Bidysoxyphenols A-C, dimeric sesquiterpene phenols from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm

Ferry Ferdiansyah Sofian; Anas Subarnas; Mayuka Hakozaki; Shota Uesugi; Takuya Koseki; Yoshihito Shiono

doi:10.1016/j.fitote.2022.105157

Bidysoxyphenols A-C, dimeric sesquiterpene phenols from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm

Fitoterapia. 2022 Apr:158:105157. doi: 10.1016/j.fitote.2022.105157. Epub 2022 Feb 14.

Authors

Ferry Ferdiansyah Sofian¹, Anas Subarnas², Mayuka Hakozaki³, Shota Uesugi³, Takuya Koseki⁴, Yoshihito Shiono⁵

Affiliations

¹ The United Graduate School of Agricultural Sciences, Iwate University, Morioka, Iwate 020-8550, Japan; Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan; Department of Pharmaceutical Biology, Faculty of Pharmacy, Universitas Padjadjaran, Sumedang, Jatinangor 45363, Indonesia. Electronic address: ferry.ferdiansyah@unpad.ac.id.
² Department of Pharmacology and Clinical Pharmacy, Faculty of Pharmacy, Universitas Padjadjaran, Sumedang, Jatinangor 45363, Indonesia.
³ Iwate Biotechnology Research Center, Kitakami, Iwate 024-0003, Japan.
⁴ Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan.
⁵ The United Graduate School of Agricultural Sciences, Iwate University, Morioka, Iwate 020-8550, Japan; Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan. Electronic address: yshiono@tds1.tr.yamagata-u.ac.jp.

PMID: 35176422
DOI: 10.1016/j.fitote.2022.105157

Abstract

Three new sesquiterpene phenol dimers, bidysoxyphenols A-C (2-4), along with two known compounds, namely sesquiterpene phenol (1) and ionone derivatives (5), were isolated from the leaves of Dysoxylum parasiticum (Osbeck) Kosterm. The structures of these new compounds, including their absolute configurations, were elucidated by nuclear magnetic resonance spectroscopy, ultraviolet spectroscopy, infrared spectroscopy, high-resolution electrospray ionization time-of-flight mass spectrometry, and electronic circular dichroism. Compounds 1 and 2 showed cytotoxicity against human promyelocytic leukemia cells, with IC₅₀ values of 18.25 ± 1.52 and 39.04 ± 3.12 μM, respectively.

Keywords: Cytotoxicity; Dysoxylum parasiticum; HL60 cells; Meliaceae; Sesquiterpene phenol dimers.

MeSH terms

Humans
Meliaceae* / chemistry
Molecular Structure
Phenols / analysis
Plant Leaves / chemistry
Sesquiterpenes* / chemistry

Substances

Phenols
Sesquiterpenes