Benzoxazinoids from Scoparia dulcis (sweet broomweed) with antiproliferative activity against the DU-145 human prostate cancer cell line

Phytochemistry

Volumn 83, Issue , 2012, Pages 110-115

  Wu, Wan Hsun ^a   Chen, Tzu Yu ^b   Lu, Rui Wen ^b   Chen, Shui Tein ^a   Chang, Chia Chuan ^b  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

^b NATIONAL RESEARCH INSTITUTE OF CHINESE MEDICINE   (Taiwan)

Author keywords

Benzoxazinoid glycoside; Flavonoid; Scoparia dulcis; Scrophulariaceae

Indexed keywords

ANTINEOPLASTIC AGENT; BENZOXAZINE DERIVATIVE;

ARTICLE; CELL PROLIFERATION; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECT; DRUG SCREENING; HUMAN; ISOLATION AND PURIFICATION; SCOPARIA; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BENZOXAZINES; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR CONFORMATION; SCOPARIA; STRUCTURE-ACTIVITY RELATIONSHIP;

SCOPARIA; SCOPARIA DULCIS; SCROPHULARIACEAE;

EID: 84867037706     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.07.022     Document Type: Article

References (34)

1. S. Asano, M. Mizutani, T. Hayashi, N. Morita, and N. Takeguchi Reversible inhibitions of gastric H+, K(+)-ATPase by scopadulcic acid B and diacetyl scopadol. New biochemical tools of H+, K(+)-ATPase J. Biol. Chem. 265 1990 22167 22173
2. A. Baumeler, M. Hesse, and C. Werner Benzoxazinoids-cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae) Phytochemistry 53 2000 213 222
3. H.R. Bravo, S.V. Copaja, and W. Lazo Antimicrobial activity of natural 2-benzoxazolinones and related derivatives J. Agric. Food Chem. 45 1997 3255 3257
4. C.A. Buchmann, A. Nersesyan, B. Kopp, D. Schauberger, F. Darroudi, T. Grummt, G. Krupitza, M. Kundi, R. Schulte-Hermann, and S. Knasmueller Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) and 2,4-dihydroxy-1,4- benzoxazin-3-one (DIBOA), two naturally occurring benzoxazinones contained in sprouts of Gramineae are potent aneugens in human-derived liver cells (HepG2) Cancer Lett. 246 2007 290 299
5. V. Cambier, T. Hance, and E. de Hoffmann Non-injured maize contains several 1,4-benzoxazin-3-one related compounds but only as glucoconjugates Phytochem. Anal. 10 1999 119 126
6. S.C. Carlsen, P. Kudsk, B. Laursen, S.K. Mathiassen, A.G. Mortensen, and I.S. Fomsgaard Allelochemicals in rye (Secale cereale L.): Cultivar and tissue differences in the production of benzoxazinoids and phenolic acids Nat. Prod. Commun. 4 2009 199 208
7. C.M. Chen, and M.T. Chen 6-Methoxybenzoxazolinone and triterpenoids from roots of Scoparia dulcis Phytochemistry 15 1976 1997 1999
8. S.M.F. Freire, J.A.S. Emim, A.J. Lapa, C. Souccar, and L.M.B. Torres Analgesic and antiinflammatory properties of Scoparia dulcis L. extracts and glutinol in rodents Phytother. Res. 7 1993 408 414
9. S.M. Freire, L.M. Torres, and C. Souccar Sympathomimetic effects of Scoparia dulcis L. and catecholamines isolated from plant extracts J. Pharm. Pharmacol. 48 1996 624 628
10. K. Hasegawa, S. Togo, M. Urashima, J. Mizutani, S. Kosemura, and S. Yamamura An auxin-inhibiting substance from light-grown maize shoots Phytochemistry 31 1992 3673 3676
11. T. Hayashi, K. Okamura, M. Kakemi, S. Asano, M. Mizutani, N. Takeguchi, M. Kawasaki, Y. Tezuka, T. Kikuchi, and N. Morita Scopadulcic acid B, a new tetracyclic diterpenoid from Scoparia dulcis L. Its structure, H+, K(+)-adenosine triphosphatase inhibitory activity and pharmacokinetic behaviour in rats Chem. Pharm. Bull. 38 1990 2740 2745
12. T. Hayashi, M. Kawasaki, Y. Miwa, T. Taga, and N. Morita Antiviral agents of plant origin. III. Scopadulin, a novel tetracyclic diterpene from Scoparia dulcis L Chem. Pharm. Bull. 38 1990 945 947
13. T. Hayashi, S. Asano, M. Mizutani, N. Takeguchi, T. Kojima, K. Okamura, and N. Morita Scopadulciol, an inhibitor of gastric H+, K(+)-ATPase from Scoparia dulcis, and its structure-activity relationships J. Nat. Prod. 54 1991 802 809
14. T. Hayashi, M. Kawasaki, K. Okamura, Y. Tamada, N. Morita, Y. Tezuka, T. Kikuchi, Y. Miwa, and T. Taga Scoparic acid A, a beta-glucuronidase inhibitor from Scoparia dulcis J. Nat. Prod. 55 1992 1748 1755
15. M. Kawasaki, T. Hayashi, M. Arisawa, N. Morita, and L.H. Berganza 8-Hydroxytricetin 7-glucuronide, a beta-glucuronidase inhibitor from Scoparia dulcis Phytochemistry 27 1988 3709 3711
16. M. Kluge, B. Schneider, and D. Sicker Diastereoselective synthesis of the benzoxazinone acetal glucoside ent-GDIMBOA: The first enentiomer of a natural acetal glucoside Carbohydr. Res. 298 1997 147 152
17. M. Latha, L. Pari, S. Sitasawad, and R. Bhonde Insulin-secretagogue activity and cytoprotective role of the traditional antidiabetic plant Scoparia dulcis (Sweet Broomweed) Life Sci. 75 2004 2003 2014
18. F.A. Macias, D. Marin, A. Oliveros-Bastidas, D. Chinchilla, A.M. Simonet, and J.M. Molinillo Isolation and synthesis of allelochemicals from Gramineae: Benzoxazinones and related compounds J. Agric. Food Chem. 54 2006 991 1000
19. S. Mesia-Vela, M. Bielavsky, L.M. Torres, S.M. Freire, M.T. Lima-Landman, C. Souccar, and A.J. Lapa In vivo inhibition of gastric acid secretion by the aqueous extract of Scoparia dulcis L. in rodents J. Ethnopharmacol. 111 2007 403 408
20. S. Murakami, M. Muramatsu, and S. Otomo Inhibition of gastric H+, K(+)-ATPase by quercetin J. Enzyme Inhib. 5 1992 293 298
21. S. Murakami, M. Muramatsu, and K. Tomisawa Inhibition of gastric H+, K(+)-ATPase by flavonoids: A structure-activity study J. Enzyme Inhib. 14 1999 151 166
22. T. Nakamura, E. Okuyama, A. Tsukada, M. Yamazaki, M. Satake, S. Nishibe, T. Deyama, A. Moriya, M. Maruno, and H. Nishimura Acteoside as the analgesic principle of cedron (Lippia triphylla), a Peruvian medicinal plant Chem. Pharm. Bull. 45 1997 499 504
23. C.M. Nath The new antidiabetic principle (amelin) occurring in nature. I. Studies on some of its biochemical properties Ann. Biochem. Exp. Med. 3 1943 55 62
24. H.M. Niemeyer Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the Gramineae Phytochemistry 27 1988 3349 3358
25. H.M. Niemeyer Hydroxamic acids derived from 2-hydroxy-2H-1,4-benzoxazin- 3(4H)-one: Key defense chemicals of cereals J. Agric. Food Chem. 57 2009 1677 1696
26. L. Pari, and S. Venkateswaran Hypoglycaemic activity of Scoparia dulcis L. extract in alloxan induced hyperglycaemic rats Phytother. Res. 16 2002 662 664
27. H.A. Pedersen, B. Laursen, A. Mortensen, and I.S. Fomsgaard Bread from common cereal cultivars contains an important array of neglected bioactive benzoxazinoids Food Chem. 127 2011 1814 1820
28. K.P. Roberts, R.A. Iyer, G. Prasad, L.T. Liu, R.E. Lind, and P.E. Hanna Cyclic hydroxamic acid inhibitors of prostate cancer cell growth: selectivity and structure activity relationships Prostate 34 1998 92 99
29. H. Sasai, M. Ishida, K. Murakami, N. Tadokoro, A. Ishihara, R. Nishida, and N. Mori Species-specific glucosylation of DIMBOA in larvae of the rice armyworm Biosci. Biotechnol. Biochem. 73 2009 1333 1338
30. Y. Shoyama, M. Matsumoto, and I. Nishioka Phenolic glycosides from diseased roots of Rehmannia glutinosa var. purpurea Phytochemistry 26 1987 983 986
31. A.I. Virtanen, and P.K. Hietala Precursors of benzoxazolinone in rye plants Acta. Chem. Scand. 14 1960 499 501
32. H. Wang, and T.B. Ng Hypotensive activity of the pineal indoleamine hormones melatonin, 5-methoxytryptophol and 5-methoxytryptamine Pharmacol. Toxicol. 86 2000 125 128
33. Q. Xiong, K. Hase, Y. Tezuka, T. Tani, T. Namba, and S. Kadota Hepatoprotective activity of phenylethanoids from Cistanche deserticola Planta Med. 64 1998 120 125
34. X. Zhang, F.K. Habib, M. Ross, U. Burger, A. Lewenstein, K. Rose, and J.C. Jaton Isolation and characterization of a cyclic hydroxamic acid from a pollen extract, which inhibits cancerous cell growth in vitro J. Med. Chem. 38 1995 735 738