Chromenes of polyketide origin from Peperomia villipetiola

Karina J. Malquichagua Salazar; Guillermo E. Delgado Paredes; Luis Ripalda Lluncor; Maria Claudia Max Young; Massuo Jorge Kato

doi:10.1016/j.phytochem.2005.01.003

Chromenes of polyketide origin from Peperomia villipetiola

Karina J. Malquichagua Salazar, Guillermo E. Delgado Paredes, Luis Ripalda Lluncor, Maria Claudia Max Young, Massuo Jorge Kato

Biology - Botany

Research output: Contribution to journal › Article › peer-review

32 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	573-579
Number of pages	7
Journal	Phytochemistry
Volume	66
Issue number	5
DOIs	https://doi.org/10.1016/j.phytochem.2005.01.003
State	Published - Mar 2005

Bibliographical note

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.

Keywords

Anti-fungal activity
Chromenes
Orsellinic acid
Peperomia villipetiola
Piperaceae
Structural elucidation

Access to Document

10.1016/j.phytochem.2005.01.003

Cite this

@article{f2a268c9d85640f2a79f18d38ed0acd6,

title = "Chromenes of polyketide origin from Peperomia villipetiola",

abstract = "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.",

keywords = "Anti-fungal activity, Chromenes, Orsellinic acid, Peperomia villipetiola, Piperaceae, Structural elucidation",

author = "{Malquichagua Salazar}, {Karina J.} and {Delgado Paredes}, {Guillermo E.} and Lluncor, {Luis Ripalda} and Young, {Maria Claudia Max} and Kato, {Massuo Jorge}",

note = "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.",

year = "2005",

month = mar,

doi = "10.1016/j.phytochem.2005.01.003",

language = "English",

volume = "66",

pages = "573--579",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

number = "5",

}

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 -

Chromenes of polyketide origin from Peperomia villipetiola

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this