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19-O-Acetylchaetoglobosin A Sale

(Synonyms: Chaetoglobosin A Acetate) 目录号 : GC48423

A fungal metabolite with actin polymerization inhibitory and cytotoxic activities

19-O-Acetylchaetoglobosin A Chemical Structure

Cas No.:50939-69-0

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产品描述

19-O-Acetylchaetoglobosin A is a fungal metabolite originally isolated from C. globosum that has actin polymerization inhibitory and cytotoxic activities.1,2 It inhibits actin polymerization in a cell-free assay when used at a concentration of 2 µM.2 19-O-Acetylchaetoglobosin A (3.2, 10, and 32 µg/ml) is cytotoxic to HeLa cervical cancer cells.1

1.Umeda, M., Ohtsubo, K., Saito, M., et al.Cytotoxicity of new cytochalasans from Chaetomium globosumExperientia31(4)435-438(1975) 2.Sekita, S., Yoshihira, K., Natori, S., et al.Structure-activity relationship of thirty-nine cytochalasans observed in the effects on cellular structures and cellular events and on actin polymerization in vitroJ. Pharmacobiodyn.8(11)906-916(1985)

Chemical Properties

Cas No. 50939-69-0 SDF
别名 Chaetoglobosin A Acetate
Canonical SMILES [H][C@]1(/C=C/C[C@H](C)/C=C2C)[C@]3([H])O[C@@]3([C@H]([C@]4([C@@H](NC([C@]41C(/C=C/C([C@@H]\2OC(C)=O)=O)=O)=O)CC5=CNC6=C5C=CC=C6)[H])C)C
分子式 C34H38N2O6 分子量 570.7
溶解度 储存条件 -20°C
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1 mg 5 mg 10 mg
1 mM 1.7522 mL 8.7612 mL 17.5223 mL
5 mM 0.3504 mL 1.7522 mL 3.5045 mL
10 mM 0.1752 mL 0.8761 mL 1.7522 mL
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Research Update

Ijuhya vitellina sp. nov., a novel source for chaetoglobosin A, is a destructive parasite of the cereal cyst nematode Heterodera filipjevi

PLoS One 2017 Jul 12;12(7):e0180032.PMID:28700638DOI:10.1371/journal.pone.0180032.

Cyst nematodes are globally important pathogens in agriculture. Their sedentary lifestyle and long-term association with the roots of host plants render cyst nematodes especially good targets for attack by parasitic fungi. In this context fungi were specifically isolated from nematode eggs of the cereal cyst nematode Heterodera filipjevi. Here, Ijuhya vitellina (Ascomycota, Hypocreales, Bionectriaceae), encountered in wheat fields in Turkey, is newly described on the basis of phylogenetic analyses, morphological characters and life-style related inferences. The species destructively parasitises eggs inside cysts of H. filipjevi. The parasitism was reproduced in in vitro studies. Infected eggs were found to harbour microsclerotia produced by I. vitellina that resemble long-term survival structures also known from other ascomycetes. Microsclerotia were also formed by this species in pure cultures obtained from both, solitarily isolated infected eggs obtained from fields and artificially infected eggs. Hyphae penetrating the eggshell colonised the interior of eggs and became transformed into multicellular, chlamydospore-like structures that developed into microsclerotia. When isolated on artificial media, microsclerotia germinated to produce multiple emerging hyphae. The specific nature of morphological structures produced by I. vitellina inside nematode eggs is interpreted as a unique mode of interaction allowing long-term survival of the fungus inside nematode cysts that are known to survive periods of drought or other harsh environmental conditions. Generic classification of the new species is based on molecular phylogenetic inferences using five different gene regions. I. vitellina is the only species of the genus known to parasitise nematodes and produce microsclerotia. Metabolomic analyses revealed that within the Ijuhya species studied here, only I. vitellina produces chaetoglobosin A and its derivate 19-O-Acetylchaetoglobosin A. Nematicidal and nematode-inhibiting activities of these compounds have been demonstrated suggesting that the production of these compounds may represent an adaptation to nematode parasitism.

Phytotoxic chaetoglobosins are produced by the plant pathogen Calonectria morganii (anamorph Cylindrocladium scoparium)

J Gen Appl Microbiol 2001 Feb;47(1):33-38.PMID:12483566DOI:10.2323/jgam.47.33.

By the application of a bioassay based on cresson seedlings, two phytotoxic compounds were isolated by thin-layer chromatography from the culture fluid of a Calonectria morganii isolate. The structure of both compounds was elucidated by ESI/MS and NMR spectroscopy. According to the Chemical Abstracts database, they were identified as chaetoglobosin A and 19-O-Acetylchaetoglobosin A, mycotoxins originally described for Chaetomium globosum.

Photoaffinity labeling of plasma membrane receptors for cytochalasins in Ehrlich tumor cells

Biochimie 1988 Feb;70(2):187-91.PMID:3134942DOI:10.1016/0300-9084(88)90060-0.

Treatment of purified Ehrlich ascites cell plasma membranes either with [3H]cytochalasin B or [3H]19-O-Acetylchaetoglobosin A under photolytic conditions produced several radioactive polypeptides which were characterized by SDS-PAGE analyses. The major proteins so photolabeled were in the 60,000-80,000 Da range, with less labeling found in polypeptides smaller than 43,000 and greater than 90,000 Da. Immunofluorescent staining failed to identify the major photolabeled component as actin. It is concluded, in keeping with prior investigations using other cell types, that the predominant proteins photolabeled by cytochalasins are affiliated with the glucose-transport system.