Exophillic acid
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00893 |
| CAS | |
| Molecular Weight | 704.84 |
| Molecular Formula | C38H56O12 |
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Description
Exophillic acid is a substance produced by Exophiala pisciphila that inhibits human immunodeficiency virus-1 (HIV-1) integrase activity.
Specification
| Synonyms | 2-hydroxy-4-[4-hydroxy-2-nonyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-benzoyl]oxy-6-nonyl-benzoic acid; Benzoic acid, 2-(beta-D-glucopyranosyloxy)-4-hydroxy-6-nonyl-, 4-carboxy-3-hydroxy-5-nonylphenyl ester |
| IUPAC Name | 2-hydroxy-4-[4-hydroxy-2-nonyl-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoyl]oxy-6-nonylbenzoic acid |
| Canonical SMILES | CCCCCCCCCC1=C(C(=CC(=C1)O)OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC3=CC(=C(C(=C3)O)C(=O)O)CCCCCCCCC |
| InChI | InChI=1S/C38H56O12/c1-3-5-7-9-11-13-15-17-24-19-26(40)21-29(49-38-35(44)34(43)33(42)30(23-39)50-38)32(24)37(47)48-27-20-25(31(36(45)46)28(41)22-27)18-16-14-12-10-8-6-4-2/h19-22,30,33-35,38-44H,3-18,23H2,1-2H3,(H,45,46)/t30-,33-,34+,35-,38-/m1/s1 |
| InChI Key | GBXMNTLQBMLGFM-IHQQTPIISA-N |
Reference Reading
1. Diversity of exophillic acid derivatives in strains of an endophytic Exophiala sp
Zakaria Cheikh-Ali, Kyriaki Glynou, Tahir Ali, Sebastian Ploch, Marcel Kaiser, Marco Thines, Helge B Bode, Jose G Maciá-Vicente Phytochemistry. 2015 Oct;118:83-93. doi: 10.1016/j.phytochem.2015.08.006. Epub 2015 Aug 19.
Members of the fungal genus Exophiala are common saprobes in soil and water environments, opportunistic pathogens of animals, or endophytes in plant roots. Their ecological versatility could imply a capacity to produce diverse secondary metabolites, but only a few studies have aimed at characterizing their chemical profiles. Here, we assessed the secondary metabolites produced by five Exophiala sp. strains of a particular phylotype, isolated from roots of Microthlaspi perfoliatum growing in different European localities. Exophillic acid and two previously undescribed compounds were isolated from these strains, and their structures were elucidated by spectroscopic methods using MS, 1D and 2D NMR. Bioassays revealed a weak activity of these compounds against disease-causing protozoa and mammalian cells. In addition, 18 related structures were identified by UPLC/MS based on comparisons with the isolated structures. Three Exophiala strains produced derivatives containing a β-d-glucopyranoside moiety, and their colony morphology was distinct from the other two strains, which produced derivatives lacking β-d-glucopyranoside. Whether the chemical/morphological strain types represent variants of the same genotype or independent genetic populations within Exophiala remains to be evaluated.
2. Fungal Secondary Metabolite Exophillic Acid Selectively Inhibits the Entry of Hepatitis B and D Viruses
Chisa Kobayashi, Yoshihiro Watanabe, Mizuki Oshima, Tomoyasu Hirose, Masako Yamasaki, Masashi Iwamoto, Masato Iwatsuki, Yukihiro Asami, Kouji Kuramochi, Kousho Wakae, Hideki Aizaki, Masamichi Muramatsu, Camille Sureau, Toshiaki Sunazuka, Koichi Watashi Viruses. 2022 Apr 6;14(4):764. doi: 10.3390/v14040764.
Current anti-hepatitis B virus (HBV) drugs are suppressive but not curative for HBV infection, so there is considerable demand for the development of new anti-HBV agents. In this study, we found that fungus-derived exophillic acid inhibits HBV infection with a 50% maximal inhibitory concentration (IC50) of 1.1 µM and a 50% cytotoxic concentration (CC50) of >30 µM in primary human hepatocytes. Exophillic acid inhibited preS1-mediated viral attachment to cells but did not affect intracellular HBV replication. Exophillic acid appears to target the host cells to reduce their susceptibility to viral attachment rather than acting on the viral particles. We found that exophillic acid interacted with the HBV receptor, sodium taurocholate cotransporting polypeptide (NTCP). Exophillic acid impaired the uptake of bile acid, the original function of NTCP. Consistent with our hypothesis that it affects NTCP, exophillic acid inhibited infection with HBV and hepatitis D virus (HDV), but not that of hepatitis C virus. Moreover, exophillic acid showed a pan-genotypic anti-HBV effect. We thus identified the anti-HBV/HDV activity of exophillic acid and revealed its mode of action. Exophillic acid is expected to be a potential new lead compound for the development of antiviral agents.
3. Identification of natural inhibitors of Entamoeba histolytica cysteine synthase from microbial secondary metabolites
Mihoko Mori, Ghulam Jeelani, Yui Masuda, Kazunari Sakai, Kumiko Tsukui, Danang Waluyo, Tarwadi, Yoshio Watanabe, Kenichi Nonaka, Atsuko Matsumoto, Satoshi Ōmura, Tomoyoshi Nozaki, Kazuro Shiomi Front Microbiol. 2015 Sep 14;6:962. doi: 10.3389/fmicb.2015.00962. eCollection 2015.
Amebiasis is a common worldwide diarrheal disease, caused by the protozoan parasite, Entamoeba histolytica. Metronidazole has been a drug of choice against amebiasis for decades despite its known side effects and low efficacy against asymptomatic cyst carriers. E. histolytica is also capable of surviving sub-therapeutic levels of metronidazole in vitro. Novel drugs with different mode of action are therefore urgently needed. The sulfur assimilatory de novo L-cysteine biosynthetic pathway is essential for various cellular activities, including the proliferation and anti-oxidative defense of E. histolytica. Since the pathway, consisting of two reactions catalyzed by serine acetyltransferase (SAT) and cysteine synthase (CS, O-acetylserine sulfhydrylase), does not exist in humans, it is a rational drug target against amebiasis. To discover inhibitors against the CS of E. histolytica (EhCS), the compounds of Kitasato Natural Products Library were screened against two recombinant CS isozymes: EhCS1 and EhCS3. Nine compounds inhibited EhCS1 and EhCS3 with IC50 values of 0.31-490 μM. Of those, seven compounds share a naphthoquinone moiety, indicating the structural importance of the moiety for binding to the active site of EhCS1 and EhCS3. We further screened >9,000 microbial broths for CS inhibition and purified two compounds, xanthofulvin and exophillic acid from fungal broths. Xanthofulvin inhibited EhCS1 and EhCS3. Exophillic acid showed high selectivity against EhCS1, but exhibited no inhibition against EhCS3. In vitro anti-amebic activity of the 11 EhCS inhibitors was also examined. Deacetylkinamycin C and nanaomycin A showed more potent amebicidal activity with IC50 values of 18 and 0.8 μM, respectively, in the cysteine deprived conditions. The differential sensitivity of trophozoites against deacetylkinamycin C in the presence or absence of L-cysteine in the medium and the IC50 values against EhCS suggest the amebicidal effect of deacetylkinamycin C is due to CS inhibition.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
