Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Guo, Hua; Feng, Tao; Li, Zhenghui; Liu, Ji‐Kai

doi:10.1007/s13659-012-0088-y

Cited by 12 publications

(5 citation statements)

References 25 publications

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“…Aurovertin U ( 2 ) was also obtained as a yellow amorphous powder, which had the molecular formula C 23 H 30 O 7 based on HR‐ESI‐MS analysis. The IR, UV, and NMR spectra were similar to those of aurovetin K, except for an additional Me group signal and loss a low‐field signal in 2 . The location of the Me(22) group at C(15) was deduced by HMBCs Me(22)/C(14), Me(22)/C(15), and Me(22)/C(16).…”

Section: Resultsmentioning

confidence: 76%

“…Aurovertins are a class of toxic polyketide with the basic structure of 2,6‐dioxabicyclo[3.2.1]octane (DBO) ring system and a conjugated α ‐pyrone moiety. To date, these metabolites had been reported from fungal species like C. arbuscula , Albatrellus confluens , Pochonia chlamydosporia , and Metarhizium anisopliae . Among these isolates, aurovertin T ( 1 ) is structurally like a biosynthetic intermediate , and has different substituted pattern in its α ‐pyrone moiety from the other aurovertins previously reported .…”

Section: Resultsmentioning

confidence: 99%

“…The known compounds were identified as aurovertins B ( 3 ) , D and E ( 4 and 5 ) , and M ( 6 ) by comparing their spectroscopic data with literature data. Aurovertins are a class of toxic polyketide with the basic structure of 2,6‐dioxabicyclo[3.2.1]octane (DBO) ring system and a conjugated α ‐pyrone moiety.…”

Section: Resultsmentioning

confidence: 99%

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Aurovertin‐Type Polyketides from Calcarisporium arbuscula with Potent Cytotoxic Activities against Triple‐Negative Breast Cancer

Zhao

et al. 2016

Helvetica Chimica Acta

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Two new polyene polyketides, namely aurovertins T and U (1 and 2), were isolated from Calcarisporium arbuscula, together with aurovertins B (3), D and E (4 and 5), and M (6). The structures were elucidated by extensive spectroscopic methods (especially 2D-NMR techniques). The cytotoxic activities of all isolates against human triple-negative breast cancer cell line (MDA-MB-231) were evaluated. As a result, compounds 3, 4, and 6 exhibited more potent cytotoxic activities against MDA-MB-231 cell line than the positive control taxol. Also, discussion about the relationships between structure and activity of these aurovertins was presented.

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Section: Resultsmentioning

confidence: 76%

Section: Resultsmentioning

confidence: 99%

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Aurovertin‐Type Polyketides from Calcarisporium arbuscula with Potent Cytotoxic Activities against Triple‐Negative Breast Cancer

Zhao

et al. 2016

Helvetica Chimica Acta

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“…Aurovertins are a class of polyene polyketides featuring an unusual 2,6-dioxabicyclo [3.2.1]-octane ring system from fungal species like Calcarisporium arbuscula , Metarhizium anisopliae , and Albatrellus confluens . − Aurovertin B (AVB) has been revealed to be a specific and uncompetitive inhibitor of ATPase, , and displayed potent cytotoxic and apoptosis inducing activities . ATPase was believed to only occur in mitochondria for a long time.…”

Section: Introductionmentioning

confidence: 99%

Discovery of NO Donor-Aurovertin Hybrids as Dual Ferroptosis and Apoptosis Inducers for Treating Triple Negative Breast Cancer

Ma,

Xu,

Yuan

et al. 2024

J. Med. Chem.

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Triple-negative breast cancer (TNBC) is a highly lethal malignancy, and its clinical management encounters severe challenges due to its high metastatic propensity and the absence of effective therapeutic targets. To improve druggability of aurovertin B (AVB), a natural polyketide with a significant antiproliferative effect on TNBC, a series of NO donor/AVB hybrids were synthesized and tested for bioactivities. Among them, compound 4d significantly inhibited the proliferation and metastasis of TNBC in vitro and in vivo with better safety than that of AVB. The structure−activity relationship analysis suggested that the types of NO donor and the linkers had considerable effects on the activities. Mechanistic investigations unveiled that 4d induced apoptosis and ferroptosis by the reduction of mitochondrial membrane potential and the down-regulation of GPX4, respectively. The antimetastatic effect of 4d was associated with the upregulation of DUSP1. Overall, these compelling results underscore the tremendous potential of 4d for treating TNBC.

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“…To date, 19 aurovertins (A–S) have been obtained and structurally elucidated from soil fungi including important insect- and nematode-associated fungi such as Metarhizium anisopliae and P. chlamydosporia . − During the past three decades this class of yellow pigment metabolites has attracted much interest because aurovertin B binds to the β subunit of the F 1 -ATPase found on the inner membrane of mitochondria, inhibiting the ATPase and thereby uncoupling oxidative phosphorylation in in vitro bioassays . Furthermore, aurovertin B strongly inhibits the proliferation of breast cancer cell lines and arrests cell cycles at the G0/G1 phase …”

Section: Introductionmentioning

confidence: 99%

Yellow Pigment Aurovertins Mediate Interactions between the Pathogenic Fungus Pochonia chlamydosporia and Its Nematode Host

Wang

et al. 2015

J. Agric. Food Chem.

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Nematophagous fungi are globally distributed soil fungi and well-known natural predators of soil-dwelling nematodes. Pochonia chlamydosporia can be found in diverse nematode-suppressive soils as a parasite of nematode eggs and is one of the most studied potential biological control agents of nematodes. However, little is known about the functions of small molecules in the process of infection of nematodes by this parasitic fungus or about small-molecule-mediated interactions between the pathogenic fungus and its host. Our recent study demonstrated that a P. chlamydosporia strain isolated from root knots of tobacco infected by the root-knot nematode Meloidogyne incognita produced a class of yellow pigment metabolite aurovertins, which induced the death of the free-living nematode Panagrellus redivevus. Here we report that nematicidal P. chlamydosporia strains obtained from the nematode worms tended to yield a total yellow pigment aurovertin production exceeding the inhibitory concentration shown in nematicidal bioassays. Aurovertin D was abundant in the pigment metabolites of P. chlamydosporia strains. Aurovertin D showed strong toxicity toward the root-knot nematode M. incognita and exerted profound and detrimental effects on the viability of Caenorhabditis elegans even at a subinhibitory concentration. Evaluation of the nematode mutation in the β subunit of F1-ATPase, together with the application of RNA interference in screening each subunit of F1FO-ATPase in the nematode worms, demonstrated that the β subunit of F1-ATPase might not be the specific target for aurovertins in nematodes. The resistance of C. elegans daf-2(e1370) and the hypersensitivity of C. elegans daf-16(mu86) to aurovertin D indicated that DAF-16/FOXO transcription factor in nematodes was triggered in response to the aurovertin attack. These findings advance our understanding of the roles of aurovertin production in the interactions between nematodes and the pathogen fungus P. chlamydosporia.

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Ten new aurovertins from cultures of the basidiomycete Albatrellus confluens

Cited by 12 publications

References 25 publications

Aurovertin‐Type Polyketides from Calcarisporium arbuscula with Potent Cytotoxic Activities against Triple‐Negative Breast Cancer

Aurovertin‐Type Polyketides from Calcarisporium arbuscula with Potent Cytotoxic Activities against Triple‐Negative Breast Cancer

Discovery of NO Donor-Aurovertin Hybrids as Dual Ferroptosis and Apoptosis Inducers for Treating Triple Negative Breast Cancer

Yellow Pigment Aurovertins Mediate Interactions between the Pathogenic Fungus Pochonia chlamydosporia and Its Nematode Host

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