Deoxylimonin
目录号 : GC60755Desoxylimonin是从葡萄柚籽中分离得到的一种三萜化合物。Desoxylimonin为母体的衍生物的抗癌、镇痛和抗炎活性优于母体化合物。
Cas No.:989-23-1
Sample solution is provided at 25 µL, 10mM.
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Desoxylimonin is a triterpenoid compound isolated from grapefruit seed. Desoxylimonin derivatives has better anticancer, analgesic and anti-inflammatory activitythan the lead compound[1].
[1]. Shaochi Wang, et al. Discovery of deoxylimonin δ-lactam derivative with favorable anti-inflammation and antinociception efficacy from chemical modified limonin/deoxylimonin analogs. Bioorg Chem. 2020 Jul;100:103886.
Cas No. | 989-23-1 | SDF | |
Canonical SMILES | C[C@]1(C2=CC3=O)[C@@](CC[C@]2([C@@](C4=COC=C4)([H])O3)C)([H])[C@]([C@@](C5)([H])OC(C)6C)(COC5=O)[C@@]6([H])CC1=O | ||
分子式 | C26H30O7 | 分子量 | 454.51 |
溶解度 | DMSO : 100 mg/mL (220.02 mM; Need ultrasonic) | 储存条件 | 4°C, protect from light |
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1 mg | 5 mg | 10 mg | |
1 mM | 2.2002 mL | 11.0009 mL | 22.0017 mL |
5 mM | 0.44 mL | 2.2002 mL | 4.4003 mL |
10 mM | 0.22 mL | 1.1001 mL | 2.2002 mL |
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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。
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A practical synthesis of amino limonin/Deoxylimonin derivatives as effective mitigators against inflammation and nociception
RSC Med Chem 2020 Jun 16;11(7):843-847.PMID:33479680DOI:10.1039/d0md00117a.
A practical synthetic route, consisting of 5 steps, has been developed and applied successfully for converting limonin/Deoxylimonin into the corresponding amino derivatives I- 5a-I- 5e and II- 5a-II- 5e. Deoxylimonin analogs II- 5a and II- 5b bearing an open A ring structure underwent ring closure reaction by employing the Mitsunobu procedure to afford II- 6a and II- 6b. All of the 12 newly synthesized compounds were subjected to preliminary screening for evaluating their inflammation and nociception inhibition efficacy. The most promising compounds, I- 5b and II- 5d, were selected for further investigation by a carrageenan-induced mouse paw edema model, both of which displayed a dose-response dependent manner and demonstrated superior anti inflammation capacity to that of indomethacin in the first 2 hours.
Discovery of Deoxylimonin δ-lactam derivative with favorable anti-inflammation and antinociception efficacy from chemical modified limonin/Deoxylimonin analogs
Bioorg Chem 2020 Jul;100:103886.PMID:32371249DOI:10.1016/j.bioorg.2020.103886.
Chemical modifications on the A ring of limonin (1) and Deoxylimonin (2) afforded 28 structural characterized derivatives, which were firstly subjected to preliminary in vivo analgesic and anti-inflammatory screen by mice model. The most promising candidate, Deoxylimonin analog II-B-2 (70 mg/kg) with 3,4-dimethoxyphenylethyl moiety substitued δ-lactam in the A ring, exhibited better analgesic activity than aspirin (200 mg/kg) and stronger anti-inflammatory efficacy than naproxen (150 mg/kg). Further in vivo evaluation confirmed its advantage over limonin and showed dose-response dependent manner, and follow-up research suggested that the anti-inflammatory effect of compound II-B-2 may be attributed to the downregulation of cyclooxygenase 2 expression and the suppression of prostaglandin E2 formation.
Further studies on the anticancer activity of citrus limonoids
J Agric Food Chem 2004 Jul 28;52(15):4908-12.PMID:15264934DOI:10.1021/jf049698g.
Research in this laboratory has shown that some citrus limonoids can inhibit the development of 7,12-dimethylbenz[a]anthracene-induced oral tumors. The data from these studies have suggested that certain rings in the limonoid nucleus may be critical to antineoplastic activity. Using the hamster cheek pouch model, three new limonoids (ichangensin, Deoxylimonin, and obacunone) have now been tested for cancer chemopreventive activity. In the first experiment, it was found that the treatments with ichangensin had no effect on tumor number or burden. In the second experiment, obacunone reduced tumor number and burden by 25 and 40%, respectively, whereas Deoxylimonin reduced tumor number and burden by 30 and 50%, respectively. The results with Deoxylimonin were significant, p < 0.05. Overall, the data indicated that changes in the A ring of the limonoid nucleus can lead to a loss of anticancer activity, whereas changes in the D ring can be tolerated without any apparent loss of biological activity.