Flavoglaucin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04436 |
| CAS | 523-73-9 |
| Molecular Weight | 304.42 |
| Molecular Formula | C19H28O3 |
| Purity | 98.0% |
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Description
Flavoglaucin is a natural compound isolated from marine fungus Eurotium sp. SF-5989. Flavoglaucin exhibits significant inhibitory effect on PTP1B with IC50 value of 13.4 micrometer. Flavoglaucin shows good binding affinity for human opioid or cannabinoid receptors. Flavoglaucin has anti-inflammatory effect, which inhibits inflammatory mediators via the induction of heme oxygenase-1 in lipopolysaccharide-stimulated RAW264.7 macrophages. Flavoglaucin exhibits significant radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) with the IC50 value of 11.3 microM.
Specification
| Synonyms | 6-Heptyl-3-(3-methyl-2-butenyl)gentisaldehyde; Benzaldehyde, 2-heptyl-3,6-dihydroxy-5-(3-methyl-2-butenyl)- |
| IUPAC Name | 2-heptyl-3,6-dihydroxy-5-(3-methylbut-2-enyl)benzaldehyde |
| Canonical SMILES | CCCCCCCC1=C(C=C(C(=C1C=O)O)CC=C(C)C)O |
| InChI | InChI=1S/C19H28O3/c1-4-5-6-7-8-9-16-17(13-20)19(22)15(12-18(16)21)11-10-14(2)3/h10,12-13,21-22H,4-9,11H2,1-3H3 |
| InChI Key | RGRXZGKXEJHPQQ-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Powder |
| Boiling Point | 433.7±45.0°C (Predicted) |
| Melting Point | 105.5-109.0°C |
| Density | 1.053±0.06 g/cm3 (Predicted) |
Reference Reading
1. Characterization of Hypolipidemic Phenol Analogues from Fermented Tea by Eurotium cristatum
Fuhang Song, Wei Dai, Honghua Li, Xinwan Zhang, Xiuli Xu, Linlin Ma, Long Wang Foods. 2022 Dec 22;12(1):49. doi: 10.3390/foods12010049.
Fuzhuan brick tea (FBT), a type of black tea, is a traditional beverage in China, especially popular among frontier ethnic groups. FBT is well-known for its health benefits, such as hypoglycemic, anti-hypertensive, anti-inflammatory, diuretic, and detoxification effects. Nevertheless, the underlying mechanisms on the molecular level are still elusive and the key compounds responsible for the health benefits are unidentified. Previous studies have mainly focused on functional studies of the water extract. However, FBT is typically cooked with butter or milk. Therefore, we hypothesized that some lipophilic components in FBT, which can be absorbed through the co-consumption of butter or milk, may play an important role in the health benefits. The present study aimed to investigate whether the liposoluble extract of FBT alleviates symptoms related to metabolic diseases and to identify the active compounds involved. By comparing the high-performance liquid chromatography (HPLC) profiles of water, milk and hexane extract, some low polarity peaks were observed in the milk and hexane extracts. Furthermore, the hexane extract treatment alleviated body weight gain, serum total cholesterol and triglyceride levels, and inhibited the accumulation of hepatic fat granules in a high-fat diet (HFD)-induced C57BL/6N mouse model. In order to identify the key functional lipophilic compounds in FBT, the hexane extract of FBT was subjected to chemical characterization. Four phenol analogs were characterized, namely, isodihydroauroglaucin (1), dihydroauroglaucin (2), tetrahydroauroglaucin (3), and flavoglaucin (4). Compounds 1 and 4 reduced the levels of total cholesterol and triglyceride in vivo. Both compounds also inhibited the high-fat diet-induced body weight gain and accumulation of fat granules in the liver of C57BL/6N mice. Isodihydroauroglaucin and flavoglaucin have therefore been identified as bioactive ingredients that contribute to the health benefits of FBT.
2. A novel alkaloid from Portulaca oleracea L. and its anti-inflammatory activity
Yingying Gu, Aijing Leng, Wenjie Zhang, Xixiang Ying, Didier Stien Nat Prod Res. 2022 Jan;36(2):595-600. doi: 10.1080/14786419.2020.1795855. Epub 2020 Jul 21.
A novel alkaloid identified as methyl 8,9-dihydroxy-11-oxo-6,11-dihydro-5H-benzo[d]pyrrolo[1,2-a]azepine-3-carboxylate, named portulacatone A (1) with six known compounds Oleracein E (2), 6,7-dihdroxy-3,4-dihydro-2H-isoquinolin-1-one (3), N-trans-p-coumaroytyramine (4), 9H-carbazole (5), isoaspergin (6) and flavoglaucin (7) were obtained from Portulaca oleracea L., while compounds (5-7) were isolated from the plant for the first time. The new structure was identified by using UHPLC-ESI-Q-TOF/MS, 1D, 2D NMR and the others were proved by 1H-NMR and 13C NMR that comparing with previous reports. It was suggested that the portulacatone A (1) can significantly inhibit the inflammatory factor, interleukin-1β (IL-1β) in the RAW 264.7 cells induced by LPS.
3. 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.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
