Kakuol
(Synonyms: 卡枯醇) 目录号 : GC39001
Kakuol 是一种从 Asarum sieboldii 根茎中分离得到的天然化合物，具有抗真菌活性。
Cas No.:18607-90-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Kakuol is a natural compound isolated from the rhizomes of Asarum sieboldii. Antifungal activity[1].
[1]. Lee JY, et al. Isolation and antifungal activity of kakuol, a propiophenone derivative from Asarum sieboldii rhizome. Pest Manag Sci. 2005 Aug;61(8):821-5.
| Cas No. | 18607-90-4 | SDF | |
| 别名 | 卡枯醇 | ||
| Canonical SMILES | CCC(C1=C(O)C=C(OCO2)C2=C1)=O | ||
| 分子式 | C10H10O4 | 分子量 | 194.18 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°C, protect from light |
| 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 | 5.1499 mL | 25.7493 mL | 51.4986 mL |
| 5 mM | 1.03 mL | 5.1499 mL | 10.2997 mL |
| 10 mM | 0.515 mL | 2.5749 mL | 5.1499 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。
Isolation and antifungal activity of Kakuol, a propiophenone derivative from Asarum sieboldii rhizome
Pest Manag Sci 2005 Aug;61(8):821-5.PMID:15846774DOI:10.1002/ps.1050.
An antifungal substance active against Colletotrichum orbiculare (Berk & Mont) Arx was isolated from the methanol extracts of Asarum sieboldii (Miq) Maek rhizomes. High-resolution MS, NMR and UV spectral data confirmed that the antifungal substance is Kakuol, 2-hydroxy-4,5-methylenedioxypropiophenone. Colletotrichum orbiculare was most sensitive to Kakuol, with MIC of 10 microg ml(-1). Kakuol also completely inhibited the mycelial growth of Botrytis cinerea Pers ex Fr and Cladosporium cucumerinum Ellis & Arthur at 50 microg ml(-1) and 30 microg ml(-1), respectively. However, no antimicrobial activity was found against yeast and bacteria even at 100 microg ml(-1). Kakuol exhibited a protective activity against the development of anthracnose disease on cucumber plants. The control efficacy of Kakuol against the anthracnose disease was in general somewhat less than that of the commercial fungicide chlorothalonil. This is the first report to demonstrate in vitro and in vivo antifungal activity of Kakuol against C. orbiculare infection.
Design, synthesis and antifungal activity of amide and imine derivatives containing a Kakuol moiety
Bioorg Med Chem Lett 2020 Jan 1;30(1):126774.PMID:31685339DOI:10.1016/j.bmcl.2019.126774.
In continuation of our program to discover new potential antifungal agents, a series of amide and imine derivatives containing a Kakuol moiety were synthesized and characterized by the spectroscopic analysis. By using the mycelium growth rate method, the target compounds were evaluated systematically for antifungal activities in vitro against four plant pathogenic fungi, and structure-activity relationships (SAR) were derived. Compounds 7d, 7e, 7h, 7i and 7r showed obvious inhibitory activity against the corresponding tested fungi at 50 μg/mL. Especially, compounds 7e and 7r displayed more potent antifungal activity against B. cinerea than that of thiabendazole (a positive control). Moreover, compound 7e also exhibited good activity against A. alternata with EC50 values of 11.0 µg/mL, and the value was slightly superior to that of thiabendazole (EC50 = 14.9 µg/mL). SAR analysis showed that the ether group was a highly sensitive structural moiety to the activity and the type as well as position of substituents on benzene ring could make some effects on the activity.
A derivative of the natural compound Kakuol affects DNA relaxation of topoisomerase IB inhibiting the cleavage reaction
Arch Biochem Biophys 2013 Feb 1;530(1):7-12.PMID:23262316DOI:10.1016/j.abb.2012.12.013.
Topoisomerases IB are anticancer and antimicrobial targets whose inhibition by several natural and synthetic compounds has been documented over the last three decades. Here we show that Kakuol, a natural compound isolated from the rhizomes of Asarum sieboldii, and a derivative analogue are able to inhibit the DNA relaxation mediated by the human enzyme. The analogue is the most efficient one and the inhibitory effect is enhanced upon pre-incubation with the enzyme. Analysis of the different steps of the catalytic cycle indicates that the inhibition occurs at the cleavage level and does not prevent DNA binding. Molecular docking shows that the compound preferentially binds near the active site at the bottom of the catalytic residue Tyr723, providing an atomistic explanation for its inhibitory activity.
Synthesis and antifungal activity of 2-hydroxy-4,5-methylenedioxyaryl ketones as analogues of Kakuol
Chem Biodivers 2010 Apr;7(4):887-97.PMID:20397224DOI:10.1002/cbdv.200900263.
In a study aiming to determine the structural elements essential to the antifungal activity of Kakuol, we synthesized a series of 2-hydroxy-4,5-methylenedioxyaryl ketones, and we assayed their in vitro antifungal activity. The most sensitive target organisms to the action of these class of compounds were Phytophthora infestans, Phytium ultimum, Cercospora beticola, Cladosporium cucumerinum, and Rhizoctonia solani. Most of the analogs showed a remarkable in vitro activity, and some of them appeared significantly more effective than the natural product. The biological activity was mainly affected by introducing structural modification on the carbonyl moiety of the natural-product molecule. In particular, compound 5a, bearing a C=C bond conjugated to the C=O group, was found active with a MIC value of 10 microg ml(-1) against Cladosporium cucumerinum. The results suggest that 2-hydroxy-4,5-methylenedioxyaryl ketones can be considered promising candidates in the development of new antifungal compounds.
Simultaneous determination of six constituents in Mahuang Fuzi Xixin by UPLC-PDA-MS/MS
Nat Prod Res 2015;29(8):772-5.PMID:25428280DOI:10.1080/14786419.2014.983104.
Mahuang Fuzi Xixin (MFX), a classic recipe in traditional Chinese medicine, belongs to an exterior-relieving formula. For quality control of the MFX products, qualitative analysis using ultra-high performance liquid chromatography with diode-array detector-tandem mass spectrometry (UPLC-PDA-MS/MS) was undertaken. Six compounds from the MFX were simultaneously detected. Among them, astragalin and kaempferol 3-rutinoside were quantified through the UPLC-MS/MS method, while asarinin, sesamin, Kakuol and methyleugenol were quantified through the UPLC-PDA method. This method can be applied to the quantitative determination of the six compounds in the MFX.