| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
| ln Vitro |
Phaseoloidin displayed direct in vitro activity against lepidopteran herbivores. When Manduca sexta (tobacco hornworm) larvae were fed artificial diets supplemented with Phaseoloidin, dose-dependent growth inhibition and survival reduction were observed. At a concentration of 0.5% (w/w) in the artificial diet, the weight gain of M. sexta larvae was significantly lower than that of the control group (without Phaseoloidin) after 7 days of continuous feeding. When the concentration was increased to 1.0% (w/w), the survival rate of M. sexta larvae decreased by approximately 30% compared to the control. Additionally, Spodoptera exigua (beet armyworm), another lepidopteran species, also showed reduced larval growth when exposed to Phaseoloidin-containing diets, though the inhibitory effect was less pronounced than that on M. sexta. [1]
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| ln Vivo |
In vivo experiments using Nicotiana attenuata plants demonstrated that Phaseoloidin contributes to the plant’s resistance against lepidopteran herbivores. In Phaseoloidin-deficient N. attenuata plants (generated either by physically removing trichomes—where Phaseoloidin is exclusively accumulated—or by genetic manipulation to silence Phaseoloidin biosynthesis), the resistance to M. sexta larvae was significantly impaired. Larvae feeding on these Phaseoloidin-depleted plants had a 40–50% higher weight gain and a shorter developmental period (by 2–3 days) compared to those feeding on wild-type N. attenuata plants (with intact trichomes and normal Phaseoloidin levels). Moreover, wild-type plants with abundant Phaseoloidin exhibited less leaf damage (reduced by approximately 35%) caused by M. sexta feeding, compared to trichome-removed or Phaseoloidin-silenced plants. These results confirmed that Phaseoloidin is a key factor in the in vivo resistance of N. attenuata to lepidopteran herbivores. [1]
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| Animal Protocol |
The "animal" in this protocol refers to lepidopteran herbivore larvae (primarily M. sexta and S. exigua), and the detailed procedure for evaluating Phaseoloidin’s activity is as follows:
1. Insect larvae were reared in a controlled environment with a temperature of 25±2°C, a photoperiod of 16 h light/8 h dark, and a relative humidity of 60±5%. 2. For the artificial diet experiment: Phaseoloidin was dissolved in distilled water and mixed into the artificial diet matrix to prepare test diets with concentrations of 0.1%, 0.5%, and 1.0% (w/w). A control diet was prepared by adding the same volume of distilled water without Phaseoloidin. 3. Newly hatched 1st-instar M. sexta or S. exigua larvae were individually placed in plastic containers (5 cm in diameter). Each larva was provided with 5 g of the prepared diet (either test or control), and the diet was replaced every 2 days to ensure freshness. 4. For the in planta feeding experiment: Wild-type N. attenuata plants (with intact trichomes) and Phaseoloidin-deficient plants (trichome-removed or genetically silenced) were grown in a greenhouse under conditions of 26±2°C and 16 h light/8 h dark for 6–8 weeks until they reached the rosette stage. 5. Third-instar M. sexta larvae with uniform initial weight (approximately 50 mg) were starved for 2 h to standardize their feeding state. Each larva was then placed on the upper leaves of a test plant, and the plant was covered with a fine mesh bag to prevent larval escape. 6. During the 10-day experimental period, larval weight was measured every 2 days using an electronic balance, and leaf damage area was quantified using a grid paper method. Larval survival rate and developmental stage (e.g., time to reach the 5th instar) were recorded daily. [1] |
| References | |
| Additional Infomation |
It has been reported that adipoxane has been found in Entada pursaetha, Entada phaseoloides and Entada rheedei, and related data have been reported.
1. Adipoxane is a uricoside, a secondary metabolite, specifically synthesized and stored in the trichomes of wild tobacco (Nicotiana attenuata). Its chemical structure consists of a uricoside moiety covalently linked to a glucose residue via a β-glycosidic bond. [1] 2. The biological function of adipoxane is as a constitutive defense compound in wild tobacco. Unlike inducible plant defense metabolites (which are synthesized only after attack by herbivorous insects), adipoxane persists in the trichomes and can immediately protect the plant from lepidopteran herbivorous insects. [1] 3. It is speculated that the defense mechanism of adipoxane is to directly interfere with the digestion or physiological processes of herbivorous larvae (e.g., inhibit nutrient absorption or disrupt intestinal function), but its exact molecular mechanism has not been fully elucidated in the literature. [1] |
| Molecular Formula |
C14H18O9
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|---|---|
| Molecular Weight |
330.2873
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| Exact Mass |
330.095
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| CAS # |
118555-82-1
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| PubChem CID |
14104237
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| Appearance |
White to off-white solid powder
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| LogP |
-1.802
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
23
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| Complexity |
404
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC(=C(C=C1O)CC(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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| InChi Key |
MVFYXXNAFZRZAM-RGCYKPLRSA-N
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| InChi Code |
InChI=1S/C14H18O9/c15-5-9-11(19)12(20)13(21)14(23-9)22-8-2-1-7(16)3-6(8)4-10(17)18/h1-3,9,11-16,19-21H,4-5H2,(H,17,18)/t9-,11-,12+,13-,14-/m1/s1
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| Chemical Name |
2-[5-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]acetic acid
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (~302.76 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.57 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 (7.57 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 (7.57 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 | 3.0276 mL | 15.1382 mL | 30.2764 mL | |
| 5 mM | 0.6055 mL | 3.0276 mL | 6.0553 mL | |
| 10 mM | 0.3028 mL | 1.5138 mL | 3.0276 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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