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Terphenyllin is a naturally occuring p-terphenyl metabolite extracted from the corally bioavailable derived fungus Aspergillus candidus, it has potent α-glucosidase inhibitory activity.
| Targets |
- The target of Terphenyllin is α-glucosidase (an enzyme involved in carbohydrate metabolism), with an IC50 value of 28.6 ± 1.2 μM [1]
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| ln Vitro |
- α-Glucosidase Inhibitory Activity: Terphenyllin showed concentration-dependent inhibitory activity against α-glucosidase. At a concentration of 50 μM, the inhibition rate reached 82.3 ± 2.1%; its IC50 value was determined as 28.6 ± 1.2 μM, which was weaker than the positive control acarbose (IC50 = 8.5 ± 0.6 μM) but still exhibited moderate inhibitory potency [1]
- Cytotoxic Activity: Terphenyllin had selective cytotoxicity against four human cancer cell lines. Against HepG2 (hepatocellular carcinoma) cells, it showed an IC50 of 35.7 ± 1.8 μM; against MCF-7 (breast cancer) cells, the IC50 was 42.3 ± 2.0 μM; against A549 (lung cancer) cells, the IC50 was 48.5 ± 2.2 μM; and against HCT116 (colorectal cancer) cells, the IC50 was 51.2 ± 2.5 μM. It had low toxicity to normal human LO2 (hepatocyte) cells, with a cell viability of over 80% at a concentration of 50 μM [1] - Antibacterial Activity: Terphenyllin exhibited antibacterial activity against Gram-positive bacteria. For Staphylococcus aureus , it showed a minimum inhibitory concentration (MIC) of 32 μg/mL and a zone of inhibition of 12.5 ± 0.5 mm (at 50 μg/disc); for Bacillus subtilis , the MIC was 64 μg/mL and the zone of inhibition was 10.2 ± 0.3 mm (at 50 μg/disc). It had no obvious antibacterial activity against Gram-negative bacteria such as Escherichia coli and Pseudomonas aeruginosa (zone of inhibition < 6 mm) [1] |
| Enzyme Assay |
- Reagent Preparation: α-Glucosidase solution was prepared in 0.1 M phosphate buffer (pH 6.8) at a concentration of 0.2 U/mL; p-nitrophenyl-α-D-glucopyranoside (pNPG, substrate) was dissolved in the same buffer to a concentration of 5 mM; Terphenyllin was dissolved in DMSO to prepare stock solutions of different concentrations (10–200 μM), with the final DMSO concentration in the reaction system not exceeding 1% (v/v) [1]
- Reaction Procedure: A 50 μL aliquot of Terphenyllin solution (at different concentrations) was mixed with 50 μL of α-glucosidase solution in a 96-well plate, and incubated at 37°C for 15 minutes. Then, 50 μL of pNPG solution was added to initiate the reaction, and the mixture was further incubated at 37°C for 30 minutes [1] - Detection and Calculation: The reaction was terminated by adding 100 μL of 0.1 M Na2CO3 solution. The absorbance at 405 nm was measured using a microplate reader. The inhibition rate was calculated using the formula: [(Acontrol - Atreated)/Acontrol] × 100%, where Acontrol is the absorbance of the blank group (without Terphenyllin) and Atreated is the absorbance of the Terphenyllin-treated group. The IC50 value was obtained by plotting the inhibition rate against the logarithm of Terphenyllin concentration and fitting with a dose-response curve [1] |
| Cell Assay |
- Cytotoxicity Assay (MTT Method):
1. Four human cancer cell lines (HepG2, MCF-7, A549, HCT116) and normal LO2 cells were cultured in RPMI 1640 medium containing 10% fetal bovine serum at 37°C with 5% CO2. Cells were seeded into 96-well plates at a density of 5×103 cells/well and incubated for 24 hours to allow attachment [1] 2. Terphenyllin stock solution (dissolved in DMSO) was diluted with medium to final concentrations of 10, 20, 40, 80, and 160 μM, and added to the wells (100 μL/well). The control group received medium containing 1% DMSO, and the positive control group received doxorubicin (IC50 = 1.2–3.5 μM). Each concentration was set with 3 replicate wells [1] 3. After incubation for 48 hours, 20 μL of MTT solution (5 mg/mL) was added to each well, and incubation continued for 4 hours. The supernatant was discarded, and 150 μL of DMSO was added to dissolve the formazan crystals. The absorbance at 490 nm was measured, and the cell viability was calculated. The IC50 value was determined by dose-response curve fitting [1] - Antibacterial Activity Assays: 1. Disc Diffusion Method: Staphylococcus aureus , Bacillus subtilis , Escherichia coli , and Pseudomonas aeruginosa were cultured in LB broth at 37°C overnight. The bacterial suspension was adjusted to 1×106 CFU/mL and spread evenly on LB agar plates. Sterile filter paper discs (6 mm diameter) soaked with Terphenyllin solution (50 μg/disc, dissolved in DMSO) were placed on the agar surface. The plates were incubated at 37°C for 24 hours, and the diameter of the inhibition zone around each disc was measured [1] 2. Minimum Inhibitory Concentration (MIC) Determination: Terphenyllin was serially diluted with LB broth to concentrations of 2, 4, 8, 16, 32, 64, and 128 μg/mL. Each dilution (100 μL) was mixed with 100 μL of bacterial suspension (1×106 CFU/mL) in a 96-well plate. After incubation at 37°C for 24 hours, the MIC was defined as the lowest concentration of Terphenyllin that completely inhibited bacterial growth (no visible turbidity) [1] |
| Toxicity/Toxicokinetics |
Terphenyllin exhibits low cytotoxicity to normal human LO2 cells: at a concentration of 50 μM, the cell survival rate remains above 80%; even at 100 μM, the cell survival rate is still 65.2 ± 3.1%, indicating that it has weak cytotoxicity to normal hepatocytes [1].
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| References | |
| Additional Infomation |
Terphenyllin is a para-terphenyl compound with the structure 1,1':4',1''-terphenyl, substituted with methoxy groups at the 3' and 6' positions and hydroxyl groups at the 2', 4', and 4'' positions. It has been isolated from Aspergillus taichungensis. It is a fungal toxin and a metabolite of Aspergillus. It is a para-terphenyl compound belonging to the phenolic class and is also a dimethoxybenzene. Terphenyllin has been reported in Aspergillus campestris, Aspergillus taichungensis, and Aspergillus candidus, and relevant data are available. - Terphenyllin is a naturally occurring para-terphenyl derivative isolated from fungal secondary metabolites. Its moderate α-glucosidase inhibitory activity indicates its potential as a lead compound for antidiabetic drugs; its selective cytotoxicity against cancer cells and antibacterial activity against Gram-positive bacteria also lay the foundation for its further development as an anticancer or antibacterial drug [1].
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| Molecular Formula |
C20H18O5
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|---|---|
| Molecular Weight |
338.35392
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| Exact Mass |
338.115
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| Elemental Analysis |
C, 71.00; H, 5.36; O, 23.64
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| CAS # |
52452-60-5
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| PubChem CID |
100437
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| Appearance |
White to off-white solid powder
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| Density |
1.285g/cm3
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| Boiling Point |
499.2ºC at 760 mmHg
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| Flash Point |
255.7ºC
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| Index of Refraction |
1.636
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| LogP |
4.154
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
25
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| Complexity |
401
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| Defined Atom Stereocenter Count |
0
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| SMILES |
COC1=C(C(=C(C(=C1)C2=CC=C(C=C2)O)OC)O)C3=CC=C(C=C3)O
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| InChi Key |
YNEMPXKRLPZFAX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H18O5/c1-24-17-11-16(12-3-7-14(21)8-4-12)20(25-2)19(23)18(17)13-5-9-15(22)10-6-13/h3-11,21-23H,1-2H3
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| Chemical Name |
2,5-bis(4-hydroxyphenyl)-3,6-dimethoxyphenol
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| Synonyms |
Terphenyllin
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~83.33 mg/mL (~246.28 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9555 mL | 14.7776 mL | 29.5552 mL | |
| 5 mM | 0.5911 mL | 2.9555 mL | 5.9110 mL | |
| 10 mM | 0.2956 mL | 1.4778 mL | 2.9555 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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