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Journal of Natural Medicines

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01.01.2016 | Original Paper

Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis

verfasst von: Toshio Morikawa, Kiyofumi Ninomiya, Hiroyuki Kuramoto, Iyori Kamei, Masayuki Yoshikawa, Osamu Muraoka

Erschienen in: Journal of Natural Medicines | Ausgabe 1/2016

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Abstract

A methanol extract of the flowers of Narcissus tazetta var. chinensis Roem. (Amaryllidaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the extract, four new phenylethanoid glycosides, tazettosides A–D (1–4), and a new phenylpropanoid glycoside, tazettoside E (5), were isolated along with 23 known compounds (6–28). Of the isolates, 1 (IC₅₀ = 22.0 μM) and 4 (82.5 μM), 3-methoxy-8,9-methylenedioxy-3,4-dihydrophenanthridine (13, IC₅₀ = 28.5 μM), 5,6-dihydrobicolorine (14, 23.7 μM), tazettine (16, 60.8 μM), benzyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (18, 27.8 μM), 2-(3,4-dimethoxyphenyl)ethyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (21, 74.6 μM), 3-phenylpropyl β-D-glucopyranoside (22, 59.0 μM), and cinnamyl β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (24, 88.0 μM) showed inhibitory effects without notable cytotoxicity at the effective concentrations.

Fu K-L, Shen Y-H, Lu L, Li B, He Y-R, Li B, Yang X-W, Su J, Liu R-H, Zhang W-D (2013) Two unusal rearranged flavan derivatives from Narcissus tazetta var. chinensis. Helv Chim Acta 96:338–344CrossRef

Chen H-C, Chi H-S, Lin L-Y (2013) Headspace solid-phase microextraction analysis of volatile components in Narcissus tazetta var. chinensis Roem. Molecules 18:13723–13734CrossRefPubMed

Tomoda M, Yokoi-Arai M, Torigoe A, Maru K (1980) Plant mucilages. XXVII. isolation and characterization of a mucous polysaccharide, “narcissus-T-glucomannan”, from the bulbs of Narcissus tazetta var. chinensis. Chem Pharm Bull 28:3251–3257CrossRef

Ma G-E, Li H-Y, Lu C-E, Yang X-M, Hong S-H (1986) 6α/6β-Hydroxy-3-O-methylepimaritidine, two new alkaloids from Narcissus tazetta L. var. chinensis Roem. Heterocycles 24:2089–2092CrossRef

Morikawa T, Wang L-B, Nakamura S, Ninomiya K, Yokoyama E, Matsuda H, Muraoka O, Wu L-J, Yoshikawa M (2009) Medicinal flowers. XXVII. new flavone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-α inhibitors from everlasting, flowers of Helichrysum arenarium. Chem Pharm Bull 57:361–367CrossRefPubMed

Morikawa T, Xie H, Wang T, Matsuda H, Yoshikawa M (2009) Acylated flavonol bisdesmosides, sinocrassosides A₃–A₇ and B₃, with aminopeptidase N inhibitory activity from Sinocrassula indica. Chem Biodiv 6:411–420CrossRef

Wang L-B, Morikawa T, Nakamura S, Ninomiya K, Matsuda H, Muraoka O, Wu L-J, Yoshikawa M (2009) Medicinal flowers. XXVIII. Structures of five new glycosides, everlastosides A, B, C, D, and E, from the flowers of Helichrysum arenarium. Heterocycles 78:1235–1242CrossRef

Morikawa T, Wang L-B, Ninomiya K, Nakamura S, Matsuda H, Muraoka O, Wu L-J, Yoshikawa M (2009) Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium. Chem Pharm Bull 57:853–859CrossRefPubMed

Morikawa T, Li X, Nishida E, Makamura S, Ninomiya K, Matsuda H, Oda Y, Muraoka O, Yoshikawa M (2010) Medicinal flowers part 29. Acylated oleanane-type triterpene bisdesmosides: perennisaponins G, H, I, J, K, L, and M with pancreatic lipase inhibitory activity from the flowers of Bellis perennis. Helv Chim Acta 93:573–586CrossRef

10.

Morikawa T, Muraoka O, Yoshikawa M (2010) Pharmaceutical food science: search for anti-obese constituents from medicinal foods—anti-hyperlipidemic saponin constituents from the flowers of Bellis perennis. Yakugaku Zasshi 130:673–678CrossRefPubMed

11.

Morikawa T, Li X, Nishida E, Nakamura S, Ninomiya K, Matsuda H, Hamao M, Muraoka O, Hayakawa T, Yoshikawa M (2011) Medicinal flowers. XXXII. Structures of oleanane-type triterpene saponins, perennisosides VIII, IX, X, XI, and XII, from the flowers of Bellis perennis. Chem Pharm Bull 59:889–895CrossRefPubMed

12.

Morikawa T, Imura K, Miyake S, Ninomiya K, Matsuda H, Yamashita C, Muraoka O, Hayakawa T, Yoshikawa M (2012) Promoting the effect of chemical constituents from the flowers of Poaynum hendersonii on adipogenesis in 3T3-L1 cells. J Nat Med 66:39–48CrossRefPubMed

13.

Morikawa T, Miyake S, Miki Y, Ninomiya K, Yoshikawa M, Muraoka O (2012) Quantitative analysis of acylated oleanane-type triterpene saponins, chakasaponins I-III and floratheasaponins A–F, in the flower buds of Camellia sinensis from different regional origins. J Nat Med 66:608–613CrossRefPubMed

14.

Morikawa T, Sueyoshi M, Chaipech S, Matsuda H, Nomura Y, Yabe M, Matsumoto T, Ninomiya K, Yoshikawa M, Pongpiriyadacha Y, Hayakawa T, Muraoka O (2012) Suppressive effects of coumarins from Mammea siamensis on inducible nitric oxide synthase expression in RAW264.7 cells. Bioorg Med Chem 20:4968–4977CrossRefPubMed

15.

Morikawa T, Ninomiya K, Miyake S, Miki Y, Okamoto M, Yoshikawa M, Muraoka O (2013) Flavonol glycosides with lipid accumulation inhibitory activity and simultaneous quantitative analysis of 15 polyphenols and caffeine in the flower buds of Camellia sinensis from different regions by LCMS. Food Chem 140:353–360CrossRefPubMed

16.

Morikawa T, Lee I-J, Okugawa S, Miyake S, Miki Y, Ninomiya K, Kitagawa N, Yoshikawa M, Muraoka O (2013) Quantitative analysis of catechin, flavonoid, and saponin constituents in “tea flower”, the flower buds of Camellia sinensis, from different regions in Taiwan. Nat Prod Commun 8:1553–1557PubMed

17.

Morikawa T, Nakanishi Y, Ninomiya K, Matsuda H, Nakashima S, Miki H, Miyashita Y, Yoshikawa M, Hayakawa T, Muraoka O (2014) Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus oraecox. J Nat Med 68:539–549CrossRefPubMed

18.

Sakamoto A, Tanaka Y, Yamada T, Kikuchi T, Muraoka O, Ninomiya K, Morikawa T, Tanaka R (2015) Andirolides W–Y from the flower oil of andiroba (Carapa guianensis, Meliaceae). Fitoterapia 100:81–87CrossRefPubMed

19.

Morikawa T, Ninomiya K, Takamori Y, Nishida E, Yasue M, Hayakawa T, Muraoka O, Li X, Nakamura S, Yoshikawa M, Matsuda H (2015) Oleanane-type triterpene saponins with collagen synthesis-promoting activity from the flowers of Bellis perennis. Phytochemistry 116:203–212CrossRefPubMed

20.

Morikawa T, Ninomiya K, Akaki J, Kakihara N, Kuramoto H, Matsumoto Y, Hayakawa T, Muraoka O, Wang L-B, Wu L-J, Nakamura S, Yoshikawa M, Matsuda H (2015) Dipeptidyl peptidase-IV inhibitory activity of dimeric dihydrochalcone glycosides from flowers of Helichrysum arenarium. J Nat Med 69:494–506CrossRefPubMed

21.

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

22.

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

23.

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

24.

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

25.

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 207:33–40CrossRefPubMed

26.

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

27.

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

28.

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

29.

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

30.

Flamini G, Antognoli E, Morelli I (2001) Two flavonoids and other compounds from the aerial parts of Centaurea bracteata from Italy. Phytochemistry 57:559–564CrossRefPubMed

31.

Xie H, Wang T, Matsuda H, Morikawa T, Yoshikawa M, Tani T (2005) Bioactive constituents from Chinese natural medicines. XV. Inhibitory effects on aldose reductase and structures of saussureosides A and B from Saussurea medusa. Chem Pharm Bull 53:1416–1422CrossRefPubMed

32.

Merina AJ, Kesavan D, Sulochana D (2011) Isolation and antihyperglycemic activity of flavonoids from flower of Opuntia stricta. Pharm Chem J 45:317–321CrossRef

33.

Fukunaga T, Kajikawa I, Nishiya K, Watanabe Y, Suzuki N, Takeya K, Itokawa H (1988) Studies on the constituents of the European mistletoe, Viscum album L. II. Chem Pharm Bull 36:1185–1189CrossRef

34.

Sarikaya BB, Zencir S, Somer NU, Kaya GI, Onur A, Bastida J, Bereenyi A, Zupko I, Topcu Z (2012) The effects of arolycoricidine and narciprimine on tumor cell killing and topoisomerase activity. Rec Nat Prod 6:381–385

35.

Viladomat F, Sellés M, Codina C, Bastida J (1997) Alkaloids from Narcissus asturiensis. Planta Med 63:583CrossRefPubMed

36.

Sanz R, Fernández Y, Castroviejo MP, Pérez A, Fañanás FJ (2007) Functionalized phenanthridine and dibenzopyranose derivatives through benzyne cyclization—application to the total synthesis of trisphaeridine and N-methylcrinasiadine. Eur J Org Chem 2007:62–69CrossRef

37.

Hohmann J, Forgo P, Szabó P (2002) A new phenanthridine alkaloid from Hymenocallis × festalis. Fitoterapia 73:749–751CrossRefPubMed

38.

Viladomat F, Bastida J, Tribo G, Codina C, Rubiralta M (1990) Alkaloids from Narcissus bicolor. Phytochemistry 29:1307–1310CrossRef

39.

Kobayashi S, Kihara M, Shingu T, Shingu K (1980) Transformation of tazettine to pretazettine. Chem Pharm Bull 28:2924–2932CrossRef

40.

Rigby JH, Cavezza A, Heeg MJ (1998) Total synthesis of (±)-tazettine. J Am Chem Soc 120:3664–3670CrossRef

41.

Miyase T, Ueno A, Takizawa N, Kobayashi H, Karasawa H (1987) Studies on the glycosides of Epimedium grandiflorum Morr. var. thunbergianum (Miq.) Nakai. I. Chem Pharm Bull 35:1109–1117CrossRef

42.

Morikawa T, Nakamura S, Kato Y, Muraoka O, Matsuda H, Yoshikawa M (2007) Bioactive saponins and glycosides. XXVIII. New triterpene saponins, foliatheasaponins I, II, III, IV, and V, from Tencha (the leaves of Camellia sinensis). Chem Pharm Bull 55:293–298CrossRefPubMed

43.

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

44.

Piao MS, Kim M-R, Lee DG, Park Y, Hahm K-S, Moon Y-H, Woo E-R (2003) Antioxidative constituents from Buddleia officinalis. Arch Pharm Res 26:453–457CrossRefPubMed

45.

Han X, Zhang T, Wei Y, Cao X, Ito Y (2002) Separation of salidroside from Rhodiola crenulata by high-speed counter-current chromatography. J Chromatogr A 971:237–241CrossRefPubMed

46.

Morikawa T, Pan Y, Ninomiya K, Imura K, Matsuda H, Yoshikawa M, Yuan D, Muraoka O (2010) Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa. Bioorg Med Chem 18:1882–1890CrossRefPubMed

47.

Çalis I, Tasdemir D, Sticher O, Nishibe S (1999) Phenylethanoid glycosides from Digitalis ferruginea subsp. ferruginea (=D. aurea Lindley) (Scrophulariaceae). Chem Pharm Bull 47:1305–1307CrossRef

48.

Kurashima K, Fujii M, Ida Y, Akita H (2004) Simple synthesis of β-D-glycopyranosides using β-glycosidase from almonds. Chem Pharm Bull 52:270–275CrossRefPubMed

49.

Tolonen A, György Z, Jalonen J, Neubauer P, Hohtola A (2004) LC/MS/MS identification of glycosides produced by biotransformation of cinnamyl alcohol in Rhodiola rosea compact callus aggregates. Biomed Chromatogr 18:550–558CrossRefPubMed

50.

Mohamed KM, Mohamed MH, Ohtani K, Kasai R, Yamasaki K (1999) Megastigmane glycosides from seeds of Trifolium alexandrinum. Phytochemistry 50:859–862CrossRef

51.

Otsuka H, Yao M, Kamada K, Takeda Y (1995) Alangionosides G–M: glycosides of megastigmane derivatives from the leaves of Alangium premnifolium. Chem Pharm Bull 43:754–759CrossRefPubMed

52.

Tanabe G, Sugano Y, Shirato M, Sonoda N, Tsutsui N, Morikawa T, Ninomiya K, Yoshikawa M, Muraoka O (2015) Total synthesis of 4,5-didehydroguadiscine: a potent melanogenesis inhibitor from the Brazilian medicinal herb, Hornschuchia oblique. J Nat Prod 78:1536–1542CrossRefPubMed

53.

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

54.

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 18:6708–6714CrossRefPubMed

55.

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

56.

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

57.

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

Titel: Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var. chinensis
verfasst von: Toshio Morikawa
Kiyofumi Ninomiya
Hiroyuki Kuramoto
Iyori Kamei
Masayuki Yoshikawa
Osamu Muraoka
Publikationsdatum: 01.01.2016
Verlag: Springer Japan
Erschienen in: Journal of Natural Medicines / Ausgabe 1/2016
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-015-0941-5

Springer Medizin

Abstract

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