Article

Chemical Constituents of the Fruits of Morinda citrifolia (Noni) and Their Antioxidant Activity

Division of Medicinal Chemistry and Pharmacognosy, The Ohio State University, Columbus, Ohio, United States
Journal of Natural Products (Impact Factor: 3.8). 05/2005; 68(4):592-5. DOI: 10.1021/np0495985
Source: PubMed

ABSTRACT

Purification of a n-BuOH-soluble partition of the MeOH extract of Morinda citrifolia (Noni) fruits led to the isolation of two new iridoid glucosides, 6alpha-hydroxyadoxoside (1) and 6beta,7beta-epoxy-8-epi-splendoside (2), as well as 17 known compounds, americanin A (3), narcissoside (4), asperuloside, asperulosidic acid, borreriagenin, citrifolinin B epimer a, citrifolinin B epimer b, cytidine, deacetylasperuloside, dehydromethoxygaertneroside, epi-dihydrocornin, d-glucose, d-mannitol, methyl alpha-d-fructofuranoside, methyl beta-d-fructofuranoside, nicotifloroside, and beta-sitosterol 3-O-beta-d-glucopyranoside. The structures of the new compounds were determined by spectroscopic data interpretation. Compound 4, borreriagenin, cytidine, deacetylasperuloside, dehydromethoxygaertneroside, epi-dihydrocornin, methyl alpha-d-fructofuranoside, and methyl beta-d-fructofuranoside were isolated for the first time from M. citrifolia. The antioxidant activity was evaluated for all isolates in terms of both DPPH and ONOO(-) bioassays. The neolignan, americanin A (3), was found to be a potent antioxidant in these assays.

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    • "Earlier reports indicated that fruits (Millonig et al., 2005; Stadlbauer et al., 2005; Yüce et al., 2006), leaves (West et al., 2006; Lopez-Cepero et al., 2007) and juice (Sivagnanam et al., 2011; Mrzljak et al., 2013) of M. citrifolia are hepatotoxic in humans, since preparations for them are rich inanthraquinones and coumarins (scopoletin) (Ee et al., 2009), they induce generation of free radicals derived from oxygen and trigger oxidative stress. Free radicals cause depletion of intracellular reduced glutathione and mitochondrial membrane potential, thus initiating lipid peroxidation and eventually, cell death (Su et al., 2005; Bussmann et al., 2013). Herein, using biochemistry and morphological analysis, it was shown that the AEMC at 2.5, 5 and 10 mg/kg induced hepatotoxicity in rats, as confirmed by levels of AST, ALT, ALP and GGT (this latter only at 10 mg/kg). "

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    • "C. The data was consistent with the previously published data (Su et al., 2005). "
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    • "Mahattanadul et al. (2011) showed that pure scopoletin has similar antisecretory and antiulcer properties to that of an aqueous extract of Noni, but lower prokinetic activity. Neolignan, americanin A, 3,3 0 -bisdemethyl pinoresinol, morindolin, and isoprincepin were shown to be potent antioxidant compounds in an assay based on copper-induced oxidation of low-density lipoprotein (Kamiya et al., 2004; Su et al., 2005). Noni fruit is reported to contain a novel component, proxeronine, a precursor of the alkaloid xeronine , as well as proxeronase, which have been shown to have a wide range of biological activities, such as cell strengthening and revitalizing activities (Logsdon, 2009). "
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