3-Hydroxyterphenyllin
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| Category | Others |
| Catalog number | BBF-03777 |
| CAS | 66163-76-6 |
| Molecular Weight | 354.35 |
| Molecular Formula | C20H18O6 |
| Purity | ≥70% |
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Description
3-Hydroxyterphenyllin is a p-terphenyl fungal metabolite originally isolated from A. candidus that has diverse biological activities, including antioxidant, antiproliferative, antibacterial, and antiviral properties.
Specification
| Synonyms | NSC 299113 |
| Storage | Store at -20°C |
| IUPAC Name | 4-[2-hydroxy-4-(4-hydroxyphenyl)-3,6-dimethoxyphenyl]benzene-1,2-diol |
| Canonical SMILES | COC1=C(C(=C(C(=C1)C2=CC=C(C=C2)O)OC)O)C3=CC(=C(C=C3)O)O |
| InChI | InChI=1S/C20H18O6/c1-25-17-10-14(11-3-6-13(21)7-4-11)20(26-2)19(24)18(17)12-5-8-15(22)16(23)9-12/h3-10,21-24H,1-2H3 |
| InChI Key | YLSPFNUVVOKJDF-UHFFFAOYSA-N |
Properties
| Appearance | Solid Powder |
| Antibiotic Activity Spectrum | viruses |
| Boiling Point | 542.8°C at 760 mmHg |
| Density | 1.353 g/cm3 |
Reference Reading
1. Prenylated Polyhydroxy-p-terphenyls from Aspergillus taichungensis ZHN-7-07
Shengxin Cai, Xianglan Kong, Shiwei Sun, Qianqun Gu, Huinan Zhou, Tianjiao Zhu, Dehai Li J Nat Prod . 2011 May 27;74(5):1106-10. doi: 10.1021/np2000478.
Six new prenylated polyhydroxy-p-terphenyl metabolites, named prenylterphenyllins A-C (1-3) and prenylcandidusins A-C (5-7), and one new polyhydroxy-p-terphenyl with a simple tricyclic C-18 skeleton, named 4''-dehydro-3-hydroxyterphenyllin (4), were obtained together with eight known analogues (8-15) from Aspergillus taichungensis ZHN-7-07, a root soil fungus isolated from the mangrove plant Acrostichum aureum. Their structures were determined by spectroscopic methods, and their cytotoxicity was evaluated using HL-60, A-549, and P-388 cell lines. Compounds 1 and 8 exhibited moderate activities against all three cell lines (IC50 1.53-10.90 μM), whereas compounds 4 and 6 displayed moderate activities only against the P-388 cell line (IC50 of 2.70 and 1.57 μM, respectively).
2. The protective effects of Aspergillus candidus metabolites against hydrogen peroxide-induced oxidative damage to Int 407 cells
Gow-Chin Yen, Chi-Tai Yeh, Hsing-Chang Chiang, Chi-Hao Wu Food Chem Toxicol . 2003 Nov;41(11):1561-7. doi: 10.1016/s0278-6915(03)00174-1.
The protective effects of 3,3"-di-OH-terphenyllin (3,3"-DHT) and 3-OH-terphenyllin (3-HT), two secondary metabolites produced by Aspergillus candidus (CCRC31543), against hydrogen peroxide-induced oxidative damage to Int 407 cells, were evaluated. The results showed that H2O2 caused an increase in lactate dehydrogenase (LDH) leakage and DNA damage in Int 407 cells; however, the addition of 3,3"-DHT and 3-HT significantly reduced this effect (P0.05), but oxidized glutathione levels increased when Int 407 cells were pre-incubated with these two compounds. These findings suggest that 3,3"-DHT and 3-HT have the ability to protect against oxidative damage to Int 407 cells and that this protective effect may be associated with the ability to reduce ROS formation and increase catalase activity.
3. Isolation and characterization of antioxidant compounds from Aspergillus candidus broth filtrate
Y C Chang, F Sheu, G C Yen, H C Chiang J Agric Food Chem . 2001 Mar;49(3):1426-31. doi: 10.1021/jf001109t.
The objectives of this study were to isolate the antioxidative components in the broth filtrate of Aspergillus candidus (CCRC 31543), to characterize their antioxidative properties, and to evaluate their safety. Three major compounds were isolated and identified as 3,3' '-dihydroxyterphenyllin, 3-hydroxyterphenyllin, and candidusin B. In the linoleic acid peroxidation system, the inhibition of peroxidation in these three compounds was greater than 95% and was significantly higher than that of alpha-tocopherol but equal to that of BHA at 12.5-200 microg/mL. As measured using the Rancimat method in lard, 3,3' '-di-OH-terphenyllin exhibited a protection factor value of 7.82, which was substantially higher than those of BHA (5.58) and alpha-tocopherol (4.29) at 200 microg/mL. 3,3' '-di-OH-terphenyllin and 3-OH-terphenyllin also exhibited marked scavenging effects on the alpha,alpha-diphenyl-beta-picrylhydrazyl radicals (94.7 and 96.0%, respectively), which were similar to those of BHA and alpha-tocopherol. Safety studies showed that these three compounds were neither cyto- nor geno-toxic toward human intestine 407 (INT 407) cells, nor mutagenic toward Salmonella typhimurium TA98 and TA100.
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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 ╳
