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. 2016 Dec;15(6):1035-1056.
doi: 10.1007/s11101-016-9469-x. Epub 2016 May 10.

Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.)

Ehab A Abourashed  1 , Abir T El-Alfy  1
Affiliations

Chemical diversity and pharmacological significance of the secondary metabolites of nutmeg (Myristica fragrans Houtt.)

Ehab A Abourashed et al. Phytochem Rev. 2016 Dec.

Abstract

Nutmeg is a valued kitchen spice that has been used for centuries all over the world. In addition to its use in flavoring foods and beverages, nutmeg has been used in traditional remedies for stomach and kidney disorders. The antioxidant, antimicrobial and central nervous system effects of nutmeg have also been reported in literature. Nutmeg is a rich source of fixed and essential oil, triterpenes, and various types of phenolic compounds. Many of the secondary metabolites of nutmeg exhibit biological activities that may support its use in traditional medicine. This article provides an overview of the chemistry of secondary metabolites isolated from nutmeg kernel and mace including common methods for analysis of extracts and pure compounds as well as recent approaches towards total synthesis of some of the major constituents. A summary of the most significant pharmacological investigations of potential drug leads isolated from nutmeg and reported in the last decade is also included.

Keywords: Biological evaluation; Chromatographic analysis; Diarylalkanes; Lignans/neolignans; Nutmeg; Phenylpropanoids; Terpenes.

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Conflict of interest statement

The authors state no conflict of interest and have received no payment for the preparation of this manuscript.

Figures

Figure 1
Figure 1
Geographical locations and morphological structure of nutmeg*. (A) East Indies (Maluku islands circled); (B) West Indies (Grenada islands circled); (C) nutmeg fruit, seed kernel (1) and arillus (2). *(West Indies tree droppings)
Figure 2
Figure 2
Significant monoterpenes and phenylpropanoids of nutmeg essential oil
Figure 3
Figure 3
Phenylpropanoid coupling patterns leading to formation of lignans and neolignans. *have not been reported in nutmeg
Figure 4
Figure 4
Lignan secondary metabolites identified in M. fragrans and other species of Myristica
Figure 5
Figure 5
A. Benzofuranoid neolignans of nutmeg B. Non-benzofuranoid (8.O.4’) neolignans (8,4’-oxyneolignans) of nutmeg
Figure 5
Figure 5
A. Benzofuranoid neolignans of nutmeg B. Non-benzofuranoid (8.O.4’) neolignans (8,4’-oxyneolignans) of nutmeg
Figure 6
Figure 6
Diphenylalkanes isolated from Myristica fragrans
Figure 7
Figure 7
Phenylpropanediols, steroids and alkylcyclobutanone secondary metabolites detected in nutmeg kernel
Figure 8
Figure 8
Rat metabolism of licarin A (35)(Li and Yang 2011)
Figure 9
Figure 9
Total synthesis of the lignan dihydroguaiaretic acid (30)(Kawaguchi et al. 2009)
Figure 10
Figure 10
Total synthesis of selected neolignans. A. Licarin B (37) (Engler and Chai 1996); B. Surinamensin (50) (Zacchino and Badano 1985)
Figure 11
Figure 11
Total synthesis of malabaricone B (59) (Hosoi et al. 1999, Tsuda et al. 1991)
See this image and copyright information in PMC

References

    1. Abourashed EA, Khan IA. Nutmeg. In: Khan IA, Abourashed EA, editors. Leung's Encyclopedia of Common Natural Ingredients Used in Food, Drugs and Cosmetics. 3rd. Hoboken, NJ: Wiley; 2010. pp. 467–470.
    1. Aiba CJ, Gottlieb OR, Pagliosa FM, Yoshida M, Magalhaes MT. Neolignans from Nectandra miranda. Phytochemsitry. 1977;16:745–748.
    1. Akinboro A, Mohamed KB, Asmawi MZ, Sulaiman SF, Sofiman OA. Antioxidants in aqueous extract of Myristica fragrans (Houtt.) suppress mitosis and cyclophosphamide-induced chromosomal aberrations in Allium cepa L. cells. J Zhejiang Univ Sci B. 2011;12:915–922. - PMC - PubMed
    1. Antonio RL, Kozasa EH, Galduroz JC, Dawa, Dorjee Y, Kalsang T, Norbu T, Tenzin T, Rodrigues E. Formulas used by Tibetan doctors at Men-Tsee-Khang in India for the treatment of neuropsychiatric disorders and their correlation with pharmacological data. Phytother Res. 2013;27:552–563. - PubMed
    1. Asgarpanah J, Kazemivash N. Phytochemistry and pharmacologic properties of Myristica fragrans Houtt.: A review. Afr J Biotechnol. 2012;11:12787–12793.