Pentacyclic triterpene compounds and uses thereof
Disclosed herein is a PEGylated bis pentacyclic triterpene, compositions comprising the PEGylated bis pentacyclic triterpene, methods of preparing the PEGylated bis pentacyclic triterpene, and a method of treating or preventing a fungal disease in a plant using the compounds and compositions disclosed herein. The PEGylated bis pentacyclic triterpene has the formula A-P-B, wherein A is a first pentacyclic triterpene; B is a second pentacyclic triterpene; and P is a polyethylene glycol (PEG) molecule.
1. A PEGylated bis pentacyclic triterpene having the formula:
A---P---B,
wherein,
A is a first pentacyclic triterpene;
B is a second pentacyclic triterpene; and
P is a polyethylene glycol (PEG) molecule with an average molecular weight of from about 400 daltons (Da) to about 8000 Da, for use in treating a fungal disease in a plant, wherein the fungal disease is blight;
said first and second pentacyclic triterpenes are each independently betulin, betulinic acid, or lupeol; and
A and B are each independently covalently bound to P by an ester linkage at C3 or C28.
2. The PEGylated bis pentacyclic triterpene of claim 1 , wherein the first and second pentacyclic triterpenes are each betulin.
3. The PEGylated bis pentacyclic triterpene of claim 1 , wherein the PEG molecule has a molecular weight of about 1500 Da to about 8,000 Da.
4. The PEGylated bis pentacyclic triterpene of claim 3 , wherein the PEG molecule has a molecular weight of about 3,000 Da.
5. The PEGylated bis pentacyclic triterpene of claim 1 , wherein the PEG molecule is α,ω biscarboxymethyl PEG.
6. The PEGylated bis pentacyclic triterpene according to claim 1 , wherein the first and second pentacyclic triterpenes are each betulin, the PEG molecule has a molecular weight of about 1500 Da to about 8,000 Da, and the blight is
caused by a fungal pathogen selected from the group consisting of Phytophthora infestans, Microdochium nivale , and Botrytis cinerea.
7. A fungicidal composition comprising the PEGylated bis pentacyclic triterpene as defined in claim 1 ; and an agriculturally acceptable diluent, for treating blight in plants.
8. A method of treating a fungal disease in a plant, wherein the fungal disease is blight, said method comprising:
applying to the plant, to a soil supporting the plant, or to both the plant and the soil supporting the plant, a composition comprising:
a PEGylated bis pentacyclic triterpene having the formula:
A---P---B,
wherein,
A is a first pentacyclic triterpene;
B is a second pentacyclic triterpene; and
P is a polyethylene glycol (PEG) molecule with an average molecular weight of from about 400 daltons (Da) to about 8000 Da; and
an agriculturally acceptable diluent;
wherein the first and second pentacyclic triterpenes are each independently betulin, betulinic acid, or lupeol; and
wherein A and B are each independently linked to P by an ester linkage at C3 or C28.
9. The method of claim 8 , wherein the composition is applied to the leaves of the plant.
10. The method of claim 8 , wherein the first and second pentacyclic triterpene are each betulin.
11. The method of claim 8 , wherein the PEG molecule has a molecular weight of about 1500 Da to about 8,000 Da.
12. The method of claim 11 , wherein the PEG molecule has a molecular weight of about 3,000 Da.
13. The method of claim 8 , wherein the PEG molecule is α,ω biscarboxymethyl PEG.
14. The method of treating a fungal disease in a plant according to claim 8 , wherein the first and second pentacyclic triterpenes are each betulin, the PEG molecule has a molecular weight of about 1500 Da to about 8,000 Da, and the blight is caused by a fungal pathogen selected from the group consisting of Phytophthora infestans, Microdochium nivale , and Botrytis cinerea.