Cytotoxicity and genotoxicity of xenoclauxin and desacetyl duclauxin fromPenicillium Duclauxii (delacroix)

Kawai, Kiyoshi; Shiojiri, Hiroyuki; Nakamaru, T.; Nozawa, Yoshinori; Sugie, Shigeyuki; Mori, Hideki; Kato, Takeshi; Ogihara, Yukio

doi:10.1007/bf00717786

Cited by 25 publications

(19 citation statements)

References 12 publications

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“…Duclauxin, another fungal secondary metabolite, was isolated from sporulating Penicillium herquei grown on a medium of peanut hulls supplemented with potato starch solution, and it exhibited antitumor activity [65,66].…”

Section: Immunotoxins Of Fungal Originmentioning

confidence: 99%

Fungal Secondary Metabolites: A Promising Source of Antineoplastic Drugs

Ahmed¹,

Shikh²,

Ghoneimy³

et al. 2010

CCTR

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The rapid progress in understanding the molecular biology of cancer has made a large impact on the design and development of novel therapeutic strategies prompted by the multi-factorial limitations of the current chemotherapeutic modalities. Given that the development of newer antineoplastic drugs continues to rely heavily on isolation from natural sources rather than applications based on rational drug design and combinatorial chemistry, fungal secondary metabolites rank high on the list of potential targets for the discovery of novel chemotherapeutic agents. They represent a diverse group of bioactive compounds characterized by their origin and biosynthetic pathways. Also, they serve as regulators, chemical messengers in developmental processes, or as antibiotics. A broad variety of fungal secondary metabolites possess potent antitumor activity. Alpha sarcin, gliotoxins, trichodimerol, L-lysine alpha-oxidase, fumagillin, declauxin, chrysanthones, fungal-derived low molecular weight inhibitors of angiogenesis e.g. TNP-470, retamycin, daunorubicin, and doxorubicin all have been shown to exert potent antitumor activity. Inhibition of protein synthesis, induction of DNA breakage and apoptosis, as well as blockade of angiogenesis are examples of the multiple antitumor mechanisms of fungal secondary metabolites. The current review explores the potential use of fungal secondary metabolites as antineoplastic drugs with special reference to the novel hepatoma growth-inhibition factor that we recently characterized from Trichoderma viride.

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Section: Immunotoxins Of Fungal Originmentioning

confidence: 99%

Fungal Secondary Metabolites: A Promising Source of Antineoplastic Drugs

Ahmed¹,

Shikh²,

Ghoneimy³

et al. 2010

CCTR

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“…One pigment component found in Polygonum cuspidatum Sieb. et Zucc., 1,3,8-trihydroxy-6-methylanthraquinone, is known as emodin and exhibits a variety of potent biological effects such as inhibition of growth of the murine leukemia virus (Kawai et al, 1984), antimicrobial activity (Brown, 1980), an immunosuppressive effect (Huang et al, 1992) and vasorelaxant activity Huang, Lee et al, 1991). We report here the structure of the monohydrate, (I),…”

Section: Commentmentioning

confidence: 99%

1,3,8-Trihydroxy-6-methylanthraquinone monohydrate

Zhu

Wang

et al. 2006

Acta Cryst E

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The title compound, C15H10O5·H2O, also known as emodin monohydrate, was isolated from the roots of Polygonum cuspidatum Sieb. et Zucc. It is an anthraquinone derivative, and all of its non‐H atoms are essentially coplanar. Intramolecular O—H⋯O hydrogen bonds and intermolecular O—H⋯O and C—H⋯O hydrogen bonds are observed in this crystal form. The crystal structure is further stabilized by weak π–π interactions and hydrogen bonds to the water molecule.

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“…6,7 Duclauxins have diverse biological activities. 7–9 For example, duclauxin ( 1 ) and cryptoclauxin ( 2 ) exhibit tumor suppression by inhibiting RNA synthesis or mitochondrial ATP synthesis, 10, 11 and talaromycesone B ( 3 ) is an inhibitor of acetylcholinesterase. 12 Structural variations among duclauxins are attributed to different oxaphenalenone monomers and connectivities between them (Figures 1 and S1).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide

et al. 2018

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Duclauxins are dimeric and heptacyclic fungal polyketides with notable bioactivities. We characterized the cascade of redox transformations in the biosynthetic pathway of duclauxin from Talaromyces stipitatus. The redox reaction sequence is initiated by a cupin family dioxygenase DuxM that performs an oxidative cleavage of the peri-fused tricyclic phenalenone and affords a transient hemiketal-oxaphenalenone intermediate. Additional redox enzymes then morph the oxaphenoalenone into either an anhydride or a dihydrocoumarin-containing monomeric building block that is found in dimeric duxlauxins. Oxidative coupling between the monomers to form the initial C-C bond was shown to be catalyzed by a P450 monooxygenase, although the enzyme responsible for the second C-C bond formation was not found in the pathway. Collectively, the number and variety of redox enzymes used in the duclauxin pathway showcase Nature's strategy to generate structural complexity during natural product biosynthesis.

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Cytotoxicity and genotoxicity of xenoclauxin and desacetyl duclauxin fromPenicillium Duclauxii (delacroix)

Cited by 25 publications

References 12 publications

Fungal Secondary Metabolites: A Promising Source of Antineoplastic Drugs

Fungal Secondary Metabolites: A Promising Source of Antineoplastic Drugs

1,3,8-Trihydroxy-6-methylanthraquinone monohydrate

Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide

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