Studies on Chilean Fungi Iii. Free and Bound Sterols From Mycena Chlorinella* (Basidiomycetes)

Secondary metabolites from fungi have become a major source of chemical innovation in programs searching for lead molecules with bioactivities, especially over the last 50 years. In this review, we discuss the fundamental considerations in the discovery of molecules for agricultural and medicinal uses. This group of organisms possesses a strong potential for scientific and industrial communities. Recently, the incorporation of new technologies for the artificial cultivation of fungi and the use of better equipment to isolate and identify active metabolites has allowed the discovery of leading molecules for the design of new and safer drugs and pesticides. The geographical region including the Patagonian Andes mountains harbors a wide diversity of fungi, many of them still unknown and so far associated with Chilean-Argentinian Andean endemic forests. There have been very few chemical studies of the fungi located in this region. However, those few studies have allowed the discovery of new molecules. We argue that the richness of fungal biodiversity in this region offers an interesting source for the discovery of bioactive molecules for the basic and applied sciences.

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“…Later, Piovano et al . reported fatty acids and sterols from carpophores of M. chlorinella . Using Grifola gargal , de Bruijn et al.…”

Section: Secondary Metabolites Isolated From Chilean Fruiting Bodiesmentioning

confidence: 99%

The impact of Andean Patagonian mycoflora in the search for new lead molecules

Aqueveque

Cespedes‐Acuña

Kubo

et al. 2017

Annals of the New York Academy of Sciences

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“…In our chemical investigation of an endophytic fungus A. flavus that was isolated from the inner tissue of the marine red alga Corallina officinalis , a new oxylipin, (8 E ,12 Z )‐10,11‐dihydroxyoctadeca‐8,12‐dienoic acid ( 1 ), and a new steroid, 3β,4α‐dihydroxy‐26‐methoxyergosta‐7,24(28)‐dien‐6‐one ( 2 ), were characterized. Moreover, four known steroids, episterol ( 3 ),14 (22 E ,24 R )‐ergosta‐7,22‐dien‐3β,5α,6α‐triol ( 4 ),15 (22 E ,24 R )‐ergosta‐5,22‐dien‐3β‐ol ( 5 ),16 and (22 E ,24 R )‐ergosta‐4,6,8(14),22‐tetraen‐3‐one ( 6 ),17 were isolated and identified (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Steroids and an oxylipin from an algicolous isolate of Aspergillus flavus

Qiao

Miao

et al. 2011

Magnetic Reson in Chemistry

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A new oxylipin, (8E,12Z)-10,11-dihydroxyoctadeca-8,12-dienoic acid (1), a new steroid, 3β,4α-dihydroxy-26-methoxyergosta-7,24(28)-dien-6-one (2), and four known steroids, episterol (3), (22E,24R)-ergosta-7,22-dien-3β,5α,6α-triol (4), (22E,24R)-ergosta-5,22-dien-3β-ol (5), and (22E,24R)-ergosta-4,6,8(14),22-tetraen-3-one (6), were isolated from the cultures of Aspergillus flavus, an endophytic fungus isolated from the marine red alga Corallina officinalis. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. 1 and 2 exhibited low activity to inhibit acetylcholinesterase and no activity against plant pathogenic fungi Colletotrichum lagenarium and Fusarium oxysporum.

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“…The cucurbitanes present in the fruiting bodies were compared with those extracted from mycelia grown on the modified Melin-Norkans (MMN) culture medium. Cucurbitacins B (1) and D (5), as well as leucopaxillones A (3) and B (4), were isolated from both sources; in contrast, 16-deoxycucurbitacin B (6) and a mixture of fatty acid esters of cucurbitacin B (2) were absent in the mycelia. A new triterpene, 18-deoxyleucopaxillone A (7), was isolated from the mycelia, but was not detected in the fruiting bodies.…”

mentioning

confidence: 98%

“…A reinvestigation of the fruiting bodies of the mushroom Leucopaxillus gentianeus, allowed the isolation of two minor cucurbitane triterpenes, namely, cucurbitacin D (5) and the new metabolite 16-deoxycucurbitacin B (6). The latter compound lacks an oxygenated substituent at C-16, an unprecedented structural feature among congeners of cucurbitacin B.…”

mentioning

confidence: 99%

Cucurbitane Triterpenes from the Fruiting Bodies and Cultivated Mycelia of Leucopaxillus gentianeus

et al. 2006

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A reinvestigation of the fruiting bodies of the mushroom Leucopaxillus gentianeus, allowed the isolation of two minor cucurbitane triterpenes, namely, cucurbitacin D (5) and the new metabolite 16-deoxycucurbitacin B (6). The latter compound lacks an oxygenated substituent at C-16, an unprecedented structural feature among congeners of cucurbitacin B. The cucurbitanes present in the fruiting bodies were compared with those extracted from mycelia grown on the modified Melin-Norkans (MMN) culture medium. Cucurbitacins B (1) and D (5), as well as leucopaxillones A (3) and B (4), were isolated from both sources; in contrast, 16-deoxycucurbitacin B (6) and a mixture of fatty acid esters of cucurbitacin B (2) were absent in the mycelia. A new triterpene, 18-deoxyleucopaxillone A (7), was isolated from the mycelia, but was not detected in the fruiting bodies. The antiproliferative activity of the isolated triterpenes was determined against the NCI-H460 human tumor cell line, in comparison with the antitumor compound topotecan, a well-known topoisomerase I inhibitor.

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Studies on Chilean Fungi Iii. Free and Bound Sterols From Mycena Chlorinella* (Basidiomycetes)

Cited by 6 publications

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The impact of Andean Patagonian mycoflora in the search for new lead molecules

The impact of Andean Patagonian mycoflora in the search for new lead molecules

Steroids and an oxylipin from an algicolous isolate of Aspergillus flavus

Cucurbitane Triterpenes from the Fruiting Bodies and Cultivated Mycelia of Leucopaxillus gentianeus

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