Three Previously Undescribed Chlorophenyl Glycosides from the Bulbs of Lilium regale

• Published in: Chemistry & biodiversity 2021-10, Vol.18 (10), p.e2100403-n/a
• Main Authors: Yan, Jie, Guo, Wenxiu, Zhou, Lanyu, Guo, Dale, Pei, Jin, Deng, Yun, Zheng, Haoyuan, Liu, Ding, Xie, Xiaofang, Peng, Cheng
• Format: Article
• Language: English
• Subjects: A549 Cells; anti-proliferative activity; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Cell proliferation; Cell Proliferation - drug effects; chlorophenyl glycosides; Drug Screening Assays, Antitumor; Glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Humans; Lilium - chemistry; Lilium regale; Lung cancer; Lung carcinoma; Molecular Conformation; Plant Roots - chemistry; structural elucidation; Tumor Cells, Cultured
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.202100403

Three previously undescribed chlorophenyl glycosides, (2,4,6‐trichloro‐3‐hydroxy‐5‐methoxyphenyl)methyl β‐D‐glucopyranoside (1), (2,4‐dichloro‐3,5‐dimethoxyphenyl)methyl 6‐O‐β‐D‐glucopyranosyl‐β‐D‐glucopyranoside (2) and 4‐chloro‐3‐methoxy‐5‐methylphenyl 6‐O‐(6‐deoxy‐β‐L‐mannopyranosyl)‐β‐D‐glucopyranoside (3) were obtained from Lilium regale. The absolute configurations of these new finds were elucidated by comprehensive analyses of spectroscopic data combined with acid hydrolysis derivatization. (2,4‐dichloro‐3,5‐dimethoxyphenyl)methyl 6‐O‐β‐D‐glucopyranosyl‐β‐D‐glucopyranoside (2) can inhibit the proliferation of lung carcinoma A549 cells with an IC50 value of 29 μΜ.