(-)-Caryophyllene oxide
(Synonyms: 石竹素,(-)-Caryophyllene oxide) 目录号 : GC45245
A bicyclic sesquiterpene
Cas No.:1139-30-6
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(-)-Caryophyllene oxide is a bicyclic sesquiterpene and a metabolite of β-caryophyllene that has been found in C. sativa and has anticancer properties. Unlike β-caryophyllene, (-)-caryophyllene oxide does not bind to the cannabinoid (CB) receptor CB2 (Ki = >20 µM). It induces calcium currents in HL-60 cells expressing CB2 receptors but also does so in CB2-deficient cells. (-)-Caryophyllene oxide is cytotoxic to HepG2, AGS, HeLa, SNU-1 and SNU-16 cells (IC50s = 3.95, 12.6, 13.55, 16.79, and 27.39 µM, respectively). It is the volatile component of C. sativa sensed by narcotic detection dogs. Formulations containing (-)-caryophyllene have been used as flavoring agents.
| Cas No. | 1139-30-6 | SDF | |
| 别名 | 石竹素,(-)-Caryophyllene oxide | ||
| Canonical SMILES | CC(C1)(C)[C@@]2([H])[C@@]1([H])C(CC[C@@H]3[C@](C)(O3)CC2)=C | ||
| 分子式 | C15H24O | 分子量 | 220.4 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 10 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS (pH 7.2) (1:3): 0.25 mg/ml | 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 | 4.5372 mL | 22.686 mL | 45.3721 mL |
| 5 mM | 0.9074 mL | 4.5372 mL | 9.0744 mL |
| 10 mM | 0.4537 mL | 2.2686 mL | 4.5372 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。
β-caryophyllene and β-caryophyllene oxide-natural compounds of anticancer and analgesic properties
Cancer Med 2016 Oct;5(10):3007-3017.PMID:27696789DOI:10.1002/cam4.816.
Natural bicyclic sesquiterpenes, β-caryophyllene (BCP) and β-Caryophyllene oxide (BCPO), are present in a large number of plants worldwide. Both BCP and BCPO (BCP(O)) possess significant anticancer activities, affecting growth and proliferation of numerous cancer cells. Nevertheless, their antineoplastic effects have hardly been investigated in vivo. In addition, both compounds potentiate the classical drug efficacy by augmenting their concentrations inside the cells. The mechanisms underlying the anticancer activities of these sesquiterpenes are poorly described. BCP is a phytocannabinoid with strong affinity to cannabinoid receptor type 2 (CB2 ), but not cannabinoid receptor type 1 (CB1 ). In opposite, BCP oxidation derivative, BCPO, does not exhibit CB1/2 binding, thus the mechanism of its action is not related to endocannabinoid system (ECS) machinery. It is known that BCPO alters several key pathways for cancer development, such as mitogen-activated protein kinase (MAPK), PI3K/AKT/mTOR/S6K1 and STAT3 pathways. In addition, treatment with this compound reduces the expression of procancer genes/proteins, while increases the levels of those with proapoptotic properties. The selective activation of CB2 may be considered a novel strategy in pain treatment, devoid of psychoactive side effects associated with CB1 stimulation. Thus, BCP as selective CB2 activator may be taken into account as potential natural analgesic drug. Moreover, due to the fact that chronic pain is often an element of cancer disease, the double activity of BCP, anticancer and analgesic, as well as its beneficial influence on the efficacy of classical chemotherapeutics, is particularly valuable in oncology. This review is focused on anticancer and analgesic activities of BCP and BCPO, the mechanisms of their actions, and potential therapeutic utility.
β-Caryophyllene oxide inhibits metastasis by downregulating MMP-2, p-p38 and p-ERK in human fibrosarcoma cells
J Food Biochem 2022 Dec;46(12):e14468.PMID:36190169DOI:10.1111/jfbc.14468.
When cancer cells transform into malignant tumors, they gain the ability to ignore growth-inhibiting signals, have endless reproduction potential, resist apoptosis, and induce angiogenesis and invade other tissues. Matrix metalloproteinases (MMPs) allow tumor cells to move into surrounding tissues in many malignancies, but metastasis is blocked by MMPs inhibitors. Therefore, the effect of β-Caryophyllene oxide (CPO) contained in Piper nigrum on Mitogen-activated protein kinase (MAPKs) related to MMPs signaling pathways in human fibrosarcoma was examined in HT1080 cells. The effect of CPO on cell viability was performed using the MTT assay. Cytotoxicity was observed in the presence of CPO above 16 μM. Next, gelatin zymography was performed in the cells activated with phorbol-12-myristate-13-acetate (PMA). It was found that CPO at 32 μM reduced MMP-9 activity by 28% and MMP-2 activity by 60%. To confirm the effect of CPO on MMPs, Western blot analyses for MMP-2, MAPKs were carried out in this study. The expression level of MMP-2 was reduced by 45% in the presence of CPO at 32 μM, but those of p-p38 and p-ERK were reduced by 50% and 40%, respectively. CPO decreased the expression levels of MMP-2 and MMP-9 in the immunofluorescence staining assay. Finally, an invasion assay was performed in PMA-treated human fibrosarcoma cells. It was demonstrated that CPO reduced cell invasion of HT1080 cells in a dose-dependent manner starting at a concentration of 2 μM. The above results suggest that CPO could be used as a potential candidate for the treatment of metastasis by inhibiting MMP-2, p-p38 and p-ERK. PRACTICAL APPLICATIONS: Cancer makes it easier for cells to spread to other tissue via blood and lymph systems. Tumor cells deplete nutrients and induce angiogenesis, which penetrates and spreads to other parts of the body. As a result, the effect of CPO against cell invasion was evaluated in this study. CPO reduced cancer cell invasion by inactivating p-ERK and p-p38, according to the findings. MMP-2 and MMP-9 activation and protein expression were also decreased by CPO. As a result, CPO might be used as an alternate treatment agent for preventing metastasis.
Excito-repellent activity of β-Caryophyllene oxide against Aedes aegypti and Anopheles minimus
Acta Trop 2019 Sep;197:105030.PMID:31121148DOI:10.1016/j.actatropica.2019.05.021.
Contact irritant and non-contact repellent activities of β-Caryophyllene oxide were evaluated against laboratory strains of female Aedes aegypti (USDA strain), a major arbovirus vector and Anopheles minimus (KU strain), a major malaria parasite vector, compared with the synthetic repellent DEET, using an excito-repellency test system. β-Caryophyllene oxide and DEET were tested at concentrations of 0.1, 0.25, 0.5 and 1.0% (v/v). Anopheles minimus was found to be more sensitive to β-Caryophyllene oxide than that of Ae. aegypti and exhibited high avoidance response rates (86-96% escape) at 0.5% and 1.0% concentrations in contact and non-contact trials compared with Ae. aegypti (22-59% escape). However, at the same concentrations, DEET displayed lower irritancy and repellency capacities against these two mosquito species (range 0-54% escape) compared to β-Caryophyllene oxide. The analysis of escape responses showed significant differences between mosquito species at all concentrations (P < 0.05) except for 0.1%. For both species, there were significant differences in irritant and repellent responses between β-Caryophyllene oxide and DEET at higher concentrations (0.5 and 1.0%).
Antinociceptive, anti-inflammatory, and cytotoxic properties of Origanum vulgare essential oil, rich with β-caryophyllene and β-Caryophyllene oxide
Korean J Pain 2022 Apr 1;35(2):140-151.PMID:35354677DOI:10.3344/kjp.2022.35.2.140.
Background: Essential oils are of great interest for their analgesic and anti-inflammatory properties. We aimed to study the content of the essential oil of the Origanum vulgare of the Armenian highlands (OVA) in different periods of vegetation and to investigate its antinociceptive and anti-inflammatory effects in mice (in vivo) and cytotoxic action in cultured cells (in vitro). OVA essential oil was extracted from fresh plant material by hydro-distillation. Methods: For OVA essential oil contents determination the gas chromatography-mass spectrometry method was used. Formalin and hot plate tests and analysis of cell viability using the methyl-thiazolyl-tetrazolium (MTT) assay were used. Results: The maximal content of β-caryophyllene and β-Caryophyllene oxide in OVA essential oil was revealed in the period of blossoming (8.18% and 13.36%, correspondently). In the formalin test, 4% OVA essential oil solution (3.5 mg/mouse) exerts significant antinociceptive and anti-inflammatory effects (P = 0.003). MTT assay shows approximately 60% cytotoxicity in HeLa and Vero cells for 2.0 μL/mL OVA essential oil in media. Conclusions: The wild oregano herb of Armenian highlands, harvested in the blossoming period, may be considered as a valuable source for developing pain-relieving preparations.
Excito-repellency and biological safety of β-Caryophyllene oxide against Aedes albopictus and Anopheles dirus (Diptera: Culicidae)
Acta Trop 2020 Oct;210:105556.PMID:32485168DOI:10.1016/j.actatropica.2020.105556.
The activity of β-Caryophyllene oxide as either a contact or noncontact repellent was evaluated against two laboratory strains (Aedes albopictus and Anopheles dirus) using an excito-repellency test system. N, N-Diethyl-3-methylbenzamide (DEET) was used as a standard reference baseline for comparative purposes. β-Caryophyllene oxide and DEET were tested at concentrations of 0.1, 0.25, 0.5 and 1.0% (v/v). In addition, the phototoxic and genotoxic effects of β-Caryophyllene oxide were investigated on Balb/c 3T3 mouse fibroblasts (3T3-L1) and Chinese hamster ovary cell line (CHO-K1). The results demonstrated that the higher concentrations of test compounds (0.5 and 1.0%) produced greater behavioral responses. Aedes albopictus was more sensitive to β-Caryophyllene oxide than An. dirus. Moderate avoidance response rates (25-56% escape) of Ae. albopictus at 0.5% and 1.0% β-Caryophyllene oxide were observed in contact and noncontact trials compared with low response rates from An. dirus (26-31% escape). DEET at ≤1% displayed lower irritancy and repellency (1-38%) than β-Caryophyllene oxide when tested against the two mosquito species. Knockdown responses (37%) were only observed in An. dirus exposed to 1% β-Caryophyllene oxide in the contact trial. β-Caryophyllene oxide did not show any phototoxic potential (PIF= 0.38) nor was there any significant genotoxic response as indicated by no increase in micro-nucleated cells with or without metabolic activation. β-Caryophyllene oxide could be considered as a safe repellent, effective against mosquitoes.