Secoxyloganin
(Synonyms: 断氧化马钱苷) 目录号 : GC39145
A secoiridoid glycoside with diverse biological activities
Cas No.:58822-47-2
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
Secoxyloganin is a secoiridoid glycoside that has been found in L. japonica and has diverse biological activities.1,2,3 It is active against E. coli and S. aureus in a disc assay when used at a concentration of 2 mg/disc.1 Secoxyloganin is cytotoxic to human dermal fibroblasts (IC50 = 78.1 ?M).2 In vivo, secoxyloganin (10 mg/ml) prevents hen egg white lysozyme-induced decreases in tail vein blood flow, a marker of allergic inflammation, in hen egg white lysozyme-sensitized mice.3
1.Xiong, J., Li, S., Wang, W., et al.Screening and identification of the antibacterial bioactive compounds from Lonicera japonica Thunb. leavesFood Chem.138(1)327-333(2013) 2.Zebiri, I., Haddad, M., Duca, L., et al.Biological activities of triterpenoids from Poraqueiba sericea stemsNat. Prod. Res.31(11)1333-1338(2017) 3.Oku, H., Ogawa, Y., Iwaoka, E., et al.Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonicaBiol. Pharm. Bull.34(8)1330-1333(2011)
| Cas No. | 58822-47-2 | SDF | |
| 别名 | 断氧化马钱苷 | ||
| Canonical SMILES | C=C[C@@H]1[C@@H](C(C(OC)=O)=CO[C@@]1([H])O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)CC(O)=O | ||
| 分子式 | C17H24O11 | 分子量 | 404.37 |
| 溶解度 | DMF: 5mg/mL,DMSO: 5mg/mL,Ethanol: 10mg/mL,PBS (pH 7.2): 10mg/mL | 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。 |
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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 | 2.473 mL | 12.3649 mL | 24.7298 mL |
| 5 mM | 0.4946 mL | 2.473 mL | 4.946 mL |
| 10 mM | 0.2473 mL | 1.2365 mL | 2.473 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。
Characterization of a second secologanin synthase isoform producing both secologanin and Secoxyloganin allows enhanced de novo assembly of a Catharanthus roseus transcriptome
BMC Genomics 2015 Aug 19;16(1):619.PMID:26285573DOI:10.1186/s12864-015-1678-y.
Background: Transcriptome sequencing offers a great resource for the study of non-model plants such as Catharanthus roseus, which produces valuable monoterpenoid indole alkaloids (MIAs) via a complex biosynthetic pathway whose characterization is still undergoing. Transcriptome databases dedicated to this plant were recently developed by several consortia to uncover new biosynthetic genes. However, the identification of missing steps in MIA biosynthesis based on these large datasets may be limited by the erroneous assembly of close transcripts and isoforms, even with the multiple available transcriptomes. Results: Secologanin synthases (SLS) are P450 enzymes that catalyze an unusual ring-opening reaction of loganin in the biosynthesis of the MIA precursor secologanin. We report here the identification and characterization in C. roseus of a new isoform of SLS, SLS2, sharing 97 % nucleotide sequence identity with the previously characterized SLS1. We also discovered that both isoforms further oxidize secologanin into Secoxyloganin. SLS2 had however a different expression profile, being the major isoform in aerial organs that constitute the main site of MIA accumulation. Unfortunately, we were unable to find a current C. roseus transcriptome database containing simultaneously well reconstructed sequences of SLS isoforms and accurate expression levels. After a pair of close mRNA encoding tabersonine 16-hydroxylase (T16H1 and T16H2), this is the second example of improperly assembled transcripts from the MIA pathway in the public transcriptome databases. To construct a more complete transcriptome resource for C. roseus, we re-processed previously published transcriptome data by combining new single assemblies. Care was particularly taken during clustering and filtering steps to remove redundant contigs but not transcripts encoding potential isoforms by monitoring quality reconstruction of MIA genes and specific SLS and T16H isoforms. The new consensus transcriptome allowed a precise estimation of abundance of SLS and T16H isoforms, similar to qPCR measurements. Conclusions: The C. roseus consensus transcriptome can now be used for characterization of new genes of the MIA pathway. Furthermore, additional isoforms of genes encoding distinct MIA biosynthetic enzymes isoforms could be predicted suggesting the existence of a higher level of complexity in the synthesis of MIA, raising the question of the evolutionary events behind what seems like redundancy.
A new secoiridoid glucoside from Olea europaea
J Asian Nat Prod Res 2022 Nov;24(11):1093-1100.PMID:35137662DOI:10.1080/10286020.2021.2017898.
A new phenolic glucoside (1), olerikaside, and other known secoiridoid glucosides [oleuropein (2), demethyl oleuropein (3), oleoside 11-methyl ester (4), oleoside 7, 11-dimethyl ester (5), 7-β-D-glucopyranosyl 11-methyl oleoside (6), Secoxyloganin (7), ilicifolioside B (8), hydroxytyrosol (9), and hydroxytyrosol glucosides (10-12)] were isolated from unprocessed olive fruits of Olea europaea cv. "Lucca". The chemical structure of olerikaside (1) was clarified based on spectroscopy and chemical analysis data.
Iridoids from Loasa acerifolia
Phytochemistry 1998 Sep;49(1):131-5.PMID:9745765DOI:10.1016/s0031-9422(97)01000-5.
In the course of preliminary chemotaxonomic studies on Loasaceae from South and Central America, 30 species from 6 genera were screened by chromatographic means. From the aerial parts of Loasa acerifolia Dombey, the novel trimeric and dimeric iridoid glucosides acerifolioside and tricoloroside methyl ester, consisting of loganin and Secoxyloganin moieties, were isolated. The structures were primarily elucidated by NMR spectroscopy. Loganin, loganic acid, rutin, scopoletin and chlorogenic acid were identified by cochromatography with reference compounds.
Further iridoid glucosides in the genus Manulea (Scrophulariaceae)
Phytochemistry 2015 Jan;109:43-8.PMID:25457503DOI:10.1016/j.phytochem.2014.10.004.
From Manulea altissima (Scrophulariaceae) were isolated five known secoiridoid glucosides sweroside, eustomoside, eustoside, Secoxyloganin and secologanoside as well as the 4″-O-rhamnopyranosyl-feruloyl ester of adoxosidic acid, named altissimoside. Also, the caffeoyl phenylethanoid glycoside verbascoside was isolated. In addition two previously unknown terpenoid esters of 6β-hydroxy 8-epi-boschnaloside, named manucoside A and B were isolated from a formerly obtained fraction from the work-up of Manulea corymbosa. The distribution of iridoid glucosides in the Scrophulariaceae is discussed.
Acute toxicity, antiedematogenic activity, and chemical constituents of Palicourea rigida Kunth
Z Naturforsch C J Biosci 2016 Mar;71(3-4):39-43.PMID:26927220DOI:10.1515/znc-2015-0036.
The phytochemical study of the leaves, roots, and flowers of Palicourea rigida led to the isolation of the triterpenes betulinic acid (1) and lupeol (2), the diterpene phytol (3), and the iridoid glycosides sweroside (4) and Secoxyloganin (5). These compounds were identified using NMR 1H and 13C and comparing the spectra with published data. We studied the antiedematogenic activity of crude extracts from the organs, and of different fractions, in mice and found that the n-hexane fraction of the leaf extract significantly inhibited the ear edema resulting from croton oil administration. The crude extract from leaves was not acutely toxic to the mice.