The isolation and structure of two new indole derivatives from Penicillium cyclopium westling

Holzapfel, Cedric W.; Hutchison, R.D.; Wilkins, D.C.

doi:10.1016/s0040-4020(01)98733-2

Cited by 62 publications

(46 citation statements)

References 4 publications

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“…Eight compounds (Figure 1) including kojic acid (1) (Basappa et al,1970), aflatoxin B1 (2) (Basappa et al,1970;Van,1970), maculosin1(3) (Stierle et al, 1988;Rudi and Kashman,1994), hexahydro-3-(4-hydroxybenzyl) pyrrolo[1,2-a]pyrazine-1,4-dione (4) (De Rosa et al, 2003), cyclopiazonic acid (5) (Holzapfel and Hutchison, 1970), cyclopiazonic acid imine (6) (Holzapfel and Hutchison, 1970), aspergillic acid (7) (Dutcher, 1947;Wilson, 1966;Perry et al) and hydroxyaspergillic acid (8) (Wilson, 1966;Perry et al, 1984;Dutcher, 1958) were isolated and purified from the ethyl acetate (EtOAc) extract of CZYB saline culture. These compounds have reported biological activities; cytotoxic, antibacterial, antifungal and pesticide properties (Basappa et al,1970;Van,1970;Stierle et al, 1988;Rudi and Kashman,1994;De Rosa et al, 2003;Holzapfel and Hutchison, 1970;Dutcher, 1947;Wilson, 1966;Perry et al;Dutcher, 1958;Bobylev et al,1996).…”

Section: Results and Discusionmentioning

confidence: 99%

“…These compounds have reported biological activities; cytotoxic, antibacterial, antifungal and pesticide properties (Basappa et al,1970;Van,1970;Stierle et al, 1988;Rudi and Kashman,1994;De Rosa et al, 2003;Holzapfel and Hutchison, 1970;Dutcher, 1947;Wilson, 1966;Perry et al;Dutcher, 1958;Bobylev et al,1996). Extraction of the eight saline culture media of A. flavus with organic solvents and bioassay of the obtained crude extracts showed a significant effect of the nutritional environment on the produced secondary metabolites (Table 1-2, Figures 3-5).…”

Section: Results and Discusionmentioning

confidence: 99%

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Comparative Study of the Secondary Metabolites of Sponge-derived Aspergillus flavus

Tawfik

Mesbah

Khalifa

et al. 2017

Records of Pharmaceutical and Biomedical Sciences

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The fungal sources of novel metabolites have broadened from saprophytic terrestrial strains to marine habitats and living plants with their endophytes. Specifically, metabolites isolated from species of genus Aspergillus have continually attracted the interest of pharmacologists due to their broad array of biological activities and their structural diversity. Bioassay guided fractionation of the extract of saline culture of marine-derived Aspergillus flavus led to the isolation of eight compounds; kojic acid (1), aflatoxin B1 (2), maculosin1 (3), hexahydro-3-(4-hydroxybenzyl)pyrrolo[1,2-a]pyrazine-1,4-dione (4), cyclopiazonic acid (5), cyclopiazonic acid imine (6), aspergillic acid (7) and hydroxyaspergillic acid (8). Structure elucidation of the compounds was based on dereplication using NMR and MS data. A cultivation-based approach was employed to compare the secondary metabolites diversity associated with A. flavus in eight sea water culture media. The type of medium exhibited a significant difference in the yield and the chemistry of compounds responsible for biological activities of the corresponding extract.

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Section: Results and Discusionmentioning

confidence: 99%

Section: Results and Discusionmentioning

confidence: 99%

Comparative Study of the Secondary Metabolites of Sponge-derived Aspergillus flavus

Tawfik

Mesbah

Khalifa

et al. 2017

Records of Pharmaceutical and Biomedical Sciences

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“…64 CPA is an indole tetramic acid that was first isolated from P. cyclopium as a toxic metabolite in 1968. 65 CPA inhibits sarcoplasmic reticulum Ca 2+ -ATPases, 66 and it is known that inhibition of Ca 2+ -ATPases results in cell death through apoptotic pathways within the endoplasmic reticulum and the mitochondria. 67 In addition to Penicillium species several other fungi including the Aspergillus species have been reported to produce CPA, 68,69 whose contamination of agricultural products, such as maize, corn and peanut, is a serious economic and health problem.…”

Section: Solanapyrone Biosynthesis Gene Clustermentioning

confidence: 99%

Functional analysis of fungal polyketide biosynthesis genes

Fujii

2010

J Antibiot

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Fungal polyketides have huge structural diversity from simple aromatics to highly modified complex reduced-type compounds. Despite such diversty, single modular iterative type I polyketide synthases (iPKSs) are responsible for their carbon skeleton construction. Using heterologous expression systems, we have studied on ATX, a 6-methylsalicylic acid synthase from Aspergillus terreus as a model iPKS. In addition, iPKS functions involved in fungal spore pigment biosynthesis were analyzed together with polyketide-shortening enzymes that convert products of PKSs to shorter ketides by hydrolytic C-C bond cleavage. In our studies on reducing-type iPKSs, we cloned and expressed PKS genes, pksN, pksF, pksK and sol1 from Alternaria solani. The sol gene cluster was found to be involved in solanapyrone biosynthesis and sol5 was identified to encode solanapyrone synthase, a Diels-Alder enzyme. Our fungal PKS studies were further extended to identify the function of PKS-nonribosomal peptide synthase involved in cyclopiazonic acid biosynthesis.

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“…Several structurally related natural products have been identified (Figure 1): iso‐α‐cyclopiazonic acid ( 2 ),3 α‐CPA imine ( 3 ),1b speradines A–D,4 and aspergillines A–E,5 all sharing a 3‐acetyltetramic acid unit. …”

mentioning

confidence: 99%

“…Biosynthetically, α‐CPA is derived from l ‐tryptophan (Figure 1 B) 1a,1b, 6. The tetramic acid is assembled at an early stage followed by several alkylations to give β‐cyclopiazonic acid (β‐CPA, 4 ), a direct biosynthetic precursor of α‐CPA.…”

mentioning

confidence: 99%

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

et al. 2018

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A convergent, nine‐step (LLS), enantioselective synthesis of α‐cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)‐cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N−O cleavage of a bromoisoxazole.

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The isolation and structure of two new indole derivatives from Penicillium cyclopium westling

Cited by 62 publications

References 4 publications

Comparative Study of the Secondary Metabolites of Sponge-derived Aspergillus flavus

Comparative Study of the Secondary Metabolites of Sponge-derived Aspergillus flavus

Functional analysis of fungal polyketide biosynthesis genes

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

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