A Novel Melanin Inhibitor: Hydroperoxy Traxastane-Type Triterpene from Flowers of Arnica montana

Maeda, Kazuhisa; Naitou, Tomoko; Umishio, Kenichi; Fukuhara, Tadao; Motoyama, Akira

doi:10.1248/bpb.30.873

Cited by 30 publications

(20 citation statements)

References 24 publications

(51 reference statements)

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“…4). Several other melanin biosynthesis inhibitors that do not inhibit tyrosinase activity have been isolated from plants; these include 3b,16b-dihydroxy-21a-hydroperoxy-20(30)-taraxastene (IC 50 ϭ0.04 mM) from Arnica Montana, 27) 4,5-dihydrozy-3-propenyl-2-cyclopenten-1-one (terrein; IC 50 ϭ30 mM) from Penicillium species, 30) piperlonguminine (IC 50 ϭ10 mM) from Piper longum (Piperaceae), 31) and coumarin compounds such as soimperatorin and imperatorin (IC 50 Ͼ100 mM) from Angelica dahurica. 32) Thus, (2Z,8Z)-matricaria acid methyl ester is a potent melanin biosynthesis inhibitor isolated from plants.…”

Section: Discussionmentioning

confidence: 99%

Depigmentation of Melanocytes by (2Z,8Z)-Matricaria Acid Methyl Ester Isolated from Erigeron breviscapus

Luo

Kim

Nguyen

et al. 2009

Biological & Pharmaceutical Bulletin

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To discover an active skin depigmenting agent, we isolated a novel inhibitor of melanin biosynthesis from the methanol extract of Erigeron breviscapus using a bioactivity-guided fractionation and identified it as (2Z,8Z)-matricaria acid methyl ester by means of spectroscopic analysis. The compound showed strong whitening activity in melan-a cell. Compared with arbutin (IC 50 ‫0.4؍‬ mM) as a positive control, the depigmentation IC 50 value for (2Z,8Z)-matricaria acid methyl ester was 25.4 m mM in B16F10 melanoma cell. Moreover, its inhibitory effect on tyrosinase, the key enzyme of melanogenesis, was examined by in vivo and in vitro tyrosinase assay and Western blot. The results indicate that (2Z,8Z)-matricaria acid methyl ester isolated from Erigeron breviscapus is a promising compound that could be useful for treating hyper-pigmentation as skin-whitening agents.Key words melanin; Erigeron breviscapus; (2Z,8Z)-matricaria acid methyl ester; skin whitening Biol.

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Section: Discussionmentioning

confidence: 99%

Depigmentation of Melanocytes by (2Z,8Z)-Matricaria Acid Methyl Ester Isolated from Erigeron breviscapus

Luo

Kim

Nguyen

et al. 2009

Biological & Pharmaceutical Bulletin

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“…Another compound of this type 461 were obtained from Arnica montana. 273 The rhizome of Vladimiria muliensis provided one antimicrobial ursane triterpenoid 1α,5α-dioxy-11α-hydroxyurs-12-en-3-one 462. 274 Other ursene triterpenoids were including 3β,28-dihydroxy-11α-hydroperoxy-12-ursene 463 from Tolpis proustii, 275 speciosaperoxide 464 from Chaenomeles speciosa, 276 and (2β,3β)-3,25-epidioxy-2,24-dihydroxyursa-12,20(30)-dien-28-oic acid 465 and (2β,3β)-3,25-epidioxy-2,24-dihydroxyurs-12-en-28-oic acid 466 from Gentiana aristata.…”

Section: Triterpenesmentioning

confidence: 99%

Peroxy natural products

Liu

2013

Nat. Prod. Bioprospect.

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“…The melanin content in B16 melanoma cells was determined as described previously 18) with a minor modification. The B16 melanoma cells were cultured continuously in DMEM medium containing 10% FBS and aMSH (10 ng/ml) for 3 d in the presence of 12815A (at final concentrations of 6.25, 12.5, 25, 50, and 100 mM) or kojic acid (at a final concentration of 300 mM).…”

Section: Methodsmentioning

confidence: 99%

Physicochemical Characters of a Tyrosinase Inhibitor Produced by Streptomyces roseolilacinus NBRC 12815

Nakashima

Anzai

Kuwahara

et al. 2009

Biological & Pharmaceutical Bulletin

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We examined the biological activities present in Streptomyces strains preserved at the National Institute of Technology and Evaluation Biological Resource Center, and found a metabolite of Streptomyces roseolilacinus NBRC 12815 that showed a potent anti-tyrosinase activity. The compounds with anti-tyrosinase activity were purified by several chromatographic procedures. Final HPLC analysis revealed at least two anti-tyrosinase compounds with different retention times (12815A and B). The identification of two anti-tyrosinase compounds was performed with instrumental analysis and database search. The results obtained suggest that the active compounds are SF 2583A and B. Compound 12815A (IC 50 values; about 9 m mM) showed more potent tyrosinase inhibition than compound 12815B (IC 50 values; about 1086 m mM). The only structural difference between 12815A and B is the presence of an additional chloric atom. In addition, the activity of 12815A was markedly decreased under acidic conditions, resulting in irreversible inactivation. However, the inactivated 12815A still exhibited residual activity when exposed to detergent, Tween 80. These results suggest that the chlorine and the hydration water are very important in the exertion of anti-tyrosinase activity by 12815A.

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A Novel Melanin Inhibitor: Hydroperoxy Traxastane-Type Triterpene from Flowers of Arnica montana

Cited by 30 publications

References 24 publications

Depigmentation of Melanocytes by (2Z,8Z)-Matricaria Acid Methyl Ester Isolated from Erigeron breviscapus

Depigmentation of Melanocytes by (2Z,8Z)-Matricaria Acid Methyl Ester Isolated from Erigeron breviscapus

Peroxy natural products

Physicochemical Characters of a Tyrosinase Inhibitor Produced by Streptomyces roseolilacinus NBRC 12815

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