Isolation and Identification of Two 2,3-Unsubstituted Chromones from Glasswort (<i>Salicornia europaea</i>L.)

Chiji, Hideyuki; AIBA, Takashi; Izawa, Masao

doi:10.1080/00021369.1978.10862940

Cited by 6 publications

(5 citation statements)

References 4 publications

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“…Virtually no experiments have been reported dealing with the formation on C-glycosylation of the chromone nucleus. Aloesin and related compounds differ in their substitution pattern from most other chromones which have a 2-Cmethyl group and a 5-C-phenolic group [68] or are unsubstituted in the pyrone ring [69,70]. Thus, it is difficult to decide whether the aglycones of these compounds are derived from acetate or synthesized via a "mixed pathway".…”

Section: Biosynthesis Of C-glycosyl Chromonesmentioning

confidence: 99%

“…Thus, it is difficult to decide whether the aglycones of these compounds are derived from acetate or synthesized via a "mixed pathway". It is unlikely that they are degradation products of flavonoids [69,70] derivative [71,72]. Mass spectra of a series of anthrone glycosides were studied and compared by PROX [73] and EVANS et al [74].…”

Section: Biosynthesis Of C-glycosyl Chromonesmentioning

confidence: 99%

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Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

Franz

Grün

1983

Planta Med

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compounds with glucuronic acid have been found in mammals, which are probably analogous to C-glycosylated compounds in plants. C-Glucuronides of drugs in man [10] and other mammals [11, 12] represent a novel type of drug metabolite. As regards the biosynthetic pathway which leads to the formation of the carbon-carbon bond in C-glycosides, very little is known. In some cases it is thought that the attachment of the sugar moiety takes place during an early stage of the aglycone formation but definite proof is still missing and cannot be generalized for all groups of the C-glycosides. The aim of this article is to present a short review of the principal structural features and occurrence of the different classes of C-glycosides and further, to discuss the few biosynthetic findings of the C-glycosyl attachment which have been published so far. C-Glycosyl Flavonoids Chemistry of C-glycosyl Flavonoids As it has been pointed out, this group of C-glycosides has been the subject of a still increasing number of reports, which mainly deal with the occurrence and structural investigation of these compounds. Since they have been the subject of several review articles [3, 6, 7, 13, 14] only the main features are given here. At the present over one hundred C-glycosyl flavonoids have been shown to exist in the plant kingdom. The model compound and one of the first to be isolated was vitexin (8-C-3-D-glucopyranosylapigenm) (Fig. 2), the structure of which was established

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Section: Biosynthesis Of C-glycosyl Chromonesmentioning

confidence: 99%

Section: Biosynthesis Of C-glycosyl Chromonesmentioning

confidence: 99%

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

Franz

Grün

1983

Planta Med

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“…Because they are rich sources of protein, vitamins and dietary fibers, essential fatty acids and minerals, they have become beneficial for human nutrition . Glassworts have been reported to be rich sources of antioxidant compounds . The significance of glassworts is not only due to their nutritive values but also they are excellent sources of bioactive compounds, which have therapeutic effects as anticancer, antioxidant, antihyperlipidemic, antidiabetic, and anti‐inflammatory activities .…”

Section: Introductionmentioning

confidence: 99%

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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“…Previous researches of chemical constituents of this plant resulted in the isolation of nine flavonoid compounds and four chromone compounds [2][3][4][5]. In the current research, a new triterpenoid saponin, namely 3E,29-dihydroxy-olean-12-en-28-oic acid 28-O-E-D-glucopyranosyl ester, was isolated from Salicornia europaea Linn., together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-E-D-glucopyranoside (2), 3-O-(methyl-E-D-glucuronopyranosiduronoate)-28-O-E-D-glucopyranosyl oleanolate (chikusetsusaponin IVa methyl ester) (3), 3-O-E-D-glucuronopyranosyl oleanolic acid (calenduloside E) (4), and oleanolic acid 3-O-6c-O-methyl-E-D-glucuronopyranoside (calenduloside E 6c-methyl ester) (5).…”

mentioning

confidence: 99%

“…Previous researches of chemical constituents of this plant resulted in the isolation of nine flavonoid compounds and four chromone compounds [2][3][4][5]. In the current research, a new triterpenoid saponin, namely 3E,29-dihydroxy-olean-12-en-28-oic acid 28-O-E-D-glucopyranosyl ester, was isolated from Salicornia europaea Linn., together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-E-D-glucopyranoside (2) The 13 C NMR spectrum ( Table 1) displayed signals of one hydroxyl-bearing carbon at G 78.1 (3-EOH) and one hydroxymethylene at G 73.7, which gave a correlation in the HSQC spectrum with a 2H-singlet at G H 3.54.…”

mentioning

confidence: 99%

A new triterpenoid saponin and other saponins from Salicornia europaea

Yin

Wang

et al. 2012

Chem Nat Compd

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ester (5), was isolated from Salicornia europaea Linn. Their structures were elucidated on the basis of spectral analysis.Salicornia europaea Linn., marshfire glasswort, is a halophytic plant belonging to the family Chenopodiaceae growing on the sea coasts of temperate and subtropic zones, which has been used in Chinese folk medicine for the treatment of hypertension, cephalalgia, and scurvy [1]. Previous researches of chemical constituents of this plant resulted in the isolation of nine flavonoid compounds and four chromone compounds [2][3][4][5]. In the current research, a new triterpenoid saponin, namely 3E,29-dihydroxy-olean-12-en-28-oic acid 28-O-E-D-glucopyranosyl ester, was isolated from Salicornia europaea Linn., together with four known triterpenoid saponins, i.e., oleanolic acid 28-O-E-D-glucopyranoside (2), 3-O-(methyl-E-D-glucuronopyranosiduronoate)-28-O-E-D-glucopyranosyl oleanolate (chikusetsusaponin IVa methyl ester) (3), 3-O-E-D-glucuronopyranosyl oleanolic acid (calenduloside E) (4), and oleanolic acid 3-O-6c-O-methyl-E-D-glucuronopyranoside (calenduloside E 6c-methyl ester) (5). Their structures were established by spectral analysis. Compound 1 was isolated as a white amorphous powder, [D] 25 D +31.3q (c 0.11, MeOH). Its molecular formula was identified as C 36 H 58 O 9 by HR-ESI-MS at m/z 657.3991 [M + Na] + (calcd 657.3979), indicating the presence of eight degrees of unsaturation. Its 1 H NMR spectrum showed the presence of six tertiary methyl groups (G 0.91, 1.01, 1.08, 1.13, 1.20, and 1.25), a trisubstitued olefinic proton (5.48, t-like), and an anomeric proton signal (6.33, d, J = 8.1 Hz). 1: R = CH 2 OH 2: R = CH 3 3: R 1 = CH 3 , R 2 = Glc 4: R 1 = R 2 = H 5: R 1 = CH 3 , R 2 = H O CH 2 OH OH OH H R HO O O HO

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Isolation and Identification of Two 2,3-Unsubstituted Chromones from Glasswort (Salicornia europaeaL.)

Cited by 6 publications

References 4 publications

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

Chemistry, Occurrence and Biosynthesis ofC-Glycosyl Compounds in Plants

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

A new triterpenoid saponin and other saponins from Salicornia europaea

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