Solanesol
(Synonyms: 茄尼醇) 目录号 : GC48086
A trisesquiterpenoid with diverse biological activities
Cas No.:13190-97-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Solanesol is a trisesquiterpenoid that has been found in N. tabacum and has diverse biological activities.1,2,3 It is active against E. coli, M. phlei, P. aeruginosa, and S. aureus.1 Solanesol (40 µM) increases basal heme oxygenase-1 (HO-1) and nuclear factor erythroid 2-related factor 2 (Nrf2) activities and inhibits LPS-induced production of IL-6, IL-1β, and TNF-α in RAW 264.7 cells.2 It reduces escape latency in the Morris water maze and the number of slips in a beam-crossing task in a rat model of Huntington's disease induced by 3-nitropropionic acid when administered at doses of 5, 10, and 15 mg/kg.3 Solanesol is also a precursor in the formation of polynuclear aromatic hydrocarbons (PAHs), which are carcinogenic components of tobacco smoke, and has been used as a synthetic intermediate in the synthesis of coenzyme Q10 and vitamin K analogs that have antioxidant activities.1
1.Yan, N., Liu, Y., Liu, L., et al.Bioactivities and medicinal value of solanesol and its accumulation, extraction technology, and determination methodsBiomolecules9(8)334(2019) 2.Yao, X., Lu, B., LÜ, C., et al.Solanesol induces the expression of heme oxygenase-1 via p38 and Akt and suppresses the production of proinflammatory cytokines in RAW264.7 cellsFood Funct.8(1)132-141(2017) 3.Mehan, S., Monga, V., Rani, M., et al.Neuroprotective effect of solanesol against 3-nitropropionic acid-induced Huntington's disease-like behavioral, biochemical, and cellular alterations: Restoration of coenzyme-Q10-mediated mitochondrial dysfunctionIndian J. Pharmacol.50(6)309-319(2018)
| Cas No. | 13190-97-1 | SDF | |
| 别名 | 茄尼醇 | ||
| Canonical SMILES | OC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C | ||
| 分子式 | C45H74O | 分子量 | 631.1 |
| 溶解度 | Ethanol: 0.25mg/mL | 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 | 1.5845 mL | 7.9227 mL | 15.8453 mL |
| 5 mM | 0.3169 mL | 1.5845 mL | 3.1691 mL |
| 10 mM | 0.1585 mL | 0.7923 mL | 1.5845 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。
Solanesol Biosynthesis in Plants
Molecules 2017 Mar 23;22(4):510.PMID:28333111DOI:10.3390/molecules22040510.
Solanesol is a non-cyclic terpene alcohol composed of nine isoprene units that mainly accumulates in solanaceous plants. Solanesol plays an important role in the interactions between plants and environmental factors such as pathogen infections and moderate-to-high temperatures. Additionally, it is a key intermediate for the pharmaceutical synthesis of ubiquinone-based drugs such as coenzyme Q10 and vitamin K2, and anti-cancer agent synergizers such as N-solanesyl-N,N'-bis(3,4-dimethoxybenzyl) ethylenediamine (SDB). In plants, Solanesol is formed by the 2-C-methyl-d-erythritol 4-phosphate (MEP) pathway within plastids. Solanesol's biosynthetic pathway involves the generation of C5 precursors, followed by the generation of direct precursors, and then the biosynthesis and modification of terpenoids; the first two stages of this pathway are well understood. Based on the current understanding of Solanesol biosynthesis, we here review the key enzymes involved, including 1-deoxy-d-xylulose 5-phosphate synthase (DXS), 1-deoxy-d-xylulose 5-phosphate reductoisomerase (DXR), isopentenyl diphosphate isomerase (IPI), geranyl geranyl diphosphate synthase (GGPPS), and solanesyl diphosphate synthase (SPS), as well as their biological functions. Notably, studies on microbial heterologous expression and overexpression of key enzymatic genes in tobacco Solanesol biosynthesis are of significant importance for medical uses of tobacco.
Bioactivities and Medicinal Value of Solanesol and Its Accumulation, Extraction Technology, and Determination Methods
Biomolecules 2019 Aug 2;9(8):334.PMID:31382471DOI:10.3390/biom9080334.
Solanesol, an aliphatic terpene alcohol composed of nine isoprene units, is mainly found in solanaceous plants. Particularly, tobacco (Nicotiana tabacum), belonging to the Solanaceae family, is the richest plant source of Solanesol, and its leaves have been regarded as the ideal material for Solanesol extraction. Since the discovery of Solanesol in tobacco, significant progress has been achieved in research on Solanesol's bioactivities, medicinal value, accumulation, extraction technology, and determination methods. Solanesol possesses strong free radical absorption ability and antioxidant activity owing to the presence of several non-conjugated double bonds. Notably, Solanesol's anti-inflammatory, neuroprotective, and antimicrobial activities have been previously demonstrated. Solanesol is a key intermediate in the synthesis of coenzyme Q10, vitamin K2, and the anticancer agent synergiser N-solanesyl-N,N'-bis(3,4-dimethoxybenzyl) ethylenediamine. Other applications of Solanesol include Solanesol derivative micelles for hydrophobic drug delivery, solanesol-derived scaffolds for bioactive peptide multimerization, and solanesol-anchored DNA for mediating vesicle fusion. Solanesol accumulation in plants is influenced by genetic and environmental factors, including biotic stresses caused by pathogen infections, temperature, illumination, and agronomic measures. Seven extraction technologies and seven determination methods of Solanesol are also systematically summarized in the present review. This review can serve as a reference for Solanesol's comprehensive application.
Solanesol: added value from Solanaceous waste
Phytochemistry 2011 Aug;72(11-12):1323-7.PMID:21459392DOI:10.1016/j.phytochem.2011.03.015.
Isoprenoids, also known as terpenoids, are the largest and oldest class of natural products known. They are comprised of more than 40,000 different molecules all biosynthetically related via a common five carbon building block (isopentenyl). Many isoprenoids are of commercial interest and are used as fragrances in cosmetics and flavours, colorants and nutritional supplements in foods and feeds as well as being phytomedicines. Their industrial relevance also means they are compounds of high value with global markets in the range of $1 billion per annum. Solanesol is a 45-carbon, unsaturated, all-trans-nonaprenol isoprenoid of high value. Recently this molecule has received particular attention because of its utility, both in its own right and as a precursor in the production of numerous compounds used in the treatment of disease states. Instability in supply and spiralling costs have also lead to the search for sources. In this article existing sources and the potential strategies and tools available to create sustainable biosources are reviewed.
Determination of Free Solanesol Levels in Cigarette Filters by Liquid Chromatography-Mass Spectrometry
J Anal Toxicol 2022 May 20;46(5):549-558.PMID:33860788DOI:10.1093/jat/bkab041.
Solanesol, a naturally occurring constituent of tobacco, has been utilized as a good marker for environmental tobacco smoke particulate and as a noninvasive predictor of mainstream cigarette smoke tar and nicotine intake under naturalistic smoking conditions. A fast and accurate method for measuring free Solanesol to assess tobacco smoke exposure is highly desirable. We have developed and validated a new environmentally friendly, high-throughput method for measuring Solanesol content in discarded cigarette filter butts. The Solanesol deposited in the used filters can be correlated with mainstream smoke deliveries of nicotine and total particle matter to estimate constituent delivery to smokers. A portion of filter material is removed from cigarette butts after machine smoking, spiked with internal standard solution, extracted and quantitatively analyzed using reverse-phase liquid chromatography coupled to a triple-quadrupole mass spectrometer. The new method incorporates a 48-well plate format for automated sample preparation that reduces sample preparation time and solvent use and increases sample throughput 10-fold compared to our previous method. Accuracy and precision were evaluated by spiking known amounts of Solanesol on both clean and smoked cigarette butts. Recoveries exceeded 93% at both low and high spiking levels. Linear Solanesol calibration curves ranged from 1.9 to 367 µg/butt with a 0.05 µg/butt limit of detection.
Solanesol derived therapeutic carriers for anticancer drug delivery
Int J Pharm 2019 Dec 15;572:118823.PMID:31715346DOI:10.1016/j.ijpharm.2019.118823.
Metabolites of a large number of inert drug carriers can cause long-term exogenous biological toxicity. Therefore, carriers with simultaneous therapeutic effects may be a good choice for drug delivery. Herein, a series of pharmacologically active Solanesol derivatives were synthesized and investigated for use as micellar drug carriers for cancer therapy. Solanesyl thiosalicylic acid (STS) was first synthesized by introducing a thiosalicylic acid group to Solanesol, inspired by the characteristic structure of farnesyl thiosalicylic acid (FTS) which is a non-toxic inhibitor of all active forms of the RAS protein. Then, two amphiphilic derivatives of STS were formed with ester- and hydrazone (HZ)-bond linked methyl poly(ethylene glycol)(mPEG), mPEG-STS and mPEG-HZ-STS, respectively. The PEGylated STS could be formed stable nano-sized micelles loaded with Doxorubicin (DOX). In vitro, DOX loaded mPEG-STS and mPEG-HZ-STS micelles exhibited stronger tumor inhibition ability compared with free DOX. In vivo, blank mPEG-STS and mPEG-HZ-STS micelles showed an obvious inhibiting effect on tumor growth while the drug loaded micelles had the greatest tumor inhibition effect. The enhanced therapeutic effects and the synergistic effect observed with this solanesol-based drug delivery system could be attributed to the inherent therapeutic qualities of the drug carriers.