Structures of Allosamidins, Novel Insect Chitinase Inhibitors, Produced by Actinomycetes

Sakuda, Shohei; Isogai, Akira; Makita, Tsukasa; MATSUMOTO, Shogo; Koseki, Koshi; Kodama, Hisashi; Suzuki, Akira

doi:10.1080/00021369.1987.10868545

Cited by 16 publications

(27 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this approach, improved or modified screening methods are critical to obtaining better compounds. New compounds thus discovered are jietacin (112), discovered by using the pine wood nematode; altemicidin (138) and dioxapyrrolomycin (20), detected using brine shrimp; and allosamidin (130), found as an enzyme inhibitor for chitinase. This category also includes a new herbicidal inhibitor of starch synthesis, 6241-B substance (67).…”

Section: Targeted Agroactivity and New Detection Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Agroactive Compounds of Microbial Origin

Tanaka¹

1993

Annual Review of Microbiology

View full text Add to dashboard Cite

Section: Targeted Agroactivity and New Detection Methodsmentioning

confidence: 99%

“…Mammalian cells do not contain chitin; hence, chitin synthesis or degradation have attracted much attention as a promising target site for insecticidal and fungicidal agents (18,58). Sakuda et al (97,130) exploited allosamidins (Figure 2), which are produced by Streptomyces No. 17 13.…”

Section: Allosamidin and Other Insecticidesmentioning

confidence: 99%

Agroactive Compounds of Microbial Origin

Tanaka¹

1993

Annual Review of Microbiology

View full text Add to dashboard Cite

“…Over the past few years, chitinases have been regarded as potential target enzymes for IGRs since the hydrolysis of chitin by the enzymes is considered the rate-determining step in the degradation of chitin. Although several compounds such as allosamidin, 1) argifin 2,3) and argadin 4) have already been discovered as chitinase inhibitors, none have been used commercially as IGRs. One reason for this is that these compounds inhibit family 18 chitinases of many different organisms.…”

Section: Introductionmentioning

confidence: 99%

Screening and partial characterization of inhibitors of insect .BETA.-N-acetylglucosaminidase

et al. 2006

View full text Add to dashboard Cite

IntroductionChitin, a linear polysaccharide of b(1,4)-linked N-acetylglucosamine residues, is a structural component of the cuticle and the peritrophic membrane in the mid-gut of insects, and the strict regulation of its metabolism is essential for the normal growth of insects. The chitinolytic enzyme system consisting of chitinase and b-N-acetylglucosaminidase (GlcNAcase) is essential for the metabolic turnover of chitin in insects, and hence, inhibitors of these enzymes are expected to be potential insect growth regulators (IGRs). Over the past few years, chitinases have been regarded as potential target enzymes for IGRs since the hydrolysis of chitin by the enzymes is considered the rate-determining step in the degradation of chitin. Although several compounds such as allosamidin, 1) argifin 2,3) and argadin 4) have already been discovered as chitinase inhibitors, none have been used commercially as IGRs. One reason for this is that these compounds inhibit family 18 chitinases of many different organisms. 5,6) We have previously isolated a novel chitinase inhibitor, FPS-1, from the culture filtrate of Sphaeropsis sp. TNPT116-Cz.7) FPS-1 potently inhibited an insect chitinase from Spodoptera litura (common cutworm), but did not inhibit an actinomycete chitinase from Streptomyces griseus. In contrast, the known chitinase inhibitor allosamidin potently inhibited both chitinases. These results indicated that the insect chitinase was apparently distinct from the chitinases of other organisms.GlcNAcase forming part of the chitinolytic enzyme system is necessary for the complete degradation of chitin into its monosaccharide, but little attention has been given to it as a target enzyme for new IGRs because of its wide distribution in nature including fungi, actinomycetes, plants and mammals. However, the presence of the insect chitinase inhibitor FPS-1 strongly suggested that the chitinolytic enzyme system in insects consists of a unique chitinase and GlcNAcase. The question then arises, are there enzyme inhibitors specific for the insect GlcNAcase in nature?This paper reports on the screening and partial characterization of inhibitors specific for the GlcNAcase of insect origin. Materials and Methods GeneralNagstatin was a gift from Microbial Chemistry Research Foundation (Japan). Pupae of Adoxophyes orana and Musca J. Pestic. Sci., 31(1), 41-46 (2006) Screening and partial characterization of inhibitors of insect b b -N-acetylglucosaminidase Microbial culture broths were screened for novel b-N-acetylglucosaminidase (GlcNAcase) inhibitors specific for the enzyme of insect origin. Four strains of actinomycetes, Streptomyces griseoloalbus JCM4480, S. clauifer JCM5059, S. anulatus NBRC13369 and S. griseus subsp. rhodochrous NBRC13849, produced unique compounds showing selective inhibition of the insect GlcNAcase. In contrast, 4 fungal strains, Paecilomyces sp. F13, F30, P. carneus F2281 and Verticillium sp. F40, were found to produce GlcNAcase inhibitors showing a broad spectrum of inhibitory activity against GlcNAc...

show abstract

“…4 ) Subsequently, several congeners of 1 have been isolated from the mycelia of allosamidin-producing microbes and have each shown different inhibitory spectra against various chitinases froin different sources. 5,6) These facts suggest that artificial modifications to the structure of 1 might lead to novel specificity as chitinase inhibitors.…”

mentioning

confidence: 99%