Aromadendrene
(Synonyms: (+)-香橙烯) 目录号 : GC49103
A sesquiterpene with diverse biological activities
Cas No.:489-39-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >80.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Aromadendrene is a sesquiterpene that has been found in E. globulus and has diverse biological activities.1,2,3 It is active against various strains of methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE; MICs = 0.25-1 mg/ml).1 Aromadendrene (1 mM) inhibits tert-butyl hydroperoxide-induced formation of thiobarbituric acid reactive substances (TBARS) in isolated rat liver hepatocytes.2 It inhibits the proliferation of HepG2 liver and PC3 prostate cancer cells (IC50s = 20 and 9.3 µM, respectively).3
1.Mulyaningsih, S., Sporer, F., Reichling, J., et al.Antibacterial activity of essential oils from Eucalyptus and of selected components against multidrug-resistant bacterial pathogensPharm. Biol.49(9)893-899(2011) 2.Vinholes, J., Rudnitskaya, A., GonÇalves, P., et al.Hepatoprotection of sesquiterpenoids: a quantitative structure-activity relationship (QSAR) approachFood Chem.14678-84(2014) 3.Al-Lihaibi, S.S., Alarif, W.M., Abdel-Lateff, A., et al.Three new cembranoid-type diterpenes from Red Sea soft coral Sarcophyton glaucum: isolation and antiproliferative activity against HepG2 cellsEur. J. Med. Chem.81314-322(2014)
| Cas No. | 489-39-4 | SDF | |
| 别名 | (+)-香橙烯 | ||
| Canonical SMILES | CC1([C@@]2([H])[C@@]3([H])[C@](CC[C@H]3C)([H])C(CC[C@]21[H])=C)C | ||
| 分子式 | C15H24 | 分子量 | 204.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml | 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。
Aromadendrene oxide 2, induces apoptosis in skin epidermoid cancer cells through ROS mediated mitochondrial pathway
Life Sci 2018 Mar 15;197:19-29.PMID:29407546DOI:10.1016/j.lfs.2018.01.029.
Aims: Aromadendrene oxide 2 (AO-(2)) is an oxygenated sesquiterpene naturally found as a chemical component of essential oils. In the present study anticancer activity of AO-(2) has been investigated on A431 human epidermoid cancer and precancerous HaCaT cells. Material and methods: Cell viability was used to detect cytotoxic activity. Mechanism of cell death induced by AO-(2) treatments was studied using Annexin V-FITC/PI binding, cell cycle analysis, measurement of MMP and ROS generation by flow cytometry. Expression of apoptosis related proteins was investigated by western blot. Key findings: AO-(2) inhibited the growth and colony formation ability of A431 and HaCaT cells in concentration dependent manner. It induced cell cycle arrest at G0/G1 phase and apoptosis through intracellular ROS accumulation. Inhibition of intracellular ROS by ascorbic acid and N-acetyl cysteine treatment completely blocked apoptotic effect. N-acetyl cysteine treatment significantly reversed G0/G1 arrest induced by AO-(2). AO-(2) treatment caused loss of mitochondrial membrane potential (ΔΨm), increase in Bax/Bcl-2 ratios, cytochrome c release, activation of caspases (cleaved caspase-3 and caspase-9) and PARP cleavage. AO-(2) also significantly inhibited the growth of multicellular tumor spheroids of A431 and HaCaT cells. Significance: The results of the present study reveals that AO-(2) a chemical component of essential oils induces apoptosis in A431 and HaCaT cells.
Synergistic properties of the terpenoids Aromadendrene and 1,8-cineole from the essential oil of Eucalyptus globulus against antibiotic-susceptible and antibiotic-resistant pathogens
Phytomedicine 2010 Nov;17(13):1061-6.PMID:20727725DOI:10.1016/j.phymed.2010.06.018.
The aim of the present study was to investigate the chemical composition of the essential oil of the fruits of Eucalyptus globulus and to examine the potential application of the fruit oil against multidrug-resistant bacteria. GLC/MS analysis in the fruit oil showed that Aromadendrene was the main compound followed by 1,8-cineole and globulol. The three most abundant components of the fruit oil were also tested individually against microorganisms. In addition, the synergistic effects of combinations of the major constituents (Aromadendrene and 1,8-cineole) of the fruit oil were also investigated. All Gram-positive bacteria were susceptible to the fruit oil with different degrees of susceptibility as determined by microdilution method. The oil exerted a marked inhibition against multidrug-resistant bacteria such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) Enterococcus faecalis. The results indicated that Aromadendrene might be responsible for the antimicrobial properties, whereas 1,8-cineole and globulol exhibited low activities. The checkerboard assay demonstrated that combinations of 1,8-cineole and Aromadendrene reduce the MIC in most cases in an additive way, whereas the time-kill assay indicates a synergistic effect.
Synergistic interaction of β-caryophyllene with Aromadendrene oxide 2 and phytol induces apoptosis on skin epidermoid cancer cells
Phytomedicine 2018 Aug 1;47:121-134.PMID:30166097DOI:10.1016/j.phymed.2018.05.001.
Background: Pamburus missionis (Wight) Swingle (Rutaceae) is traditionally used in the treatment of swellings, chronic rheumatism, paralysis and puerperal diseases. In a previous study the authors demonstrated apoptotic activity of Pamburus missionis essential oil (EO) on A431 and HaCaT cells. The major components of EO were β-caryophyllene (25.40%), 4(14),11- eudesmadiene (7.17%), Aromadendrene oxide 2 (14.01%) (AO-(2) and phytol (6.88%). Purpose of study: To investigate the role as well as the interactions among EO components inducing apoptosis in A431 and HaCaT cells. Methods: Isobolographic analysis and combination index methods were used to detect the type of interactions among the essential oil (EO) components. Cell viability was used to detect cytotoxic activity. Mechanism of cell death was studied using Annexin V-FITC/PI binding assay, cell cycle analysis, measurement of MMP and ROS generation by flow cytometry. Expression of apoptosis associated proteins was investigated by western blot. Results: Combination of P. missionis EO components: β-caryophyllene/ Aromadendrene oxide 2 (β-C/AO-(2)), β-caryophyllene/phytol (β-C/P) and Aromadendrene oxide 2 /phytol (AO-(2)/P) inhibited growth and colony formation ability of skin epidermoid A431 and precancerous HaCaT cells. Synergistic interaction was observed between β-C/AO-(2) and β-C/P combination while AO-(2)/P exhibited an additive effect. Combination of components induced chromatin condensation, phosphatidylserine externalisation, increase in sub-G1 DNA content, cell cycle arrest at G0/G1 phase and intracellular ROS accumulation. Inhibition of intracellular ROS by N-acetyl cysteine treatment blocked apoptosis induced by the combinations. The combinations induced apoptosis in A431 and HaCaT cells mediated by loss of mitochondrial membrane potential (ΔΨm), increase in Bax/Bcl-2 ratio, release of cytosolic cytochrome c and activation of caspases (cleaved form of caspase-3, caspase-8, caspase-9) and by PARP cleavage. Conclusion: The present study demonstrates interactions among β-C, AO-(2) and P in the induction of apoptosis on A431 and HaCaT cells. These data suggest the combination of β-caryophyllene with Aromadendrene oxide 2 and phytol could be potential therapeutics for the treatment of skin epidermoid cancer and precancerous cells.
Mechanistic Insights into the Neuroprotective Potential of Sacred Ficus Trees
Nutrients 2022 Nov 9;14(22):4731.PMID:36432418DOI:10.3390/nu14224731.
Ficus religiosa (Bo tree or sacred fig) and Ficus benghalensis (Indian banyan) are of immense spiritual and therapeutic importance. Various parts of these trees have been investigated for their antioxidant, antimicrobial, anticonvulsant, antidiabetic, anti-inflammatory, analgesic, hepatoprotective, dermoprotective, and nephroprotective properties. Previous reviews of Ficus mostly discussed traditional usages, photochemistry, and pharmacological activities, though comprehensive reviews of the neuroprotective potential of these Ficus species extracts and/or their important phytocompounds are lacking. The interesting phytocompounds from these trees include many bengalenosides, carotenoids, flavonoids (leucopelargonidin-3-O-β-d-glucopyranoside, leucopelargonidin-3-O-α-l-rhamnopyranoside, lupeol, cetyl behenate, and α-amyrin acetate), flavonols (kaempferol, quercetin, myricetin), leucocyanidin, phytosterols (bergapten, bergaptol, lanosterol, β-sitosterol, stigmasterol), terpenes (α-thujene, α-pinene, β-pinene, α-terpinene, limonene, β-ocimene, β-bourbonene, β-caryophyllene, α-trans-bergamotene, α-copaene, Aromadendrene, α-humulene, alloaromadendrene, germacrene, γ-cadinene, and δ-cadinene), and diverse polyphenols (tannin, wax, saponin, leucoanthocyanin), contributing significantly to their pharmacological effects, ranging from antimicrobial action to neuroprotection. This review presents extensive mechanistic insights into the neuroprotective potential, especially important phytochemicals from F. religiosa and F. benghalensis. Owing to the complex pathophysiology of neurodegenerative disorders (NDDs), the currently existing drugs merely alleviate the symptoms. Hence, bioactive compounds with potent neuroprotective effects through a multitarget approach would be of great interest in developing pharmacophores for the treatment of NDDs.
Induction of defensive response in Eucalyptus globulus plants and its persistence in vegetative propagation
Nat Prod Commun 2013 Mar;8(3):397-400.PMID:23678820doi
The expression of defensive compounds derived from secondary metabolism in plants of Eucalyptus globulus Labill, and the persistence of these in vegetative propagation was evaluated by gas chromatography with flame ionization (GC-FID) and mass spectrometry (MS). The plants were induced by attack from the insect Ctenarytaina eucalypti ("blue gum psyllid") and by mechanical damage. Defense responses were activated in plants for the different types of tested induction. We identified four defensive compounds present in the leaves of plants induced in entomological form (beta-terpineol, Aromadendrene, caryophyllene-oxide and eremophilene); all remained in the vegetative propagation. After mechanical induction, we identified three compounds (beta-terpineol, Aromadendrene and ledol), of which ledol and Aromadendrene persisted in the vegetative propagation. Virtually all the compounds detected, in addition to persisting in the vegetative propagation, showed specificity for the induction type, whether entomological or mechanical, except for Aromadendrene, which was expressed in both types of induction.