Trichocladinols A–C, Cytotoxic Metabolites from a <i>Cordyceps</i>‐Colonizing Ascomycete <i>Trichocladium opacum</i>

Guo, Huijuan; Sun, Bing-Da; Gao, Hao; Niu, Shubin; Liu, Xingzhong; Yao, Xin‐Sheng; Che, Yongsheng

doi:10.1002/ejoc.200900735

Cited by 23 publications

(28 citation statements)

References 23 publications

(31 reference statements)

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“…5,18 CCDC 734060 contained two conformers of the tris-MTPA ester, in which two MTPA ester moieties belonged to this rare conformer a. 48 The 1 H NMR upfield shift observed at the L 2 substituent of the alcohol moiety [1][2][3] suggested that conformer a was also insignificant in solution (Fig. 2).…”

Section: Database Study Of Mtpa Estersmentioning

confidence: 97%

“…In addition, the intramolecular interactions (e.g., the C-H … p interaction and the C-H … O hydrogen bond) were often observed between the acyl and alcohol moieties in the crystalline MTPA esters in which the ester-carbonyl and trifluoromethyl groups were not syn (e.g., CCDC 282786 45 and CCDC 723548 46 ). Also, note that irregular conformations were frequently observed in the bis-or tris-MTPA esters (e.g., CCDC 292039 47 and CCDC 734060 48 ).…”

Section: Database Study Of Mtpa Estersmentioning

confidence: 99%

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Crystal structures of Mosher's salt and ester elucidated by X-ray crystallography

2013

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Section: Database Study Of Mtpa Estersmentioning

confidence: 97%

Section: Database Study Of Mtpa Estersmentioning

confidence: 99%

Crystal structures of Mosher's salt and ester elucidated by X-ray crystallography

2013

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“…Compound 6 and trichocladinol B ( 14 ) were isolated as a mixture in a 1:1 ratio. Trichocladinol B was identified by comparing the NMR data with those already published . The molecular formula of compound 6 was determined to be C 12 H 16 O 5 by the analysis of its HR-ESIMS spectrum and NMR data.…”

Section: Resultsmentioning

confidence: 99%

“…massarilactone G ( 9 ), palmarumycin CJ-12,371 ( 10 ), palmarumycin CP 2 ( 11 ), palmarumycin CP 19 ( 12 ), massarigenin C ( 13 ), and trichocladinol B ( 14 ) …”

Section: Resultsmentioning

confidence: 99%

Paraverrucsins A–F, Antifeedant, and Antiphytopathogenic Polyketides from Rhizospheric Paraphaeosphaeria verruculosa and Induced Bioactivity Enhancement by Coculturing with Host Plant Dendrobium officinale

Yang

Wang

et al. 2020

ACS Omega

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Six new polyketides named paraverrucsins A−F (1− 6) with oxabicyclic and dioxatricyclic skeletons, together with eight known metabolites (7−14), were discovered and isolated from the fermentation medium of Paraphaeosphaeria verruculosa. Paraverrucsin A−C possessed a novel decarboxylated skeleton compared with that of trichocladinols. Their structures were elucidated by extensive spectral analysis and DP4+ calculations. Paraverrucsins B/C and D/E were isolated as a mixture for the mutarotation occurred at C-2. Paraverrucsins B/C, D/E, F/ trichocladinol B, 8, and 9 displayed antifeedant activities against silkworm larvae, with antifeedant index percentages ranging from 62.5 to 93.0%, at a concentration of 50 μg/cm 2 . Among them, Paraverrucsins B/C and 9 had EC 50 values at 13.9 and 18.2 μg/cm 2 . Most compounds showed antifungal activities against phytopathogenic fungi with minimum inhibitory concentration (MIC) values of 16−64 μg/mL. Coculture of P. verruculosa and host plant Dendrobium officinale leads to the enhancement of antifeedant and antiphytopathogenic activities. Compounds 1, 2/3, 4/5, 6/14 were tested for cytotoxicity against five human carcinoma cell lines, HL-60, A549, MCF-7, SW480, and SMMC-7721, while they exhibited selected cytotoxicity against SW480 with inhibition ratios of 32−38% at a concentration of 40 μM.

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“…20 Additional fungal metabolites containing a core structure similar to oxaspirols include arthropsolides from Arthropsis truncata , 21 massarigenins from Massarina tunicata , 22 spiroleptosphols from Leptosphaeria doliolum , 23 and trichocladinols from Trichocladium opacum . 24 …”

mentioning

confidence: 99%

Oxaspirol B with p97 Inhibitory Activity and Other Oxaspirols from Lecythophora sp. FL1375 and FL1031, Endolichenic Fungi Inhabiting Parmotrema tinctorum and Cladonia evansii

et al. 2016

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A new metabolite, oxaspirol D (4), together with oxaspirols B (2) and C (3) were isolated from Lecythophora sp. FL1375, an endolichenic fungus isolated from Parmotrema tinctorum, whereas Lecythophora sp. FL1031 inhabiting the lichen Cladonia evansii afforded oxaspirols A (1), B (2), and C (3). Of these, oxaspirol B (2) showed moderate p97 ATPase inhibitory activity. A detailed characterization of all oxaspirols was undertaken because structures proposed for known oxaspirols have involved incomplete assignments of NMR spectroscopic data leading only to their planar structures. Thus, the naturally occurring isomeric mixture (2a and 2b) of oxaspirol B was separated as their diacetates (5a and 5b) and the structures and absolute configurations of 1, 2a, 2b, 3, and 4 were determined by the application of spectroscopic techniques including two-dimensional NMR and the modified Mosher's ester method. Oxaspirol B (2) and its diacetates 5a and 5b were evaluated for their ATPase inhibitory activities of p97, p97 mutants, and other ATP-utilizing enzymes, and only 2 was found to be active, indicating the requirement of some structural features in oxaspirols for their activity. Additional biochemical and cellular assays suggested that 2 was a reversible, non-ATP competitive, and specific inhibitor of p97.

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Trichocladinols A–C, Cytotoxic Metabolites from a Cordyceps‐Colonizing Ascomycete Trichocladium opacum

Cited by 23 publications

References 23 publications

Crystal structures of Mosher's salt and ester elucidated by X-ray crystallography

Crystal structures of Mosher's salt and ester elucidated by X-ray crystallography

Paraverrucsins A–F, Antifeedant, and Antiphytopathogenic Polyketides from Rhizospheric Paraphaeosphaeria verruculosa and Induced Bioactivity Enhancement by Coculturing with Host Plant Dendrobium officinale

Oxaspirol B with p97 Inhibitory Activity and Other Oxaspirols from Lecythophora sp. FL1375 and FL1031, Endolichenic Fungi Inhabiting Parmotrema tinctorum and Cladonia evansii

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