Concentricol, a taxonomically significant triterpenoid from Daldinia concentrica

Stadler, Marc; Baumgärtner, Manuela; Grothe, Torsten; Mühlbauer, Andrea; Seip, Stephan; Wollweber, H.

doi:10.1016/s0031-9422(01)00032-2

Cited by 47 publications

(40 citation statements)

References 14 publications

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“…7080 were identified by comparing their NMR spectroscopic data with those reported in the literature: 1-(2,6-dihydroxyphenyl)butan-1-one (2), [2,3] 5-hydroxy-2-methyl-4H-chromen-4-one (4), [2] 2,3-dihydro-5-hydroxy-2-methylchromen-4-one (5), [4] 8-methoxynaphthalen-1-ol (7), [5] 1,8-dimethoxynaphthalene (8), [5] daldinol (11), [6] (4R,5S,6S)-6-[(E)-but-2-en-2-yl]-tetrahydro-4-hydroxy-3,3,5-trimethylpyran-2-one (helicascolide A, 14), [7] the eudesmane derivative (1S,4S,4aS,6R,8aR)-decahydro-1,4-dimethyl-6-(prop-1-en-2-yl)naphthalen-1-ol (15), previously isolated from unripe fruits of Ocotea corymbosa, [8] ergosterol (16), [9] and 5α,8α-epidioxyergosterol (17). [10] The optically active new compound 1 ([α] D 25 = -12.0) was obtained as colorless crystals with the molecular formula C 10 H 12 O 4 , as deduced from HREIMS spectral and 13 C NMR spectroscopic data.…”

Section: Resultsmentioning

confidence: 99%

“…A literature survey revealed that this dimer is a known natural product, named daldinol. [6,16] Interestingly, in both papers, only this para-para coupling product 11 is described to occur in the Ascomycete Daldinia concentrica, whereas the other possible ortho-para (9) and ortho-ortho (10) combinations are only produced by the currently investigated endophytic fungus Nodulisporium sp.…”

Section: Resultsmentioning

confidence: 99%

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Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre

et al. 2006

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Seven new metabolites, 3‐hydroxy‐1‐(2,6‐dihydroxyphenyl)butan‐1‐one (1), 1‐(2‐hydroxy‐6‐methoxyphenyl)butan‐1‐one (3), 2,3‐dihydro‐5‐methoxy‐2‐methylchromen‐4‐one (6), the dimeric naphthalenes nodulisporin A (9) and B (10), and the first naturally occurring dimeric indanone, nodulisporin C (12), as well as (4E,6E)‐2,4,6‐trimethylocta‐4,6‐dien‐3‐one (13) were isolated together with ten known compounds (2, 4, 5, 7, 8, 11, 14–17) from the culture extract of the endophytic fungus Nodulisporium sp. from Juniperus cedre from Gomera Island. The structure of dictafolin‐A, previously erroneously assigned as structure 6, is not identical with 2,3‐dihydro‐5‐methoxy‐2‐methylchromen‐4‐one, isolated in this investigation. The structures of new compounds were determined by spectroscopic methods (mainly extensive 1D and 2D NMR experiments and mass spectral measurements) and X‐ray single crystal analysis. All but one of the thirteen tested compounds exhibit herbicidal, antifungal and/or antibacterial activities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre

et al. 2006

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“…Some of these compounds were later found to show antimicrobial and nematicidal activities [3]. More recently, the squalene-type triterpenoids concentricols A and B ± D were isolated from the fruiting bodies of the fungus by Stadler and co-workers [4] and Asakawa and co-workers [5], respectively. As part of our search for bioactive metabolites from higher fungi in Yunnan Province, China [6 ± 10], the culture broth of D. concentrica was investigated.…”

Section: H H-cosy)mentioning

confidence: 99%

“…Me (1) 4 1.5 g, citric acid 0.1 g, and thiamin hydrochloride 10 mg in 1 l of deionized H 2 O (pH 6.5 before autoclaving). The culture soln.…”

Section: H H-cosy)mentioning

confidence: 99%

A Pair of Novel Heptentriol Stereoisomers from the Ascomycete Daldinia concentrica

Wang

Liu

2004

Helvetica Chimica Acta

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A pair of novel heptentriol stereoisomers, hept‐6‐ene‐2,4,5‐triols 2 and 3, were isolated from the culture broth of the ascomycete Daldinia concentrica (Bolton : Fries) Cesati & De Notaris, besides three known compounds, i.e., 2,3‐dihydro‐5‐hydroxy‐2‐methyl‐4H‐1‐benzopyran‐4‐one (1), 3,5‐dihydroxy‐2‐(1‐oxobutyl)‐cyclohex‐2‐en‐1‐one (4), and pyroglutamic acid (=5‐oxo‐L‐proline; 5). Their structures were determined by spectroscopic means, including 2D‐NMR (HMQC, HMBC, 1H,1H‐COSY).

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“…Studies with Daldinia spp. have revealed more than 20 new bioactive metabolites, including derivatives of benzofenones (Hashimoto et al 1994a), azafilones, daldinins A-C (Hashimoto et al 1994b), cytochalasans (Buchanan et al 1995;1996a, b;Hashimoto and Asakawa 1998), triterpenoids, concentricols (Stadler et al 2001a;Quang et al 2002a, b), daldiniapyrone, daldinones (Quang et al 2002b), benzoquinones (Qin and Liu 2004a), esteroids (Qin and Liu 2004b), heptentriols (Wang and Liu 2004), diaporthins, orthosporins (Lee et al 2006), and concentricolides (Qin et al 2006).…”

Section: Introductionmentioning

confidence: 99%

Daldinia eschscholtzii (Ascomycota, Xylariaceae) isolated from the Brazilian Amazon: taxonomic features and mycelial growth conditions

et al. 2013

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The Amazon has a high diversity of fungi, including species of the genus Daldinia (Ascomycota, Xylariaceae), which produce secondary metabolites with recognized nematicidal and antimicrobial activity. The ecological role of Daldinia is important, as stromata serve as refuges to many insects and arthropodes, and the fungi contribute to the degradation of vegetable organic matter. The aim of this study was to analyze the taxonomic features and mycelial growth conditions in vitro of a Daldinia specimen collected in the Brazilian Amazon. Morphological and molecular studies of the fungus identified it as D. eschscholtzii. To evaluate mycelial growth, we cultivated the fungus at 20, 25, 30, 35, and 40 ºC in malt extract-peptone agar (MEPA), malt extract-peptone (MEP), potato dextrose (PD), and minimum medium (MM). The best mycelial growth occurred at 35 ºC, although the greatest amount of biomass was obtained at 25 ºC and 30 ºC. PD proved to be the best medium for biomass production. KEYWORDS: Daldinia eschscholzii, fungal diversity, macrofungus, occurrence. Daldinia eschscholzii (Ascomycota, Xylariaceae) isolado na Amazônia brasileira: características taxonômicas e condições de crescimento micelial RESUMOA Amazônia apresenta alta diversidade de fungos, incluindo Daldinia (Ascomycota, Xylariaceae), cujas espécies produzem metabólitos secundários com reconhecida atividade antimicrobiana e nematicida. O papel ecológico é importante, visto que estromas servem de abrigo para muitos insetos e artrópodes, além de contribuir na degradação da matéria orgânica vegetal. O objetivo desse estudo foi analizar as características taxonômicas e as condições do crescimento micelial in vitro de um espécime de Daldinia coletado na Amazônia brasileira. Estudos morfológicos e moleculares do fungo o indetificaram como D. eschscholtzii. Para avaliação do crescimento micelial o fungo foi cultivado nas temperaturas de 20, 25, 30, 35 e 40 ºC e nos meios de cultura extrato de malte-peptona ágar (EMPA), extrato de malte-peptona (EMP), batata dextrose (BD) e meio mínimo (MM). O melhor crescimento micelial ocorreu a 35 ºC, entretanto, a maior quantidade de biomassa foi obtida a 25 e 30 ºC. O meio BD provou ser o melhor meio para produção de biomassa.

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Concentricol, a taxonomically significant triterpenoid from Daldinia concentrica

Cited by 47 publications

References 14 publications

Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre

Metabolites from the Endophytic Fungus Nodulisporium sp. from Juniperus cedre

A Pair of Novel Heptentriol Stereoisomers from the Ascomycete Daldinia concentrica

Daldinia eschscholtzii (Ascomycota, Xylariaceae) isolated from the Brazilian Amazon: taxonomic features and mycelial growth conditions

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