Acylphenols from Myristica crassa as New Acetylcholinesterase Inhibitors

 

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Abstract

A significant acetylcholinesterase inhibitory activity was observed for the ethyl acetate and methanol extracts from the leaves and the fruits of Myristica crassa. Three new dimeric acylphenols, giganteone C (5), maingayones B and C (6 and 7) were isolated together with the known malabaricones B and C (2 and 3) and giganteone A (4). Compounds 2 and 3 possess significant inhibitory activity on acetylcholinesterase. LC/MS study was particularly useful to discriminate structures of compounds 6 and 7.

References

• 1 Whitmore T C. Myristicaceae. In: Whitmore TC, editor Tree flora of Malaya; A manual for foresters, volume 1. HongKong; Longman 1972: 315-45
  Google Scholar
• 2 Jayaweera D MA. Medicinal plants used in Sri Lanka; Part IV. Colombo; National Science Council 1982: 1-107
  Google Scholar
• 3 Purushothaman K K, Sarada A, Connolly J D. Malabaricones A – D, novel diarylnonanoids from Myristica malabarica Lam (Myristicaceae). J Chem Soc [Perkin I] 1977: 587-8
  Google Scholar
• 4 Cooray N F, Jansz E R, Wimalasena S, Wueselkera T P, Nair B M. Acylresorcinols from seed kernels of Myristica dactyloides.  Phytochemistry. 1987;  26 3369-71
  CrossrefPubMedGoogle Scholar
• 5 Orabi K Y, Mossa J S, El-Feraly F S. Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans).  J Nat Prod. 1991;  54 856-9
  CrossrefPubMedGoogle Scholar
• 6 Van Cuong P, Jossang A, Sévenet T, Bodo B. Cytotoxic acylphenols from Myristica maingayi.  Tetrahedron. 2000;  56 1707-13
  CrossrefPubMedGoogle Scholar
• 7 Van Cuong P, Jossang A, Sévenet T, Bodo B. Novel cytotoxic acylphenol dimers of Myristica gigantea; enzymatic synthesis of giganteones A and B.  Tetrahedron. 2002;  58 5709-14
  CrossrefPubMedGoogle Scholar
• 8 Hosoi S, Kiuchi F, Nakamura N, Imasho M, Ahad Ali M, Sasaki Y. et al . Synthesis and nematocidal activity of diarylnonanoids related to malabaricones.  Chem Pharm Bull. 1999;  47 37-43
  PubMedGoogle Scholar
• 9 Rupashree S, Ajay B K, Subrata C, Mitali C. Antipromastigote activity of the malabaricones of Myristica malabarica (rampatri).  Phytother Res. 2007;  21 592-5
  CrossrefPubMedGoogle Scholar
• 10 Debashish B, Ajay B K, Ranjit G K, Sandip B K, Subrata C. Healing properties of malabaricone B and malabaricone C, against indomethacin-induced gastric ulceration and mechanism of action.  Eur J Pharmacol. 2008;  578 300-12
  CrossrefPubMedGoogle Scholar
• 11 Mukherjee P K, Kumar V, Houghton P. Screening of Indian medicinal plants for acetylcholinesterase activity.  Phytother Res. 2007;  21 1142-5
  CrossrefPubMedGoogle Scholar
• 12 Dhingra D, Parle M, Kulkarni S K. Comparative brain cholinesterase-inhibiting activity of Glycyrrhiza glabra, Myristica fragrans, ascorbic acid, and metrifonate in mice.  J Med Food. 2007;  9 281-3
  PubMedGoogle Scholar
• 13 Ellman G L, Courtney K D, Andres V, Featherstone R MA. New and rapid colorimetric determination of acetylcholinesterase activity.  Biochem Pharmacol. 1961;  7 88-95
  CrossrefPubMedGoogle Scholar
• 14 Bousserouel H, Litaudon M, Morleo B, Martin M -T, Thoison O, Nosjean O. et al . New biologically active linear triterpenes from the bark of three new-caledonian Cupaniopsis species.  Tetrahedron. 2005;  61 845-51
  CrossrefPubMedGoogle Scholar
• 15 Mukherjee P K, Kumar V, Mal M, Houghton P J. Acetycholinesterase inhibitors from plants.  Phytomedicine. 2007;  14 289-300
  CrossrefPubMedGoogle Scholar

Dr. Marc Litaudon

Institut de Chimie des Substances Naturelles

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