Antiproliferative, Anti-Aromatase, Anti-17β-HSD and Antioxidant Activities of Lignans Isolated from Myristica argentea

Abstract

Four lignans were isolated from the petrol extract of Myristica argentea mace (Myristicaceae) and their structures were elucidated by means of NMR and mass spectrometry. Although they have been previously described, NMR data are only available for threo-austrobailignan-5, which has been isolated only once, and is incomplete. Three of them, erythro-austrobailignan-6, meso-dihydroguaiaretic acid and nectandrin-B, exert an antiproliferative effect on MCF-7 cells as well as antioxidant activity on the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, but not the threo-austrobailignan-5. Nectandrin-B also possesses anti-17β-hydroxysteroid dehydrogenase and anti-aromatase activities.

Key words

Myristica argentea - Myristicaceae - lignans - antiproliferative activity - antioxidant activity - anti-17β-HSD activity - anti-aromatase activity

References

• 1 Philcox D. Revised handbook to the flora of Ceylon. Amerind Publishing and Co. Ltd New Delhi; 1996 Vol XI
• 2 Massanet G M, Pando E, Rodriguez-Luis F, Zubia E. Lignans: a review.  Fitoterapia. 1989;  60 3-35
• 3 Ward G M. Lignans, neolignans and related compounds.  Natural Product Report. 1993;  10 1-28
• 4 Adlercreutz H. Phytoestrogens: Epidemiology and possible role in cancer protection. Environ.  Health Perspect.. 1995;  103 103-12
• 5 Moss G P. IUPAC-IUB.  Joint Commission on Biochemical Nomenclature. 1989;  25 - 2 1
• 6 Nakatani N, Ikeka K. Structure of lignans from Papuan Mace (Myristica argentea Warb.)  Chemistry Express. 1987;  2 627-30
• 7 Purushothaman K K, Sarada A. Structure of malabaricanol. A lignan from the aril of Myristica malabarica Lam.  Indian Journal of Chemistry . 1984;  23 B 46-8
• 8 Essig-Marcello J S, Van-Buskirk R G. A double label in situ cytotoxicity assay using the fluorescent probes neutral red and BCECF-AM.  Vitro Toxicology. 1990;  3 219-23
• 9 Rat P. New micotritaton fluorometric technology - Applications to dermotoxicity. Nouv.  Dermatol.. 1993;  12 471-6
• 10 Le Bail J C, Laroche T, Marre-Fournier F, Habrioux G. Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids.  Cancer Letters. 1998;  133 101-6
• 11 Le Bail J C, Champavier Y, Chulia A -J, Habrioux G. Effects of phytoestrogens on aromatase, 3β- and 17β-hydroxysteroid dehydrogenase activities and human breast cancer cells.  Life Sciences. 2000;  66 1281-91
• 12 Varache-Beranger M, Nuhrich A, Amiell J, Dufour P, Devaux G. Synthesis and anti-inflammatory activity of (3,5-di-tert-butyl-4-hydroxybenzilidene) cyclanones and related compounds.  European Journal of Medicinal Chemistry. 1991;  26 551-6
• 13 Uchida S, Edamatsu R, Hiramatsu M, Mori A, Nonaka G, Nishioka I. et al . Condensed tannins scavenge active oxygen free radical.  Medicine Science Research. 1987;  15 831-2
• 14 Hattori M, Hada S, Kawata Y, Tezuka Y, Kikuchi T, Namba T. New 2,5-bis-aryl-3,4-dimethyltetrahydrofuran lignans from the aril of Myristica fragrans, Chem. Pharm.  Bull.. 1987;  35 3315-22
• 15 Murphy S T, Ritchie E, Taylor W C. Some constituents of Austrobaileya scandens (Austrobaileyaceae): Structures of seven new lignans.  Aust. J. Chem.. 1975;  28 81-90
• 16 Mc Rae W D, Towers G HN. Biological activities of lignans.  Phytochemistry. 1984;  26 1207-20
• 17 Charlton J L. Antiviral activity of lignans.  J. Nat Prod.. 1998;  61 1447-51
• 18 Gnabre J, Huang R CC, Bates R B, Burns J J, Caldera S, Malcomson M E. et al . Characterization of anti-HIV lignans from Larrea tridentata .  Tetrahedron. 1995;  51 12 203-10
• 19 Ghisalberti E L. Cardiovascular activity of naturally occurring lignans.  Phytomedicine. 1997;  4 151-6