Flavonoids and saponins from Passiflora edulis f. edulis leaves (purple passion fruit) and its potential anti-inflammatory activity.

OBJECTIVES: The objective of this work was to evaluate the anti-inflammatory activity of the aqueous extract, fractions and major compounds, which are isolated and identified from Passiflora edulis f. edulis (purple passion fruit) leaves extract. METHODS: For the isolation of the major compounds, reversed-phase chromatography and normal phase countercurrent chromatography were used. The separation was followed by thin layer chromatography and HPLC-DAD-ELSD. One-dimensional and two-dimensional NMR and ESI-TOF-MS/MS were used for structural elucidation. The anti-inflammatory activity was evaluated on a TPA multiple dose model of skin chronic inflammation in mice. Additionally, myeloperoxidase (MPO) and nitric oxide synthase (NOS) activity assays were performed as possible mechanisms of action studies. KEY FINDINGS AND CONCLUSIONS: The study of the butanolic fraction mainly showed the presence of saponins and flavonoids. Three minor flavonoids were detected; and three known saponins, cyclopassiflosides IX, XI and III were isolated and identified. This is the first unequivocal report of the presence of these compounds in P. edulis f. edulis leaves. The most favourable results of anti-inflammatory activity were obtained for the flavonoid-rich fraction. All the fractions and isolated compounds evaluated, presented high percentages of inhibition of nitric oxide synthase activity.

Identification of α-Amylase and α-Glucosidase Inhibitors and Ligularoside A, a New Triterpenoid Saponin from Passiflora ligularis Juss (Sweet Granadilla) Leaves, by a Nuclear Magnetic Resonance-Based Metabolomic Study.

The leaves of Passiflora ligularis Juss (known as sweet granadilla for its edible fruits) are a crop byproduct that is discarded. With the aim of contributing to give value-added products from these crop by-side products to farmers of Colombian Andes, we carried out a 1H-NMR-metabolomics analysis of polar extracts from leaves collected in three locations and stored in two conditions in order to identify glucosyl-hydrolase inhibitors. Variations in the metabolic profile and the bioactivity among samples were analyzed by orthogonal partial least square discriminant analysis. Thus, 1H-NMR signals related to polyphenolic compounds, saponins, and amino acids were correlated with higher inhibitory activities. Moreover, a targeted NMR and HPLC-MS/MS analysis allowed the identification of 14 polyphenolic compounds and the structural characterization of a new triterpenoid saponin, ligularoside A. The measurements of IC50 values for α-amylase and α-glycosidase inhibitors allowed the identification of quercetin-3-O-ß-glucoside, kaempferol-3-O-ß-glucoside, and ligularoside A as the most active compounds. These results suggest that P. ligularis leaves are a source of glucosyl-hydrolase inhibitors and lay the foundation for exploring additional applications.

The sedative activity of flavonoids from Passiflora quadrangularis is mediated through the GABAergic pathway.

The aim of this study was to investigate the sedative activity of the aqueous leaf extract of Passiflora quadrangularis, a species that is widely cultivated and consumed in South America, and to identify its main constituents and elucidate the involvement of the GABAergic pathway in its mechanism of action. The bioguided fractionation of the crude extract showed a positive relationship between the sedative activity of the extract and its flavonoids. The methods employed to identify and isolate its main flavonoids resulted in the identification of vitexin-2''-O-xyloside, vitexin-2''-O-glucoside, orientin-2''-O-xyloside and orientin-2''-O-glucoside. Vitexin-2"-O-xyloside, the major flavonoid of the extract, showed sedative activity after oral administration in mice.

New ß-orcinol depsides from Hypotrachyna caraccensis, a lichen from the páramo ecosystem and their free radical scavenging activity.

The new hypotrachynin A (1) and B (2) along with the known (+)-(9b-R)-usnic (3) and methylstictic acids (4) were isolated for the first time from Hypotrachyna caraccensis. Additionally, their potency and reactivity as DPPH• scavengers was determined by a kinetic study calculating their EC50 and second-order rate constants (k2). Considering 1-4 could be dermatological agents, their n-octanol-water partition coefficients and standard molar Gibbs free energies of transfer were calculated as estimation of their lipophilicity and skin penetration. Compounds 1, 3 and 4 were less potent than 2 (EC50 = 3.3014; 1.7540; 2.6652 vs 0.7376) as DPPH• scavengers, in turn 4, was the most reactive with a comparable k2 to the antioxidant BHT (k2 = (232 ± 24) × 10-2 vs (564 ± 12) × 10-2 M-1 s-1, respectively). Since 2 and 4 had an optimal lipophilicity and permeability for skin penetration, they might be developed as topical ingredients to prevent oxidative damage.

Monoaminergic neurotransmission is mediating the antidepressant-like effects of Passiflora edulis Sims fo. edulis.

The genus Passiflora is popularly used to treat anxiety. Recent studies showed antidepressant-like effects of two varieties of P. edulis (edulis and flavicarpa) in mice. However, the mechanisms of antidepressant actions are still unknown. Here, the effects of P. edulis fo. edulis aqueous extract (AE, 100-300mg/kg, po), and ethyl acetate (AcOEt, 25-50mg/kg, po), butanol (BuOH, 25-50mg/kg, po) and residual aqueous (25-100mg/kg, po) fractions were investigated in the mouse forced swimming test. In addition, the involvement of monoamines in the P. edulis fractions-induced antidepressant actions was approached. HPLC analyses showed that AcOEt and BuOH, but not residual, fractions shared with AE the main peaks between 25 and 70min (UV 340nm), which are suggestive of flavonoids. Nortriptyline and fluoxetine reduced the immobility time and similar results were observed for AE, AcOEt and BuOH but not residual fractions. PCPA (inhibitor of 5-HT synthesis), AMPT (inhibitor of catecholamine synthesis) and sulpiride (selective D2 receptor antagonist), but not DSP-4 (noradrenergic neurotoxin), blocked the antidepressant actions of AcOEt and BuOH. In conclusion, AcOEt and BuOH fractions shared with AE similar phytochemical composition and antidepressant actions. Preserved 5-HT and dopamine transmissions were required for the antidepressant effects of P. edulis fractions.

Chemical profiles of traditional preparations of four South American Passiflora species by chromatographic and capillary electrophoretic techniques

ABSTRACT Several species of the genus Passiflora are distributed all over South America, and many of these species are used in popular medicine, mainly as sedatives and tranquilizers. This study analyzes the chemical profile of extracts of four Passiflora species used in folk medicine, focusing on the flavonoids, alkaloids and saponins. We employed simple and fast fingerprint analysis methods by high performance liquid chromatography, ultra performance liquid chromatography and capillary electrophoresis techniques. The analysis led to the detection and identification of C-glycosylflavonoids in all the plant extracts, these being the main constituents in P. tripartita var. mollissima and P. bogotensis. Saponins were observed only in P. alata and P. quadrangularis, while harmane alkaloids were not detected in any of the analyzed extracts in concentrations higher than 0.0187 ppm, the detection limit determined for the UPLC method.

Comparative central effects of the aqueous leaf extract of two populations of Passiflora edulis

ABSTRACTPassiflora edulis Sims, Passifloraceae, has been used in Brazilian traditional folk medicine to the treatment of anxiety and insomnia. P. edulis is commonly known for its economic interests in Brazil. This species exhibits significant variability in the fruit rind color, then two subpopulations has been described (P. edulis fo. flavicarpa O. Deg. (PEF); P. edulis fo. edulis (PEE)). This study compared phytochemical profile and biological actions of aqueous leaf extract of PEE and PEF. HPLC analysis showed marked distinct chromatograms to the P. edulisvarieties. However, in both extracts the major compounds observed were flavonoids C-glycosides. Behavioral studies showed that PEE (300 mg/kg, p.o.) and PEF (100 and 300 mg/kg, p.o.) reduced anxiety in the elevated plus maze test. PEE (300 and 1000 mg/kg, p.o.) and PEF (1000 mg/kg, p.o.) also induced antidepressant-like actions in the forced swimming test. PEE 1000 mg/kg significantly reduced distance moved, thus suggesting sedation. No alterations in sleeping time were observed with PEE and PEF extracts. In conclusion, despite the similarities between the biological actions observed for both P. edulis varieties, quite different phytochemical profile was herein reported. These data suggest that the anxiolytic and antidepressant actions are not due to a specific phytochemical component.

Isolation of C-glycosylflavonoids with α-glucosidase inhibitory activity from Passiflora bogotensis Benth by gradient high-speed counter-current chromatography.

In this study, we applied a gradient High-Speed Counter-Current Chromatography (HSCCC) method that allowed, by direct injection of an aqueous crude extract of the leaves of Passiflora bogotensis, the successful isolation of six flavonoids in a single run, with purity of each compound higher than 81%. This separation enabled the isolation of two new flavonoid glycosides, apigenin-6-C-α-l-rhamnopyranosyl-(1→2)-(6″-O-acetyl)-ß-d-glucopyranoside (2) and luteolin-6-C-α-l-rhamnopyranosyl-(1→2)-(6″-O-acetyl)-ß-d-glucopyranoside (4), and four known ones, isovitexin (1), isoorientin (3), isovitexin-2″-O-rhamnoside (5) and isoorientin-2″-O-rhamnoside (6). The structures of the isolated compounds were identified by HPLC-DAD, LC-MS, (1)H and (13)C NMR and comparison with literature data. The inhibitory activities of all of these compounds were evaluated in vitro on α-glucosidase from S. cerevisiae, and the IC50 was determinate. This is the first study concerning the chemical composition and biological activity of Passiflora bogotensis.

Phytochemical analysis, antioxidant and anti-inflammatory activity of calyces from Physalis peruviana.

Physalis peruviana calyces are used extensively in folk medicine. The crude ethanolic extract and some fractions of calyces were evaluated in order to explore antioxidant and anti-inflammatory activities. The anti-inflammatory activity was evaluated by the TPA-induced ear edema model. The antioxidant in vitro activity was measured by means of the superoxide and nitric oxide scavenging activity of the extracts and fractions. The butanolic fraction was found to be promising due to its anti-inflammatory and antioxidant activities. Therefore, a bio-assay guided approach was employed to isolate and identify rutin (1) and nicotoflorin (2) from their NMR spectroscopic and MS data. The identification of rutin in calyces of P. peruviana supports the possible use of this waste material for phytotherapeutic, nutraceutical and cosmetic preparations.

Passiflora manicata (Juss.) aqueous leaf extract protects against reactive oxygen species and protein glycation in vitro and ex vivo models.

The leaf extracts of many species of genus Passiflora have been extensively investigated for their biological activities on several rat tissues, but mainly in the central nervous system and liver. They posses anxiolytic-like, sedative effects and antioxidant properties. Evidences suggest a key role of C-glycosylflavonoids in the biological activities of Passiflora extracts. Some species (such as P. manicata) of the genus are still poorly investigated for their chemical and biological activity. In this work, we aim to investigate both antioxidant and antiglycation properties of aqueous extract of P. manicata leaves (PMLE) in vitro and ex vivo models. Crude extract showed the C-glycosylflavonoid isovitexin as the major compound. Isoorientin and vitexin were also identified. In TRAP/TAR assay, PMLE showed a significant antioxidant activity. PMLE at concentrations of 10 and 100 µg mL⁻¹ significantly decreasing LDH leakage in rat liver slices. Antioxidant effect also was observed by decreased in oxidative damage markers in slices hence hydrogen peroxide was added as oxidative stress inductor. PMLE inhibited protein glycation at all concentrations tested. In summary, P. manicata aqueous leaf extract possess protective properties against reactive oxygen species and also protein glycation, and could be considered a new source of natural antioxidants.

Fuscoside E: a strong anti-inflammatory diterpene from Caribbean octocoral Eunicea fusca.

The screen of 10 soft coral extracts collected from the Colombian Caribbean Sea in the TPA-induced ear edema model allowed us to identify Eunicea fusca extract among others as an interesting source of active compounds. The new diterpene, fuscoside E (1), along with the known fuscoside B (2), fuscol (3), (+)-germacrene D (4) and a mixture of six sterols (5-10), were isolated from this soft coral. Their structures were elucidated by 1D and 2D NMR spectroscopy techniques. Fuscoside E (1) absolute stereochemistry was determined by chiroptical methods. Fuscoside E (1) and B (2) showed strong anti-inflammatory in the above mentioned bioassay. Additionally, fuscoside E (1) and the sterol mixture (5-10) presented antifouling activity against bacterial strains involved in surface colonization.

Oleanane trietrpenoids from Cedrela montana (Meliaceae).

Two new oleanane-type triterpenes, characterized as 3-oxo-11alpha,12alpha-epoxy-oleanan-28,13beta-olide and 3-oxo-olean-11-en-28,13beta-olide , were isolated from the fruits and seeds of Cedrela montana (Meliaceae). In addition, the known compounds oleanonic acid, a mixture of beta-sitosterol and stigmasterol, and the limonoid photogedunin were also isolated. The structures of the new compounds were established by spectroscopic methods, including 2D NMR.