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67416-61-9

中文名稱 11-羰基-Β-乙酰乳香酸
英文名稱 3-ACETYL-11-KETO-BETA-BOSWELLIC ACID
CAS 67416-61-9
分子式 C32H48O5
分子量 512.72
MOL 文件 67416-61-9.mol
更新日期 2024/12/30 09:00:58
67416-61-9 結(jié)構(gòu)式 67416-61-9 結(jié)構(gòu)式

基本信息

中文別名
絞股藍(lán) A
3-乙酰-11酮基乳香酸
11-羰基-Β-乙酰乳香酸
乙?;?11酮-Β-乳香酸
11-羰基-B-乙酰乳香酸
11-羰基-Β-乙酰乳香酸
乙?;?11-酮基-Β-乳香酸
11-羰基-Β-乙酰乳香酸標(biāo)準(zhǔn)品
11-羰基-Β-乙酰乳香酸AKBA
3-乙?;?11-酮基-Β-乳香酸
英文別名
AKBA
AK-BETABA
AKBA, >98%
Boswellic Acid Impurity 3
BOSWELLIC ACID, ACETYL KETO
Acetyl-11-keto-b-boswellic acid
11-keto-β-boswellic acid acetate
3-Acetyl-11-keto-(-boswellicacid
3-ACETYL-11-KETO-B-BOSWELLIC ACID
3-acetyl-11-keto-β-Boswellic Acid
所屬類別
生物化工:中草藥成分

物理化學(xué)性質(zhì)

熔點(diǎn)271℃
沸點(diǎn)600.3±55.0 °C(Predicted)
密度1.13±0.1 g/cm3(Predicted)
儲(chǔ)存條件−20°C
溶解度氯仿(微溶)、甲醇(微溶)
酸度系數(shù)(pKa)4.28±0.70(Predicted)
形態(tài)neat
顏色白色至灰白色
LogP7.418 (est)

安全數(shù)據(jù)

危險(xiǎn)性符號(hào)(GHS)GHS hazard pictograms
GHS07
警示詞警告
危險(xiǎn)性描述H302-H315-H319-H335
危險(xiǎn)類別碼36/37/38
安全說明26
WGK Germany3
海關(guān)編碼2918300000

應(yīng)用領(lǐng)域

用途1
用于含量測(cè)定/鑒定/藥理實(shí)驗(yàn)等

常見問題列表

概述
11- 羰基 -β- 乙酰乳香酸(Acetyl-11-keto-β-boswellic acid,AKBA) 能顯著地抑制 5-脂氧合酶(5-LO)的形成,從而發(fā)揮強(qiáng)大的抗炎抗氧化作用,其次對(duì)腫瘤、潰瘍和免疫調(diào)節(jié)等疾病表現(xiàn)出良好的治療前景。AKBA 可以通過抑制 TNF-α 誘導(dǎo)的 NF-κB 活化,從而抑制基質(zhì)金屬蛋白酶的活化,起到血管保護(hù)作用;同類化合物甘草酸和積雪草酸被報(bào)道,基于其良好的抗氧化作用,可通過調(diào)節(jié)體內(nèi)不同細(xì)胞因子表達(dá),從而有效抑制和逆轉(zhuǎn)血管重構(gòu)。為西黃丸藥制劑中重要活性成分。
 西黃丸藥制劑
圖:西黃丸藥制劑
西黃丸中 11-羰基-β-乙酰乳香酸的鑒別及含量測(cè)定
方法: 采用薄層色譜法和高效液相色譜法建立西黃丸中乳香類成分 11-羰基-β-乙酰乳香酸的方法。運(yùn)用高效液相色譜法對(duì)其進(jìn)行含量測(cè)定,其中 11-羰基-β-乙酰乳香酸含量最低為
0.27% ,最高為1.05% 。建立薄層色譜法和高效液相色譜法可用于西黃丸中 11-羰基-β-乙酰乳香酸的定性定量檢驗(yàn),可作為西黃丸現(xiàn)行法定檢驗(yàn)標(biāo)準(zhǔn)中乳香顯微鑒別的有益補(bǔ)充。
藥理應(yīng)用
羰基-β-乙酰乳香酸(Acetyl-11-keto-β-BoswellicAcid,AKBA)作為乳香提取物的主要藥效成分之一。一定質(zhì)量濃度的AKBA用于HL-60細(xì)胞即可觀察到細(xì)胞出現(xiàn)凋亡的形態(tài)學(xué)改變,DNA凝膠電泳出現(xiàn)了凋亡特征性的DNA小分子降解片段帶,流式細(xì)胞儀檢測(cè)早期凋亡率最高可達(dá)39.49%,總凋亡率可達(dá)99.9%,并呈時(shí)間和劑量依賴性。所以,AK-BA能誘導(dǎo)HL-60細(xì)胞凋亡,其作用呈劑量和時(shí)間依賴性。KBA作為乳香的單體成分,誘導(dǎo)白血病細(xì)胞凋亡作用強(qiáng),其作用呈一定的劑量和時(shí)間依賴性,在急性髓系白血病治療領(lǐng)域具有良好的臨床應(yīng)用前景。
參考文獻(xiàn)
【1】王醇,夏磊,宋志前,等. 乳香中 5 種乳香酸成分含量分析[J].中
國中藥雜志,2011,36( 10)1330-1332
【2】崔銳,周金云. 乳香化學(xué)和藥理的研究進(jìn)展 [J]. 中國藥學(xué)雜志,2003, 38(6): 407-410
生物活性
AKBA (Acetyl-11-keto-β-boswellic acid) 是一種從乳香中提取出的活性化合物,是新穎的 Nrf2 的活化劑。
靶點(diǎn)

Human Endogenous Metabolite

體外研究

AKBA (Acetyl-11-keto-β-boswellic acid) significantly reduced infarct volumes and apoptotic cells, and also increased neurologic scores by elevating the Nrf2 and HO-1 expression in brain tissues in middle cerebral artery occlusion (MCAO) rats at 48 hours post reperfusion. In primary cultured neurons, AKBA increased the Nrf2 and HO-1 expression, which provided protection against OGD-induced oxidative insult. Additionally, AKBA treatment increased Nrf2 binding activity to antioxidant-response elements (ARE).
AKBA (Acetyl-11-keto-β-boswellic acid) significantly inhibited human colon adenocarcinoma growth, showing arrest of the cell cycle in G1-phase and induction of apoptosis.
AKBA (Acetyl-11-keto-β-boswellic acid) triggered significant lipolysis in 3T3-L1 adipocytes as shown by reduced neutral lipids in cytosol and increased free fatty acids in culture medium. Increased lipolysis by AKBA was accompanied by up-regulation of lipolytic enzymes, adipocyte triglyceride lipase (ATGL) and hormone sensitive lipase (HSL), and a decreased expression of lipid droplet stability regulator perilipin. In addition, AKBA (Acetyl-11-keto-β-boswellic acid) treatment reduced phenotypic markers of mature adipocyte aP2, adiponectin and glut-4 in mature adipocytes.

體內(nèi)研究

AKBA (Acetyl-11-keto-β-boswellic acid) significantly prevented the formation of intestinal adenomatous polyps without toxicity to mice. AKBA's activity both in the prevention of small intestinal and colonic polyps was more potently than aspirin. Histopathologic examination revealed that AKBA's effect, that is the reduction of polyp size and degree of dysplasia, was more prominent in larger sized polyps, especially those originating in colon.
AKBA (Acetyl-11-keto-β-boswellic acid) administration in mice effectively delayed the growth of HT-29 xenografts without signs of toxicity. The activity of AKBA was more potent than that of aspirin.
AKBA (Acetyl-11-keto-β-boswellic acid) exhibited anti-cancer activity in vitro and in vivo. With oral application in mice, AKBA significantly inhibited SGC-7901 and MKN-45 xenografts without toxicity.

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