trans-Nerolidol
(Synonyms: 反式-橙花叔醇) 目录号 : GC48193
A sesquiterpene with diverse biological activities
Cas No.:40716-66-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
trans-Nerolidol is a sesquiterpene that has been found in various plants, including C. sativa, and has diverse biological activities, including antimicrobial, antioxidant, anticancer, and insecticidal properties.1,2,3,4 In a disc assay, trans-nerolidol inhibits the growth of S. aureus, B. subtilis, E. coli, and S. cerevisiae with zones of inhibition measuring 10, 9, 10, and 4 mm, respectively.2 It reduces viability of CaCo-2 adenocarcinoma cells with an IC50 value of 28.7 mg/L and reduces production of reactive oxygen species (ROS).3 trans-Nerolidol is insecticidal against A. aegypti larvae with a 24-hour LC50 value of 9 mg/L.4
1.Nissen, L., Zatta, A., Stefanini, I., et al.Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.)Fitoterapia81(5)413-419(2010) 2.Skaltsa, H.D., Lazari, D.M., Mavromati, A.S., et al.Composition and antimicrobial activity of the essential oil of Scutellaria albida ssp. albida from GreecePlanta Med.66(7)672-674(2000) 3.Ambro?, M., BoušovÁ, I., Skarka, A., et al.The influence of sesquiterpenes from Myrica rubra on the antiproliferative and pro-oxidative effects of doxorubicin and its accumulation in cancer cellsMolecules20(8)15343-15358(2015) 4.Chantraine, J.-M., Laurent, D., Ballivian, C., et al.Insecticidal activity of essential oils on Aedes aegypti larvaePhytother. Res.12(5)350-354(1998)
| Cas No. | 40716-66-3 | SDF | |
| 别名 | 反式-橙花叔醇 | ||
| Canonical SMILES | C=CC(O)(C)CC/C=C(C)/CC/C=C(C)/C | ||
| 分子式 | C15H26O | 分子量 | 222.4 |
| 溶解度 | DMF: miscible,DMSO: miscible,Ethanol: miscible,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/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 | 4.4964 mL | 22.482 mL | 44.964 mL |
| 5 mM | 0.8993 mL | 4.4964 mL | 8.9928 mL |
| 10 mM | 0.4496 mL | 2.2482 mL | 4.4964 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。
Enhancing trans-Nerolidol Productivity in Yarrowia lipolytica by Improving Precursor Supply and Optimizing Nerolidol Synthase Activity
J Agric Food Chem 2022 Dec 7;70(48):15157-15165.PMID:36444843DOI:10.1021/acs.jafc.2c05847.
The low enzymatic capability of terpene synthases and the limited availability of precursors often hinder the productivity of terpenes in microbial hosts. Herein, a systematic approach combining protein engineering and pathway compartmentation was exploited in Yarrowia lipolytica for the high-efficient production of trans-Nerolidol, a sesquiterpene with various commercial applications. Through the single-gene overexpression, the reaction catalyzed by nerolidol synthase (FaNES1) was identified as another rate-limiting step. An optimized FaNES1G498Q was then designed by rational protein engineering using homology modeling and docking studies. Additionally, further improvement of trans-Nerolidol production was observed as enhancing the expression of an endogenous carnitine acetyltransferase (CAT2) putatively responsible for acetyl-CoA shuttling between peroxisome and cytosol. To harness the peroxisomal acetyl-CoA pool, a parallel peroxisomal pathway starting with acetyl-CoA to trans-Nerolidol was engineered. Finally, the highest reported titer of 11.1 g/L trans-Nerolidol in the Y. lipolytica platform was achieved in 5 L fed-batch fermentation with the carbon restriction approach.
Characterization of trans-Nerolidol Synthase from Celastrus angulatus Maxim and Production of trans-Nerolidol in Engineered Saccharomyces cerevisiae
J Agric Food Chem 2021 Feb 24;69(7):2236-2244.PMID:33586967DOI:10.1021/acs.jafc.0c06084.
Volatile terpenoids are a large group of important secondary metabolites and possess many biological activities. The acyclic sesquiterpene trans-Nerolidol is one of the typical representatives and widely used in cosmetics and agriculture. Here, the accumulation of volatile terpenes in different tissues of Celastrus angulatus was investigated, and two trans-Nerolidol synthases, CaNES1 and CaNES2, were identified and characterized by in vitro enzymatic assays. Both genes are differentially transcribed in different tissues of C. angulatus. Next, we constructed a Saccharomyces cerevisiae cell factory to enable high-level production of trans-Nerolidol. Glucose was the sole carbon source to sequentially control gene expression between the competitive squalene and trans-Nerolidol pathways. Finally, the trans-Nerolidol production of recombinant strain LWG003-CaNES2 was 7.01 g/L by fed-batch fermentation in a 5 L bioreactor. The results clarify volatile terpenoid biosynthesis in C. angulatus and provide a promising potential for industrial production of trans-Nerolidol in S. cerevisiae.
High-Yield Biosynthesis of trans-Nerolidol from Sugar and Glycerol
J Agric Food Chem 2023 May 6.PMID:37148252DOI:10.1021/acs.jafc.3c01161.
Isoprenoids, or terpenoids, have wide applications in food, feed, pharmaceutical, and cosmetic industries. Nerolidol, an acyclic C15 isoprenoid, is widely used in cosmetics, food, and personal care products. Current supply of nerolidol is mainly from plant extraction that is inefficient, costly, and of inconsistent quality. Here, we screened various nerolidol synthases from bacteria, fungi, and plants and found that the strawberry nerolidol synthase was most active in Escherichia coli. Through systematic optimization of the biosynthetic pathways, carbon sources, inducer, and genome editing, we constructed a series of deletion strains (single mutants ΔldhA, ΔpoxB, ΔpflB, and ΔtnaA; double mutants ΔadhE-ΔldhA; and triple mutants and beyond ΔadhE-ΔldhA-ΔpflB and ΔadhE-ΔldhA-ΔackA-pta) that produced high yields of 100% trans-Nerolidol. In flasks, the highest nerolidol titers were 1.8 and 3.3 g/L in glucose-only and glucose-lactose-glycerol media, respectively. The highest yield reached 26.2% (g/g), >90% of the theoretic yield. In two-phase extractive fed-batch fermentation, our strain produced ∼16 g/L nerolidol within 4 days with about 9% carbon yield (g/g). In a single-phase fed-batch fermentation, the strain produced >6.8 g/L nerolidol in 3 days. To the best of our knowledge, our titers and productivity are the highest in the literature, paving the way for future commercialization and inspiring biosynthesis of other isoprenoids.
beta-caryophyllene oxide and trans-Nerolidol affect enzyme activity of CYP3A4 - in vitro and in silico studies
Physiol Res 2019 Nov 22;68(Suppl 1):S51-S58.PMID:31755290DOI:10.33549/physiolres.934323.
Evaluation of possible interactions with enzymes of drug metabolism is an important part of studies on safety and, in general, on the properties of any drug or biologically active compound. Here, focus is given on interactions of three sesquiterpenes (beta-caryophyllene oxide (CAO), trans-Nerolidol (tNER) and farnesol (FAR)) with CYP3A4. To determine the CYP3A4 activity, specific substrates testosterone (TES) and midazolam (MDZ) were used. In human liver microsomes, the CAO inhibited the MDZ 1´-hydroxylation by mixed type inhibition and K(i) 46.6 microM; TES 6beta-hydroxylation was inhibited more strongly by tNER by the same mechanism and with K(i) of 32.5 microM. Results indicated a possibility of different mode of interaction of both compounds within the active site of CYP3A4 and this was why the molecular docking study was done. The docking experiments showed that the studied sesquiterpenes (CAO and tNER) bound to the CYP3A4 active site cause a significant decrease of binding affinity of substrates tested which corresponded well to the inhibition studies. The inhibition observed, however, most probably does not pose a real harm to microsomal drug metabolism as the levels of sesquiterpenes in plasma (assuming the use of these compounds as spices or flavoring additives) does not usually exceed micromolar range. Hence, the interaction of drugs metabolized by CYP3A4 with sesquiterpenes is less probable.
The impact of sesquiterpenes β-caryophyllene oxide and trans-Nerolidol on xenobiotic-metabolizing enzymes in mice in vivo
Xenobiotica 2018 Nov;48(11):1089-1097.PMID:29098926DOI:10.1080/00498254.2017.1398359.
1. Sesquiterpenes, constituents of plant essential oil, are popular bioactive compounds due to the positive effect on human health, but their potential toxicity and possible herb-drug interactions are often omitted. In our in vivo study, we followed up the effect of p.o. administration of two sesquiterpenes β-caryophyllene oxide (CAO) and trans-Nerolidol (NER) on various xenobiotic-metabolizing enzymes in mice liver and small intestine. 2. To spot the early effect of studied compounds, enzymatic activity and mRNA levels were assessed 6 and 24 h after single dose. 3. CAO and NER markedly increased cytochromes P450 (CYP2B, 3A, 2C) activity and mRNA levels in both tissues. Liver also showed elevated activity of aldo-ketoreductase 1C and carbonyl reductase after treatment. Contrary, sesquiterpenes decreased NAD(P)H:quinone oxidoreductase 1 activity in small intestine. Among conjugation enzymes, only liver sulfotransferase activity was increased by sesquiterpenes. 4. Our results document that single dose of sesquiterpenes modulate activities and expression of several xenobiotic-metabolizing enzymes.