Structures of allosamidins, novel insect chitinase inhibitors, produced by actinomycetes.

Sakuda, Shohei; Isogai, Akira; Makita, Tsukasa; Matsumoto, Shogo; Koseki, Keita; Kodama, Hisashi; Suzuki, Akira

doi:10.1271/bbb1961.51.3251

Cited by 49 publications

(3 citation statements)

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“…As part of the study we have used allosamidin, a specific chitinase inhibitor produced by Streptomyces spp. (Sakuda etal., 1987a, b). It is a pseudo-trisaccharide containing N -acetylallosa- mine and has been used to study inhibition of chitinase activity in a number of biological systems (Gooday, 1990; Gooday et al, 1988; Milewski et al, 1992; Shahabuddin et al, 1993).…”

Section: Introductionmentioning

confidence: 99%

Involvement of chitinases of Bacillus thuringiensis during pathogenesis in insects

1998

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Bacillus thuringiensis su bsp. israelensis IPS78 and B. thuringiensis su bsp. aizawai HD133 both secreted exochitinase activity when grown in a medium containing chitin. Allosamidin, a specific chitinase inhibitor, inhibited activity from both strains, with I C, values of about 50 pM with colloidal chitin as substrate and between 1 and 10 pM with 4-methylumbelliferyldiacetylchitobioside and 4-methylumbelliferyl-triacetylchitotrioside as substrates. The involvement of these chitinolytic activities during pathogenesis in insects has been investigated with B. thuringiensis subsp. israelensis IPS78 against larvae of the midge Culicoides nubeculosus, and with B. thuringiensis subsp. aizawai HD133 against caterpillars of the cotton leafworm Spodoptera littoralis. Presence of 100 pM allosamidin increased the LD50 by factors of 1.3 and 14, respectively, demonstrating a role for bacterial chitinases in the attack on the insects. Presence of chitinase A from Serratia marcescens considerably decreased the values for LD,, confirming previous observations with different systems of the potentiation of entomopathogenesis of B. thuringiensis by exogenous chitinases. The most likely action of the endogenous chitinases of B. thuringiensis is to weaken the insects' peritrophic membranes, allowing more ready access of the bacterial toxins to the gut epithelia. Addition of exogenous chitinases will then increase this effect. Complementary cross-infection experiments, strain HD133 against midge larvae and strain IPS78 against caterpillars, were performed to investigate the pathogenhost specificities of the effects. Results showed that much higher concentrations of bacteria were required to achieve even low mortalities, and addition of chitinase A gave no increase in death rate.

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Section: Introductionmentioning

confidence: 99%

Involvement of chitinases of Bacillus thuringiensis during pathogenesis in insects

1998

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“…Most interestingly, no chitin exists in mammals, so chitin-metabolizing enzymes are potential targets for the development of green pesticides. To date, several potent GH18 chitinase inhibitors have been reported, such as argifin, argadin, allosamidin, − dipyrido-pyrimidine derivatives, and berberine (BER) derivatives . Natural products argifin and argadin have a broad spectrum of chitinase inhibitory activity but are restricted in their practical application due to the complexity of their synthesis.…”

Section: Introductionmentioning

confidence: 99%

Rational Design of N-Methylcarbamoylguanidinyl Derivatives as Highly Potent Dual-Target Chitin Hydrolase Inhibitors for Retarding Growth of Pest Insects

Zhao

Chen

Wang

et al. 2023

J. Agric. Food Chem.

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Chitin degradation is a vital process for the growth of insects. Chitin hydrolase OfChtI and β-N-acetylhexosaminidase OfHex1 are two key enzymes involved in hydrolyzing the chitin of insects’ cuticles. Thus, they are considered promising targets for preventing and controlling agricultural pests. In this study, we designed and synthesized a series of compounds bearing N-methylcarbamoylguanidinyl and N-methoxycarbonylguanidinyl as dual-target inhibitors of OfChtI and OfHex1. The most potent dual-target inhibitor, compound 10d, exhibited half-maximal inhibitory concentration (IC50) values of 27.1 and 249.1 nM against OfChtI and OfHex1, respectively. Furthermore, the insecticidal activity studies showed that compounds 10a–c, 10k, and 10l bear significant effects on the growth and development of Plutella xylostella. This work provides a promising method for the development of novel chitin hydrolase inhibitors as potential pest control and management agents.

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“…Allosamidin (Figure 1), a metabolite of a soil bacterium Streptomyces sp., was discovered in 1986 as the first chitinase inhibitor [6,7]. It has a unique pseudotrisaccharide structure consisting of two N -acetyl-D-allosamine moieties and one allosamizoline moiety [8,9]. Allosamizoline is a unique five-membered cyclitol derivative fused with a dimethylaminooxazoline ring.…”

Section: Introductionmentioning

confidence: 99%

Novel Biological Activities of Allosamidins

2013

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Allosamidins, which are secondary metabolites of the Streptomyces species, have chitin-mimic pseudotrisaccharide structures. They bind to catalytic centers of all family 18 chitinases and inhibit their enzymatic activity. Allosamidins have been used as chitinase inhibitors to investigate the physiological roles of chitinases in a variety of organisms. Two prominent biological activities of allosamidins were discovered, where one has anti-asthmatic activity in mammals, while the other has the chitinase-productionpromoting activity in allosamidin-producing Streptomyces. In this article, recent studies on the novel biological activities of allosamidins are reviewed.

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Structures of allosamidins, novel insect chitinase inhibitors, produced by actinomycetes.

Cited by 49 publications

References 1 publication

Involvement of chitinases of Bacillus thuringiensis during pathogenesis in insects

Involvement of chitinases of Bacillus thuringiensis during pathogenesis in insects

Rational Design of N-Methylcarbamoylguanidinyl Derivatives as Highly Potent Dual-Target Chitin Hydrolase Inhibitors for Retarding Growth of Pest Insects

Novel Biological Activities of Allosamidins

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