Noniosides E - H, New Trisaccharide Fatty Acid Esters from the Fruit of Morinda citrifolia (Noni)

Abstract

Four new trisaccharide fatty acid esters named noniosides E - H (4 - 7) were isolated from the fruit of Morinda citrifolia (Noni) by a combination of Sephadex LH-20, high-speed countercurrent chromatography (HSCCC) and semipreparative HPLC. Their structures were elucidated by high resolution mass spectrometry and 1D- and 2D-NMR as 2,6-di-O-(β-D-glucopyranosyl)-1-O-hexanoyl-β-D-glucopyranose (4), 2,6-di-O-(β-D-glucopyranosyl)-1-O-decanoyl-β-D-glucopyranose (5), 2-O-(6-O-octanoyl-β-D-glucopyranosyl)-6-O-(β-D-glucopyranosyl)-1-O-octanoyl-β-D-glucopyranose (6), and 2-O-(6-O-hexanoyl-β-D-glucopyranosyl)-6-O-(β-D-glucopyranosyl)-1-O-octanoyl-β-D-glucopyranose or 2-O-(6-O-octanoyl-β-D-glucopyranosyl)-6-O-(β-D-glucopyranosyl)-1-O-hexanoyl-β-D-glucopyranose (7), respectively. In addition, an HPLC-MS analysis of a methanolic extract of the fruit powder revealed the presence of further derivatives including new disaccharide and trisaccharide esters with fatty acid residues of various lengths.

Morinda citrifolia - Rubiaceae - trisaccharide fatty acid esters - fatty acid glucosides - fatty alcohol glucosides - noniosides - HSCCC - novel food

References

• 1 Levand O, Larson H O. Some chemical constituents of Morinda citrifolia .  Planta Med. 1979;  36 186-7
• 2 Wang M -Y, West B J, Jensen C J, Nowicki D, Su C, Palu A K. et al . Morinda citrifolia (Noni): a literature review and recent advances in Noni research.  Acta Pharmacol Sin. 2002;  23 1127-41
• 3 Pawlus A D, Su B -N, Keller W J, Kinghorn A D. An anthraquinone with potent quinone reductase-inducing activity and other constituents of the fruits of Morinda citrifolia .  J Nat Prod. 2005;  68 1720-2
• 4 Srivastava M, Singh J. A new anthraquinone glycoside from Morinda citrifolia .  Int J Pharmacogn. 1993;  31 182-4
• 5 Kamiya K, Tanaka Y, Endang H, Umar M, Satake T. Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation.  J Agric Food Chem. 2004;  52 5843-8
• 6 Wang M, Kikuzaki H, Csiszar K, Boyd C D, Maunakea A, Fong S FT. et al . Novel trisaccharide fatty acid ester identified from the fruits of Morinda citrifolia (Noni).  J Agric Food Chem. 1999;  47 4880-2
• 7 Wang M, Kikuzaki H, Jin Y, Nakatani N, Zhu N, Csiszar K. et al . Novel glycosides from Noni (Morinda citrifolia).  J Nat Prod. 2000;  63 1182-3
• 8 Su B -N, Pawlus A D, Jung H -A, Keller W J, McLaughlin J L, Kinghorn A D. Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity.  J Nat Prod. 2005;  68 592-5
• 9 Kensler T W. Environ. Chemoprevention by inducers of carcinogen detoxication enzymes.  Health Perspect. 1997;  105 965-70
• 10 Hirazumi A, Furusawa E, Chou S C, Hokama Y. Anticancer activity of Morinda citrifolia (Noni) on intraperitoneally implanted Lewis lung carcinoma in syngeneic mice.  Proc West Pharmacol Soc. 1994;  37 145-6
• 11 Liu G, Bode A, Ma W -Y, Sang S, Ho C -T, Dong Z. Two novel glycosides from the fruits of Morinda citrifolia (Noni) inhibit AP-1 transactivation and cell transformation in the mouse epidermal JB6 cell line.  Cancer Res. 2001;  61 5749-56
• 12 Nyberg N T, Duus J Ø, Sørensen O W. Heteronuclear two-bond correlation: suppressing heteronuclear three-bond or higher NMR correlations while enhancing two-bond correlations even for vanishing ² J _CH .  J Am Chem Soc. 2005;  127 6154-5.
• 13 Berthod A, Ruiz-Angel M J, Carda-Broch S. Elution-extrusion countercurrent chromatography. Use of the liquid nature of the stationary phase to extend the hydrophobicity window.  Anal Chem. 2003;  75 5886-94