The triterpenoids and sesquiterpenoids from the plant of Agrimonia pilosa

Jia Zhang; Ya-Nan Yang; Zi-Ming Feng; Xiang Yuan; Xu Zhang; Jian-Shuang Jiang; Pei-Cheng Zhang

doi:10.1016/j.fitote.2021.105104

The triterpenoids and sesquiterpenoids from the plant of Agrimonia pilosa

Fitoterapia. 2022 Mar:157:105104. doi: 10.1016/j.fitote.2021.105104. Epub 2021 Dec 16.

Authors

Jia Zhang¹, Ya-Nan Yang², Zi-Ming Feng², Xiang Yuan², Xu Zhang², Jian-Shuang Jiang³, Pei-Cheng Zhang⁴

Affiliations

¹ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China; School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing 102488, China.
² State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China.
³ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China. Electronic address: jiangjs@imm.ac.cn.
⁴ State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China. Electronic address: pczhang@imm.ac.cn.

PMID: 34923054
DOI: 10.1016/j.fitote.2021.105104

Abstract

A phytochemistry of the whole plant of Agrimonia pilosa led to the discovery of two new nortriterpenoids, agrimonorterpenes A and B (1 and 2), together with one known triterpenoid fupenzic acid (3) and seven known sesquiterpenoids (4-10). The new structures were determined as 19α-hydroxy-2-oxo-nor-A (3)-urs-11,12-dien-28-oic acid (1) and 2, 19β-dihydroxy-3-oxo-23-noroleana-1, 4, 12-trien-28-oic acid (2) by the spectroscopic data of UV, IR, HR-ESI-MS, and NMR. Notably, the structure of 1 possessed a rare five-membered A- ring. And this is the first time to discover the sesquiterpenoids (4-10) from A. pilosa. Compound 3 displayed the selective cytotoxicity against HCT116, BGC823, and HepG2 cell lines with the IC₅₀ values of 16.31 μM, 21.94 μM, and 23.40 μM, respectively.

Keywords: Agrimonia pilosa; Cytotoxicity; Nortriterpenoid; Sesquiterpenoid; Structural elucidation.

MeSH terms

Agrimonia / chemistry*
Glycoside Hydrolase Inhibitors / chemistry
Glycoside Hydrolase Inhibitors / isolation & purification
Glycoside Hydrolase Inhibitors / toxicity
Magnetic Resonance Spectroscopy
Optical Rotation
Sesquiterpenes / chemistry
Sesquiterpenes / isolation & purification*
Sesquiterpenes / toxicity
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Triterpenes / chemistry
Triterpenes / isolation & purification*
Triterpenes / toxicity

Substances

Glycoside Hydrolase Inhibitors
Sesquiterpenes
Triterpenes