Phytochemical Analysis of the Fruit Pulp Extracts from Annona crassiflora Mart. and Evaluation of Their Antioxidant and Antiproliferative Activities

Abstract

Annona crassiflora Mart., the marolo fruit of the Cerrado biome, is one of the most frequently consumed species from the Brazilian Midwest. This study aimed to evaluate the chemical composition and the antioxidant and cytotoxic properties of the fruit pulp of A. crassiflora collected at Chapada das Mesas, Maranhão, Brazil. The volatile concentrate was identified as mainly ethyl octanoate, ethyl hexanoate, and methyl octanoate. From the ethanol (LFP-E) and ethyl acetate (LFP-A) extracts were identified phenolic acids (p-coumaric, gallic, quinic, and ferulic), flavones and derivatives (apigenin, epicatechin, 2′-5-dimethoxyflavone, 3′,7-dimethoxy-3-hydroxyflavone, kaempferol-3-O-glucoside and 3-O-rutinoside, quercetin-3-O-glucoside, procyanidin B2, and rutin), aporphine alkaloids (xylopine, stephagine, and romucosine), and acetogenin (annonacin). For the LFP-E and LFP-A extracts, the total phenolic compound values were 15.89 and 33.16 mg GAE/g, the flavonoid compound content values were 2.53 and 70.55 mg QE/g, the DPPH radical scavenging activity showed EC50 values of 182.54 and 57.80 µg/mL, and the ABTS radical activity showed TEAC values of 94.66 and 192.61 µM TE/g. The LFP-E extract showed significant cytotoxicity and cell selectivity for the U251-glioma strain, presenting a GI50 value of 21.34 µg/mL, which is close to doxorubicin (11.68 µg/mL), the standard chemotherapeutic drug. The marolo fruit seems to be a promising source for developing innovative and healthy products for the food industry.

Scientific Advances in the Last Decade on the Recovery, Characterization, and Functionality of Bioactive Compounds from the Araticum Fruit (Annona crassiflora Mart.)

“…The stephalagine was purified by semi-preparative HPLC on RP-C 18 and structurally characterized by high-resolution mass spectrometry, with electrospray ionization (HR-ESI-MS) and nuclear magnetic resonance (NMR) techniques, for the first time by Pereira et al [ 29 ]. Additionally, recent studies have reported the presence of stephalagine in araticum peel and pulp [ 14 , 26 , 27 , 28 , 30 ], indicating that this compound is present in more than a fraction of the fruit. Stephalagine, an aporphine alkaloid, has demonstrated anti-obesity, antinociceptive, and anti-edematogenic effects, suggesting its use as a new potential drug [ 28 , 29 ].…”

“…Stephalagine, an aporphine alkaloid, has demonstrated anti-obesity, antinociceptive, and anti-edematogenic effects, suggesting its use as a new potential drug [ 28 , 29 ]. In addition to stephalagine, other alkaloids, such as xylopine, romucosine, asimilobine, roemerine, nornuciferine, N -methylcoclaurine, guattescidine, actinodaphnine, isoboldine, and N -methyllaurotetanine, have been identified in araticum pulp [ 14 , 22 ]. Several studies demonstrated the presence of liriodenine, atherospermidine, isopiline, isoboldine, isocorydine, anonaine, xylopine, nuciferine, liriodenine, atherospermidine, reticuline, roemerine, nornuciferine, N -methylcoclaurine, guattescidine, actinodaphnine, and N -methyllaurotetanine in the araticum peel [ 22 , 26 , 30 ].…”

“…A series of studies have reported the antioxidant activity of several extracts and fractions obtained from the pulp [ 13 , 14 , 15 , 24 , 25 , 36 , 51 , 52 ], peel [ 16 , 17 , 18 , 23 , 24 , 25 ], and seeds [ 23 , 24 , 25 , 33 , 53 ] of araticum fruit through different in vitro antioxidant assays, including DPPH, TEAC, ORAC, FRAP, β-carotene/linoleic acid system, TBARS, phosphomolybdenum complex, and reducing power. As can be seen in Table 1 , phenolic compounds are the main bioactive compounds reported in these extracts/fractions from araticum fruit parts.…”

“…These GI 50 values were lower than the positive control doxorubicin (GI 50 values of 2.20, 0.05, 5.13, and 1.68 µg/mL for HT-29, NCI-H460, UA251, and NCI-ADR/RES cells, respectively). The effect of hydroethanolic extract (70% ethanol) from araticum pulp on the proliferation of six human cancer cell lines was studied by Carvalho et al [ 14 ]. This extract showed significant antiproliferative activity against only UA251 cells (glioblastoma), with a GI 50 value of 21.34 µg/mL and high tumor cell selectivity, as its GI 50 value for non-tumor cells (HaCaT) was higher than 100 µg/mL.…”

Oligomeric Proanthocyanidins: An Updated Review of Their Natural Sources, Synthesis, and Potentials

“…The natural sources of oligomeric proanthocyanidins include the grape (seed and skin) [33,34], blueberry [35], Annona Crassiflora Mart. [36], coffee [37], polygonaceous plants [38], perennial ryegrass (Lolium perenne L.), and tall fescue (Festuca arundinace Schreb. [39] as shown in Table 1.…”