Precocene II
(Synonyms: 早熟素Ⅱ) 目录号 : GC47969A chromene with anti-juvenile hormone activity
Cas No.:644-06-4
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
Precocene II is a chromene that has been found in A. houstonianum and has anti-juvenile hormone activity.1,2,3 It inhibits juvenile hormone biosynthesis in isolated spontaneously active cockroach (P. americana) corpora allata when used at concentrations of 1 mM or higher.1 Precocene II (8 μg/cm2 coating in Petri dish) inhibits development of the corpus allatum in newly eclosed female milkweed bugs and causes allatal regression when applied 120 hours post-eclosion in normally developing females.2 It induces precocious metamorphosis in milkweed bug second-stage nymphs when applied as a coating to Petri dishes at concentrations of 0.4 and 0.7 μg/cm2.3 Precocene II inhibits ovarian development in various insects, including milkweed bugs, cotton stainers, apple maggots, and Mexican bean beetles. Precocene II also inhibits production of the trichothecene mycotoxin 3-acetyldeoxy nivalenol in F. graminearum (IC50 = 1.2 μM) without inhibiting fungal growth.4
1.Pratt, G.E., and Bowers, W.S.Precocene II inhibits juvenile hormone biosynthesis by cockroach corpora allata in vitroNature265(5594)548-550(1977) 2.Bowers, W.S., and Martinez-Pardo, R.Antiallatotropins: Inhibition of corpus allatum developmentScience197(4311)1369-1371(1977) 3.Bowers, W.S., Ohta, T., Cleere, J.S., et al.Discovery of insect anti-juvenile hormones in plantsScience193(4253)542-547(1976) 4.Sakuda, S.Mycotoxin production inhibitors from natural productsMycotoxins60(2)79-86(2010)
| Cas No. | 644-06-4 | SDF | |
| 别名 | 早熟素Ⅱ | ||
| Canonical SMILES | CC1(C)C=CC2=CC(OC)=C(OC)C=C2O1 | ||
| 分子式 | C13H16O3 | 分子量 | 220.3 |
| 溶解度 | Chloroform: soluble,Methanol: soluble | 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 | 4.5393 mL | 22.6963 mL | 45.3926 mL |
| 5 mM | 0.9079 mL | 4.5393 mL | 9.0785 mL |
| 10 mM | 0.4539 mL | 2.2696 mL | 4.5393 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。
Precocene II, a Trichothecene Production Inhibitor, Binds to Voltage-Dependent Anion Channel and Increases the Superoxide Level in Mitochondria of Fusarium graminearum
PLoS One 2015 Aug 6;10(8):e0135031.PMID:26248339DOI:10.1371/journal.pone.0135031.
Precocene II, a constituent of essential oils, shows antijuvenile hormone activity in insects and inhibits trichothecene production in fungi. We investigated the molecular mechanism by which Precocene II inhibits trichothecene production in Fusarium graminearum, the main causal agent of Fusarium head blight and trichothecene contamination in grains. Voltage-dependent anion channel (VDAC), a mitochondrial outer membrane protein, was identified as the precocene II-binding protein by an affinity magnetic bead method. Precocene II increased the superoxide level in mitochondria as well as the amount of oxidized mitochondrial proteins. Ascorbic acid, glutathione, and α-tocopherol promoted trichothecene production by the fungus. These antioxidants compensated for the inhibitory activity of Precocene II on trichothecene production. These results suggest that the binding of Precocene II to VDAC may cause high superoxide levels in mitochondria, which leads to stopping of trichothecene production.
Precocene II nephrotoxicity in the rat
Toxicol Lett 1982 Jul;12(2-3):95-100.PMID:7112615DOI:10.1016/0378-4274(82)90170-9.
The effects of Precocene II (6,7-dimethoxy-2,2-dimethylchromene) on the kidney were examined histopathologically. Marked changes were observed in the proximal convoluted tubules, collecting tubules, and glomeruli. These changes included congestion of blood in the capillaries of the glomeruli, tubular cell degeneration, and tubular cell regeneration. In addition, blood urea nitrogen levels were elevated in precocene II-treated animals. The results indicate that Precocene II is nephrotoxic in the male Sprague-Dawley rat.
Effect of Precocene II on fatty acid metabolism in the pea aphid, Acyrthosiphon pisum, under cold stress
J Insect Physiol 2005 Apr;51(4):411-6.PMID:15890184DOI:10.1016/j.jinsphys.2005.02.006.
Pea aphids, Acyrthosiphon pisum (Harris), reared at 10 degrees C contain higher levels of fatty acids than those reared at 25 degrees C. This is primarily the result of an accumulation of triacylglycerols containing myristic acid. When aphids reared at 25 degrees C were transferred to 10 degrees C there was a gradual increase in triacylglycerol content that reached a maximum at 16 days post-transfer. Treatment of aphids with Precocene II prior to transfer to 10 degrees C blocked the accumulation of fatty acids including myristic acid. A single application of 2 microg Precocene II/aphid or two applications of 0.5 microg Precocene II/ aphid administered on consecutive days resulted in aphids moved to 10 degrees C maintaining the same fatty acid profile as aphids maintained at 25 degrees C. Aphids that were treated with Precocene II and maintained at 25 degrees C did not show changes in fatty acid profiles. Rearing aphids at 10 degrees C resulted in lower rates of reproduction and lower total numbers of progeny with longer longevity. Treatment with Precocene II significantly decreased the total number of progeny produced at both temperatures. Precocene II did not reduce life span of aphids reared at 25 degrees C, however, the life span of treated aphids reared at 10 degrees C was decreased. The mechanism by which Precocene II prevents the accumulation of myristic acid in aphids reared at 10 degrees C remains to be determined.
The effects of Precocene II on reproduction and development of triatomine bugs (Reduviidae: Triatominae)
Am J Trop Med Hyg 1982 Mar;31(2):416-20.PMID:7041667DOI:10.4269/ajtmh.1982.31.416.
Precocene II is a botanically derived chemical that inhibits the production of juvenile hormone (JH) in insects. The effects of this anti-JH compound on molting and growth by Rhodnius prolixus and Triatoma dimidiata and reproduction in R. prolixus were tested and the efficacy of Precocene II as a fumigant was assessed. Precocene II induced precocious metamorphosis in both species when applied by either contact exposure or fumigation, and this effect could be prevented by juvenile hormone replacement therapy. The dosage effective in inducing precocious metamorphosis in T. dimidiata was similar to the EC50 previously reported for R. prolixus. The morphology of precocious adultoid T. dimidiata of different instars was similar to Rhodnius adultoids of corresponding instars. However, T. dimidiata was more sensitive than Rhodnius to the molt-inhibiting effects of Precocene II. Rhodnius nymphs were fully susceptible to the anti-JH action of precocene when exposed for 24 hours one week before feeding. Precocene II was highly toxic to adult female Rhodnius and treatment of newly emerged females prevented oogenesis.
Alteration of precocene II-induced hepatotoxicity by modulation of hepatic glutathione levels
Chem Biol Interact 1989;71(2-3):187-99.PMID:2598296DOI:10.1016/0009-2797(89)90034-3.
Precocene II (6,7-dimethoxy-2,2-dimethyl-2H-benzo[b]pyran), an insect growth regulator that is structurally related to several naturally occurring carcinogenic and non-carcinogenic alkenylbenzenes, is genotoxic and produces hepatic centrolobular necrosis in rats. This investigation was conducted to evaluate the effects of modulation of hepatic glutathione levels on the toxicity of Precocene II. Administration of a toxic dose of Precocene II (175 mg/kg) to male Sprague-Dawley rats rapidly depleted hepatic GSH, produced histopathological changes in the liver, and induced increases in serum aminotransferase activity. Concurrent administration of the cysteine pro-drug L-2-oxothiazolidine-4-carboxylic acid (OTC) prevented these toxic effects of Precocene II. In contrast, pretreatment of rats with DL-buthionine-SR-sulfoximine (BSO), an inhibitor of glutathione synthesis, potentiated the toxicity of an otherwise non-toxic dose of Precocene II (100 mg/kg). These results indicate that glutathione is important for protection from precocene II-induced hepatotoxicity.