Monocerin
(Synonyms: (+)-Monocerin) 目录号 : GC47700
A fungal metabolite with diverse biological activities
Cas No.:30270-60-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >70.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Monocerin is a fungal metabolite that has been found in F. larvarum and has diverse biological activities.1,2,3 It is active against the bacteria E. coli and B. megaterium, the phytopathogenic fungus M. violaceum, and the alga C. fusca in an agar diffusion assay when used at a concentration of 50 µg/disc.1 Monocerin (17.5 µg/ml) induces mortality in adult C. erythrocephala.2 It reduces root elongation in pre-germinated S. halepense seeds when used at a concentration of 33 ppm.3
1.Zhang, W., Krohn, K., Draeger, S., et al.Bioactive isocoumarins isolated from the endophytic fungus Microdochium bolleyiJ. Nat. Prod.71(6)1078-1081(2008) 2.Claydon, N., Grove, J.F., and Pople, M.Insecticidal secondary metabolic products from the entomogenous fungus Fusarium larvarumJ. Invertebr. Pathol.33(3)364-367(1979) 3.Robeson, D.J., and Strobel, G.A.Monocerin, a phytotoxin from Exserohilum turcicum (Drechslera turcica)Agr. BioI. Chem.46(11)2681-2683(1982)
| Cas No. | 30270-60-1 | SDF | |
| 别名 | (+)-Monocerin | ||
| Canonical SMILES | COC1=C(OC)C(O)=C(C(O[C@@]2([H])[C@]3([H])O[C@@H](CCC)C2)=O)C3=C1 | ||
| 分子式 | C16H20O6 | 分子量 | 308.3 |
| 溶解度 | Dichloromethane: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 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。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.2436 mL | 16.218 mL | 32.4359 mL |
| 5 mM | 0.6487 mL | 3.2436 mL | 6.4872 mL |
| 10 mM | 0.3244 mL | 1.6218 mL | 3.2436 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Effects of Monocerin on cell cycle progression in maize root meristems synchronized with aphidicolin
Plant Cell Rep 1995 Jan;15(1-2):138-42.PMID:24185672DOI:10.1007/BF01690271.
Monocerin is a benzopyran fungal toxin with broad activity on plants, fungi and insects. Its effect upon cell cycle progression has been analyzed in maize roots. Meristematic cells were synchronized by treatment with aphidicolin. Flow cytometric DNA analysis and mitotic indices indicated durations of 1.5 h, 5 h, 2 h and 1 h for respectively G1, S, G2 and M phases of the normal cell cycle at 25°C. Treatment of these synchronized meristems with 0.5 mM Monocerin during release after an aphidicolin block produced a short delay in S phase and then a more important delay (about 2.5 h) in entry into mitosis. Treatments for similar durations (3 h) during progression through the cycle revealed two periods of action of Monocerin. The first appears to be mid to late S and the second one G2, before the transition point between G2 and M. Action on either one of these target periods could lead to a delay in the G2/M transition, but these two responses did not appear to be additive.
A concise, convergent total synthesis of Monocerin
Org Biomol Chem 2006 Nov 21;4(22):4118-26.PMID:17312966DOI:10.1039/b612256f.
A concise and convergent eight-step synthesis of the antifungal metabolite Monocerin 1 is reported. The key step involves an allylsilane metathesis/aldehyde condensation sequence to establish the core 2,3,5-trisubstituted tetrahydrofuran. End-game approaches based around intramolecular Heck chemistry revealed an interesting example of formal 6-endo cyclisation, the origin of which was probed using model substrates. The synthesis was ultimately completed by a strategy involving stepwise oxidative cleavage of the C3-ethenyl substituent.
Metabolites of a Drechslera sp. endophyte with potential as biocontrol and bioremediation agent
Nat Prod Res 2021 Nov;35(22):4508-4516.PMID:32159387DOI:10.1080/14786419.2020.1737058.
Endophytic fungi have several well-established beneficial effects on plant health and growth, and are a huge source of bioactive compounds. The endophyte Drechslera sp. strain 678, isolated from the roots of an Australian native grass Neurachne alopecuroidea, demonstrated efficacy against four plant pathogens (Pythium ultimum, Rhizoctonia solani, Botrytis cinerea, Alternaria alternata). In addition, strain 678 was capable of degrading a common additive used in gasoline, known as methyl tertiary-butyl ether (MtBE). Thus, the organic extracts obtained from the culture filtrate of strain 678 were studied. Metabolomic analysis revealed the presence of two major bioactive metabolites, Monocerin and an alkynyl substituted epoxycyclohexenone derivative, which showed good antifungal activity. The Drechslera sp. strain 678 and its compounds show promise for applications in biocontrol and bioremediation activities in agriculture or as a remediation option for MtBE contamination in soil.
Bioprospecting of antimicrobial activity of extracts of endophytic fungi from Bauhinia guianensis
Rev Argent Microbiol 2017 Jan-Mar;49(1):3-6.PMID:28094064DOI:10.1016/j.ram.2016.08.005.
Antibiotic resistance results in higher medical costs, prolonged hospital stays and increased mortality and is rising to dangerously high levels in all parts of the world. Therefore, this study aims to search for new antimicrobial agents through bioprospecting of extracts of endophytic fungi from Bauhinia guianensis, a typical Amazonian plant used in combating infections. Seventeen (17) fungi were isolated and as result the methanolic extract of the fungus Exserohilum rostratum showed good activity against the bacteria tested. The polyketide Monocerin was isolated by the chromatographic technique, identified by NMR and MS, showing broad antimicrobial spectrum.
Asymmetric synthesis of 4,8-dihydroxyisochroman-1-one polyketide metabolites using chiral hypervalent iodine(III)
Org Lett 2012 Mar 2;14(5):1294-7.PMID:22335341DOI:10.1021/ol300185u.
Stereoselective oxylactonization of ortho-alkenylbenzoate with chiral hypervalent iodine is applied to the asymmetric synthesis of 4-oxyisochroman-1-one polyketide metabolites including 4-hydroxymellein (1), a derivative of fusarentin 2, Monocerin (3), and an epimer of Monocerin epi-3.