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

Ui Joung Youn; Leng Chee Chang

doi:10.20307/nps.2017.23.1.16

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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 Youn^1,^∗, 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

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.

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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.

(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.

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Fig. 1.

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

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Fig. 2.

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

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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
Compounds	% inhib.^a	% surv.^b	IC₅₀ (μM)	% inhib.^c	% surv.^d	IC₅₀ (μM)	IR
1	5.3 ± 1.3	103.4 ± 2.8	nd^e	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-NMMA^g			25.1 ± 2.3
TPCK^h						3.8 ± 0.6
BAY-11^h						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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