Planta Med 2009; 75(11): 1241-1245
DOI: 10.1055/s-0029-1185506
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic and Antioxidative Phenolic Compounds from the Traditional Chinese Medicinal Plant, Myristica fragrans

Lin Duan1 [*] , Hong-Wen Tao1 [*] , Xiaojiang Hao2 , Qian-Qun Gu1 , Wei-Ming Zhu1
  • 1Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of , China, Qingdao, P. R. China
  • 2State Key Laboratory of Phytochemistry and Plant Resources, Kunming Institute of Botany, Chinese Academy of , Sciences, Kunming, P. R. China
Weitere Informationen

Publikationsverlauf

received August 14, 2008 revised February 13, 2009

accepted February 18, 2009

Publikationsdatum:
26. März 2009 (online)

Abstract

Two new phenolic compounds were isolated from the fruits of Myristica fragrans and their structures were elucidated as (−)-1-(2,6-dihydroxyphenyl)-9-[4-hydroxy-3-(p-menth-1-en-8-oxy)-phenyl]-1-nonanone (1) and (7R,8R)-7,8-dihydro-7-(3,4-dihydroxyphenyl)-3′-methoxy-8-methyl-1′-(E-propenyl)benzofuran (2). In addition, the absolute configuration of (+)-Δ8′-7-acetoxy-3,4,3′,5′-tetramethoxy-8-O-4′-neolignan (3) was determined for the first time through spectroscopic and chemical methods. Their antioxidative activities against 2,2-diphenyl-1-picrylhydrazyl radical and cytotoxicity against K-562 cells were tested, and (7S,8S,7′R,8′S)-4,5′-dihydroxy-3,3′-dimethoxy-7,7′-epoxylignan (4) showed the corresponding activities with IC50 values of 39.4 and 2.11 µM, respectively.

References

  • 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 U K, Kumar R S, Kumar T S. Antitumor activity and antioxident role of Bauhinia racemosa against Ehrlich ascites carcinoma in Swiss albino mice.  Acta Pharmacol Sin. 2004;  25 1070-1076
  • 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
  • 4 Proniuk S, Liederer B M, 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
  • 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 G F. 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
  • 9 Hattori M, Hada S, Watahiki A, Ihara H, Shu Y Z, 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
  • 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. New 2,5-bis-aryl-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 S A, 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 X F, She X G, Peng K, Su Y, Xie X G, Pan X F, Zhang H B. First enantioselective synthesis of the neolignans rhaphidecursinol A and virolongin B.  J Chin Chem Soc. 2004;  51 969-974
  • 17 Gonzales A G, Barrera J B, Arancibia L, Diaz J G, Paz P P. 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 J P, Yang X L, Liu Z L. Diarylheptanoids from the rhizomes of Zingiber officinale.  Phytochemistry. 2004;  65 1137-1143
  • 20 Peng K, Chen F X, She X G, Yang C H, Cui Y X, Pan X F. Selective oxidation of benzylic or allylic hydroxyl group of sec-1,2-diols.  Tetrahedron Lett. 2005;  46 1217-1220
  • 21 Kumar N S, Herath H MTB, Karunaratne V. Arylalkanones from Myristica dactyloides.  Phytochemistry. 1988;  27 465-468
  • 22 Pham V C, Jossang A, Sevenet T, Bodo B. Cytotoxic acylphenols from Myristica maingayi.  Tetrahedron. 2000;  56 1707-1713
  • 23 Purushothaman K K, Sarada A, Connolly J D. Malabaricones A–D, novel diarylnonanoids from Myristica malabarica Lam (Myristicaceae).  J Chem Soc [Perkin I]. 1977;  587-588
  • 24 Mosmann T J. 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 R T, Ho C T. 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 J S. 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 I R, Lopes L MX, Davin L B, Lewis N G. Stereoselective synthesis of 8,9-licarinediols.  Tetrahedron. 2000;  56 9181-9193
  • 29 Herrera Braga A C, 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

1 These authors equally contributed to this paper.

Prof. Dr. Wei-Ming Zhu

School of Medicine and Pharmacy
Ocean University of China

5# Yushan Road

Qingdao 266003

People's Republic of China

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Fax: + 86 5 32 82 03 12 68

eMail: weimingzhu@ouc.edu.cn