I. Extracellular metabolites from coprinus macrorhizus microsporus. Isolation and characterization of hydroxylagopodin B. II. The cell wall composition and structure of coprinus macrorhizus microsporus
“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.
Siehr, Donald J.
Carroll, William R.
Milton S. Feather
Gale, Nord L.
Hanna, Samir B.
Ph. D. in Chemistry
University of Missouri--Rolla
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
xiv, 131 pages
© 1979 Carey Bernard Bottom, All rights reserved.
Dissertation - Open Access
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Bottom, Carey Bernard, "I. Extracellular metabolites from coprinus macrorhizus microsporus. Isolation and characterization of hydroxylagopodin B. II. The cell wall composition and structure of coprinus macrorhizus microsporus" (1979). Doctoral Dissertations. 439.