Flavipin
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| Category | Antibiotics |
| Catalog number | BBF-00939 |
| CAS | 483-53-4 |
| Molecular Weight | 196.16 |
| Molecular Formula | C9H8O5 |
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Description
Flavipin is an aryl hydrocarbon receptor (AhR) agonist that induces the expression of Ahr downstream genes in mouse CD4+ T cells and CD11b+ macrophages. Flavipin exhibits the DPPH free radical scavenging ability with IC50 value of 7.2 μM, and has potent α-glucosidase inhibition with IC50 value of 33.8 μM.
Specification
| IUPAC Name | 3,4,5-trihydroxy-6-methylphthalaldehyde |
| Canonical SMILES | CC1=C(C(=C(C(=C1O)O)O)C=O)C=O |
| InChI | InChI=1S/C9H8O5/c1-4-5(2-10)6(3-11)8(13)9(14)7(4)12/h2-3,12-14H,1H3 |
| InChI Key | COJARPHAKVBMFD-UHFFFAOYSA-N |
Properties
| Appearance | Light Yellow Crystal |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 233-234°C(dec.) |
| Solubility | Soluble in Water, methanol, acetone, ethyl acetate |
Reference Reading
1. Nematicidal metabolites from endophytic fungus Chaetomium globosum YSC5
Babar Khan, Wei Yan, Shan Wei, Zhiyang Wang, Shuangshuang Zhao, Lingling Cao, Nasir Ahmed Rajput, Yonghao Ye FEMS Microbiol Lett. 2019 Jul 1;366(14):fnz169. doi: 10.1093/femsle/fnz169.
Management of nematodes is a very hectic job due to a highly diverse group of organisms. To find lead compounds for new nematicide development, five metabolites (1-5) were isolated from the culture broth of Chaetomium globosum YSC5 and tested for nematicidal activities against the second stage juveniles (J2s) of Meloidogyne javanica. The results revealed that chaetoglobosin A (1), chaetoglobosin B (2) and flavipin (3) exhibited strong adverse effects (91.6, 83.8 and 87.4%, respectively) on J2 mortality at 200 μg/mL with LC50 values of 88.4, 107.7 and 99.2 μg/mL after 72 h, respectively, while 3-methoxyepicoccone (4) and 4,5,6-trihydroxy-7-methylphthalide (5) showed moderate effects (78.0 and 75.5%, respectively) with LC50 values of 124.0 and 131.6 μg/mL, respectively. Furthermore, in pot assay compounds 1 and 2 appeared to be promising metabolites at 200 μg/mL that significantly reduced nematode reproduction and showed a positive influence on plant growth. Our findings could be helpful for development of new potential bio-based pesticides for integrated management of plant-parasitic nematode.
2. Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079
Harwoko Harwoko, Jungho Lee, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E G Müller, Michael Feldbrügge, Rainer Kalscheuer, Elena Ancheeva, Georgios Daletos, Marian Frank, Zhen Liu, Peter Proksch Fitoterapia. 2020 Oct;146:104698. doi: 10.1016/j.fitote.2020.104698. Epub 2020 Jul 31.
Three new flavipin-derived alkaloids, azacoccones F-H (1-3), along with six known compounds (4-9) were isolated from the endophytic fungus Epicoccum nigrum MK214079 associated with leaves of Salix sp. The structures of the new compounds were established by analysis of their 1D/2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of azacoccones F-H (1-3) was determined by comparison of experimental electronic circular dichroism (ECD) data with reported ones and biogenetic considerations. Epicocconigrone A (4), epipyrone A (5), and epicoccolide B (6) exhibited moderate antibacterial activity against Staphylococcus aureus ATCC 29213 with minimal inhibitory concentration (MIC) values ranging from 25 to 50 μM. Furthermore, epipyrone A (5) and epicoccamide A (7) displayed mild antifungal activity against Ustilago maydis AB33 with MIC values of 1.6 and 1.8 mM, respectively. Epicorazine A (8) showed pronounced cytotoxicity against the L5178Y mouse lymphoma cell line with an IC50 value of 1.3 μM.
3. Anticancer potential of NF-κB targeting apoptotic molecule "flavipin" isolated from endophytic Chaetomium globosum
Venugopal Senthil Kumar, Subramanian Kumaresan, Manoharan Muthu Tamizh, Mohamed Ibrahim Hairul Islam, Krishnaraj Thirugnanasambantham Phytomedicine. 2019 Aug;61:152830. doi: 10.1016/j.phymed.2019.152830. Epub 2019 Jan 17.
Background: Anticancer compounds from natural sources have drawn attention due to their structural diversity and relatively lesser side effects. Endophytic fungi are one such natural resource from, which plethoras of anticancerous compounds have been isolated. Purpose: The objective of the study was to isolate and characterize the bioactive metabolite from Chaetomium globosum that exhibits astonishing antiproliferative activity against cancerous cell lines. Methods: Flavipin was isolated by bioassay-guided fractionation and identified using FT-IR, EI-MS and NMR studies. MTT assay was used to determine the cytotoxicity. Fluorescent staining (AO/EB) and DNA fragmentation studies confirmed the occurrence of apoptosis. Real time PCR and Western blotting were used to analyze the expression of apoptosis related genes and its proteins, respectively. Results: Flavipin inhibited proliferation of A549, HT-29 and MCF-7 cancer cells in dose dependent manner with an IC50 concentration of 9.89 µg/ml, 18 µg/ml and 54 µg/ml, respectively, whereas it was comparatively less sensitive (IC50 = 78.89 µg/ml) against normal cell line (CCD-18Co). At IC50 concentration cancerous cells exhibited cell shrinkage and fragmentation of DNA, which indicated that flavipin induced apoptotic cell death. In treated cells there is an up-regulation of p53 gene and its associated protein, whereas reciprocal expression was observed in BCL-2 gene and its protein. Furthermore, western blotting results also showed down-regulation of NFκB. Conclusion: This is the first report on the antiproliferative activity of flavipin isolated from endophytic C. globosum and also proposed that interaction of flavipin with NFкB could be a possible mechanism for this activity. Flavipin induced apoptosis at low concentrations in cancer cell lines (A549, HT-29) and exhibited itself as a potential anticancer agent.
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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 ╳
