LC/ES-MS analysis of triterpene glycosides: rapid estimation of the saponin content of dried berries of Phytolacca dodecandra

Perret, C; Wolfender, Jean‐Luc; Hostettmann, Kurt

doi:10.1002/(sici)1099-1565(199909/10)10:5<272::aid-pca470>3.0.co;2-z

Cited by 19 publications

(13 citation statements)

References 7 publications

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“…Recently, it has been demonstrated that LC-ESI/MS can provide a very powerful tool with which to study triterpenes in natural extracts (Schöpke et al, 1996;Fang et al, 1998;Perret et al, 1999;Martinet et al, 2001). In the present paper, the purification and structural determination of triterpenes from the heartwood of Q. robur and Q. petraea employing this technique is reported.…”

Section: Introductionmentioning

confidence: 84%

Identification of triterpene saponins in Quercus robur L. and Q. petraea Liebl. heartwood by LC‐ESI/MS and NMR

Arramon

Saucier

Colombani

et al. 2002

Phytochemical Analysis

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A detailed structural study of the major acidic triterpene saponins from European oak heartwood, Quercus robur L. and Q. petraea Liebl., revealed the presence of 2 alpha,3 beta,19 alpha-trihydroxyolean-12-ene-24,28-dioic acid (1), 2 alpha,3 beta,19 alpha-23-tetrahydroxyolean-12-ene-24,28-dioic acid (2), and their corresponding glycosides, 28-beta-D-glucopyranosyl-2 alpha,3 beta,19 alpha-trihydroxyolean-12-ene-24,28-dioic acid (3), and 28-beta-D-glucopyranosyl-2 alpha,3 beta,19 alpha,23-tetrahydroxyolean-12-ene-24,28-dioic acid (4). Compounds were isolated and purified by successive flash chromatography and semi-preparative HPLC, and structurally determined by NMR and LC-ESI/MS in the negative ion mode. Compounds 2 and 4 have been identified for the first time in Quercus species and are new compounds.

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Section: Introductionmentioning

confidence: 84%

Identification of triterpene saponins in Quercus robur L. and Q. petraea Liebl. heartwood by LC‐ESI/MS and NMR

Arramon

Saucier

Colombani

et al. 2002

Phytochemical Analysis

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“…Such data are prerequisites for further toxicological studies, 20) if saponins from B. aegyptiaca are to be approved as a pesticide, as demonstrated for constituents of Phytolacca dodecandra. [21][22][23][24][25][26][27] Knowledge about their disposition in a water-dwelling snail (target organism) on the other hand, can help better understanding of the mechanisms behind-and treatment regimes needed-using saponins to combat of vector snails for bilharzia. A number of non-mammal freshwater living organisms, such as fish, are also vulnerable to the toxicity of many saponins.…”

Section: Introductionmentioning

confidence: 99%

Preliminary investigation of the disposition of the molluscicidal saponin deltonin from Balanites aegyptiaca in a snail species (Biomphalaria glabrata) and in mice

Brimer

El-Sheikh

Furu³

2007

J. Pestic. Sci.

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A mixture of deltonin and 25-isodeltonin (approx. 1 : 1) was found to be the molluscicidal principle in seeds of Balanites aegyptiaca (L.) Del. The disposition in the schistosomiasis vector Biomphalaria glabrata and in mice was studied. Snails were exposed to 3 H-labelled saponin in water. Administration to mice was oral (O) and intravenous (IV). Snails absorbed the compounds rapidly and showed a high degree of bioaccumulation. The highest concentration was found in the foot followed by the intestines. Snails could excrete the compounds from all organs investigated. Saponin given orally to mice was partly hydrolysed in the intestine, a fraction of genuine and hydrolysed compound being absorbed. Genuine saponin given IV was rapidly distributed to the liver, kidney (medulla), lung and spleen. Compounds did not pass the placenta nor enter the CNS. Excretion was mainly biliary, a minor fraction being excreted in the urine all as genuine compound. About 80% was excreted within 72 hr. While only two (more lipophilic) metabolites were formed in significant amounts by the mice, three such metabolites were seen in extracts of snails. The final toxic agent and the mode of action to target snails remains to be further investigated.

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“…For larger polar molecules such as saponins (MW > 800 Da), CF-FAB or ES are the methods of choice. All these LC/MS interfaces produce soft ionization and the generation of useful fragment information is obtained by tandem mass spectrometry (MS/MS) or by multiple stage MS/MS experiments (MS n ) on ion trap systems (Perret et al, 1999;Martinet et al, 2001). Very recently, high-resolution mass spectrometers such as Q-TOF instruments have also been used for the LC/MS analysis of crude plant extracts allowing the determination of accurate masses on-line.…”

Section: Chemical Screening With Lc-hyphenated Techniquesmentioning

confidence: 99%

Modern Screening Techniques for Plant Extracts

Hostettmann

Wolfender

Terreaux

2001

Pharmaceutical Biology

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In order to discover new bioactive compounds from plant sources which could become new leads or new drugs, extracts should be simultaneously evaluated by chemical screening and by various biological or pharmacological targets. Chemical screening using hyphenated techniques such as LC/UV and LC/MS, and more recently LC/NMR, quickly provides ample structural information, leading in many cases to the identification of compounds. This allows researchers to distinguish between known compounds (dereplication) and new molecules directly from crude plant extracts. Thus, the tedious isolation of known compounds can be avoided, and a targeted isolation of constituents presenting novel or unusual spectroscopic features can be undertaken. In parallel, extracts are also subjected to various bioassays that should be simple, reproducible, and rapid. This approach will be illustrated by the search for new molluscicidal, antioxidant, and antifungal compounds from tropical plants.

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LC/ES-MS analysis of triterpene glycosides: rapid estimation of the saponin content of dried berries of Phytolacca dodecandra

Cited by 19 publications

References 7 publications

Identification of triterpene saponins in Quercus robur L. and Q. petraea Liebl. heartwood by LC‐ESI/MS and NMR

Identification of triterpene saponins in Quercus robur L. and Q. petraea Liebl. heartwood by LC‐ESI/MS and NMR

Preliminary investigation of the disposition of the molluscicidal saponin deltonin from Balanites aegyptiaca in a snail species (Biomphalaria glabrata) and in mice

Modern Screening Techniques for Plant Extracts

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