Abietane diterpenes from Plectranthus madagascariensis: A cytotoxicity screening

Matias, Diogo; Pereira, Filipe; Nicolai, Marisa; Roberto, Amílcar; Saraiva, Nuno; Fernandes, AS; Simões, MF; Lanza, AD; Reis, Catarina Pinto; Rijo, Patrícia

doi:10.1055/s-0034-1394809

Cited by 3 publications

(8 citation statements)

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“…The extract obtained by maceration with acetone (E2), which had the highest combinatory yield of royleanone abietanes (Table 1), was the most cytotoxic. 24 The cytotoxic activities of the royleanone diterpenes, that is, against breast cancer cell lines, have been previously reported. 11,19 Additionally, coleon U ( 5 ) has been described in the literature as a potent cytotoxic agent, being active against breast, 11,19 leukemia, 10,19,26 and melanoma 11,19 cancer cell lines.…”

Section: Results and Discussionmentioning

confidence: 98%

“…Coleon U has been isolated from several Plectranthus species, such as Plectranthus forsteri , 23 P. grandidentatus, 10,11 P. madagascariensis 24 and P. myrianthus , 25 exhibits potent cytotoxic effects transversal to several human cancer cell lines, including breast, 11,19 lung, 11 leukemia, 10,19,26 and melanoma. 11,19 Moreover, coleon U has been described as a potent and selective activator of the proapoptotic protein kinases C-δ (PKCδ) and C-ε (PKCε), which can be on the basis of its reported antitumor action.…”

Section: Results and Discussionmentioning

confidence: 99%

“…18 Abietane diterpenes of the royleanone and coleon type commonly found in the Plectranthus genus, as well as other abietanoid quinone methides, such as Parvifloron D isolated from Plectranthus ecklonii, 9 have been described as potent antiproliferative and/or cytotoxic agents. 9−11,19−21 Previous cytotoxicity activity screening performed by our group from Plectranthus madagascariensis, P. neochilus, and Plectranthus porcatus revealed promising cytotoxic activity of the P. madagascariensis extract obtained by maceration in acetone and in the MDA-MB-231 breast cancer cell line, 24 encouraging further research. In this study, the chemical composition of several P. madagascariensis extracts obtained using different organic solvents and extraction methodologies was detailed using high-performance liquid chromatography with a diode array detector (HPLC-DAD) and complementary spectroscopic methodologies, and the major compounds were identified and quantified.…”

Section: ■ Introductionmentioning

confidence: 93%

“…23,26 Cytotoxicity Evaluation. The cytotoxic effects of P. madagascariensis extracts have been previously evaluated in the MDA-MB-231 cancer cell line by our group, 24 and the isolated abietane diterpenes most likely contribute to the cytotoxicity of P. madagascariensis extracts. The extract obtained by maceration with acetone (E2), which had the highest combinatory yield of royleanone abietanes (Table 1), was the most cytotoxic.…”

Section: ■ Introductionmentioning

confidence: 99%

“…neochilus, and Plectranthus porcatus revealed promising cytotoxic activity of the P. madagascariensis extract obtained by maceration in acetone and in the MDA-MB-231 breast cancer cell line, encouraging further research. In this study, the chemical composition of several P.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Activity of Royleanone Diterpenes from Plectranthus madagascariensis Benth

et al. 2019

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Cytotoxicity screenings have identified Plectranthus plants as potential sources of antitumor lead compounds. In this work, several extracts from Plectranthus madagascariensis were prepared using different solvents (acetone, methanol, and supercritical CO 2 ) and extraction techniques (maceration, ultrasound-assisted, and supercritical fluid extraction), and their chemical composition was detailed using high-performance liquid chromatography with a diode array detector. The cytotoxic activity of the major compounds identified, namely, rosmarinic acid ( 1 ) and abietane diterpenes 7α,6β-dihydroxyroyleanone ( 2 ), 7α-formyloxy-6β-hydroxyroyleanone ( 3 ), 7α-acetoxy-6β-hydroxyroyleanone ( 4 ), and coleon U ( 5 ), was evaluated in a battery of human cancer cell lines, including breast (MDA-MB-231, MCF-7), colon (HCT116), and lung (NCI-H460, NCI-H460/R) cancer, and also in healthy lung (MCR-5) cells. Royleanone ( 3 ) was isolated for the first time from P. madagascariensis , and its full spectroscopic characterization (proton and carbon nuclear magnetic resonance) was accomplished. A high selectivity for lung cancer cells was observed for royleanones ( 2 , 4 ) with selectivity indexes of 4.3 and 3.2, respectively. The observed results combined with literature data allowed the establishment of important structure–activity relationships for substituted royleanone abietanes, such as the requirement for an electron-donating group at positions 6 and/or 7 in the abietane skeleton, and an improved cytotoxic effect for substituents with log P values between 2 and 5.

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