ORTEGA MARÍA GABRIELA
Congresos y reuniones científicas
Título:
FLAVONOIDS FROM Dalea boliviana AS TYROSINASE INHIBITORS
Autor/es:
MARIANA PERALTA; SANTI, MARÍA DANIELA; CABRERA J.L; ORTEGA G.
Lugar:
Córdoba
Reunión:
Otro;  Primera Reunión Internacional de Ciencias Farmacéuticas; 2010
Resumen:

The melanin formation is one of the most important factors to determine the mammalian skin colour.

Tyrosinase is a mixed function oxidase enzyme which catalyzes two different reactions in the synthesis of

melanin: the formation of 3, 4-dihydroxyphenylalanine (L-DOPA) from tyrosine and further oxidizes LDOPA

to dopaquinone. Tyrosinase inhibitors may be of important to treat abnormal pigmentation disorders

and to use as skin whitening agents in cosmetics.(1) Our research group began the chemical and

pharmacological study of Dalea boliviana. We previously report the isolation and structural characterization

of three new prenylated flavanones from the hexanes extract of D. boliviana roots: (2S) - 5, 7, 2 ´ - trihydroxy-

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

of three new prenylated flavanones from the hexanes extract of D. boliviana roots: (2S) - 5, 7, 2 ´ - trihydroxy-

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

pharmacological study of Dalea boliviana. We previously report the isolation and structural characterization

of three new prenylated flavanones from the hexanes extract of D. boliviana roots: (2S) - 5, 7, 2 ´ - trihydroxy-

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

of three new prenylated flavanones from the hexanes extract of D. boliviana roots: (2S) - 5, 7, 2 ´ - trihydroxy-

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds 1-4 as

tyrosinase inhibitors.

tyrosinase inhibitors.

5 ´-(1´´´,1´´´-dimethylallyl)-8-prenylflavanone (1), (2S) - 5, 7, 2´ - trihydroxy-8, 3 ´ - diprenylflavanone (2), and

(2S) - 5, 2 ´ - dihydroxy-6 ", 6"- dimethylchromeno-(7,8:2´´,3´´) - 3 ´ - prenylflavanone (3), together with a

known chromeno (dimethylpyrano) flavanone, obovatin (4).(2,3,4) Taking into account that similar compounds

have been related to inhibition of tyrosinase activity, (5,6,7) we propose to evaluate compounds