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Yadanziolide A is a naturally occurring antiviral agent isolated from the cultivated dry seeds of Brucea javanica with antiviral and antitumor activities. It exhibits an IC50 of 5.5 μM against tobacco mosaic virus.
| Targets |
TMV/Tobacco mosaic virus (IC50 = 5.5 μM)
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|---|---|
| ln Vitro |
Yadanziolide A is a natural product found in Brucea mollis and Brucea javanica. Yadanziolide A inhibited the replication of Tobacco Mosaic Virus (TMV) with an IC50 of 5.5μM and an inhibition rate of 83.4% at 20 μM.[1]
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| ln Vivo |
The inhibitory activities of compounds 1−17 (compound # 9 is yadanziolide A))against TMV replication were tested using two approaches. First, the half-leaf method was used to test the antiviral activity in the local lesion host N. glutinosa in vivo. Then, the leaf-disk method was used to evaluate the antiviral activity of each compound in the systemic infection host N. tabacum cv. K326. Ningnanmycin, a commercial product for plant disease in China, was used as a positive control.[1]
The antiviral inhibition rates of compounds 1−17 at the concentration of 20 μM tested by the half-leaf method were listed in Table 2. The results showed that all the compounds exhibited inhibition activities against TMV replication with inhibition rates ranging from 24.1% to 94.6%. Except compound 11 (bruceoside A, 24.1%), all the other compounds showed higher inhibition rates than that of the positive control, ningnanmycin (25.3%). Among the 17 quassinoids, brusatol (3) and bruceine B (4), sharing a diosphenol (3-hydroxy-3-en-2-one) unit in ring A, exhibited the best activity, with the inhibition rates 94% and 94.6%, respectively. Replacement with β-glucose at 3-OH (5−7) or a hydrogenation at 3-OH (8−9) gave a slight decrease of activity (Table 2). The saturation of the 3,4-double bond resulted in great loss of the antiviral activity from 94% (3) to 52% (1). The lost of the carbonyl at C-2 can also led to great lost in antiviral activity; the inhibition rate decreased from 84.7% (8) to 31.1% (13) and 30.6% (15) and from 83.4% (9) to 24.1% (14) with the carbonyl at C-2 in 8−9 substituted by the hydrogen (13−14) or β-glucose (15), which indicated the C-2 carbonyl was essential for the antiviral activity. Compared with compounds 1−17, nigakilactone B (a quassinoid from Picrasma quassioides), without an epoxymethano bridge from C-8 to C-13, showed no anti-TMV activity, indicating the epoxymethano bridge moiety might be essential for anti-TMV activity.[1] |
| Cell Assay |
To assess whether these quassinoids inhibit TMV replication in systemic infection host N. tabacum cv. K326, the leaf-disk method along with Western blot analysis of TMV coat protein (CP) in the presence of 20 μM compound was carried out (Figure 2). The bands of CP were not detected, when treated with compounds 3−9 (Figure 2A and B); while treated with compounds with moderate activity (16, 17) or low activity (10−15), weak or strong bands were detected (Figure 2B). This result was in accordance with their inhibition rates in Table 2. However, nigakilactone B, a quassinoid from Picrasma quassioides Benn., showed no activity with a strong CP band as that of negative control (Figure 2B). Western-blot analysis further confirmed quassinoids from Brucea javanica could inhibit the accumulation of TMV CP in vitro. The quantity of TMV CP decreased with increasing concentrations of compounds in a dose-dependent manner (e.g., Figure 2C, compound 3).[1]
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| References | |
| Additional Infomation |
yadanziolide A has been reported in Brucea mollis and Brucea javanica with data available.
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| Molecular Formula |
C20H26O10
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|---|---|
| Molecular Weight |
426.4144
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| Exact Mass |
426.153
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| CAS # |
95258-14-3
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| PubChem CID |
10320238
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| Appearance |
Typically exists as White to off-white solids
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| Density |
1.68±0.1 g/cm3
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| Melting Point |
285-287 ºC
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| Source |
Brucea javanica
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| LogP |
-2.9
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
30
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| Complexity |
872
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| Defined Atom Stereocenter Count |
11
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| SMILES |
O[C@]12[C@@]3(OC[C@@]41[C@H](OC([C@@H]2O)=O)C[C@H]1C(=CC([C@H]([C@]1(C)[C@H]4[C@H]([C@@H]3O)O)O)=O)C)CO
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| InChi Key |
QXKKRGMRXXMDDP-JVDXBALSSA-N
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| InChi Code |
InChI=1S/C20H26O10/c1-7-3-9(22)13(24)17(2)8(7)4-10-18-6-29-19(5-21,14(25)11(23)12(17)18)20(18,28)15(26)16(27)30-10/h3,8,10-15,21,23-26,28H,4-6H2,1-2H3/t8-,10+,11+,12+,13+,14-,15-,17-,18+,19+,20-/m0/s1
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| Chemical Name |
(1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione
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| Synonyms |
yadanziolide A; 95258-14-3; (1R,2R,3R,6R,8S,12S,13S,14R,15R,16S,17R)-2,3,12,15,16-Pentahydroxy-17-(hydroxymethyl)-9,13-dimethyl-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-4,11-dione; CHEMBL2037039;
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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 : ~100 mg/mL (~234.52 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.86 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 25.0 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: ≥ 2.5 mg/mL (5.86 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 25.0 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: ≥ 2.5 mg/mL (5.86 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 | 2.3452 mL | 11.7258 mL | 23.4516 mL | |
| 5 mM | 0.4690 mL | 2.3452 mL | 4.6903 mL | |
| 10 mM | 0.2345 mL | 1.1726 mL | 2.3452 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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