Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells

Nakashima, Souichi; Matsuda, Hisashi; Oda, Yoshimi; Nakamura, Seikou; Xu, Fengming; Yoshikawa, Masayuki

doi:10.1016/j.bmc.2010.01.046

Cited by 80 publications

(73 citation statements)

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“…To develop melanogenesis inhibitors, we have reported the inhibitory effects of several diaryheptanoids and flavonoids in theophylline-stimulated B16 melanoma 4A5 cells recently. 26,27) As a continuing of these studies, the inhibitory effects of the constituents from the roots of P. glomerata on melanogenesis were examined. Among the principal constituents, pfaffianol A (1, IC 50 ϭ44 mM) and pfaffoside C (14, IC 50 ϭ92 mM) substantially inhibited melanogenesis without cytotoxic effects.…”

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confidence: 99%

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

et al. 2010

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The Amaranthaceae plant, Pfaffia (P.) glomerata, which is so-called as Brazil ginseng in Japan, is widely cultivated in South American countries such as Brazil, Ecuador, and Panama. The roots of this plant are used as a Brazilian folk medicine for a tonic and treatment of diabetes. The extract from the roots of P. glomerata has been reported to possess gastroprotective, 2) anti-oxidant, 3) and anti-inflammatory effects.4) On the other hand, ecdysterone has been characterized as the principal constituent from the roots.5,6) However, chemical and pharmacological studies on the roots of P. glomerata have not been investigated sufficiently yet. During the course of characterization studies on the bioactive constituents of Brazilian natural medicines, 1,7-10) the ethyl acetate (EtOAc) and 1-butanol (1-BuOH) soluble fractions of the roots of P. glomerata were found to show inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the EtOAc and 1-BuOH soluble fractions, we have isolated a new noroleanane-type triterpene, pfaffianol A (1), two new noroleanane-type triterpene glycosides, pfaffiaglycosides A (2) and B (3), and three ecdysterone-type sterol glycosides, pfaffiaglycosides C (4), D (5), and E (6), with eight known constituents. Furthermore, we examined the inhibitory effects of the fractions and principal constituents on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. In this paper, we describe the isolation and structure elucidation of the new constituents The ethyl acetate and 1-butanol soluble fractions of the roots of Pfaffia glomerata were found to show inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the ethyl acetate and 1-butanol soluble fractions, we isolated a new noroleanane-type triterpene, pfaffianol A, its glycosides, pfaffiaglycosides A and B, and ecdysterone-type sterol glycosides, pfaffiaglycosides C, D, and E, together with eight known constituents. The structures of new constituents were determined on the basis of physicochemical and chemical evidence. Among them, pfaffianol A (IC 50 ‫؍‬ ‫44؍‬ m mM) and pfaffoside C (IC 50 ‫؍‬ ‫29؍‬ m mM) substantially inhibited melanogenesis without cytotoxic effects. The inhibitory effects were stronger than that of reference compound, arbutin (IC 50 ‫؍‬ ‫471؍‬ m mM).

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confidence: 99%

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

et al. 2010

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“…As shown in Figure 3(A), osthol showed little effect on tyrosinase activity. Melanin synthesis are known to be regulated by melanogenic enzymes such as the tyrosinase-related protein 1 (TRP-1) and TRP-2 as well as tyrosinase (Nakashima et al, 2010;Park et al, 2011). Therefore, the effect of osthol on the expressions of TRP-1, TRP-2, and tyrosinase was determined.…”

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confidence: 99%

Optimization of extraction conditions for osthol, a melanogenesis inhibitor fromCnidium monnierifruits

Kim

Liu

et al. 2016

Pharmaceutical Biology

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Context: Coumarin derivatives have been reported to inhibit melanin biosynthesis. Objective: The melanogenesis inhibitory activity of osthol, a major coumarin of the fruits of Cnidium monnieri Cusson (Umbelliferae), and optimized extraction conditions for the maximum yield from the isolation of osthol from C. monnieri fruits were investigated. Materials and methods: B16F10 melanomas were treated with osthol at concentration of 1, 3, and 10 mM for 72 h. The expression of melanogenesis genes, such as tyrosinase, TRP-1, and TRP-2 was also assessed. For optimization, extraction factors such as extraction solvent, extraction time, and sample/solvent ratio were tested and optimized for maximum yield of osthol using response surface methodology with the Box-Behnken design (BBD). Results: Osthol inhibits melanin content in B16F10 melanoma cells with an IC 50 value of 4.9 mM. The melanogenesis inhibitory activity of osthol was achieved not by direct inhibition of tyrosinase activity but by inhibiting melanogenic enzyme expressions, such as tyrosinase, TRP-1, and TRP-2. The optimal condition was obtained as a sample/solvent ratio, 1500 mg/10 ml; an extraction time 30.3 min; and a methanol concentration of 97.7%. The osthol yield under optimal conditions was found to be 15.0 mg/g dried samples, which were well matched with the predicted value of 14.9 mg/g dried samples. Conclusion: These results will provide useful information about optimized extraction conditions for the development of osthol as cosmetic therapeutics to reduce skin hyperpigmentation. ARTICLE HISTORY

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“…To develop inhibitors of melanogenesis, we have examined the inhibitory effects of several diaryheptanoids, flavonoids, and sterol glycosides in theophylline-stimulated B16 melanoma 4A5 cells. [26][27][28] As a continuation of these studies, the inhibitory effects of constituents from the flowers buds of C. japonica on melanogenesis were examined. Among the isolates, sanchakasaponin B (2, IC 50 =3.1 µM) and sasanquasaponin II (6, IC 50 =2.8 µM) with an acyl group at the 16-or 22-position, substantially inhibited melanogenesis without cytotoxic effects.…”

Section: Structure Of Sanchakasaponins A-d (1-4)mentioning

confidence: 99%

Medicinal Flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese <i>Camellia japonica</i> and their inhibitory effects on melanogenesis<sup>1)</sup>

et al. 2012

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The methanolic extract and its 1-butanol-soluble fraction from the flower buds of Camellia japonica, cultivated in Yunnan Province, China, showed inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the 1-butanol-soluble fraction, a new 28-nor-oleanane-type and three new oleanane-type triterpene saponins, sanchakasaponins A-D, were isolated together with four known triterpene saponins. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells and structure-activity relationships of the saponins were investigated.Key words Camellia japonica; sanchakasaponin; medicinal flower; triterpene oligoglycoside; melanogenesis inhibitorThe Theaceae plant, Camellia japonica L., has been widely cultivated as an ornamental plant in Japan, China, and Taiwan. The flower buds of C. japonica have been used for the treatment of blood stagnation, vomiting of blood and bleeding due to internal and external injury, and also as an anti-inflammatory, tonic, and stomatic in Japanese folk medicine and Chinese traditional medicine. As chemical constituents of this plant, saponins in the fruit and seeds, [2][3][4][5] flavonol glycosides in the leaves, 6) and triterpenes, 7) several hydrolyzable tannins, 8) acylated anthocyanins, 9) and purin alkaloids 10) in the flower have been reported. In the course of our studies on bioactive constituents of the flower buds of Camellia species, we have isolated triterpene saponins from C. sinensis L. (chakasaponins I-VI, floratheasaponins A-J), [11][12][13][14][15][16] C. oleifera ABEL (yuchasaponins A-D), 17) and C. sasanqua THUNB. (sasanquasaponins I-V). 18)Furthermore, antiallergic, antidiabetic, antiobestic, and gastroprotective effects of these saponins have also been reported. Additionally, we have reported the isolation of triterpene saponins, camelliosides A-D, with gastroprotective and platelet-aggregating effects from the flower buds of C. japonica cultivated in Japan. 19,20) As a continuation of our studies on bioactive constituents from the flower buds of C. japonica, we found the methanolic extract and its 1-butanol-soluble fraction of C. japonica cultivated in Yunnan Province, China to have significant inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the 1-butanol-soluble fraction, we have isolated a new 28-nor-oleanane-type triterpene saponin, sanchakasaponin A (1), and three new acylated oleanane-type triterpene saponins, sanchakasaponins B (2), C (3), and D (4), together with four known triterpene saponins (Fig. 1). In this paper, we describe the isolation and structural elucidation, inhibitory effects on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells, and structure-activity relationships of the new triterpene saponins.The methanolic extract (10.0% from the dried flower buds of C. japonica cultivated in Yunnan Province, China) with the inhibitory effect on melano...

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Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells

Cited by 80 publications

References 64 publications

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata

Optimization of extraction conditions for osthol, a melanogenesis inhibitor fromCnidium monnierifruits

Medicinal Flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese <i>Camellia japonica</i> and their inhibitory effects on melanogenesis<sup>1)</sup>

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