Dimeric progestins from rhizomes of Ligusticum chuanxiong

Phytochemistry
L S LimE L Yong

Abstract

Five dimeric phthalides were isolated from rhizomes of Ligusticum chuanxiong and their structures deduced based on spectral data. All compounds and their parent extracts were assessed for progesterone-like activity using a progesterone receptor driven reporter-gene bioassay. Among all the compounds, riligustilide, displayed weak progesterone-like activity (EC50 approximately 81 microM), whereas, (3Z')-(3a'R,6'R,3R,6R,7R)-3,8-dihydro-6.6',7.3a'-diligustilide (Mr: 382, EC50 approximately 90 nM), was found to be a potent and specific activator of the progesterone receptor. Levistolide A, although having a very similar plenary structure, was inactive indicating the importance of stereochemistry of chiral centers and flexibility of butylidene side chain for progestogenic activity. These bioactive phthalides and their parent extracts (EC50 approximately 8 microg/ml) may have utility for treatment of conditions requiring progesterone action.

References

Apr 17, 2003·Proceedings of the National Academy of Sciences of the United States of America·C J LoyE L Yong
Apr 6, 2004·Maturitas·Regine Sitruk-Ware
May 29, 2004·Science·Judith L TurgeonPhyllis M Wise
Nov 16, 2004·Mechanisms of Ageing and Development·Xiaotao LiBert W O'Malley
May 26, 2005·Molecular Endocrinology·Bert W O'Malley
Jul 23, 2008·Perspectives in Vascular Surgery and Endovascular Therapy·Kimon Bekelis, Nicos Labropoulos

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Citations

Nov 28, 2013·Journal of Asian Natural Products Research·Jian HuangJin-Hui Wang
Feb 26, 2010·Journal of Asian Natural Products Research·Xin-Liang ChangJi-Jun Chen
Sep 20, 2011·Natural Product Research·Xing-Nuo LiJi-Zhong Yan
Jul 31, 2013·The American Journal of Chinese Medicine·Chun-Mei LiShun-Wan Chan
Aug 27, 2013·Fitoterapia·Jian HuangJin-Hui Wang
Jul 14, 2010·Fitoterapia·Cuiping MiaoYouwei Chen
Aug 1, 2008·Journal of Chromatography. a·Lunzhao YiDalin Yuan
Jul 16, 2011·Magnetic Resonance in Chemistry : MRC·Alejandra LeónGuillermo Delgado
Sep 8, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Weixia LiJin-Ao Duan
Jul 9, 2020·Organic & Biomolecular Chemistry·Xu ZhangPei-Cheng Zhang
Mar 10, 2017·Journal of Asian Natural Products Research·Wei WeiXiu-Wei Yang
Oct 22, 2011·Pharmaceutical Biology·Xia RanLu-Ping Qin

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