Drimendiol
目录号 : GC46135
A sesquiterpene
Cas No.:34437-62-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Drimendiol is a sesquiterpene that has been found in W. ugandensis.1 It inhibits C. albicans, S. aureus, and S. epidermidis biofilm formation with 50% biofilm inhibitory concentration values (BIC50s) of 25.5, 65.1, and 67.1 μg/ml, respectively. It has antifouling activity, inhibiting the settlement of C. savignyi and B. improvisus larvae on a petri dish surface (EC50s = 1 and 0.5 μg/ml, respectively).2
|1. Kipanga, P.N., Liu, M., Panda, S.K., et al. Biofilm inhibiting properties of compounds from the leaves of Warburgia ugandensis Sprague subsp ugandensis against Candida and staphylococcal biofilms. J. Ethnopharmacol. 248:112352, (2020).|2. Moodie, L.W., Trepos, R., Cervin, G., et al. Probing the structure-activity relationship of the natural antifouling agent polygodial against both micro- and macrofoulers by semisynthetic modification. J. Nat. Prod. 80(2), 515-525 (2017).
| Cas No. | 34437-62-2 | SDF | |
| Canonical SMILES | OC[C@H]1C(CO)=CC[C@@]2([H])C(C)(C)CCC[C@@]21C | ||
| 分子式 | C15H26O2 | 分子量 | 238.4 |
| 溶解度 | Soluble in DMSO | 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 | 4.1946 mL | 20.9732 mL | 41.9463 mL |
| 5 mM | 0.8389 mL | 4.1946 mL | 8.3893 mL |
| 10 mM | 0.4195 mL | 2.0973 mL | 4.1946 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。
Drimendiol, a drimane sesquiterpene with quorum sensing inhibition activity
Nat Prod Commun 2013 Feb;8(2):147-8.PMID:23513712doi
Quorum sensing (QS) is a regulatory mechanism that enables bacteria to make collective decisions such as an increase in virulence factors and biofilm production. Inhibitors of QS are important research tools in the discovery of new potential anti-bacterial agents. Polygodial, drimenol and Drimendiol are drimane sesquiterpenoids isolated from Drimys winteri, a Chilean native tree. Their QS activity, when tested on Chromobacterium violaceum ATCC 12472, showed that Drimendiol is an inhibitor of QS, decreasing violaceine production in C violaceum and decreasing biofilm formation of Pseudomonas syringae strains. Consequently it increased the biocide effects of CuSO4 on biofilms of P. syringae.
Drimane Sesquiterpene Alcohols with Activity against Candida Yeast Obtained by Biotransformation with Cladosporium antarcticum
Int J Mol Sci 2022 Oct 27;23(21):12995.PMID:36361785DOI:10.3390/ijms232112995.
Fungal biotransformation is an attractive synthetic strategy to produce highly specific compounds with chemical functionality in regions of the carbon skeleton that are not easily activated by conventional organic chemistry methods. In this work, Cladosporium antarcticum isolated from sediments of Glacier Collins in Antarctica was used to obtain novel drimane sesquiterpenoids alcohols with activity against Candida yeast from Drimendiol and epidrimendiol. These compounds were produced by the high-yield reduction of polygodial and isotadeonal with NaBH4 in methanol. Cladosporium antarcticum produced two major products from Drimendiol, identified as 9α-hydroxydrimendiol (1, 41.4 mg, 19.4% yield) and 3β-hydroxydrimendiol (2, 74.8 mg, 35% yield), whereas the biotransformation of epidrimendiol yielded only one product, 9β-hydroxyepidrimendiol (3, 86.6 mg, 41.6% yield). The products were purified by column chromatography and their structure elucidated by NMR and MS. The antifungal activity of compounds 1-3 was analyzed against Candida albicans, C. krusei and C. parapsilosis, showing that compound 2 has a MIC lower than 15 µg/mL against the three-pathogenic yeast. In silico studies suggest that a possible mechanism of action for the novel compounds is the inhibition of the enzyme lanosterol 14α-demethylase, affecting the ergosterol synthesis.
Identification of a drimenol synthase and drimenol oxidase from Persicaria hydropiper, involved in the biosynthesis of insect deterrent drimanes
Plant J 2017 Jun;90(6):1052-1063.PMID:28258968DOI:10.1111/tpj.13527.
The sesquiterpenoid polygodial, which belongs to the drimane family, has been shown to be an antifeedant for a number of herbivorous insects. It is presumed to be synthesized from farnesyl diphosphate via drimenol, subsequent C-12 hydroxylation and further oxidations at both C-11 and C-12 to form a dialdehyde. Here, we have identified a drimenol synthase (PhDS) and a cytochrome P450 drimenol oxidase (PhDOX1) from Persicaria hydropiper. Expression of PhDS in yeast and plants resulted in production of drimenol alone. Co-expression of PhDS with PhDOX1 in yeast yielded Drimendiol, the 12-hydroxylation product of drimenol, as a major product, and cinnamolide. When PhDS and PhDOX1 were transiently expressed by agro-infiltration in Nicotiana benthamiana leaves, drimenol was almost completely converted into cinnamolide and several additional drimenol derivatives were observed. In vitro assays showed that PhDOX1 only catalyses the conversion from drimenol to Drimendiol, and not the further oxidation into an aldehyde. In yeast and heterologous plant hosts, the C-12 position of Drimendiol is therefore likely to be further oxidized by endogenous enzymes into an aldehyde and subsequently converted to cinnamolide, presumably by spontaneous hemiacetal formation with the C-11 hydroxyl group followed by oxidation. Purified cinnamolide was confirmed by NMR and shown to be deterrent with an effective deterrent dose (ED50 ) of about 200-400 μg g-1 fresh weight against both whiteflies and aphids. The putative additional physiological and biochemical requirements for polygodial biosynthesis and stable storage in plant tissues are discussed.
Practical isolation of polygodial from Tasmannia lanceolata: a viable scaffold for synthesis
Org Biomol Chem 2015 Dec 14;13(46):11200-7.PMID:26377594DOI:10.1039/c5ob01573a.
Polygodial, a valuable sesquiterpene dialdehyde featuring an epimerizable stereocenter was efficiently extracted and isolated in gram-scale quantities (3.3% w/w) from Tasmannia lanceolata (Tasmanian native pepper) via a recently developed rapid pressurised hot water extraction (PHWE) technique that utilises an unmodified household espresso machine. This method was compared to the maceration of T. lanceolata under a range of conditions. Polygodial was used to achieve semi-syntheses of closely related sesquiterpene natural products Drimendiol, (-)-drimenol, (+)-euryfuran, and some non-natural derivatives.
Biofilm inhibiting properties of compounds from the leaves of Warburgia ugandensis Sprague subsp ugandensis against Candida and staphylococcal biofilms
J Ethnopharmacol 2020 Feb 10;248:112352.PMID:31676401DOI:10.1016/j.jep.2019.112352.
Ethnopharmacological relevance: Warburgia ugandensis Sprague subspecies ugandensis is a plant widely distributed in Eastern, Central and Southern Africa. In humans, it is used to treat respiratory infections, tooth aches, malaria, skin infections, venereal diseases, diarrhea, fevers and aches. Aim of the study: This study aims to identify the bioactive compounds against clinically important biofilm-forming strains of Candida and staphylococci that are responsible for tissue and implanted device-related infections. Methods: Using a bioassay-guided fractionation approach, hexane -, ethanol -, acetone - and water extracts from the leaves of W. ugandensis, their subsequent fractions and isolated compounds were tested against both developing and preformed 24 h-biofilms of Candida albicans SC5314, Candida glabrata BG2, Candida glabrata ATCC 2001, Staphylococcus epidermidis 1457 and Staphylococcus aureus USA 300 using microtiter susceptibility tests. Planktonic cells were also tested in parallel for comparison purposes. Confocal scanning laser microscopy was also used to visualize effects of isolated compounds on biofilm formation. Results: Warburganal, polygodial and alpha-linolenic acid (ALA) were the major bioactive compounds isolated from the acetone extract of W. ugandensis. For both warburganal and polygodial, the biofilm inhibitory concentration that inhibits 50% of C. albicans developing biofilms (BIC50) was 4.5 ± 1 and 10.8 ± 5 μg/mL respectively. Against S. aureus developing biofilms, this value was 37.9 ± 8 μg/mL and 25 μg/mL with warburganal and ALA respectively. Eradication of preformed 24 h biofilms was also observed. Interestingly, synergy between the sesquiterpenoids and azoles against developing C. albicans biofilms resulted in an approximately ten-fold decrease of the effective concentration required to completely inhibit growth of the biofilms by individual compounds. The hydroxyl group in position C-9 in warburganal was identified as essential for activity against staphylococcal biofilms. We also identified additional promising bioactive sesquiterpenoids; drimenol and Drimendiol from the structure-activity relationship (SAR) studies. Conclusions: ALA and four sesquiterpenoids: polygodial, warburganal, drimenol and Drimendiol, have shown biofilm-inhibitory activity that has not been reported before and is worth following up. These compounds are potential drug candidates to manage biofilm-based infections, possibly in combination with azoles.