Makisterone A
(Synonyms: 罗汉松甾酮A) 目录号 : GC44114
An ecdysteroid that acts as a molting hormone
Cas No.:20137-14-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Makisterone A is an ecdysteroid that drives molting in insects. It binds the heterodimeric ecdysone receptor with nanomolar affinity.
| Cas No. | 20137-14-8 | SDF | |
| 别名 | 罗汉松甾酮A | ||
| Canonical SMILES | CC(O)(C)[C@H](C)C[C@@H](O)[C@](C)(O)[C@@]1([H])CC[C@@]2(O)C3=CC([C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@@]21C)=O | ||
| 分子式 | C28H46O7 | 分子量 | 494.7 |
| 溶解度 | DMSO : 1 mg/mL (2.02 mM; Need ultrasonic and warming) | 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 | 2.0214 mL | 10.1071 mL | 20.2143 mL |
| 5 mM | 0.4043 mL | 2.0214 mL | 4.0429 mL |
| 10 mM | 0.2021 mL | 1.0107 mL | 2.0214 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。
Makisterone A attenuates experimental cholestasis by activating the farnesoid X receptor
Biochem Biophys Res Commun 2022 Oct 1;623:162-169.PMID:35921707DOI:10.1016/j.bbrc.2022.07.030.
Cholestasis is the accumulation of bile acids in the liver due to impaired bile formation, secretion, and excretion caused by infections, drugs, metabolic or genetic diseases. Ursodeoxycholic acid is the only drug approved by the Food and Drug Administration for the treatment of primary biliary cholangitis, but nearly 40% of patients do not adequately respond to this drug and 5-10% show intolerance. The farnesoid X receptor (FXR) plays a key role in bile acid metabolism. Here, by using HERB, a high-throughput experimental and reference-oriented database of herbal medicines, and molecular docking, we identified Makisterone A (MakA) as a compound that could target FXR. We showed that MakA enhanced FXR activity in liver cells and expression levels of FXR target genes in vitro. Importantly, MakA intervention alleviated cholestatic liver injury and dysregulation of hepatic bile acid metabolism induced by α-naphthylisothiocyanate and, 5-diethoxycarbonyl-1,4-dihydrocollidine in mice. The ability of MakA to improve liver injury in a mouse model suggests that this drug may be used for clinical treatment of cholestasis.
Evidence for the presence of Makisterone A in Drosophila larvae and the secretion of 20-deoxymakisterone A by the ring gland
Proc Natl Acad Sci U S A 1984 Sep;81(18):5643-7.PMID:16593512DOI:10.1073/pnas.81.18.5643.
Ring glands or brain-ring gland complexes from third-instar Drosophila melanogaster larvae secreted ecdysone [(22R)-2beta,3beta,14alpha,22,25-pentahydroxy-5beta-cholest-7-en-6-one] and two less polar ecdysteroids (LP1 and LP2) in vitro. Radioimmunoassay with different antisera indicated that LP1 and LP2 are side-chain-modified analogues of ecdysone. In high-performance liquid chromatography, the retention time of LP2 was equivalent to that of a precursor of Makisterone A [(20R,22R)-2beta,3beta,14alpha,20,22,25-hexahydroxy-24-methyl-5beta-cholest-7-en-6-one] secreted by Dysdercus fasciatus prothoracic glands in vitro. LP2 was metabolized in vitro by the fat body of Drosophila larvae to a product with the characteristics of Makisterone A when analyzed by gas chromatography/mass spectrometry (selected ion monitoring). Evidence was obtained for the presence of Makisterone A in Drosophila larvae. These data suggest that LP2 is 20-deoxymakisterone A (24-methylecdysone) and that Makisterone A could function as an additional moulting hormone in Drosophila, although 20-deoxymakisterone A production is apparently dependent on the sterol composition of the diet. LP1 has not been identified.
Makisterone A:a 28-carbon hexahydroxy molting hormone from the embryo of the milkweed bug
Science 1975 Nov 14;190(4215):681-2.PMID:1237931DOI:10.1126/science.1237931.
Makisterone A is the predominant ecdysone in the 96 +/- 4-hour-old embryo of the large milkweed bug and it is the first molting hormone with a C-24 alkyl substituent of the side chain to be isolated and identified from an insect. In addition, unknown compounds that may represent other C28 ecdysones were detected in very low concentrations. The milkweed bug could well possess a biosynthetic-metabolic pathway for C28 molting hormones instead of or in addition to known pathways for the C27 ecdysones.
An ecdysone receptor from the pentatomomorphan, Nezara viridula, shows similar affinities for moulting hormones Makisterone A and 20-hydroxyecdysone
Insect Biochem Mol Biol 2011 Feb;41(2):77-89.PMID:21035548DOI:10.1016/j.ibmb.2010.10.002.
It has been suggested that Pentatomomorpha utilise the C(28) ecdysteroid, Makisterone A (MakA), as the major moulting hormone rather than the more common C(27) hormone, 20-hydroxyecdsyone (20E). The present study is the first to examine this postulate at the level of the ecdysone receptor protein, a heterodimer of nuclear receptors EcR and USP. cDNAs encoding two alternatively spliced isoforms of EcR and a single USP were isolated from a high-quality cDNA library prepared from a representative pentatomomorphan, Nezara viridula (Nv). NvEcR and NvUSP were found to group phylogenetically with heteropteran and other insect EcRs and USP/RXRs, respectively. Sequence comparison and phylogenetic analysis of these proteins found them to be distinct from those belonging to other hemipteran ecdysone receptors characterised to date. Co-expression of the His(6)-tagged ligand binding regions (LBRs) of the two NvEcR variants with the FLAG-tagged LBR of NvUSP was achieved in insect cells employing appropriately constructed baculoviruses. The corresponding heterodimers, designated NvE10 and NvE11, were purified by affinity chromatography utilising the His(6) tags on their NvEcR subunits. The heterodimers displayed nanomolar affinity for [(3)H]ponasterone A (K(d) = 6.8-7.5 nM), characteristic of ecdysone receptors. MakA has a similar affinity to 20E for both NvE10 and NvE11, consistent with MakA being a major moulting hormone in N. viridula.
The ecdysteroidome of Drosophila: influence of diet and development
Development 2015 Nov 1;142(21):3758-68.PMID:26395481DOI:10.1242/dev.124982.
Ecdysteroids are the hormones regulating development, physiology and fertility in arthropods, which synthesize them exclusively from dietary sterols. But how dietary sterol diversity influences the ecdysteroid profile, how animals ensure the production of desired hormones and whether there are functional differences between different ecdysteroids produced in vivo remains unknown. This is because currently there is no analytical technology for unbiased, comprehensive and quantitative assessment of the full complement of endogenous ecdysteroids. We developed a new LC-MS/MS method to screen the entire chemical space of ecdysteroid-related structures and to quantify known and newly discovered hormones and their catabolites. We quantified the ecdysteroidome in Drosophila melanogaster and investigated how the ecdysteroid profile varies with diet and development. We show that Drosophila can produce four different classes of ecdysteroids, which are obligatorily derived from four types of dietary sterol precursors. Drosophila makes Makisterone A from plant sterols and epi-makisterone A from ergosterol, the major yeast sterol. However, they prefer to selectively utilize scarce ergosterol precursors to make a novel hormone 24,28-dehydromakisterone A and trace cholesterol to synthesize 20-hydroxyecdysone. Interestingly, epi-makisterone A supports only larval development, whereas all other ecdysteroids allow full adult development. We suggest that evolutionary pressure against producing epi-C-24 ecdysteroids might explain selective utilization of ergosterol precursors and the puzzling preference for cholesterol.