An Improved Method for The Isolation of the Lignan Constituents of <i>Saururus Cernuus</i> by Reverse Phase Column Chromatography

Rao, Koppaka V.; Oruganty, Ravi Shankar

doi:10.1080/10826079708000478

Cited by 16 publications

(12 citation statements)

References 14 publications

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“…Also known as lizard's tail and breast weed, it has long been used as a folk remedy for inflammation of breasts, kidneys, and bladder (Phares 1867), as a poultice for tumors (Hartwell 1971), and as a sedative (Phares 1867). The chemical constituents responsible for these properties have never been identified, although lignoid natural products with some notable biological activities have been isolated from this plant (Rao & Alvarez 1982Rao et al 1987;Rao & Chattopadhyay 1990;Rao & Reddy 1990;Rao & Oruganty 1997). No ecological functions for these compounds in S. cernuus have been postulated or tested.…”

Section: Methodsmentioning

confidence: 99%

“…( −)-dihydroguaiaretic acid (Rao & Chattopadhyay 1990) and (+)-saucernetin (Rao & Alvarez 1982), the neolignan (−)-licarin A (Rao & Oruganty 1997), and the sesquineolignans (−)-saucerneol (Rao & Alvarez 1983) and (− )-saucerneol methyl ether (Rao & Oruganty 1997). Two novel lignoid natural products, (− )-sauriols A and B, were also identified and were found to share the carbon skeleton of guaiaretic acid, but with different oxidation and methylation patterns.…”

Section: Fig 1 Antifeedant Compounds Of Saururus Cernuusmentioning

confidence: 99%

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Lignoid chemical defenses in the freshwater macrophyte Saururus cernuus

et al. 2001

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Chemical defense against herbivores has rarely been investigated for freshwater plants, possibly due to the common misconception that herbivory on aquatic macrophytes is low and would not select for chemical defenses. In previous work, the freshwater angiosperm Saururus cernuus was shown to be a low preference food for omnivorous crayfish despite its high nutrient value and relatively soft texture. We used feeding by the crayfish Procambarus clarkii to guide fractionation of the deterrent lipid-soluble extract of this plant, leading to the identification of seven deterrent lignoid metabolites, (− )-licarin A, (+ )-saucernetin, (−)-dihydroguaiaretic acid, (− )-sauriols A and B, ( − )-saucerneol, and (− )-saucerneol methyl ether. Lignans have been implicated in terrestrial plant chemical defenses as insect growth inhibitors, insect toxins, nematocides, antibacterial, and antifungal agents. However, these activities have rarely been demonstrated using ecologically relevant methodologies in terrestrial systems, and never before in freshwater systems. The widespread nature of lignans amongst very distantly related plants, along with their rich diversity of molecular structure, suggests that they could play a large role in mediating plant-herbivore interactions. In addition to the lignoid compounds we identified, there were other compounds present in low concentration or unstable compounds that were deterrent, that did not appear to be lignans, but that we were unable to identify. This plant thus appears to be defended by a complex mixture of natural products.

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Section: Methodsmentioning

confidence: 99%

Section: Fig 1 Antifeedant Compounds Of Saururus Cernuusmentioning

confidence: 99%

Lignoid chemical defenses in the freshwater macrophyte Saururus cernuus

et al. 2001

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“…Finally, based on chemical shifts of C-7/C-7', C-8/C-8' and C-9/C-9' and comparison with data described in the literature, 22,23 the isolated neolignans 1-3 displayed a threo configuration between methyl groups. LREIMS of 1-3 displayed peaks in the spectra that corresponded to molecular ions at m/z 326, 328 and 330 consistent, respectively, with molecular masses C 20 [23][24][25] threo-austrobailignan-6 (2) 26 and threo-dihydroguaiaretic acid (3).…”

Section: Resultsmentioning

confidence: 99%

ISOLATION OF CYTOTOXIC NEOLIGNANS FROM Saururus cernuus L. (SAURURACEAE) USING IONIC LIQUID IN THE MICROWAVE ASSISTED EXTRACTION (MAE)

Brito¹,

Camilo²,

Figueiredo³

et al. 2018

Quim. Nova

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In the present work, dried leaves of Saururus cernuus (Saururaceae) were subjected to extraction using an ionic liquid (1-butyl-3-methylimidazolium bromide -BMImBr) in the microwave assisted extraction (MAE). The obtained extract was partitioned using n-hexane and cytotoxicity activity of this organic phase against murine melanoma cell line (B16F10-Nex2) was evaluated in vitro. Since this extract displayed activity (100% of cell death at 200 µg mL -1 ) it was subjected to a bioactivity-guided fractionation to afford four related neolignans: threo-austrobailignan-5 (1), threo-austrobailignan-6 (2), threo-dihydroguaiaretic acid (3) and saucernetin (4). Their chemical structures were established based on NMR and MS spectral analysis. Among the isolated neolignans, compound 2 exhibited the highest cytotoxic activity against HeLa (human cervical melanoma) cells with IC 50 of 28.3 ± 3.9 µg mL ). The obtained results provide important data for the selection of bioactive neolignans with promising cytotoxic potential using a simple and fast method employing a green solvent as 1-butyl-3-methylimidazolium bromide (BMImBr).

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“…Activity-guided chromatographic separation of 80% EtOH extract led to isolation of eleven compounds including three active neolignans (1-3), four flavonoids (4-7), and four aristolactams (8)(9)(10)(11). The structures of 1-11 were identified as manassantin A (1), 27,28) manassantin B (2), 29) (−)-saucerneol (3), 29,30) quercetin-3-O-β-Dglucuronopyranoside (4), 31) quercitrin (5), 32) 33) isoquercitrin (7), 34) saurolactam (8), 35) aristolactam AII (9), 36) piperumbellactam B (10), 37) and aristolactam BII (11) 36) by analysis of spectroscopic data including 1 H-and 13 C-NMR data as well as by comparison of their spectroscopic data with the values reported in the literature (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Anti-proliferative Neolignans from <i>Saururus chinensis</i> against Human Cancer Cell Lines

Lee

Kim

et al. 2012

Biological & Pharmaceutical Bulletin

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Activity-guided fractionation of an 80% EtOH extract from the aerial parts of Saururus chinensis led to isolation of three anti-proliferative neolignans (1-3) along with four flavonoids (4-7) and four aristolactams (8-11). Their chemical structures were identified by analysis of spectroscopic data. All compounds 1-11 were evaluated for their activities against 28 human cancer cell lines using an in vitro cell proliferation assay. Compounds 1-3 showed potent anti-proliferative activities against cervical (C33a, IC 50 0.01 µM for 1; 0.28 µM for 2; 2.80 µM for 3) and lung (NCI-H460, IC 50 0.05 µM for 1; 1.37 µM for 2; 6.46 µM for 3) cancer cells without any remarkable cytotoxic effects on human normal lung cells as a control. Taken together, these data demonstrated the identification of anti-proliferative neolignans which are active components of S. chinensis.

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An Improved Method for The Isolation of the Lignan Constituents of Saururus Cernuus by Reverse Phase Column Chromatography

Cited by 16 publications

References 14 publications

Lignoid chemical defenses in the freshwater macrophyte Saururus cernuus

Lignoid chemical defenses in the freshwater macrophyte Saururus cernuus

ISOLATION OF CYTOTOXIC NEOLIGNANS FROM Saururus cernuus L. (SAURURACEAE) USING IONIC LIQUID IN THE MICROWAVE ASSISTED EXTRACTION (MAE)

Anti-proliferative Neolignans from <i>Saururus chinensis</i> against Human Cancer Cell Lines

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