Erythrosaponins A-J, triterpene saponins from the roots and stem bark of Gardenia erythroclada

Sutin Kaennakam; Thammarat Aree; Jantana Yahuafai; Pongpun Siripong; Santi Tip-Pyang

doi:10.1016/j.phytochem.2018.04.016

Erythrosaponins A-J, triterpene saponins from the roots and stem bark of Gardenia erythroclada

Phytochemistry. 2018 Aug:152:36-44. doi: 10.1016/j.phytochem.2018.04.016. Epub 2018 May 3.

Authors

Sutin Kaennakam¹, Thammarat Aree¹, Jantana Yahuafai², Pongpun Siripong², Santi Tip-Pyang³

Affiliations

¹ Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
² Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, 10400, Thailand.
³ Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand. Electronic address: santi.ti@chula.ac.th.

PMID: 29730582
DOI: 10.1016/j.phytochem.2018.04.016

Abstract

Ten undescribed triterpene saponins, named erythrosaponins A-J, along with one known analogue were isolated from the roots and stem bark of Gardenia erythroclada. Their structures were determined on the basis of extensive 1D and 2D NMR analyses. Absolute structure of erythrosaponin A was unequivocally affirmed by single-crystal X-ray crystallography. All isolated compounds were evaluated for their cytotoxicity against cancer cell lines (KB and HeLa S-3) and their anti-inflammatory activity based on the inhibition of NO production in RAW264.7 cells. Erythrosaponin D showed moderate cytotoxicity against KB and HeLa S-3 cells with IC₅₀ values of 25.8 and 29.5 μM, respectively. Erythrosaponins D, F, G, I and J showed moderate anti-inflammatory with IC₅₀ values in the range of 63.0-81.4 μM.

Keywords: Erythrosaponins A–J; Gardenia erythroclada; Rubiaceae; Triterpene saponins.

MeSH terms

Animals
Anti-Inflammatory Agents, Non-Steroidal / chemistry
Anti-Inflammatory Agents, Non-Steroidal / isolation & purification
Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Cell Proliferation / drug effects
Crystallography, X-Ray
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
HeLa Cells
Humans
KB Cells
Lipopolysaccharides / antagonists & inhibitors
Lipopolysaccharides / pharmacology
Mice
Models, Molecular
Molecular Structure
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide / biosynthesis
RAW 264.7 Cells
Saponins / chemistry
Saponins / isolation & purification
Saponins / pharmacology*
Structure-Activity Relationship
Triterpenes / chemistry
Triterpenes / isolation & purification
Triterpenes / pharmacology*

Substances

Anti-Inflammatory Agents, Non-Steroidal
Antineoplastic Agents, Phytogenic
Lipopolysaccharides
Saponins
Triterpenes
Nitric Oxide