Acetylalkannin
(Synonyms: Alkannin acetate) 目录号 : GC60556
Acetylalkannin(Alkanninacetate)是一种从Arnebiaeuchroma中分离出来的isohexenylnaphthazarin色素，具有抗菌和细胞毒性作用。
Cas No.:34232-27-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Acetylalkannin (Alkannin acetate) is an isohexenylnaphthazarin pigment isolated from Arnebia euchroma with antimicrobial and cytotoxic activities[1].
[1]. Harilaos Damianakos, et al. Antimicrobial and cytotoxic isohexenylnaphthazarins from Arnebia euchroma (Royle) Jonst. (Boraginaceae) callus and cell suspension culture. Molecules. 2012 Dec 3;17(12):14310-22.
| Cas No. | 34232-27-4 | SDF | |
| 别名 | Alkannin acetate | ||
| Canonical SMILES | O=C1C([C@@H](OC(C)=O)C/C=C(C)\C)=CC(C2=C1C(O)=CC=C2O)=O | ||
| 分子式 | C18H18O6 | 分子量 | 330.33 |
| 溶解度 | DMSO : 100 mg/mL (302.73 mM; Need ultrasonic) | 储存条件 | 4°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 | 3.0273 mL | 15.1364 mL | 30.2728 mL |
| 5 mM | 0.6055 mL | 3.0273 mL | 6.0546 mL |
| 10 mM | 0.3027 mL | 1.5136 mL | 3.0273 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。
Relayed chromatography - Countercurrent chromatography in series with liquid chromatography for the separation of natural products
J Chromatogr A 2022 Aug 2;1676:463205.PMID:35709606DOI:10.1016/j.chroma.2022.463205.
Chromatography is an essential method for separating natural products. In this study, we proposed the concept of 'relayed chromatography', based on the strategy of combining different chromatography with relayed resolution by in-situ concentration technique. The following chromatographic methods were used: high-speed countercurrent chromatography (HSCCC), silica gel liquid chromatography (silica gel LC), and reverse phase liquid chromatography (reverse phase LC). The proposed strategy was effectively applied to the preparative separation of naturally existing naphthaquinones. After the first separation stage (silica gel LC), Acetylalkannin (1) was directly collected, while fractions 1, 4 and 5 were collected and respectively subjected to recycling CCC separation after concentration. Thus, deoxyshikonin (2), 8-O-methyl-11-O-acetylshikonin (6), β-acetoxyisovalerylalkannin (7) and alkannin (8) were collected. Fraction 2 was concentrated and injected in reverse phase LC separation. After collection of isobutyrylalkannin (3), the remaining effluent from reverse phase LC retained the peak resolution (R4,5=0.45) and was injected into a recycling CCC elution. Finally, β, β-dimethylacrylalkannin (4), and isovalerylalkannin (5) were collected with sufficient resolution (R4,5=1.25). Eight naturally occurring naphthaquinones were thus isolated from Arnebia euchroma. The purities of all the compounds were determined by HPLC to be > 90%, and the chemical structures were determined by spectral method. Among the aforementioned compounds, 8-O-methyl-11-O-acetylshikonin (6) was separated as a new compound from A. euchroma. In conclusion, the relayed strategy that retains the resolution of the previous chromatographic stage can improve CCC separation efficiency, which may expand the range of application of CCC combined with different chromatography to the separation of natural products.
Cytotoxic compounds from endemic Arnebia purpurea
Nat Prod Commun 2015 Apr;10(4):595-6.PMID:25973485doi
Phytochemical studies of the roots and aerial parts of endemic Arnebia purpurea S. Erik & H. Sumbul resulted in the isolation and characterization of four naphthoquinones [isovalerylalkannin (1), α-methyl-n-butanoyl alkannin (2), Acetylalkannin (3), and alkannin (4)], a triterpene derivative [3-O-acetyl-oleanolic acid (5)], a steroid [β-sitosterol (6)], three flavonoid glycosides [isorhamnetin-3-O-rutinoside (7), kaempferol-3-O-rutinoside (8), kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside (9)] and a phenolic acid [rosmarinic acid (10)]. 3-O-Acetyl-oleanolic acid, isorhamnetin-3-O-rutinoside, kaempferol-3-O-mrutinoside, and kaempferol 3-O-(5"-acetyl) apiofuranoside 7-O-rhamnopyranoside are reported from an Arnebia species for the first time. Cytotoxic activities on L929 murine fibrosarcoma cell line of the isolated compounds were investigated using MTT assay. Naphthoquinones (1-4) showed intermediate cytotoxic activity in comparison with the standard, doxorubicin.
Isolation and chemopreventive evaluation of novel naphthoquinone compounds from Alkanna tinctoria
Anticancer Drugs 2013 Nov;24(10):1058-68.PMID:24025561DOI:10.1097/CAD.0000000000000017.
Botanically derived natural products have recently become an attractive source of new chemotherapeutic agents. To explore active anticolorectal cancer compounds, we carried out phytochemical studies on Alkanna tinctoria and isolated eight quinone compounds. Using different spectral methods, compounds were identified as alkannin (1), Acetylalkannin (2), angelylalkannin (3), 5-methoxyangenylalkannin (4), dimethylacryl alkannin (5), arnebifuranone (6), alkanfuranol (7), and alkandiol (8). Compounds 4, 7, and 8 are novel compounds. The structures of the three novel compounds were elucidated on the basis of extensive spectroscopic evidence including high-resolution mass spectrometry and nuclear magnetic resonance spectra. The antiproliferative effects of these eight compounds on HCT-116 and SW-480 human colorectal cancer cells were determined using the MTS method. Cell cycle and apoptosis were determined using flow cytometry. Enzymatic activities of caspases were determined using a colorimetric assay, and interactions of compound 4 and caspase 9 were explored by docking analysis. Among the eight compounds, alkannin (1), angelylalkannin (3), and 5-methoxyangenylalkannin (4) showed strong antiproliferative effects, whereas compound 4 showed the most potent effects. Compound 4 arrested cancer cells in the S and G2/M phases, and significantly induced cell apoptosis. The apoptotic effects of compound 4 were supported by caspase assay and docking analysis. The structural-functional relationship assay suggested that to increase anticancer potential, future modifications on alkannin (1) should focus on the hydroxyl groups at C-5 and C-8.
Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp.: E. plantagineum and E. gaditanum
Phytochemistry 2017 Sep;141:162-170.PMID:28633108DOI:10.1016/j.phytochem.2017.06.004.
Isohexenylnaphthazarins are commonly found in the root periderm of several Boraginaceous plants and are known for their broad range of biological activities. The work described herein concerns the biological activity of compounds from the roots of Echium plantagineum L. and Echium gaditanum Boiss (Boraginaceae) collected from field sites in southern Spain and Australia. Bioactivity was assessed using etiolated wheat coleoptile bioassay and in vitro growth inhibitory activity in HeLa and IGROV-1 cells. The quantification of four isohexenylnaphthazarins (shikonin/alkannin, deoxyshikonin/deoxyalkannin, acetylshikonin/Acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin) was performed by LC-MS/MS using juglone as internal standard. Correlation coefficient values for the activities and concentrations of these four analytes were in the linear range and were greater than 0.99. Acetylshikonin/Acetylalkannin and dimethylacrylshikonin/dimethylacrylalkannin were present in the highest concentrations in extracts of both species. The results reveal that greatest overall inhibition was observed in both bioassays with E. gaditanum extracts. Strong correlations between time of collection, sampling location and bioactivity were identified.
Synthesis and cytotoxicity study of alkannin derivatives
Eur J Med Chem 2004 Sep;39(9):755-64.PMID:15337288DOI:10.1016/j.ejmech.2004.05.004.
Alkannin derivatives (3-19) were prepared through the reaction of beta,beta-dimethylacrylalkannin (1), the most abundant isohexenylnaphthazarin isolated from the roots of Arnebia euchroma, with different types of nucleophiles such as amines and thiols in the absence or presence of a reducing agent. The cytotoxicities of 1-8, 10-14 and 19 against four human carcinoma cell line (GLC-82, CNE2, Bel-7402, K-562) were found to be markedly higher than that of the naturally occurring beta,beta-dimethylacrylalkannin (1) and Acetylalkannin (2). This study also shed light on the understanding of the biological activities in terms of the chemical reactivity of alkannins.