Isolation Structure and Physiological Activities of Piericidin B, Natural Insecticide Produced by a Streptomyces

Abstract

Piericidin B was isolated from mycellia of Streptomyces mobaraensis besides piericidin A. On the basis of IR, NMR and mass spectral studies together with chemical evidences, its structure was assigned as Id. Its physiological activities are also deescribd.

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

“…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).…”

The unique chemistry and biology of the piericidins

“…Boger and co-workers were also successful in accessing the C-5′-desmethyl and C-4′-deshydroxy-C-5′-desmethyl analogues bearing the natural piericidin side chain as well as the simplified farnesyl side chain, 5′-desmethylpiericidin A1 (61), 4′-deshydroxy-5′-desmethylpiericidin A1 (62) and the corresponding farnesyl side-chain bearing analogues (63, 64; Figure 6). …”

“…Piericidins were first discovered because of their insecticidal activity, 3,62 and mechanistic studies indicated that complex I was the molecular target of piericidins. 63 Besides its well-known redox role in the electron transport chain, complex I is also considered to be one of the main production sites of reactive oxygen species (ROS).…”

The Structural Revision of Piericidin A by Combination of CMR Spectroscopic and Biosynthetic Studies

“…The structural revision of PA means that the structure of PB is also revised as (lIb) because PA has been converted to PB methylation. 2 ) The combination studies of CMR spectroscopy and l3C-feeding experiments enabled us to assign Sp2 carbons in the fully substituted pyridine. The pyridine carbons were readily distinguishable from other substituted Sp2 carbons (C-3, C-7 and C-ll) by the comparison of the CMR spectra between PA and octahydro PA/) since the formers remained at the same chemical shifts in the spectrum of octahydro PA. By feedings of sodium acetate-l_BC, acetate-2_13C and propionate-l-lsC, three signals at 0112.24, 154.29 and 128.02 were assigned to C-2', C-3' and C-4' repsectively, because C-3' and C-4' were l3C-enriched by propionate-I-1 3C and acetate-2-13 C respectively ( Figs.…”