Auroglaucin

Auroglaucin

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Auroglaucin
Category Others
Catalog number BBF-05384
CAS 41451-81-4
Molecular Weight 298.38
Molecular Formula C19H22O3

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Description

It is produced by the strain of Aspergillus spp.

Specification

Synonyms 2-[(1E,3E,5E)-1,3,5-Heptatrienyl]-3,6-dihydroxy-5-(3-methyl-2-butenyl)benzaldehyde; Auroglaucine; 2-((1E,3E,5E)-hepta-1,3,5-trien-1-yl)-3,6-dihydroxy-5-(3-methylbut-2-en-1-yl)benzaldehyde
IUPAC Name 2-[(1E,3E,5E)-hepta-1,3,5-trienyl]-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde
Canonical SMILES CC=CC=CC=CC1=C(C=C(C(=C1C=O)O)CC=C(C)C)O
InChI InChI=1S/C19H22O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h4-10,12-13,21-22H,11H2,1-3H3/b5-4+,7-6+,9-8+
InChI Key ZKBCBIRBLMTSPC-ZAJAATJQSA-N

Properties

Appearance Orange-red Powder
Boiling Point 477.1°C at 760 mmHg
Melting Point 153°C
Density 1.113 g/cm3

Reference Reading

1. Genome Mining and Analysis of PKS Genes in Eurotium cristatum E1 Isolated from Fuzhuan Brick Tea
Xiaoxiao Guo, Fusheng Chen, Jiao Liu, Yanchun Shao, Xiaohong Wang, Youxiang Zhou J Fungi (Basel). 2022 Feb 16;8(2):193. doi: 10.3390/jof8020193.
Eurotium cristatum as the dominant fungi species of Fuzhuan brick tea in China, can produce multitudinous secondary metabolites (SMs) with various bioactivities. Polyketides are a very important class of SMs found in E. cristatum and have gained extensive attention in recent years due to their remarkable diversity of structures and multiple functions. Therefore, it is necessary to explore the polyketides produced by E. cristatum at the genomic level to enhance its application value. In this paper, 12 polyketide synthase (PKS) genes were found in the whole genome of E. cristatum E1 isolated from Fuzhuan brick tea. In addition, the qRT-PCR results further demonstrated that these genes were expressed. Moreover, metabolic analysis demonstrated E. cristatum E1 can produce a variety of polyketides, including citreorosein, emodin, physcion, isoaspergin, dihydroauroglaucin, iso-dihydroauroglaucin, aspergin, flavoglaucin and auroglaucin. Furthermore, based on genomic analysis, the putative secondary metabolites clusters for emodin and flavoglaucin were proposed. The results reported here will lay a good basis for systematically mining SMs resources of E. cristatum and broadening its application fields.
2. Bioactive Metabolites From Acid-Tolerant Fungi in a Thai Mangrove Sediment
Hai Gao, Yanan Wang, Qiao Luo, Liyuan Yang, Xingxing He, Jun Wu, Konthorn Kachanuban, Pongthep Wilaipun, Weiming Zhu, Yi Wang Front Microbiol. 2021 Jan 22;11:609952. doi: 10.3389/fmicb.2020.609952. eCollection 2020.
Despite being potentially useful extremophile resources, there have been few reports on acid-tolerant fungi and their bioactive metabolites. Acidophilic/aciduric fungi (n = 237) were isolated from Thai mangrove sediments in an acidic medium. Using fungal identification technology (including morphologic observation, chemical screening, and sequence comparisons) all the isolates were identified and 41 representative isolates were selected for analysis of the phylogenetic relationships (ITS rDNA, β-tubulin, calmodulin, and actin gene sequences). There were seven genera identified - Penicillium; Aspergillus; Talaromyces; Cladosporium; Allophoma; Alternaria; and Trichoderma - in four taxonomic orders of the phylum Ascomycota, and Penicillium, Aspergillus, and Talaromyces were the dominant genera. Acidity tolerance was evaluated and 95% of the isolates could grow under extremely acidic conditions (pH 2). Six strains were classed as acidophilic fungi that cannot survive under pH 7, all of which had an extraordinarily close genetic relationship and belonged to the genus Talaromyces. This is the first report on the acidophilic characteristics of this genus. The antimicrobial, anti-tumor, and antiviral activities of the fermentation extracts were evaluated. Nearly three-quarters of the extracts showed cytotoxic activity, while less than a quarter showed antimicrobial or anti-H1N1 activity. The typical aciduric fungus Penicillium oxalicum OUCMDZ-5207 showed similar growth but completely different chemical diversity at pH 3 and 7. The metabolites of OUCMDZ-5207 that were obtained only at pH 3 were identified as tetrahydroauroglaucin (1), flavoglaucin (2), and auroglaucin (3), among which auroglaucin showed strong selective inhibition of A549 cells with an IC50 value of 5.67 μM. These results suggest that acid stress can activate silent gene clusters to expand the diversity of secondary metabolites, and the bioprospecting of aciduric/acidophilic microorganism resources in Thai mangrove sediments may lead to the discovery of compounds with potential medicinal applications.
3. Metabolite Profiling and Anti-Aging Activity of Rice Koji Fermented with Aspergillus oryzae and Aspergillus cristatus: A Comparative Study
Hyunji Lee, Sunmin Lee, Seoyeon Kyung, Jeoungjin Ryu, Seunghyun Kang, Myeongsam Park, Choonghwan Lee Metabolites. 2021 Aug 8;11(8):524. doi: 10.3390/metabo11080524.
Rice koji, used as a starter for maximizing fermentation benefits, produces versatile end products depending on the inoculum microbes used. Here, we performed metabolite profiling to compare rice koji fermented with two important filamentous fungus, Aspergillus oryzae and A. cristatus, during 8 days. The multivariate analyses showed distinct patterns of primary and secondary metabolites in the two kojis. The rice koji fermented with A. oryzae (RAO) showed increased α-glucosidase activity and higher contents of sugar derivatives than the one fermented with A. cristatus (RAC). RAC showed enhanced β-glucosidase activity and increased contents of flavonoids and lysophospholipids, compared to RAO. Overall, at the final fermentation stage (8 days), the antioxidant activities and anti-aging effects were higher in RAC than in RAO, corresponding to the increased metabolites such as flavonoids and auroglaucin derivatives in RAC. This comparative metabolomic approach can be applied in production optimization and quality control analyses of koji products.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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