Rupestonic acid
(Synonyms: 一枝蒿酮酸) 目录号 : GC37572
Rupestonic acid 是从 Artemisia rupestris L. 中分离出的一种含多官能团的倍半萜类化合物。Rupestonic acid 能抑制流感病毒 (influenza virus)。
Cas No.:83161-56-2
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
Rupestonic acid, a sesquiterpene from Artemisia rupestris L., can inhibit influenza virus[1].
[1]. Obul M, et al. Structural modification on rupestonic acid leads to highly potent inhibitors against influenza virus. Mol Divers. 2019 Feb;23(1):1-9.
| Cas No. | 83161-56-2 | SDF | |
| 别名 | 一枝蒿酮酸 | ||
| Canonical SMILES | CC1=C2[C@@]([C@H](CC[C@@H](C(C(O)=O)=C)C2)C)([H])CC1=O | ||
| 分子式 | C15H20O3 | 分子量 | 248.32 |
| 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 | 4.0271 mL | 20.1353 mL | 40.2706 mL |
| 5 mM | 0.8054 mL | 4.0271 mL | 8.0541 mL |
| 10 mM | 0.4027 mL | 2.0135 mL | 4.0271 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。
Advances in studies on the Rupestonic acid derivatives as anti-influenza agents
Mini Rev Med Chem 2013 Feb;13(2):310-5.PMID:22625417doi
Rupestonic acid (isolated from the Chinese traditional medicine Artemisia rupestris L.) is a sesquiterpene with multifunctional groups and possess higher activity against influenza virus B. In order to improve the biological activity of Rupestonic acid, many derivatives have been synthesized and their anti-influenza activity was screened. This review describes the Rupestonic acid derivatives and their anti-influenza activity studied by our researching group.
Asymmetric Synthesis of Rupestonic acid and Pechueloic Acid
Org Lett 2017 Dec 15;19(24):6732-6735.PMID:29211481DOI:10.1021/acs.orglett.7b03459.
In this report, the originally proposed Rupestonic acid (5) and pechueloic acid (3) were efficiently synthesized. The chiral lactone 13, recycled from the degradation of saponin glycosides, was utilized to prepare the key chiral fragment 11. During the exploration of this convergent assembly strategy, the ring-closing metathesis (RCM), SmI2-prompted intermolecular addition, and [2,3]-Wittig rearrangement proved to be effective transformations for the synthesis of subunits.
Novel amides modified Rupestonic acid derivatives as anti-influenza virus reagents
Bioorg Med Chem Lett 2019 Oct 1;29(19):126605.PMID:31439378DOI:10.1016/j.bmcl.2019.08.009.
In spired by the important role of amide groups of anti-influenza drugs oseltamivir, zanamivir and peramivir in bioactivity, a series of novel amides modified Rupestonic acid derivatives were designed and synthesized. The absolute configuration of critical intermediate bearing chloride with newly formed stereocenter was confirmed by X-ray crystallographic analysis. And all new compounds were evaluated for their in vitro inhibitory activities against influenza A (H1N1 and H3N2) and influenza B viruses. The bioassay results showed that 5h with 4-fluorbenzylsulfonyl modified to 2 position of methyl rupestonate displayed the highest activity against influenza A (H1N1 and H3N2) viruses, even stronger than reference drugs oseltamivir and ribavirin (RVB), and might be recommended as a lead compound to further develop the new anti-influenza reagent.
(5R,8R)-2-(3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octa-hydro-azulen-5-yl)acrylic acid (Rupestonic acid)
Acta Crystallogr Sect E Struct Rep Online 2008 Jan 23;64(Pt 2):o479.PMID:21201504DOI:10.1107/S1600536808001402.
The title compound, C(15)H(20)O(3), crystallizes with two independent mol-ecules in the asymmetric unit. In both mol-ecules, the seven-membered ring adopts a chair conformation. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains extending in the [201] direction. The absolute configuration was assigned on the basis of the starting materials.
Rupestonic acid derivative YZH-106 suppresses influenza virus replication by activation of heme oxygenase-1-mediated interferon response
Free Radic Biol Med 2016 Jul;96:347-61.PMID:27107768DOI:10.1016/j.freeradbiomed.2016.04.021.
Given the limitation of available antiviral drugs and vaccines, there remains to be a pressing need for novel anti-influenza drugs. Rupestonic acid derivatives were reported to have an anti-influenza virus activity, but their mechanism remains to be elucidated. Herein, we aim to evaluate the antiviral activity of YZH-106, a Rupestonic acid derivative, against a broad-spectrum of influenza viruses and to dissect its antiviral mechanisms. Our results demonstrated that YZH-106 exhibited a broad-spectrum antiviral activity against influenza viruses, including drug-resistant strains in vitro. Furthermore, YZH-106 provided partial protection of the mice to Influenza A virus (IAV) infection, as judged by decreased viral load in lungs, improved lung pathology, reduced body weight loss and partial survival benefits. Mechanistically, YZH-106 induced p38 MAPK and ERK1/2 phosphorylation, which led to the activation of erythroid 2-related factor 2 (Nrf2) that up-regulated heme oxygenase-1 (HO-1) expression in addition to other genes. HO-1 inhibited IAV replication by activation of type I IFN expression and subsequent induction of IFN-stimulated genes (ISGs), possibly in a HO-1 enzymatic activity-independent manner. These results suggest that YZH-106 inhibits IAV by up-regulating HO-1-mediated IFN response. HO-1 is thus a promising host target for antiviral therapeutics against influenza and other viral infectious diseases.