Melanogenesis‐Inhibitory Activity of Aromatic Glycosides from the Stem Bark of <i>Acer buergerianum</i>

Akihisa, Toshihiro; Orido, Masashi; Akazawa, Hiroyuki; Takahashi, Akitomo; Yamamoto, Ayako; Ogihara, Eri; Fukatsu, Makoto

doi:10.1002/cbdv.201200251

Cited by 9 publications

(1 citation statement)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Daphnetin has been known to possess notable therapeutic properties against malaria, allergy, inflammatory disorders, and malignant tumors [ 28 , 29 , 30 ]. In addition, (−)-lariciresinol, (+)-pinoresinol, and (−)-wikstromol are known to be potential MITF inhibitors [ 31 ]. Therefore, DOE may have strong anti-melanogenesis activity due to the presence of several constituents of melanogenesis inhibitors, including daphnetin, although we do not know the exact identity of the constituent that exerts the anti-melanogenic effect, and it is not clear whether the constituents exhibit the anti-melanogenic effect individually or collectively [ 32 ].…”

Section: Discussionmentioning

confidence: 99%

Daphne odora Exerts Depigmenting Effects via Inhibiting CREB/MITF and Activating AKT/ERK-Signaling Pathways

Eom

Jeong

Ryu

et al. 2022

CIMB

View full text Add to dashboard Cite

Daphne odora, a blooming shrub, has been traditionally used for various medicinal purposes. However, information on its anti-melanogenic activity and dermal application is limited. In this study, the Daphne odora extract (DOE), with constituents including daphnetin, was used to investigate depigmenting activity and the underlying mechanism of Daphne odora. DOE inhibited in vitro and cellular tyrosinase activity in a dose-dependent manner, and reduced the α-MSH-induced melanin biosynthesis to a control level. The protein expressions of melanin synthesis-related enzymes were also significantly reduced by DOE. Moreover, DOE decreased the phosphorylation of cAMP-response element binding proteins (CREBs) induced by α-MSH in B16F10 cells, while it activated phosphorylated extra-cellular signal-regulated kinases (ERKs) and protein kinase B (AKT) expression. These results suggest that DOE might inhibit the melanogenesis signaling pathways by activating ERK- and AKT-signaling pathways to regulate the expression of CREB and MITF and its downstream pathways. Therefore, DOE could potentially be developed as a depigmenting agent.

show abstract

Section: Discussionmentioning

confidence: 99%

Daphne odora Exerts Depigmenting Effects via Inhibiting CREB/MITF and Activating AKT/ERK-Signaling Pathways

Eom

Jeong

Ryu

et al. 2022

CIMB

View full text Add to dashboard Cite

show abstract

Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis

Zhang

Koike

Yamamoto

et al. 2013

Chemistry & Biodiversity

View full text Add to dashboard Cite

A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.3-47.2% reduction of melanin content with no, or almost no, toxicity to the cells (90.8-100.2% cell viability) at 100 μM. Western blot analysis showed that compound 2 reduced the protein levels of MITF, TRP-1, and tyrosinase, in a concentration-dependent manner while exerted almost no influence on the level of TRP-2, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of TRP-1 and tyrosinase. In addition, compounds 1-17 were evaluated for their inhibitory effects against the EpsteinBarr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells.

show abstract

Melanogenesis‐Inhibitory Activities of Isomeric C‐seco Limonoids and Deesterified Limonoids

Akihisa¹,

Horiuchi

Matsumoto

et al. 2016

Chemistry & Biodiversity

View full text Add to dashboard Cite

Treatment of eight C-seco limonoids including six of salannin-type, 1 - 6, and two of nimbin-type, 7 and 8, with a combination of BF · Et O and iodide ion yielded the isomeric C-seco derivatives, i.e., six isosalannins, 1a - 6a, and two isonimbins, 7a and 8a, respectively. Ohchinin (1) was further subjected to LiAlH reduction which yielded a deesterified trihydroxy limonoid, nimbidinol (9). In addition, ten limonoids including seven of azadirone-type, 10 - 16, and three of gedunin-type, 17 - 19, all of which possess no ester functionality in the molecule, were obtained from the neutral fraction of Azadirachta indica seed extract after alkaline hydrolysis. Among the above, twelve compounds, i.e., 1a - 4a, 6a, 9, 13 - 16, 18, and 19, were new compounds, and their structures were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of all these limonoids for their inhibitory activities against melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), five structurally modified limonoids, 3-deacetyl-28-oxosalannin (6a), 9, 17-epi-17-hydroxynimbocinol (14), 17-epi-17-hydroxy-15-methoxynimbocinol (15), and 7-deacetyl-17-epinimolicinol (18), in addition to a natural limonoid, 1, exhibited potent inhibitory activities with 26 - 66% reduction of melanin content at 100 μm concentration with almost no or low toxicity to the B16 melanoma cells (70 - 99% cell viability at 100 μm).

show abstract

Melanogenesis‐Inhibitory Activity of Aromatic Glycosides from the Stem Bark of Acer buergerianum

Cited by 9 publications

References 34 publications

Daphne odora Exerts Depigmenting Effects via Inhibiting CREB/MITF and Activating AKT/ERK-Signaling Pathways

Daphne odora Exerts Depigmenting Effects via Inhibiting CREB/MITF and Activating AKT/ERK-Signaling Pathways

Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis

Melanogenesis‐Inhibitory Activities of Isomeric C‐seco Limonoids and Deesterified Limonoids

Contact Info

Product

Resources

About