Structural Elucidation of Two New Chromones Isolated from Glasswort<i><b>(Salicornia europaea L.)</b></i>

Arakawa, Yoshihito; Chiji, Hideyuki; Izawa, Masao

doi:10.1080/00021369.1983.10865891

Cited by 13 publications

(20 citation statements)

References 6 publications

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“…Phenylpropanoid substitutions are commonly found in the genus . Methylene‐dioxy arrangement proposed in ( 42 ) is frequently reported in Chenopodiaceae , being also found in S. europaea . LC‐ESI/TOF MS data endorsed the proposed structures (Table ).…”

Section: Resultssupporting

confidence: 60%

“…Flavonoid derivatives (Figure ) – previously isolated from S. europaea , S. fruticosa , S. herbacea , and S. gaudichaudiana – were also detected by the HSCCC and off‐line injection ESI‐MS/MS experiment (Table ). Flavonoid‐aglyca including kaempferol, quercetin, and isorhamnetin, commonly exist in the genus , were found linked to one or two sugar units as well as to C 6 C 3 substituents in a ‘flavonolignan’ ether bridge.…”

Section: Resultsmentioning

confidence: 77%

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Preparative mass‐spectrometry profiling of minor concentrated metabolites in Salicornia gaudichaudiana Moq by high‐speed countercurrent chromatography and off‐line electrospray mass‐spectrometry injection

Costa

Borges

Leitão

et al. 2019

J of Separation Science

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Salicornia species have just been introduced to the European market as a vegetable named ‘samphire’, ‘green asparagus’, or ‘sea asparagus’. Due to its increasing attention, and associated value, minor compounds of Salicornia gaudichaudiana Moq were investigated. The use of countercurrent chromatography and mass spectrometry enabled the search for known, as well as potentially novel natural products. Their identification was achieved based on molecular weights and mass‐spectrometric fragmentation data. Low detection limits enabled the visualization of all compounds with their identification in almost real time close to the preparative countercurrent chromatography experiment. A list of known natural products from Salicornia genus guided the identification process of compounds occurring in Salicornia gaudichaudiana Moq by tandem mass spectrometry fragment comparison. The natural product classes were divided into four groups: chlorogenic acid derivatives; flavonoid derivatives; pentacyclic triterpenoid saponins; and other compounds.

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Section: Resultssupporting

confidence: 60%

Section: Resultsmentioning

confidence: 77%

Preparative mass‐spectrometry profiling of minor concentrated metabolites in Salicornia gaudichaudiana Moq by high‐speed countercurrent chromatography and off‐line electrospray mass‐spectrometry injection

Costa

Borges

Leitão

et al. 2019

J of Separation Science

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“…Of their compounds, betagarin is known to be phytoalexin [52b]. Another flavanone was isolated from the leaves and stems of Salicornia europaea and identified as 2´-OH-6,7-methylenedioxy-flavanone ( Figure 5) [62]. C-Glycosylflavones were reported from nine taxa, i.e.…”

Section: Flavonoids Of Betalain-containing Plantsmentioning

confidence: 99%

“…Two glycosides of betavulgarin, 2´-O-glucoside and 2´-O-xyloside were also isolated from B. vulgaris which was infected to R. solani [52]. 2´-Substituted isoflavonoids, 7,2´-diOH-6-OMe-isoflavone and 5,2´-diOH-6,7methylenedioxy-isoflavone, and 5,3´-diOH-2´-OMe-6,7methylenedioxy-isoflavone, 5,3´-diOH-6,7,8,2´-tetraOMeisoflavone and 5,3´-diOH-7,8,2´-triOMe-isoflavone ( Figure 8) were isolated from Salicornia europaea [62], and Salsola somalensis [61], respectively.…”

Section: Flavonoids Of Betalain-containing Plantsmentioning

confidence: 99%

“…desiccatum Flavonols: Isorhamnetin 3-O-rham-glc-glc, Isorhamnetin 3-O-rut (lv, st) [64]: C. desiccatum var. leptophylloides Flavonols: Quercetin 3,3´-di-O-gly, Quercetin 3-O-fer-xyl-rham-glc, Quercetin 3-O-rham-glc-glc, Quercetin 3-O-rut, Quercetin 3-O-xyl-rham-glc (lv, st) [64]: C. ficifolium Flavonols: Kaempferol (lv) [18], Quercetin (lv, po) [18, 65], Isorhamnetin (po) [65]: C. fremontii Flavonols: Isorhamnetin 3-O-arb, Isorhamnetin 3-O-gal, Isorhamnetin 3-O-glc, Isorhamnetin 3-O-rob, Isorhamnetin 3-O-rut, Kaempferol 3-O-arb, Kaempferol 3-Ogal, Kaempferol 3-O-glc, Kaempferol 3-O-[rham-(1→2)-gal], Kaempferol 3-O-rob, Kaempferol 3-O-sop, Quercetin 3-O-arb, Quercetin 3-O-gal, Quercetin 3-O-glc, Quercetin 3-O-rob, Quercetin 3-O-rut, Quercetin 3-O-sop, Rhamnetin 3-O-glc, Rhamnocitrin 3-O-gal, Rhamnocitrin 3-O-glc (lv) [47]: C. giganteum Flavonol: Quercetin (lv) [9]: C. hians Flavonols: Quercetin 3-O-glc, Quercetin 3-O-rham-glc-glc, Quercetin 3-O-rut (lv, st): C. incognitum Flavonols: Quercetin 3-O-glc, Quercetin 3,3´-di-O-gly, Quercetin 3-O-fer-xyl-rham-glc, Quercetin 3-O-rham-glc-glc, Quercetin 3-O-rut, Quercetin 3-O-xyl-rham-glc (lv, st): C. leptophyllum Flavonols: Quercetin 3,3´-di-O-gly, Quercetin 3-O-fer-xyl-rham-glc, Quercetin 3-O-rham-glc-glc, Quercetin 3-O-rut, Quercetin 3-O-xyl-rham-glc (lv, st) [64]: C. murale Flavonols: Myricetin (lv) [9], Kaempferol, Quercetin (lv, ap) [9, 51a], Herbacetin, Kaempferol 3,7-di-O-rham, Kaempferol 7-O-rham, Kaempferol 3-O-rham-7-O-glc, Kaempferol 3-O-rham-7-O-[xyl-(1→2)-rham] (ap) [51a], Kaempferol 3-O-[apf-(1→4)-rham]-7-O-rham, Kaempferol 3-O-[xyl-(1→4)-rham]-7-O-rham, Kaempferol 3-O-glc-7-O-rham (ap) [51b]: C. opulifolium Flavonols: Kaempferol, Quercetin (lv) [18]: C. pallescens Flavonols: Quercetin 3-O-digly, Quercetin 3-O-xyl-rham-glc (lv, st) [64]: C. pallidicaule Flavonols: Isorhamnetin 3-O-apf-(1→2)-[rham-(1→6)-glc], Isorhamnetin 3-O-rham-(1→2)-[rham-(1→6)-gal], Quercetin 3-O-apf-(1→2)-[rham-(1→6)-gal], Isorhamnetin 3-O-rob, Isorhamnetin 3-O-rut, Kaempferol 3-O-rob, Quercetin 3-O-apf-(1→2)-[rham-(1→6)-glc], Quercetin 3-O-rham-(1→2)-[rham-(1→6)-gal], Quercetin 3-O-rob, Quercetin 3-O-rut (sd) [49]: C. polyspermum Flavonols: Kaempferol, Quercetin (lv) [9]: C. quinoa Flavonols: Kaempferol 3-O-[apf-(1→2)-gal], Kaempferol 3-O-[apf-(1→2)-rham-(1→6)-gal], Kaempferol 3-O-rham-(1→2)-[rham-(1→6)-gal] (sd) [66]: C. subglabrum Flavonols: Isorhamnetin 3-O-rut, Quercetin 3-O-rham-glcglc, Quercetin 3-O-rut (lv, st) [64] Cyathula capitata Flavonol: Quercetin (lv) [9] Deelingia amaranthoides Flavonols: Kaempferol, Quercetin (lv); C-Glycosylflavones: Isoorientin, Orientin (lv) [9] Dysphania littoralis Flavonols: Kaempferol, Quercetin (lv) [9] Gomphrena claussenii Flavonols: Isorhamnetin, Kaempferol, Kaempferol 3-O-glc, Patuletin, Patuletin 3-O-glc, Quercetin (wp) [21]: G. globosa Flavonols: Kaempferol, Quercetin (lv) [9], Gomphrenol (lv) [28]: G. martiana Flavones: Baicalein 5,6-diOMe, Oroxylin A (wp) [23d]; Flavonols: Isorhamnetin 3-O-rob (wp) [23a], 3,5-DiOMe-6,7methylenedioxy-flavone (wp) [23b], 5,7-DiOH-3,6-diOMe-flavone, Galangin triOMe, 3,5,6,7-TetraOMe-flavone (wp) [23c] Hammada scoparia Flavonols: Isorhamnetin 3-O-apf-(1→2)-[rham-(1→6)-gal], Isorhamnetin 3-O-rham-(1→2)-[rham-(1→6)-gal], Isorhamnetin 3-O-[xyl-(1→3)rham-(1→6)-gal] (lv) [50]Honckenya peploides Flavonol: Kaempferol (lv)[9] Iresine celosioides Isoflavonoid: Tlatlancuayin (wp)[27] Kochia scoparia Flavonols: Kaempferol, Quercetin (lv)[9] Pandiaka welwitchii Flavonols: Kaempferol, Quercetin (lv)[9] Rhaquodia nutans Flavonols: Kaempferol, Quercetin (lv)[18] Salicornia europaea Flavanone: 2´-OH-6,7-methylenedioxy-flavanone (lv, st)[62]; Flavonols: Quercetin (lv)[9], Quercetin 3-O-(6´´-mal-glc) (ap)[55]; Isoflavonoids: 7,2´-DiOH-6-OMe-i...…”

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confidence: 99%

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Flavonoid Properties in Plant Families Synthesizing Betalain Pigments (Review)

Iwashina

2015

Natural Product Communications

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The anthocyanin pigments are contained in the flowers, fruits, leaves and roots of almost plant species. On the other hand, distribution of the betacyanins are limited in eight families of the order Caryophyllales, i.e. Aizoaceae, Amaranthaceae, Basellaceae, Cactaceae, Didiereaceae, Nyctaginaceae, Phytolaccaceae and Portulacaceae. However, other flavonoids, i.e. flavones, C-glycosylflavones, flavonols, flavanones, dihydroflavonols, chalcones, aurones, and flavan and proanthocyanidins, are synthesized in betalain-containing families. In this review, distribution and properties of the flavonoids in eight betalain-containing families are described.

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Glassworts as Possible Anticancer Agents Against Human Colorectal Adenocarcinoma Cells with Their Nutritive, Antioxidant and Phytochemical Profiles

Altay

Celep

Yaprak

et al. 2017

Chemistry & Biodiversity

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In this study, the possible uses of glassworts as potential food ingredients and their antiproliferative activity against colorectal adenocarcinoma cells together with their antioxidant and phytochemical profiles were investigated for the first time. MeOH extracts of five different taxa collected from different localities were screened for their antioxidant capacities by DPPH (IC 2.91 - 5.49 mg/ml) and ABTS (24.4 - 38.5 μmol TE/g extract) assays. Salicornia freitagii exhibited the highest DPPH radical scavenging activity. LC/MS/MS analysis displayed that vanillic acid and p-coumaric acid were two main phenolic compounds in the extract. Salicornia freitagii extracts also exhibited high antiproliferative activity against HT-29 (IC 1.67 mg/ml) and Caco-2 (IC 3.03 mg/ml) cells for 72 h. Mineral analysis indicated that all the species with different proportions of elemental components contained high amount of cations. These results indicate that investigated glassworts, with their high phenolic and mineral contents and also notable antioxidant and cytotoxic properties, may be utilized as a promising source of therapeutics.

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Structural Elucidation of Two New Chromones Isolated from Glasswort(Salicornia europaea L.)

Cited by 13 publications

References 6 publications

Preparative mass‐spectrometry profiling of minor concentrated metabolites in Salicornia gaudichaudiana Moq by high‐speed countercurrent chromatography and off‐line electrospray mass‐spectrometry injection

Preparative mass‐spectrometry profiling of minor concentrated metabolites in Salicornia gaudichaudiana Moq by high‐speed countercurrent chromatography and off‐line electrospray mass‐spectrometry injection

Flavonoid Properties in Plant Families Synthesizing Betalain Pigments (Review)

Glassworts as Possible Anticancer Agents Against Human Colorectal Adenocarcinoma Cells with Their Nutritive, Antioxidant and Phytochemical Profiles

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