Ceramides and cytotoxic constituents from Ficus glumosa Del. (Moraceae)

Abstract

A investigação química da casca do caule de Ficus glumosa (Moraceae) deu origem a duas novas ceramidas (2R,7E)-2-hidróxi-N-[(2S,3S,4R)-1,3,4-trihidróxihexadecano--dihidróxiheptadec-9-eno-2-il}-2-hidróxipentacosanamida, em conjunto com vinte e um compostos conhecidos. As estruturas foram estabelecidas usando-se dados de RMN, espectrometria de massas, transformação química e por comparação com dados relatados. Vinte e um compostos foram posteriormente testados contra células de câncer de próstata PC-3 e seis deles revelaram efeito citotóxico. Dongnósido E foi o composto mais ativo, com IC 50 de 0,75 µmol L -1 contra células de câncer PC-3, enquanto o medicamento de referência doxorrubicina, apresentou IC 50 de 0.91 µmol L -1 . Este composto também demonstrou inibir o crescimento de células do câncer de fibrossarcoma HT1080 (IC 50 0,7 µmol L -1 ). Chemical investigation of the stem bark of Ficus glumosa (Moraceae) yielded two new ceramides (2R,7E)-2-hydroxy-N-[(2S,3S,4R)-1,3,4-trihydroxyhexadecan-2-yl]hexacos-7-enamide and (2R)-N-{(2S,3S,4R,9Z)-1-O-[(β-D-glucopyranosyl]-3,4-dihydroxyheptadec-9-en-2-yl}-2-hydroxypentacosanamide together with twenty one known compounds. The structures were established using NMR data, mass spectrometry, chemical transformation and by comparison with the reported data. Twenty one compounds were further tested against the prostate cancer PC-3 cell line and six of them revealed cytotoxic effect. Dongnoside E was the most active compound with an IC 50 0.75 µmol L -1 against the cancer cells line PC-3 while the reference drug doxorubicin displayed 0.91 µmol L -1 . This compound also proved to inhibit the cell growth of the fibrosarcoma cancer HT1080 (IC 50 0.7 µmol L -1 ).

Isolation and characterization of novel acetylcholinesterase inhibitors from Ficus benghalensis L. leaves

“…These compounds were already reported from F. elastica, F. mucuso, and F. glumosa, respectively. 39,32,40 In the same context, lactone chlorines with the molecular formula C 55 H 74 N 4 O 6 were characterized as cuschlorine A (16) and B (17) that was previously detected in F. microcarpa. 41…”

Ficusplants: State of the art from a phytochemical, pharmacological, and toxicological perspective

“…However, at 50 μg/ml, it inhibits the proliferation of examined human liver (HepG2) cancer cell line (Ragab et al, 2013). of 0.7 μM (Nana et al, 2012).…”

A Pharmacological Overview of Alpinumisoflavone, a Natural Prenylated Isoflavonoid

“…At the concentration of 10 µM, the growth and invasion of the human clear-cell renal carcinoma ccRCC 786-O and Caki1 cells were suppressed by 40 and 50–60%, respectively (Wang et al, 2017a). An IC 50 value of >25 μM was obtained against human prostate PC-3 (Nana et al, 2012) and neuroblastoma SH-SY5Y (Hong et al, 2018) cancer cells. At the concentration of 10 −5 M, AIF inhibited the growth of the renal SN12C cancer cells by 32.67% (Amen et al, 2013).…”

“…The inclusion of positive controls in respective studies of natural compounds is indispensable in good experimental practice (Ateba et al, 2018). Among the 13 in vitro studies recorded in this review, only one investigated the effects against normal cells (Kumar et al, 2013) and four used a positive control (Nana et al, 2012; Tjahjandarie and Tanjng, 2015a; Hu et al, 2017; Hong et al, 2018). In addition to this deficit, human tumor cell lines as the workhorse of cancer research are cultured since decades and do not adequately mirror (different tumor environment) the biology of human tumors (Ben-David et al, 2017).…”