Isolation and structure determination of pycnidione, A novel bistropolone stromelysin inhibitor from a Phoma sp.

Harris, Guy H.; Hoogsteen, Karst; Silverman, Keith C.; Raghoobar, Susan L.; Bills, Gerald F.; Lingham, Russell B.; Smith, Jack L.; Dougherty, Harry W.; Cascales, Carmen; Peláez, Fernando

doi:10.1016/s0040-4020(01)80357-4

Cited by 62 publications

(57 citation statements)

References 13 publications

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“…The NMR data of pycnidione, mevalonolactone and 7-hydroxy-2-methylchromaonone were identical to those published [1], [2], [3], [4], [5]. The HMBC spectrum of 1 demonstrated the following correlations: H-17 to C-5a and C-6; H-7 to C-5a; H-8 to C-19; H-19 to C-8 and C-9, H-18 to C-8 and C-9, H-10 to C-8, C-9, C-12 and C-19; H-20 to C-11 and C-13; H-14 to C-5a, C-13 and C-15; H-2 to C-1, C-4 and C-16; H-4 to C-2 and C-4a; and H-16 to C-1, C-2 and C-15a.…”

Section: Resultssupporting

confidence: 75%

“…The EtOAc extract of the culture broth of K. pughii was purified by a silica gel column chromatography and crystallization to yield pughiinin A (1), pycnidione (2) [1], mevalonolactone [2], [3], [4], and 7-hydroxy-2-methylchromanone [5]. The NMR data of pycnidione, mevalonolactone and 7-hydroxy-2-methylchromaonone were identical to those published [1], [2], [3], [4], [5].…”

Section: Resultsmentioning

confidence: 99%

“…Pycnidione (2) was previously isolated from Phoma sp. strain MF 5726 collected on Korase Island, Federated States of Micronesia [1] and from the fungus strain OS-F 69 284 collected in Brazil [7]. Pycnidione was reported to inhibit the cleavage of the 3 H-b casein caused by stromelysin, a zinc-containing metalloendoproteinase found in the synovial fluid of patients with rheumatoid arthritis [8].…”

Section: Resultsmentioning

confidence: 99%

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Pughiinin A, a Sesquiterpene from the FungusKionochaeta pughiiBCC 3878

et al. 2002

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A novel secondary metabolite, pughiinin A, together with pycnidione, mevalonolactone, and 7-hydroxy-2-methylchromanone, was isolated from the seed fungus Kionochaeta pughii BCC 3878. The chemical structure was established by spectroscopic methods and by single crystal X-ray crystallography. Pughiinin A and pycnidione exhibited in vitro antiplasmodial activity against Plasmodium falciparum (K1 strain). Pycnidione also showed anti-cancer activity against KB and BC cell lines with the IC 50 values of 2.0 and 1.6 microg/mL, respectively.

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Section: Resultssupporting

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Pughiinin A, a Sesquiterpene from the FungusKionochaeta pughiiBCC 3878

et al. 2002

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“…Pycnidione (180), [87] eupenifeldin (181), [88] and epolone B (182) [89] are a group of recently isolated fungal metabolites that possess identical tropolone rings attached to a sesquiScheme 35. Biosynthetic studies on culantraramine (167).…”

Section: Pycnidione and Othersmentioning

confidence: 99%

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

2003

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Nature's repertoire of biosynthetic transformations has recently been recognized to include the Diels-Alder cycloaddition reaction. Evidence now exists that there are enzymes that mediate the Diels-Alder reaction in secondary metabolic biosynthetic pathways. 2002 marked the 100th anniversary of Alder's birth and 75 years since the discovery of the Diels-Alder reaction. It would appear that living systems discovered and made use of this ubiquitously useful ring-forming reaction eons ago for the construction of complex natural products. In this Review an overview is given of all of the known classes of natural products (polyketides, isoprenoids, phenylpropanoids, alkaloids) that have been speculated to arise by a biological Diels-Alder reaction.

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“…During this screening program, pycnidione (Fig. 1A), a fungal metabolite previously reported to inhibit stromelysin, 23) cell growth, 24) and plasmodial activity, 25) was found to abrogate G2 arrest. In this study, we describe the activity and the mechanism of action of pycnidione as a G2 arrest abrogator.…”

mentioning

confidence: 99%

Potentiation of Bleomycin in Jurkat Cells by Fungal Pycnidione

Kaneko

Matsuda

Ohtawa

et al. 2012

Biological & Pharmaceutical Bulletin

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Most cancer cells have mutations in genes at the G1 checkpoint and repair DNA only in the G2 phase; therefore, the G2 checkpoint is a potential target to develop novel therapy. In the course of screening, a known compound, pycnidione, was isolated from the fungal culture broth of Gloeotinia sp. FKI-3416. Pycnidione irreversibly abrogated bleomycin-induced G2 arrest in Jurkat cells and synergically potentiated the cytotoxicity of bleomycin. To elucidate the mechanism of action, the effect of pycnidione on the signal transduction of the G2 checkpoint was analyzed, showing that the increased phospho-cyclin dependent kinase-1 (CDK1) level caused by bleomycin was abrogated in the presence of pycnidione, indicating that cells did not arrest at the G2 phase. Moreover, under these conditions, Chk1 and Chk2 levels were markedly downregulated. Thus, we concluded that pycnidione abrogated bleomycin-induced G2 arrest by decreasing Chk1 and Chk2.

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Isolation and structure determination of pycnidione, A novel bistropolone stromelysin inhibitor from a Phoma sp.

Cited by 62 publications

References 13 publications

Pughiinin A, a Sesquiterpene from the FungusKionochaeta pughiiBCC 3878

Pughiinin A, a Sesquiterpene from the FungusKionochaeta pughiiBCC 3878

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

Potentiation of Bleomycin in Jurkat Cells by Fungal Pycnidione

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