Cytotoxic and antioxidative phenolic compounds from the traditional chinese medicinal plant, myristica fragrans

Planta Medica

Volumn 75, Issue 11, 2009, Pages 1241-1245

  Duan, Lin ^a   Tao, Hong Wen ^a   Hao, Xiao Jiang ^b   Gu, Qian Qun ^a   Zhu, Wei Ming ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b KUNMING INSTITUTE OF BOTANY   (China)

Author keywords

Antioxidative activity; Cytotoxicity; Myristica fragrans; Myristicaceae; Phenylpropanoids

Indexed keywords

1 (2,6 DIHYDROXYPHENYL) 9 (3,4 DIHYDROXYPHENYL) 1 NONANONE; 1 (2,6 DIHYDROXYPHENYL) 9 (4 HYDROXYPHENYL) 1 NONANONE; 1 (2,6 DIHYDROXYPHENYL) 9 [4 HYDROXY 3 (4 MENTH 1 EN 8 OXY)PHENYL] 1 NONANONE; 1 (4 HYDROXY 3 METHOXYPHENYL) 1,2 PROPANEDIOL; 1,1 DIPHENYL 2 PICRYLHYDRAZYL; 3 (3,4 METHOXY 3,4 METHYLENEDIOXYPHENYL) 1,2 PROPANEDIOL; 3 (3,4,5 TRIMETHOXYPHENYL) 1,2 PROPANEDIOL; 3 (5 METHOXY 3,4 METHYLENEDIOXYPHENYL) 1,2 PROPANEDIOL; 4,5' DIHYDROXY 3,3' DIMETHOXY 7,7' EPOXYLIGNAN; 7,8 DIHYDRO 7 (3,4 DIHYDROXYPHENYL) 3' METHOXY 8 METHYL 1' (E PROPENYL)BENZOFURAN; ANTINEOPLASTIC AGENT; ANTIOXIDANT; DELTA8' 7 ACETOXY 3,4,3',5' TETRAMETHOXY 8 O 4' NEOLIGNAN; ERYTHRO DELTA8' 4,7 DIHYDROXY 3,3',5' TRIMETHOXY 8 O 4' NEOLIGNAN 8' ENE; ERYTHRO DELTA8' 7 DIHYDROXY 3,4,5,3',5' PENTAMETHOXY 8 O 4' NEOLIGNAN 8' ENE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHINESE MEDICINE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; MEDICINAL PLANT; NONHUMAN; NUTMEG; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTIOXIDANTS; CELL LINE, TUMOR; CYTOTOXINS; DRUGS, CHINESE HERBAL; HUMANS; MYRISTICA FRAGRANS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHENOLS;

MYRISTICA FRAGRANS; MYRISTICACEAE;

EID: 70350782381     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0029-1185506     Document Type: Article

References (30)

1. Waris G, Ahsan H. Reactive oxygen species: role in the development of cancer and various chronic conditions. Carcinogenesis 2006; 5: 14
2. Gupta M, Mazumder UK, Kumar RS, Kumar TS. Antitumor activity and antioxident role of Bauhinia racemosa against Ehrlich ascites carcinoma in Swiss albino mice. Acta Pharmacol Sin 2004; 25: 1070-1076 (Pubitemid 39071116)
3. Hirose M, Takahashi S, Ogawa K, Futakuchi M, Shirai T. Phenolics: blocking agents for heterocyclic amine-induced carcinogenesis. Food Chem Toxicol 1999; 37: 985-992 (Pubitemid 29481802)
4. Proniuk S, Liederer BM, Blanchard J. Preformulation study of epigallocatechin gallate, a promising antioxidant for topical skin cancer prevention. J Pharm Sci 2002; 91: 111-116
5. Amarowicz R, Naczk M, Shahidi F. Antioxidant activity of various fractions of non-tanin phenolics of canola hulls. J Agric Food Chem 2000; 48: 2755-2759 (Pubitemid 30490483)
6. Jiangshu New College of Medicine. Zhongyao dacidian (a dictionary of traditional Chinese medicine). Shanghai: Shanghai Science and Technology Publishing House; 1977: 894-895
7. He GF. Natural antioxidants from Myristica fragrans Houtt. Food Sci 1986; 12: 43-44
8. Nakamura N, Kiuchi F, Tsuda Y, Kondo K. Studies on crude drugs effective on visceral larva migrans. V: the larvicidal principle in mace (aril of Myristica fragrans). Chem Pharm Bull 1988; 36: 2685-2688 (Pubitemid 18198178)
9. Hattori M, Hada S, Watahiki A, Ihara H, Shu YZ, Kakiuchi N, Mizuno T, Namba T. Studies on dental caries prevention by traditional medicines. X: antibacterial action of phenolic components from mace against Streptococcus mutans. Chem Pharm Bull 1986; 34: 3885-3893 (Pubitemid 17192778)
10. Morita T, Jinno K, Kawagishi H, Arimoto Y, Suganuma H, Inakuma T, Sugiyama K. Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/D-galactosamine-induced liver injury. J Agric Food Chem 2003; 51: 1560-1565
11. Isogai A, Murakoshi S, Suzuki A, Tamura S. Structures of new dimeric phenylpropanoids from Myristica fragrans. Agric Biol Chem 1973; 37: 1479-1486
12. Hattori M, Hada S, Kawata Y, Tezuka Y, Kikuchi T, Namba T. New2,5-bisaryl-3,4-dimethyl tetrahydrofuran lignans from the aril of Myristica fragrans. Chem Pharm Bull 1987; 35: 3315-3322
13. Kasahara H, Miyazawa M, Kameoka H. Biotransformation of an acyclic neolignan in rats. Phytochemistry 1995; 38: 343-346
14. Kasahara H, Miyazawa M, Kameoka H. Absolute configuration of 8-O-4′-neoligans from Myristica fragrans. Phytochemistry 1995; 40: 1515-1517
15. Zacchino SA, Badano H. Enantioselective synthesis and absolute configuration assignment of erythro-(3,4,5-trimethoxy-7-hydroxy-1′-allyl- 2′,6′-dimethoxy)-8.O.4′-neolignan, isolated from mace (Myristica fragans). J Nat Prod 1988; 51: 1261-1265
16. Ren XF, She XG, Peng K, Su Y, Xie XG, Pan XF, Zhang HB. First enantioselective synthesis of the neolignans rhaphidecursinol A and virolongin B. J Chin Chem Soc 2004; 51: 969-974
17. Gonzales AG, Barrera JB, Arancibia L, Diaz JG, Paz PP. Two phenylpropanoids from Todaroa aurea subsp. suaveolens. Phytochemistry 1991; 30: 4189-4190
18. Rukachaisirikur T, Intaraudom J, Chawanasak S, Suksamram A. Phenylpropanoids from Cinnamomum parthenoxylon. Sci Asia 2000; 26: 159-161
19. Ma JP, Yang XL, Liu ZL. Diarylheptanoids from the rhizomes of Zingiber officinale. Phytochemistry 2004; 65: 1137-1143
20. Peng K, Chen FX, She XG, Yang CH, Cui YX, Pan XF. Selective oxidation of benzylic or allylic hydroxyl group of sec-1,2-diols. Tetrahedron Lett 2005; 46: 1217-1220
21. Kumar NS, Herath HMTB, Karunaratne V. Arylalkanones from Myristica dactyloides. Phytochemistry 1988; 27: 465-468
22. Pham VC, Jossang A, Sevenet T, Bodo B. Cytotoxic acylphenols from Myristica maingayi. Tetrahedron 2000; 56: 1707-1713
23. Purushothaman KK, Sarada A, Connolly JD. Malabaricones A-D, novel diarylnonanoids from Myristica malabarica Lam (Myristicaceae). J Chem Soc [Perkin I] 1977: 587-588
24. Mosmann TJ. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 65: 55-63
25. Chen Y, Wong M, Rosen RT, Ho CT. 2,2-Diphenyl-1-picrylhydrazyl radical-scavenging active components from Polygonum multiflorum. J Agric Food Chem 1999; 47: 2226-2228
26. Ito K, Ichino K, Iida T, Lai JS. Neolignans from Magnolia kachirachirai. Phytochemistry 1984; 23: 2643-2645
27. Antus S, Kurtan T, Juhasz L, Kiss L, Hollosi M, Majer Z. Chiroptical properties of 2,3-dihydrobenzo[b]furan and chromane chromophores in naturally occurring O-heterocycles. Chirality 2001; 13: 493-506
28. Nascimento IR, Lopes LMX, Davin LB, Lewis NG. Stereoselective synthesis of 8,9-licarinediols. Tetrahedron 2000; 56: 9181-9193
29. Herrera Braga AC, Zacchino S, Badano H, González Sierra M, Rúveda E. 13C NMR spectral and conformational analysis of 8-O-4′-neolignans. Phytochemistry 1984; 23: 2025-2028
30. Konya K, Kurtan T, Kiss-Szikszai A, Juhasz L, Antus S. A general CD-method for the configurational assignment of erythro-8.4′-oxyneolign- 8′-enes. ARKIVOC 2004; 13: 72-78