Isolation of a flavonoid, apigenin 7-O-glucoside, from Mentha longifolia (L.) Hudson subspecies longifolia and its genotoxic potency

Mohammed

BMC Complement Altern Med

et al. 2014

BackgroundWaterlily Mango (Mangifera indica L.) is thought to be antioxidant-rich, conferred by its functional phytochemicals.MethodsThe potential anticancer effects of the ethanolic kernel extract on breast cancer cells (MDA-MB-231 and MCF-7) using MTT, anti-proliferation, neutral red (NR) uptake and lactate dehydrogenase (LDH) release assays were evaluated. Cytological studies on the breast cancer cells were also conducted, and phytochemical analyses of the extract were carried out to determine the likely bioactive compounds responsible for such effects.ResultsResults showed the extract induced cytotoxicity in MDA-MB-231 cells and MCF-7 cells with IC50 values of 30 and 15 μg/mL, respectively. The extract showed significant toxicity towards both cell lines, with low toxicity to normal breast cells (MCF-10A). The cytotoxic effects on the cells were further confirmed by the NR uptake, antiproliferative and LDH release assays. Bioactive analyses revealed that many bioactives were present in the extract although butylated hydroxytoluene, a potent antioxidant, was the most abundant with 44.65%.ConclusionsM. indica extract appears to be more cytoxic to both estrogen positive and negative breast cancer cell lines than to normal breast cells. Synergistic effects of its antioxidant bioactives could have contributed to the cytotoxic effects of the extract. The extract of M. indica, therefore, has potential anticancer activity against breast cancer cells. This potential is worth studying further, and could have implications on future studies and eventually management of human breast cancers.

Section: Resultsmentioning

confidence: 99%

Cytotoxic effects of Mangifera indica L. kernel extract on human breast cancer (MCF-7 and MDA-MB-231 cell lines) and bioactive constituents in the crude extract

Mohammed

BMC Complement Altern Med

et al. 2014

“…1 H-NMR (500 MHz) and 13 C-NMR (125 MHz) spectrawere measured on a Bruker AM500 FT-NMR spectrometer. The Electrospray Ionization -Mass Spectroscopy (ESI-MS) spectra were obtained from an Agilent 1260 series single quadrupole LC/MS system.…”

Section: General Experimental Proceduresmentioning

confidence: 99%

“…This β-D-glucopyranosyl residue was determined to attach on carbon C-7 of the flavonoid ring system by the HMBC correlations of anomeric proton signal [δ H 5.47 (H-1'')] to carbon C-7 (δ C 162.97). Based on the NMR data and comparison of the data given in the literature, the structure of compound 5 was identifed as apigetrin ( Figure 1) [13]. This compound has antioxidant properties as well as immunomodulating effects upon splenocytes, NK and CTL cells, and macrophages [14].…”

Section: 5mentioning

confidence: 99%

“…1 H-NMR (500 MHz, DMSO-d 6 ) and13 C-NMR (125 MHz, DMSO-d 6 ), seeTable 1; ESI-MS: m/z 617 [M+Na] + , 593 [M-H] -(C 27 H 30 O 15 , M = 594).Kaempferol (3): yellow powder; 1 H-NMR (500MHz, CD 3 OD-d 4 )  H (ppm): 8.10 (2H, d, J = 8.5 Hz, H-2', H-6'), 6.93 (2H, d, J = 8.5 Hz, H-3', H-5'), 6.20 (1H, d, J = 2.0 Hz, H-6), 6.42 (1H, d, J = 2.0 Hz, H-8); 13 C-NMR (125 MHz, CD 3 OD-d 4 ) see Table 2; ESI-MS m/z: 285 [M-H] -, 287 [M+H] + (C 15 H 10 O 6 , M = 286). Quercetin (4): yellow amorphous powder; 1 H-NMR (500 MHz, CD 3 OD-d 4 )  H (ppm): 7.76 (1H, s, H-2'), 7.66 ( 2H, d, J = 8.5 Hz, H-6'), 6.91 (2H, d, J = 8.5 Hz, H-5'), 6.41 (1H, s, H-8), 6.21 (1H, s, H-6); 13 C-NMR (125 MHz, CD 3 OD-d 4 ) see table 2; ESI-MS m/z: 301 [M-H] -(C 15 H 10 O 7 , M = 302).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Flavonoids From the Leaves of Aralia Hiepiana

Phan

Thuan

Hiền

et al. 2018

JST

Aralia hiepiana J.Wen & Lowry (Araliaceae), a new species from southern Vietnam, is described and illustrated by J. Wen & Lowry in 2002. Up to now, there are not any chemical data from this endemic species. By various chromatography methods, four flavonoids compounds namely kaempferol 3,7-O-α-L-dirhamnopyranoside (1), kaempferol 3-O-β-D-glucopyranosyl-7-O-a-L-rhamnopyranoside (2), kaempferol (3), quercetin (4), apigenin 7-O-β-glucopyranoside (5) were isolated from the methanol extract of leaves of Aralia hiepiana collected in Da Lat, Lam Dong province. Their structures were elucidated using 1-D and 2-D NMR techniques and by comparison with the literature data. This is the first time to isolate these compounds from Aralia hiepiana.

“…Two compounds, apigenin-7-O-β-D-glycoside (molecular formula C 21 H 20 O 10 ) (Gulluce et al 2015;Peng et al 2016) and isorhoifolin (apigenin 7-O-rutinoside, 4',5,7-trihydroxyflavone 7-O-rutinoside; molecular formula C 27 H 30 O 14 ) (Kokotkiewicz et al 2012) (Fig. 1), were isolated as yellow powders, which gave strongly UV absorbing bands on TLC at 254 nm and turned to yellow with vanillin spray reagent.…”

Section: Structure Characterization Of Acaricidal Compoundsmentioning

confidence: 99%

Isolation and characterization of two acaricidal compounds from Calpurnia aurea subsp. aurea (Fabaceae) leaf extract

et al. 2018

The menace caused by ticks and tick-borne diseases is a major limitation to the livestock industry in Africa. The high costs and non-availability of synthetic, chemical acaricides to resource-limited farmers, resistance of ticks to available acaricides and residue problems in meat and milk consumed by humans further complicate matters. The use of plant extracts as a possible source of new acaricides has received much interest in the last decade. In our endeavour to discover natural acaricidal compounds, tick toxicant bioassays were conducted and the chloroform fraction of Calpurnia aurea ethanol leaf extract had good acaricidal activity. Further purification of the fraction revealed two flavonoids, isolated from C. aurea for the first time. These flavonoids were characterized as apigenin-7-O-β-D-glycoside and isorhoifolin by means of NMR spectroscopic and mass spectrometry analysis. Isorhoifolin was the most potent compound (LC = 0.65 mg/ml), was not cytotoxic and should be further investigated for its potential as an acaricidal agent.