Acyclic sesquiterpene oligoglycosides from pericarps of Sapindus mukurossi

Kasai, Ryoji; Fujino, Hiroko; Kuzuki, Tatsuro; Wu-Hsiung, Wong; Goto, Chie; Yata, Noboru; Tanaka, Osamu; Yasuhara, Fujiko; Yamaguchi, Shozo

doi:10.1016/0031-9422(86)80019-x

Cited by 65 publications

(23 citation statements)

References 15 publications

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“…These saponins were not yet described for Sapindus plants. Table 2 (a1 to a9) have been described for S. mukurossi, 7 S. delavayi 8 and S. trifoliatus, 7,22 there is still a lack of description of sesquiterpene glycosides for S. saponaria. In the present work the 1 H NMR spectrum of the crude ASOG fraction showed that these compounds occur in S. saponaria as a complex mixture of acetates (intense singlets at δ 1.90-2.20), confirming the interpretation of the mass spectrum shown in Figure 1.…”

mentioning

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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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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“…The IR spectrum of CPHP indicated the presence of an aromatic system (1627, 1400, 829 and 702 cm −1 ) and an ester moiety (1729 and 1262 cm −1 C NMR data of isolated compound with published data indicated that the isolated compound was a phthalic acid ester derivative [14,25]. The chirality of the C-2′ and C-5′′ centres were assigned following close inspection of the 1 H NMR data [26]. Comparison of the coupling constants for the C-7′ and C-8′′ methyls (J=7.2 Hz) on isolated compound with the known compound di(2S-methyl heptyl)-1,2-benzenedicarboxylate(J=6.5 Hz, S,S configuration at C-2′/C-5′′) (also commonly referred to as di(2S-methyl heptyl)-1,2-benzenedicarboxylate) indicated the configuration on the isolated compound (CPHP) at C-2' and C-5'' was either S,S or R,R [24] (Figure 1).…”

Section: Identification Of 2′′-(methoxycarbonyl)-5′′-methylpentyl 2′-mentioning

confidence: 88%

In-vitro Antiviral Activity of a Novel Phthalic Acid Ester Derivative Isolated from the Bangladeshi Mangrove Fern Acrostichum aureum

Uddin¹,

Bettadapura²,

Guillon

et al. 2013

J Antivir Antiretrovir

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Citation: Uddin SJ, Bettadapura J, Guillon P, Darren Grice I, Mahalingam S, et al. (2013) AbstractBackground: Over the past century dengue (DENV2), chikungunya (CHIKV) and human parainfluenza (hPiV3) viruses have profoundly impacted on human morbidity, mortality and the economy worldwide. Current therapy options to treat infections of these viruses have severe limitations leading to a continued search for novel drug candidates. Acrostichum aureum L. (Pteridaceae) is a mangrove fern, that has been used as a traditional medicine in Bangladesh and other various countries for a variety of diseases including infection.Objectives: Isolation and structural elucidation of novel antiviral secondary metabolites from the methanol extract of the aerial parts of A. aureum. Materials and methods:The novel phthalate acid ester was isolated (HPLC) and structurally elucidated using 1D and 2D NMR, MS and other spectroscopic methods. The compound was tested for antiviral activity against DENV2 andhPiV3in Vero cells using the fluorescent focus (FFA) assay and against CHIKV virus in LLC-MK2 cells using the plaque-forming unit assay (PFU). The activity of the isolated compound was further compared with its known derivative.

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“…Among the principal known saponin constituents of S. rarak, 20,21) significantly suppressed the increase in plasma TG levels 2 h after administration of olive oil at doses of 200 mg/kg, p.o. However, the major acyclic sesquiterpene glycoside, mukurozioside IIb (8) 25) did not show such effect. Consequently, the saponin constituents from S. rarak may be useful for the prevention of obesity.…”

Section: Inhibitory Effect Of Principal Constituents (4 5 8) On Plamentioning

confidence: 90%

Structures of Acetylated Oleanane-Type Triterpene Saponins, Rarasaponins IV, V, and VI, and Anti-hyperlipidemic Constituents from the Pericarps of Sapindus rarak

et al. 2009

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Acyclic sesquiterpene oligoglycosides from pericarps of Sapindus mukurossi

Cited by 65 publications

References 15 publications

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

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

In-vitro Antiviral Activity of a Novel Phthalic Acid Ester Derivative Isolated from the Bangladeshi Mangrove Fern Acrostichum aureum

Structures of Acetylated Oleanane-Type Triterpene Saponins, Rarasaponins IV, V, and VI, and Anti-hyperlipidemic Constituents from the Pericarps of Sapindus rarak

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