Primin
(Synonyms: 樱草素) 目录号 : GC60302
A benzoquinone with diverse biological activities
Cas No.:15121-94-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Primin is a benzoquinone that has been found in P. obconica and has diverse biological activities.1,2,3,4 It selectively inhibits COX-2 over COX-1 (IC50s = 0.09 and 5.14 ?M, respectively) and induces the production of adrenochrome from epinephrine, a marker of pro-oxidant activity, in a cell-free assay when used at a concentration of 8.81 ?M.1 Primin is active against T. brucei rhodesiense and L. donovani (IC50s = 0.144 and 0.711 ?M, respectively), as well as S. aureus (IC50 = 8.94 ?M).2,3 In vivo, primin induces contact sensitization in guinea pigs.4
1.Landa, P., Kutil, Z., Temml, V., et al.Redox and non-redox mechanism of in vitro cyclooxygenase inhibition by natural quinonesPlanta Med.78(4)326-333(2011) 2.Tasdemir, D., Brun, R., Yardley, V., et al.Antituberculotic and antiprotozoal activities of primin, a natural benzoquinone: In vitro and in vivo studiesChem. Biodivers.3(11)1230-1237(2006) 3.Viegas, F.P.D., Espuri, P.F., Oliver, J.C., et al.Leishmanicidal and antimicrobial activity of primin and primin-containing extracts from Miconia willdenowiiFitoterapia138104297(2019) 4.Schulz, K.H., Garbe, I., Hausen, B.M., et al.The sensitizing capacity of naturally occurring quinones. Experimental studies in guinea pigs. II. BenzoquinonesArch. Dermatol. Res.264(3)275-286(1979)
| Cas No. | 15121-94-5 | SDF | |
| 别名 | 樱草素 | ||
| Canonical SMILES | O=C1C(OC)=CC(C=C1CCCCC)=O | ||
| 分子式 | C12H16O3 | 分子量 | 208.25 |
| 溶解度 | 储存条件 | ||
| 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 | 4.8019 mL | 24.0096 mL | 48.0192 mL |
| 5 mM | 0.9604 mL | 4.8019 mL | 9.6038 mL |
| 10 mM | 0.4802 mL | 2.401 mL | 4.8019 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。
Primin sensitization in north-eastern Italy: a temporal trend from 1996 to 2012
Contact Dermatitis 2015 Aug;73(2):108-12.PMID:25799880DOI:10.1111/cod.12385.
Background: Primin is the main contact allergen found in the ornamental plant Primula obconica Hance. Objective: To analyse the temporal trend of sensitivity to Primin in north-eastern Italy and to evaluate the associations with occupations in our geographical area. Methodology: From 1996 to 2012, 24 052 consecutive patients with suspected allergic contact dermatitis were patch tested in north-eastern Italy. Individual characteristics were collected through a standardized questionnaire in eight departments of dermatology or occupational medicine. Results: The overall prevalence of Primin sensitization was 1.9%; the prevalence was significantly higher in women (2.6%) than in men (0.5%). The Pordenone area had the higher prevalence of sensitization, which reached 6% in 1999-2001. We found a significant association between Primin sensitization and household workers [odds ratio (OR) 2.3; 95% confidence interval (CI): 1.61-3.35], retired people (OR 1.8; 95%CI: 1.22-2.81), woodworkers (OR 2.1; 95%CI: 1.10-6.18), and chemical industry workers (OR 2.9; 95%CI: 1.05-8.29). Conclusion: Our study showed that contact allergy to Primin is still relevant in north-eastern Italy. The frequency of sensitization is decreasing, but for retired and household workers it is still >4%. Our results suggest the need to promote the use of primin-free P. obconica in Italy.
Primin in the European standard patch test series for 20 years
Contact Dermatitis 2007 Jun;56(6):344-6.PMID:17577376DOI:10.1111/j.1600-0536.2007.01122.x.
Primin was included in the European standard series (ESS) in 1984. In 2000, a primin-free variant of Primula obconica, the main source of contact allergy to Primin, was introduced in the market. The aim of this study was to analyse the trends of Primin allergy in 13 986 consecutively patch-tested eczema patients over a 20-year period from 1985 to 2004. 151 patients gave a positive patch test to Primin. The majority were women, in two-third of patients the patch test was relevant and most presented with hand eczema. Only few of the cases (4.7%) were occupational. A significant decline of contact allergy to Primin was seen (P < 0.001) over the years affecting all age groups. The frequency was 0.5% during 2000-2004. Contact allergy has been rare since 2000. The low frequency of positive patch test to Primin does not support inclusion in the ESS in our region.
Cytotoxic mechanisms of Primin, a natural quinone isolated from Eugenia hiemalis, on hematological cancer cell lines
Anticancer Drugs 2020 Aug;31(7):709-717.PMID:32639281DOI:10.1097/CAD.0000000000000937.
Considering the high morbidity and mortality rates associated with hematological malignancies and the frequent development of drug resistance by these diseases, the search for new cytotoxic agents is an urgent necessity. The new compounds should present higher efficiency and specificity in inducing tumor cell death, be easily administered and have little or negligible adverse effects. Quinones have been reported in the literature by their several pharmacological properties, including antitumor activity, thus, the aim of this study was to investigate the cytotoxic effect of Primin, a natural quinone, on hematological malignancies cell lines. Primin was highly cytotoxic against the three cell lines included in this study (K562, Jurkat and MM.1S) in a concentration- and time-dependent manner, as demonstrated by the MTT method. The compound triggered an apoptotic-like cell death, as observed by ethidium bromide/acridine orange staining, DNA fragmentation and phosphatidylserine exposure after labeling with Annexin V. Both intrinsic and extrinsic apoptosis are involved in cell death induced by Primin, as well as the modulation of cell proliferation marker KI-67. The activation of intrinsic apoptosis appears to be related to a decreased Bcl-2 expression and increased Bax expression. While the increase in FasR expression signals activate extrinsic apoptosis. The results suggest that Primin is a promising natural molecule that could be used in hematological malignancies therapy or as prototypes for the development of new chemotherapics.
Leishmanicidal and antimicrobial activity of Primin and primin-containing extracts from Miconia willdenowii
Fitoterapia 2019 Oct;138:104297.PMID:31404617DOI:10.1016/j.fitote.2019.104297.
As a part of an ongoing bioprospective project, searching for potential medicinal plants from the Brazilian Atlantic Forest, Miconia willdenowii was selected for its potential leishmanicidal and antimicrobial activities. The crude ethanolic extract of M. willdenowii showed an inhibition of 99.7% of the promastigote forms of Leishmania amazonensis at the concentration of 80 μg/mL. Further investigation of its antimicrobial activity against pathogenic fungi and Gram positive and negative bacteria, revealed a significant antimicrobial activity. A bioguided study with its liquid-liquid partition fractions revealed the hexane fraction (Hex) as the most active against Leishmania, inhibiting 99.2% and 46.9% of the protozoan at concentrations of 40 and 20 μg/mL, respectively. Hex also showed significant antimicrobial activity against Staphylococcus aureus and Candida krusei with IC50 of 15.6 and 62.5 μg/mL, respectively. Purification of Hex led to the isolation of 2-methoxy-6-pentyl-benzoquinone (1, also known as Primin) as the active metabolite, probably responsible for the observed antimicrobial and anti-leishmania effects. Primin (1) disclosed leishmanicidal activity (IC50 = 1.25 μM), showing higher potency than the standard drug amphotericin B (IC50 = 5.08 μM), with additional antifungal effects against all tested fungi species. Compound 1 also showed significant activity against S. aureus (IC50 = 8.94 μM), showing a comparable potency with the reference drug chloramphenicol (IC50 = 6.19 μM), but with a potential cytotoxicity towards peripheral human blood mononuclear cells (CC50 = 255.15 μM). Here in, the antimicrobial and anti-L. amazonensis effects of M. willdenowii are reported for the first time, as well as Primin (1) as its probable bioactive metabolite.
Antituberculotic and antiprotozoal activities of Primin, a natural benzoquinone: in vitro and in vivo studies
Chem Biodivers 2006 Nov;3(11):1230-7.PMID:17193236DOI:10.1002/cbdv.200690124.
Primin (=2-methoxy-6-pentylcyclohexa-2,5-diene-1,4-dione), a natural benzoquinone synthesized in our laboratory, was investigated for its in vitro antiprotozoal, antimycobacterial, and cytotoxic potential. Primin showed very potent activity against Trypanosoma brucei rhodesiense (IC50 0.144 microM) and Leishmania donovani (IC50 0.711 microM), and revealed low cytotoxicity (IC50 15.4 microM) on mammalian cells. Only moderate inhibitory activity was observed against Mycobacterium tuberculosis, Trypanosoma cruzi, and Plasmodium falciparum. When tested for in vivo efficacy in a Trypanosoma b. brucei rodent model, Primin failed to cure the infection at 20 mg/kg given intraperitoneally. Primin was too toxic in vivo at a higher concentration (30 mg/kg, injected i.p. route) in mice infected with L. donovani. Taken together, Primin can serve as a lead compound for the rational design of more potent and less toxic antiprotozoal agents.