Petromyzonol
(Synonyms: 5ALPHA-胆烷-3ALPHA,7ALPHA,12ALPHA,24-四醇) 目录号 : GC44604
Synthetic intermediate
Cas No.:28979-29-5
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Petromyzonol is a tetrahydroxy stearol which serves as the primary spawning pheromone in adult sea lamprey. It is produced in the bile of sea lamprey larvae from the bile acid precursor allocholic acid. While the adult sea lamprey is relatively insensitive to petromyzonol itself, the C-24 sulfate ester (petromyzonol sulfate) is a pheromone and a spawning chemoattractant which can be detected at very low concentrations by lamprey olfactory chemoreceptors. Petromyzonol, petromyzonol sulfate, and allocholic acid are all found in water samples from fresh water streams bearing larval lamprey populations.[1]
Reference:
[1]. Li, W., Sorensen, P.W., and Gallaher, D.D. The olfactory system of migratory adult sea lamprey (Petromyzon marinus) is specifically and acutely sensitive to unique bile acids released by conspecific larvae. Journal of General Physiology 105, 569-587 (1995).
| Cas No. | 28979-29-5 | SDF | |
| 别名 | 5ALPHA-胆烷-3ALPHA,7ALPHA,12ALPHA,24-四醇 | ||
| 化学名 | 3α,7α,12α,24-tetrahydroxy-5α-cholane | ||
| Canonical SMILES | C[C@H](CCCO)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@@]21C | ||
| 分子式 | C24H42O4 | 分子量 | 394.6 |
| 溶解度 | 1mg/mL in DMSO, 2mg/mL in DMF, 2mg/mL in Ethanol | 储存条件 | Store at RT |
| 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.5342 mL | 12.6711 mL | 25.3421 mL |
| 5 mM | 0.5068 mL | 2.5342 mL | 5.0684 mL |
| 10 mM | 0.2534 mL | 1.2671 mL | 2.5342 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。
Petromyzonol sulfate and its derivatives: the chemoattractants of the sea lamprey
Bioessays 2005 Feb;27(2):222-8.PMID:15666352DOI:10.1002/bies.20155.
Petromyzonol sulfate (PZS) and 3 keto-PZS are bile alocohol derivatives that serve as chemoattractants during the life cycle of sea lamprey (Petromyzon marinus). The sulfonate moiety is crucial perhaps conferring the required solubility for the pheromone that is released into the streams and for the specificity to bind to its receptor. During the life cycle of lamprey, larvae produce copious amounts of 5 alpha-cholan-PZS, and trace amounts of allocholic acid (ACA), which attracts adults to the same breeding ground. Later the spermeating males produce 3keto-PZS, and trace amounts of 3-keto-ACA, which attracts the ovulating females, signaling both its reproductive status and its nesting location for successful reproduction. In both stages, a mixture of components serves as pheromone plume, similar to insects. The receptors for the migratory and the reproductive pheromones need to be molecularly cloned and characterized in order to understand the molecular biology of olfaction in the sea lamprey.
Biologically relevant concentrations of Petromyzonol sulfate, a component of the sea lamprey migratory pheromone, measured in stream water
J Chem Ecol 2005 Sep;31(9):2205-10.PMID:16132221DOI:10.1007/s10886-005-6745-4.
Adult sea lampreys locate spawning streams in the Great Lakes by using a migratory pheromone that is released by stream-resident larval conspecifics. Behavioral, electrophysiological, and biochemical analyses of larval release water have suggested that this pheromone is composed of several components, one of which is Petromyzonol sulfate (PS), a known lamprey-specific bile acid. Its precursor, allocholic acid (ACA), has also been implicated. In this study, we employed high-performance liquid chromatography and mass spectrometry to look for both bile acids in various stream waters, thereby testing whether they might have a role in natural pheromone function. Although PS was measured at picomolar concentrations in streams known to contain larval lampreys and attract migratory adults, ACA was not. Neither compound was measured in streams lacking larvae. This finding indicates that PS is a component of the natural pheromone, and it suggests that ACA has little relevance.
Pheromones of the male sea lamprey, Petromyzon marinus L.: structural studies on a new compound, 3-keto allocholic acid, and 3-keto Petromyzonol sulfate
Steroids 2003 Mar;68(3):297-304.PMID:12628693DOI:10.1016/s0039-128x(02)00178-2.
This study reports the results of chemical and chromatographic studies which establish the presence of 3-keto allocholic acid (3kACA) in water extracts from spermiating male sea lamprey, Petromyzon marinus. This is the second compound to be isolated and identified from these extracts. The first was 3-keto Petromyzonol sulfate (3kPZS), which was shown to act as strong pheromonal attractant for ovulated females. Some new characterization data on 3kPZS (utilizing an only recently available synthetic preparation of the compound) is also included. The possibility that a mixture of 3kACA and 3kPZS might be a more potent pheromonal attractant than either compound alone is discussed.
Isolation, partial purification, and characterization of a novel Petromyzonol sulfotransferase from Petromyzon marinus (lamprey) larval liver
J Lipid Res 2004 Mar;45(3):486-95.PMID:14657197DOI:10.1194/jlr.M300346-JLR200.
We have isolated, partially purified, and characterized the 5 alpha-petromyzonol (5 alpha-PZ), (5 alpha-cholan- 3 alpha, 7 alpha, 12 alpha, 24-tetrahydroxy-) sulfotransferase (PZ-SULT) from larval lamprey liver. Crude liver extracts exhibited a PZ-SULT activity of 0.9120 pmol/min/mg in juvenile and 12.62 pmol/min/mg in larvae. Using crude larval liver extracts and various 5 beta-cholan substrates and allocholic acid there was negligible activity, however, with 5 alpha-PZ and 3-keto-5 alpha-PZ the SULT activity was 231.5 pmol/min/mg and 180.8 pmol/min/mg respectively. This established that the sulfotransferase of lamprey larval liver extracts prefers (5 alpha) substrates and it is selective for hydroxyl at C-24. PZ-SULT was purified through various chromatography procedures. Partially purified PZ-SULT exhibited a pH optimum of 8.0, a temperature optimum of 22 degrees C, and activity was linear for 1h. PZ-SULT exhibited a K(m) of 2.5 microM for PAPS and a K(m) of 8 microM for PZ. The affinity purified peak PZ-SULT exhibited a specific activity of 2,038 pmol/min/mg. The peak protein upon SDS-PAGE, correlated to an Mw 47 kDa. Photoaffinity labeling with PAP(35)S, specifically crosslinked the 47 kDa protein, further confirming the identity of PZ-SULT. Partial amino acid sequencing of the putative 47 kDa PZ-SULT protein yielded a peptide sequence (M)SISQAVDAAFXEI, which possessed an overall (approximately 35-40%) homology with mammalian SULT2B1a.
A sensitive analytical method for quantifying Petromyzonol sulfate in water as a potential tool for population monitoring of the southern pouched lamprey, Geotria australis, in New Zealand streams
J Chem Ecol 2012 Feb;38(2):135-44.PMID:22327275DOI:10.1007/s10886-012-0069-y.
The migratory southern pouched lamprey, Geotria australis, is a culturally important fish native to New Zealand. Anecdotal evidence suggests that populations of G. australis have declined from historic levels, and presently, this species is rare in many New Zealand rivers and streams. Migratory sea lamprey (Petromyzon marinus) use a pheromone mixture to locate suitable spawning sites. This mixture is comprised of three steroids: Petromyzonol sulfate (PS), petromyzonamine disulfate (PADS), and petromyzosterol disulfate (PSDS). We examined the migratory pheromone mixture released by G. australis ammocetes and found that they excrete predominantly PS. PADS has been detected on some occasions in low concentrations, and PSDS either is not released, or is released in extremely low concentrations. By using a recently developed sensitive mass spectrometry method, we compared passive sampling techniques against more traditional active water sampling as methods for estimating lamprey populations in local streams. Passive sampling provided quantitative data for PS from all sites surveyed, with uptake rates of 0.3 to 45.7 pg/day observed. Conversely, active sampling returned only one positive result out of 19 samples, and with a method detection limit of 2.5 × 10(-14) M, this suggests that concentrations of PS in these streams are either extremely low or variable. The combination of passive sampling and triple quadrupole mass spectrometry is a promising tool for monitoring of G. australis in New Zealand streams.