Cycloechinulin
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| Category | Bioactive by-products |
| Catalog number | BBF-04580 |
| CAS | 143086-29-7 |
| Molecular Weight | 351.40 |
| Molecular Formula | C20H21N3O3 |
| Purity | >99% by HPLC |
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Description
An unusual diketopiperazine isolated from aspergillus ochraceus. It exhibits insecticidal activity against the lepidopteran crop pest, helicoverpa zea. It is used as a secondary metabolite standard for polyphasic taxonomy in aspergillus.
Specification
| Synonyms | (3S)-2,3,8,9-Tetrahydro-11-methoxy-3,8,8-trimethylpyrazino[1',2':1,2]azocino[5,4-b]indole-1,4-dione; (S)-2,3,8,9-Tetrahydro-11-methoxy-3,8,8-trimethyl-pyrazino[1',2':1,2]azocino[5,4-b]indole-1,4-dione |
| Storage | Store at -20°C |
| IUPAC Name | (2Z,6S,9Z)-16-methoxy-6,11,11-trimethyl-5,8,13-triazatetracyclo[10.7.0.03,8.014,19]nonadeca-1(12),2,9,14(19),15,17-hexaene-4,7-dione |
| Canonical SMILES | CC1C(=O)N2C=CC(C3=C(C=C2C(=O)N1)C4=C(N3)C=C(C=C4)OC)(C)C |
| InChI | InChI=1S/C20H21N3O3/c1-11-19(25)23-8-7-20(2,3)17-14(10-16(23)18(24)21-11)13-6-5-12(26-4)9-15(13)22-17/h5-11,22H,1-4H3,(H,21,24)/b8-7-,16-10-/t11-/m0/s1 |
| InChI Key | RCTQPWJZZZLMBI-RPHUSYQJSA-N |
| Source | Aspergillus ochraceus |
Properties
| Appearance | Light Tan Solid |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 675.0±0.0°C at 760 mmHg |
| Density | 1.3±0.0 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp
Hee Jae Shin, Byeoung-Kyu Choi, Jihoon Lee, Hwa-Sun Lee, Hyi-Seung Lee, Jong Seok Lee, Jong Soon Kang, Tran Thi Thanh Van, Yeon-Ju Lee, Phan Thi Hoai Trinh Mar Drugs . 2018 Jan 5;16(1):14. doi: 10.3390/md16010014.
A new α-pyrone merosesquiterpenoid possessing an angular tetracyclic carbon skeleton, ochraceopone F (1), and four known secondary metabolites, aspertetranone D (2), cycloechinulin (3), wasabidienone E (4), and mactanamide (5), were isolated from the marine fungusAspergillus flocculosusderived from a spongeStylissasp. collected in Vietnam. The structures of Compounds1-5were elucidated by analysis of 1D and 2D NMR spectra and MS data. All the isolated compounds were evaluated for anti-proliferation activity and their suppression effects on receptor activator of nuclear factor κB ligand (RANKL)-induced osteoclast differentiation using tartate-resisant acid phosphatase (TRAP). Compounds1-5had no anti-proliferative effect on human cancer cell lines up to 30 μg/mL. Among these compounds, aspertetranone D (2) and wasabidienone E (4) exhibited weak osteoclast differentiation inhibitory activity at 10 μg/mL. However, mactanamide (5) showed a potent suppression effect of osteoclast differentiation without any evidence of cytotoxicity.
2. Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus
Hee Jae Shin, Byeoung-Kyu Choi, Duy Quang Dao, Thi Le Anh Nguyen, Jong Seok Lee, Thi Thu Trang Phan, Thi Thanh Van Tran, Phan Thi Hoai Trinh J Chem Inf Model . 2020 Mar 23;60(3):1329-1351. doi: 10.1021/acs.jcim.9b00964.
This computational and experimental work aims to elucidate physicochemical and photophysical natures of free radical scavenging and ultraviolet radiation (UVR) filtering activities of five terpenoids available in the extract of marine fungus. The antioxidant activities of ochraceopone F (C1), aspertetranone D (C2), cycloechinulin (C3), wasabidienone E (C4), and mactanamide (C5) are evaluated by using density functional theory (DFT) at the M05-2X/6-311++G(d,p) level of theory in the gas phase, water, and pentyl ethanoate (PEA). Double antioxidant mechanisms allowing the second (H+/e-) donation such as double hydrogen atom transfer (dHAT), double single electron transfer-proton transfer (dSET-PT), and double sequential proton loss-electron transfer (dSPL-ET) are considered. Reaction enthalpies (ΔrH0), standard Gibbs free energies (ΔrG0) and potential energy surfaces of reactions toward HOO·radical are then established to evaluate the hydrogen transfer (HT) and radical adduct formation (RAF) mechanisms. The computational results are supported by DPPH·and ABTS·+antioxidant essays. Results show that all compoundsC1-C5are able to scavenge two free radicals via dHAT, dSET-PT, and dSPL-ET mechanisms. Among the compounds,C3andC4represent the most potential antioxidants, especially via HAT and RAF mechanisms in all the reaction media. Their rate constants for both HAT and RAF reactions are remarkably higher than that of Trolox and ascorbic acid. The kinetic calculations on activation Gibbs free energies (ΔG⧧) and rate constants (kTST) based on conventional transition state theory (TST) reveal that HAT and RAF processes are in competition in solvents. Photophysical processes occurring during UVR exposure are investigated using the time dependent density functional theory (TD-DFT) combined with UV-vis experiments. The obtained results highlight the promising activities ofC1-C5in UVR absorption in the ranges of UVA and UVB. Among them,C3andC4also show better UV absorption properties with the easiest excitations (band gaps equal to 4.06 and 3.65 eV). This study suggests the natural candidates possibly used in organic sunscreen.
3. Linking secondary metabolites to gene clusters through genome sequencing of six diverse Aspergillus species
Chew Yee Ngan, Uffe H Mortensen, Inge Kjærbølling, Alicia Clum, Alan Kuo, Blake A Simmons, Martin E Kogle, Igor V Grigoriev, Jane L Nybo, Anna Lipzen, Sajeet Haridas, Thomas O Larsen, Jon K Magnuson, Paul Bowyer, Kurt LaButti, Mikael R Andersen, Ellen K Lyhne, Scott E Baker, Kerrie Barry, Jennifer Chiniquy, Sebastian Theobald, Yudai Matsuda, Stephen Mondo, Chris Daum, Tammi C Vesth, Jens C Frisvad, Asaf Salamov Proc Natl Acad Sci U S A . 2018 Jan 23;115(4):E753-E761. doi: 10.1073/pnas.1715954115.
The fungal genus ofAspergillusis highly interesting, containing everything from industrial cell factories, model organisms, and human pathogens. In particular, this group has a prolific production of bioactive secondary metabolites (SMs). In this work, four diverseAspergillusspecies (A. campestris,A. novofumigatus,A. ochraceoroseus, andA. steynii) have been whole-genome PacBio sequenced to provide genetic references in threeAspergillussections.A. taichungensisandA. candidusalso were sequenced for SM elucidation. ThirteenAspergillusgenomes were analyzed with comparative genomics to determine phylogeny and genetic diversity, showing that each presented genome contains 15-27% genes not found in other sequenced Aspergilli. In particular,A. novofumigatuswas compared with the pathogenic speciesA. fumigatusThis suggests thatA. novofumigatuscan produce most of the same allergens, virulence, and pathogenicity factors asA. fumigatus, suggesting thatA. novofumigatuscould be as pathogenic asA. fumigatusFurthermore, SMs were linked to gene clusters based on biological and chemical knowledge and analysis, genome sequences, and predictive algorithms. We thus identify putative SM clusters for aflatoxin, chlorflavonin, and ochrindol inA. ochraceoroseus,A. campestris, andA. steynii, respectively, and novofumigatonin,ent-cycloechinulin, andepi-aszonalenins inA. novofumigatusOur study delivers six fungal genomes, showing the large diversity found in theAspergillusgenus; highlights the potential for discovery of beneficial or harmful SMs; and supports reports ofA. novofumigatuspathogenicity. It also shows how biological, biochemical, and genomic information can be combined to identify genes involved in the biosynthesis of specific SMs.
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Bio Calculators
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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 ╳
