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Structure of pestalotan, a highly branched (1----3)-beta-D-glucan elaborated by Pestalotia sp. 815, and the enhancement of its antitumor activity by polyol modification of the side chains.
Carbohydr Res. 1984 Jul 01; 129:209-27.CR

Abstract

Pestalotia sp. 815, a newly isolated fungus, produces extracellularly a highly (1----6)-branched (1----3)-beta-D-glucan in high yield when grown in a D-glucose-containing medium. This extracellular glucan, designated "Pestalotan", has [alpha]25D-0.1 degree (c 0.5, M NaOH) and a molecular weight greater than 2 X 10(6). Chemical and enzymic studies indicated that pestalotan has a very highly branched structure containing a back-bone chain of beta-D-(1----3)-linked D-glucosyl residues, and three out of five D-glucosyl residues are substituted at O-6, mostly with single D-glucosyl groups, and a very few with short beta-(1----6)-linked oligosaccharide units. This D-glucan becomes water-insoluble after isolation from the culture filtrate followed by dehydration, and shows moderate growth-inhibitory activities against mouse-implanted tumors. However, when the D-glucosyl groups of the side chains were modified by periodate oxidation and borohydride reduction, the resulting, still water-insoluble, D-glucan polyol exhibited potent antitumor activities, confirming that the attachment of many polyhydroxy groups to the beta-D-(1----3)-linked D-glucan back-bone gives a remarkable enhancement effect on the antitumor activity of the branched D-glucan. Prolonged treatment of the D-glucan polyol by ultrasonic irradiation afforded a low-molecular-weight D-glucan polyol (SD-pestalotan polyol), without alteration of its chemical structure. The water-soluble, SD-pestalotan polyol, having a molecular weight of 4.7 X 10(5), exhibited remarkable antitumor activities against both allogeneic and syngeneic, mouse-implanted tumors, at small dosages (1-5 mg/kg for 10 days) by intraperitoneal administration. A comparison of values of the molecular weight of SD-pestalotan polyol, estimated by 3-MPa l.c. for the aqueous solution and the dimethyl sulfoxide solution, strongly suggested that the D-glucan polyol must form a triple-chain conformation in aqueous solution.

Authors

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Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

6547877

Citation

Misaki, A, et al. "Structure of Pestalotan, a Highly Branched (1----3)-beta-D-glucan Elaborated By Pestalotia Sp. 815, and the Enhancement of Its Antitumor Activity By Polyol Modification of the Side Chains." Carbohydrate Research, vol. 129, 1984, pp. 209-27.
Misaki A, Kawaguchi K, Miyaji H, et al. Structure of pestalotan, a highly branched (1----3)-beta-D-glucan elaborated by Pestalotia sp. 815, and the enhancement of its antitumor activity by polyol modification of the side chains. Carbohydr Res. 1984;129:209-27.
Misaki, A., Kawaguchi, K., Miyaji, H., Nagae, H., Hokkoku, S., Kakuta, M., & Sasaki, T. (1984). Structure of pestalotan, a highly branched (1----3)-beta-D-glucan elaborated by Pestalotia sp. 815, and the enhancement of its antitumor activity by polyol modification of the side chains. Carbohydrate Research, 129, 209-27.
Misaki A, et al. Structure of Pestalotan, a Highly Branched (1----3)-beta-D-glucan Elaborated By Pestalotia Sp. 815, and the Enhancement of Its Antitumor Activity By Polyol Modification of the Side Chains. Carbohydr Res. 1984 Jul 1;129:209-27. PubMed PMID: 6547877.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structure of pestalotan, a highly branched (1----3)-beta-D-glucan elaborated by Pestalotia sp. 815, and the enhancement of its antitumor activity by polyol modification of the side chains. AU - Misaki,A, AU - Kawaguchi,K, AU - Miyaji,H, AU - Nagae,H, AU - Hokkoku,S, AU - Kakuta,M, AU - Sasaki,T, PY - 1984/7/1/pubmed PY - 1984/7/1/medline PY - 1984/7/1/entrez SP - 209 EP - 27 JF - Carbohydrate research JO - Carbohydr Res VL - 129 N2 - Pestalotia sp. 815, a newly isolated fungus, produces extracellularly a highly (1----6)-branched (1----3)-beta-D-glucan in high yield when grown in a D-glucose-containing medium. This extracellular glucan, designated "Pestalotan", has [alpha]25D-0.1 degree (c 0.5, M NaOH) and a molecular weight greater than 2 X 10(6). Chemical and enzymic studies indicated that pestalotan has a very highly branched structure containing a back-bone chain of beta-D-(1----3)-linked D-glucosyl residues, and three out of five D-glucosyl residues are substituted at O-6, mostly with single D-glucosyl groups, and a very few with short beta-(1----6)-linked oligosaccharide units. This D-glucan becomes water-insoluble after isolation from the culture filtrate followed by dehydration, and shows moderate growth-inhibitory activities against mouse-implanted tumors. However, when the D-glucosyl groups of the side chains were modified by periodate oxidation and borohydride reduction, the resulting, still water-insoluble, D-glucan polyol exhibited potent antitumor activities, confirming that the attachment of many polyhydroxy groups to the beta-D-(1----3)-linked D-glucan back-bone gives a remarkable enhancement effect on the antitumor activity of the branched D-glucan. Prolonged treatment of the D-glucan polyol by ultrasonic irradiation afforded a low-molecular-weight D-glucan polyol (SD-pestalotan polyol), without alteration of its chemical structure. The water-soluble, SD-pestalotan polyol, having a molecular weight of 4.7 X 10(5), exhibited remarkable antitumor activities against both allogeneic and syngeneic, mouse-implanted tumors, at small dosages (1-5 mg/kg for 10 days) by intraperitoneal administration. A comparison of values of the molecular weight of SD-pestalotan polyol, estimated by 3-MPa l.c. for the aqueous solution and the dimethyl sulfoxide solution, strongly suggested that the D-glucan polyol must form a triple-chain conformation in aqueous solution. SN - 0008-6215 UR - https://www.unboundmedicine.com/medline/citation/6547877/Structure_of_pestalotan_a_highly_branched__1____3__beta_D_glucan_elaborated_by_Pestalotia_sp__815_and_the_enhancement_of_its_antitumor_activity_by_polyol_modification_of_the_side_chains_ L2 - https://linkinghub.elsevier.com/retrieve/pii/0008-6215(84)85313-6 DB - PRIME DP - Unbound Medicine ER -