Antitumor agents. 239. Isolation, structure elucidation, total synthesis, and anti-breast cancer activity of neo-tanshinlactone from Salvia miltiorrhiza

Journal of Medicinal Chemistry

Volumn 47, Issue 23, 2004, Pages 5816-5819

  Wang, Xihong ^a   Bastow, Kenneth F ^a   Sun, Chang Ming ^c   Lin, Yun Lian ^c   Yu, Hsi Jung ^d   Don, Ming Jaw ^c   Wu, Tian Shung ^b   Nakamura, Seikou ^a   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

^b NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^c NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

^d CHINESE CULTURE UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CRYPTOTANSHINONE; EPIDERMAL GROWTH FACTOR RECEPTOR 2; NEO TANSHINLACTONE; SALVIA MILTIORRHIZA EXTRACT; TAMOXIFEN CITRATE; TANSHINONE I; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL STRAIN MCF 7; CHEMICAL STRUCTURE; CYTOTOXICITY; DRUG SELECTIVITY; DRUG SYNTHESIS; EXTRACTION AND EXTRACTS; HUMAN; HUMAN CELL; IN VITRO STUDY; ISOLATION PROCEDURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALVIA MILTIORRHIZA; STRUCTURE ANALYSIS; TANSHINONE IIA;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BREAST NEOPLASMS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; FURANS; HUMANS; PYRONES; RECEPTOR, ERBB-2; RECEPTORS, ESTROGEN; SALVIA MILTIORRHIZA;

EID: 7444239691     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040112r     Document Type: Article

References (18)

1. Labrie, F.; Labrie, C.; Bélanger, A.; Simard, J.; Gauthier, S.; Luu-The, V.; et al. EM-652 (SCH 57068), a third generation SERM acting as pure antiestrogen in the mammary gland and endometrium. J. Steroid Biochem. Mol. Biol. 1999, 69, 51-84.
2. Jordan, V. C.; Gradishar, W. J. Molecular mechanisms and future uses of antiestrogens. Mol. Aspects Med. 1997, 18, 187-247.
3. Slamon, D. J.; Godolphin, W.; Jones, L. A., et al. Studies of the HER-2/neu proto-oncogene in human breast and ovarian cancer. Science 1989, 244, 707-712.
4. Kinoshita, Y.; Chen, S. Induction of aromatase (CYP19) expression in breast cancer cells through a nongenomic action of estrogen receptor α. Cancer Res. 2003, 63, 3546-3555.
5. Dhingra, K. Antiestrogens-tamoxifen, SERMs and beyond. Invest. New Drugs 1999, 17, 285-311.
6. Ryu, S. Y.; Lee, C. O.; Choi, S. U. In vitro cytotoxicity of tanshinones from Salvia miltiorrhiza. Planta Med. 1997, 63, 339-342.
7. Wu, W.-L.; Chang, W.-L.; Chen, C.-F. Cytotoxic activities of tanshinones against human carcinoma cell lines. Am. J. Chin. Med. 1991, 19, 207-216.
8. Cao, E.-H.; Liu, X.-Q.; Wang, J.-J.; Xu, N.-F. Effect of natural antioxidant tanshinone II-A on DNA damage by lipid peroxidation in liver cells. Free Radic. Biol. Med. 1996, 20, 801-806.
9. Honda, G.; Koezuka, Y.; Tabata, M. Isolation of an antidermatophytic substance from the root of Salvia miltiorrhiza. Chem. Pharm. Bull. 1988, 36, 408-411.
10. Onitsuka, M.; Fujiu, M.; Shinma, N.; Maruyama, H. B. New platelet aggregation inhibitors from Tan-Shen; radix of Salvia miltiorrhiza Bunge. Chem. Pharm. Bull. 1983, 31, 1670-1675.
11. Lin, H. C.; Ding, H. Y.; Chang, W. L. Two new fatty diterpenoids from Salvia miltiorrhiz. J. Nat. Prod. 2001, 64, 648-650.
12. Ryu, S. Y.; Lee, C. O.; Choi, S. U. Inhibition of mast cell degranulation by tanshinones from the roots of Salvia miltiorrhiza. Planta Med. 1999, 65, 654-655.
13. Luo, H.-W.; Ji, J.; Wu, M.-Y.; Yong, Z.-G.; Niwa, M.; and Hirata, Y. Tanshinlactone, a novel seco-abietanoid from Salvia miltiorrhiza. Chem. Pharm. Bull. 1986, 34, 3166-3168.
14. Suh, Y.-G.; Shin, D.-Y.; Min, K. H.; Hyun, S.-S.; Jung, J.-K.; Seo, S.-Y. Facile construction of the oxaphenalene skeleton by peri ring closure, formal synthesis of Mansonone F. Chem. Commun. 2000, 1203-1204.
15. Mayer, P.; Alibert, S.; Brunel, P.; Imbert, T. Synthesis of benzo-[de]chromene analogue of Efaroxan. Heterocycles 2000, 55, 387-392.
16. Kamijo, H.; Takido, T.; Nakazawa, T.; Itabashi, K.; Seno, M. Synthesis of 3-hydroxy-1H-phenalen-1-ones from methylthionaphthalenes with malonic acids. Nippon Kagaku Kaishi 1993, 11, 1257-1262.
17. Risitano, F.; Grassi, G.; Foti, F.; Bilardo, C. A convenient synthesis of furo[3,2-c]coumarins by a tandem alkylation/intramolecular aldolization reaction. Tetrahedron Lett. 2001, 42, 3503-3505.
18. Nakanishi, Y.; Chang, F.-R.; Liaw, C.-C.; Wu, Y.-C.; Bastow, K. F.; Lee, K.-H. Acetogenins as selective inhibitors of the human ovarian 1A9 tumor cell line. J. Med. Chem. 2003, 46, 3185.