Chamaejasmins, cytotoxic guaiane sesquiterpenes from the root of Stellera chamaejasme L

Ahmed H H El-Desoky; Keisuke Eguchi; Hikaru Kato; Naoki Kishimoto; Shogo Misumi; Takashi Watanabe; Sachiko Tsukamoto

doi:10.1016/j.fitote.2020.104714

Chamaejasmins, cytotoxic guaiane sesquiterpenes from the root of Stellera chamaejasme L

Fitoterapia. 2020 Oct:146:104714. doi: 10.1016/j.fitote.2020.104714. Epub 2020 Aug 26.

Authors

Ahmed H H El-Desoky¹, Keisuke Eguchi², Hikaru Kato², Naoki Kishimoto³, Shogo Misumi³, Takashi Watanabe⁴, Sachiko Tsukamoto⁵

Affiliations

¹ Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan; Pharmaceutical Industries Research Division, Pharmacognosy Department, National Research Centre, 33 El Bohouth St. (Former El Tahrir St.), Dokki, P.O. 12622, Giza, Egypt.
² Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
³ Department of Environmental and Molecular Health Sciences, Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
⁴ Department of Medicinal Botany, Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
⁵ Department of Natural Medicines, Graduate School of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan. Electronic address: sachiko@kumamoto-u.ac.jp.

PMID: 32858173
DOI: 10.1016/j.fitote.2020.104714

Abstract

Four new guaiane-type sesquiterpenes, chamaejasmins A-D (1-4), were isolated from the root of Stellera camaejasme L. collected in Nepal, together with two known terpenes, stelleraguaianone B (5) and 1α,7α,10αH-guaia-4,11-dien-3-one (6). The structures of 1-4 including their absolute configurations were determined by extensive 2D NMR analyses, mass spectroscopy, and TDDFT calculations of their ¹³C chemical shifts and ECD spectra. Chamaejasmin A (1) showed cytotoxicity against HeLa cells with an IC₅₀ value of 6.3 μM.

Keywords: Chamaejasmin; Cytotoxicity; Sesquiterpene; Stellera chamaejasme L..

MeSH terms

Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Flavonoids / isolation & purification
Flavonoids / pharmacology*
HeLa Cells
Humans
Molecular Structure
Nepal
Phytochemicals / isolation & purification
Phytochemicals / pharmacology
Plant Roots / chemistry
Sesquiterpenes, Guaiane / isolation & purification
Sesquiterpenes, Guaiane / pharmacology*
Thymelaeaceae / chemistry*

Substances

Antineoplastic Agents, Phytogenic
Flavonoids
Phytochemicals
Sesquiterpenes, Guaiane
chamaejasmin