Alkaloids and styryllactones from Goniothalamus cheliensis

Wuttichai Jaidee; Raymond J Andersen; Brian O Patrick; Stephen G Pyne; Chatchai Muanprasat; Suparerk Borwornpinyo; Surat Laphookhieo

doi:10.1016/j.phytochem.2018.10.014

Alkaloids and styryllactones from Goniothalamus cheliensis

Phytochemistry. 2019 Jan:157:8-20. doi: 10.1016/j.phytochem.2018.10.014. Epub 2018 Oct 20.

Authors

Wuttichai Jaidee¹, Raymond J Andersen², Brian O Patrick², Stephen G Pyne³, Chatchai Muanprasat⁴, Suparerk Borwornpinyo⁵, Surat Laphookhieo⁶

Affiliations

¹ Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang Rai 57100, Thailand; School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand.
² Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.
³ School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.
⁴ Department of Physiology, Faculty of Science, Mahidol University, Rajathevi, Bangkok 10400, Thailand; Excellent Center for Drug Discovery, Faculty of Science, Mahidol University, Rajathevi, Bangkok 10400, Thailand.
⁵ Department of Biotechnology, Faculty of Science, Mahidol University, Rajathevi, Bangkok 10400, Thailand.
⁶ Center of Chemical Innovation for Sustainability (CIS), Mae Fah Luang University, Chiang Rai 57100, Thailand; School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand. Electronic address: surat.lap@mfu.ac.th.

PMID: 30352328
DOI: 10.1016/j.phytochem.2018.10.014

Abstract

Eight previously undescribed compounds, including four alkaloids and five styryllactones together with 36 known compounds were isolated from the twig and leaf extracts of Goniothalamus cheliensis. Their structures were elucidated by extensive analysis of their spectroscopic data. The absolute configuration of (-)-(4S,5S,6R,7S,8S)-goniochelienlactone and (-)-(4S,5S,6R,7S,8S)-7-acetylgoniochelienlactone were established from single crystal X-ray analysis using Cu Kα radiation. The absolute configurations of the other related compounds were identified by comparisons of their ECD spectra with those of related known compounds. Most of the isolated compounds were evaluated for their cytotoxicities against human colorectal cancer cells (HCT-116). Griffithazanone A was the most potent with an IC₅₀ value of 2.39 μM.

Keywords: Alkaloids; Annonaceae; Goniothalamus cheliensis; Styryllactones.

MeSH terms

Alkaloids / chemistry*
Alkaloids / isolation & purification
Alkaloids / pharmacology*
Antineoplastic Agents, Phytogenic / chemistry*
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Goniothalamus / chemistry*
HCT116 Cells
Humans
Lactones / chemistry*
Lactones / isolation & purification
Lactones / pharmacology*
Models, Molecular
Molecular Conformation

Substances

Alkaloids
Antineoplastic Agents, Phytogenic
Lactones