Circumdatin I, a New Ultraviolet-A Protecting Benzodiazepine Alkaloid from a Marine Isolate of the Fungus Exophiala

Zhang, Dahai; Yang, Xiudong; Kang, Jung Sook; Choi, Hong Dae; Son, Byeng Wha

doi:10.1038/ja.2008.108

Cited by 54 publications

(34 citation statements)

References 9 publications

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“…The tandem iterative utilization of the nonproteinogenic anthranilate in the asperlicin pathway, and related pathways builds a unique tetracyclic core scaffold that can be further elaborated to architectural complexity in related scaffolds seen in the benzomalvins, 17–18 circumdatins, 19–22 and sclerotigenin. 23 …”

mentioning

confidence: 99%

Assembly of Asperlicin Peptidyl Alkaloids from Anthranilate and Tryptophan: A Two-Enzyme Pathway Generates Heptacyclic Scaffold Complexity in Asperlicin E

Haynes

Gao²,

Tang³

et al. 2012

J. Am. Chem. Soc.

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Members of the asperlicin family of fungal metabolites produced by Aspergillus alliaceus are known potent CCKA antagonists. Herein we report the identification of the gene cluster responsible for directing their biosynthesis. We validate and probe the pathway by genetic manipulation, and provide the first biochemical characterization of the oxidative cyclization en route to the heptacyclic asperlicin E by reconstituting the activity of the FAD depend monooxygenase AspB. This report provides the first genetic characterization of a NRPS assembly line that efficiently activates two anthranilate building blocks and illustrates the remarkably efficient biosynthesis of the complex heptacyclic asperlicin E.

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mentioning

confidence: 99%

Assembly of Asperlicin Peptidyl Alkaloids from Anthranilate and Tryptophan: A Two-Enzyme Pathway Generates Heptacyclic Scaffold Complexity in Asperlicin E

Haynes

Gao²,

Tang³

et al. 2012

J. Am. Chem. Soc.

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“…[8]; and circumdatins A–I isolated from Aspergillus ochraceus [18–21] and Exphiala sp. [22]. These alkaloids which have been recently reported as natural products consist of two anthranilic acids and a l -amino acid ( e.g.…”

Section: Resultsmentioning

confidence: 99%

Quinazolinobenzodiazepine Derivatives, Novobenzomalvins A–C: Fibronectin Expression Regulators from Aspergillus novofumigatus

Ishikawa

Hosoe²,

Itabashi³

et al. 2011

Sci. Pharm.

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Three new quinazolinobenzodiazepine derivatives, novobenzomalvins A (1), B (2), and C (3), have been isolated as fibronectin expression regulators from Aspergillus novofumigatus CBS117520. The structures of 1 to 3 were established by spectroscopic and physicochemical analysis, and chemical investigation including the total synthesis of 1. Treatment with novo-benzomalvins A (1), B (2), C (3), and N-methylnovobenzomalvin A (5) increased the expression of fibronectin in normal human neonatal dermal fibroblast cells.

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“…Circumdatin I, C and G have been isolated from the mycelium of a marine fungus of the genus Exophiala . These compounds showed high UV-A screening activity, exhibiting ED50 (i.e., effective dose for 50% of the tests) values of 98, 101 and 105 μM, and were more efficient of oxybenzone (ED50, 350 μM) than is currently used sunscreen filter [36]. …”

Section: Photo-protective Compoundsmentioning

confidence: 99%

Marine Microbial-Derived Molecules and Their Potential Use in Cosmeceutical and Cosmetic Products

Corinaldesi

Barone

Marcellini³

et al. 2017

Marine Drugs

150

124

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The oceans encompass a wide range of habitats and environmental conditions, which host a huge microbial biodiversity. The unique characteristics of several marine systems have driven a variety of biological adaptations, leading to the production of a large spectrum of bioactive molecules. Fungi, fungi-like protists (such as thraustochytrids) and bacteria are among the marine organisms with the highest potential of producing bioactive compounds, which can be exploited for several commercial purposes, including cosmetic and cosmeceutical ones. Mycosporines and mycosporine-like amino acids, carotenoids, exopolysaccharides, fatty acids, chitosan and other compounds from these microorganisms might represent a sustainable, low-cost and fast-production alternative to other natural molecules used in photo-protective, anti-aging and skin-whitening products for face, body and hair care. Here, we review the existing knowledge of these compounds produced by marine microorganisms, highlighting the marine habitats where such compounds are preferentially produced and their potential application in cosmetic and cosmeceutical fields.

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Circumdatin I, a New Ultraviolet-A Protecting Benzodiazepine Alkaloid from a Marine Isolate of the Fungus Exophiala

Cited by 54 publications

References 9 publications

Assembly of Asperlicin Peptidyl Alkaloids from Anthranilate and Tryptophan: A Two-Enzyme Pathway Generates Heptacyclic Scaffold Complexity in Asperlicin E

Assembly of Asperlicin Peptidyl Alkaloids from Anthranilate and Tryptophan: A Two-Enzyme Pathway Generates Heptacyclic Scaffold Complexity in Asperlicin E

Quinazolinobenzodiazepine Derivatives, Novobenzomalvins A–C: Fibronectin Expression Regulators from Aspergillus novofumigatus

Marine Microbial-Derived Molecules and Their Potential Use in Cosmeceutical and Cosmetic Products

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