Agarotetrol
(Synonyms: 沉香四醇) 目录号 : GC30663
Agarotetrol是从沉香中分离得到的一种色酮衍生物，对磷酸二酯酶3A（PDE 3A）的抑制活性较弱，IC50值大于100μM。
Cas No.:69809-22-9
Sample solution is provided at 25 µL, 10mM.
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Agarotetrol is the chromone derivative from Agarwood, showing very low phosphodiesterase (PDE) 3A inhibitory activity with IC50 value > 100μM[1]. The aqueous extract of agarwood is characterized by a high concentration of Agarotetrol, a bioactive compound demonstrating significant sedative properties. Upon thermal activation, Agarotetrol compound releases benzylacetone, a characteristic aromatic constituent[2]. Agarotetrol serves as a crucial quality control marker for the standardization of agarwood in herbal medicinal preparations[3].
In vitro, Agarotetrol has potential cell protective activity[4]. After 24 hours of incubation with 20μM Agarotetrol, the 150μM corticosterone-induced damage in PC12 cells was significantly alleviated, with a cell viability of 79.50 ± 1.79% [4]. In silico molecular docking and molecular dynamic simulation showed that Agarotetrol had good binding with humanlegumain protein[5].
In vivo, Agarotetrol can cross the blood-brain barrier in vivo with an estimated blood-brain barrier penetration value of 0.8 in SD rats[5]. The combined administration of agarwood essential oil (24.85mg/kg) and agarotetrol-enriched extract powder (7.28mg/kg) (prepared into a cyclodextrin mixture) demonstrated significant pharmacological effects on sleep parameters in p-Chlorophenylalanine-induced insomnia SD rats. Nasal cavity of administration for 7 days resulted in enhanced sleep onset efficiency, reduced sleep latency, and extended total sleep duration [6]. Following a 30-day oral administration regimen of Agarotetrol at a dosage of 6.0g/kg/day, comprehensive biodistribution analysis demonstrated a tissue-specific accumulation pattern in experimental rats, with the highest concentration detected in renal tissue, followed by hepatic, cardiac, and cerebral tissues in decreasing order of magnitude[7].
References:
[1] Sugiyama T, Narukawa Y, Shibata S, et al. Three new 5, 6, 7, 8-tetrahydroxy-5, 6, 7, 8-tetrahydrochromone derivatives enantiomeric to agarotetrol from agarwood[J]. Journal of natural medicines, 2018, 72: 667-674.
[2] Takamatsu S, Ito M. Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating[J]. Journal of natural medicines, 2018, 72: 537-541.
[3] Takamatsu S, Ito M. Agarotetrol as an index for evaluating agarwood in crude drug products[J]. Journal of Natural Medicines, 2022, 76(4): 857-864.
[4] Zhang L, Yi P, Yan H, et al. Five new 2-(2-phenylethyl) chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China[J]. Natural Products and Bioprospecting, 2022, 12(1): 2.
[5] Alugoju P, Bhandare V V, Patil V S, et al. In silico molecular docking and molecular dynamic simulation of agarwood compounds with molecular targets of Alzheimer’s disease[J]. F1000Research, 2024, 12: 230.
[6] Lai Y, Hua L, Yang J, et al. The effect of Chinese agarwood essential oil with cyclodextrin inclusion against PCPA-induced insomnia rats[J]. Molecules, 2023, 28(2): 635.
[7] Hou H, Chen T, Xu Z, et al. Study and exploration of the pharmacokinetics of traditional Tibetan medicine Ruyi Zhenbao tablets after single and long-term administration[J]. Frontiers in Pharmacology, 2022, 13: 948693.
Agarotetrol是从沉香中分离得到的一种色酮衍生物，对磷酸二酯酶3A（PDE 3A）的抑制活性较弱，IC50值大于100μM[1]。沉香水提物的特征性成分是含有高浓度的Agarotetrol，Agarotetrol具有显著的镇静作用。在热活化条件下，Agarotetrol可释放出特征性芳香成分苯乙酮。Agarotetro已成为沉香药材质量控制的重要标志物，在中药制剂标准化过程中发挥关键作用[3]。
在体外，Agarotetrol具有潜在的细胞保护活性[4]。当PC12细胞与20μM Agarotetrol共孵育24小时后，150μM皮质酮诱导的细胞损伤得到显著缓解，细胞存活率达到79.50 ± 1.79%[4]。通过分子对接和分子动力学模拟分析，Agarotetrol与humanlegumain蛋白具有良好的结合特性[5]。
Agarotetrol在体内能够穿透血脑屏障，在SD大鼠血脑屏障透过率估计值为0.8 [5]。将沉香精油（24.85mg/kg）与富含Agarotetrol的提取物粉末（7.28mg/kg）制备成环糊精混合物后联合给药，在对氯苯丙氨酸诱导的失眠SD大鼠模型中显示出显著的睡眠参数改善作用。经鼻腔给药7天后，可提高睡眠起始效率、缩短睡眠潜伏期并延长总睡眠时间[6]。在SD大鼠中进行为期30天、剂量为6.0 g/kg/天的Agarotetrol口服给药后，Agarotetrol具有组织特异性分布模式，其中肾脏组织中的浓度最高，其次是肝脏、心脏和脑组织，呈递减趋势[7]。
| Cell experiment [1]: | |
Cell lines | PC12 cell |
Preparation Method | Undifferentiated PC12 cells were cultured in Dulbecco's Modified Eagle Medium (DMEM) supplemented with 10% heat-inactivated fetal bovine serum, 100U/mL penicillin, and 100μg/mL streptomycin, maintained at 37°C in a humidified 5% CO2 atmosphere. For experimental treatments, cells were divided into three groups: (1) untreated control (blank, 24h), (2) negative control (150μM, 24h), and (3) positive control (150μM corticosterone plus 20μM Agarotetrol, 24h). Cells were plated in 96-well plates at a density of 1 × 104 cells per well and allowed to adhere for 24 hours prior to compound administration. Following 48 hours of treatment, cell viability was assessed using the MTS assay, with absorbance measurements recorded at 492 nm using a microplate reader. |
Reaction Conditions | 20μM; 24h |
Applications | Agarotetrol has significant protective properties against corticosterone-induced PC12 cell injury. |
| Animal experiment [2]: | |
Animal models | SD rats |
Preparation Method | Sixty-four Sprague-Dawley rats (body weight 180-220g, age 3-4 weeks) were randomly allocated into four experimental groups (n=16 per group) with equal gender distribution (8 males and 8 females): (1) vehicle control, (2) high-dose Agarotetrol (6.0g/kg/day), (3) medium-dose Agarotetrol (3.0g/kg/day), and (4) low-dose Agarotetrol (1.5g/kg/day). Within each group, eight animals were sacrificed at one month post-treatment initiation, and the remaining eight were maintained for an additional two-week withdrawal period prior to sample collection. Serial blood sampling was performed via the retro-orbital plexus at multiple time points: baseline (day 1), mid-treatment (day 15), and treatment completion (day 30). At each sampling day, blood was collected at 0.25, 0.5, 0.75, 1, 2, 4, 8, and 24h post-administration. |
Dosage form | 1.5g/kg/day, 3.0g/kg/day and 6.0g/kg/day for 1, 15 and 30 days; p.o. |
Applications | Agarotetrol has a wide distribution in the rats, after long-term administration, the distribution order of Agarotetrol in various tissues of rats was kidney > liver > heart > brain. |
References: | |
| Cas No. | 69809-22-9 | SDF | |
| 别名 | 沉香四醇 | ||
| Canonical SMILES | O=C1C=C(CCC2=CC=CC=C2)OC3=C1[C@H](O)[C@@H](O)[C@@H](O)[C@@H]3O | ||
| 分子式 | C17H18O6 | 分子量 | 318.32 |
| 溶解度 | DMSO : ≥ 250 mg/mL (785.37 mM) | 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。 |
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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 | 3.1415 mL | 15.7075 mL | 31.4149 mL |
| 5 mM | 0.6283 mL | 3.1415 mL | 6.283 mL |
| 10 mM | 0.3141 mL | 1.5707 mL | 3.1415 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。
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Quality Control & SDS
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- Purity: >98.00%
- COA (Certificate Of Analysis)
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