Lee; Ih-Sheng Chen; Hsing-Yu Hsu; Hsun-Shuo Chang

doi:10.1016/j.phytochem.2016.06.009

Cytotoxic cardenolides and sesquiterpenoids from the fruits of Reevesia formosana

Phytochemistry. 2016 Oct:130:282-90. doi: 10.1016/j.phytochem.2016.06.009. Epub 2016 Jul 4.

Authors

Pei-Yu Hsiao¹, Shiow-Ju Lee², Ih-Sheng Chen³, Hsing-Yu Hsu², Hsun-Shuo Chang⁴

Affiliations

¹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC.
² Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes, Miaoli, 350, Taiwan, ROC.
³ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC; School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC; Research Center for Natural Products and Drug Development, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC.
⁴ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC; School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC; Research Center for Natural Products and Drug Development, Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC; Center for Infectious Disease and Cancer Research (CICAR), Kaohsiung Medical University, Kaohsiung, 807, Taiwan, ROC. Electronic address: hschang@kmu.edu.tw.

PMID: 27386738
DOI: 10.1016/j.phytochem.2016.06.009

Abstract

Bioassay-guided fractionation of the fruits of Reevesia formosana led to isolation of three cardenolides (reevesioside J, reevesioside K, and epi-reevesioside K), three sesquiterpenoids (reevesiterpenol C, reevesiterpenol D, and reevesiterpenol E), and two glycosides (reevesianin A and reevesianin B), along with 46 known compounds. Their structures were determined using spectroscopic techniques. In addition to the reported cytotoxic cardenolides, reevesioside J and strophanthidin exhibited moderate cytotoxicity against the cell lines MCF-7, NCI-H460, and HepG2, with IC50 values of 0.39 ± 0.06 μM and 1.06 ± 0.12 μM for MCF-7, 0.12 ± 0.01 μM and 0.29 ± 0.01 μM for NCI-H460, and 1.09 ± 0.02 μM and 1.72 ± 0.02 μM for HepG2, respectively. Reevesiterpenol E also exhibited the best selective cytotoxicity to the NCI-H460 cell line, with an IC50 value of 3.15 ± 0.22 μM.

Keywords: Cardenolides; Cytotoxicity; Reevesia formosana; Sesquiterpenoids; Sterculiaceae.

MeSH terms

Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology
Cardenolides / chemistry
Cardenolides / isolation & purification*
Cardenolides / pharmacology*
Cell Proliferation / drug effects
Drug Screening Assays, Antitumor
Female
Fruit / chemistry*
Glycosides / chemistry
Glycosides / isolation & purification*
Glycosides / pharmacology*
Hep G2 Cells
Humans
MCF-7 Cells
Malvaceae / chemistry*
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / pharmacology*
Sesterterpenes

Substances

Antineoplastic Agents, Phytogenic
Cardenolides
Glycosides
Sesquiterpenes
Sesterterpenes
reevesioside J
reevesioside K
reevesiterpenol C
reevesiterpenol D
reevesiterpenol E