1,3-Dicaffeoylquinic acid
(Synonyms: 1,3-二咖啡酰奎宁酸; 1,3-O-Dicaffeoylquinic acid; 1,5-Dicaffeoylquinic acid) 目录号 : GC35037
1,3-Dicaffeoylquinic acid能抑制HIV-1整合酶的3'端加工、末端连接以及解体过程，IC50值分别为0.35、0.56和0.84μg/ml。
Cas No.:19870-46-3
Sample solution is provided at 25 µL, 10mM.
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1,3-Dicaffeoylquinic acid inhibits the 3' end processing, terminal connection, and disintegration process of HIV-1 integrase, with IC50 values of 0.35, 0.56, and 0.84μg/ml respectively [1]. 1,3-Dicaffeoylquinic acid is a type of phenolic compound found in artichokes [2]. 1,3-Dicaffeoylquinic acid possesses antioxidant activity and is a free radical scavenger [3].
In vitro, 1,3-Dicaffeoylquinic acid (0.25-1μM; 30min) reduces the free radical levels released by human polymorphonuclear cells (PMNs) stimulated by the chemokine N-formyl-Met-Leu-Phe in a dose-dependent manner [4]. 1,3-Dicaffeoylquinic acid (0, 5, 10, 50, 100, and 500μM; 2h) pretreatment increases the cell viability of rat primary cortical neurons stimulated by amyloid β1-42 (Aβ42) in a concentration-dependent manner, activates Trk A and PI3K/Akt and Erkl/2 pathways, inhibits GSK3β and regulates Bcl-2/Bax expression [5].
In vivo, local administration of 1,3-Dicaffeoylquinic acid (5-500μg/mL; 5μL; 7 days) dose-dependently reduces corneal epithelial defects in dry eye disease (DED) model mice and increases tear production, while inhibiting inflammatory cytokines and T cell infiltration in the ocular surface and lacrimal glands [6]. In the forced swimming test and tail suspension test, treatment with 1,3-Dicaffeoylquinic acid (30mg/kg/day; 5 days; p.o.) significantly improves depressive-like behavior in ovariectomized (OVX) model mice [7].
References:
[1] Robinson, W.E., Jr., Cordeiro, M., Abdel-Malek, S., et al. Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: Inhibition of the core catalytic domain of human immunodeficiency virus integrase. Mol. Pharmacol. 50(4), 846-855 (1996).
[2] Jun N J, Jang K C, Kim S C, et al. Radical scavenging activity and content of cynarin (1, 3-dicaffeoylquinic acid) in Artichoke (Cynara scolymus L.)[J]. Journal of applied biological chemistry, 2007, 50(4): 244-248.
[3] Danino O, Gottlieb H E, Grossman S, et al. Antioxidant activity of 1, 3-dicaffeoylquinic acid isolated from Inula viscosa[J]. Food research international, 2009, 42(9): 1273-1280.
[4] Heilmann, J., Merfort, I., and Weiss, M.Radical scavenger activity of different 3',4'-dihydroxyflavonols and 1,5-dicaffeoylquinic acid studied by inhibition of chemiluminescencePlanta Med.61(5)435-438(1995).
[5] Xiao HB, Cao X, Wang L, et al. 1,5-dicaffeoylquinic acid protects primary neurons from amyloid β 1-42-induced apoptosis via PI3K/Akt signaling pathway. Chin Med J (Engl). 2011;124(17):2628-2635.
[6] Yoon CH, Jang HJ, Ryu JS, et al. 1,5-Dicaffeoylquinic acid from Pseudognaphalium affine ameliorates dry eye disease via suppression of inflammation and protection of the ocular surface. Ocul Surf. 2023;29:469-479.
[7] Lim D W, Kim M, Yoon M, et al. 1, 3-Dicaffeoylquinic acid as an active compound of Arctium lappa root extract ameliorates depressive-like behavior by regulating hippocampal nitric oxide synthesis in ovariectomized mice[J]. Antioxidants, 2021, 10(8): 1281.
1,3-Dicaffeoylquinic acid能抑制HIV-1整合酶的3'端加工、末端连接以及解体过程，IC50值分别为0.35、0.56和0.84μg/ml [1]。1,3-Dicaffeoylquinic acid是一种存在于洋蓟中的酚类化合物 [2]。1,3-Dicaffeoylquinic acid具有抗氧化活性，是一种自由基清除剂 [3]。
在体外，1,3-Dicaffeoylquinic acid（0.25-1μM; 30min)以剂量依赖性方式降低了趋化因子N-formyl-Met-Leu-Phe刺激的人多形核细胞（PMNs）释放的自由基水平 [4]。1,3-Dicaffeoylquinic acid（0、5、10、50、100和500μM; 2h）预处理以浓度依赖性方式增加了淀粉样β1-42（Aβ42）刺激的大鼠原代皮质神经元的细胞活力，激活了Trk A和PI3K/Akt和Erkl/2途径，抑制GSK3β并调节Bcl-2/Bax表达 [5]。
在体内，1,3-Dicaffeoylquinic acid（5–500μg/mL; 5μL; 7 days）的局部施用剂量依赖性地减少了干眼病（DED）模型小鼠的角膜上皮缺陷并增加泪液产生，同时抑制眼表面和泪腺中的炎症细胞因子和T细胞浸润 [6]。在强迫游泳测试和尾悬测试中，1,3-Dicaffeoylquinic acid（30mg/kg/day; 5 days; p.o.）治疗显著改善了卵巢切除术（OVX）模型小鼠的抑郁样行为 [7]。
| Cell experiment [1]: | |
Cell lines | Neurons cells |
Preparation Method | Neurons were grown in a 96-well plate (approximate 5x104 cells/ml). Cells were first treated with several concentrations of Aβ42 (0, 5, 10, 20, 40, and 80μM) for 6 hours to explore the appropriate toxic concentration. In another part of the experiment, to observe the protective effect of 1,3-Dicaffeoylquinic acid, the neurons were pretreated with several concentrations of 1,3-Dicaffeoylquinic acid (0, 5, 10, 50, 100, and 500μM) alone for 2 hours and then co-treated with 40μM Aβ42 for 6 hours and washed carefully several times with phosphate-buffered saline (PBS). The cell viability was determined using the CCK-8 method. |
Reaction Conditions | 0, 5, 10, 50, 100 and 500μM; 2h |
Applications | 1,3-Dicaffeoylquinic acid pretreatment increased the cell viability of rat primary cortical neurons stimulated by Aβ42 in a concentration-dependent manner. |
| Animal experiment [2]: | |
Animal models | C57BL/6N mice (Ovariectomy) |
Preparation Method | After the 1-week acclimatization period, female C57BL/6N mice were anesthetized with 2% isoflurane. Both ovaries were ovariectomized (OVX) via small bilateral dorsal flank incisions and subsequent removal of ovaries at 6 weeks of age. OVX mice were divided into four groups (n = 8 mice per group) as follows: (1) Group 1, OVX animals receiving 0.9% saline (p.o.) and vehicle (i.p.); (2) Group 2, OVX animals receiving 1,3-Dicaffeoylquinic acid 30mg/day (p.o.) and vehicle (i.p.); (3) Group 3, OVX animals receiving 0.9% saline (p.o.) and 7-NI (selective nNOS inhibitor, i.p.); (4) Group 4, OVX animals receiving 1,3-Dicaffeoylquinic acid 30mg/day (p.o.) and 7-NI (i.p.). The OVX mice were administered i.p. injection of 7-NI (50mg/kg) once daily for 5 days, while those in the untreated 7-NI groups were injected with an equal volume of vehicle (0.9% saline with 1% DMSO and 1% Tween 80). On day 5, behavior analysis was initiated 1h after treatment was administered. |
Dosage form | 30mg/kg/day; 5 days; p.o. |
Applications | In the forced swimming test and tail suspension test, 1,3-Dicaffeoylquinic acid treatment significantly improved the depressive-like behaviors in mice induced by OVX. |
References: | |
| Cas No. | 19870-46-3 | SDF | |
| 别名 | 1,3-二咖啡酰奎宁酸; 1,3-O-Dicaffeoylquinic acid; 1,5-Dicaffeoylquinic acid | ||
| Canonical SMILES | O=C([C@@]1(OC(/C=C/C2=CC=C(O)C(O)=C2)=O)C[C@@H](OC(/C=C/C3=CC=C(O)C(O)=C3)=O)[C@H](O)[C@H](O)C1)O | ||
| 分子式 | C25H24O12 | 分子量 | 516.45 |
| 溶解度 | DMSO: 100 mg/mL (193.63 mM) | 储存条件 | Store at -20°C, protect from light |
| 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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.9363 mL | 9.6815 mL | 19.363 mL |
| 5 mM | 387.3 μL | 1.9363 mL | 3.8726 mL |
| 10 mM | 193.6 μL | 968.1 μL | 1.9363 mL |
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| 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 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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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，
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2.
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Quality Control & SDS
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- Purity: >98.50%
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