Steroidal and triterpenoidal glucosides from Passiflora alata

Reginatto, Flávio Henrique; Kauffmann, Carla; Schripsema, Jan; Guillaume, Dominique; Gosmann, Grace; Schenkel, Eloir Paulo

doi:10.1590/s0103-50532001000100003

Cited by 41 publications

(30 citation statements)

References 15 publications

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“…A ~10-fold purification was achieved. The hemolytic activity, as expected (18,(25)(26)(27), was recovered in the butanol fraction. Moreover, when subjected to HPLC analysis (Figure 7), the hemolysin's profile resembled those of other saponin-containing samples chromatographed under similar conditions (34), thus confirming its saponin nature.…”

Section: Discussionsupporting

confidence: 72%

“…This method is frequently utilized for extracting saponins since the final n-butanol fraction is usually rich in saponins (18,(25)(26)(27). All aqueous and organic extracts were tested for hemolytic activity.…”

Section: Preparation Of a Crude Extract Containing Saponinsmentioning

confidence: 99%

“…Furthermore, saponins have plasma cholesterol-lowering activity (5,12) and are widely utilized as a component of potent adjuvants to boost the immune response (16), principally when complexed with cholesterol (17). However, not all Passiflora species contain saponins in their leaves (18).…”

Section: Introductionmentioning

confidence: 99%

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Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Yuldasheva

Carvalho

Catanho

et al. 2005

Braz J Med Biol Res

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Plants used in traditional medicine are rich sources of hemolysins and cytolysins, which are potential bactericidal and anticancer drugs. The present study demonstrates for the first time the presence of a hemolysin in the leaves of Passiflora quadrangularis L. This hemolysin is heat stable, resistant to trypsin treatment, has the capacity to froth, and acts very rapidly. The hemolysin activity is dose-dependent, with a slope greater than 1 in a double-logarithmic plot. Polyethylene glycols of high molecular weight were able to reduce the rate of hemolysis, while liposomes containing cholesterol completely inhibited it. In contrast, liposomes containing phosphatidylcholine were ineffective. The Passiflora hemolysin markedly increased the conductance of planar lipid bilayers containing cholesterol but was ineffective in cholesterol-free bilayers. Successive extraction of the crude hemolysin with n-hexane, chloroform, ethyl acetate, and n-butanol resulted in a 10-fold purification, with the hemolytic activity being recovered in the n-butanol fraction. The data suggest that membrane cholesterol is the primary target for this hemolysin and that several hemolysin molecules form a large transmembrane water pore. The properties of the Passiflora hemolysin, such as its frothing ability, positive color reaction with vanillin, selective extraction with n-butanol, HPLC profile, cholesterol-dependent membrane susceptibility, formation of a stable complex with cholesterol, and rapid erythrocyte lysis kinetics indicate that it is probably a saponin.

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Section: Discussionsupporting

confidence: 72%

Section: Preparation Of a Crude Extract Containing Saponinsmentioning

confidence: 99%

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Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Yuldasheva

Carvalho

Catanho

et al. 2005

Braz J Med Biol Res

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“…An exogenous saponin, 3-O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-oleanolic acid isolated from Passiflora sp, 23 was used as internal standard for the quantification of free SAPs and ASOGs. A standard curve was produced after injection in the HPLC of five different concentrations of the two analyte respectively against a fixed concentration of the internal standard.…”

Section: Quantitative Analysis Of Glycosidesmentioning

confidence: 99%

Dereplication of glycosides from Sapindus saponaria using liquid chromatography-mass spectrometry

Murgu¹,

Rodrigues‐Filho²

2006

J. Braz. Chem. Soc.

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Frutos de Sapindus saponaria (Sapindaceae), uma planta amplamente distribuída nos trópicos, foram coletados a cada trinta dias, durante seis meses. Estudos usando cromatografia a líquido com detecção por UV e EM (CLAE/UV/ESI-EM) e fragmentações por EM/EM, mostraram que os principais glicosídeos presentes nesses frutos são saponinas (SAP) derivadas dos triterpenos hederagenina e ácido oleanólico, e oligoglicosídeos de sesquiterpenos acíclicos (ASOGs). Usando esses métodos de análise, foram detectados até trinta SAPs e sessenta e três ASOGs. A planta produz esses compostos como uma mistura complexa de glicosídeos naturalmente acetilados de forma não regiosseletiva. Hidrólise alcalina dos glicosídeos naturais produziu uma mistura, constituída de apenas quatro SAPs e cinco ASOGs. Análise quantitativa dos glicosídeos saponificados mostrou que a quantidade de SAPs acumulada durante a maturação dos frutos permaneceu constante (~110 mg g -1 ) enquanto a quantidade de ASOGs é consideravelmente maior e chega a uma acumulação máxima de 540 mg g -1 aos três meses de idade.Fruits of Sapindus saponaria (Sapindaceae), a widespread tree throughout the tropics, were collected each 30 days during six months. Liquid-chromatography with UV and MS detection (LC/UV/ESI-MS) and MS/MS fragmentation studies showed that the main glycosides present in these fruits are saponins (SAP) derived from the triterpenes hederagenin and oleanolic acid, and acyclic sesquiterpene oligoglycosides (ASOGs). Using these methods of analysis, we detected up to thirty SAPs and sixty-three ASOGs. The plant produces these compounds as a complex mixture of naturally non-regiosselective acetylated glycosides. Alkaline hydrolysis of the natural glycosides produced simplified mixtures of compounds formed of only four SAPs and five ASOGs. Quantitative analysis of the saponificated glycosides showed that the amount of SAPs accumulated during fruit maturation was almost constant at ca. 110 mg g -1 while the quantity of ASOGs are considerably higher and hits a maximum accumulation of ca. 540 mg g -1 at an age of ca. 3 months.Keywords: Sapindus saponaria, saponin, sesquiterpene oligoglycoside, electrospray, HPLC IntroductionSapindus saponaria (Sapindaceae) is a medium size tree distributed all over the tropics and produce yearly small fruits in large amounts. These fruits accumulate in its pericarps great quantity of a sap that foam when shaken in water. Many people in the tropics use this sap as a soap substitute, not only for cleaning procedures itself but also for treatment of skin lesions caused by fungi. Also, fruits of S. saponaria contain molluscicidal saponins and can be used for schistosomiasis control.1 The antigastric ulcer potential of extracts obtained from S. saponaria fruits was recently demonstrated. 2Earlier phytochemical studies using fruits of S. saponaria collected in Brazil 1,3,4 led to the identification of five monodesmosidic saponins derived from hederagenin (23-hydroxyoleanolic acid) ( Table 1). Some of these saponins were acylated with acetic...

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“…β-carboline or indole alkaloids (harmane, harmine, and harmol) were also found at low contents in Passiflora species through thin layer chromatography and also using a reversed phase High Performance Liquid Chromatography (Rehwald et al, 1995;Grice et al, 2001). Saponins cyclopassiflosides were found in P. quadrangularis (Orsini et al, 1986(Orsini et al, , 1987, P. alata (Reginatto et al, 2001) and P. edulis (Yoshikawa et al, 2000a,b). Cyclopentanoid cyanohydrin glucosides were found in Passiflora mixta (Bylov et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

Sakalem¹,

Negri²,

Tabach³

2012

Rev. bras. farmacogn.

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Abstract:The diversifi ed genus Passifl ora is well distributed all over Brazil, and many species have been long used as medicinal plants, mainly against anxiety disturbances. This effect has been attributed to its rich fl avonoid composition. Flavonoids' main class, fl avonoid glycosides, has presented central action, particularly as sedativehypnotic, anxiolytic and analgesic. The objective of the present study was to make a phytochemical screening of fi ve little studied Passifl ora species, in order to evaluate their phenolic composition. For this aim, HPLC-DAD-ESI-MS/MS was used. After the preparation of the hydroalcoholic extracts, each species was evaluated by direct injection electrospray ionization (ESI) and tandem mass spectrometry. Although belonging to the same genus, the composition of each species presented particularities; this justifi es the importance of studies aiming for the phenolic composition of different Passifl ora species. Flavones C-glycosides were detected in all extracts, and are found as the main constituents in P. vitifolia, P. coccinea, P. bahiensis and P. sidifolia. In this last one, fl avone-6,8-di-C-glycoside, apigenin-6-C-rhamnosyl-8-C-arabinoside are present in high content. Cyclopassifl osides were found in high content together with cyanogenic glycosides in P. quadrangularis, while in P. coccinea, besides fl avones-Cglycosides were also found procyanidins.

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Steroidal and triterpenoidal glucosides from Passiflora alata

Cited by 41 publications

References 15 publications

Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Cholesterol-dependent hemolytic activity of Passiflora quadrangularis leaves

Dereplication of glycosides from Sapindus saponaria using liquid chromatography-mass spectrometry

Chemical composition of hydroethanolic extracts from five species of the Passiflora genus

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