8-Geranyloxypsoralen
(Synonyms: 8-香叶草氧基补骨脂素) 目录号 : GC35201
8-Geranyloxypsoralen 是从葡萄柚中分离出的一种呋喃香豆素，能作为 P450 3A4 (CYP3A4) 的有效抑制剂，其 IC50 值为 3.93 μM。
Cas No.:7437-55-0
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
8-Geranyloxypsoralen is a furanocoumarin isolated from grapefruit, acts as a potent inhibitor of P450 3A4 (CYP3A4) with an IC50 of 3.93 μM[1]. IC50: 3.93 μM (P450 3A4)[1]
[1]. Row EC, et al. Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4. Bioorg Med Chem. 2006 Jun 1;14(11):3865-71.
| Cas No. | 7437-55-0 | SDF | |
| 别名 | 8-香叶草氧基补骨脂素 | ||
| Canonical SMILES | O=C1C=CC2=CC3=C(OC=C3)C(OC/C=C(C)/CC/C=C(C)/C)=C2O1 | ||
| 分子式 | C21H22O4 | 分子量 | 338.4 |
| 溶解度 | Soluble in DMSO | 储存条件 | 4°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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.9551 mL | 14.7754 mL | 29.5508 mL |
| 5 mM | 0.591 mL | 2.9551 mL | 5.9102 mL |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 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。
Synthesis of 8-Geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4
Bioorg Med Chem 2006 Jun 1;14(11):3865-71.PMID:16481174DOI:10.1016/j.bmc.2006.01.046.
Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency. In this study, we report the effects of a series of novel furanocoumarins based on the naturally occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC(50) values ranging from 0.78+/-0.11 to 3.93+/-0.53 microM. The reduced furan derivative dihydro-8-geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4.
Bio-guided isolation of leishmanicidal and trypanocidal constituents from Pituranthos battandieri aerial parts
Parasitol Int 2021 Jun;82:102300.PMID:33540121DOI:10.1016/j.parint.2021.102300.
Protozoan pathogens that cause neglected tropical diseases are a major public health concern in tropical and developing countries. In the course of our ongoing search for new lead compounds as potential antiprotozoal agents, this study aims to perform a bio-guided fractionation of Pituranthos battandieri, using an in vitro assay against Leishmania amazonensis and Trypanosoma cruzi. Two known polyacetylenes, (-)-panaxydiol (1) and (-)-falcarindiol (2) were identified from the ethanolic extract of the aerial parts of P. battandieri as the main bioactive constituents. Compounds 1 and 2 showed similar potency (IC50 values of 5.76 and 5.68 μM, respectively) against L. amazonensis to miltefosine (IC50 value of 6.48 μM), the reference drug, and low toxicity on macrophage cell lines J774. Moreover, compound 1 exhibited moderate activity (IC50 23.24 μM) against T. cruzi. In addition, three known furanocoumarins, 8-Geranyloxypsoralen (3), 8-geranyloxy-5-methoxypsoralen (4), and phellopterin (5) were isolated. Their structures were elucidated by NMR and MS analysis. Compounds 1 and 2 are described for the first time in the Pituranthos genus, and this is the first report on their antiprotozoal activity. These results highlight this type of polyacetylenes as an interesting scaffold for the development of novel antiparasitic drugs.
Nematicidal coumarins from Heracleum candicans Wall
Nat Prod Res 2008 May 20;22(8):666-71.PMID:18569707DOI:10.1080/14786410701766463.
The root extract of Heracleum candicans Wall. exhibited antagonistic activities against nematodes Bursaphelenchus xylophilus (Steiner et Buhrer) Nickle and Panagrellus redivivus (Linn.) Goodey. Through bioassay-guided fractionations, three coumarins were obtained from the extract of H. candicans and determined to be 8-Geranyloxypsoralen (1), imperatorin (2), and heraclenin (3) based on spectra data. All three compounds possessed nematicidal activities against the two tested nematodes. The median lethal concentrations (LC(50)) of compounds 1-3 at 72 h were 188.3, 161.7, and 114.7 mg L(-1) respectively against B. xylophilus and were 117.5, 179.0, and 148.7 mg L(-1) respectively against P. redivivus. This is the first report about species in the Umbelliferae family that possesses nematicidal activity.
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor
Bioorg Med Chem 2012 Jan 15;20(2):784-8.PMID:22222157DOI:10.1016/j.bmc.2011.12.002.
The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC(50) value of 9.9 μM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5-methoxypsoralen (35), 8-Geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC(50) values <25.0 μM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.
Characterization of Oxygenated Heterocyclic Compounds and in vitro Antioxidant Activity of Pomelo Essential Oil
Drug Des Devel Ther 2021 Mar 2;15:937-947.PMID:33688168DOI:10.2147/DDDT.S299678.
Purpose: Citrus essential oils are widely used for aromatherapy and the alternative treatment of chronic diseases. Beyond the aroma substances, they are known to contain bioactive nonvolatile components; however, little knowledge has been gained about nonvolatiles in the essential oil of pomelo (Citrus grandis Osbeck), the largest citrus fruit. The purpose of this study was to analyze the nonvolatile oxygenated heterocyclic compounds (OHCs) of pomelo essential oils and evaluate their in vitro antioxidant activities for further development. Methods: Cold-pressed essential oil (CPEO) and distilled essential oil (DEO) were obtained from the peel of the Liangping pomelo cultivar. High-performance liquid chromatography (HPLC) coupled with a photodiode array and fluorescence detection method was developed to identify and quantify the OHCs of the two essential oils. Ferric reducing antioxidant power and 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2-phenyl-4,4,5,5-tetramethyl-imidazoline-1-oxyl 3-oxide (PTIO) radical scavenging assays were used to determine the antioxidative capabilities. Results: Thirteen OHCs were identified in CPEO. Coumarins such as meranzin (2.0 mmol L-1) and furanocoumarins such as isoimperatorin (1.3 mmol L-1) composed the majority of nonvolatiles in CPEO. These OHCs were characterized by high proportion (58%) of side chain epoxides. Five OHCs, namely, auraptenol, 6',7'-dihydroxybergamottin (6',7'-DHB), imperatorin, isoimperatorin and 8-Geranyloxypsoralen were first identified in pomelo CPEO. Eight OHCs were detected at trace amounts in pomelo DEO. Antioxidant assays showed that CPEO was multiple times more potent than DEO regarding the total reducing power and radical scavenging capacity. Clearance of PTIO, a stable reactive oxygen species, followed slow kinetics. Conclusion: Coumarins and furanocoumarins, two families of OHCs, constituted most of the nonvolatile components in CPEO. The nonvolatiles contributed significantly to the in vitro antioxidant activity of CPEO. Pomelo CPEO showed good prospects as a potential long-lasting natural antioxidant.