Thujopsene
(Synonyms: 罗汉柏烯) 目录号 : GC49503A sesquiterpene with diverse biological activities
Cas No.:470-40-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >85.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Thujopsene is a sesquiterpene that has been found in T. dolabrata and has diverse biological activities.1,2,3,4,5 It inhibits the Na+/K+-ATPase (IC50 = 25.9 µg/ml) and cytochrome P450 (CYP) isoform CYP2B6 (Ki = 0.8 µM).1,2 Thujopsene is active against Gram-positive and Gram-negative bacteria, including S. aureus, M. luteus, and S. typhimurium (MICs = 25-50 µg/ml).1 It inhibits antigen-induced β-hexosaminidase release from IgE-sensitized RBL-2H3 mast cells (IC50 = 25.1 µM) and is cytotoxic to A549 non-small cell lung cancer (NSCLC) cells with an LC50 value of 35.27 µg/ml.3,4 Thujopsene induces mortality in the mites D. farniae and T. putrescentiae (LC50s = 9.82 and 10.92 µg/cm2, respectively).5
1.Oh, I., Yang, W.-Y., Park, J., et al.In vitro Na+/K+-ATPase inhibitory activity and antimicrobial activity of sesquiterpenes isolated from Thujopsis dolabrataArch. Pharm. Res.34(12)2141-2147(2011) 2.Jeong, H.U., Kwon, S.S., Kong, T.Y., et al.Inhibitory effects of cedrol, β-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomesJ. Toxicol. Environ. Health A.77(22-24)1522-1532(2014) 3.Kim, C.-H., Lee, T., Oh, I., et al.Mast cell stabilizing effect of (-)-Elema-1,3,11(13)-trien-12-ol and thujopsene from Thujopsis dolabrata is mediated by down-regulation of interleukin-4 secretion in antigen-induced RBL-2H3 cellsBiol. Pharm. Bull.36(3)339-345(2013) 4.Bordoloi, M., Saikia, S., Kolita, B., et al.Volatile inhibitors of phosphatidylinositol-3-kinase (PI3K) pathway: Anticancer potential of aroma compounds of plant essential oilsAnticancer Agents Med. Chem.18(1)87-109(2018) 5.Kim, J.-R., Perumalsamy, H., Kwon, M.J., et al.Toxicity of hiba oil constituents and spray formulations to American house dust mites and copra mitesPest Manag. Sci.71(5)737-743(2015)
| Cas No. | 470-40-6 | SDF | Download SDF |
| 别名 | 罗汉柏烯 | ||
| Canonical SMILES | C[C@@]12[C@]3(C(C)(CCC2)C)[C@@](C(C)=CC1)([H])C3 | ||
| 分子式 | C15H24 | 分子量 | 204.4 |
| 溶解度 | Chloroform: slightly soluble,Dichloromethane: slightly 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 | 4.8924 mL | 24.4618 mL | 48.9237 mL |
| 5 mM | 0.9785 mL | 4.8924 mL | 9.7847 mL |
| 10 mM | 0.4892 mL | 2.4462 mL | 4.8924 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。
Autoregulatory properties of (+)-thujopsene and influence of environmental conditions on its production by Penicillium decumbens
Microb Ecol 2011 Nov;62(4):838-52.PMID:21744159DOI:10.1007/s00248-011-9905-9.
A Penicillium decumbens strain was collected from a water-damaged building, and the production of microbial volatile organic compounds (MVOCs) was investigated by means of headspace solid-phase microextraction, followed by GC-MS analysis. The strain was characterized by a high production of (+)-thujopsene. The influence of various temperatures, relative humidity (RH) values, substrates, and inoculum concentrations on fungal growth and (+)-thujopsene production was studied. The optimal temperature and relative humidity for P. decumbens growth were 30°C and 100% RH, respectively. In general, the more favourable the incubation parameters were for growth, the faster maximum (+)-thujopsene production was reached. Moreover, the antifungal activity of Thujopsene was tested against 16 fungal strains. The growth of five of these fungal strains was negatively affected both by Thujopsene alone and when grown in contact with the MVOCs produced by P. decumbens. Following these results and since growth of P. decumbens itself was also inhibited by Thujopsene, an autoregulatory function for this compound was proposed. Few data are present in the literature about chemical communication between fungi. The present research could, therefore, contribute to understanding fungal metabolism and behaviour in indoor environments.
Biotransformation of Thujopsene by Caragana chamlagu
J Nat Prod 2001 May;64(5):630-1.PMID:11374959DOI:10.1021/np0004000.
Biotransformation of Thujopsene (1) using a cell suspension culture of Caragana chamlagu for 14 days gave mayurone (2, 52%) and two new compounds, 3beta-hydroxy-4-thujopsene (4, 16%) and 3beta-epoxythujopsa-5beta-ol (3, 22%).
Inhibitory effects of cedrol, β-cedrene, and Thujopsene on cytochrome P450 enzyme activities in human liver microsomes
J Toxicol Environ Health A 2014;77(22-24):1522-32.PMID:25343299DOI:10.1080/15287394.2014.955906.
Cedrol, β-cedrene, and Thujopsene are bioactive sesquiterpenes found in cedar essential oil and exert antiseptic, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal activities. These compounds are used globally in traditional medicine and cosmetics. The aim of this study was to investigate the inhibitory effects of cedrol, β-cedrene, and Thujopsene on the activities of eight major human cytochrome P-450 (CYP) enzymes using human liver microsomes to assess potential β-cedrene-, cedrol-, and thujopsene-drug interactions. Cedrol, β-cedrene, and Thujopsene were found to be potent competitive inhibitors of CYP2B6-mediated bupropion hydroxylase with inhibition constant (Ki) values of 0.9, 1.6, and 0.8 μM, respectively, comparable with that of a selective CYP2B6 inhibitor, thioTEPA (Ki, 2.9 μM). Cedrol also markedly inhibited CYP3A4-mediated midazolam hydroxylation with a Ki value of 3.4 μM, whereas β-cedrene and Thujopsene moderately blocked CYP3A4. Cedrol, β-cedrene, and Thujopsene at 100 μM negligibly inhibited CYP1A2, CYP2A6, and CYP2D6 activities. Only Thujopsene was found to be a mechanism-based inhibitor of CYP2C8, CYP2C9, and CYP2C19. Cedrol and Thujopsene weakly inhibited CYP2C8, CYP2C9, and CYP2C19 activities, but β-cedrene did not. These in vitro results indicate that cedrol, β-cedrene, and Thujopsene need to be examined for potential pharmacokinetic drug interactions in vivo due to their potent inhibition of CYP2B6 and CYP3A4.
Mast cell stabilizing effect of (-)-Elema-1,3,11(13)-trien-12-ol and Thujopsene from Thujopsis dolabrata is mediated by down-regulation of interleukin-4 secretion in antigen-induced RBL-2H3 cells
Biol Pharm Bull 2013;36(3):339-45.PMID:23449323DOI:10.1248/bpb.b12-00375.
Several isolated compounds from the wood part of Thujopsis dolabrata were evaluated for their inhibitory effects against antigen-induced mast cell degranulation and interleukin-4 (IL-4) secretion, as well as IL-4 mRNA and protein expression in immunoglobulin E (IgE)-sensitized RBL-2H3 cells. Among the five isolated compounds, (-)-elema-1,3,11(13)-trien-12-ol (1) and Thujopsene (2) exhibited the potent inhibitory activity against mast cell degranulation measured by β-hexosaminidase release with IC values of 27.4 µM and 25.1 µM, respectively. These compounds also inhibited the release of IL-4 (IC values of 7.0, 6.7 µM, respectively), IL-4 mRNA expression (IC values of 16.5, 7.2 µM, respectively) and IL-4 protein expression (IC values of 17.0, 9.6 µM, respectively) in antigen-induced IgE-sensitized RBL-2H3 cells. These results suggested that (-)-elema-1,3,11(13)-trien-12-ol (1) and Thujopsene (2) effectively inhibits mast cell degranulation as well as IL-4 production, suggesting that these compounds from Thujopsis dolabrata can be used as candidates for IgE-mediated allergic disorders.
Branching out from the bisabolyl cation. Unifying mechanistic pathways to barbatene, bazzanene, chamigrene, chamipinene, cumacrene, cuprenene, dunniene, isobazzanene, iso-γ-bisabolene, isochamigrene, laurene, microbiotene, sesquithujene, sesquisabinene, Thujopsene, trichodiene, and widdradiene sesquiterpenes
J Am Chem Soc 2014 Feb 12;136(6):2450-63.PMID:24490652DOI:10.1021/ja4106489.
Quantum chemical calculations on the transformation of the bisabolyl cation into an array of sesquiterpenes (iso-γ-bisabolene, trichodiene, cuprenene, laurene, isochamigrene, chamigrene, chamipinene, sesquithujene, sesquisabinene, microbiotene, dunniene, cumacrene, isobazzanene, bazzanene, barbatene, widdradiene, and Thujopsene) are described. The bisabolyl cation is the hub of a complicated web of carbocations involved in the construction of diverse and complex molecular architectures present in a large number of Nature's sesquiterpenoids. The results of quantum chemical calculations on the multitude of rearrangements described herein provide reasonable answers to several persistent mechanistic questions in the world of terpene biosynthesis and also provide examples of general reactivity principles for terpene-forming (and other) carbocation rearrangements.