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

Abstract

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.

Tyrosinase inhibitory activity of supernatant and semi-purified extracts from squid pen fermented with Burkholderia cepacia TKU025

“…H1-7 [14], Aspergillus oryzae BCRC 32288 [3], Myrothecium sp. MFA58 [15], fungus YL185 [16], and the bacterium of Streptomyces roseolilacinus NBRC 12815 [17]. In our screening aimed at isolating tyrosinase inhibitors of microbial origin, we investigated tyrosinase inhibitory activity from the culture supernatant used squid pen as the sole carbon/nitrogen source, and significant activity was found in a strain that was identified as Burkholderia cepacia.…”

Anti-melanogenesis in B16F0 Melanoma Cells by Extract of Fermented Cordyceps militaris Containing High Cordycepin

“…[21] and aspochalasins from solid-state culture of Aspergillus flavipes [9], which potently inhibited melanogenesis in melanocyte cells without cytotoxicity. And potential tyrosinase inhibitors were also produced as secondary metabolites of Streptomyces roseolilacinus NBRC 12815 [24], Aspergillus oryzae KFRI 00875 and 00888 strains [19]. We have also screened melanin biosynthesis inhibitors from the extracts and fermented products and found strong tyrosinase inhibitors using mushroom tyrosinase inhibitory assay in vitro [7,22].…”

In vitro antitrypanosomal activity of 12 low-molecular-weight antibiotics and observations of structure/activity relationships

“…1- 3 We have recently investigated 12 compounds of low-molecular weight, with molecular weights ranging from 219 to 533. The compounds, all known to possess antibiotic properties, are andrastin A, 8-chloro-3¢,4¢,5,7-tetrahydroxyisoflavone (CTI), gliotoxin, gliovirin, isochromophilone I, ochrephilone, lankacidin A, okilactomycin, piloquinone, SF2583A and B (both metabolites of Streptomyces fradiae isolated from marine environments), 4 and thiolutin. In this study, we report the antitrypanosomal profiles of these 12 antibiotics (Figure 1) in comparison with those of two clinically used antitrypanosomal drugs, eflornithine and suramin.…”

“…Recently, Nakashima et al 4 reported that SF2583A (12815A) possesses potent antityrosinase activity, but SF2583B (12815B) does not. They suggested that the chlorine atom in SF2583A plays an important role in bestowing the antityrosinase activity.…”

“…19 Its mode of action in yeast is through inhibition of RNA polymerase. 20 SF2583A (streptochlorin, 12815A) and SF2583 B (12815B) are oxazolyl indole compounds with weak antinematoda, antitumor and antiangiogenic activity, and they also inhibit tumor necrosis factor-a-induced necrosis factor-kB activity and tyrosinase in mushroom and mammalian cells, 4,21,22 although the action mechanism remains unclear. Isochromophilone I and ochrephilone are azaphilone antibiotics.…”