Acetoxydehydroaustin, a New Bioactive Compound, and Related Compound Neoaustin from<i>Penicillium</i>sp. MG–11

Hayashi, Hideo; Mukaihara, Manabu; Murao, Sawao; Arai, Motoo; Lee, Angela Y.; Clardy, Jon

doi:10.1271/bbb.58.334

Cited by 59 publications

(51 citation statements)

References 5 publications

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“…18 Although most of the physical and spectral data collected by us were in good agreement with those reported for 1-3, 18 some ambiguous chemical shift assignments were clarified by our 2D NMR studies. The HMBC experiments detected long-range correlations of H-13 with the C-5 and C-10 carbons and of H-1' with the C-2', C-3'and C-7' carbons.…”

Section: Resultssupporting

confidence: 82%

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Structures of meroterpenes produced by Penicillium sp, an endophytic fungus found associated with Melia azedarach

Santos¹,

Rodrigues‐Filho²

2003

J. Braz. Chem. Soc.

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O fungo Penicillium sp foi isolado do córtex das raízes de Melia azedarach após a esterilização da superfície de seus tecidos e foi cultivado durante três semanas sobre arroz previamente esterilizado. Um novo meroterpeno, denominado austinoneol, e os meroterpenos já conhecidos 7-β-acetoxi-dehidroaustina, neoaustina e de-hidroaustina foram isolados do extrato metanólico desta cultura. Suas estruturas foram identificadas através de extensivos estudos espectroscópicos, principalmente RMN 1D e 2D, que permitiram ainda a revisão das atribuições de sinais para alguns dos meroterpenos conhecidos.The fungus Penicillium sp was isolated from the root bark of Melia azedarach after surface sterilisation and cultivated for three weeks on sterilised rice. A new meroterpene, named austinoneol, and the known meroterpenes 7-β-acetoxy-dehydroaustin, neoaustin and dehydroaustin were isolated from the methanol extract of this rice culture. Their structures were identified after extensive spectroscopic studies, which also helped on the revision of 1 H and 13 C chemical shift assignment for some of the known meroterpenes.

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Section: Resultssupporting

confidence: 82%

“…18 Due to their relatively high structural complexity, these compounds have been identified mainly by single crystal X-ray diffraction analysis. 18,20 NMR data, which has been used only for identity confirmation, has not been carefully studied yet.…”

Section: Resultsmentioning

confidence: 99%

Structures of meroterpenes produced by Penicillium sp, an endophytic fungus found associated with Melia azedarach

Santos¹,

Rodrigues‐Filho²

2003

J. Braz. Chem. Soc.

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“…The other known compounds isolated from P. kongii including pebrolide (Mccorkindale et al 1981) ( 2 ), 1-deoxypebrolide (Mccorkindale et al 1981) ( 3 ), asperphenamate (McCorkindale et al 1978) ( 4 ), N-benzoyl-phenylalaninol (McCorkindale et al 1978) ( 8 ), orsellinic acid (Fang et al 2012) ( 9 ), mycophenolic acid (Makara et al 1996) ( 10 ), and 5, 7-dihydroxy-4-methylphthalide (Fujimoto et al 1999) ( 11 ), and the other known compounds isolated from P. brasilianum including 12, 13-dihydroxyfumitremorgin C (Inokoshi et al 2013) ( 12 ), verruculogen (Afiyatullov et al 2004) ( 13 ), viridicatumtoxin (Inokoshi et al 2013) ( 14 ), dehydroaustin (Hayashi et al 1994) ( 15 ), austinolide (Lo et al 2012) ( 16 ), neoaustin (Hayashi et al 1994) ( 17 ), brasiliamide A (Fujita et al 2002) ( 18 ), brasiliamide C (Fujita & Hayashi 2004) ( 19 ), and aspterric acid (Shimada et al 2002) ( 20 ), were determined by comparison of those reported spectroscopic data. Among these, aspterric acid is reported from P. brasilianum for the first time.…”

Section: Resultsmentioning

confidence: 99%

Chemical diversity from the Tibetan Plateau fungi Penicillium kongii and P. brasilianum

Liu

et al. 2017

Mycology

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Two new secondary metabolites, kongiilines A and B (1, 7), and two asperphenamate derivatives, asperphenamates B and C (5–6), together with 16 known compounds (2–4, 8–20), were isolated from Tibetan Plateau fungi Penicillium kongii and Penicillium brasilianum. This is the first report on asperphenamates B and C as naturally occurring compounds, and that aspterric acid is isolated from P. brasilianum for the first time. Their structures were elucidated by different spectroscopic techniques including high-resolution electrospray ionisation mass spectrum, 1D nuclear magnetic resonance (NMR), and 2D NMR as well as electronic circular dichroism. Compounds 4, 5, and 10 exhibited cytotoxicity activities against human colon carcinoma HCT116 cell line with IC50 values of 88.16, 77.68, and 36.92 μM, respectively. Fungi from Tibetan Plateau represent important and rich resources for the investigation of new chemicals.

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“…2). 34) Two more compounds, austinol (43) and dehydroaustinol (44), were also identified together with a new compound named neoaustin (45) (Fig. 2).…”

Section: Austinsmentioning

confidence: 99%

“…2). 34) Members of the austin family are considered to be meroterpenoids, and 45 appears to be a key metabolite in austin biogenesis.…”

Section: Austinsmentioning

confidence: 99%

Frontier studies on highly selective bio-regulators useful for environmentally benign agricultural production

Hayashi

2015

Bioscience, Biotechnology, and Biochemistry

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Fungal metabolites active for insects were obtained from fermentation products using okara media. The mechanisms of action of these compounds against insects were clarified using voltage clamp electrophysiology. The branching factor inducing hyphal branching in arbuscular mycorrhizal (AM) fungi was isolated from the root exudates of Lotus japonicus and identified as 5-deoxystrigol. Strigolactones were originally identified as seed germination stimulants of parasitic weeds; therefore, synthetic strigolactones were developed to exhibit the inducing activity of hyphal branching in AM fungi and diminish the stimulating activity of seed germination of parasitic weeds. Signaling molecules, acylhomoserine lactones (AHLs), in quorum sensing were identified in the fungal strain Mortierella alpina A-178, and the true producer of AHLs was clarified as symbiotic bacteria in the fungus. Since acyl-(S)-adenosylmethionine analogs may be good candidates for competitive inhibitors of AHL synthases, intermediate mimics in the biosynthesis of AHLs have been synthesized.

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Acetoxydehydroaustin, a New Bioactive Compound, and Related Compound Neoaustin fromPenicilliumsp. MG–11

Cited by 59 publications

References 5 publications

Structures of meroterpenes produced by Penicillium sp, an endophytic fungus found associated with Melia azedarach

Structures of meroterpenes produced by Penicillium sp, an endophytic fungus found associated with Melia azedarach

Chemical diversity from the Tibetan Plateau fungi Penicillium kongii and P. brasilianum

Frontier studies on highly selective bio-regulators useful for environmentally benign agricultural production

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