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

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...

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Main Author: Caballero, Shirley L.
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Language:English
Published: Animo Repository 2002
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Online Access:https://animorepository.dlsu.edu.ph/etd_doctoral/1211
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Institution: De La Salle University
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spelling oai:animorepository.dlsu.edu.ph:etd_doctoral-22122021-05-31T06:09:48Z Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms Caballero, Shirley L. 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. 2002-01-01T08:00:00Z text https://animorepository.dlsu.edu.ph/etd_doctoral/1211 Dissertations English Animo Repository Mushrooms Salts Biological products Metabolites Terpenes Chemistry
institution De La Salle University
building De La Salle University Library
continent Asia
country Philippines
Philippines
content_provider De La Salle University Library
collection DLSU Institutional Repository
language English
topic Mushrooms
Salts
Biological products
Metabolites
Terpenes
Chemistry
spellingShingle Mushrooms
Salts
Biological products
Metabolites
Terpenes
Chemistry
Caballero, Shirley L.
Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
description 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.
format text
author Caballero, Shirley L.
author_facet Caballero, Shirley L.
author_sort Caballero, Shirley L.
title Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
title_short Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
title_full Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
title_fullStr Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
title_full_unstemmed Aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
title_sort aminofuranone, benzylammonium salts, sugar alcohol and triterpenes from selected species of agaricaceae and polyporaceae mushrooms
publisher Animo Repository
publishDate 2002
url https://animorepository.dlsu.edu.ph/etd_doctoral/1211
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