Two new coumarins from Micromelum falcatum with cytotoxicity and brine shrimp larvae toxicity

Molecules

Volumn 17, Issue 6, 2012, Pages 6944-6952

  Luo, Xiongming ^a   He, Weihong ^a   Yin, Hao ^a   Li, Qingxin ^a   Liu, Qiao ^a   Huang, Yongzhong ^a   Zhang, Si ^a  

^a SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY   (China)

Author keywords

Antibacterial activity; Brine shrimp larvae toxicity; Coumarins; Cytotoxicity; Micromelum falcatum

Indexed keywords

7 METHOXY 8 (1 HYDROXY 2 O BETA GLUCOPYRANOSYL 3 METHYL 4 BUTENE 1 YL)COUMARIN; 7 METHOXY 8 (2 HYDROXMETHYL 1 O ISOVALERYL 4 BUTENYL) COUMARIN; 7-METHOXY-8-(1-HYDROXY-2-O-BETA-GLUCOPYRANOSYL-3-METHYL-4-BUTENE-1-YL)COUMARIN; 7-METHOXY-8-(2-HYDROXMETHYL-1-O-ISOVALERYL-4-BUTENYL)-COUMARIN; COUMARIN DERIVATIVE; PLANT EXTRACT;

ANIMAL; ARTEMIA; ARTICLE; CHEMISTRY; DRUG EFFECT; HUMAN; IC 50; LARVA; LD 50; PLANT STEM; RUTACEAE; TUMOR CELL LINE;

ANIMALS; ARTEMIA; CELL LINE, TUMOR; COUMARINS; HUMANS; INHIBITORY CONCENTRATION 50; LARVA; LETHAL DOSE 50; PLANT EXTRACTS; PLANT STEMS; RUTACEAE;

EID: 84862986475     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17066944     Document Type: Article

References (21)

1. Roy, M. K.; Thalang, V. N.; Trakoontivakorn, G.; Nakahara, K. Mahanine, a carbazole alkaloid from micromelum minutum, inhibits cell growth and induces apoptosis in u937 cells through a mitochondrial dependent pathway. Br. J. Pharmacol. 2005, 145, 145-155. (Pubitemid 40756519)
2. Ma, C. Y.; Case, R. J.; Wang, Y. H.; Zhang, H. J.; Tan, G. T.; Van Hung, N.; Cuong, N. M.; Franzblau, S. G.; Soejarto, D. D.; Fong, H. H. S. Anti-tuberculosis constituents from the stem bark of micromelum hirsutum. Planta Med. 2005, 71, 261-267. (Pubitemid 40476784)
3. Sohrab, M. H.; Chowdhury, R.; Hasan, C. M.; Rashid, M. A. Chemotaxonomic significance of polyoxygenated flavonoids from the leaves of micromelum minutum. Biochem. Syst. Ecol. 2004, 32, 829-831. (Pubitemid 38946537)
4. Nakahara, K.; Trakoontivakorn, G.; Alzoreky, N. S.; Ono, H.; Onishi-Kameyama, M.; Yoshida, M. Antimutagenicity of some edible thai plants, and a bioactive carbazole alkaloid, mahanine, isolated from micromelum minutum. J. Agric. Food Chem. 2002, 50, 4796-4802. (Pubitemid 34856147)
5. Kong, Y. C.; But, P. P. H.; Ng, K. H.; Li, Q.; Cheng, K. F.; Waterman, P. G. Micromelum-a key genus in the chemosystematics of the clauseneae. Biochem. Syst. Ecol. 1988, 16, 485-489.
6. Kamperdick, C.; Phuong, N. M.; Sung, T. V.; Schmidt, J.; Adam, G. Coumarins and dihydrocinnamic acid derivatives from micromelum falcatum. Phytochemistry 1999, 52, 1671-1676. (Pubitemid 30019628)
7. Luo, X. M.; Qi, S. H.; Yin, H.; Gao, C. H.; Zhang, S. Alkaloids from the stem bark of micromelum falcatum. Chem. Pharm. Bull. 2009, 57, 600-602.
8. Luo, X.; Qi, S.; Yin, H.; Xiao, Z.; Zhang, S. Micromelosides a-d, four new coumarins from the stem bark of micromelum falcatum. Magn. Reson. Chem. 2009, 47, 1110-1114.
9. Cassady, J. M.; Ojima, N.; Chang, C. J.; McLaughlin, J. L. Potential anti-tumor agents. 11. Investigation of the anti-tumor activity of micromelum-integerrimum (rutaceae). J. Nat. Prod. 1979, 42, 274-278.
10. Ito, C.; Itoigawa, M.; Furukawa, H.; Tokuda, H.; Okuda, Y.; Mukainaka, T.; Okuda, M.; Nishino, H. Anti-tumor-promoting effects of 8-substituted 7-methoxycoumarins on epstein-barr virus activation assay. Cancer Lett. 1999, 138, 87-92. (Pubitemid 29189189)
11. Tantivatana, P.; Ruangrungsi, N.; Vaisiriroj, V.; Lankin, D. C.; Bhacca, N. S.; Borris, R. P.; Cordell, G. A.; Johnson, L. F. Microminutin, a novel cyto-toxic coumarin from micromelum minutum (rutaceae). J. Org. Chem. 1983, 48, 268-270. (Pubitemid 13135832)
12. Talapatra, S. K.; Mukhopadhyay, S. K.; Talapatra, B. Minor coumarins of boenninghausenia albiflora. Phytochemistry 1975, 14, 836-837.
13. Allison, S.; Burks, S. J.; Taylor, R. T. Total syntheses of microminutin and other coumarins through the key intermediate isomurralonginol. Tetrahedron 1991, 47, 9737-9742.
14. Lin, J. K.; Wu, T. S. Constituents of flowers of murraya paniculata. J. Chin. Chem. Soc. 1994, 41, 213-216.
15. Wu, T. S.; Liou, M. J.; Jong, T. T.; Chen, Y. J.; Lai, J. S. Indole alkaloids and coumarins from the root bark of murraya paniculata var omphalocarpa. Phytochemistry 1989, 28, 2873-2874.
16. Gu, J. Q.; Graf, T. N.; Lee, D. H.; Chai, H. B.; Mi, Q. W.; Kardono, L. B. S.; Setyowati, F. M.; Ismail, R.; Riswan, S.; Farnsworth, N. R. Cytotoxic and antimicrobial constituents of the bark of diospyros maritima collected in two geographical locations in indonesia. J. Nat. Prod. 2004, 67, 1156-1161. (Pubitemid 38971678)
17. Imai, F.; Kinoshita, T.; Itai, A.; Sankawa, U. Acid-catalyzed rearrangement of an epoxy coumarin phebalosin the revised structure of murralongin. Chem. Pharm. Bull. 1986, 34, 3978-3981. (Pubitemid 17192789)
18. Ito, C.; Furukawa, H. Constituents of murraya exotica l structure elucidation of new coumarins. Chem. Pharm. Bull. 1987, 35, 4277-4285.
19. Rahmani, M.; Taufiqyap, Y. H.; Ismail, H. B. M.; Sukari, A.; Waterman, P. G. New coumarin and dihydrocinnamic acid-derivatives from 2 malaysian populations of micromelum minutum. Phytochemistry 1994, 37, 561-564. (Pubitemid 2149383)
20. Wanyoike, G. N.; Chhabra, S. C.; Lang'at-Thoruwa, C. C.; Omar, S. A. Brine shrimp toxicity and antiplasmodial activity of five kenyan medicinal plants. J. Ethnopharmacol. 2004, 90, 129-133. (Pubitemid 38091697)
21. Shen, A. Y.; Chen, C. P.; Roffler, S. A chelating agent possessing cytotoxicity and antimicrobial activity:7-morpholinomethyl-8-hydroxyquinoline. Life Sci. 1999, 64, 813-825. (Pubitemid 29098976)