Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities

Cardoso-Martínez, Faviola; Rosa, José M. de la; Dárias, José; Cerella, Claudia; Diederich, Marc; Cueto, Mercedes

doi:10.1039/c5ob00773a

Cited by 33 publications

(36 citation statements)

References 30 publications

(72 reference statements)

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“…3). The nal renement on the Cu/Ka data resulted in a Flack parameter of 0.00 (2), allowing an assignment of the absolute conguration as 2R. Based on the above discussion, the structure of compound 2 was elucidated and the trivial name penicibrocazine G was assigned.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3] However, mining of microbial genomes revealed the presence of numerous silent metabolite gene clusters in a single microbe, displaying underestimated metabolic potentials, which are not always expressed under common laboratory culture conditions. 4 The "one strain-many compounds (OSMAC)" approach, introduced by Zeeck and co-workers, has been successfully applied to increase the chemical diversity and the yield of new secondary metabolites from a single microbial strain, in which the promising strain is cultured in a variety of media and/or under different culture conditions.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Antimicrobial alkaloids produced by the mangrove endophyte Penicillium brocae MA-231 using the OSMAC approach

Meng

Liu

et al. 2017

RSC Adv.

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The OSMAC (one strain-many compounds) protocol was used in this study to obtain various metabolites from the mangrove-derived endophytic fungus Penicillium brocae MA-231. As a result, four new thiodiketopiperazine alkaloids, penicibrocazines F-I (1-4), together with two new N-containing p-hydroxyphenopyrrozin derivatives brocapyrrozins A and B (7 and 8) as well as six known alkaloids (5, 6, and 9-12), were identified from the extract of the Czapek culture medium of the fungus. Their structures and absolute configurations were determined through interpretation of their spectroscopic data and by X-ray crystallographic analysis. Compounds 7 and 9 exhibited potent activity against human pathogenic bacterium Staphylococcus aureus with MIC values of 0.125 and 0.5 mg mL À1, respectively.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antimicrobial alkaloids produced by the mangrove endophyte Penicillium brocae MA-231 using the OSMAC approach

Meng

Liu

et al. 2017

RSC Adv.

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“…These changes include altering the composition of media or changing some factors such as light, temperature, aeration, culture vessels’ shape and even the type and contents of water which is used for culturing of these fungi . Tanzawaic acids belong to decalin polyketide class of compounds and their biosynthesis was extensively discussed in many reports in the literature . These decalin polyketides (tanzawaic acids) proved to possess several biological activities such as antibacterial, antioxidant, cytotoxic and antifungal activities as established by Tominaga and co‐workers .…”

Section: Introductionmentioning

confidence: 99%

A New Antioxidant Decalin Polyketide from Freshwater‐Sediment‐Derived Fungus Penicillium sp. Strain S1a1

Ebada

Ebrahim

2019

ChemistrySelect

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Chromatographic workup for EtOAc (ethyl acetate) extract of an OSMAC (One Strain MAny Compounds)‐modified solid rice culture of the freshwater‐sediment‐derived fungus, Penicillium sp. (S1a1), afforded one new decalin polyketide derivative, tanzawaic acid Z1 (1). The chemical structure of the new derivative was unambiguously established based on extensive 1D (one‐) and 2D (two‐dimensional) NMR (Nuclear Magnetic Resonance) spectroscopic data along with ESI‐HRMS (ElectroSpray Ionization‐High Resolution Mass Spectrometry). Moreover, the relative configuration was determined based on NMR spectroscopic data including a ROESY (Rotational Overhauser Effect SpectroscopY) spectrum. The absolute configuration was suggested on the basis of the specific optical rotation, and biogenetic considerations in comparison with related previously isolated known metabolites from the same fungal strain. In addition, the antioxidant, antibacterial and cytotoxic activities of the new derivative were evaluated. Compound 1 proved to exert a promising antioxidant activity.

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“…However, analysis of HMBC data ( to display any biological activity. 191 Additionally, there are several other reports in the literature on members of this compound class. Their structures differ primarily by oxidation and substitution pattern of the decalin ring, while in some cases aromatization of one of the decalin rings has been reported as well.…”

Section: 13mentioning

confidence: 99%

“…Therefore, the antiinsectan activity shown by the crude extract against the fall armyworm was most probably caused by some simple aromatic compounds that were not purified further. Alternatively, the isolated known compound 8,9dehydroneoxaline 160 could be responsible for this activity, even though there are no reports of antiinsectan activity for this compound.Notably, after the work described here was completed, a report emerged in 2015, describing isolation of several tanzawaic acids, including tanzawaic acid O,191 the structure of which is equivalent to that of hynapene D (3.10). Tanzawaic acid O and related metabolites described in this literature report were discovered from a marinederived isolate of an unidentified Penicillium sp 191.…”

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confidence: 99%

Chemical investigations of fungicolous and coprophilous fungi

Jayanetti¹

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Dement is specially mentioned for always cheering me up, for his liveliness, and for all the pep talks. I also really value all the nice times spent with In Hyun, Nicole, and Nick. My eternal love Chethya is specially mentioned for always being by my side, for all the encouragement and motivation, and for all the amazing times that were spent and will be spent together. All my friends in Iowa City deserve a special recognition for their amazing friendship and helping me through tough times, and the Iowa Sri Lankan family for always being there for me, for their continuous support, and for all the lovely times we spent together. The constant moral support and strength given to me by my family and friends back in Sri Lanka are highly appreciated. I also cherish all the yacking sessions we had online, which took all the stress of graduate school away from me. Last but not the least, my mother for all her sacrifices, commitments, and dedication in bringing me up and shaping me in to a respectable citizen after I lost my father at the age of 10. I don't think I will ever be able to repay her for everything she has done for me. I am the person I am today purely because of her and I can't thank her enough for that. She is and will be the pillar of strength of my life forever! v ABSTRACT Fungi are renowned for their ability to produce a wide array of secondary metabolites with unique and diverse structures. Some of these compounds possess important biological activities, which make them useful agents in medicine for treatment of various diseases or in agriculture for control/elimination of pests and pathogens of economically important crops. However, there still remains great untapped potential in the fungal kingdom as only about 100,000 species have been formally described out of approximately 1.5 million species that exist. Many fungi are fairly ubiquitous in soil or other common substrates, while others belong to more specific niche groups and are categorized as marine, freshwater, endophytic, fungicolous/mycoparasitic, or coprophilous, or with other descriptors, based on their ecological origin. Some of these niche groups, such as marine and endophytic fungi, have been commonly studied in recent years, while others, including coprophilous fungi, remain relatively underexplored. Studies on these underexplored groups could potentially yield more new and structurally unique compounds with important biological activities. Different research groups

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Tanzawaic acids isolated from a marine-derived fungus of the genus Penicillium with cytotoxic activities

Cited by 33 publications

References 30 publications

Antimicrobial alkaloids produced by the mangrove endophyte Penicillium brocae MA-231 using the OSMAC approach

Antimicrobial alkaloids produced by the mangrove endophyte Penicillium brocae MA-231 using the OSMAC approach

A New Antioxidant Decalin Polyketide from Freshwater‐Sediment‐Derived Fungus Penicillium sp. Strain S1a1

Chemical investigations of fungicolous and coprophilous fungi

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