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Planta Med 2022; 88(06): 420-428
DOI: 10.1055/a-1495-5963
Biological and Pharmacological Activity
Original Papers

New Sulfoxide-Containing Derivatives from the Resin of Ferula sinkiangensis

Junchi Wang
1   The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
,
Haoli Yan
2   Center for Food and Drug Evaluation & Inspection of Henan, Zhengzhou, China
,
Xiaoshuang Huo
1   The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
,
Lingyu Li
1   The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
,
Huijuan Wang
1   The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
,
Meng Zhang
1   The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
,
Xiaojin Li
3   Xinjiang Institute of Chinese Materia Medica and Ethical Materia Medica, Urumqi, China
,
Yaqin Zhao
3   Xinjiang Institute of Chinese Materia Medica and Ethical Materia Medica, Urumqi, China
,
Gang Chen
3   Xinjiang Institute of Chinese Materia Medica and Ethical Materia Medica, Urumqi, China
,
Jianyong Si 
1   The Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
› Author AffiliationsSupported by: National Natural Science Foundation of China 81903920
Supported by: CAMS Innovation Fund for Medical Sciences 2017-I2M-1-013
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Abstract

Four undescribed sulfoxide-containing derivatives, sinkiangenoxides A and B, (2Z, 4E)-sinkiangenoxide C, and (2E, 4E)-sinkiangenoxide C (1 – 4), and one known compound, 1-(methylthio)propyl (E)-1-propenyl disulfide (5), were isolated from the resin of Ferula sinkiangensis. Their structures were determined based on spectroscopic methods, including IR, UV, HRESIMS, NMR, and CD analysis. Compounds 2 – 4 showed moderate cytotoxic activities against four human cancer cell lines with IC50 values ranging from 15.0 to 40.3 µM. Sinkiangenoxide B (2) was shown to induce apoptosis in HepG2 cells. In addition, compound 5 effectively attenuated lipopolysaccharide-induced nitric oxide release and TNF-α, IL-1β, IL-6, and IL-10 expression.

Key words

Ferula sinkiangensis - Apiaceae - sulfoxide - structural elucidation - cytotoxic - NO release

Supporting Information

    IR, UV, HRESIMS, 1D, and 2D NMR spectra of the new compounds, ECD spectra, chiral separation, and cytotoxicity at various concentrations of 2 – 4 are available as Supporting Information.

  • Supporting Information


Publication History

Received: 20 September 2020

Accepted after revision: 19 April 2021

Article published online:
20 May 2021

© 2021. Thieme. All rights reserved.

Georg Thieme Verlag KG
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