Nat Prod Sci.  2017 Mar;23(1):16-20. 10.20307/nps.2017.23.1.16.

Chemical Constituents of Fermented Noni (Morinda citrifolia) Juice Exudates and Their Biological Activity

Affiliations
  • 1Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon, 21990, Republic of Korea. ujyoun@kopri.re.kr
  • 2Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States.

Abstract

In a continuing study of the fermented noni (Morinda citrifolia) juice exudates, five compounds, heptanyl 2-O-β-D-xylofuranosyl-(1 → 6)-β-D-glucopyranoside (1), n-butyl β-D-glucopyranoside (2), (1S)-(3-ethenyl-phenyl)-1,2-ethanediol (3), (2S)-2-hydroxybutanedioic acid (4), and daucosterol (5) were isolated from the buthanol partition of the extract. The structures of the isolates were identified by 1D and 2D NMR, and MS experiments, as well as by comparison of their data with the published values. Among the isolates, compounds 1 - 3 were isolated for the first time from the plant species. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit nitric oxide (NO) production and tumor necrosis factor alpha (TNF-α)-induced NF-κB activity, and quinonone reductase-1 (QR1)-inducing effect.

Keyword

Morinda citrifolia; Rubiaceae; alkyl disaccharide; phenyl ethandiol; anti-inflammatory activity

MeSH Terms

Exudates and Transudates*
Morinda*
Nitric Oxide
Plants
Rubiaceae
Tumor Necrosis Factor-alpha
Nitric Oxide
Tumor Necrosis Factor-alpha

Figure

  • Fig. 1. Structures of compounds 1 – 4 isolated from the fermented noni juice.

  • Fig. 2. Important HMBC (arrow) and COSY (bold) correlations for 1 and 3.


Reference

References

(1). Wang M.Y.., West B. J.., Jensen C. J.., Nowicki D.., Su C.., Palu A. K.., Anderson G.Acta Pharmacol. Sin. 2002. 23:1127–1141.
(2). Hirazumi A.., Furusawa E.., Chou S. C.., Hokama Y.Proc. West Pharmacol. Soc. 1996. 39:7–9.
(3). Palu A. K.., Kim A. H.., West B. J.., Deng S.., Jensen J.., White L. J.Ethnopharmacol. 2008. 115:502–506.
(4). Yang J.., Paulino R.., Janke-Stedronsky S.., Abawi F.Food Chem. 2007. 102:302–308.
(5). Jain R. K.., Srivastava S. D.Proc. Nat. Acad. Sci. India. 1992. 62A:11–13.
(6). Deng Y.., Chin Y. W.., Chai H.., Keller W. J.., Kinghorn A. D. J.Nat. Prod. 2007. 70:2049–2052.
(7). Srivastava M.., Singh J.Int. J. Pharmacog. 1993. 31:182–184.
(8). Liu G.., Bode A.., Ma W. Y.., Sang S.., Ho C. T.., Dong Z.Cancer Res. 2001. 61:5749–5756.
(9). Su B. N.., Pawlus A. D.., Jung H. A.., Keller W. J.., McLaughlin J. L.., Kinghorn A. D. J.Nat. Prod. 2005. 68:592–595.
(10). Kanchanapoom T.., Kasai R.., Yamasaki K.Phytochemistry. 2002. 59:551–556.
(11). Sang S.., Cheng X.., Zhu N.., Wang M.., Jhoo J. W.., Stark R. E.., Badmaev V.., Ghai G.., Rosen R. T.., Ho C.T. J.Nat. Prod. 2001. 64:799–800.
(12). Youn U. J.., Park E. J.., Kondratyuk T. P.., Sang-Ngern M.., Wall M. M.., Wei Y.., Pezzuto J. M.., Chang L. C. J.Nat. Prod. 2016. 79:1508–1513.
(13). Kondratyuk T. P.., Park E. J.., Yu R.., van Breemen R.B.., Asolkar R. N.., Murphy B. T.., Fenical W.., Pezzuto J. M.Mar. Drugs. 2012. 1:451–464.
(14). Park E.J.., Kondratyuk T.P.; Morrell, A.; Kiselev, E.; Conda-Sheridan, M.; Cushman, M.; Ahn, S.; Choi, Y.; White, J.J.; van Breemen, R.B.; Pezzuto, J.M. Cancer Prev. Res (Phila). 2011. 4:592–607.
(15). Song L. L.., Kosmeder II J. W.., Lee S. K.., Gerhäuser C.., Lantvit D.., Moon R. C.., Moriarty R. M.., Pezzuto J. M.Cancer Res. 1999. 59:578–585.
(16). Chiang Y.M.., Chuang D.Y.., Wang S.Y.., Kuo Y.H.., Tsai P.W.., Shyur L.F. J.Ethnopharmacol. 2004. 95:409–419.
(17). Yu H.L.., Xu J.H.., Lu W.Y.., Lin G.Q.Enzyme Microb. Tech. 2007. 40:354–361.
(18). Yang W.Q.., Qin X.D.., Shao H.J.., Fang L.Z.., Wang F.., Ding Z.H.., Dong Z.J.., Liu J.K. J.Basic Microbiol. 2007. 47:191–193.
(19). Boger D. L.., Panek J. S. J.Org. Chem. 1981. 46:1208–1210.
(20). Faizi S.., Ali M.., Saleem R.., Irfanullah ., Bibi S.Magn. Reson. Chem. 2001. 39:399–4. -21405.
Article
(21). Choudhary A.., Kumar R.., Srivastava R. B.., Surapaneni S. K.., Tikoo K.., Singh I. P. J.Funct. Foods. 2015. 16:183–193.
(22). Watson C. Y.., Whish W. J. D.., Threadgill M. D.Bioorg. Med. Chem. 1998. 6:721–734.
(23). Akihisa T.., Tochizawa S.., Takahashi N.., Yamamoto A.., Zhang J.., Kikuchi T.., Fukatsu M.., Tokuda H.., Suzuki N.Chem. Biodivers. 2012. 9:1172–1187.
Full Text Links
  • NPS
Actions
Cited
CITED
export Copy
Close
Share
  • Twitter
  • Facebook
Similar articles
Copyright © 2024 by Korean Association of Medical Journal Editors. All rights reserved.     E-mail: koreamed@kamje.or.kr