Guaianolides from Cichorium intybus and structure revision of Cichorium sesquiterpene lactones

Kisiel, Wanda; Zielińska, Klaudia

doi:10.1016/s0031-9422(01)00072-3

Cited by 89 publications

(46 citation statements)

References 12 publications

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“…Feeding diets with condensed tannins increases ultimate-pH in meat (Priolo et al, 2000). More notably, sesquiterpene lactones, found in chicory leaves (Kisiel and Zielińska, 2001), may reduce skatole (3-methyl indole), one of the compounds widely considered to cause boar taint in pork meat. In other research, degradation products of these sesquiterpene lactones, namely dihydrolactucin, tetrahydrolactucin and hydroxypenyacetic acid, were identified as the taint compounds in the milk of dairy cows on high chicory diets (Visser, 1992).…”

Section: Sensory (Eating) Qualitymentioning

confidence: 99%

See 1 more Smart Citation

Stability, fatty acid composition and sensory properties of the M. Longissimus muscle from beef steers grazing either chicory/ryegrass or ryegrass

Marley

Fychan²,

Davies³

et al. 2018

Animal

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Research has shown both production and health benefits for the use of chicory (Cichorium intybus) within ruminant diets. Despite this, little was known about the effects of this forage, containing differing fatty acid profiles and secondary plant compounds compared with ryegrass, on beef stability, fatty acid composition or sensory properties. An experiment was conducted to investigate whether the inclusion of chicory in the diet of grazing beef steers would alter these three properties in the M. Longissimus muscle when compared with beef steers grazing perennial ryegrass (Lolium perenne). Triplicate 2 ha plots were established with a chicory (cv. Puna II)/perennial ryegrass mix or a perennial ryegrass control. A core group of 36 Belgian Blue -cross steers were used within a 2-year beef finishing experiment (n = 6/replicate plot). In the 2 nd grazing year, steers were slaughtered as they reached a target fat class of 3. Muscle pH was checked 2 and 48 h post-slaughter. A section of the hindloin joint containing the M. Longissimus lumborum muscle was removed and a 20 mm-thick steak was cut and muscle samples were taken for analysis of vitamin E and fatty acid analysis. The remaining section of the loin was vacuum packed in modified atmosphere packs and subjected to simulated retail display. A section of the conditioned loin was used for sensory analysis. Data on pH, vitamin E concentration and colour stability in a simulated retail display showed there were no effects of including chicory in the diet of grazing beef steers on meat stability. There were also no differences found in the fatty acid composition or the overall eating quality of the steaks from the two treatments. In conclusion, there were no substantive effects of including chicory in the swards of grazing beef cattle on meat stability, fatty acid composition or sensory properties of the M. Longissimus muscle when compared with beef steers grazing ryegrass-only swards.

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Section: Sensory (Eating) Qualitymentioning

confidence: 99%

“…Chicory leaves contains a range of secondary plant compounds, including sesquiterpene lactones (bitter compounds), tannins and other phenolic compounds (Kisiel and Zielińska, 2001). These dietary plant secondary metabolites have been shown in numerous studies to affect meat quality (Priolo et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Stability, fatty acid composition and sensory properties of the M. Longissimus muscle from beef steers grazing either chicory/ryegrass or ryegrass

Marley

Fychan²,

Davies³

et al. 2018

Animal

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“…The configuration at C-4, C-5, C-6, C-7, and C-8 was determined by NOESY (correlations between H-4 and H-6, H-6 and H-8, H-7 and H-9a were observed) and by comparison of coupling constants with those of naturally occurring germacranolide and guaiane-type sesquiterpenes. [10][11][12] Further confirmation of the structure was made by comparison of data with those of (4bH)-5a-hydroxy-8a-(2-methylpropenoyloxy)-1(10),11(13)-guaiadien-12,6a-olide.3) The relative configuration of the 2-methylbut-2-enoyloxy residue was deduced from coupling constants (Table 1) and by NOE data obtained from NOESY spectrum (Fig. 1).…”

mentioning

confidence: 94%

Further Cytotoxic Sesquiterpene Lactones from Elephantopus mollis KUNTH

Tabopda

Ngoupayo

Liu

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Elephantopus mollis KUNTH, belonging to the Asteraceae, is used in Cameroon for the treatment of cancer, fracture, abdominal pains, defective lactation and snake bite.1) In our continuing search for novel bioactive compounds from Cameroon medicinal plants, we have previously isolated sesquiterpene lactones with cytotoxic activities.2) Sesquiterpene lactones have been isolated from numerous genera of the Asteraceae family and are described as the active constituents of a variety of medicinal plants used in traditional medicine.3-7) Because of an interest in cytotoxic sesquiterpene lactones, the methanol extract of roots and stems of E. mollis was re-examined and three new cytotoxic sesquiterpene lactones, namely, (4bH)-5a-hydroxy-8a-(2-methylbut-2-enoyloxy)-2-oxo-1(10),11(13)-guaiadien-12,6a -olide ( 1 ) , ( 4 b H ) -8 a -( 2 -m e t hy l b u t -2 -e n oy l ox y ) -2 -ox o -1(5),10(14),11(13)-guaiatrien-12,6a -olide (2) and 2,5-epoxy-2b -hydroxy-4a -methoxy-8a -(2-methylbut-2-enoyloxy)-4(15),10(14),11(13)-germacratrien-12,6a -olide (3) were isolated, together with 2b-methoxy-2-deethoxyphantomolin (4),8) molephantin and molephantinin.2)These compounds were evaluated for their cytotoxic activities against neuroblastoma B104. Results and DiscussionThe chloroform extract, which was obtained from methanol extract of the whole bodies of E. mollis, was subjected to repeated column chromatography followed by preparative thin-layer chromatography (TLC) to give three new (1-3) and two known (4, 5) compounds.Compound 1 The connectivity from H-6 to H-9 was confirmed by COSY spectroscopy. Analysis of 2D NMR data (COSY, heteronuclear single quantum correlation (HSQC), HMBC) led to the complete assignment of NMR signals. HMBC correlations of H 3 -15 to C-3, C-4 and C-5 and from H 3 -14 to C-1, C-9, and C-10 revealed that Me-14 and Me-15 are attached to C-10 and C-4, respectively. Further HMBC correlations were observed between H 2 -3 and C-1, C-2, C-4 and C-5 and suggested that compound 1 is a guaiane-type sesquiterpene. The configuration at C-4, C-5, C-6, C-7, and C-8 was determined by NOESY (correlations between H-4 and H-6, H-6 and H-8, H-7 and H-9a were observed) and by comparison of coupling constants with those of naturally occurring germacranolide and guaiane-type sesquiterpenes. [10][11][12] Further confirmation of the structure was made by comparison of data with those of (4bH)-5a-hydroxy-8a-(2-methylpropenoyloxy)-1(10),11(13)-guaiadien-12,6a-olide.3) The relative configuration of the 2-methylbut-2-enoyloxy residue was deduced from coupling constants (Table 1) and by NOE data obtained from NOESY spectrum (Fig. 1).Compound 2 was shown to have the molecular formula ). The 1 H-and 13 C-NMR data (Table 1) were similar to those of 1 with a ketone carbonyl, an a-methylene-gbutyrolactone and a 2-methylbut-2-enoyloxy moiety. However, the quaternary oxygenated carbon observed in compound 1 is replaced by an exomethylene group [d H 5.24, 5.75; d C 122.2 (CH 2 ), 133.5 (C)]. Since an olefin carbon [d C 174.6 (C)] was shifted do...

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“…Avicenna (980-1037) used chicory for treating many diseases. Scientists had thoroughly studied the biochemical composition and properties of raw chicory (Deng et al, 2001;Kisiel and Zielińska, 2001;EI-Lakany et al, 2004;Malarz et al, 2013;Wang et al, 2013;Aisa and Xin, 2015). They consider that the most valuable substances contained in chicory are inulin, lactucin and taraksasterol.…”

Section: Nectar and Pollen Productivity Of Common Chicorymentioning

confidence: 99%

Nectar and Pollen Productivity of Common Chicory

Adamchuk¹,

Bilotserkivets²,

Šimková³

2017

Agrobiodiversity for Improving Nutrition, Health and Life Quality, 2017

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1 AGROBIODIVERSITY f o r i m p r o v i n g n u t r i t i o n , h e a l t h a n d l i f e q u a l i t y 2017There is a need for further study of new and forgotten species of high-yielding plants for the expansion of biodiversity of the forage base of honey bees and the receipt of high-quality commercial products at bee-farms. The aim of research was to explore pollen and honey properties of common chicory (Cichorium intybus L.). The selection of plant samples was carried out in Kyiv, Vinnytsia, Khmelnytsky, Poltava, Sumy, Chernihiv and Kirovohrad regions of Ukraine. Standard statistic and morphometric methods, as well as mathematical formulas were used for determining the biological performance indicators. A long flowering period of common chicory was ascertained in the range from 75 to 102 days. Plant productivity indicators for honey bees were established. Biological nectar productivity was in the range from 92.55 to 190.04 g from one common chicory plant. Honey productivity was in the range from 166.59 to 301.34 kg/ha. The biological pollen productivity of one plant of common chicory was in the range from 1.785 to 3.064 g. As a result of pollen analysis of polyfloral honey obtained during the summer of 2016 the pollen grains of common chicory were found in the range from 1 to 27%. Pollen lumps of common chicory in the range from 10 to 80% of the total fee were in polyfloral bee pollen collected during the summer of 2016. The morphometric parameters of the bee pollen were ascertained: the sharping level of the pollen lump was 4 ±0.15 points, the weight of one pollen lump was 7.21 ±0.255 mg, the length of one pollen lump was 3.42 ±0.048 mm, the width of one pollen lump was 2.97 ±0.070 mm. Our further research in this direction may be conducted to determinate of the biologically active components of cichorium honey and bee pollen.

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Guaianolides from Cichorium intybus and structure revision of Cichorium sesquiterpene lactones

Cited by 89 publications

References 12 publications

Stability, fatty acid composition and sensory properties of the M. Longissimus muscle from beef steers grazing either chicory/ryegrass or ryegrass

Stability, fatty acid composition and sensory properties of the M. Longissimus muscle from beef steers grazing either chicory/ryegrass or ryegrass

Further Cytotoxic Sesquiterpene Lactones from Elephantopus mollis KUNTH

Nectar and Pollen Productivity of Common Chicory

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