Title

Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms

Date of Publication

2002

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry

Subject Categories

Chemistry

College

College of Science

Department/Unit

Chemistry

Thesis Adviser

Anamy Maria C. Paano

Defense Panel Chair

Glenn V. Alea

Defense Panel Member

Eric C.R. Punzalan
Gerardo C. Janairo
Jaime Raul O. Janairo
Maribel G. Nonato

Abstract/Summary

Seven species of Philippine mushrooms belonging to families Agaricaceae and Polyporaceae are investigated for their secondary metabolites. The metabolites were extracted with methanol and worked up to separate the methanol insoluble from methanol solubles or ethyl acetate solubles. The extracts were fractionated by column chromatography and purified by repeated washing and recrystallization. Benzyl ammonium salts were identified from Lepiota americana and Lepiota cristata. Benzenedodecyldimethyl ammonium salt [54] was isolated and identified from Lepiota americana. This isolate was found to be strongly active against P. aeruginosa with the same activity index as the standard antibiotic chloramphenicol. This compound was previously synthesized as disinfectant, fungicide, biocide, and bactiricide. This is however the first report of its isolation from a natural source. Hence, a new group of biologically active compounds from mushrooms were identified. This type of compound was also identified from Lepiota clypeolaria in which the alkyl side chain is shorter.The aminofuranone-type metabolite dihydrobasidalin [48] was isolated from Lepiota cristata. This compound was previously reported as a reduction product of basidalin [10], a metabolite from the mushroom Leucoagaricus naucina. No significant biological activity was identified for this isolate.

The isolation of the sugar alcohol mannitol [36] from Agaricus arvensis, Chlorophyllum molybdites, and Lepiota cristata allowed the determination of its potential as antihypertensive agent. While this compound is commonly used as diuretic, its administration to spontaneously hypertensive rats (SHR) showed that this compound elevates both the systolic and diastolic blood pressure. A number of triterpenes were also identified from the mushroom samples. Two of these triterpenes namely, ergost-6, 22-dien-eB-5a-8a-triol [72] and trametenolic acid [37] were identified from their MS and NMR data. Both compounds were known but revised NMR chemical shifts were assigned for compound [72]. This is the first report of ergost-6, 22-dien-3B-5a-8a-triol [72] isolated from mushroom. This compound was previously isolated from plants. Other known triterpenes such as y-sitosterol [76], 3B-hydroxy-5,8-epidioxyergosta-6,22-diene [13], ergost-25-ene-3,6-dione,5a,12B,-dihydroxy [62], and stigmasta-4,7,22-triene-3a-ol [63] were also identified. The crude methanolix extract of Agaricus arvensis was found to lower both the systolic and diastolic pressure of spontaneously hypertensive rats. However, at a dose of 20 mg/Kg, an increase of 11 percent in the diastolic blood pressure as observed. It is recommended that the compound responsible for the lowering of the blood pressure be identified in the future.

Abstract Format

html

Language

English

Format

Print

Accession Number

TG03304

Shelf Location

Archives, The Learning Commons, 12F Henry Sy Sr. Hall

Physical Description

221 leaves

Keywords

Mushrooms; Salts; Biological products; Metabolites; Terpenes

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