Sterol analysis of DMI-resistant and -sensitive strains of Venturia inaequalis

Shirane, Noboru; Takenaka, Hideyuki; Ueda, Kazuo; Hashimoto, Yutaka; Katoh, Kenji; Ishii, Hideo

doi:10.1016/0031-9422(95)00787-3

Cited by 65 publications

(42 citation statements)

References 10 publications

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“…15 Until now, this is the first report of the isolation of ergosterol (1) from L. theobromae, although the detection of 1 in maize grains has been associated with the presence of this fungus as a contaminant. 16 It should be mentioned that TLC analyses of the extracts from the control flasks did not show the presence of compound 1.…”

Section: Resultsmentioning

confidence: 90%

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Nunes¹,

Oliveira²,

Arriaga³

et al. 2008

J. Braz. Chem. Soc.

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O fungo fitopatogênico Lasiodiplodia theobromae, isolado de goiaba, foi cultivado em arroz por 32 dias à temperatura ambiente. Extração com CH 2 Cl 2 :MeOH (3:7), seguido de fracionamento cromatográfico do extrato forneceu o esteróide ergosterol. Da cultura fúngica em meio de Czapeck por 40 dias à temperatura ambiente, foram isolados a isocumarina cis-4-hidroximeleína e um sesquiterpeno do tipo eremofilano. O sesquiterpeno eremofilano está sendo descrito pela primeira vez na literatura. Este é o primeiro relato do isolamento de um sesquiterpeno eremofilano para o gênero Lasiodiplodia.The phytopatogenic fungus Lasiodiplodia theobromae, isolated from guava, was cultivated in rice for 32 days at room temperature. Extraction with CH 2 Cl 2 :MeOH (3:7), followed by chromatography fractionation of the extract provided ergosterol. From the fungus culture in Czapeck medium for 40 days at room temperature, were isolated isocoumarin cis-4-hydroxymeleine and an eremophilane-type sesquiterpene. The latter compound is being reported for the first time in the literature. Also, this is the first time that an eremophilane sesquiterpene is described for Lasiodiplodia genus.

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Section: Resultsmentioning

confidence: 90%

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Nunes¹,

Oliveira²,

Arriaga³

et al. 2008

J. Braz. Chem. Soc.

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“…19 Talaromyces sp. VrTrb2 1.1 yielded a novel substance (7) and the known compounds ergosterol (9), 20 ergosterol peroxide (10), 21 ergosta-4,6,8(14),22-tetraen-3-one (11), 22 and citric acid (12). 12 From the fungus Talaromyces sp.…”

Section: Isolated Compoundsmentioning

confidence: 99%

“…31 Anticancer activities were recorded for some derivatives against several tumor cell lines, where secalonic acid D is the most active. 32 Concerning antimicrobial activities, blennolides 21 and dicerandrols 33 inhibited several pathogens. So far, only paecilin C was evaluated for its antibacterial potential, however, showed no activity.…”

Section: Antimicrobial Assaysmentioning

confidence: 99%

Antifungal Polyketides and Other Compounds from Amazonian Endophytic Talaromyces Fungi

Silva

Souza

Bianco

et al. 2017

J. Braz. Chem. Soc.

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The continuous search for biologically active compound candidates pushes the pursuit of new substances produced by diverse organisms. Endophytic fungi are known as a promising source of metabolites with several biological activities. Based on the rich Amazonian biodiversity and the chemical potential of microbial sources, three Talaromyces strains, all major endophytes from their respective host plants, were studied aiming at the isolation of biologically active secondary metabolites. Through classical chromatographic approaches, 13 compounds were isolated from the antimicrobial extracts of the studied strains. From these, polyketides, steroids, anhydrides, and phenolic compounds were identified. Among them, two previously undescribed compounds were elucidated based on spectroscopic and spectrometric methods, a homodimer chromanone and a maleic anhydride methyl ester. The antimicrobial activity against a panel of pathogenic microorganisms from extracts, fractions, and isolated compounds was evaluated.

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“…Furthermore, zhankuic acids A and C exhibited significant cytotoxicity against P-388 murine leukemia cells in vitro 4. The present study on the chemical constituents of an EtOH extract of the fruiting body of T. camphoratus has led to the isolation of 10 new triterpenoids, namely camphoratins A–J ( 1 – 10 ), and 12 known compounds, including zhankuic acids A – C ( 11 – 13 ),4,5 zhankuic acid A methyl ester ( 14 ),4 antcin A ( 15 ),5 antcin C ( 16 ),5 antcin K ( 17 ),6 methyl antcinate H ( 18 ),7 eburicol ( 19 ),8 ergosterol D ( 20 ),9 methyl 4α-methylergost-8,24(28)-diene-3,11-dion-26-oate ( 21 ),10 and ergosterol peroxide ( 22 ) 11. Cytotoxic activity, inhibition of nitric oxide (NO) or reactive oxygen species (ROS) production, and free radical-scavenging activity of the isolates were evaluated in our study.…”

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confidence: 99%

Camphoratins A−J, Potent Cytotoxic and Anti-inflammatory Triterpenoids from the Fruiting Body of Taiwanofungus camphoratus

Leu

Chen

et al. 2010

J. Nat. Prod.

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Ten new triterpenoids, camphoratins A-J (1-10), along with 12 known compounds were isolated from the fruiting body of Taiwanofungus camphoratus. Their structures were established by spectroscopic analysis and chemical methods. Compound 10 is the first example of a naturally occurring ergosteroid with an unusual cis-C/D ring junction. Compounds 2-6 and 11 showed moderate to potent cytotoxicity with EC 50 values ranging from 0.3 to 3 μM against KB and KB-VIN human cancer cell lines. Compounds 6, 10, 11, 14-16, 18, and 21 exhibited antiinflammatory NO-production inhibition activity with IC 50 values of less than 5 μM, which was more potent than the nonspecific NOS inhibitor N ω -nitro-L-arginine methyl ester (L-NAME).Taiwanofungus camphoratus (synonym: Ganoderma camphoratum; Antrodia cinnamomea; Antrodia camphorata) (Polyporaceae, Aphyllophorales), is a rare and precious medical fungus in Taiwan and is called a "national treasure of Taiwan".1 Its Chinese name is ZhanKu or Niu-Chang-Chih. The microorganism is parasitic to the inner heart-wood wall of old hollow trunks of Cinnamomum kanehirai Hay. (Lauraceae). The growth rate of natural T. camphoratus in the wild is very slow, and it is difficult to cultivate in a greenhouse, making fruiting bodies expensive to obtain. In traditional Taiwanese folk medicine T. camphoratus has been used as an important health food for treating food, alcohol, and drug intoxication, -methylergost-8,24(28)-diene-3,11-dion-26-oate (21),10 and ergosterol peroxide (22).11 Cytotoxic activity, inhibition of nitric oxide (NO) or reactive oxygen species (ROS) production, and free radical-scavenging activity of the isolates were evaluated in our study. NIH Public Access Results and DiscussionCamphoratin A (1) was obtained as a colorless powder. , suggested a 4-methylergost-8-en-11-one skeleton similar to that of antcin C (16).5 The 3α-OH functionality was deduced by the correlations from H-3 (δ 3.89, 1H, d, J = 1.6 Hz, β-orientation) to C-4 and C-1 and from H 3 -29 to C-3, C-4, and C-5 in the HMBC spectrum of 1. The hydroxy groups attached at C-7 and C-12 were further designated by the correlations from H-7 (δ 4.52, 1H, t, J = 8.4 Hz) to C-6 and C-8 and from H-12 (4.44, 1H, s) to C-13, C-14, and C-17, respectively. The C-25 carboxylic functionality was assigned due to the presence of an HMBC correlation from H-25 (δ 3.45, 1H, q, J = 6.8 Hz) to the carbon resonance at δ 176.9. A comparison of the NMR spectroscopic data of 1 with those of 165 confirmed the above elucidation and unambiguously established the structure of 1. The relative configuration of 1 was determined by the NOE correlations observed in a NOESY experiment. In the NOESY spectrum of 1, H-7 showed NOE enhancements with both H-5 and H-14, suggesting that these protons had α-orientations. Furthermore, NOE correlations between H-3 and H-4 as well as between H-12 and H 3 -18 disclosed that these protons are β-oriented.Camphoratin B (2) was obtained as a colorless syrup. The HRESIMS of 2 gave an [M + Na] + peak at m/z 495.3089 ...

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Sterol analysis of DMI-resistant and -sensitive strains of Venturia inaequalis

Cited by 65 publications

References 10 publications

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

A new eremophilane-type sesquiterpene from the phytopatogen fungus Lasiodiplodia theobromae (Sphaeropsidaceae)

Antifungal Polyketides and Other Compounds from Amazonian Endophytic Talaromyces Fungi

Camphoratins A−J, Potent Cytotoxic and Anti-inflammatory Triterpenoids from the Fruiting Body of Taiwanofungus camphoratus

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