Friedelane Triterpenes with Cytotoxic Activity from the Leaves of Maytenus quadrangulata (Celastraceae)

Abstract

Three new triterpenes, 3,4-seco-3,11β-epoxyfriedel-4(23)-en-3β-ol (1), friedelan- 3α,11β‑diol (2), 7β,26-epoxyfriedelan-3a,7a-diol (3), a mixture of two new triterpenes 3a-hydroxyfriedelan-29-yl palmitate (4) and 3α-hydroxyfriedelan-29-yl stearate (5) and eleven known compounds were obtained from the hexane extract of Maytenus quadrangulata leaves. The structures and the relative stereochemistry of the new triterpenes were established through 1D/2D nuclear magnetic resonance (NMR), high resolution mass spectrometry (HRMS), and Fourier transform infrared (FTIR) spectral data. The hexane extract and isolated compounds were submitted to the cytotoxicity assays against leukemia (THP-1 and K562), ovarian (TOV-21G) and breast cancer (MDA-MB-231) cell lines. Compounds 1, 2 and 11β-hydroxyfriedelan-3-one (15) displayed high cytotoxicity and selectivity against leukemic cells when compared to positive control cytarabine (for THP-1) and imatinib (for K562). Furthermore, compound 2 showed similar cytotoxicity and an enhanced selectivity towards ovarian and breast cells in comparison to positive control etoposide.

Phytochemical Characterization of Cannabis sativa L. Roots from Northeastern Brazil

“…[18] Friedelan-3-one exhibits antiproliferative, antioxidant, anti-inflammatory, analgesic and antipyretic activities. [31] The compounds epifriedelanol and friedelan-3-one were identified in C. sativa roots at a concentration of 21.3 and 12.8 mg/Kg of plant material, respectively. [10] Lima et al [9] demonstrated in their study the antiinflammatory and anti-asthmatic potential of the aqueous extract of C. sativa roots in mice, which suggests that such potential can be attributed to the presence of the compounds identified in this study.…”

“…Studies performed with the pentacyclic triterpene epifriedelanol showed that the compound possesses antibacterial activity [18] . Friedelan‐3‐one exhibits antiproliferative, antioxidant, anti‐inflammatory, analgesic and antipyretic activities [31] . The compounds epifriedelanol and friedelan‐3‐one were identified in C. sativa roots at a concentration of 21.3 and 12.8 mg/Kg of plant material, respectively [10] …”