Stilbenoid derivatives and their uses
The present invention generally provides stilbenoid derivatives and methods for using stilbenoid derivatives to modulate the activity of cannabinoid receptors or scavenge reactive nitrogen species.
1. A method for inhibiting damage by a reactive nitrogen species, the method comprising administering a monomer or an oligomer of a compound of Formula (I) to a subject in need thereof such that the reactive nitrogen species is scavenged by the compound of Formula (I) and damage by the reactive nitrogen species is inhibited, the compound of Formula (I):
wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently hydrogen, hydroxyl, hydrocarbyl, substituted hydrocarbyl, hydrocarbyloxy, substituted hydrocarbyloxy, or sulfoxy; provided that at least one of the R groups is a hydroxyl or substituted hydroxyl group; and provided that if the compound of Formula (I) is monomeric, then it is other than a compound in which (i) R 1 , R 3 , R 5 , R 6 , R 7 , R 9 , and R 10 are hydrogen, and R 2 , R 4 , and R 8 are hydroxyl; or (ii) R 1 , R 3 , R 5 , R 6 , and R 10 are hydrogen, R 2 , R 4 , R 7 , and R 9 are hydroxyl, and R 8 is methoxy.
2. The method of claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently hydrogen, hydroxyl, alkyl, alkenyl, alkyoxy, alkenyloxy, aryloxy, glucuronidyloxy, glucosyloxy, or sulfoxy.
3. The method of claim 1 , wherein R 1 , R 5 , R 6 , R 7 , R 9 , and R 10 are hydrogen; R 3 is alkenyl; and R 2 , R 4 , and R 8 are independently hydroxyl, alkoxy, glucuronidyloxy, or sulfoxy.
4. The method of claim 1 , wherein R 1 , R 5 , R 6 , R 9 , and R 10 are hydrogen; R 3 is hydroxyl or alkenyl; and R 2 , R 4 , R 7 , and R 8 are independently hydroxyl, alkoxy, glucuronidyloxy, or sulfoxy.
5. The method of claim 1 , wherein the compound of Formula (I) is a cis isomer or a trans isomer.
6. The method of claim 1 , wherein the oligomer of the compound of Formula (I) comprises cis isomers, trans isomers, or a combination of cis and trans isomers.
7. The method of claim 1 , wherein the reactive nitrogen species is peroxynitrite, nitric oxide, nitrogen dioxide, or dinitrogen trioxide.
8. The method of claim 1 , wherein the subject is a rodent, a research animal, a companion animal, an agricultural animal, or a human.
9. The method of claim 1 , wherein R 1 , R 5 , R 6 , R 9 , and R 10 are hydrogen; R 2 , R 4 , and R 8 are independently hydroxyl, alkoxy, glucuronidyloxy, or sulfoxy; R 3 is isoprenyl; and R 7 is hydrogen, hydroxyl, alkoxy, glucuronidyloxy, or sulfoxy.
10. The method of claim 9 , wherein R 2 , R 4 , R 7 , and R 8 are hydroxyl; and R 3 is 3-methyl-1-butenyl.
11. The method of claim 9 , wherein R 2 , R 4 , and R 8 are hydroxyl; R 7 is hydrogen; and R 3 is 3-methyl-but-2-enyl.
12. The method of claim 1 , wherein R 2 , R 4 , and R 8 are hydroxyl; R 7 is hydrogen; and R 3 is 3-methyl-1-butenyl.