Noreugenin
(Synonyms: 去甲丁香色原酮) 目录号 : GC36760
Noreugenin，是一种色酮，源于 Hymenocallis littoralis Salisb (石蒜科)。
Cas No.:1013-69-0
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
Noreugenin, 5,7-dihydroxy-2-methyl-4H-chromen-4-one, is a new chromone from Hymenocallis littoralis Salisb. (Amaryllidaceae)[1].
[1]. Wang Y, et al. Aspergchromones A and B, two new polyketides from the marine sponge-associated fungus Aspergillus sp. SCSIO XWS03F03. J Asian Nat Prod Res. 2017 Jul;19(7):684-690.
| Cas No. | 1013-69-0 | SDF | |
| 别名 | 去甲丁香色原酮 | ||
| Canonical SMILES | O=C1C2=C(O)C=C(O)C=C2OC(C)=C1 | ||
| 分子式 | C10H8O4 | 分子量 | 192.17 |
| 溶解度 | DMSO: 250 mg/mL (1300.93 mM); Water: < 0.1 mg/mL (insoluble) | 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 | 5.2037 mL | 26.0186 mL | 52.0373 mL |
| 5 mM | 1.0407 mL | 5.2037 mL | 10.4075 mL |
| 10 mM | 0.5204 mL | 2.6019 mL | 5.2037 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。
Tailoring Corynebacterium glutamicum towards increased malonyl-CoA availability for efficient synthesis of the plant pentaketide Noreugenin
Microb Cell Fact 2019 Apr 11;18(1):71.PMID:30975146DOI:10.1186/s12934-019-1117-x.
Background: In the last years, different biotechnologically relevant microorganisms have been engineered for the synthesis of plant polyphenols such as flavonoids and stilbenes. However, low intracellular availability of malonyl-CoA as essential precursor for most plant polyphenols of interest is regarded as the decisive bottleneck preventing high product titers. Results: In this study, Corynebacterium glutamicum, which emerged as promising cell factory for plant polyphenol production, was tailored by rational metabolic engineering towards providing significantly more malonyl-CoA for product synthesis. This was achieved by improving carbon source uptake, transcriptional deregulation of accBC and accD1 encoding the two subunits of the acetyl-CoA carboxylase (ACC), reduced flux into the tricarboxylic acid (TCA) cycle, and elimination of anaplerotic carboxylation of pyruvate. The constructed strains were used for the synthesis of the pharmacologically interesting plant pentaketide Noreugenin, which is produced by plants such as Aloe arborescens from five molecules of malonyl-CoA. In this context, accumulation of the C1/C6 cyclized intermediate 1-(2,4,6-trihydroxyphenyl)butane-1,3-dione (TPBD) was observed, which could be fully cyclized to the bicyclic product Noreugenin by acidification. Conclusion: The best strain C. glutamicum Nor2 C5 mufasOBCD1 PO6-iolT1 ∆pyc allowed for synthesis of 53.32 mg/L (0.278 mM) Noreugenin in CGXII medium supplemented with casamino acids within 24 h.
Two new nor-lignans, siamensinols A and B, from Selaginella siamensis Hieron. and their biological activities
Nat Prod Res 2022 Nov;36(21):5591-5599.PMID:34963379DOI:10.1080/14786419.2021.2022664.
Two new nor-lignans siamensinols A-B (1-2) and seven known compounds agatharesinol (3), syringaresinol-glucoside (4), Noreugenin (5), 8-methyleugenitol (6), melachromone (7), uncinoside A (8) and daucosterol (9) were isolated from Selaginella siamensis Hieron. The structures of the new compounds were elucidated on the basis of comprehensive spectroscopic methods, including 1 D, 2 D-NMR, HR-ESI-MS and CD spectrometry. Compounds 1-2 showed moderate inhibitory effect on MOLT-3 cells while 8-methyleugenitol (6) exhibited moderate inhibitory effect on three tumor cells (HepG2, A549 and HuCCA-1). Compounds 2-3 showed the potent cancer chemoprevention in DPPH, XXO, IXO and AIA assays.
Evaluation of leishmanicidal and trypanocidal activities of phenolic compounds from Calea uniflora Less
Nat Prod Res 2016;30(5):551-7.PMID:25880257DOI:10.1080/14786419.2015.1030740.
The phytochemical study of Calea uniflora led to the isolation of nine phenolic compounds identified as Noreugenin (1), ethyl caffeate (2), a mixture of butein (3) + orobol (4), α-hydroxy-butein (5), caffeic acid (6), butein 4'-O-glucopyranosyl (7), quercetin 3-O-glucopyranosyl (8) and 3,5-di-O-caffeoylquinic acid (9). The chemical identity of the isolates was established on the basis of NMR and physical data. The chemical shifts of 5 and 7 have been reassigned and all the isolates were tested against Leishmania amazonensis and Trypanosoma cruzi amastigotes. None of the metabolites showed promising leishmanicidal activity. However, 2 and the mixture of 3 and 4 demonstrated interesting trypanocidal effect with IC50 values of 18.27 and 26.53 μM, respectively. Besides, these compounds did not present cytotoxic effect towards THP-1 cells, and compound 2 was 3.5-fold more selective than the mixture of 3+4.
Volatiles from the Mandibular Gland Reservoir Content of Colobopsis explodens Laciny and Zettel, 2018, Worker Ants (Hymenoptera: Formicidae)
Molecules 2019 Sep 24;24(19):3468.PMID:31554296DOI:10.3390/molecules24193468.
Forty-five volatile organic compounds (VOCs) were identified or annotated in the mandibular gland reservoir content (MGRC) of the Southeast Asian ant Colobopsis explodens Laciny and Zettel, 2018 (Hymenoptera: Formicidae), using headspace solid-phase microextraction (HS-SPME) coupled to gas chromatography mass spectrometry (GC-MS) and liquid extraction combined with GC-MS. In extension of previous reports on VOCs of C. explodens, members of different compound classes, such as alkanes, aliphatic and aromatic carboxylic acids, and phenolics, were detected. The ketone 2-heptanone and the biochemically related phenolics benzene-1,3,5-triol (phloroglucinol, PG), 1-(2,4,6-trihydroxyphenyl)ethanone (monoacetylphloroglucinol, MAPG), 5,7-dihydroxy-2-methylchromen-4-one (Noreugenin), and 1-(3-Acetyl-2,4,6-trihydroxyphenyl)ethanone (2,4-diacetylphloroglucinol, DAPG) dominated the GC-MS chromatograms. The identities of the main phenolics MAPG and Noreugenin were further verified by liquid chromatography-high resolution-tandem mass spectrometry (LC-HRMS/MS). A comparative study of MGRC samples originating from three distinct field expeditions revealed differences in the VOC profiles, but the presence and relative abundances of the dominating constituents were largely consistent in all samples. Our study considerably extends the knowledge about the number and type of VOCs occurring in the MGRC of C. explodens. Based on the type of the detected compounds, we propose that the likely irritant and antibiotic phenolic constituents play a role in defense against arthropod opponents or in protection against microbial pathogens.
New phytoconstituents, anti-microbial and cytotoxic activities of Acacia etbaica Schweinf
Nat Prod Res 2021 Dec;35(24):5571-5580.PMID:32700973DOI:10.1080/14786419.2020.1797725.
Acacia etbaica is wild plant growing in the desert of Egypt, and it has folkloric medicinal uses. Phytochemical investigation of Acacia etbaica extracts led to the isolation and identification of seven compounds. Among these compounds are three new simple phenolics: Resacetophenone-6-methyl [1], Resorcinol [2], Resorcinol-O- β -Glucoside [3]; phenolic ester; and other four known compounds: Methylparaben [4]; two chromones, Noreugenin [5], Eugenin [6]; and one cyclitol: pinitol [7]. Compounds [1-3] isolated and identified for the first time from natural origin. In contrast, compounds [4-6] isolated for the first time from the family Fabaceae. The biological investigation was conducted on plant extracts and showed that the methylene chloride extract had a strong efficacy against Bacillus subtilis and good activity against Candida albicans. In contrast, the n-butanol extract showed extreme cytotoxic activity against Mammary gland breast cancer (MCF-7), and strong activity against Hepatocellular carcinoma (HEPG-2), and Colorectal carcinoma (HCT-116) cell lines.