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01-07-2014 | Original Paper

Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox

Authors: Toshio Morikawa, Yusuke Nakanishi, Kiyofumi Ninomiya, Hisashi Matsuda, Souichi Nakashima, Hisako Miki, Yu Miyashita, Masayuki Yoshikawa, Takao Hayakawa, Osamu Muraoka

Published in: Journal of Natural Medicines | Issue 3/2014

Abstract

A methanol extract of the flower buds of Chimonanthus praecox (L.) Link (Calycanthaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, five dimeric pyrrolidinoindoline alkaloids and four sesquiterpenes were isolated, together with 16 known compounds. Among them, (−)-chimonanthine (1, IC₅₀ = 0.93 μM), (−)-folicanthine (2, 1.4 μM), and (−)-calycanthidine (3, 1.8 μM) showed potent inhibitory effects without notable cytotoxicity at the effective concentrations. The most potent alkaloid (1) inhibited both tyrosinase and tyrosine-related protein-1 mRNA expressions, to which the melanogenesis inhibitory activity would be ascribable.

Zhang J-W, Gao J-M, Xu T, Zhang X-C, Ma Y-T, Jarussophon S, Konishi Y (2009) Antifungal activity of alkaloids from the seeds of Chimonanthus praecox. Chem Biodiv 6:838–845CrossRef

Wang W-X, Cao L, Xiong J, Xia G, Hu J-F (2011) Constituents from Chimonanthus praecox (wintersweet). Phytochem Lett 4:271–274CrossRef

Lv J-S, Zhang L-L, Chu X-Z, Zhou J-F (2012) Chemical composition, antioxidant and antimicrobial activity of the extracts of the flowers of the Chinese plant Chimonanthus praecox. Nat Prod Res 26:1363–1367PubMedCrossRef

Takayama H, Matsuda Y, Masubuchi K, Ishida A, Kitajima M, Aimi N (2004) Isolation, structure elucidation, and total synthesis of two new Chimonanthus alkaloids, chimonamidine and chimonanthidine. Tetrahedron 60:893–900CrossRef

Kitajima M, Mori I, Arai K, Kogure N, Takayama H (2006) Two new tryptamine-derived alkaloids from Chimonanthus praecox f. concolor. Tetrahedron Lett 47:3199–3202CrossRef

Prota G (1988) Progress in the chemistry of melanins and related metabolites. Med Res Rev 8:525–556PubMedCrossRef

Kim YJ, Uyama H (2005) Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future. Cell Mol Life Sci 62:1707–1723PubMedCrossRef

Hearing VJ, Korner AM, Pawelek JM (1982) New regulators of melanogenesis are associated with purified tyrosinase isozymes. J Invest Dermatol 79:16–18PubMedCrossRef

Hearing VJ, Jiménez M (1987) Mammalian tyrosinase-the critical regulatory control point in melanocyte pigmentation. Int J Biochem 19:1141–1147PubMedCrossRef

10.

Kuzumaki T, Matsuda A, Wakamatsu K, Ito S, Ishikawa K (1993) Eumelanin biosynthesis is regulated by coordinate expression of tyrosinase and tyrosinase-related protein-1 genes. Exp Cell Res 207:33–40PubMedCrossRef

11.

Friedmann PS, Gilchrest BA (1987) Ultraviolet radiation directly induces pigment production by cultured human melanocytes. J Cell Physiol 133:88–94PubMedCrossRef

12.

Hunt G, Todd C, Cresswell JE, Thody AJ (1994) Alpha-melanocyte stimulating hormone and its analogue Nle4DPhe7 alpha-MSH affect morphology, tyrosinase activity and melanogenesis in cultured human melanocytes. J Cell Sci 107:205–211PubMed

13.

Steinberg ML, Whittaker JR (1976) Stimulation of melanotic expression in a melanoma cell line by theophylline. J Cell Physiol 87:265–275PubMedCrossRef

14.

Wong G, Pawelek J (1975) Melanocyte-stimulating hormone promotes activation of pre-existing tyrosinase molecules in Cloudman S91 melanoma cells. Nature 255:644–646PubMedCrossRef

15.

Matsuda H, Morikawa T, Ninomiya K, Yoshikawa M (2001) Hepatoprotective constituents from Zedoariae rhizome: absolute stereostructures of three new carabrane-type sesquiterpenes, curcumenolactiones A, B, and C. Bioorg Med Chem 9:909–916PubMedCrossRef

16.

Raharivelomanana P, Bianchini J-P, Cambon A, Azzaro M, Faure R (1995) Two-dimensional NMR of sesquiterpenes 8—complete assignment of ¹H and ¹³C NMR spectra of seven sesquiterpene alcohols from Neocallitropsis pancheri. Magn Reson Chem 33:233–235CrossRef

17.

Matsuda H, Kageura T, Oda M, Morikawa T, Sakamoto Y, Yoshikawa M (2001) Effects of constituents from the bark of Magnolia obovata on nitric oxide production in lipopolysaccharide-activated macrophages. Chem Pharm Bull 49:716–720PubMedCrossRef

18.

Kitagawa I, Cui Z, Son BW, Kobayashi M, Kyogoku Y (1987) Marine natural products. XVII. Nephtheoxydiol, a new cytotoxic hydroperoxy-germacrane sesquiterpene, and related sesquiterpenoids from an Okinawan soft coral of Nephthea sp. (Nephtheidae). Chem Pharm Bull 35:124–135PubMedCrossRef

19.

Kim JS, Kim JC, Shim SH, Lee EJ, Jin WY, Bae K, Son KH, Kim HP, Kang SS, Chang HW (2006) Chemical constituents of the root of Dystaenia takeshimana and their anti-inflammatory activity. Arch Pharm Res 29:617–623PubMedCrossRef

20.

Okuyama E, Hasegawa T, Matsushita T, Fujimoto H, Ishibashi M, Yamazaki M (2001) Analgesic components of saposhnikovia root (Saposhnikovia divaricata). Chem Pharm Bull 49:154–160PubMedCrossRef

21.

Voirin S, Baumes R, Bayonove C (1990) Synthesis and n.m.r. spectral properties of grape monoterpenyl glycosides. Carbohydr Res 207:39–56CrossRef

22.

Otsuka H, Takeda Y, Yamasaki K (1990) Xyloglucosides of benzyl and phenethyl alcohols and Z-hex-3-en-1-ol from leaves of Alangium platanifolium var. trilobum. Phytochemistry 29:3681–3683PubMedCrossRef

23.

Hamerski L, Bomm MD, Silva DHS, Young MCM, Furlan M, Eberlin MN, Castro-Gamboa I, Cavalheiro AJ, da Silva Bolzani V (2005) Phenylpropanoid glucosides from leaves of Coussarea hydrangeifolia (Rubiaceae). Phytochemistry 66:1927–1932PubMedCrossRef

24.

Konishi T, Wada S, Kiyosawa S (1993) Constituents of the leaves of Daphne pseudo-mezereum. Yakugaku Zasshi 113:670–675PubMed

25.

Bisset NG, Choudhury AK, Houghton PJ (1989) Phenolic glycosides from the fruit of Strychnos nux-vomica. Phytochemistry 28:1553–1554CrossRef

26.

Chaurasia N, Wichtl M (1987) Flavonolglykoside aus Urtica dioica. Planta Med 53:432–434PubMedCrossRef

27.

Senatore F, D’Agostino M, Dini I (2000) Flavonoid glycosides of Barbarea vulgaris L. (Brassicaceae). J Agric Food Chem 48:2659–2662PubMedCrossRef

28.

De Rosa S, De Giulio A, Tommonaro G (1996) Aliphatic and aromatic glycosides from the cell cultures of Lycopersicon esculentum. Phytochemistry 42:1031–1034PubMedCrossRef

29.

Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E (2002) Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids. Bioorg Med Chem 10:2133–2142PubMedCrossRef

30.

Fang C-L, Horne S, Taylor N, Rodrigo R (1994) Dimerization of a 3-substituted oxindole at C-3 and its application to the synthesis of (±)-folicanthine. J Am Chem Soc 116:9480–9486CrossRef

31.

Hu F, Lesney PF (1964) The isolation and cytology of two pigment cell strains from B-16 mouse melanomas. Cancer Res 24:1634–1643PubMed

32.

Nakashima S, Matsuda H, Oda Y, Nakamura S, Xu F, Yoshikawa M (2010) Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorg Med Chem 18:2337–2345PubMedCrossRef

33.

Bao K, Dai Y, Zhu Z-B, Tu F-J, Zhang W-G, Yao X-S (2010) Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors. Bioorg Med Chem 18:6708–6714PubMedCrossRef

34.

Parvez S, Kang M, Chung HS, Bae H (2007) Naturally occurring tyrosinase inhibitors: mechanism and applications in skin health, cosmetics and agriculture industries. Phytother Res 21:805–816PubMedCrossRef

35.

Parvez S, Kang M, Chung H-S, Cho C, Hong M-C, Shin M-K, Bae H (2006) Survey and mechanism of skin depigmentating and lightening agents. Phytother Res 20:921–934PubMedCrossRef

36.

Chang T-S (2009) An updated review of tyrosinase inhibitors. Int J Mol Sci 10:2440–2475PubMedCentralPubMedCrossRef

37.

Bertolotto C, Buscá R, Abbe P, Bille K, Aberdam E, Ortonne J-P, Ballotti R (1998) Different cis-acting elements are involved in the regulation of TRP1 and TRP2 promoter activities by cyclic AMP: pivotal role of M boxes (GTCATGTGCT) and of microphthalmia. Mol Cell Biol 18:694–702PubMedCentralPubMed

Title: Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox
Authors: Toshio Morikawa
Yusuke Nakanishi
Kiyofumi Ninomiya
Hisashi Matsuda
Souichi Nakashima
Hisako Miki
Yu Miyashita
Masayuki Yoshikawa
Takao Hayakawa
Osamu Muraoka
Publication date: 01-07-2014
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 3/2014
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-014-0832-1

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Springer Medicine

Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox

Abstract

Keynote webinar | Spotlight on medication adherence

Springer Medicine

Abstract

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