Penicitols A–C and Penixanacid A from the Mangrove-Derived <i>Penicillium chrysogenum</i> HDN11-24

Guo, Wei-Li; Li, Dan; Peng, Jixing; Zhu, Tianjiao; Gu, Qianqun; Li, Dehai

doi:10.1021/np500586r

Cited by 45 publications

(37 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…19 Cytotoxic (L5178Y: 26.20% at 10 mg mL À1 ) (3S)-6-Hydroxy-8-methoxy-3-methylisochroman (9) Penicillium sp. 19 Cytotoxic (L5178Y: 16.10% at 10 mg mL À1 ) (S)-3,6-Dihydroxy-8-methoxy-3methylisochroman-4-one (10) Aspergillus fumigatus 20 Cytotoxic (MV4-11: 38.39 mM) (R)-3,6-Dihydroxy-8-methox-3methylisochroman-4-one (11) Aspergillus fumigatus 20 8-Methoxy-3-methylisochromane-3,6-diol (12) Aspergillus fumigatus 20 Cytotoxic (MV4-11: 30.00 mM) 3,8-Dimethoxy-3-methylisochroman-6-ol (13) Aspergillus fumigatus 20 3,6,7,8-Tetramethoxy-3-methylisochromane (14) Aspergillus fumigatus 20 Colletobredin A (15) Colletotrichum aotearoa BCRC 09F0161 21 Anti-inammatory (inhibit NO production: 182.2 mM) Colletobredins B-D (16)(17)(18) Colletotrichum aotearoa BCRC 09F0161 21 Monascuspilorin (19) Monascus pilosus BCRC 38072 22 Monascupurpurin (20) Monascus purpureus BCRC 31499 23 Peyronellone A (21) Peyronellaea glomerate 6 Antioxidant (ABTS: 88.8 mM, DPPH: 126.3 mM) Peyronellone B (22) Peyronellaea glomerate 6 Antioxidant (ABTS: 95.2 mM, DPPH: 83.5 mM); hypoxia-protective activity (improved the survival rate of H/R-treated human umbilical vein endothelial cells from 35% to 70% at 5 mM) Penicitol A (23) Penicillium chrysogenum HND11-24 24 Cytotoxic (HeLa: 4.6 mM, BEL-7402: 10.5 mM, HEK-293: 6.7 mM, HCT-116: 5.6 mM, A549: 7.6 mM) Citrifuran A (24) Aspergillus sp. 7 Anti-inammatory (inhibit NO production: 18.3 mM) Citrifuran B (25) Aspergillus sp.…”

Section: Species Activitymentioning

confidence: 99%

“…The plausible biosynthetic pathway for citrifurans A-D (24)(25)(26)(27) was assumed by Yin, et al in 2017. 7 The presumed precursors 332 and 333 were originated from acetate and S-adenosyl methionine.…”

Section: Plausible Biosynthesis Of Citrifurans A-dmentioning

confidence: 99%

“…Aerward, deprotonation of 335 afforded two kinds of enolate anions, 336 and 337, which subsequently heterodimerized with 332 and 334 through a Michael addition reaction to form adducts 338 and 339, respectively. A subsequent intramolecular nucleophilic addition and reduction of 339 constructed a dihydropyran ring in citrifuran A (24), which further went via oxidization to form the epimers, citrifuran B (25) and citrifuran C (26). Similarly, the Scheme 18 Biosynthesis of 6 00 -hydroxy-(R)-mitorubrinic acid, purpurquinone D (À)-mitorubrinic acid, (À)-mitorubrin, and purpurquinone A.…”

Section: Plausible Biosynthesis Of Citrifurans A-dmentioning

confidence: 99%

“…6 Chemical investigation of a mangrove-derived fungus Penicillium chrysogenum HND11-24, led to the characterization of penicitol A (23), a citrinin dimer with a novel tetracyclic skeleton, which was found with cytotoxicity against HeLa, BEL-7402, HEK-293, HCT-116, and A549 cell lines (IC 50 ¼ 4.6-10.5 mM). 24 Citrifurans A-D (24)(25)(26)(27), four uncommon heterodimers of azaphilone and furanone derivatives, were discovered from Aspergillus sp., meanwhile structure of 24 was conrmed by single-crystal X-ray diffraction, among which 24-26 displayed moderate inhibitory on NO production in RAW 264.7 macrophages with IC 50 values of 18.3, 22.6, and 25.3 mM, respectively. 7…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Recent advances in the chemistry and biology of azaphilones

et al. 2020

View full text Add to dashboard Cite

show abstract

Section: Species Activitymentioning

confidence: 99%

Section: Plausible Biosynthesis Of Citrifurans A-dmentioning

confidence: 99%

Section: Plausible Biosynthesis Of Citrifurans A-dmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Recent advances in the chemistry and biology of azaphilones

et al. 2020

View full text Add to dashboard Cite

show abstract

“…lovastatin bioactive compound [122] meleagrin bioactive compound [120,123] methyl 2-(4-hydroxyphenyl) acetate bioactive compound [108] N 4 hydroxystyryl formamides bioactive compound [112] neocyclocitrinols A-D steroid [113] norcyclocitrinol A steroid [113] ochratoxin A mycotoxin [124,125] oxosorbicillinol bioactive compound [114] penicillin G antibiotic [123] penicimonoterpene antifungal compound [110] penicisteroid A, B cytotoxic polyoxygenated steroids [126] Penicillium chrysogenum penicitide A, B cytotoxic and antimicrobial [110] penicitols A and C citrinin analogues [127] penimethavone A flavone [128] penixanacid A xanthone derivative [127] pesudocyclocitrinol A cytotoxic polyoxygenated steroids [113] phenoxyacetic acid antifungal compound [129] phenylacetic acid citrinin analogues [129] PR toxin sesquiterpenoid mycotoxin [130] Database on potential toxigenic capacities of microorganisms used for industrial production…”

Section: Microorganism Secondary Metabolites Commentsmentioning

confidence: 99%

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Benito

Ibáñez

Moncho

et al. 2017

EFSA Supporting Publications

View full text Add to dashboard Cite

The present work constitutes the external scientific report of the EFSA open call OC/EFSA/FEED/2015/01. The aim of the call was to provide EFSA with a database from a review on the taxonomical description and potential toxigenic capacities of microorganisms used for the industrial production of feed additives and food enzymes. The review includes microorganisms used as source of feed additives and food enzymes for which EFSA has received or can potentially receive applications for safety assessment, and which have not been recommended for Qualified Presumption of Safety status. The database also comprises the molecular taxonomical identifiers and biosynthetic pathways involved in the production of toxic compounds and the responsible genes. The main result of the project is shown as a database developed according to the EFSA data structure. The methodological aspects and the queries used in the systematic search, as well as the procedure applied for the screening of scientific documents retrieved are described in this report. Details are available in supplementary appendices.In total, 22970 scientific documents were screened in the literature search, from which 411 were initially selected for providing pertinent data for the scope of the project. From the review of the selected articles, 474 bioactive secondary metabolites were recorded and 59 compounds were further studied in order to obtain data on their toxicology and the conditions in which they are produced by the microorganisms used in industrial fermentations. The database generated in this project comprises details that characterise, when available, the production conditions, genes involved and toxicity of these 59 compounds. This provides information that can be used to establish safety measures when using potentially toxigenic microorganisms in industrial fermentations Disclaimer: The present document has been produced and adopted by the bodies identified above as author(s). This task has been carried out exclusively by the author(s) in the context of a contract between the European Food Safety Authority and the author(s), awarded following a tender procedure. The present document is published complying with the transparency principle to which the Authority is subject. It may not be considered as an output adopted by the Authority. The European Food Safety Authority reserves its rights, view and position as regards the issues addressed and the conclusions reached in the present document, without prejudice to the rights of the authors. Acknowledgements:We thank the following EFSA satff: Jaime Aguilera, Margarita Aguilera-Gómez, Jane Richardson, Mario Monguidi and Davide Gibin for their valuable help and collaboration throughout the project. We also would like to thank the members of AINIA: Sonia Porta, Lidia Tomás, Joaquin Espí and Juan Antonio Nieto for providing expertise in biotechnology and molecular biology and contributing with their efforts to achieve the goals of this project, and Violeta Gómez from the University of Navarra for her colla...

show abstract