Chemical Constituents and Cytotoxic Evaluation of Essential Oils from Leaves of Porcelia macrocarpa (Annonaceae)

Abstract

This work reports the chemical composition and cytotoxic evaluation of the essential oils from three different samples of the leaves of Porcelia macrocarpa R. E. Fries (Annonaceae). The crude oils, obtained by hydrodistillation procedures, were chemically analyzed by GC/MS. The obtained data indicated the predominance of sesquiterpenes (89.8 ± 0.7%), the main compounds being germacrene D (47 ± 1%) and bicyclogermacrene (37 ± 1%). These oils also contained the monoterpene verbanyl acetate (0.5 ± 0.06%) and the diterpene phytol (1.2 ± 0.3%). The crude oils obtained from leaves were pooled and tested in vitro against six cancer cell lineages - murine melanoma (B16F10-Nex2), human glioblastome (U87), human cervical carcinoma (HeLa), human leukemia (HL-60), human colon carcinoma (HCT), human breast adenocarcinoma (SKBr), and human melanoma (A2058), as well as against a non-tumorigenic human cell line (HFF). Since the essential oil reduced more than 50% of the viability of several tumor cells at 100 μg/mL, indicating the presence of active compounds, the crude material was subjected to fractionation over a SiO2/AgNO3 column. This procedure afforded different fractions composed of pure as well as different mixtures of bicyclogermacrene and germacrene D, which were tested against the same tumor cell lines, indicating a significant cytotoxic potential against HL-60 cells. These results suggested that the crude oils and their components, mainly germacrene D, could be used as prototypes for the development of new anti-cancer agents for the treatment of human leukemia.

Chemical Composition and in vitro Cytotoxic and Antileishmanial Activities of Extract and Essential Oil from Leaves of Piper cernuum

“…[16], the essential oil from the leaves of P. cernuum has promising activity against human and murine tumor cell lines, mainly leukemia and colon carcinoma, higher than the positive control (cisplatin). After chromatographic fractionation, compounds 7 -10 showed strong activity against tested cells with germacrene D (9) and (E)-caryophyllene (10) being the most active in agreement with the literature [8] and explaining the activity of the crude oil from leaves of P. cernuum. A comparison of the IC 50 values of the MeOH extract, essential oil and compounds 7-10 against non-tumorigenic HFF indicated reduced selectivities similar to those determined for tumoral cells.…”

Antitumor Properties of the Leaf Essential Oil of Zornia brasiliensis

“…Arunkumar et al [7] isolated a steroid positive compound from Z. diphylla that showed promising in vitro and in vivo anticancer activity to Daltonʼs lymphoma ascites cells and was devoid of any toxicity to mice in a short-term toxicity evaluation, indicating that this genus is a source of cytotoxic compounds. The cytotoxic activity of some major constituents present in the leaf essential oil of Z. brasiliensis has been previously assessed, but they showed IC 50 values > 4 µg/mL [13][14][15][16][17][18][19]. Herein, we confirmed that trans-caryophyllene, α-humulene, and trans-nerolidol presented only weak anticancer potential.…”

Chemical Composition of Four Essential Oils of Eugenia from the Brazilian Amazon and Their Cytotoxic and Antioxidant Activity

“…The germacrane group was also highlighted in the study of the essential oil of Porcelia macrocarpa , another Annonaceae species. A mixture of germacrene D and bicyclogermacrene isolated from its oil showed significant cytotoxic potential against HL-60 cells (human leukemia) [ 40 ]. As mentioned before, the oil of Eugenia caryophyllata (clove) exhibits strong cytotoxic activity in HL-60 cells [ 20 ], as well as being active against colon and melanoma cancer cells [ 41 , 42 ].…”