Orchinol
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| Category | Antibiotics |
| Catalog number | BBF-02152 |
| CAS | 41060-20-2 |
| Molecular Weight | 256.30 |
| Molecular Formula | C16H16O3 |
| Purity | >98% |
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Description
Orchinol is an aromatic derivative of antibiotic originally isolated from Rhizoctonia repens and has antifungal activity.
Specification
| Synonyms | 9,10-Dihydro-5,7-dimethoxyphenanthren-2-ol |
| IUPAC Name | 5,7-dimethoxy-9,10-dihydrophenanthren-2-ol |
| Canonical SMILES | COC1=CC2=C(C3=C(CC2)C=C(C=C3)O)C(=C1)OC |
| InChI | InChI=1S/C16H16O3/c1-18-13-8-11-4-3-10-7-12(17)5-6-14(10)16(11)15(9-13)19-2/h5-9,17H,3-4H2,1-2H3 |
| InChI Key | HOVUVTNDNLNINP-UHFFFAOYSA-N |
Properties
| Appearance | Achromatic Diamond Crystal |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 467.8±45.0°C at 760 mmHg |
| Melting Point | 127°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. [Effects of orchinol on invasion, migration and Wnt3a/β-catenin signaling pathway of human gastric cancer SGC-7901 cells]
Tao Ling, Wei Wang, Chen Hu, Xin Yan, Yu-Ting Xu, Chun Tang, Yu Kou, Liang Liu Zhongguo Zhong Yao Za Zhi. 2018 Dec;43(23):4718-4723. doi: 10.19540/j.cnki.cjcmm.20180710.001.
The purpose of this study was to investigate the inhibitory effect of the main 9,10-dihydrophenanthrene orchinol isolated from Spiranthes sinensis Radix et Herba on the invasion and migration of human gastric cancer SGC-7901 cells and its preliminary molecular mechanism. SGC-7901 cells were cultured in vitro, after the cells were treated with different final concentrations(5, 10, 20, 40, 80 μmol·L⁻¹) of orchinol for 24, 48 or 72 hours, the effect of orchinol on cell viability was measured by MTT assay. Wound healing and Transwell assays were performed to determine the effects of different final concentrations(5, 10, 20, 40 μmol·L⁻¹) of orchinol for 48 hour on invasion and migration abilities of SGC-7901 cells, respectively. The protein expression levels of β-catenin, Wnt-3α, DvL2, cyclinD1 and GSK-3β were detected by Western blot. The results showed that 5-80 μmol·L⁻¹ orchinol inhibited the viability of SGC-7901 cells in a dose-dependent and time-dependent manner, and the IC₅₈ values of 24, 48 and 72 hours were 77.79, 42.96 and 7.85 μmol·L⁻¹, respectively. Compared with the control group, the ability of invasion and migration of SGC-7901 cells was significantly inhibited after treated with 5, 10 and 20 μmol·L⁻¹ orchinol for 48 hours (P<0.05, P<0.01), and the dose-effect relationship was observed. The results of Western blot showed that orchinol could significantly down-regulate the protein expression levels of β-catenin, Wnt3a, DvL2 and cyclinD1, and up-regulate the protein expression level of GSK-3β(P<0.05, P<0.01, P<0.001). The above results suggest that orchinol can obviously inhibit the invasion and migration of SGC-7901 cells, which may be related to its inhibition of Wnt3a/β-catenin signaling pathway and the proteins expression of downstream genes.
2. Separation and purification of 9,10-dihydrophenanthrenes and bibenzyls from Pholidota chinensis by high-speed countercurrent chromatography
Yang Chen, Shining Cai, Liang Deng, Qiang Xia, Lian-Feng Du, Guo-Zhen Cui, Jun Li, Xu-Mei Zhou, Qizhang Ye, Yan Zhou, Mao Lin J Sep Sci. 2015 Feb;38(3):453-9. doi: 10.1002/jssc.201401031. Epub 2015 Jan 7.
Stilbenoids are the main components of leaves and stems of Pholidota chinensis. In the present investigation, high-speed counter-current chromatography was used for the separation and purification of two classes of stilbenoids, namely, bibenzyls and 9,10-dihydrophenanthrenes, on a preparative scale from whole plants of P. chinensis with different solvent systems after silica gel column chromatography fractionation. n-Hexane/ethyl acetate/methanol/water (1.2:1:1:0.8, v/v/v/v) was selected as the optimum solvent system to purify 1-(3,4,5-trimethoxyphenyl)-1',2'-ethanediol (1), coelonin (2), 3,4'-dihydroxy-5,5'-dimethoxybibenzyl (3), and 2, 7- dihydroxy- 3, 4, 6- trimethoxy- 9, 10- dihydrophenanthrene (4). While 2,7-dihydroxy-3,4,6-trimethoxy- 9, 10- dihydrophenanthrene (5), batatasin III (6), orchinol (7), and 3'-O-methylbatatasin III (8) were purified by n-hexane/ethyl acetate/methanol/water (1.6:0.8:1.2:0.4, v/v/v/v). After the high-speed counter-current chromatography isolation procedure, the purity of all compounds was over 94% assayed by ultra high performance liquid chromatography. The chemical structure identification of all compounds was carried out by mass spectrometry and (1)H and (13)C NMR spectroscopy. To the best of our knowledge, the current investigation is the first study for the separation and purification of bibenzyls and 9,10-dihydrophenanthrenes by high-speed counter-current chromatography from natural resources.
3. [Chemical constituents from Pholidota cantonensis]
Bin Li, Jie-ying Gao, Juan Li, Yu-yan Chen, Shun-xiang Li Zhong Yao Cai. 2014 Jun;37(6):986-9.
Objective: To isolate and elucidate the constituents from whole plant of Pholidota cantonensis. Methods: The constituents were isolated and purified by silica gel, Sephadex LH-20 and MCI gel chromatography and recrystallization. The structures were elucida- ted on the basis of the chemical evidence and spectroscopic data. Results: Ten compounds were obtained : batatasin ll(1), orchinol(2), ephmeranthoquinone(3 ), densiflorol B (4) , 3, 5-dimethoxy-4-hydroxy-propiophenone (5) , cinnamic acid (6) , syringaresinol (7) ,24- methylenencycoartanol( 8),ergosterol peroxide(9) and β-sitosterol( 10). Conclusion: Compounds 6 and 9 are isolated from Pholidota genus for the first time,and compounds 4,5 and 7 are isolated from this plant for the first time.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
