Garcowacinols A-J, cytotoxic polyprenylated benzoylphloroglucinol derivatives from the twigs of Garcinia cowa

Sutin Kaennakam; Edwin R Sukandar; Pattama Phasuthan; Jantana Yahuafai; Prayumat Onsrisawat; Fadjar Mulya; Vudhichai Parasuk; Preecha Phuwapraisirisan; Santi Tip-Pyang

doi:10.1016/j.phytochem.2023.113622

Garcowacinols A-J, cytotoxic polyprenylated benzoylphloroglucinol derivatives from the twigs of Garcinia cowa

Phytochemistry. 2023 May:209:113622. doi: 10.1016/j.phytochem.2023.113622. Epub 2023 Feb 26.

Authors

Sutin Kaennakam¹, Edwin R Sukandar², Pattama Phasuthan³, Jantana Yahuafai⁴, Prayumat Onsrisawat⁴, Fadjar Mulya⁵, Vudhichai Parasuk⁵, Preecha Phuwapraisirisan², Santi Tip-Pyang²

Affiliations

¹ Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok, 10800, Thailand. Electronic address: Sutin.k@sci.kmutnb.ac.th.
² Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
³ Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok, 10800, Thailand.
⁴ Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, 10400, Thailand.
⁵ Center of Excellence in Computational Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.

PMID: 36849096
DOI: 10.1016/j.phytochem.2023.113622

Abstract

Ten undescribed polyprenylated benzoylphloroglucinol derivatives named garcowacinols A‒J (1-10) and four known analogues (11-14) were isolated from the twigs of Garcinia cowa. Their structures were determined by spectroscopic data analysis (1D and 2D NMR and HRESIMS), and their absolute configurations were established based on NOESY and ECD data. All isolated compounds were evaluated for their cytotoxicity against five types of human cancer cells (KB, HeLa S3, MCF-7, Hep G2, and HT-29) as well as Vero cells by MTT colorimetric assay. Garcowacinol C was significantly active against all the five cancer cells with IC50 values in the range of 0.61-9.50 μM. Selective proliferative inhibitions were observed on garcowacinol F and 7-epiclusianone against KB cells, and guttiferone Q toward MCF-7 cells with IC50 values less than 10 μM.

Keywords: Benzoylphloroglucinol; Clusiaceae; Cytotoxic; Garcinia cowa; Garcowacinol.

MeSH terms

Animals
Antineoplastic Agents*
Antineoplastic Agents, Phytogenic* / chemistry
Antineoplastic Agents, Phytogenic* / pharmacology
Chlorocebus aethiops
Garcinia* / chemistry
Humans
Molecular Structure
Vero Cells
Xanthones* / chemistry

Substances

Antineoplastic Agents, Phytogenic
Xanthones
Antineoplastic Agents