Incensole Acetate
(Synonyms: 因香酚乙酸酯) 目录号 : GC38213
A diterpene with diverse biological activities
Cas No.:34701-53-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Incensole acetate is a diterpene originally isolated from frankincense produced by B. carterii that has diverse biological activities.1,2,3 It is an activator of transient receptor potential vanilloid 3 (TRPV3) that induces calcium influx in HEK293 cells expressing TRPV3 (EC50 = 16 ?M).2 Incensole acetate (60-140 ?M) inhibits degradation of inhibitor of NF-κB (IκBα) in TNF-α-stimulated HeLa cells.1 It reduces apoptosis, increases in malondialdehyde (MDA) levels, and the production of reactive oxygen species (ROS) induced by amyloid-β (25-35) peptide in human olfactory bulb neural stem cells (hOBNSCs).3 Incensole acetate (50 mg/kg) reduces paw edema in mice in a model of hind paw inflammation induced by carrageenan.1 It also increases the time spent in the open arms of the elevated plus maze and reduces immobility in the forced swim test, indicating anxiolytic and antidepressant-like activity, respectively.2
1.Moussaieff, A., Shohami, E., Kashman, Y., et al.Incensole acetate, a novel anti-inflammatory compound isolated from Boswellia resin, inhibits nuclear factor-κB activationMol. Pharmacol.72(6)1657-1664(2007) 2.Moussaieff, A., Rimmerman, N., Bregman, T., et al.Incensole acetate, an incense component, elicits psychoactivity by activating TRPV3 channels in the brainFASEB J.22(8)3024-3034(2008) 3.El-Magd, M.A., Khalifa, S.F., A Alzahrani, F.A., et al.Incensole acetate prevents beta-amyloid-induced neurotoxicity in human olfactory bulb neural stem cellsBiomed. Pharmacother.105813-823(2018)
| Cas No. | 34701-53-6 | SDF | |
| 别名 | 因香酚乙酸酯 | ||
| Canonical SMILES | CC([C@@]12C/C=C(C)/CC/C=C(C)/CC[C@H](OC(C)=O)[C@@](O2)(C)CC1)C | ||
| 分子式 | C22H36O3 | 分子量 | 348.52 |
| 溶解度 | DMSO : 100 mg/mL (286.93 mM; Need ultrasonic) | 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 | 2.8693 mL | 14.3464 mL | 28.6928 mL |
| 5 mM | 0.5739 mL | 2.8693 mL | 5.7386 mL |
| 10 mM | 0.2869 mL | 1.4346 mL | 2.8693 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。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Distribution of the anti-inflammatory and anti-depressant compounds: Incensole and Incensole Acetate in genus Boswellia
Phytochemistry 2019 May;161:28-40.PMID:30802641DOI:10.1016/j.phytochem.2019.01.007.
Incensole and its acetate have shown anti-inflammatory and anti-depression activities due to their ability to activate ion channels in the brain to alleviate anxiety or depression. The natural occurrence of these two structurally and medicinally fascinating 14-membered diterpenoids was reported mainly from the genus Boswellia. Incensole and Incensole Acetate were detected in and isolated from both essential oils and resins of frankincense. One total synthesis was reported for incensole. Both incensole and its acetate served as precursors for several synthetic transformations. Given the fact that no specific enzymes were isolated from Boswellia trees, the major sources for incensole and Incensole Acetate, the biosynthetic pathway of these two compounds was only speculated. Recent studies on incensole and Incensole Acetate including ours have revealed another secret of the ancient drug. Understanding their mode of action will open a door in modern neurobiology and provides new insights on the mysterious diseases of the nervous system. This review interpretatively discusses the natural existence of incensole and Incensole Acetate, the variation of their percentages in different Boswellia species and other sources, their synthetic modifications, their biosynthesis and their therapeutic potential.
Incensole Acetate prevents beta-amyloid-induced neurotoxicity in human olfactory bulb neural stem cells
Biomed Pharmacother 2018 Sep;105:813-823.PMID:29913410DOI:10.1016/j.biopha.2018.06.014.
β-Amyloid peptide (Aβ) is a potent neurotoxic protein associated with Alzheimer's disease (AD) which causes oxidative damage to neurons. Incensole Acetate (IA) is a major constituent of Boswellia carterii resin, which has anti-inflammatory and protective properties against damage of a large verity of neural subtypes. However, this neuroprotective effect was not studied on human olfactory bulb neural stem cells (hOBNSCs). Herein, we evaluated this effect and studied the underlying mechanisms. Exposure to Aβ25-35 (5 and 10 μM for 24 h) inhibited proliferation (revealed by downregulation of Nestin and Sox2 gene expression), and induced differentiation (marked by increased expression of the immature neuronal marker Map2 and the astrocyte marker Gfap) of hOBNSCs. However, pre-treatment with IA (100 μM for 4 h) stimulated proliferation and differentiation of neuronal, rather than astrocyte, markers. Moreover, IA pretreatment significantly decreased the Aβ25-35-induced viability loss, apoptotic rate (revealed by decreased caspase 3 activity and protein expression, downregulated expression of Bax, caspase 8, cyto c, caspase3, and upregulated expression of Bcl2 mRNAs and proteins, in addition to elevated mitochondrial membrane potential and lowered intracellular Ca+2). IA reduced Aβ-mediated ROS production (revealed by decreased intracellular ROS and MDA level, and increased SOD, CAT, and GPX contents), and inhibited Aβ-induced inflammation (marked by down-regulated expression of IL1b, TNFa, NfKb, and Cox2 genes). IA also significantly upregulated mRNA and protein expression of Erk1/2 and Nrf2. Notably, IA increased the antioxidant enzyme heme oxygenase-1 (HO-1) expression and this effect was reversed by HO-1 inhibitor zinc protoporphyrin (ZnPP) leading to reduction of the neuroprotective effect of IA against Aβ-induced neurotoxicity. These findings clearly show the ability of IA to initiate proliferation and differentiation of neuronal progenitors in hOBNSCs and induce HO-1 expression, thereby protecting the hOBNSCs cells from Aβ25-35-induced oxidative cell death. Thus, IA may be applicable as a potential preventive agent for AD by its effect on hOBNSCs and could also be used as an adjuvant to hOBNSCs in cellular therapy of neurodegenerative diseases.
Synthesis and antidepressant-like effects of new 5-epi-incensole and 5-epi- Incensole Acetate in chronic unpredictable mild stress model of depression; behavioural and biochemical correlates
Biomed Pharmacother 2022 Dec;156:113960.PMID:36411640DOI:10.1016/j.biopha.2022.113960.
In the current investigation, 5-epi-incensole (3) and 5-epi-incensole acetate (5) were synthesized from the most potent anti-depressant constituents incensole (1) and Incensole Acetate (2) of Boswellia papyrifera Hochst. The resulting compounds were evaluated for their ability to ameliorate depressive symptoms in forced swim test (FST) and tail suspension test (TST) in chronic unpredictable mild stress (CUMS) induced depression paradigm. The results demonstrated that compounds 3 and 5 at the doses of 1 and 3 mg/kg administered for 28 days, significantly reduced the immobility time in FST and TST and were devoid of any effect on locomotor activity in the open field test (OFT). Both compounds 3 and 5 also reversed CUMS-induced reduction in the weight of animals and aversion in sucrose preference. The tested compounds also inhibited Monoamine oxidase-A (MAO) enzyme and increased the levels of brain noradrenaline (NA) and 5-Hydroxytryptamine (5-HT), decreased plasma corticosterone and pro-inflammatory cytokines including TNF-α, IL-6 in hippocampal homogenates. Compounds 3 and 5 also significantly reduced the increased lipid peroxidation and nitrite levels; decreased glutathione levels, and catalase activities in mice undergoing CUMS protocol. The binding mode of compounds 3 and 5 was predicted at the monoamine oxidase substrate binding site by molecular docking having docking scores of > -6 kcal/mol. Taken together these data revealed that compounds 3 and 5 exerted antidepressant-like effects in chronic unpredictable mild stress-induced depression paradigm and are likely mediated via modulating the central oxidative stress, MAO-A activity with a consequent increase in brain NA and 5-HT levels in inflammatory pathways.
The Effects of Incensole Acetate on Neuro-inflammation, Brain-Derived Neurotrophic Factor and Memory Impairment Induced by Lipopolysaccharide in Rats
Neurochem Res 2021 Sep;46(9):2473-2484.PMID:34173963DOI:10.1007/s11064-021-03381-3.
Incensole Acetate (IA) is a major component of Boswellia serrata resin that has been shown to have anti-inflammatory, anti-oxidant and neuroprotective properties. The present study determined the effect of IA on lipopolysaccharide (LPS)-induced memory impairment, and hippocampal cytokines and oxidative stress indicators level. We used 32 Wistar rats (220-250 g weight) randomly divided into four groups. The control group, which only received the saline-diluted DMSO (vehicle); LPS group which received LPS and was treated with the vehicle; and two IA-treated groups which received 2.5 or 5 mg/ kg IA before LPS injection. Morris water maze (MWM) and passive avoidance (PA) tests were performed. Finally, the brains were removed and were used to assess cytokines levels and oxidative stress status. Compared to the LPS group, IA administration reduced the time spent and path traveled to reach the hidden platform during 5 days of learning in MWM while increased the time spent in the target quadrant in the probe test. Moreover, IA increased latency while decreased entry number and time spent in the dark chamber of PA test compared to the LPS group. Additionally, pre-treatment with IA attenuated interleukin(IL)-6, tumor necrosis alpha (TNF-α), glial fibrillary acidic protein (GFAP), malondialdehyde (MDA) and nitric oxide (NO) metabolites levels while increased those of IL-10, total thiol, superoxide dismutase (SOD), catalase (CAT) and brain-derived neurotrophic factor (BDNF). Our results indicated that IA improved LPS-induced learning and memory impairments. The observed effects seem to be mediated via a protective activity against neuro-inflammation and brain tissue oxidative damage and through improving BDNF.
Efficient preparation of incensole and Incensole Acetate, and quantification of these bioactive diterpenes in Boswellia papyrifera by a RP-DAD-HPLC method
Nat Prod Commun 2012 Mar;7(3):283-8.PMID:22545396doi
Incensole and Incensole Acetate, found in incense, are encouraging potent bioactive diterpenic cembrenoids, inhibiting Nuclear Factor-kappaB activation. Furthermore, Incensole Acetate elicits psycho-activity in mice by activating the TRPV3 channels in the brain. Starting from crude extracts of the incense species Boswellia papyrifera Hochst., a convenient procedure for the efficient large-scale synthesis of incensole and its acetate is presented. Additionally, a reversed-phase, diode-array-detection, high-performance liquid chromatography (RP-DAD-HPLC) method for the quantification of incensole and Incensole Acetate is reported, indicating that these two compounds are typical biomarkers for B. papyrifera.