Lupenone and 18α-Oleanan-19α-ol-3-one from Samadera indica

Wintersteiner, O.; Krakower, Gerald W.; Moore, M.

doi:10.1021/jo01019a514

Cited by 7 publications

(2 citation statements)

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“…Recently, natural triterpenoids have received an increased interest in the field of pharmacology, and this is because, at present, more than 100 cytostatic agents are natural triterpenes [55,56]. Lupenone can be isolated from many plants [26][27][28][29], and this report shows that it can also be found in a Mediterranean plant E. multiflora. Reports on the effects of lupenone include protein tyrosine phosphatase 1B inhibition [57], among several bioactivities.…”

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confidence: 82%

“…Previously, E. multiflora extract was reported to promote human dermal papilla cells in vitro and in vivo by induction of the anagen phase from the telogen phase [25]. Lupenone has been reported to be present in many plants including Sorbus commixta [26], Samadera indica [27], yellow birch [28], and Tephrosia villosa [29], but there have been no reports on its presence in E. multiflora. In this study, the effect of E. multiflora leaf extract on melanogenesis in B16 melanoma cells and the mechanism underlying these effects were investigated.…”

Section: ! α-Mshmentioning

confidence: 99%

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Lupenone from Erica multiflora Leaf Extract Stimulates Melanogenesis in B16 Murine Melanoma Cells through the Inhibition of ERK1/2 Activation

et al. 2013

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Hypopigmentation diseases are usually managed using UVB light which increases the patients' risk for skin cancer. Here, we evaluated the melanogenesis stimulatory effects of leaf extracts of Erica multiflora, a medicinal plant from the Mediterranean region, and its active component, lup-20(29)-en-3-one, as possible therapeutic agents to address hypopigmentation disorders. B16 murine melanoma cells were treated with E. multiflora extracts or its active component lupenone to evaluate their effects on melanin biosynthesis. The mechanism underlying the observed effects was also determined. Bioactivity-guided fractionation of fifteen ethyl acetate fractions identified fraction 2 to have melanogenesis stimulatory effects due to its ability to decrease mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 activation. Preparative TLC of ethyl acetate fraction 2 revealed the presence of lup-20(29)-en-3-one as the major bioactive component. B16 cells treated with lup-20(29)-en-3-one increased melanin content without cytotoxicity. To determine the mechanism for the observed effects of lup-20(29)-en-3-one, the tyrosinase enzyme activity, the tyrosinase protein expression, and the activation of phosphorylated extracellular signal-regulated kinases 1 and 2 were determined. In addition, the expression of the tyrosinase mRNA was quantified using real-time PCR. Results showed that lup-20(29)-en-3-one has no effect on the tyrosinase enzyme activity but can increase tyrosinase expression at both the transcriptional and translational levels. The increase in the tyrosinase mRNA expression was most likely due to the inhibited mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 activation. We report for the first time that E. multiflora ethyl acetate extract and its active compound lup-20(29)-en-3-one stimulate melanogenesis by increasing the tyrosinase enzyme expression via mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 phosphorylation inhibition, making it a possible treatment for hypopigmentation diseases.

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