Anti‐Tyrosinase Compounds from the Deep‐Sea‐Derived ActinomyceteGeorgeniasp. 40DY180

Abstract

With the aim of finding new marine‐derived skincare promoters, an assay‐guided approach was employed to discover tyrosinase‐modulating compounds from marine actinomycete. Here we describe a new 2,5‐piperazinedione, named georgenione A (1), together with two previously described compounds, 5‐(4’‐hydroxybenzyl)hydantoin (2) and cyclo(Trp‐Gly) (3), produced by actinomycete Georgenia sp. 40DY180, isolated from deep‐sea sediments collected in the Pacific Ocean. Their structures were elucidated by a combination of spectroscopic analyses including 1D and 2D NMR and high‐resolution mass spectrometric data. 5‐(4’‐hydroxybenzyl)hydantoin (2) displayed in vitro potent anti‐tyrosinase activity with IC50 value of 36 μM, comparable to the commercially used positive control kojic acid (IC50=46 μM) and arbutin (IC50=100 μM). Compounds 1–3 were firstly reported from marine actinomycete Georgenia sp.

Identification of a Novel Class of Anti-Melanogenic Compounds, (Z)-5-(Substituted benzylidene)-3-phenyl-2-thioxothiazolidin-4-one Derivatives, and Their Reactive Oxygen Species Scavenging Activities

“…Researchers have devised many strategies to inhibit melanogenesis, such as inhibiting melanosome maturation, melanosome transfer from melanocytes to keratinocytes, and tyrosinase expression or activity [18]. However, interventions that target melanosome maturation and melanosome transfer have unwanted side effects such as burning, swelling, unusual discoloration, itching, and redness [19] and, therefore, research has been primarily directed toward identifying suitable tyrosinase inhibitors [20][21][22][23][24][25][26][27][28]. As a result, several tyrosinase inhibitors (natural, semi-synthetic, and synthetic) have been identified.…”

Marine natural products

“…7 while a new 2,5-piperazinedione analogue, georgenione A 19 was reported from Georgenia sp. 8 Continuing work on Gephyromycinifex aptenodytis derived from the gut microbiota of the Antarctic emperor penguin, Aptenodytes forsteri yielded an additional new angucyclinone analogue, 2-hydroxy-frigocyclinone 20 . 9 An aromatic glycoside 21 was identified from a sediment-derived collection of Nocardiopsis synnemataformans 10 and four new fluvirucin-type macrolactams, fluvirucins B7–B10 22 – 25 were isolated from a sponge-derived rare actinomycete Nonomuraea sp.…”

“…Overall, sediment followed by marine invertebrate collections were the primary sources of new MNP producing bacterial strains. Unique ecological niches such as the deep sea, 5,6,8,67 Mariana Trench, 62 hydrothermal vents, 20,21 and the gut microbiota of the Antarctic emperor penguin 9 were also explored. In 2022, the biosynthetic potential of the open ocean microbiome was assessed by analysing more than 1000 seawater samples which resulted in the identification of over 40 000 putative BGCs, most of which were new, 95 demonstrating there are many new niches and opportunities for new bacterial MNPs to be explored.…”