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一枝蒿酮酸

NMR下載 COA and HPLC MSDS下載
names：
Rupestonic acid
CAS號：
83161-56-2
MDL Number：
MF(分子式)： C15H20O3 MW(分子量)： 248.32
EINECS: Reaxys Number:
Pubchem ID:24094149 Brand:BIOFOUNT

一枝蒿酮酸(83161-56-2,Rupestonic acid)是從Artemisia rupestris L.中分離出的一種含多官能團的雙半鏈類化合物。一枝蒿酮酸能抑制流感病毒（流感病毒）。

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中文別名	一枝蒿酮酸(83161-56-2);鼠李酮酸;
英文別名	Rupestonic acid(83161-56-2);rupestonic acid;rupestonic acid; 2-((5R,8S,8aS)-3,8-Dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydro-azulen-5-yl)-acrylic acid; Pechueloic acid; (+)-pechueloic acid; (+)-3-oxo-1αH,7αH,10αH-guaia-4,11-dien-12-oic acid; 2-((5R,8S,8aS)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylic acid;
CAS號	83161-56-2
Inchi	InChI=1S/C15H20O3/c1-8-4-5-11(9(2)15(17)18)6-13-10(3)14(16)7-12(8)13/h8,11-12H,2,4-7H2,1,3H3,(H,17,18)/t8-,11+,12-/m0/s1
InchiKey	ZFHSKBJBODQVBX-AXTRIDKLSA-N
分子式 Formula	C15H20O3
分子量 Molecular Weight	248.32
溶解度Solubility
性狀	Solid
儲藏條件 Storage conditions	請根據(jù)產(chǎn)品建議的存儲條件進行存儲,Please store the product under the recommended condition sin the description.

一枝蒿酮酸(83161-56-2,Rupestonic acid)實驗注意事項：
1.實驗前需戴好防護眼鏡，穿戴防護服和口罩，佩戴手套，避免與皮膚接觸。
2.實驗過程中如遇到有毒或者刺激性物質(zhì)及有害物質(zhì)產(chǎn)生，必要時實驗操作需要手套箱內(nèi)完成以免對實驗人員造成傷害
3.實驗后產(chǎn)生的廢棄物需分類存儲，并交于專業(yè)生物廢氣物處理公司處理，以免造成環(huán)境污染Experimental considerations:
1. Wear protective glasses, protective clothing and masks, gloves, and avoid contact with the skin during the experiment.
2. The waste generated after the experiment needs to be stored separately, and handed over to a professional biological waste gas treatment company to avoid environmental pollution.

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產(chǎn)品說明	一枝蒿酮酸(83161-56-2,Rupestonic acid)是從Artemisia rupestrisL. 中分離出的一種含多官能團的倍半萜類有機化合物
Introduction	一枝蒿酮酸(83161-56-2,Rupestonic acid)a sesquiterpene fromArtemisia rupestrisL., can inhibitinfluenza virus.
Application1
Application2
Application3

一枝蒿酮酸(83161-56-2,Rupestonic acid)藥理學：

一枝蒿酮酸Rupestonic acid 是從 Artemisia rupestris L. 中分離出的一種含多官能團的倍半萜類化合物。Rupestonic acid 能抑制流感病毒 (influenza virus)。

警示圖
危險性	warning
危險性警示	Not available
安全聲明	H303吞入可能有害+H313皮膚接觸可能有害+H2413吸入可能對身體有害
安全防護	P264處理后徹底清洗+P280戴防護手套/穿防護服/戴防護眼罩/戴防護面具+P305如果進入眼睛+P351用水小心沖洗幾分鐘+P338取出隱形眼鏡（如果有）并且易于操作,繼續(xù)沖洗+P337如果眼睛刺激持續(xù)+P2393獲得醫(yī)療建議/護理
備注	實驗過程中防止吸入、食入，做好安全防護

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.

Structure-activity relationship studies of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses PMID 28196702; Bioorganic & medicinal chemistry letters 2017 03; 27(6):1484-1487 N

Advances in studies on the rupestonic acid derivatives as anti-influenza agents PMID 22625417; Mini reviews in medicinal chemistry 2013 Feb; 13(2):310-5 (Review Article) Name matches: sesquiterpene ru

[The structure and absolute configuration of isorupestonic acid from Artemisia rupestris L] PMID 1805508; Yao xue xue bao = Acta pharmaceutica Sinica 1991; 26(7):505-9 Name matches: sesquiterpene rupe

Structural modification on rupestonic acid leads to highly potent inhibitors against influenza virus PMID 29971616; Molecular diversity 2019 Feb; 23(1):1-9 Name matches: neuraminidase rupestonic acid

一枝蒿酮酸(83161-56-2,Rupestonic acid)參考文獻：

1、Structural modification on rupestonic acid leads to highly potent inhibitors against influenza virus
Mamateli Obul, Xincheng Wang, Jiangyu Zhao, Gen Li, Haji Akber Aisa & Guozheng Huang

Abstract Influenza viruses are responsible for seasonal epidemics and occasional pandemics, which cause significant morbidity and mortality. Although several drugs (adamantanes and neuraminidase inhibitors) are available in the market, the worldwide spread of drug-resistant influenza strains poses an urgent need for novel antiviral drugs. Artemisia rupestris L. is a folk medicine used to treat cold. In this paper, we structurally modified rupestonic acid, a bioactive component of A. rupestris, to synthesize a series of 2-substituted rupestonic acid methyl esters (3a–3o). Their structures were fully characterized by 1H NMR, 13C NMR, HRMS spectra. Among them, compounds 3b and 3c exhibited potent activities against influenza H1N1 with micromolar IC50 values and might serve as new lead compounds for the treatment of influenza.

2、Novel amides modified rupestonic acid derivatives as anti-influenza virus reagents
Gen Li 1, Mamateli Obul 2, Jiang-Yu Zhao 1, Ge-Yu Liu 1, Wei Lu 3, Haji Akber Aisa

Abstract 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.

3、1,2,3-Triazole-containing derivatives of rupestonic acid: click-chemical synthesis and antiviral activities against influenza viruses
Yao-Wu He 1, Chang-Zhi Dong 2, Jiang-Yu Zhao 3, Lin-Lin Ma 4, Yu-Huan Li 4, Haji Akber Aisa

Abstract Two series of rupestonic acid derivatives, (1-substituted-1H-1,2,3-triazol-4-yl)methyl 2-((5R,8S,8aS)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylate and N-(1-substituted-1H-1,2,3-triazol-4-yl)methyl 2-((5R,8S,8aS)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylamide were easily and efficiently synthesized via click chemistry. These compounds were tested for their in vitro activities against various strains of influenza A virus (H1N1, oseltamivir resistant H1N1, H3N2) and influenza B virus. The results showed that nine compounds were active against the H1N1 strain of influenza A virus and among them the best one 14a, was as active as the reference drugs, Oseltamivir and Ribavirin. Some of them were also active on the Oseltamivir resistant H1N1 strain. In regards to influenza B virus, twenty-one compounds over thirty were active and seven of them 7b, 8b, 9b, 10a, 11b, 12b, 13b showed better activity than Ribavirin. The structure-activity relationship of these compounds is discussed on the basis of each type of the viruses studied. Furthermore, four best representative compounds 7b, 10a, 12b and 14a were evaluated in a plaque assay experiment using MDCK cells and RBV as control compound and the results showed that 7b, 10a and 12b were better than RBV in inhibiting plaque formation, in good accordance with their anti-influenza B activities.

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