Benanomicin A
(Synonyms: 贝那霉素) 目录号 : GC49038
A microbial metabolite with antifungal, fungicidal, and antiviral activities
Cas No.:116249-65-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Benanomicin A is a microbial metabolite that has been found in Actinomycetes and has antifungal, fungicidal, and antiviral activities.1,2 It is active against a variety of mammalian and plant pathogenic fungi, including C. albicans, T. mentagrophytes, C. neoformans, P. oryzae, and A. niger (MICs = 3.13-50 µg/ml).1 Benanomicin A inhibits HIV-1 viral infection in MT-4 cells in a concentration-dependent manner.2
1.Takeuchi, T., Hara, T., Naganawa, H., et al.New antifungal antibiotics, benanomicins A and B from an actinomyceteJ. Antibiot. (Tokyo)41(6)807-811(1987) 2.Kondo, S., Gomi, S., Ikeda, D., et al.Antifungal and antiviral activities of benanomicins and their analoguesJ. Antibiot. (Tokyo)44(11)1228-1236(1990)
| Cas No. | 116249-65-1 | SDF | |
| 别名 | 贝那霉素 | ||
| Canonical SMILES | OC1=C2C3=C(O)C(C(C4=CC(OC)=CC(O)=C4C5=O)=O)=C5C=C3[C@@H]([C@H](C2=CC(C)=C1C(N[C@H](C)C(O)=O)=O)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)C)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O)O | ||
| 分子式 | C39H41NO19 | 分子量 | 827.7 |
| 溶解度 | Ethanol: soluble | 储存条件 | -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 | 1.2082 mL | 6.0408 mL | 12.0817 mL |
| 5 mM | 0.2416 mL | 1.2082 mL | 2.4163 mL |
| 10 mM | 0.1208 mL | 0.6041 mL | 1.2082 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。
Amino acid analogs of Benanomicin A through desalaninebenanomicin A
J Antibiot (Tokyo) 1992 Oct;45(10):1645-52.PMID:1473992DOI:10.7164/antibiotics.45.1645.
Desalaninebenanomicin A has been synthesized in good yield by the cleavage of the amido bond of Benanomicin A using MEERWEIN's reagent. This is a useful intermediate to prepare amino acid analogs of Benanomicin A. MEERWEIN's reagent reacts with totally protected Benanomicin A to give a stable imino ether. After deprotection, the imino ether is treated with aqueous acetone at reflux to afford a methyl ester of desalaninebenanomicin A. Desalaninebenanomicin A was coupled with a variety of amino acids by the active ester method to afford new benanomicin analogs.
Binding of Benanomicin A to fungal cells in reference to its fungicidal action
J Antibiot (Tokyo) 1996 Apr;49(4):366-73.PMID:8642000DOI:10.7164/antibiotics.49.366.
An antifungal antibiotic, Benanomicin A, binds in the presence of Ca2+ to susceptible fungi and some bacteria, but not to antibiotic-resistant bacteria and mammalian cells. With the susceptible yeast Saccharomyces cerevisiae, Benanomicin A binds similarly to whole cells and to protoplasts. Studies using Benanomicin A and three structurally related derivatives suggested that a carboxylic acid in the D-alanine moiety and a sugar moiety in the Benanomicin A molecule are essential for both binding and antifungal activities against growing S. cerevisiae. An amino substituent on the sugar moiety can be replaced with a hydroxyl group without the loss of activities. Benanomicin A binds to various yeast mannans which differ in glycosidic linkages. These results indicate that binding of Benanomicin A to the mannan portion of fungal cells is essential for exertion of the antifungal activity.
Mode of antifungal action of Benanomicin A in Saccharomyces cerevisiae
J Antibiot (Tokyo) 1997 Dec;50(12):1042-51.PMID:9510912DOI:10.7164/antibiotics.50.1042.
The mechanism of fungitoxic action of an antifungal antibiotic Benanomicin A was studied with intact cells and protoplasts of Saccharomyces cerevisiae as well as with its enzymic preparations. The results obtained are summarized as follows: (1) Benanomicin A at relatively high concentrations (almost equal to MIC) was fungicidal and disrupted the cell permeability barrier, inducing leakage of intracellular K+ and ATP in growing cells, while the antibiotic had none of these effects in non-growing cells; (2) no biosynthesis of any of several major cellular constituents in yeast cells was inhibited markedly or selectively enough to explain its fungitoxic activity; (3) whereas Benanomicin A induced lysis of metabolically active yeast protoplasts incubated in the presence of glucose, inactive yeast protoplasts incubated without glucose were refractory to the lytic action of the antibiotic; (4) osmotically shocked yeast cells became feasible to the cidal action of Benanomicin A; (5) Benanomicin A substantially inhibited uptake of 6-deoxy-glucose by yeast cells; (6) liposomes composed of phospholipids and cholesterol were not susceptible to Benanomicin A; and (7) Benanomicin A inhibited in vitro activity of H(+)-ATPase from yeast cell membranes to a greater extent than that for H(+)-ATPase from yeast mitochondria or H(+)-ATPase from yeast vacuolar membranes. Based on these and our previous data that Benanomicin A preferentially binds to mannan or mannoproteins constituting the cell wall and cell membrane of yeasts, such binding of the antibiotic is suggested to deteriorate the normal structure and function of those cell membranes of yeasts which are in a growing or metabolically active state, ultimately leading to cell death.
Presence of O-glycosidically linked oligosaccharides in the cell wall mannan of Candida krusei purified with Benanomicin A
FEBS Open Bio 2018 Dec 10;9(1):129-136.PMID:30652080DOI:10.1002/2211-5463.12558.
Cell wall mannan of the pathogenic yeast Candida krusei was prepared using the antibiotic Benanomicin A, which has a lectin-like function. The chemical structure of this molecule was found to be similar to that of mannan prepared from the same yeast by the conventional method using Fehling reagent. Only a few degradation products were detected when the mannan prepared using Fehling reagent was subjected to alkali treatment (β-elimination), but multiple α-1,2-linked oligosaccharides were detected when the mannan purified with Benanomicin A was treated with alkali. These results indicate that most of the O-linked sugar chains in mannan were lost under conventional conditions when exposed to the strongly alkaline Fehling reagent. In contrast, the O-glycosidic bond in mannan was not cleaved and the O-linked sugar chains were maintained and almost intact following treatment with the mild novel preparation method using Benanomicin A. Therefore, we argue that the new mannan preparation method using Benanomicin A is superior to conventional methods. In addition, our study suggests that some yeast mannans, whose overall structure has already been reported, may contain more O-linked sugar chains than previously recognized.
A synthetic approach to Benanomicin A. 1. Synthesis of 5,6-dihydrobenzo[a]naphthacenequinone
J Antibiot (Tokyo) 1997 Aug;50(8):685-9.PMID:9315082DOI:10.7164/antibiotics.50.685.
5,6-Dihydrobenzo[a]naphthacenequinone has been constructed by Diels-Alder reaction of an outer-ring diene with a naphthoquinone regioselectively. Similarly, the 14-hydroxy-5,6-dihydrobenzo[a]naphthacenequinone (13) has also been synthesized via the reaction of vinylketene acetal (11) with naphthoquinone.