Noracronycine
(Synonyms: NSC 103005) 目录号 : GC47791
An alkaloid with antimalarial activity
Cas No.:13161-79-0
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
Noracronycine is an alkaloid originally isolated from G. pentaphylla that has antimalarial activity.1,2 It is active against P. yoelii when used at a concentration of 10 µg/ml.
1.Govindachari, T.R., Pai, B.R., and Subramaniam, P.S.Alkaloids of Glycosmis pentaphylla (Retz.) correaTetrahedron22(10)3245-3252(1966) 2.Fujioka, H., Nishiyama, Y., Furukawa, H., et al.In vitro and in vivo activities of atalaphillinine and related acridone alkaloids against rodent malariaAntimicrob. Agents Chemother.33(1)6-9(1989)
| Cas No. | 13161-79-0 | SDF | |
| 别名 | NSC 103005 | ||
| Canonical SMILES | CC(C=C1)(C)OC2=C1C3=C(C(O)=C2)C(C4=CC=CC=C4N3C)=O | ||
| 分子式 | C19H17NO3 | 分子量 | 307.3 |
| 溶解度 | 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 | 3.2541 mL | 16.2707 mL | 32.5415 mL |
| 5 mM | 0.6508 mL | 3.2541 mL | 6.5083 mL |
| 10 mM | 0.3254 mL | 1.6271 mL | 3.2541 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。
Chemistry of acronycine. VIII. Selective synthesis of dimers and trimers of Noracronycine and related compounds
J Nat Prod 1985 Jul-Aug;48(4):536-46.PMID:4045471DOI:10.1021/np50040a004.
Improved synthetic procedures for the formation of a number of dimeric derivatives of Noracronycine (2) are described based on acid-catalyzed reactions in methanolic HCl or methanolic H2SO4. A detailed analysis of their high-field proton nmr spectral characteristics is presented. The synthesis and structure determination of a new trimer of Noracronycine (2) possessing the linear-angular-angular structure (15) is described.
Chemistry of acronycine, XII. Further oligomers of Noracronycine
J Nat Prod 1986 Mar-Apr;49(2):210-7.PMID:3734808DOI:10.1021/np50044a003.
The polymerization of Noracronycine (2) with methanolic HCl has yielded a second tetramer of 2, designated as AB-4 and determined to have the structure 7 through spectroscopic analysis. Two further pentamers of 2, designated as AB-6A and AB-6B, have also been obtained, and their structures are tentatively proposed as 9 and 5, respectively.
Chemistry of acronycine. IX. Formation of dimers of noracronycine--mechanistic studies
J Nat Prod 1985 Jul-Aug;48(4):547-54.PMID:4045472DOI:10.1021/np50040a005.
The mechanisms of two acid-mediated coupling reactions of Noracronycine (2) have been studied using deuterium-labeled acids. Dimerization of Noracronycine (2) using D2SO4 afforded AB-1-d4 (8), whereas coupling 2 and dihydronoracronycine (3) in 10N DCl/MeOD (1:2.5) afforded dihydro AB-2-d8 (15). In addition, in the dimerization reaction of 2 using D2SO4-CH3OD (1:1) followed by dilution with D2O, AB-1-d16 (19) was obtained instead of 8. Initial protonation at the C2 position of Noracronycine (2) was verified during these studies.
Isolation, Characterization of Undescribed Alkaloids, and Semisynthetic Modifications of Cytotoxic Pyranoacridone Alkaloids from Glycosmis pentaphylla
ACS Omega 2023 Mar 13;8(12):11201-11212.PMID:37008118DOI:10.1021/acsomega.2c08100.
Two undescribed alkaloids (10 and 11), along with nine known alkaloids (1-9), have been isolated from the stem and root bark of Glycosmis pentaphylla. Among them are carbocristine (11), a carbazole alkaloid first time isolated from a natural source, and acridocristine (10), a pyranoacridone alkaloid first time isolated from the genus "Glycosmis". In vitro cytotoxicity of isolated compounds has been analyzed on breast cancer (MCF-7), lung cancer (CALU-3), and squamous cell carcinoma cell lines (SCC-25). The results demonstrated that compounds are moderately active. In order to study the structural activity relationship of majorly isolated compounds, semisynthetic modifications have been done on majorly isolated compounds such as des-N-methylacronycine (4) and Noracronycine (1) to synthesize 11 semisynthetic derivatives (12-22) on functionalizable -NH and -OH groups of the pyranoacridone scaffold at 12th and 6th positions. Semisynthetic derivatives are explored on the same cell lines as isolated compounds, and the results exhibit that semisynthetic compounds showed potent cytotoxic activity compared with naturally isolated compounds. In the case of CALU-3, the dimer at -OH position of Noracronycine (1), i.e., compound 22, showed 24-fold better activity with an IC50 of 4.49 μM compared with Noracronycine (1) with IC50 97.5 μM. In MCF-7, the dimer at -OH position of Noracronycine (1), i.e., compound 22, showed 14-fold better activity with an IC50 of 13.2 μM compared with Noracronycine (1) with IC50 187 μM.
Chemistry of acronycine IV. Minor constituents of acronine and the phytochemistry of the genus Acronychia
J Nat Prod 1984 Mar-Apr;47(2):285-91.PMID:6736969DOI:10.1021/np50032a009.
In the course of isolating acronycine (1) from an alkaloid fraction of the bark of Acronychia baueri (Rutaceae), five alkaloids, 1,2,3-trimethoxy-10-methyl-acridone (9), 1,3,4-trimethoxy-10-methyl-acridone (10), des-N-methyl acronycine (14), normelicopine (5), and Noracronycine (2), were isolated. Four of the isolates are new to the genus, and phytochemical analysis of the genus Acronychia is presented.