Planta Med 2007; 73(7): 696-698
DOI: 10.1055/s-2007-981541
Natural Product Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Two New Thiophenes from Echinops latifolius and their Phototoxic Activities

Yi Wang1 , Xian Li1 , Lin-Hao Li2 , Da-Li Meng1 , Zhan-Lin Li1 , Ning Li1
  • 1Research Department of Natural Medicine, Shenyang Pharmaceutical University, Shenyang, P.R. China
  • 2School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, P.R. China
Further Information

Publication History

Received: November 7, 2006 Revised: May 6, 2007

Accepted: May 8, 2007

Publication Date:
13 June 2007 (online)

Abstract

Two new thiophenes, 5-{4-[4-(5-pent-1,3-diynylthiophen-2-yl)-but-3-ynyloxy]-but-1-ynyl}-2,2′-bithiophene (1) and 5-(4-hydroxybut-1-one)-2,2′-bithiophene (2), together with two known thiophenes 5-(4-hydroxybut-1-ynyl)-2,2′-bithiophene (3) and 5-(3,4-dihydroxybut-1-ynyl)-2,2′-bithiophene (4), were isolated from the roots of Echinops latifolius Tausch. Their structures were elucidated based on the detailed NMR spectroscopic analysis and comparison with literature values. Compounds 1 and 2 showed significant inhibition activities against human cancer cell lines A375-S2 and HeLa with IC50 values from 3.1 to 13.5 μmol/L, depending on their exposure to long wavelength ultraviolet light.

References

  • 1 National Pharmacopoeia Committee. Pharmacopoeia of PRC. Beijing; Chemical Industry Press 2005: 183-4.
  • 2 Lu H C, Wang S X, Zhu T R. studies on the chemical constituents of Yuzhou Loulu.  Chin Tradit Herb Drugs. 1989;  20 2-5.
  • 3 Hudson J B, Harris L, Marles R J, Arnason J T. The anti-HIV activities of photoactive terthiophenes.  Photochem Photobiol. 1993;  58 246-50.
  • 4 Mares D, Fasulo M P, Bruni A. ultraviolet-mediated antimycotic activity of α-terthienyl on Microsporum cookie .  J Med Vet Mycol. 1990;  28 469-77.
  • 5 Sharma A, Goel H C. Some naturally occurring phytophototoxins for mosquito control.  Indian J Exp Biol. 1994;  32 745-51.
  • 6 Marles R J, Hudson J B, Graham E A, Soucy-Breau C, Abou-Zaid M, Arnason J T. et al . Structure-activity studies of photoactivated antiviral and cytotoxic tricyclic thiophenes.  Photochem Photobiol. 1992;  56 479-87.
  • 7 He L Y. Methods and applications of plane chromatography. Beijing; Chemical Industry Press 2000: 141.
  • 8 Abegaz B M. Polyacetylenic thiophenes and terpenoids from the roots of Echinops pappii .  Phytochemistry. 1991;  30 879-81.
  • 9 Liu Y, Ye M, Guo H Z, Zhao Y Y, Guo D A. New thiophenes from Echinops grijisii .  J Asian Nat Prod. 2002;  4 175-8.
  • 10 Christensen L P, Lam J. Acetylenes and related compounds in Cynareae.  Phytochemistry. 1990;  29 2753-85.
  • 11 Christensen L P, Lam J. Acetylenes and related compounds in Heliantheae.  Phytochemistry. 1991;  30 11-49.
  • 12 Bohlmann F, Zdero C, Ahmed M. Naturally occurring terpene derivatives. Part 422. New sesquiterpene lactones, geranyllinalol derivatives, and other constituents from Geigeria species.  Phytochemistry. 1982;  21 1679-91.
  • 13 Lin Y L, Huang R L, Kuo Y H, Chen C F. Thiophenes from Echinops grijsii Hance.  Chin Pharm J. 1999;  51 201-11.
  • 14 Hudson J B, Towers H N. Therapeutic potential of plant photosensitizers.  Pharmacol Ther. 1991;  49 181-222.
  • 15 Hudson J B, Graham E A, Lam J, Towers H N. Ultraviolet-dependent biological activities of selected polyines of the Asteraceae.  Planta Med. 1991;  57 69-73.

Prof. Xian Li

Research Department of Natural Medicine

Shenyang Pharmaceutical University

Box 49

Shenyang 110016

People’s Republic of China

Phone: +86-24-2398-6475

Email: proflixian@163.com

    >