Xanthones from the roots of Maclura cochinchinensis var. gerontogea and their retinoic acid receptor-α agonistic activity

Ken-ichi Nakashima; Toshiyuki Tanaka; Hiroko Murata; Kouichi Kaburagi; Makoto Inoue

doi:10.1016/j.bmcl.2015.02.075

Xanthones from the roots of Maclura cochinchinensis var. gerontogea and their retinoic acid receptor-α agonistic activity

Bioorg Med Chem Lett. 2015 May 1;25(9):1998-2001. doi: 10.1016/j.bmcl.2015.02.075. Epub 2015 Mar 7.

Authors

Ken-ichi Nakashima¹, Toshiyuki Tanaka², Hiroko Murata³, Kouichi Kaburagi, Makoto Inoue⁴

Affiliations

¹ Laboratory of Medicinal Resources, School of Pharmacy, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya, Aichi 464-8650, Japan.
² Laboratory of Natural Resources, Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu, Gifu 501-1196, Japan.
³ Faculty of Pharmaceutical Sciences, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
⁴ Laboratory of Medicinal Resources, School of Pharmacy, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya, Aichi 464-8650, Japan. Electronic address: minoue@dpc.aichi-gakuin.ac.jp.

PMID: 25838141
DOI: 10.1016/j.bmcl.2015.02.075

Abstract

A new xanthone (1) and a new naturally occurring xanthone (2) were isolated from the roots of Maclura cochinchinensis (Lour.) Corner var. gerontogea (Sieb. et Zucc.) Ohashi together with 10 known xanthones (3-12). Their structures were established by spectroscopic analyses including 1D and 2D NMR. Their retinoic acid receptor-α agonistic activity was evaluated using a luciferase reporter assay. Compound 2, gerontoxanthone A (3), gerontoxanthone B (4), and cudraxanthone I (11) showed moderate concentration-dependent activity. Furthermore, these four xanthones synergistically increased transcriptional activity in this assay in the presence of bexarotene, an RXR agonist.

Keywords: Bioactive natural compound; Maclura cochinchinensis var. gerontogea; Moraceae; Retinoic acid receptor-α; Xanthone.

MeSH terms

Dose-Response Relationship, Drug
Humans
Maclura / chemistry*
Molecular Structure
Plant Roots / chemistry*
Receptors, Retinoic Acid / agonists*
Retinoic Acid Receptor alpha
Structure-Activity Relationship
Xanthones / chemistry
Xanthones / isolation & purification
Xanthones / pharmacology*

Substances

RARA protein, human
Receptors, Retinoic Acid
Retinoic Acid Receptor alpha
Xanthones