New piericidin glucosides, glucopiericidins A and B.

Abstract

The new piericidin group antibiotics, glucopiericidins A and B were isolated from the culture broth of Streptomyces pactum S48727 (FERMP-8117) as co-metabolite of piericidin Ai.The structures of glucopiericidins A and B were determined as piericidin Al9 10-O-fi-Dglucoside and piericidin Al9 3'-0-D-glucoside on the basis of their spectral and chemical properties , respectively.Glucopiericidins were more potent in inhibiting antibody formation than piericidin Ai in vitro. In addition, these substances showedbetter antimicrobial activities than piericidin AÂ cute toxicities of these substances in mice were lower than that of piericidin Ax. This indicates that D-glucose in glucopiericidin molecules is important in modulating their physiological activities.In the course of a screening for physiologically active substances, a strain of actinomycetes, S48727, was shown to produce new piericidin glucosides, glucopiericidins A and B in addition to the known antibiotic piericidin A^K They showed antimicrobial activity and in vitro inhibitory activity against antibody formation. This paper reports the taxomony of the producing organism and the fermentation, the isolation, structures and biological properties of glucopiericidins A and B.Taxonomy

An NF-κB-Based High-Throughput Screen Identifies Piericidins as Inhibitors of the Yersinia pseudotuberculosis Type III Secretion System

“…We identified one compound as the piericidin derivative Mer-A 2026B and the other as piericidin A1 (22)(23)(24). Piericidins have previously characterized activity as insecticides, vasodilators, and inhibitors of the mitochondrial NADH dehydrogenase and as general antibiotics against certain bacteria (22,23,(25)(26)(27).…”

Glucopiericidin C: a cytotoxic piericidin glucoside antibiotic produced by a marine Streptomyces isolate

“…Among them, glucopiericidin A (1), B and some others display antimicrobial properties and in vitro inhibitory activity against antibody formation. 5 For glucopiericidiols A1 and A2, additional cytocidal activities against HeLa S3 cells in vitro have been reported, 6 and others demonstrate insecticidal activity. 7 The biological activities of the glucopiericidins are strongly influenced by the structure and position of the sugar unit: glucopiericidins A (1) and B show higher antimicrobial activities than piericidin A (2) or other glycosides such as 3¢-rhamnopiericidin A1 (SN-198-C), 8 3¢-deoxytalopiericidin A1 (DTPA) 9 and 7-demethyl-3¢-rhamnopiericidin A1.…”

“…10 In contrast, acute toxicities of the latter three substances in mice were lower than those of piericidin A (2). 5 In our search for new secondary metabolites from marine bacteria, we isolated a new cytotoxic piericidin derivative, glucopiericidin C (3), and for the first time as natural product, 5-oxo-5-o-tolyl-pentanoic acid (8a) together with further 10 known metabolites. The algal metabolite spatozoate (6) was isolated here for the first time from bacteria.…”

A new 16-membered tetraene macrolide JBIR-100 from a newly identified Streptomyces species

“…The anomeric proton of the sugar system in 184 was downfield shifted to δ 4.80, due to its attachment to the aromatic residue. On the other hand, the corresponding anomeric proton in 183 is upfield shifted (δ 4.20, literature: 4.13) [288,290] as it is attached to an sp 3 system (Table 23) Glucopiericidin A (183) was found to inhibit antibody formation [288] , and it was discovered to have antihypertensive properties. Furthermore, it exhibited cytotoxic activity against L5178Y cell cultures, and cytocidal activities against HeLa S 3 cells in vitro.…”

“…Additionally, it showed an activity against the micro algae Chlorella vulgaris (Table 68). [288,290] Glucopiericidin A (183) Exp. (Table 24).…”