Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar

Nwet Nwet Win; So-Yeun Woo; Hla Ngwe; Prema; Chin Piow Wong; Takuya Ito; Yasuko Okamoto; Masami Tanaka; Hiroshi Imagawa; Yoshinori Asakawa; Ikuro Abe; Hiroyuki Morita

doi:10.1016/j.fitote.2018.03.002

Tetrahydrofuran lignans: Melanogenesis inhibitors from Premna integrifolia wood collected in Myanmar

Fitoterapia. 2018 Jun:127:308-313. doi: 10.1016/j.fitote.2018.03.002. Epub 2018 Mar 11.

Authors

Nwet Nwet Win¹, So-Yeun Woo², Hla Ngwe³, Prema⁴, Chin Piow Wong², Takuya Ito², Yasuko Okamoto⁵, Masami Tanaka⁵, Hiroshi Imagawa⁵, Yoshinori Asakawa⁵, Ikuro Abe⁶, Hiroyuki Morita⁷

Affiliations

¹ Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan; Department of Chemistry, University of Yangon, Yangon 11041, Myanmar. Electronic address: nwetwin2012@gmail.com.
² Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
³ Department of Chemistry, University of Yangon, Yangon 11041, Myanmar.
⁴ Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan; Department of Chemistry, University of Yangon, Yangon 11041, Myanmar.
⁵ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
⁶ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁷ Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: hmorita@inm.u-toyama.ac.jp.

PMID: 29540314
DOI: 10.1016/j.fitote.2018.03.002

Abstract

Two new tetrahydrofuran lignans, taungtangyiols A (1) and B (2), and eight known furofuran lignans (3-10), were isolated from the chloroform extract of Premna integrifolia wood collected in Myanmar. Their structures were elucidated by extensive spectroscopic techniques. The X-ray crystal structure of 1 clearly indicated its relative configuration. Taungtangyiols A (1) and B (2) inhibited the deposition of melanin in B16F10 mouse melanoma cells, with IC₅₀ values of 50.7 and 40.9 μM, respectively, without notable cytotoxicity. An SAR study demonstrated that the furofuran and dioxymethylene moieties of the lignans play a vital role in inhibiting melanogenesis.

Keywords: Melanogenesis inhibitory activity; Premna integrifolia; Taungtangyiol; Tetrahydrofuran lignan.

MeSH terms

Animals
Cell Line, Tumor
Furans / isolation & purification*
Lamiaceae / chemistry*
Lignans / isolation & purification*
Melanins / antagonists & inhibitors*
Melanoma, Experimental
Mice
Molecular Structure
Myanmar
Wood / chemistry*

Substances

Furans
Lignans
Melanins
tetrahydrofuran