(R)-(+)-Pulegone
(Synonyms: 胡薄荷酮) 目录号 : GC40696
A monoterpene with anti-inflammatory activity
Cas No.:89-82-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >93.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(R)-(+)-Pulegone is a monoterpene that has been found in a variety of plants, including Labiatae species and M. verticillata, and has anti-inflammatory activity. It stimulates proliferation of lymphocytes derived from allergic patients in vitro when used at concentrations of 6.2 and 62 µg/ml and reduces the level of IL-13 in supernatant from lymphocyte cultures when used at a concentration of 62 µg/ml. (R)-(+)-Pulegone decreases scratching behavior and reduces skin thickness in a mouse model of atopic dermatitis when administered topically at doses ranging from 0.1 to 10 µM. It also decreases serum IgE levels and skin protein levels of nerve growth factor, IFN-γ, IL-6, IL-1β, TNF-α, NF-κB, phosphorylated ERK1/2, and phosphorylated JNK.
| Cas No. | 89-82-7 | SDF | |
| 别名 | 胡薄荷酮 | ||
| Canonical SMILES | O=C(C[C@H](C)CC/1)C1=C(C)\C | ||
| 分子式 | C10H16O | 分子量 | 152.2 |
| 溶解度 | DMSO : ≥ 270 mg/mL (1773.63 mM) | 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 | 6.5703 mL | 32.8515 mL | 65.703 mL |
| 5 mM | 1.3141 mL | 6.5703 mL | 13.1406 mL |
| 10 mM | 0.657 mL | 3.2852 mL | 6.5703 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。
Investigations of mechanisms of reactive metabolite formation from (R)-(+)-pulegone
Xenobiotica 1992 Sep-Oct;22(9-10):1157-64.PMID:1441606DOI:10.3109/00498259209051869.
1. (R)-(+)-Pulegone is a monoterpene that is oxidized by cytochromes P-450 to reactive metabolites that initiate events in the pathogenesis of hepatotoxicity in mice, rats and humans. 2. Selective labelling of (R)-(+)-pulegone with deuterium revealed that menthofuran was a proximate hepatotoxic metabolite formed by oxidation of the allylic methyl groups of pulegone. Incubations of pulegone with mouse liver microsomes in an atmosphere of 18O2 resulted in the formation of menthofuran that contained only oxygen-18 in the furan moiety. These results are consistent with oxidation of pulegone to an allylic alcohol that reacts intramolecularly with the ketone moiety to form a hemiketal that subsequently dehydrates to generate menthofuran. 3. Studies on the metabolism of menthofuran revealed that it is oxidized by cytochromes P-450 to an electrophilic gamma-ketoenal that reacts with nucleophilic groups on proteins to form covalent adducts. In addition, diastereomeric mintlactones are formed. Investigations with H2(18)O and 18O2 are indicative of a furan epoxide intermediate, or a precursor, in the formation of the gamma-ketoenal and mintlactones.
R(+)-pulegone impairs Ca²+ homeostasis and causes negative inotropism in mammalian myocardium
Eur J Pharmacol 2011 Dec 15;672(1-3):135-42.PMID:22004607DOI:10.1016/j.ejphar.2011.09.186.
The present study aimed to investigate the inotropic effects of R(+)-pulegone, a monoterpene found in plant species belonging to the genus Mentha, on the mammalian heart. In electrically stimulated guinea pig atria, R(+)-pulegone reduced the contractile force (~83%) and decreased the contraction time measured at 50% of the maximum force amplitude (CT(50)) from 45.8 ± 6.2 ms to 36.9 ± 6.2 ms, suggesting that R(+)-pulegone may have an effect on Ca(2+) homeostasis. Nifedipine (40 μM), taken as a positive control, showed a very similar profile. To explore the hypothesis that R(+)-pulegone is somehow affecting Ca(2+) handling, we determined concentration-response curves for both CaCl(2) and BAY K8644. R(+)-pulegone shifted these curves rightward. Using isolated mouse ventricular cardiomyocytes, we measured whole-cell L-type Ca(2+) current and observed an I(Ca,L) peak reduction of 13.7 ± 2.5% and 40.2 ± 2.9% after a 3-min perfusion with 0.11 and 1.1mM of R(+)-pulegone, respectively. In addition, the intracellular Ca(2+) transient was decreased (72.9%) by 3.2mM R(+)-pulegone, with no significant changes in [Ca(2+)](i) transient decay kinetics. Moreover, R(+)-pulegone at 1.1mM prolonged the action potential duration at 10, 50, and 90% of repolarisation. The lengthening of the action potential duration may be attributed to the substantial blockade of the outward K(+) currents caused by 1.1mM of R(+)-pulegone (90.5% at 60 mV). These findings suggest that R(+)-pulegone exerts its negative inotropic effect on mammalian heart mainly by decreasing the L-type Ca(2+) current and the global intracellular Ca(2+) transient.
Pharmacological activity of (R)-(+)-pulegone, a chemical constituent of essential oils
Z Naturforsch C J Biosci 2011 Jul-Aug;66(7-8):353-9.PMID:21950159DOI:10.1515/znc-2011-7-806.
(R)-(+)-Pulegone is a monoterpene found in essential oils from plants of the Labiatae family. This compound is a major constituent of Agastache formosanum oil. In this study, the effect of (R)-(+)-pulegone on the central nervous system was evaluated. (R)-(+)-Pulegone caused a significant decrease in ambulation and an increase in pentobarbital-induced sleeping time in mice, indicating a central depressant effect. (+)-Pulegone also significantly increased the latency of convulsions as assessed by the pentylenetetrazole (PTZ) method. The antinociceptive properties of this monoterpene were studied in chemical and thermal models of nociception. Chemical nociception induced in the first and second phase of the subplantar formalin test was significantly inhibited by (R)-(+)-pulegone and was not blocked by naloxone. Thermal nociception was also significantly inhibited while (R)-(+)-pulegone increased the reaction latency of the mice in the hot plate test. These results suggest that (R)-(+)-pulegone is a psychoactive compound and has the profile of an analgesic drug.
(R)-(+)-pulegone suppresses allergic and inflammation responses on 2,4-dinitrochlorobenzene-induced atopic dermatitis in mice model
J Dermatol Sci 2018 Sep;91(3):292-300.PMID:29933898DOI:10.1016/j.jdermsci.2018.06.002.
Background: (R)-(+)-pulegone (PLG), a biotransformation of monoterpene ketones, is one of essential oils of Labiatae family. Although PLG was reported to have anti-inflammatory and anti-histamine effects, the therapeutic effects of PLG on atopic dermatitis (AD) have not been reported yet. Objective: This study investigated the anti-AD effects and underlying mechanisms of PLG in AD-induced mice. Methods: BALB/c male mice were challenged with 2, 4-dinitrochlorobenzene (DNCB, 1%) to induce AD. After 4 days of rest, PLG (0.1, 1 and 10 μM) were topically applied to dorsal skin for 2 weeks with secondary elicitation using 0.5% DNCB. Histological changes were identified by H&E staining and mast cells were evaluated by toluidine blue staining. Pro-inflammatory cytokines and serum IgE levels were analyzed by ELISA. Inflammatory mediators were measured by western blotting assay. Results: Topical treatment with PLG significantly suppressed skin thickness and scratching behavior compared with control group. Expression of nerve growth factor was also decreased by PLG treatment. PLG administration decreased serum IgE levels and the number of mast cells in mice model of DNCB-induced AD. The levels of IL-4, IFN-γ, IL-6, TNF-α and IL-1β in dorsal skin of PLG-treated group were lower than those in the control group. PLG inhibited the phosphorylation of MAPKs, as well as IκBα degradation and NF-κB activation. Conclusions: PLG attenuated the symptoms of AD by suppressing cytokines production, the phosphorylation of MAPKs and the activation of NF-κB signaling. These data suggest that PLG may be an effective natural compound for the treatment of inflammatory skin diseases.
Pulegone: An Emerging Oxygenated Cyclic Monoterpene Ketone Scaffold Delineating Synthesis, Chemical Reactivity, and Biological potential
Recent Adv Antiinfect Drug Discov 2023;18(1):16-28.PMID:36263486DOI:10.2174/2772434418666221018090507.
Pulegone ((R)-5-Methyl-2-(1-methylethylidine) cyclohexanone) is a pharmacologically active, natural monoterpene ketone obtained from leaves and flowering tops of the mint family (Lamiaceae). The aim is to comprise the physicochemical and biological aspects of pulegone. All significant databases were collected via electronic search using Pubmed, Scopus, Web of Science, and Science Direct and were compiled. This review presents the occurrence, chemistry, and modifications of pulegone structure and its effect on the biological system. Pulegone represents various pharmacological properties, i.e., antioxidant, antimicrobial, anti-feeding, antifungal, antiviral, and pesticide activities, and has a significant role as an abortifacient and emmenagogue. Thus, this present review concludes the knowledgeable erudition on pulegone that paves the way for further work.