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Youn and Chang: Chemical Constituents of Fermented Noni (Morinda citrifolia) Juice Exudates and Their Biological Activity
Original Article

Natural Product Sciences 2017;23(1):16-20.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.1.16

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

Ui Joung Youn1, ∗, Leng Chee Chang2

1Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon, 21990, Republic of Korea

2Department of Pharmaceutical Sciences, Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, HI, 96720, United States

∗Author for correspondence Ui Joung Youn, Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon 21990, Republic of Korea. Tel: +82-32-760-5562; E-mail: ujyoun@kopri.re.kr

Received 28 September 2016       Revised 30 October 2016       Accepted 1 November 2016

Copyright © 2017 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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.

Keywords: Morinda citrifolia, Rubiaceae, alkyl disaccharide, phenyl ethandiol, anti-inflammatory activity

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.
crossref
(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.

Fig. 1.
Structures of compounds 1 – 4 isolated from the fermented noni juice.
nps-23-16f1.tif
Fig. 2.
Important HMBC (arrow) and COSY (bold) correlations for 1 and 3.
nps-23-16f2.tif
Table 1.
Inhibition effects of compounds isolated from fermented noni juice on the TNF-α-induced NF-κB and NO production, and Quinone Reductacse-1 (QR-1) inducing activities
Compounds Nitrite assay NF-κB QR1
% inhib.a % surv.b IC50 (μM) % inhib.c % surv.d IC50 (μM) IR
1 5.3 ± 1.3 103.4 ± 2.8 nde 56.0 ± 2.1 87 ± 4.1 nd 0.8
2 13.3 ± 1.3 79.6 ± 2.8 nd 0 107.6 ± 2.8 nd 1.4
3 3.7 ± 0.1 104.2 ± 0.4 nd 28.0 ± 2.0 88.0 ± 4.0 nd 1.8
4 −f − − − − − −
5 −f − − − − − −
L-NMMAg     25.1 ± 2.3        
TPCKh           3.8 ± 0.6  
BAY-11h           2.0 ± 0.3  

a % inhibition of NO at a concentration of 50 μM,

b % survival at a concentration of 50 μM,

c % inhibition of NF-κB at 50 μM,

d % survival at concentration of 50 μM,

e nd, not determined,

f −, not tested,

g positive control for NO,

h positive control for NF-κB.

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