Distribution of Naturally Occurring Anthraquinones, Iridoids and Flavonoids from Morinda genus: Chemistry and Biological activity

Authors

  • Wong PHAKHODEE Department of Chemistry, Faculty of Science, Chiang Mai University 50200

Keywords:

Rubiaceae, Morinda, anthraquinone, iridoid, flavonoid, biological activity

Abstract

The present review covers chemistry and bioactivities of anthraquinones, iridoids, and flavonoids from the Morinda genus. The plants of Morinda species, belonging to the Rubiaceae family, have been used as traditional folk medicine with anti-bacterial, anti-fungal, anti-tumor, anti-helmin, analgesic, anti-inflammatory, and immune enhancing effects. They are rich sources of anthraquinones and iridoids. The relevant 2-methoxy-1,3,6-trihydroxyanthraquinone is one of the most potent quinone reductase enzyme inducers with no cytotoxicity with normal cells. Damnacanthol-3-O-b-D-primeveroside and lucidin-3-O-b-D-primeveroside displayed a significant reduction of the blood glucose levels in anti-diabetic tests. Additionally, iridoids, 9-epi-6a-methoxy geniposidic acid, scandoside methyl ester, asperulosidic acid, showed a more potent inhibitory effect of melanogenesis than the commercial available depigmented arbutin used in cosmetic industry.

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Author Biography

Wong PHAKHODEE, Department of Chemistry, Faculty of Science, Chiang Mai University 50200

Department of Chemistry

References

W Mian-Ying, BJ West, CJ Jensen, D Nowicki, S Chen, A Palu and G Anderson. Morinda citrifolia (noni): A literature review and recent advances in noni research. Acta. Pharmacol. Sin. 2002; 12, 1127-41.

L Lv, H Chen, C-T Ho and S Sang. Chemical components of the roots of noni (Morinda citrifolia) and their cytotoxic effects. Fitoterapia 2011; 82, 704-8.

AD Pawlus, BN Su, WJ Keller and AD Kinghorn. An anthraquinone with potent quinone reductase-inducing activity and other constituents of the fruits of Morinda citrifolia (noni). J. Nat. Prod. 2005; 68, 1720-2.

Jasril, NH Lajis, LY Mooi, MA Abdullah, MA Sukari and AM Ali. Antitumor promoting and antioxidant activities of anthraquinones isolated from the cell suspension culture of Morinda elliptica. AsPac J. Mol. Biol. Biotechnol. 2003; 11, 3-7.

Y Deng, YW Chin, H Chai, WJ Keller and AD Kinghorn. Anthraquinones with quinone reductase-inducing activity and benzophenones from Morinda citrifolia (noni) roots. J. Nat. Prod. 2007; 70, 2049-52.

T Ruksilp, J Sichaem, S Khumkratok, P Siripong and S Tip-pyang. Anthraquinones and an iridoid glycoside from the roots of Morinda pandurifolia. Biochem. Sys. Ecol. 2011; 39, 888-92.

AD Pawlus and AD Kinghorn. Review of the ethnobotany, chemistry, biological activity and safety of the botanical dietary supplement Morinda citrifolia (noni). J. Pharm. Pharmacol. 2007; 59, 1587-609.

O Potterat and M Hamburger. Morinda citrifolia (noni) fruit-phytochemistry, pharmacology, safety. Planta Med. 2007; 73, 191-9.

K Kamiya, W Hamabe, S Harada, R Murakami, S Tokuyama and T Satake. Chemical constituents of Morinda citrifolia roots exhibit hypoglycemic effects in streptozotocin-induced diabetic mice. Biol. Pharm. Bull. 2008; 31, 935-8.

K Kamiya, W Hamabe, S Tokuyama and T Satake. New antraquinone glycosides from the roots of Morinda citrifolia. Fitoterapia 2009; 80, 196-9.

AM Ali, NH Ismail, MM Mackeen, LS Yazan, SM Mohamed, ASH Ho and NH Lajis. Antiviral, cytotoxic and antimicrobial activity of anthraquinones isolated from the root of Morinda elliptica. Pharm. Biol. 2000; 38, 298-301.

Y Zhang, P Talalay, CG Cho and GH Posner. A major inducer of anticarcinogenic protective enzymes from broccoli: Isolation and elucidation of structure. Proc. Natl. Acad. Sci. USA 1992; 89, 2399-403.

G Rath, M Ndonzao and K Hostettmann. Antifungal anthraquinones from Morinda lucida. Int. J. Pharmacogn. 1995; 33, 107-14.

HL Zhang, QW Zhang, XQ Zhang, WC Ye and YT Wang. Chemical constituents from the root of Morinda officinalis. Chin. J. Nat. Med. 2010; 8, 192-5.

YB Wu, CJ Zheng, LP Qin, LN Sun, T Han, L Jiao, QY Zhang and JZ Wu. Antiosteoporotic activity of anthraquinones from Morinda officinalis on osteoblasts and osteoclasts. Molecules 2009; 14, 573-83.

BS Siddiqui, FA Sattar, F Ahmad and S Begum. Isolation and structural elucidation of chemical constituents from the fruits of Morinda citrifolia Linn. Arch. Pharm. Res. 2007; 30, 919-23.

GCL Ee, YP Wen, MA Sukari, R Go and HL Lee. A new anthraquinone from Morinda citrifolia roots. Nat. Prod. Res. 2009; 23, 1322-9.

NH Ismail, AM Ali, N Aimi, M Kitajima, H Takayama and NH Lajis. Anthraquinones from Morinda elliptica. Phytochemistry 1997; 45, 1723-5.

K Kamiya, Y Tanaka, H Endang, M Umar and T Satake. New anthraquinine and iridoid from the fruits of Morinda citrifolia. Chem. Pharm. Bull. 2005; 53, 1597-9.

W Xiang, QS Song, H-J Zhang and SP Guo. Antimicrobial anthraquinones from Morinda angustifolia. Fitoterapia 2008; 79, 501-4.

T Akihisa, K Matsumoto, H Tokuda, K Yasukawa, K Seino, K Nakamoto, H Kuninaga, T Suzuki and Y Kimura. Anti-inflammatory and potential cancer chemopreventive constituents of the fruits of Morinda citrifolia (noni). J. Nat. Prod. 2007; 70, 754-7.

BS Siddiqui, FA Sattar, S Begum, T Gulzar and F Ahmad. New anthraquinones from the stem of Morinda citrifolia Linn. Nat. Prod. Res. 2006; 20, 1136-44.

CF Lin, CL Ni, YL Huang, SJ Sheu and CC Chen. Lignans and anthraquinones from the fruits of Morinda citrifolia. Nat. Prod. Res. 2007; 21, 1199-204.

J Takashima, Y Ikeda, K Komiyama, M Hayashi, A Kishida and A Ohsaki. New constituents from the leaves of Morinda citrifolia. Chem. Pharm. Bull. 2007; 55, 343-5.

T Akihisa, K Seino, E Kaneko, K Watanabe, S Tochizawa, M Fukatsu, N Banno, K Metori and Y Kimura. Melanogenesis inhibitory activities of iridoid-hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (noni). J. Oleo Sci. 2010; 59, 49-57.

J Schripsema, GP Caprini and D Dagnino. Revision of the structures of citrifolinin A, citrifolinoside, yopaaoside A, yopaaoside B, and morindacin, iridoids from Morinda citrifolia L. and Morinda coreia Ham. Org. Lett. 2006; 8, 5337-40.

V Samoylenko, J Zhao, DC Dunbar, IA Khan, JW Rushing and I Muhammad. New constituents from noni (Morinda citrifolia) fruit juice. J. Agric. Food Chem. 2006; 54, 6398-402.

T Kanchanapoom, R Kasai and K Yamasaki. Iridoid and phenolic glycosides from Morinda coreia. Phytochemistry 2002; 59, 551-6.

G Liu, A Bode, WY Ma, S Sang, CT Ho and Z Dong. 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.

P Noiarsa, S Ruchirawat, H Otsuka and T Kanchanapoom. A new iridoid glucoside from the Thai medicinal plant, Morinda elliptica Ridl. J. Nat. Med. 2006; 60, 322-4.

S Sang, M Wang, K He, G Liu, Z Dong, V Badmaev, QY Zheng, G Ghai, RT Rosen and CT Ho. Chemical components in noni fruits and leaves (Morinda citrifolia L.). ACS. Sym. Ser. 2002; 803, 134-50.

XL Yang, MY Jiang, KL Hsieh and JK Liu. Chemical constituents from the seeds of Morinda citrifolia. Chin. J. Nat. Med. 2009; 7, 119-22.

BN Su, AD Pawlus, HA Jung, WJ Keller, JL McLaughlin and AD Kinghorn. Chemical constituents of the fruits of Morinda citrifolia (noni) and their antioxidant activity. J. Nat. Prod. 2005; 68, 592-5.

S Sang, X Cheng, N Zhu, RE Stark, V Badmaev, G Ghai, RT Rosen and CT Ho. Flavonol glycosides and novel iridoid glycoside from the leaves of Morinda citrifolia. J. Agric. Food Chem. 2001; 49, 4478-81.

S Sang, K He, G Liu, N Zhu, M Wang, J Jhoo, Q Zheng, Z Dong, G Ghai, RT Rosen and CT Ho. Citrifolinin A, a new unusual iridoid with inhibition of activator protein-1 (AP-1) from the leaves of noni (Morinda citrifolia L.). Tetrahedron Lett. 2001; 42, 1823-5.

S Sang, G Liu, K He, N Zhu, Z Dong, Q Zheng, RT Rosen and CT Ho. New unusual iridois from the leaves of noni (Morinda citrifolia L.) show inhibitory effect on ultraviolet B-induced transcriptional activator protein-1 (AP-1) activity. Bioorg. Med. Chem. 2003; 11, 2499-502.

K Cimanga, N Hermans, S Apers, SV Miert, H Van den Heuvel, M Claeys, L Pieters and A Vlietinck. Complement-inhibiting iridoids from Morinda morindoides. J. Nat. Prod. 2003; 66, 97-102.

S Tamura, BK Kubata, Syamsurizal, S Itagaki, T Horii, MK Taba and N Murakami. New anti-malarial phenylpropanoid conjugated iridoids from Morinda morindoides. Bioorg. Med. Chem. Lett. 2010; 20, 1520-3.

S Sang, X Cheng, N Zhu, M Wang, JW Jhoo, RE Stark, V Badmaev, G Ghai, RT Rosen and CT Ho. Iridoid glycosides from the leaves of Morinda citrifolia. J. Nat. Prod. 2001; 64, 799-800.

S Sang, K He, G Liu, N Zhu, X Cheng, M Wang, Q Zheng, Z Dong, G Ghai, RT Rosen and CT Ho. A new unusual iridoid with inhibition of activator protein-1 (AP-1) from the leaves of Morinda citrifolia L. Org. Lett. 2001; 3, 1307-9.

YJ Lim, EH Lee, TH Kang, SK Ha, MS Oh, SM Kim, TJ Yoon, C Kang, JH Park and SY Kim. Inhibitory effects of arbutin on melanin biosynthesis of alfa-melanocyte stimulating hormone-induced hyperpigmentation in cultured brownish guinea pig skin tissues. Arch. Pharm. Res. 2009; 32, 367-73.

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Published

2012-03-28

How to Cite

PHAKHODEE, W. (2012). Distribution of Naturally Occurring Anthraquinones, Iridoids and Flavonoids from Morinda genus: Chemistry and Biological activity. Walailak Journal of Science and Technology (WJST), 9(3), 173–188. Retrieved from https://wjst.wu.ac.th/index.php/wjst/article/view/264