Juvenile Hormone III
(Synonyms: 保幼激素3,trans-trans-10,11-Epoxyfarnesenic Acid methyl ester) 目录号 : GC43934An insect hormone
Cas No.:24198-95-6
Sample solution is provided at 25 µL, 10mM.
Quality Control & SDS
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- Purity: >95.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Juvenile hormone III is an acyclic sesquiterpenoid that regulates diverse processes in insects, including adult transition of larvae and oogenesis in adult females. [1][2] It activates the juvenile hormone receptor, known as methoprene-tolerant, with a Kd value of 2.9 nM.[2] Juvenile hormone III can be synthesized from farnesoic acid by two alternative pathways, one through methyl farnesoate and the other through juvenile hormone acid III.[3][4]
Reference:
[1]. Tillman, J.A., Seybold, S.J., Jurenka, R.A., et al. Insect pheromones--an overview of biosynthesis and endocrine regulation. Insect Biochemistry and Molecular Biology 29(6), 481-514 (1999).
[2]. Charles, J.P., Iwema, T., Epa, V.C., et al. Ligand-binding properties of a juvenile hormone receptor, methoprene-tolerant. Proceedings of the National Academy of Sciences of the United States of America 108(52), 21128-21133 (2011).
[3]. Defelipe, L.A., Dolghih, E., Roitberg, A.E., et al. Juvenile hormone synthesis: "Esterify then epoxidize" or "epoxidize then esterify"? Insights from the structural characterization of juvenile hormone acid methyltransferase. Insect Biochemistry and Molecular Biology 41(4), 228-235 (2011).
[4]. Navare, A.T., Mayoral, J.G., Nouzova, M., et al. Rapid direct analysis in real time (DART) mass spectrometric detection of juvenile hormone III and its terpene precursors. Analytical and Bioanalytical Chemistry 398(7-8), 3005-3013 (2010).
| Cas No. | 24198-95-6 | SDF | |
| 别名 | 保幼激素3,trans-trans-10,11-Epoxyfarnesenic Acid methyl ester | ||
| 化学名 | (2E,6E)-9-(3,3-dimethyl-2-oxiranyl)-3,7-dimethyl-2,6-nonadienoic acid, methyl ester | ||
| Canonical SMILES | COC(/C=C(CC/C=C(C)/CCC1OC1(C)C)\C)=O | ||
| 分子式 | C16H26O3 | 分子量 | 266.4 |
| 溶解度 | 12mg/mL in ethanol, 10mg/ml in DMSO, 14mg/mL in DMF | 储存条件 | Store at -20°C, protect from light |
| 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 | 3.7538 mL | 18.7688 mL | 37.5375 mL |
| 5 mM | 0.7508 mL | 3.7538 mL | 7.5075 mL |
| 10 mM | 0.3754 mL | 1.8769 mL | 3.7538 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。
A new sesquiterpenoid Juvenile Hormone III from the stems of Cananga latifolia
J Asian Nat Prod Res 2022 Dec;24(12):1185-1191.PMID:35130808DOI:10.1080/10286020.2022.2030316.
A new Juvenile Hormone III, canangalia I (1), along with six known Juvenile Hormone III analogues (2-7), was isolated from the methanolic extract of Cananga latifolia stems. All structures were elucidated using spectroscopic data and compared with data from previous literature. Canangalia I (1) was found to be cytotoxic against human cervical adenocarcinoma (HeLa) cells with an IC50 value of 35.00 ± 2.15 µg/ml after 72 h, but was not toxic to Vero cells.
Juvenile Hormone III R Stereoisomer Is Specifically Synthesized by Honeybees ( Apis mellifera ligustica) and Shows a Higher Biological Activity in Regulating Their Social Behavior
J Agric Food Chem 2022 May 25;70(20):6097-6107.PMID:35544752DOI:10.1021/acs.jafc.2c00762.
The juvenile hormone (JH) plays a key role in the development of honeybee larvae and the alteration of adult behavior. Verification methods of types and stereoisomers of JHs in honeybees were established in this study. The regulatory modes of different stereoisomers of JH III on the social behaviors of honeybees were revealed by the disparity of interaction and RNA-seq. This result represented the first assessment of the effects of R-JH III and S-JH III in honeybee interactions; the former (367 times in total) was significantly higher than the latter (235 times in total); honeybees with high JH titers are always welcome in the colony because the effect of JH III on bees involves the sensing and signaling of hormones, and R-JH III is much more active than S-JH III in this regulation. Efficient R-JH III may be the insurance for bees to establish their social system advantages.
Juvenile Hormone III skipped bisepoxide is widespread in true bugs (Hemiptera: Heteroptera)
R Soc Open Sci 2021 Feb 3;8(2):202242.PMID:33972884DOI:10.1098/rsos.202242.
Juvenile hormone (JH) plays important roles in almost every aspect of insect development and reproduction. JHs are a group of acyclic sesquiterpenoids, and their farnesol backbone has been chemically modified to generate a homologous series of hormones in some insect lineages. JH III (methyl farnesoate, 10,11-epoxide) is the most common JH in insects, but Lepidoptera (butterflies and moths) and 'higher' Diptera (suborder: Brachycera; flies) have developed their own unique JHs. Although JH was first proposed in the hemipteran suborder Heteroptera (true bugs), the chemical identity of the heteropteran JH was only recently determined. Furthermore, recent studies revealed the presence of a novel JH, JH III skipped bisepoxide (JHSB3), in some heteropterans, but its taxonomic distribution remains largely unknown. In the present study, we investigated JHSB3 production in 31 heteropteran species, covering almost all heteropteran lineages, through ultra-performance liquid chromatography coupled with tandem mass spectrometry. We found that all of the focal species produced JHSB3, indicating that JHSB3 is widespread in heteropteran bugs and the evolutionary occurrence of JHSB3 ascends to the common ancestor of Heteroptera.
Juvenile Hormone III skipped bisepoxide, not its stereoisomers, as a juvenile hormone of the bean bug Riptortus pedestris
Gen Comp Endocrinol 2020 Apr 1;289:113394.PMID:31962126DOI:10.1016/j.ygcen.2020.113394.
Juvenile hormone (JH) plays a pivotal role in many aspects of insect physiology. Although its presence was first reported in a blood-sucking bug belonging to the suborder Heteroptera (true bugs), JH species in the group has long been controversial. Although some recent studies proposed a putative JH molecular species in several Heteropteran species, it is not conclusive because physicochemical analyses were insufficient in most cases. Here, we studied this issue with an ultraperformance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS) equipped with C18 and chiral columns in the bean bug Riptortus pedestris (Heteroptera, Alydidae), in which the JH species has long been controversial. Although a recent study describes JHSB3 as the major JH of this species, that finding was not conclusive because its chirality has not been clarified. In the present study, we detected methyl (2R,3S,10R)-2,3;10,11-bisepoxyfarnesoate, commonly named Juvenile Hormone III skipped bisepoxide (JHSB3), in the culture media of the corpora cardiaca-corpus allatum (CC-CA) complex and in the hemolymph of this species by a chiral ultraperformance liquid chromatography- tandem mass spectrometer (UPLC-MS/MS). Other JHSB3 stereoisomers were not detected. Topical application of JHSB3 effectively averted diapause. These results indicate that JHSB3 is the major JH of R. pedestris. The present study further revealed that JHSB3 and its (2R,3S,10S) isomer are more potent than (2S,3R,10R) and (2S,3R,10S) isomers, which suggests that there is a significance to the configuration of the 2,3-epoxide moiety in JH action. We further found a supplemental significance to the configuration of the 10-position.
Juvenile Hormone III but Not 20-Hydroxyecdysone Regulates the Embryonic Diapause of Aedes albopictus
Front Physiol 2019 Oct 25;10:1352.PMID:31708801DOI:10.3389/fphys.2019.01352.
Diapause is an alternative developmental trajectory allowing insects to enter dormancy and persist through predictable periods of seasonally unfavorable conditions. This crucial ecological adaptation defines the geographic and seasonal abundance of many insect pollinators, pests, and vectors. Understanding the hormonal changes by which insects coordinate the perception of external, diapause-inducing cues with the physiological mechanisms that lead to developmental arrest is a long-standing goal in biology. The hormonal regulation of diapause tends to vary by the life stage at which development arrest occurs; for example, diapause is typically regulated by ecdysteroids in larvae and pupae, and by juvenile hormones in adults. However, little is known about the hormonal control of embryonic diapause, particularly in Diptera. To address this fundamental gap, we directly measured 20-hydroxyecdysone (20HE) (via LC-MS/MS) and Juvenile Hormone III (JH3) (via GC-MS) in diapause and non-diapause eggs of the Asian tiger mosquito, Aedes albopictus. While 20HE abundance did not differ, diapause eggs had lower JH3 abundance than non-diapause eggs. These results are corroborated by transcriptional and manipulative evidence suggesting that reduced JH3 regulates diapause in this medically important mosquito.