Antaroide, a Novel Natural Nine-Membered Macrolide, Inhibits Melanin Biosynthesis in B16F10 Murine Melanoma Cells

Abstract

The demand for natural substances with anti-melanogenic activity is increasing due to the recent interest in skin whitening. Intensive investigation on the culture broth of Streptomyces sp. SCO-736, a marine bacterium from the Antarctica coast, has led to the isolation of a new natural product named antaroide (1). The chemical structure was established through the interpretation of MS, UV, and NMR spectroscopic data. Antaroide is a nine-membered macrolide with lactone and lactam moieties. To investigate its applicability in skin whitening cosmetics, its anti-melanogenic activity in B16F10 murine melanoma cells was examined. As a result, antaroide displayed strong inhibitory activities against melanin synthesis and also attenuated the dendrite formation induced by the α-melanocyte stimulating hormone (α-MSH). Antaroide suppressed the mRNA expression of the melanogenic enzymes such as tyrosinase, TRP-1 and TRP-2. This suggests that it may serve as a transcriptional regulator of melanogenesis. Collectively, the discovery of this novel natural nine-membered macrolide and its anti-melanogenic activity could give new insights for the development of skin whitening agents.

Camellia japonica Essential Oil Inhibits α-MSH-Induced Melanin Production and Tyrosinase Activity in B16F10 Melanoma Cells

“…e etiology of pigmentation is not well understood. Melanin biosynthesis is catalyzed by melanocyte-specific enzymes such as TRP-1 and TRP-2 [34]. Tyrosinase is vital to melanocyte melanin biosynthesis and has been known for many decades [34].…”

“…Melanin biosynthesis is catalyzed by melanocyte-specific enzymes such as TRP-1 and TRP-2 [34]. Tyrosinase is vital to melanocyte melanin biosynthesis and has been known for many decades [34]. erefore, tyrosinase is an important index for the treatment of pigmentation.…”

Marine natural products

“…45 Two antibiotic dixiamycins 138 and 139 from Streptomyces olivaceus displayed activities against seven bacterial strains ranging from potent to no antibacterial activity. 46 Other Streptomyces strains yielded antaroide 140, a new nine-membered macrolide that was shown to inhibit melanin biosynthesis in murine melanoma cells, 47 Genome sequencing of this strain revealed the presence of a BGC that encoded for glycosylated type I PKS and additional studies showed that the BGC associated with venturicidin biosynthesis (ven) was supported by the proposed biosynthetic pathway and conrmed by inactivation of the core PKS gene venK. 68 As with previous reviews in this series, a number of new bacterial MNPs were claimed during 2021, but the structures presented were not fully consistent with the spectroscopic evidence provided.…”

“…45 Two antibiotic dixiamycins 138 and 139 from Streptomyces olivaceus displayed activities against seven bacterial strains ranging from potent to no antibacterial activity. 46 Other Streptomyces strains yielded antaroide 140 , a new nine-membered macrolide that was shown to inhibit melanin biosynthesis in murine melanoma cells, 47 two antibacterial pyrrolobenzodiazepine derivatives 141 and 142 , 48 a new polycyclic tetramate macrolactam, koyanamide A 143 , 49 a new butenolide derivative 144 , featuring an octyl substitution at the γ-position, 50 two angucyclinone derivatives, gephyyamycin 145 and cysrabelomycin 146 , 51 and TMKS8A 147 , a new antibacterial chlorinated α-lapachone derivative, that was identified from the culture extract of a Streptomyces strain that was obtained from a sea slug. 52 Marinoterpins A–C 148 , 149 and 150 were isolated from the culture broth extracts of two actinomycetes associated with the family Streptomycetaceae and represent new chemical motifs as they combine quinoline- N -oxides with linear sesterterpenoid side chains.…”

Effect of hydrosol obtained from Camellia japonica branch on α-MSH-induced melanin and tyrosinase activity in B16F10 melanoma cells

“…The etiology of pigmentation remains relatively enigmatic. The cascade of melanin biosynthesis hinges on melanocyte-specific enzymes such as TRP-1 and TRP-2 (Ryu et al 2021). Hence, tyrosinase emerges as a pivotal gauge in addressing pigmentation concerns.…”