2019
DOI: 10.1021/acs.orglett.8b04020
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Isopenicins A–C: Two Types of Antitumor Meroterpenoids from the Plant Endophytic Fungus Penicillium sp. sh18

Abstract: Isopenicins A−C (1−3), three novel meroterpenoids possessing two types of unprecedented terpenoidpolyketide hybrid skeletons, were isolated from the cultures of Penicillium sp. sh18. Their structures were determined through synergetic use of extensive spectroscopic analysis, quantum-chemical calculation with ANN−PRA analysis, and X-ray crystallographic analysis. Additionally, the inhibitory activities of these compounds on the Wnt/β-catenin signaling pathway were evaluated, and 1 was identified as a potent inh… Show more

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Cited by 54 publications
(33 citation statements)
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“…2009 ), penicilliols ( Kimura et al. 2009 ), isopenicins ( Tang et al. 2019b ), andrastin A, antarone A, curvulic acid, gregatins, penicillifuranone A, viomellein, vioxanthin, and xanthomegnin.…”
Section: Resultsmentioning
confidence: 99%
“…2009 ), penicilliols ( Kimura et al. 2009 ), isopenicins ( Tang et al. 2019b ), andrastin A, antarone A, curvulic acid, gregatins, penicillifuranone A, viomellein, vioxanthin, and xanthomegnin.…”
Section: Resultsmentioning
confidence: 99%
“…Over the past several years, our groups have made great efforts to study the secondary metabolites from endophytic fungi inhabiting the Isodon species. As a result, isopenicin A, a potent inhibitor of Wnt signaling [ 18 ], as well as several antineoplastic compounds like phomopchalasins A and B [ 19 ] have been successfully obtained. In the present research, an endophytic fungus colonizing in the stems of Isodon xerophilus was discovered and identified as Arthrinium sp.…”
Section: Introductionmentioning
confidence: 99%
“…Fungal secondary metabolites have always been considered an important source for drug discovery due to their diverse chemical structures and bioactivities [1]. Among them, Penicillium are recognized as important producers of structurally unusual natural products, especially of terpenes with pharmaceutical potential as illustrated with chrysogenester, an anti-inflammatory meroterpenoid-type derivative [2], shearilicine, a cytotoxic indole-diterpenoid possessing a rare carbazole unit [3,4], and the penerpenes, unusual indole-terpenoids which have shown potent protein tyrosine phosphatase inhibitory activity [5].…”
Section: Introductionmentioning
confidence: 99%
“…The EtOAc extract of the fermentation broth showed significant activity against newly hatched larvae of Helicoverpa armigera Hubner. Chemical investigation of the fungus fermentation's organic extract resulted in the isolation of four new xanthene derivatives (1)(2)(3)(4), along with one known compound 5 (Figure 1). Herein, the isolation, structure elucidation, and insecticidal activity of these compounds are described.…”
Section: Introductionmentioning
confidence: 99%