TY - JOUR
T1 - Chromenes of polyketide origin from Peperomia villipetiola
AU - Malquichagua Salazar, Karina J.
AU - Delgado Paredes, Guillermo E.
AU - Lluncor, Luis Ripalda
AU - Young, Maria Claudia Max
AU - Kato, Massuo Jorge
N1 - Funding Information:
The work was funded by grants from CNPq. The authors thank Ms. Consuelo Rojas Idrogo (Universidad Pedro Ruiz Gallo, Lambayeque, Peru) for collecting the plant material and Santos Llatas Quiroz for the botanical identification.
PY - 2005/3
Y1 - 2005/3
N2 - An extract of leaves and stems of Peperomia villipetiola has been found to contain myristicin (3-methoxy-4,5-methylenedioxy-allylbenzene) and seven chromenes, whose structures are methyl 5-hydroxy-7-methyl-2,2-dimethyl-2H-1- chromene-6-carboxylate (1), methyl 5-methoxy-7-methyl-2,2-dimethyl-2H-1- chromene-8-carboxylate (2), methyl 7-hydroxy-5-methyl-2,2-dimethyl-2H-1- chromene-6-carboxylate (3), methyl 7-methoxy-5-methyl-2,2-dimethyl-2H-1- chromene-6-carboxylate (4), 5-methanol-7-hydroxy-2,2-dimethyl-2H-1-chromene-6- carboxylic acid (5), 5-methanol-7-methoxy-2,2-dimethyl-2H-1-chromene-6- carboxylic acid (6), and methyl 5-acetoxymethanol-7-hydroxy-2,2-dimethyl-2H-1- chromene-6-carboxylate (7). A biosynthetic rationale for 1-7 suggests that orsellinic acid may be a common intermediate. The anti-fungal activities of the chromenes were measured bioautographically against Cladosporium cladosporioides and Cladosporium sphaerospermum: compounds 6 and 7 were found to be the most active.
AB - An extract of leaves and stems of Peperomia villipetiola has been found to contain myristicin (3-methoxy-4,5-methylenedioxy-allylbenzene) and seven chromenes, whose structures are methyl 5-hydroxy-7-methyl-2,2-dimethyl-2H-1- chromene-6-carboxylate (1), methyl 5-methoxy-7-methyl-2,2-dimethyl-2H-1- chromene-8-carboxylate (2), methyl 7-hydroxy-5-methyl-2,2-dimethyl-2H-1- chromene-6-carboxylate (3), methyl 7-methoxy-5-methyl-2,2-dimethyl-2H-1- chromene-6-carboxylate (4), 5-methanol-7-hydroxy-2,2-dimethyl-2H-1-chromene-6- carboxylic acid (5), 5-methanol-7-methoxy-2,2-dimethyl-2H-1-chromene-6- carboxylic acid (6), and methyl 5-acetoxymethanol-7-hydroxy-2,2-dimethyl-2H-1- chromene-6-carboxylate (7). A biosynthetic rationale for 1-7 suggests that orsellinic acid may be a common intermediate. The anti-fungal activities of the chromenes were measured bioautographically against Cladosporium cladosporioides and Cladosporium sphaerospermum: compounds 6 and 7 were found to be the most active.
KW - Anti-fungal activity
KW - Chromenes
KW - Orsellinic acid
KW - Peperomia villipetiola
KW - Piperaceae
KW - Structural elucidation
UR - http://www.scopus.com/inward/record.url?scp=13844266460&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2005.01.003
DO - 10.1016/j.phytochem.2005.01.003
M3 - Article
C2 - 15721950
AN - SCOPUS:13844266460
SN - 0031-9422
VL - 66
SP - 573
EP - 579
JO - Phytochemistry
JF - Phytochemistry
IS - 5
ER -