Chimonanthine
(Synonyms: 蠟梅鹼,(-)-Chimonanthine) 目录号 : GC35675
Chimonanthine 是腊梅中的生物碱，抑制酪氨酸酶及酪氨酸酶相关蛋白 1 mRNA 的表达，抑制黑色素的形成。
Cas No.:5545-89-1
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
Chimonanthine is an alkaloid of Chimonanthus praecox, inhibits tyrosinase and tyrosine-related protein-1 mRNA expression, amd inhibits melanogenesis[1].
[1]. Morikawa T, et al. Dimeric pyrrolidinoindoline-type alkaloids with melanogenesis inhibitory activity in flower buds of Chimonanthus praecox. J Nat Med. 2014 Jul;68(3):539-49.
| Cas No. | 5545-89-1 | SDF | |
| 别名 | 蠟梅鹼,(-)-Chimonanthine | ||
| Canonical SMILES | CN1[C@@]2([H])[C@@](C3=CC=CC=C3N2)([C@]45C6=CC=CC=C6N[C@@]4([H])N(C)CC5)CC1 | ||
| 分子式 | C22H26N4 | 分子量 | 346.47 |
| 溶解度 | Soluble in DMSO | 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。 |
||
| 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 | 2.8863 mL | 14.4313 mL | 28.8625 mL |
| 5 mM | 0.5773 mL | 2.8863 mL | 5.7725 mL |
| 10 mM | 0.2886 mL | 1.4431 mL | 2.8863 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。
Total Synthesis of (+)-Chimonanthine, (+)-Folicanthine, and (-)-Calycanthine
J Org Chem 2015 Oct 16;80(20):10309-16.PMID:26402317DOI:10.1021/acs.joc.5b01907.
Facile, straightforward, and asymmetric total syntheses of (+)-chimonanthine (1), (+)-folicanthine (2), and (-)-calycanthine (3) were accomplished in four to five steps from commercially available tryptamine. The synthesis features copper-mediated asymmetric cyclodimerization of chiral tryptamine derivative, which established a new entry into constructing the sterically hindered vicinal quaternary stereogenic carbon centers of dimeric hexahydropyrroloindole alkaloids in one procedure. An unprecedented base-induced isomerization from the Chimonanthine skeleton to the calycanthine skeleton was observed and facilitated the synthesis of (-)-calycanthine (3).
Concise total syntheses of bis(cyclotryptamine) alkaloids via thio-urea catalyzed one-pot sequential Michael addition
Chem Commun (Camb) 2022 Mar 22;58(24):3929-3932.PMID:35244129DOI:10.1039/d2cc01008a.
Naturally occurring bis(cyclotryptamine) alkaloids feature vicinal all-carbon quaternary stereocenters with an elongated labile C-3a-C-3a' Sigma bond with impressive biological activities. In this report, we have developed a thio-urea catalyzed one-pot sequential Michael addition of bis-oxindole onto selenone to access enantioenriched dimeric 2-oxindoles with vicinal quaternary stereogenic centers at the pseudobenzylic position (up to 96% ee and >20 : 1 dr). This strategy has been successfully applied for the total syntheses of either enantiomers of Chimonanthine, folicanthine, and calycanthine.
Pd(II)-Catalyzed Intramolecular C(sp2)-H Arylation of Tryptamines Using the Nonsteric NH2 as a Directing Group
Org Lett 2021 Jan 1;23(1):42-48.PMID:33332128DOI:10.1021/acs.orglett.0c03668.
The free amine-directed C-H functionalization reactions are challenging and mainly restricted to bulky amines. In this work, we report the nonsteric NH2-directed Pd(II)-catalyzed intramolecular C(sp2)-H arylation of tryptamines, which enables the efficient, gram-scale, and regioselective synthesis of versatile 2-aryltryptamines (35 examples, up to 98% yield). This approach broadens the substrate scope of the free amine-directed C-H functionalization, not limited to bulky amine substrates. Late-stage elaborations of 2-aryltryptamines achieve the divergent construction of the complex core structures that are prevalent in highly valuable natural products such as aurantioclavine, Chimonanthine, and phalarine.
Toxicity of Chimonanthus nitens flower extracts to the golden apple snail, Pomacea canaliculata
Pestic Biochem Physiol 2019 Oct;160:136-145.PMID:31519248DOI:10.1016/j.pestbp.2019.07.015.
We studied the molluscicidal activity of Chimonanthus nitens extracts on Pomacea canaliculata (Ampullariidae). The degree of hepatopancreatic tissue damage, and its physiological and biochemical effects, was evaluated on individuals exposed to petroleum ether extracts (PEEEs). The PEEEs, ethyl acetate extract (EAEE) and water saturated n-butyl extract (SBEE) of C. nitens also had toxic effects on P. canaliculata but PEEE had the greatest molluscicidal activity. After exposure to PEEE for 24 h, the hepatopancreas of P. canaliculata had a large necrotic area. The levels of soluble sugar, soluble protein and albumin (Alb) in the hepatopancreas of P. canaliculata decreased with increasing PEEE concentration, while the activities of glutamic pyruvic transaminase (GPT), glutamic oxaloacetic transaminase (GOT) and acetylcholinesterase (AchE) increased with increasing PEEE concentration. A total of 29 compounds were identified from the PEEE of C. nitens by gas chromatography-mass spectrometry analysis. The main components were esters (48.13%), alcohols (18.43%) and the compound Chimonanthine (14.70%). The results of the molluscicidal assay, histological experiments and the physiological and biochemical experiments show that the PEEE of C. nitens could potentially be used for P. canaliculata management.
Ni-catalyzed reductive homocoupling of unactivated alkyl bromides at room temperature and its synthetic application
J Org Chem 2013 Nov 1;78(21):10960-7.PMID:24087851DOI:10.1021/jo401936v.
A room-temperature Ni-catalyzed reductive approach to homocoupling of unactivated primary, secondary, and tertiary alkyl bromides is described. The catalytic system can be easily generated from air-stable and cheap materials and demonstrates broad functional group tolerance, thus allowing facile access to useful dimeric triterpene and lignan-like molecules. Moreover, the dimerization of tertiary bromide 6 efficiently establishes sterically hindered vicinal quaternary carbons (C3a and C3a'), which is a key linkage of intriguing bispyrrolo[2,3-b]indoline alkaloids, thereby enabling us to complete the total syntheses of racemic Chimonanthine (9) and folicanthine (10). In addition, this dimerization method can be expanded to the highly stereoselective synthesis of bisperhydrofuro[2,3-b]furan (5a) and the dimeric spiroketal 5b, signifying the involvement of possible radical species.