New Duclauxamide from <i>Penicillium manginii</i> YIM PH30375 and Structure Revision of the Duclauxin Family

Cao, Ping; Yang, Jing; Miao, Cui‐Ping; Yan, Yijun; Ma, Yue; Li, Xiaonian; Zhao, Li‐Xing; Huang, Sheng‐Xiong

doi:10.1021/acs.orglett.5b00081

Cited by 47 publications

(38 citation statements)

References 35 publications

(18 reference statements)

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“…While oxaphenalenones have been previously obtained from Talaromyces species, talaromycesone B ( 18 ) represents the first 1-nor oxaphenalenone dimer carbon skeleton from a natural source. It should be noted, that, although Cao et al [ 57 ] determined an S -configuration at C-9′ and made a generalizing conclusion that duclauxin and its analogues have this S -configuration, such a generalization is problematic and biosynthetically both epimers may be formed. This has to be taken into consideration with the structures of talaromycesone A and B ( 17 and 18 ).…”

Section: New Metabolites From Marine Fungimentioning

confidence: 99%

Natural Products from Marine Fungi—Still an Underrepresented Resource

2016

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Marine fungi represent a huge potential for new natural products and an increased number of new metabolites have become known over the past years, while much of the hidden potential still needs to be uncovered. Representative examples of biodiversity studies of marine fungi and of natural products from a diverse selection of marine fungi from the author’s lab are highlighting important aspects of this research. If one considers the huge phylogenetic diversity of marine fungi and their almost ubiquitous distribution, and realizes that most of the published work on secondary metabolites of marine fungi has focused on just a few genera, strictly speaking Penicillium, Aspergillus and maybe also Fusarium and Cladosporium, the diversity of marine fungi is not adequately represented in investigations on their secondary metabolites and the less studied species deserve special attention. In addition to results on recently discovered new secondary metabolites of Penicillium species, the diversity of fungi in selected marine habitats is highlighted and examples of groups of secondary metabolites produced by representatives of a variety of different genera and their bioactivities are presented. Special focus is given to the production of groups of derivatives of metabolites by the fungi and to significant differences in biological activities due to small structural changes.

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Section: New Metabolites From Marine Fungimentioning

confidence: 99%

Natural Products from Marine Fungi—Still an Underrepresented Resource

2016

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“…14 10 is then proposed to be asymmetrically reduced to the dihydrocoumarin-containing SF226 ( 11 ) 15 , a compound reported from Penicillium purpurogenum , followed by dimerization, methylation and acylation to yield 12 . An additional dehydrogenation across C 1’ -C 9a’ of 12 affords 1 (Figure 2A) 6 . However, the exact sequence of redox modifications and enzymatic basis of these proposed reactions have not been resolved.…”

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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“…occurring in the renowned insecticidal plant Melia azedarach . Duclauxamide A1 ( 42 , Figure 7 ) was purified from the endophytic Penicillium manginii inhabiting the elder root of the traditional Chinese medicinal (TCM) plant Panax notoginseng by the Huang group [ 59 ]. As a polyketide-derived heptacyclic oligophenalenone dimer with an uncommon N -2-hydroxyethyl moiety [ 60 ], compound 42 demonstrated moderate cytotoxicity against HL-60, SMML-7721, A-549, MCF-7, and SW480 cancer cell lines with IC 50 values ranging from 11 to 32 μM.…”

Section: Polyketidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes

Han

Lou

2018

Molecules

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Exploration of structurally novel natural products greatly facilitates the discovery of biologically active pharmacophores that are biologically validated starting points for the development of new drugs. Endophytes that colonize the internal tissues of plant species, have been proven to produce a large number of structurally diverse secondary metabolites. These molecules exhibit remarkable biological activities, including antimicrobial, anticancer, anti-inflammatory and antiviral properties, to name but a few. This review surveys the structurally diverse natural products with new carbon skeletons, unusual ring systems, or rare structural moieties that have been isolated from endophytes between 1996 and 2016. It covers their structures and bioactivities. Biosynthesis and/or total syntheses of some important compounds are also highlighted. Some novel secondary metabolites with marked biological activities might deserve more attention from chemists and biologists in further studies.

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New Duclauxamide from Penicillium manginii YIM PH30375 and Structure Revision of the Duclauxin Family

Cited by 47 publications

References 35 publications

Natural Products from Marine Fungi—Still an Underrepresented Resource

Natural Products from Marine Fungi—Still an Underrepresented Resource

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

Structural Diversity and Biological Activities of Novel Secondary Metabolites from Endophytes

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