Asperfuran
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| Category | Antibiotics |
| Catalog number | BBF-00565 |
| CAS | 129277-10-7 |
| Molecular Weight | 218.25 |
| Molecular Formula | C13H14O3 |
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Description
Asperfuran is an antifungal antibiotic produced by Asperfuran oryzae. Asperfuran has fungal activity and can inhibit fungal chitin synthase, but the effect can be completely offset by lecithin. It also has inhibitory effect on HeLa S3 cells and L1210 cells.
Specification
| Synonyms | Asperfuran; 5,7-Benzofurandiol, 2,3-dihydro-2-(1,3-pentadienyl)-, (R-(E,E))- |
| IUPAC Name | (2R)-2-[(1E,3E)-penta-1,3-dienyl]-2,3-dihydro-1-benzofuran-5,7-diol |
| Canonical SMILES | CC=CC=CC1CC2=C(O1)C(=CC(=C2)O)O |
| InChI | InChI=1S/C13H14O3/c1-2-3-4-5-11-7-9-6-10(14)8-12(15)13(9)16-11/h2-6,8,11,14-15H,7H2,1H3/b3-2+,5-4+/t11-/m0/s1 |
| InChI Key | WTFIFQXTQCYJKU-JWVODRKRSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 380.7°C at 760 mmHg |
| Melting Point | 130°C |
| Density | 1.254 g/cm3 |
Reference Reading
1. Four psychrotolerant species with high chemical diversity consistently producing cycloaspeptide A, Penicillium jamesonlandense sp. nov., Penicillium ribium sp. nov., Penicillium soppii and Penicillium lanosum
Jens C Frisvad, Thomas O Larsen, Petur W Dalsgaard, Keith A Seifert, Gerry Louis-Seize, E K Lyhne, Bruce B Jarvis, James C Fettinger, David P Overy Int J Syst Evol Microbiol. 2006 Jun;56(Pt 6):1427-1437. doi: 10.1099/ijs.0.64160-0.
Penicillium jamesonlandense is a novel species from Greenland that grows exceptionally slowly at 25 degrees C and has an optimum temperature for growth of 17-18 degrees C. The novel species is more psychrotolerant than any other Penicillium species described to date. Isolates of this novel species produce a range of secondary metabolites with a high chemical diversity, represented by kojic acid, penicillic acid, griseofulvin, pseurotin, chrysogine, tryptoquivalins and cycloaspeptide. Penicillium ribium, another novel psychrotolerant species from the Rocky Mountains, Wyoming, USA, produces asperfuran, kojic acid and cycloaspeptide. Originally reported from an unidentified Aspergillus species isolated from Nepal, cycloaspeptide A is reported here for the first time from the two novel Penicillium species and two known psychrotolerant species with high chemical diversity, Penicillium soppii and Penicillium lanosum. All species, except P. ribium, produce a combination of cycloaspeptide and griseofulvin. However, P. ribium (3/5 strains) produced the precursor to griseofulvin, norlichexanthone. The type strain of Penicillium jamesonlandense sp. nov. is DAOM 234087(T) (=IBT 21984(T) = IBT 24411(T) = CBS 102888(T)) and the type strain of Penicillium ribium sp. nov. is DAOM 234091(T) (=IBT 16537(T) = IBT 24431(T)).
2. Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica
Soleiman E Helaly, Wilawan Kuephadungphan, Patima Phainuphong, Mahmoud A A Ibrahim, Kanoksri Tasanathai, Suchada Mongkolsamrit, Janet Jennifer Luangsa-Ard, Souwalak Phongpaichit, Vatcharin Rukachaisirikul, Marc Stadler Beilstein J Org Chem. 2019 Dec 16;15:2968-2981. doi: 10.3762/bjoc.15.293. eCollection 2019.
In the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone) derivative, pigmentosin B (2), were isolated from the spider-associated fungus Gibellula sp. Furthermore, a new glycosylated asperfuran 3, together with one new (6) and two known (4 and 5) cyclodepsipeptides, was isolated from Cordyceps javanica. The pigmentosins 1 and 2 showed to be active against biofilm formation of Staphylococcus aureus DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (2), as well as the antimicrobial effect of pigmentosin A (1), made them good candidates for further development for use in combination therapy of infections involving biofilm-forming S. aureus. The structure elucidation and determination of the absolute configuration were accomplished using a combination of spectroscopy, including 1D and 2D NMR, HRMS, Mosher ester analysis, and comparison of calculated/experimental ECD spectra. A chemotaxonomic investigation of the secondary metabolite profiles using analytical HPLC coupled with diode array detection and mass spectrometry (HPLC-DAD-MS) revealed that the production of pigmentosin B (2) was apparently specific for Gibellula sp., while the glycoasperfuran 3 was specific for C. javanica.
3. New bioactive secondary metabolites from the Anoectochilus roxburghii endophytic fungus Aspergillus versicolor
Mengyi Deng, Yaping Liu, Yingying Huang, Xu Yin, Yuan Zhou, Yulin Duan, Shuangshuang Xie, Yi Guo, Yuben Qiao, Zhengyi Shi, Li Tao, Yunfang Cao, Changxing Qi, Yonghui Zhang Fitoterapia. 2020 Jun;143:104532. doi: 10.1016/j.fitote.2020.104532. Epub 2020 Mar 7.
Six new compounds, including two new isochromane lactones, versicoisochromanes A and B (1 and 2), two new benzolactones, versicobenzos A and B (3 and 4), one furancarboxylic derivate, asperfuran A (6) and one ergosterol-type steroid, asperergoster A (7), along with five known steroids (8-12), were isolated from the Anoectochilus roxburghii endophytic fungus Aspergillus versicolor. The structures of these new compounds were determined by extensive spectroscopic techniques and electronic circular dichroism (ECD) calculations. It is notable that the new compound 7 exhibited obvious IL-1β, NO and TNF-α inhibitory activity in LPS-stimulated RAW264.7 macrophages, with IC50 values of 35.5, 33.9 and 31.3 μM, respectively. Furthermore, compounds 7 and 8 displayed potential inhibitory effects on murine splenocytes proliferation stimulated by anti-CD3/anti-CD28 monoclonal antibodies (mAbs), meanwhile suppress the lipopolysaccharide (LPS) irritated murine splenocytes proliferation.
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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 ╳
