Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.
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.
Su
Bao-Ning
BN
Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Pawlus
Alison D
AD
Jung
Hyun-Ah
HA
Keller
William J
WJ
McLaughlin
Jerry L
JL
Kinghorn
A Douglas
AD
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds; D000081004:Cyclopentane Monoterpenes; D004147:Dioxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D039823:Iridoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D032066:Morinda / Q000737:chemistry*; D010851:Picrates / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
C501041:6alpha-hydroxyadoxoside; C501042:6beta,7beta-epoxy-8-epi-splendoside; D000975:Antioxidants; D001713:Biphenyl Compounds; D000081004:Cyclopentane Monoterpenes; D004147:Dioxins; D005960:Glucosides; D039823:Iridoids; D010851:Picrates; D011714:Pyrans; C055021:americanin A; C004931:1,1-diphenyl-2-picrylhydrazyl; C077956:asperuloside