Review of Pharmacological Activities of Michelia Alba

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REVIEW ON PHARMACOLOGICAL ACTIVITIES OF MICHELIA ALBA

Chien-Hsing Lee1 , Hsin-Liang Chen2, Hsing-Tan Li2, Wen-Ying Chao1, Chung-Yi Chen2*

1Department of Nursing, Min-Hwei College of Health Care Management, Tainan, Taiwan.

2School of Medical and Health Sciences, Fooyin University, Kaohsiung, Taiwan.

ABSTRACT

This review describes the morphological, phytochemical and pharmacological properties of Michelia alba (Magnoliaceae). The genus Michelia (Magnoliaceae) consists of approximately 30 species. Michelia alba D.C. is a tall tree native to Indonesia and has been used by the native Malays in Indonesia and Malaysia for medicinal purposes. The tree producing these flowers ranges from 10 to 15 meters in height and can grow up to 20 meters if cultivated in a high-moisture area. Cracks in the stem bark are in a reticulated pattern along the trunk. Michelia alba is an annual flowering plant; generally the flowers begin to bloom in the evening, with their scent becoming widespread; the scent begins to fade in the afternoon. Gardeners usually collect the flowers twice a day: at night and at dawn. This plant was used for the treatment of fever, syphilis, gonorrhoea and malaria, and was regarded traditionally as an abortive agent. The present paper enumerates an overview of phytochemical composition and pharmacological aspects that is useful to researchers for further exploration for necessary development of this potential herb.

Key Words:- Michelia alba, Magnoliaceae, phytochemical, pharmacological properties.

INTRODUCTION

The genus Michelia (Magnoliaceae) consists of about 30 species. One of these species is native to Taiwan. Michelia species are traditionally used by indigenous people for the treatment of cancer (Wang et al., 2010b). For example, Michelia champaca has been utilized in India for the treatment of abdominal tumours, and Michelia hypoleuca and M. officinalis for carcinomatous sores and leukaemia, respectively, in China (Wang et al., 2010b). Michelia alba is a tall tree native to Indonesia and has been used by the native Malays in Malaysia and Indonesia for medicinal purposes. The bark is used for the treatment of fever, syphilis, gonorrhoea and malaria, and

Corresponding Author

Chung-Yi Chen

Email:- [email protected]

the white fragrant flower is used traditionally as an abortive agent (Chen et al., 2008; Wang et al., 2010b). We have found four aporphines, two oxoaporphines, three sesquiterpene lactones, one amide, one lignan, three benzenoids, two steroids, three aliphatic compounds and two chlorophylls from the leaves of Michelia alba (Wang et al., 2010b). Previously, this plant had been isolated 43 compounds, including nine aporphines (1-9), three oxoaporphines (10-12), one amide (13), one alkaloid (14), two lignans (15 and 16), one monoterpene (17), nine sesquiterpenes (18-26), eight benzenoids (27-34), one triterpene (35), two steroids, three aliphatic compounds, and three chlorophylls (Asaruddin, et al., 2003; Chen et al., 2008a; Lo et al., 2010; Wang et al., 2010b; Yang, 1962). As part of our continuing investigation into the phytochemical and bioactive compounds of

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Magnoliaceous plants, a new chlorophyll, michephyll A, together with 9 known compounds, (-)-N-formylanonaine (3), (-)-oliveroline (6), (-)-nornuciferine (9), lysicamine (12), (+)-epi-yangambin (16), (+)-cyperone (18), ficaprenol-10 (35), pheophytin a and aristophyll C were obtained via chromatographic fractionation of the methanolic extract of the leaves of this plant (Wang et al., 2010b). The objective of this article is to collect information on Michelia alba, which may help the investigator to realize for the efficacy and potency of this herb.

PHARMACOLOGICAL ACTIVITIES

Anticancer activity

(-)-Anonaine (1), a major alkaloid compound, is isolated from the leaves of Michelia alba. Current studies demonstrated that (-)-anonaine (1) provided some biological and pharmacological activities, including vasorelaxant, antibacterial, antifungal, anti-oxidative, and antidepressant effects (Chulia et al., 1995; Martinez et al., 1992; Paulo Mde et al., 1992; Protais et al., 1995; Tsai et al., 1989; Ubeda et al., 1993; Valiente et al., 2004; Villar et al., 1987). Importantly, recent studies have been demonstrated that (-)-anonaine (1) has some anticancer activities. Treatment with (-)-anonaine (1) induces dose-dependent DNA damage that is correlated with increased intracellular nitric oxide, reactive oxygen species, glutathione depletion, disruptive mitochondrial transmembrane potential, activation of caspase 3, 7, 8, and 9, and poly ADP ribose polymerase cleavage, up-regulated the expression of Bax as well as p53 proteins (Chen et al., 2008). In addition, (-)-anonaine (1) has been reported significant inhibition to cell growth and migration activities of lung cancer cells (Chen et al., 2011). The above-mentioned mechanisms of (-)-anonaine (1) seem to be promising for cancer prevention; however, further clinical studies are warranted to assess the efficacy and safety of (-)-anonaine (1).

Skin protection

Tyrosinase is known to be the first two and rate-limiting enzyme in the synthesis of melanin pigments responsible for colouring skin, hair and eyes (Slominski et al., 2005). In human skin melanocytes, the cellular tyrosinase inhibition was examined by the conversion of L-tyrosine and oxidation of L-DOPA to dopaquinone (Park et al., 2009). Recent study, (-)-N-formylanonaine (3), one of active ingredients of Michelia alba, was found to inhibit mushroom tyrosinase and to have tyrosinase and melanin reducing activities in human epidermal melanocytes without apparent cytotoxicity to human cells. The results indicate that it suppresses tyrosinase activity and total melanin content without having adverse affects. Furthermore, (-)-N-formylanonaine (3) is superior to the known tyrosinase inhibitors, such as kojic acid and 1-phenyl-2-thiourea (PTU) (Wang et al., 2010a). A recent study demonstrated that Michelia alba leaves extract and their hydrolysates can attenuate UVB-induced expression of matrix metalloproteinases, elastase, hyaluronic acid and type I procollagen in human dermal fibroblasts (Chiang et al., 2012).

Conclusion

This review reveals the multiple benefits of Michelia alba which made it a valuable potential of nature. The anti-cancer and skin protection effects of Michelia alba has been investigated extensively, however this plant has not yet been developed as preclinical trials. Future studies on determining the anticancer activity of Michelia alba and its active components should ideally include human intervention trials to investigate its effectiveness against human cancers and other diseases.

REFERENCES

Asaruddin MR, Honda G, Tsubouchi A, Nakajima-Shimada J, Aoki T and Kiuchi F. Trypanocidal constituents from Michelia alba. Nat. Med, 57(2), 2003, 61-63.

Chen BH, Chang HW, Huang HM, Chong IW, Chen JS, Chen CY, Wang HM. (-)-Anonaine induces DNA damage and inhibits growth and migration of human lung carcinoma h1299 cells. J. Agric. Food. Chem, 59(6), 2011, 2284-2290.

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Chen CY, Liu TZ, Tseng WC, Lu FJ, Hung RP and Chen CH. (-)-Anonaine induces apoptosis through Bax- and caspase-dependent pathways in human cervical cancer (HeLa) cells. Food Chem. Toxicol, 46(8), 2008, 2694-2702.

Chiang HM, Chen HC, Lin TJ, Shih IC and Wen KC. Michelia alba extract attenuates UVB-induced expression of matrix metalloproteinases via MAP kinase pathway in human dermal fibroblasts. Food Chem. Toxicol, 50(12), 2012, 4260-9.

Chulia S, Ivorra MD, Cave A, Cortes D, Noguera MA and D’Ocon MP. Relaxant activity of three aporphine alkaloids from Annona cherimolia on isolated aorta of rat. J. Pharm. Pharmacol, 47(8), 1995, 647-650.

Lo WL, Huang LY, Wang HM and Chen CY. Chemical constituents from the stems of Michelia alba. Chem. Nat. Compd, 46(4), 2010, 664-665.

Martinez LA, Rios JL, Paya M and Alcaraz MJ. Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids. Free Radic. Biol. Med, 12(4), 1992, 287-292.

Park SH, Kim DS, Lee HK, Kwon SB, Lee S, Ryoo IJ, Kim WG, Yoo ID and Park KC. Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression. Exp. Dermatol, 18(6), 2009, 562-566.

Paulo Mde Q, Barbosa-Filho JM, Lima EO, Maia RF, Barbosa Rde C and Kaplan MA. Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C. J. Ethnopharmacol, 36(1), 1992, 39-41.

Protais P, Arbaoui J, Bakkali EH, Bermejo A and Cortes D. Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes. J. Nat. Prod, 58(10), 1995, 1475-1484.

Slominski A, Wortsman J, Plonka PM, Schallreuter KU, Paus R and Tobin DJ. Hair follicle pigmentation. J. Invest. Dermatol, 124(1), 2005, 13-21.

Tsai IL, Liou YF and Lu ST. Screening of isoquinoline alkaloids and their derivatives for antibacterial and antifungal activities. Kaohsiung J. Med. Sci, 5(3), 1989, 132-145.

Ubeda A, Montesinos C, Paya M and Alcaraz MJ. Iron-reducing and free-radical-scavenging properties of apomorphine and some related benzylisoquinolines. Free Radic. Biol. Med, 15(2), 1993, 159-167.

Valiente M, D’Ocon P, Noguera MA, Cassels BK, Lugnier C and Ivorra MD. Vascular activity of (-)-anonaine, (-)-roemerine and (-)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes. Planta Med, 70(7), 2004, 603-609.

Villar A, Mares M, Rios JL, Canton E and Gobernado M. Antimicrobial activity of benzylisoquinoline alkaloids. Pharmazie, 42(4), 1987, 248-250.

Wang HM, Chen CY, Ho ML, Chou YT, Chang HC, Lee CH, Wang CZ and Chu IM. (-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant. Bioorg Med. Chem, 18(14), 2010a, 5241-5247.

Wang HM, Lo WL, Huang LY, Wang YD and Chen CY. Chemical constituents from the leaves of Michelia alba. Nat. Prod. Res, 24(5), 2010b, 398-406.

Yang TH. Alkaloids of magnoliaceous plants, XXXI. Alkaloids of Michelia alba. Yakugaku Zasshi, 82, 1962, 811-816.

REVIEW ON PHARMACOLOGICAL ACTIVITIES OF MICHELIA ALBA

Chien-Hsing Lee1 , Hsin-Liang Chen2, Hsing-Tan Li2, Wen-Ying Chao1, Chung-Yi Chen2*

1Department of Nursing, Min-Hwei College of Health Care Management, Tainan, Taiwan.

2School of Medical and Health Sciences, Fooyin University, Kaohsiung, Taiwan.

ABSTRACT

This review describes the morphological, phytochemical and pharmacological properties of Michelia alba (Magnoliaceae). The genus Michelia (Magnoliaceae) consists of approximately 30 species. Michelia alba D.C. is a tall tree native to Indonesia and has been used by the native Malays in Indonesia and Malaysia for medicinal purposes. The tree producing these flowers ranges from 10 to 15 meters in height and can grow up to 20 meters if cultivated in a high-moisture area. Cracks in the stem bark are in a reticulated pattern along the trunk. Michelia alba is an annual flowering plant; generally the flowers begin to bloom in the evening, with their scent becoming widespread; the scent begins to fade in the afternoon. Gardeners usually collect the flowers twice a day: at night and at dawn. This plant was used for the treatment of fever, syphilis, gonorrhoea and malaria, and was regarded traditionally as an abortive agent. The present paper enumerates an overview of phytochemical composition and pharmacological aspects that is useful to researchers for further exploration for necessary development of this potential herb.

Key Words:- Michelia alba, Magnoliaceae, phytochemical, pharmacological properties.

INTRODUCTION

The genus Michelia (Magnoliaceae) consists of about 30 species. One of these species is native to Taiwan. Michelia species are traditionally used by indigenous people for the treatment of cancer (Wang et al., 2010b). For example, Michelia champaca has been utilized in India for the treatment of abdominal tumours, and Michelia hypoleuca and M. officinalis for carcinomatous sores and leukaemia, respectively, in China (Wang et al., 2010b). Michelia alba is a tall tree native to Indonesia and has been used by the native Malays in Malaysia and Indonesia for medicinal purposes. The bark is used for the treatment of fever, syphilis, gonorrhoea and malaria, and

Corresponding Author

Chung-Yi Chen

Email:- [email protected]

the white fragrant flower is used traditionally as an abortive agent (Chen et al., 2008; Wang et al., 2010b). We have found four aporphines, two oxoaporphines, three sesquiterpene lactones, one amide, one lignan, three benzenoids, two steroids, three aliphatic compounds and two chlorophylls from the leaves of Michelia alba (Wang et al., 2010b). Previously, this plant had been isolated 43 compounds, including nine aporphines (1-9), three oxoaporphines (10-12), one amide (13), one alkaloid (14), two lignans (15 and 16), one monoterpene (17), nine sesquiterpenes (18-26), eight benzenoids (27-34), one triterpene (35), two steroids, three aliphatic compounds, and three chlorophylls (Asaruddin, et al., 2003; Chen et al., 2008a; Lo et al., 2010; Wang et al., 2010b; Yang, 1962). As part of our continuing investigation into the phytochemical and bioactive compounds of

Magnoliaceous plants, a new chlorophyll, michephyll A, together with 9 known compounds, (-)-N-formylanonaine (3), (-)-oliveroline (6), (-)-nornuciferine (9), lysicamine (12), (+)-epi-yangambin (16), (+)-cyperone (18), ficaprenol-10 (35), pheophytin a and aristophyll C were obtained via chromatographic fractionation of the methanolic extract of the leaves of this plant (Wang et al., 2010b). The objective of this article is to collect information on Michelia alba, which may help the investigator to realize for the efficacy and potency of this herb.

PHARMACOLOGICAL ACTIVITIES

Anticancer activity

(-)-Anonaine (1), a major alkaloid compound, is isolated from the leaves of Michelia alba. Current studies demonstrated that (-)-anonaine (1) provided some biological and pharmacological activities, including vasorelaxant, antibacterial, antifungal, anti-oxidative, and antidepressant effects (Chulia et al., 1995; Martinez et al., 1992; Paulo Mde et al., 1992; Protais et al., 1995; Tsai et al., 1989; Ubeda et al., 1993; Valiente et al., 2004; Villar et al., 1987). Importantly, recent studies have been demonstrated that (-)-anonaine (1) has some anticancer activities. Treatment with (-)-anonaine (1) induces dose-dependent DNA damage that is correlated with increased intracellular nitric oxide, reactive oxygen species, glutathione depletion, disruptive mitochondrial transmembrane potential, activation of caspase 3, 7, 8, and 9, and poly ADP ribose polymerase cleavage, up-regulated the expression of Bax as well as p53 proteins (Chen et al., 2008). In addition, (-)-anonaine (1) has been reported significant inhibition to cell growth and migration activities of lung cancer cells (Chen et al., 2011). The above-mentioned mechanisms of (-)-anonaine (1) seem to be promising for cancer prevention; however, further clinical studies are warranted to assess the efficacy and safety of (-)-anonaine (1).

Skin protection

Tyrosinase is known to be the first two and rate-limiting enzyme in the synthesis of melanin pigments responsible for colouring skin, hair and eyes (Slominski et al., 2005). In human skin melanocytes, the cellular tyrosinase inhibition was examined by the conversion of L-tyrosine and oxidation of L-DOPA to dopaquinone (Park et al., 2009). Recent study, (-)-N-formylanonaine (3), one of active ingredients of Michelia alba, was found to inhibit mushroom tyrosinase and to have tyrosinase and melanin reducing activities in human epidermal melanocytes without apparent cytotoxicity to human cells. The results indicate that it suppresses tyrosinase activity and total melanin content without having adverse affects. Furthermore, (-)-N-formylanonaine (3) is superior to the known tyrosinase inhibitors, such as kojic acid and 1-phenyl-2-thiourea (PTU) (Wang et al., 2010a). A recent study demonstrated that Michelia alba leaves extract and their hydrolysates can attenuate UVB-induced expression of matrix metalloproteinases, elastase, hyaluronic acid and type I procollagen in human dermal fibroblasts (Chiang et al., 2012).

Conclusion

This review reveals the multiple benefits of Michelia alba which made it a valuable potential of nature. The anti-cancer and skin protection effects of Michelia alba has been investigated extensively, however this plant has not yet been developed as preclinical trials. Future studies on determining the anticancer activity of Michelia alba and its active components should ideally include human intervention trials to investigate its effectiveness against human cancers and other diseases.

REFERENCES

Asaruddin MR, Honda G, Tsubouchi A, Nakajima-Shimada J, Aoki T and Kiuchi F. Trypanocidal constituents from Michelia alba. Nat. Med, 57(2), 2003, 61-63.

Chen BH, Chang HW, Huang HM, Chong IW, Chen JS, Chen CY, Wang HM. (-)-Anonaine induces DNA damage and inhibits growth and migration of human lung carcinoma h1299 cells. J. Agric. Food. Chem, 59(6), 2011, 2284-2290.

Chen CY, Liu TZ, Tseng WC, Lu FJ, Hung RP and Chen CH. (-)-Anonaine induces apoptosis through Bax- and caspase-dependent pathways in human cervical cancer (HeLa) cells. Food Chem. Toxicol, 46(8), 2008, 2694-2702.

Chiang HM, Chen HC, Lin TJ, Shih IC and Wen KC. Michelia alba extract attenuates UVB-induced expression of matrix metalloproteinases via MAP kinase pathway in human dermal fibroblasts. Food Chem. Toxicol, 50(12), 2012, 4260-9.

Chulia S, Ivorra MD, Cave A, Cortes D, Noguera MA and D’Ocon MP. Relaxant activity of three aporphine alkaloids from Annona cherimolia on isolated aorta of rat. J. Pharm. Pharmacol, 47(8), 1995, 647-650.

Lo WL, Huang LY, Wang HM and Chen CY. Chemical constituents from the stems of Michelia alba. Chem. Nat. Compd, 46(4), 2010, 664-665.

Martinez LA, Rios JL, Paya M and Alcaraz MJ. Inhibition of nonenzymic lipid peroxidation by benzylisoquinoline alkaloids. Free Radic. Biol. Med, 12(4), 1992, 287-292.

Park SH, Kim DS, Lee HK, Kwon SB, Lee S, Ryoo IJ, Kim WG, Yoo ID and Park KC. Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression. Exp. Dermatol, 18(6), 2009, 562-566.

Paulo Mde Q, Barbosa-Filho JM, Lima EO, Maia RF, Barbosa Rde C and Kaplan MA. Antimicrobial activity of benzylisoquinoline alkaloids from Annona salzmanii D.C. J. Ethnopharmacol, 36(1), 1992, 39-41.

Protais P, Arbaoui J, Bakkali EH, Bermejo A and Cortes D. Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes. J. Nat. Prod, 58(10), 1995, 1475-1484.

Slominski A, Wortsman J, Plonka PM, Schallreuter KU, Paus R and Tobin DJ. Hair follicle pigmentation. J. Invest. Dermatol, 124(1), 2005, 13-21.

Tsai IL, Liou YF and Lu ST. Screening of isoquinoline alkaloids and their derivatives for antibacterial and antifungal activities. Kaohsiung J. Med. Sci, 5(3), 1989, 132-145.

Ubeda A, Montesinos C, Paya M and Alcaraz MJ. Iron-reducing and free-radical-scavenging properties of apomorphine and some related benzylisoquinolines. Free Radic. Biol. Med, 15(2), 1993, 159-167.

Valiente M, D’Ocon P, Noguera MA, Cassels BK, Lugnier C and Ivorra MD. Vascular activity of (-)-anonaine, (-)-roemerine and (-)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes. Planta Med, 70(7), 2004, 603-609.

Villar A, Mares M, Rios JL, Canton E and Gobernado M. Antimicrobial activity of benzylisoquinoline alkaloids. Pharmazie, 42(4), 1987, 248-250.

Wang HM, Chen CY, Ho ML, Chou YT, Chang HC, Lee CH, Wang CZ and Chu IM. (-)-N-Formylanonaine from Michelia alba as a human tyrosinase inhibitor and antioxidant. Bioorg Med. Chem, 18(14), 2010a, 5241-5247.

Wang HM, Lo WL, Huang LY, Wang YD and Chen CY. Chemical constituents from the leaves of Michelia alba. Nat. Prod. Res, 24(5), 2010b, 398-406.

Yang TH. Alkaloids of magnoliaceous plants, XXXI. Alkaloids of Michelia alba. Yakugaku Zasshi, 82, 1962, 811-816.

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