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Cycloechinulin Sale

(Synonyms: 环丙烷刺孢曲霉素) 目录号 : GC40223

A diketopiperazine fungal metabolite

Cycloechinulin Chemical Structure

Cas No.:143086-29-7

规格 价格 库存 购买数量
1mg
¥3,238.00
现货
5mg
¥14,579.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

Cycloechinulin is a diketopiperazine fungal metabolite originally isolated from A. ochraceus. It reduces weight gain of corn earworms by 33% compared to controls when used at a dose of 100 ppm in the diet.

Chemical Properties

Cas No. 143086-29-7 SDF
别名 环丙烷刺孢曲霉素
Canonical SMILES CC1(C)C2=C(C(C=CC(OC)=C3)=C3N2)/C=C4N(C([C@H](C)NC\4=O)=O)/C=C\1
分子式 C20H21N3O3 分子量 351.4
溶解度 DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.8458 mL 14.2288 mL 28.4576 mL
5 mM 0.5692 mL 2.8458 mL 5.6915 mL
10 mM 0.2846 mL 1.4229 mL 2.8458 mL
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Research Update

Novoamauromine and ent-Cycloechinulin: two new diketopiperazine derivatives from Aspergillus novofumigatus

Chem Pharm Bull (Tokyo) 2010 May;58(5):717-9.PMID:20460802DOI:10.1248/cpb.58.717.

Two new diketopiperazine metabolites, novoamauromine (1) and ent-cycloechinulin (2) have been isolated from Aspergillus novofumigatus CBS117520. The structures of 1 and 2 were established on the basis of spectroscopic and chemical investigation, including a detailed comparison of the spectroscopic and physico-chemical data of amauromine (3) and Cycloechinulin (4).

Insight into Antioxidant and Photoprotective Properties of Natural Compounds from Marine Fungus

J Chem Inf Model 2020 Mar 23;60(3):1329-1351.PMID:31999921DOI: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 compounds C1-C5 are able to scavenge two free radicals via dHAT, dSET-PT, and dSPL-ET mechanisms. Among the compounds, C3 and C4 represent 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 of C1-C5 in UVR absorption in the ranges of UVA and UVB. Among them, C3 and C4 also 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.

Suppression of RANKL-Induced Osteoclastogenesis by the Metabolites from the Marine Fungus Aspergillus flocculosus Isolated from a Sponge Stylissa sp

Mar Drugs 2018 Jan 5;16(1):14.PMID:29304006DOI: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 fungus Aspergillus flocculosus derived from a sponge Stylissa sp. collected in Vietnam. The structures of Compounds 1-5 were 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). Compounds 1-5 had 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.

Polyphasic taxonomy of Aspergillus fumigatus and related species

Mycologia 2005 Nov-Dec;97(6):1316-29.PMID:16722222DOI:10.3852/mycologia.97.6.1316.

The variability within Aspergillus fumigatus Fresenius and related species was examined using macro-, micro-morphology, growth temperature regimes and extrolite patterns. In addition, DNA analyses including partial beta-tubulin, calmodulin and actin gene sequences were used. Detailed examination of strains, considered as A. fumigatus earlier, showed that they could be divided into four groups including A. fumigatus sensu stricto, A. lentulus and two new species. The intraspecific genetic variability within A. fumigatus sensu stricto was low, the sequence differences among 23 strains of the species was at most two bases in each partial beta-tubulin and calmodulin gene. However, intraspecific morphological diversity within the species was high and delineation of the species was equivocal. Therefore, beta-tubulin and calmodulin gene sequences could be critical determinants for the delineation of the A. fumigatus sensu stricto species. A. lentulus including isolates from clinical origin, Korean soil and from a dolphin clustered into an isolated group based on beta-tubulin, calmodulin and actin gene sequences, differing from A. fumigatus by morphological characters, growth temperature and extrolite profile. A. lentulus produces the extrolites auranthine, cyclopiazonic acid, a dimeric indole of unknown structure, neosartorin, some pyripyropens, terrein and some tryptoquivalins and tryptoquivalons. Two pair of isolates (CBS 117194, 117186 and 117520, 117519) clustered into separate groups from A. fumigatus and the other Aspergillus section Fumigati species, including the teleomorph Neosartorya, are proposed as two new species. A. fumigatiaffinis spec. nov. produces the extrolites auranthine, Cycloechinulin, helvolic acid, neosartorin, palitantin, pyripyropens, tryptoquivalins and tryptoquivalons, and A. novofumigatus spec. nov. produces the extrolites cycloechinuline, helvolic acid, neosartorin, palitantin and terrein.