Thymoquinone/harmaline and related reaction products
New compositions of matter useful for the treatment of human diabetes and cancers comprise the reaction products of thymoquinone and harmaline or harmaline-like compounds, such as β-carboline compounds, and the derivatives, solvates, prodrugs, isomers, and tautomers of such compounds.
1. A method of treating a subject to decrease the blood glucose level of the subject, comprising the step of administering to the subject one or more compounds of Structures X and XI below, and the derivatives, solvates, prodrugs, isomers, tautomers, esters, metal complexes, and salts thereof:
where the six-membered A ring in each of the above structures is either phenyl or cyclohexadiene, the R1-R5 substituents may be attached at any valence-permitted position around the corresponding A rings, R1 is a C1-C4 alkyl group, R2 is H or a C1-C4 alkyl group, R3 and R4 are independently either —OH or ═O, R5 is isopropyl, and the dotted bond line refers to the fact that the bond between the 1 position on the A ring and the intermediate CH2 or CH group of the linker between the A ring and the six-membered, N-containing pyridyl ring may be either a single bond or a double bond, and in structure XI, the A rings may be the same or different.
2. The method of claim 1 , the one or more compounds of Structure X having a molecular weight of about 378.
3. The method of claim 1 , the one or more compounds of Structure XI having a molecular weight of about 540.
4. The method of claim 1 , the one or more compounds of Structure X having the R3 and R4 substituents both being —OH.
5. The method of claim 1 , said R3 and R4 —OH substituents being located at A ring positions 3 and 6, respectively.
6. The method of claim 1 , the one or more compounds of Structure X having said R2 substituent being methyl.
7. The method of claim 6 , the compounds of Structure X having an R2 methyl substituent located either at A ring positions 2 or 5, and an R5 isopropyl substituent located at the other of said A ring positions 2 or 5.
8. The method of claim 1 , said A rings each being phenyl.
9. The method of claim 1 , said administered compound being of the Structure
10. The method of claim 1 , said administered compound being of the Structure