Antimycobacterial metabolites from Plectranthus: Royleanone derivatives against Mycobacterium tuberculosis strains

Patrícia Rijo; M. Fátima Simões; A. Paula Francisco; Rosario Rojas; Robert H. Gilman; Abraham J. Vaisberg; Benjamín Rodríguez; Cristina Moiteiro

doi:10.1002/cbdv.200900099

Antimycobacterial metabolites from Plectranthus: Royleanone derivatives against Mycobacterium tuberculosis strains

Patrícia Rijo
, M. Fátima Simões
, A. Paula Francisco
, Rosario Rojas
, Robert H. Gilman
, Abraham J. Vaisberg
, Benjamín Rodríguez
, Cristina Moiteiro

School of Science and Engineering

University of Lisbon
Universidad Peruana Cayetano Heredia
Instituto de Química Orgánica-CSIC
DTIQ

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

53 Scopus citations

Abstract

The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7α-acetoxy- 6β,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H₃₇Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.

Original language	English
Pages (from-to)	922-932
Number of pages	11
Journal	Chemistry and Biodiversity
Volume	7
Issue number	4
DOIs	https://doi.org/10.1002/cbdv.200900099
State	Published - Apr 2010

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Access to Document

10.1002/cbdv.200900099

Cite this

@article{3230ea5872f148248c8d45e15319b99b,

title = "Antimycobacterial metabolites from Plectranthus: Royleanone derivatives against Mycobacterium tuberculosis strains",

abstract = "The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7α-acetoxy- 6β,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H37Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.",

author = "Patr{\'i}cia Rijo and Sim{\~o}es, \{M. F{\'a}tima\} and Francisco, \{A. Paula\} and Rosario Rojas and Gilman, \{Robert H.\} and Vaisberg, \{Abraham J.\} and Benjam{\'i}n Rodr{\'i}guez and Cristina Moiteiro",

year = "2010",

month = apr,

doi = "10.1002/cbdv.200900099",

language = "Ingl{\'e}s",

volume = "7",

pages = "922--932",

journal = "Chemistry and Biodiversity",

issn = "1612-1872",

number = "4",

}

TY - JOUR

T1 - Antimycobacterial metabolites from Plectranthus

T2 - Royleanone derivatives against Mycobacterium tuberculosis strains

AU - Rijo, Patrícia

AU - Simões, M. Fátima

AU - Francisco, A. Paula

AU - Rojas, Rosario

AU - Gilman, Robert H.

AU - Vaisberg, Abraham J.

AU - Rodríguez, Benjamín

AU - Moiteiro, Cristina

PY - 2010/4

Y1 - 2010/4

N2 - The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7α-acetoxy- 6β,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H37Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.

AB - The antimycobacterial activities of eight diterpenes, 1-8, isolated previously from Plectranthus and eleven esters, 9-19, of 7α-acetoxy- 6β,12-dihydroxyabieta-8,12-diene-11,14-dione (5) were evaluated against the MTB strains H37Rv and MDR. Only diterpenoids with a quinone framework revealed anti-MTB activity. Abietane 5 and its 6,12-dibenzoyl, 12-methoxybenzoyl, 12-chlorobenzoyl, and 12-nitrobenzoyl esters, 9, 11, 12, and 13, respectively, showed potent activities against the MDR strain with MIC values between 3.12 and 0.39 μg/ml. Cytotoxic activities towards 3T3 and Vero cells were also evaluated. Compound 11, with the best selectivity index, may be a suitable lead for further chemical modifications. The complete structural elucidation of the new esters, 9-14, 16, 18, and 19, as well as the NMR data of known derivatives 15 and 17 are reported.

UR - https://www.scopus.com/pages/publications/77951197862

U2 - 10.1002/cbdv.200900099

DO - 10.1002/cbdv.200900099

M3 - Artículo

C2 - 20397225

AN - SCOPUS:77951197862

SN - 1612-1872

VL - 7

SP - 922

EP - 932

JO - Chemistry and Biodiversity

JF - Chemistry and Biodiversity

IS - 4

ER -

Antimycobacterial metabolites from Plectranthus: Royleanone derivatives against Mycobacterium tuberculosis strains

Abstract

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this