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山楂酸 | 4373-41-5

中文名称
山楂酸
中文别名
2Α-羟基齐墩果酸;马斯里酸;(2alpha,3beta)-2,3-二羟基齐墩果-12-烯-28-酸;山楂叶提取物
英文名称
maslinic acid
英文别名
2α,3β-dihydroxyolean-12-en-28-oic acid;crategolic acid;2α,3β-dihydroxy-12-oleanen-28-oic acid;2α-hydroxy-oleanolic acid;crataegolic acid;masilinic acid;(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
山楂酸化学式
CAS
4373-41-5
化学式
C30H48O4
mdl
——
分子量
472.709
InChiKey
MDZKJHQSJHYOHJ-LLICELPBSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    267~269℃
  • 沸点:
    570.0±50.0 °C(Predicted)
  • 密度:
    1.14±0.1 g/cm3(Predicted)
  • 溶解度:
    丙酮:可溶1mg/mL,澄清,无色
  • LogP:
    7.870 (est)
  • 物理描述:
    Solid
  • 颜色/状态:
    Crystalline solid
  • 蒸汽压力:
    2.3X10-15 mm Hg at 25 °C (est)
  • 解离常数:
    pKa = 4.81 (est)

计算性质

  • 辛醇/水分配系数(LogP):
    6.5
  • 重原子数:
    34
  • 可旋转键数:
    1
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.9
  • 拓扑面积:
    77.8
  • 氢给体数:
    3
  • 氢受体数:
    4

ADMET

毒理性
  • 解毒与急救
/SRP:/ 立即急救:确保已经进行了充分的中毒物清除。如果患者停止呼吸,开始人工呼吸,最好使用需求阀复苏器、袋阀面罩装置或口袋面罩,按训练操作。如有必要,执行心肺复苏。立即用缓慢流动的冲洗受污染的眼睛。不要催吐。如果发生呕吐,让患者前倾或置于左侧(如果可能的话,头部向下)以保持呼吸道畅通,防止吸入。保持患者安静,维持正常体温。寻求医疗帮助。 /毒物A和B/
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 基本治疗:建立专利气道(如有需要,使用口咽或鼻咽气道)。如有必要,进行吸痰。观察呼吸不足的迹象,如有需要,辅助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺肿,如有必要,进行治疗……。监测休克,如有必要,进行治疗……。预防癫痫发作,如有必要,进行治疗……。对于眼睛污染,立即用冲洗眼睛。在运输过程中,用0.9%的生理盐(NS)持续冲洗每只眼睛……。不要使用催吐剂。对于摄入,如果患者能吞咽、有强烈的干呕反射且不流口,则用温冲洗口腔,并给予5毫升/千克,最多200毫升的进行稀释……。在去污后,用干燥的无菌敷料覆盖皮肤烧伤……。/毒药A和B/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 解毒与急救
/SRP:/ 高级治疗:对于无意识、严重肺肿或严重呼吸困难的病人,考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺肿……。对于严重的支气管痉挛,考虑给予β激动剂,如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W /SRP: "保持开放",最小流量/。如果出现低血容量的迹象,使用0.9%的生理盐(NS)或乳酸林格氏液。对于伴有低血容量迹象的低血压,谨慎给予液体。注意液体过载的迹象……。使用地西泮劳拉西泮治疗癫痫……。使用丙美卡因化物协助眼部冲洗……。 /Poisons A and B/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
橄榄及其衍生物是地中海饮食的重要组成部分,被认为具有抗癌作用...研究了由五环三萜组成的橄榄提取物对HT-29细胞增殖和凋亡的影响,主要成分为马斯林酸(73.25%)和齐墩果酸(25.75%)。研究剂量依赖性效应显示,马斯林酸的EC50值为73.96 +/- 3.19 uM/L,齐墩果酸EC50值为26.56 +/- 2.55 uM/L,具有抗增殖活性,且不表现出坏死。通过显微镜观察细胞膜通透性的变化,以及检测DNA片段,证实了凋亡现象,在用含有150和55.5 uM/L马斯林酸和齐墩果酸的橄榄果实提取物处理24小时的HT-29细胞中,分别有40.9 +/- 3.9%和24.5 +/- 1.5%的细胞出现这些变化。在处理24小时后,caspase-3以剂量依赖性方式被激活。含有200 uM/L马斯林酸和74 uM/L齐墩果酸提取物使caspase-3样活性增加了6倍,与对照组细胞相比。细胞凋亡是通过内在途径诱导的,这是通过在用含有150和55.5 uM/L马斯林酸和齐墩果酸的橄榄果实提取物处理的细胞线粒体中产生超氧阴离子来证明的...
/ALTERNATIVE and IN VITRO TESTS/ Olives and their derivatives represent an important component of the Mediterranean diet that has been considered to be protective against cancer... the effect on cell proliferation and apoptosis in HT-29 cells of an extract from the skin of olives composed of pentacyclic triterpenes with the main components maslinic acid (73.25%) and oleanolic acid (25.75%) was investigated. Studies of the dose-dependent effects showed antiproliferative activity at an EC50 value of 73.96 +/- 3.19 uM/L of maslinic acid and 26.56 +/- 2.55 uM/L of oleanolic acid without displaying necrosis. Apoptosis was confirmed by the microscopic observation of changes in membrane permeability in 40.9 +/- 3.9% and detection of DNA fragmentation in 24.5 +/- 1.5% of HT-29 cells incubated for 24 hr with olive fruit extract containing 150 and 55.5 uM/L of maslinic and oleanolic acids, respectively. Caspase-3 was activated in a dose-dependent manner after incubation for 24 hr. The extract containing 200 uM/L maslinic acid and 74 uM/L oleanolic acid increased caspase-3-like activity to 6-fold that of control cells. Programmed cell death was induced by the intrinsic pathway, as evidenced by the production of superoxide anions in the mitochondria of cells treated with olive fruit extracts containing 150 and 55.5 uM/L of maslinic and oleanolic acids, respectively...
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 人类毒性摘录
/替代和体外测试/ 蛋白激酶C(PKC)与致癌作用有关,在癌症进展过程中表现出不同的表达谱。对饮食植物化学物质在癌症信号通路调控方面的研究一直在进行,以寻找有效的信号调节剂。本研究旨在评估马斯林酸对人类B淋巴母细胞(Raji细胞)中PKC表达的抑制作用,并确定表达的PKC同种型。使用PepTag assay进行非放射性检测PKC,以确定马斯林酸对PKC活性的影响。在Raji细胞中,使用20 nM PMA诱导6小时获得最高表达。将马斯林酸的抑制效果与四种PKC抑制剂(H-7, rottlerin, sphingosine, staurosporine)和两种三萜类化合物(齐墩果酸熊果酸)进行比较。马斯林酸、司他鲁斯汀、H-7、鞘氨醇、rottlerin、熊果酸齐墩果酸的IC50值分别为11.52、0.011、0.767、2.45、5.46、27.93和39.29 uM。通过西方印迹法在Raji细胞中鉴定出四种PKC同种型,分别为PKC beta I、beta II、delta和zeta。马斯林酸以浓度依赖性方式抑制PKC beta I、delta和zeta的表达。这些初步结果表明,马斯林酸在Raji细胞中对PKC活性具有潜在的抑制作用。马斯林酸可能是一种有潜力的抗癌化学预防剂,可能参与调节通过PKC受体激活的许多下游信号通路。
/ALTERNATIVE and IN VITRO TESTS/ Protein kinase C (PKC) has been implicated in carcinogenesis and displays variable expression profiles during cancer progression. Studies of dietary phytochemicals on cancer signaling pathway regulation have been conducted to search for potent signaling regulatory agents. The present study was designed to evaluate any suppressive effect of maslinic acid on PKC expression in human B-lymphoblastoid cells (Raji cells), and to identify the PKC isoforms expressed. Effects of maslinic acid on PKC activity were determined using a PepTag assay for non-radioactive detection of PKC. The highest expression in Raji cells was obtained at 20 nM PMA induced for 6 hours. Suppressive effects of maslinic acid were compared with those of four PKC inhibitors (H- 7, rottlerin, sphingosine, staurosporine) and two triterpenes (oleanolic acid and ursolic acid). The IC50 values achieved for maslinic acid, staurosporine, H-7, sphingosine, rottlerin, ursolic acid and oleanolic acid were 11.52, 0.011, 0.767, 2.45, 5.46, 27.93 and 39.29 uM, respectively. Four PKC isoforms, PKC beta I, beta II, delta, and zeta were identified in Raji cells via western blotting. Maslinic acid suppressed the expression of PKC beta I, delta, and zeta in a concentration-dependent manner. These preliminary results suggest promising suppressive effects of maslinic acid on PKC activity in Raji cells. Maslinic acid could be a potent cancer chemopreventive agent that may be involved in regulating many downstream signaling pathways that are activated through PKC receptors.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 安全说明:
    S24/25
  • WGK Germany:
    3
  • 海关编码:
    2940000000

SDS

SDS:c8d34e4f98436d25c328b49d2146a0d3
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制备方法与用途

药理作用

山楂酸是一种五环三萜酸,主要存在于油橄榄等多种天然植物中,对人体安全。近年来的研究发现,它具有抗癌、抗氧化、抗艾滋病、抗菌和抗糖尿病等多种生物活性,引起了广泛的关注。

西班牙格拉纳达大学的科学家们揭示了山楂酸能够抑制丝氨酸蛋白酶的作用机制。而这种蛋白酶正是艾滋病病毒所利用的关键酶之一,用于将病毒从感染细胞中释放到外部环境,进一步扩散至全身。因此,山楂酸在抗肿瘤和抗艾滋病方面表现突出,可以显著降低艾滋病病毒体内扩散的概率达80%。

注意事项

本品应低温干燥保存,特殊产品需要在氮气环境下保存。若长时间保存不当,其含量可能会有所下降。

生物活性

MAslinic acid 可抑制 NF-κB p65 的 DNA 结合活性,并消除 IκB-α 磷酸化。

目标靶点
  • NF-κB
体外研究
  • MAslinic acid (MA) 抑制 LPS 引发的 NF-κB 转位至细胞核和 IκB-α 的磷酸化。它还被证实能够抑制骨髓单核细胞中的破骨细胞生成,并在胰腺癌细胞中抑制 TNF-α 诱导的 NF-κB 活性及其下游基因的表达。
  • 为了确认橄榄果渣提取物 (OPEs) 在 RAW264.7 细胞中的抗炎作用是否归因于 MAslinic acid,进行了剂量依赖性实验。结果显示,10-20 μM 的 MAslinic acid 是有效的浓度,显著抑制了 TNF-α 的产生,并减少了 IL-1、IL-6 和 COX-2 mRNA 表达。
  • 在 LPS 引发的 RAW 264.7 细胞中,MAslinic acid (10 和 20 μM) 显著抑制 NF-κB p65 的 DNA 结合活性,并显著减少 LPS 引起的 IκB-α 磷酸化。
体内研究

当小鼠以 200 mg/kg 的剂量给予 MAslinic acid (MA) 后,4 小时后发现其能明显缓解 λ-卡拉胶诱导的足部肿胀,并显著抑制了炎症反应,与对照组相比(0.91±0.51 mm 和 1.79±0.4 mm)。

化学性质

易溶于吡啶氯仿甲醇混合溶剂,微溶于甲醇乙酸乙酯。来源包括红枣、橄榄、山楂等植物。

用途

用于含量测定/鉴定/药理实验等。 药理药效:抗肿瘤、抗艾滋病病毒、抗炎、抗菌等多种作用。

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量