Heraclenol
(Synonyms: 白芷属脑) 目录号 : GC38393
Heraclenol，一种香豆素，是从当归果实中分离得到的，具有抗菌活性。
Cas No.:31575-93-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Heraclenol, a coumarin, is isolated from the fruits of Angelica lucida, and exhibits antibacterial activities[1].
[1]. Widelski J, et al. Coumarins from Angelica lucida L.--antibacterial activities. Molecules. 2009 Jul 27;14(8):2729-34.
| Cas No. | 31575-93-6 | SDF | |
| 别名 | 白芷属脑 | ||
| Canonical SMILES | CC(C)(O)[C@H](O)COC1=C(OC=C2)C2=CC(C=C3)=C1OC3=O | ||
| 分子式 | C16H16O6 | 分子量 | 304.29 |
| 溶解度 | Soluble in DMSO | 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 | 3.2863 mL | 16.4317 mL | 32.8634 mL |
| 5 mM | 0.6573 mL | 3.2863 mL | 6.5727 mL |
| 10 mM | 0.3286 mL | 1.6432 mL | 3.2863 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。
In Vitro and In Vivo Studies of Heraclenol as a Novel Bacterial Histidine Biosynthesis Inhibitor against Invasive and Biofilm-Forming Uropathogenic Escherichia coli
Antibiotics (Basel) 2023 Jan 6;12(1):110.PMID:36671311DOI:10.3390/antibiotics12010110.
Globally, urinary tract infections (UTIs) are one of the most frequent bacterial infections. Uropathogenic Escherichia coli (UPEC) are the predominant etiological agents causing community and healthcare-associated UTIs. Biofilm formation is an important pathogenetic mechanism of UPEC responsible for chronic and recurrent infections. The development of high levels of antimicrobial resistance (AMR) among UPEC has complicated therapeutic management. Newer antimicrobial agents are needed to tackle the increasing trend of AMR and inhibit biofilms. Heraclenol is a natural furocoumarin compound that inhibits histidine biosynthesis selectively. In this study, for the first time, we have demonstrated the antimicrobial and antibiofilm activity of Heraclenol against UPEC. The drug reduced the bacterial load in the murine catheter UTI model by ≥4 logs. The drug effectively reduced bacterial loads in kidney, bladder, and urine samples. On histopathological examination, Heraclenol treatment showed a reversal of inflammatory changes in the bladder and kidney tissues. It reduced the biofilm formation by 70%. The MIC value of Heraclenol was observed to be high (1024 µg/mL), though the drug at MIC concentration did not have significant cytotoxicity on the Vero cell line. Further molecular docking revealed that Heraclenol binds to the active site of the HisC, thereby preventing its activation by native substrate, which might be responsible for its antibacterial and antibiofilm activity. Since the high MIC of Heraclenol is not achievable clinically in human tissues, further chemical modifications will be required to lower the drug's MIC value and increase its potency. Alternatively, its synergistic action with other antimicrobials may also be studied.
New coumarin from the roots of Prangos pabularia
Nat Prod Res 2018 Oct;32(19):2325-2332.PMID:29224384DOI:10.1080/14786419.2017.1413558.
The new coumarin 1, yuganin A (7-methoxy-8-((1S,2S)-1,2,3-trihydroxy-3-methylbutyl)-2H-chromen-2-one) along with nine known coumarins, Heraclenol 3'-O-β-D-glucopyranoside (2), oxypeucedanin hydrate 3'-O-β-D-glucopyranoside (3), Heraclenol (4), oxypeucedanin hydrate (5), osthole (6), oxypeucedanin (7), heraclenin (8), isoimperatorin (9), imperatorin (10) and the disaccharide sucrose (11), have been isolated from the roots of Prangos pabularia, and the structures of these isolated compounds were elucidated by spectroscopic means, especially, UV, HR-ESIMS, and 1D and 2D NMR spectroscopy. Furthermore, the anti-melanogenic effect of yuganin A and its inhibitory effect on B16 cells were evaluated. Yuganin A may be useful in the treatment of hyperpigmentation and as a skin-whitening agent in the cosmetics industry.
Retrieval of High Added Value Natural Bioactive Coumarins from Mandarin Juice-Making Industrial Byproduct
Molecules 2021 Dec 12;26(24):7527.PMID:34946609DOI:10.3390/molecules26247527.
Cold pressed essential oil (CPEO) of mandarin (Citrus reticulata Blanco), a by-product of the juice-making industrial process known to contain large amounts of polymethoxyflavones, was exploited for its content in high added value natural coumarins. The study herein afforded a method referring to the evaporation of CPEO volatile fraction under mild conditions (reduced pressure and temperature below 35 °C) as azeotrope with isopropanol. This allowed the isolation of high added value coumarins from the non-volatile fragment using preparative High Performance Liquid Chromatography (HPLC). Pilot-scale application of this procedure afforded for each kg of CPEO processed the following natural bioactive coumarins in chemically pure forms: Heraclenol (38-55 mg), 8-gerayloxypsoralen (35-51 mg), auraptene (22-33 mg), and bergamottin (14-19 mg). The structures of coumarins were verified by Nuclear Magnetic Resonance (NMR) spectroscopy and HPLC co-injection with authentic standards. Thus, the low market value mandarin CPEO with current value of 17 to 22 EUR/kg can be valorized through the production of four highly bioactive natural compounds worth 3479 to 5057 EUR/kg, indicating the great potentials of this methodology in the terms of the circular economy.
Triterpene and coumarins from Skimmia laureola
Nat Prod Lett 2002 Oct;16(5):305-13.PMID:12434985DOI:10.1080/10575630290020613.
In the course of our studies on the chemical constituents of the leaves of Skimmia laureola, a new triterpene O-methyl cyclolaudenol (1) and a new coumarin, (+)-7-methoxy-6-(2'R-methoxy-3'-hydroxy-3'-methyl butyl) coumarin (2) were isolated. In addition five known coumarins, isogospherol (3), Heraclenol (4), 5,8-dimethoxy coumarin-2H-1-benzopyran-2-one (5), 7-methoxy-6[2'-oxo-3'-methyl butyl] coumarin (6), and (+)-ulopterol (7) were also isolated for the first time from this plant. The structures were identified by spectroscopic studies and the stereochemistry at C-2' in compounds 3 and 4 were established by Horeau's procedure.
Coumarins from Angelica lucida L.--antibacterial activities
Molecules 2009 Jul 27;14(8):2729-34.PMID:19701119DOI:10.3390/molecules14082729.
The first phytochemical investigation of the fruits of Angelica lucida has led to the isolation and characterization of five known coumarins (imperatorin, isoimperatorin, Heraclenol, oxypeucedanin hydrate and heraclenin). All isolated compounds were identified by means of spectral and literature data. The extracts and the isolated constituents from A. lucida have been also evaluated for their antimicrobial activity against six Gram positive and negative bacteria, two oral pathogens and three human pathogenic fungi, exhibiting an interesting antimicrobial profile.