Emestrin B
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| Category | Others |
| Catalog number | BBF-01216 |
| CAS | 107395-35-7 |
| Molecular Weight | 630.67 |
| Molecular Formula | C27H22N2O10S3 |
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Description
It is produced by the strain of Emericella striata.
Specification
| IUPAC Name | (1R,3S,9S,23S,24R,33R)-19,23,33-trihydroxy-15-methoxy-29-methyl-6,10,17-trioxa-25,26,27-trithia-2,29-diazaheptacyclo[22.3.2.11,4.12,24.112,16.118,22.03,9]tritriaconta-4,7,12(32),13,15,18,20,22(31)-octaene-11,28,30-trione |
| Canonical SMILES | CN1C(=O)C23C(C4=COC=CC5C4N2C(=O)C1(C(C6=CC(=C(C=C6)O)OC7=C(C=CC(=C7)C(=O)O5)OC)O)SSS3)O |
| InChI | InChI=1S/C27H22N2O10S3/c1-28-24(34)27-22(32)14-11-37-8-7-17-20(14)29(27)25(35)26(28,40-42-41-27)21(31)12-3-5-15(30)18(9-12)38-19-10-13(23(33)39-17)4-6-16(19)36-2/h3-11,17,20-22,30-32H,1-2H3/t17-,20-,21-,22+,26+,27+/m0/s1 |
| InChI Key | OANRUBPIIYIANQ-YITDFDIYSA-N |
Properties
| Appearance | Crystalline Powder |
| Melting Point | 230-238 °C (dec.) |
| Solubility | Soluble in Benzene, Methanol, Acetone |
Reference Reading
1. Towards the Synthesis of Dihydrooxepino[4,3-b]pyrrole-Containing Natural Products via Cope Rearrangement of Vinyl Pyrrole Epoxides
Alex Cameron, Brendan Fisher, Nicholas Fisk, Jessica Hummel, Jonathan M White, Elizabeth H Krenske, Mark A Rizzacasa Org Lett. 2015 Dec 18;17(24):5998-6001. doi: 10.1021/acs.orglett.5b02965. Epub 2015 Dec 2.
An approach to the dihydrooxepino[4,3-b]pyrrole core of diketopiperazine natural products which utilizes a vinyl pyrrole epoxide Cope rearrangement was investigated. It was found that an ester substituent on the epoxide was essential for the [3,3]-rearrangement to occur. Density functional calculations with M06-2X provided explanations for the effects of the pyrrole and ester groups on these rearrangements.
2. Asperemestrins A-D, Emestrin Hybrid Polymers with Bridged Skeletons from the Endophytic Fungus Aspergillus nidulans
Qin Li, Aimin Fu, Mengsha Wei, Yang Xiao, Jie Yin, Jianzheng Huang, Xiao-Nian Li, Qingyi Tong, Chunmei Chen, Hucheng Zhu, Yonghui Zhang Org Lett. 2022 Sep 23;24(37):6800-6804. doi: 10.1021/acs.orglett.2c02701. Epub 2022 Sep 8.
Four emestrin hybrid polymers, asperemestrins A-D (1-4, respectively), were isolated from the fungus Aspergillus nidulans. Asperemestrins A-C are the first examples of emestrin-sterigmatocystin heterodimers bearing a 7/5/6/6/5/5/6/6/6 nonacyclic system with a 2,5-diazabicyclo[2.2.2]octane-3,6-dione core, while asperemestrin D features an unprecedented 2,15-dithia-17,19-diazabicyclo[14.2.2]icosa-4,8-diene-12,18,20-trione core skeleton. Their structures were determined by extensive spectroscopic data, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Asperemestrin B showed moderate cytotoxicity against cancer cell lines, including SU-DHL-2, HEPG2, and HL-60.
3. Aspergillus section Nidulantes (formerly Emericella): Polyphasic taxonomy, chemistry and biology
A J Chen, J C Frisvad, B D Sun, J Varga, S Kocsubé, J Dijksterhuis, D H Kim, S-B Hong, J Houbraken, R A Samson Stud Mycol. 2016 Jun;84:1-118. doi: 10.1016/j.simyco.2016.10.001. Epub 2016 Oct 19.
Aspergillus section Nidulantes includes species with striking morphological characters, such as biseriate conidiophores with brown-pigmented stipes, and if present, the production of ascomata embedded in masses of Hülle cells with often reddish brown ascospores. The majority of species in this section have a sexual state, which were named Emericella in the dual name nomenclature system. In the present study, strains belonging to subgenus Nidulantes were subjected to multilocus molecular phylogenetic analyses using internal transcribed spacer region (ITS), partial β-tubulin (BenA), calmodulin (CaM) and RNA polymerase II second largest subunit (RPB2) sequences. Nine sections are accepted in subgenus Nidulantes including the new section Cavernicolus. A polyphasic approach using morphological characters, extrolites, physiological characters and phylogeny was applied to investigate the taxonomy of section Nidulantes. Based on this approach, section Nidulantes is subdivided in seven clades and 65 species, and 10 species are described here as new. Morphological characters including colour, shape, size, and ornamentation of ascospores, shape and size of conidia and vesicles, growth temperatures are important for identifying species. Many species of section Nidulantes produce the carcinogenic mycotoxin sterigmatocystin. The most important mycotoxins in Aspergillus section Nidulantes are aflatoxins, sterigmatocystin, emestrin, fumitremorgins, asteltoxins, and paxillin while other extrolites are useful drugs or drug lead candidates such as echinocandins, mulundocandins, calbistrins, varitriols, variecolins and terrain. Aflatoxin B1 is produced by four species: A. astellatus, A. miraensis, A. olivicola, and A. venezuelensis. Keywords: A. aurantiopurpureus A.J. Chen; A. botswanensis A.J. Chen; A. dromiae A.J. Chen; A. israelensis A.J. Chen; A. latilabiatus A.J. Chen; A. savannensis A.J. Chen; A. stercorarius A.J. Chen; A. sulphureoviridis A.J. Chen; A. viridicatenatus A.J. Chen; Ascomycetes; Aspergillus angustatus A.J. Chen; Eurotiales; Frisvad & Samson; Multi-gene phylogeny; Section Cavernicolus A.J. Chen, Frisvad & Samson; Sterigmatocystin.
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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 ╳
