Doctoral Dissertations

Abstract

“A purple pigment excreted into the culture medium of a mutant strain of the basidiomycete, Coprinus macrorhizus var. microsporus (ATCC 34960) has been isolated and characterized as hydroxylagopodin B based on ultraviolet, infrared, and mass spectral data. A wild-type strain of C. macrorhizus microsporus does not produce the purple pigment, however it does produce lagopodin B which is yellow in solution. Identification of lagopodin B was based on its melting point, the purple color of its alkaline solution, the mass spectrum, and mobility equivalence with a standard by thin-layer chromatography. The production of hydroxylagopodin B in the mutant strain is concomitant with a significant increase in the phenoloxidase activity of the culture medium. Some phenoloxidases possess activity which hydroxylates phenols or their derivatives. Since the structures of hydroxylagopodin B and lagopodin B differed by the substitution of a hydroxy group on the benzoquinone nucleus, it was proposed that hydroxylagopodin was a product of non-specific hydroxylation of lagopodin B as the corresponding quinol catalyzed by the mutant's phenoloxidase. Evidence indicated that the purified phenoloxidase did not hydroxylate lagopodin B under the given conditions, however it is probable that an indirect relationship exists between the production of hydroxylagopodin B and the increase in phenoloxidase activity.

The cell-wall structure of wild-type C. macrorhizus microsporus was also studied.

A unique, alkali-soluble polysaccharide has been isolated from the cell walls of the basidiomycete, Coprinus macrorhizus microsporus. The polysaccharide, which is primarily glucan in nature, contains a large proportion of α -(1→4)-linked D-glucose residues and a smaller amount of ß-(1→3),(1→6) linkages as suggested by methylation, partial acid hydrolysis, periodate, and enzymic studies. Hydrolysis of the methylated polysaccharide gave equimolar amounts of 2,4-di- and 2,3-di-0-methyl-D-glucose; no 2,6-di-0-methyl-D-glucose was identified indicating the absence of branch points joined through 0-1, 0-3 and 0-4. The isolation and identification of 2-0-a-glucopyranosyl erythritol from the periodate oxidation of the polysaccharide suggests that segments of the α-(1→4)-linked D-glucose residues are joined by single (1→3)-linkages. An extracellular enzyme preparation from Sporotrichum dimorphosporum (QM 806) containing both ß-(1→3) and α-(1→4) glucano- hydrolase activity released 76% of the reducing groups from the polysaccharide. The polysaccharide also contains minor amounts of xylose, mannose, glucosamine and amino acids.

The alkali-insoluble (R-) fraction from the cell walls of Coprinus macrorhizus var. rnicrosporus is a highly-branched glucan, containing α-(1→4), ß-(1→3) and ß-(1→6) linkages as shown by methylation, partial acid hydrolysis and enzymic hydrolysis. The α-(1→4)-linked segments are joined by occasional ß-(1→3) links as suggested by the identification of 2-0- α -glucopyranosyl erythritol in the hydrolysate of the reduced, periodate-oxidized glucan. Hydrolysis of the permethylated glucan gave nearly equimolar amounts of 2,4-di- and 2,3-di-0-methyl-D-glucose. Methylation analysis of the residue from enzymic hydrolysis, the CORE-fraction, indicated the presence of glucose residues in this fraction also, linked through positions 0-1, 0-3, 0-4 and 0-6. Hydrolysates of the R-fraction also contained mannose, glucosamine and amino acids in addition to glucose”--Abstract, pages iii-v.

Advisor(s)

Siehr, Donald J.

Committee Member(s)

Carroll, William R.
Milton S. Feather
Gale, Nord L.
Hanna, Samir B.

Department(s)

Chemistry

Degree Name

Ph. D. in Chemistry

Publisher

University of Missouri--Rolla

Publication Date

1979

Journal article titles appearing in thesis/dissertation

  • Hydroxylagopodin B, a Sesquiterpenoid Quinone from a Mutant Strain of Coprinus macrorhizus var. microsporus
  • Structure of an Alkali-Soluble Polysaccharide from the Hyphal Wall of the Basidiomycete, Coprinus macrorhizus var. rnicrosporus
  • Structure and Composition of the Alkali-insoluble Cell Wall Fraction of Coprinus macrorhizus var. rnicrosporus

Pagination

xiv, 131 pages

Note about bibliography

Includes bibliographical references.

Rights

© 1979 Carey Bernard Bottom, All rights reserved.

Document Type

Dissertation - Open Access

File Type

text

Language

English

Thesis Number

T 4474

Print OCLC #

5978923

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Included in

Chemistry Commons

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