Flavonol Glycosides from<i>Calendula officinalis</i>Flowers

Vidal-Ollivier, E.; Élias, Riad; Faure, F; Babadjamian, André; Crespin, F.; Balansard, G.; Boudon, G.

doi:10.1055/s-2006-961831

Cited by 68 publications

(46 citation statements)

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“…However, we can find reports of saponin detection, in other plants, in low wavelength range as 210 nm. 15 Derivatization with 4-bromophenacyl bromide has been used, allowing detection at 254 nm, 16 but the additional step required in this techinique involves potential addition of error. Nowadays, no analytical method to quantify saponins has been reported for Ilex paraguariensis and its preparations.…”

Section: Resultsmentioning

confidence: 99%

HPLC method to assay total saponins in Ilex paraguariensis aqueous extract

Gnoatto¹,

Schenkel²,

Bassani³

2005

J. Braz. Chem. Soc.

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Ilex paraguariensis St. Hilaire é uma espécie sul-americana da qual ramos e folhas são utilizados para o preparo de uma bebida de grande consumo em alguns países da América do Sul. A planta é conhecida como "erva-mate" em português ou "yerba-mate" em espanhol. Tendo em vista o potencial uso das saponinas como tensoativo bem como o seu potencial terapêutico, o presente trabalho propõe um método de extração e quantificação para as saponinas presentes em Ilex paraguariensis. As saponinas foram extraídas por decocção, hidrolisadas e quantificadas por CLAE e detecção em UV. A concentração de saponinas foi expressa em ácido ursólico (saponinas totais). O método cromatográfico mostrou linearidade na concentração de 13,5 a 135 µg mL -1 . O extrato aquoso apresentou uma concentração de saponinas totais de 352 µg mL -1 . Os resultados sugerem a possibilidade de adaptação do método para doseamento de saponinas com núcleo triterpênico em extratos de outras plantas.Ilex paraguariensis St. Hilaire is a South American tree from which leaves and twigs are used to prepare a commonly consumed tea in several South American countries. The plant is known as "erva-mate" in Portuguese or "yerba mate" in Spanish. Considering the potential use of the saponins as surfactant as well as its therapeutic potential, the present work was designed to propose extraction and quantitation methods for the saponins present in Ilex paraguariensis. The saponins were extracted by decoction, hydrolyzed and quantified by a HPLC method with UV detection. The saponins concentration was expressed in ursolic acid (total saponins). The method showed linearity for ursolic acid in the range of 13.5 to 135 µg mL -1 . The aqueous extract presented total saponins concentration of 352 µg mL -1 . The results also suggest the possibility of use of similar method for assaying triterpenoid saponins in other plants.Keywords: HPLC, saponins, Ilex paraguariensis, "erva-mate", ursolic acid, saponin quantitation IntroductionIlex paraguariensis St. Hilarie is a South American tree from which leaves and twigs are used to prepare a tea (known as "erva-mate" in Portuguese or "yerba mate" in Spanish), being one of the most commonly consumed beverages in several South American countries, including Brazil (especially in the South states), Uruguay, Paraguay and Argentina. In South America, approximately 30% of the population drinks more than 1 L/day of this beverage. It represents an important crop, with more than 1,400 ton/ year. 1 Besides the substantial amounts of purine alkaloids 2 and caffeoyl-quinic acid derivatives, 3 the leaves of Ilex paraguariensis contain also a significant amount of triterpenoid saponins. Monodesmosidic and bidesmosidic saponins have been isolated from the aerial parts of Ilex paraguariensis, 4-8 all compounds containing the ursolic or oleanolic moieties (Figure 1). These bitter and highly water-soluble compounds are likely to be partially responsible for the taste of the beverage 9 and also for foaming observed in the "mate". Additionally, Ilex paragua...

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Section: Resultsmentioning

confidence: 99%

HPLC method to assay total saponins in Ilex paraguariensis aqueous extract

Gnoatto¹,

Schenkel²,

Bassani³

2005

J. Braz. Chem. Soc.

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“…1-6). Fractions 2-6 were separated by normal-phase and reversed-phase silica gel column chromatography and HPLC to give calendasaponins A (1, 0.0012%), B (2, 0.0024%), C (3, 0.0011%), and D (4, 0.0056%), officinosides A (0.0013%), B (0.0016%), C (0.0028%), and D (0.0028%), glycosides A (5, 2f) 0.090%), B (6, 2f) 0.080%), C (7, 2f) 0.085%), D (8, 2f) 0.0099%), isorhamnetin 3-O-2 G -rhamnosylrutinoside (19,8) 0.024%), and icariside C 3 (20, 10) 0.0006%). A (1), B (2), C (3), and D (4) Calendasaponin A (1) was obtained as colorless fine crystals of mp 226.5-228.6°C from MeOH-H 2 O.…”

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confidence: 99%

“…The 1-butanol-soluble fraction was subjected to normal-phase silica gel column chromatography to provide six fractions . Fractions 2-6 were separated by normal-phase and reversed-phase silica gel column chromatography and HPLC to give calendasaponins A (1, 0.0012%), B (2, 0.0024%), C (3, 0.0011%), and D (4, 0.0056%), officinosides A (0.0013%), B (0.0016%), C (0.0028%), and D (0.0028%), glycosides A (5, 2f) 0.090%), B (6, 2f) 0.080%), C (7, 2f) 0.085%), D (8, 2f) 0.060%), D 2 (9, 2f) 0.030%), F (10, 2f) 0.0091%), calenduloside D (11, 4) 0.0009%), arvensoside A (12, 5) 0.0014%), rutin (13, 6) 0.0025%), quercetin 3-O-neohesperidoside (14, 7) 0.0036%), quercetin 3-O-2 G -rhamnosylrutinoside (15,8) 0.018%), isorhamnetin 3-O-glucoside (16, 9) 0.0015%), isorhamnetin 3-O-rutinoside (17, 7) 0.060%), isorhamnetin 3-O-neohesperidoside (18, 7) 0.0099%), isorhamnetin 3-O-2 G -rhamnosylrutinoside (19,8) 0.024%), and icariside C 3 (20, 10) 0.0006%). [d 5.27 (d-like, 1ٞ-H)].…”

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confidence: 99%

Medicinal Flowers. III. Marigold. (1): Hypoglycemic, Gastric Emptying Inhibitory, and Gastroprotective Principles and New Oleanane-Type Triterpene Oligoglycosides, Calendasaponins A, B, C, and D, from Egyptian Calendula officinalis.

et al. 2001

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The Compositae plant, Calendula (C.) officinalis L., which is commonly called "Marigold", is widely cultivated as an ornamental. The flowers of this plant are very important in European and western Asian folk medicines and are used to treat inflammatory conditions of internal organs, gastrointestinal ulcers, and dysmenorrhea and as a diuretic and diaphoretic in convulsions. This natural medicine is also known to be used externally for inflammation of the oral and pharyngeal mucosa, wounds, and burns. As chemical constituents of C. officinalis, some triterpenes, triterpene oligoglycosides, and flavonol glycosides have been obtained from the flowers. 2)In the course of our studies on the bioactive principles of medicinal flowers, 1,3) we found that the methanolic extract and its 1-butanol-soluble fraction from the dried flowers of Egyptian C. officinalis showed inhibitory effects on the increase of serum glucose levels in glucose-loaded mice, gastric emptying, and ethanol-induced gastric lesions. From the 1-butanol-soluble fraction, we have isolated four new triterpene oligoglycosides called calendasaponins A (1), B (2), C (3), and D (4), two new ionone glucosides named officinosides A and B, and two new sesquiterpene glycosides termed officinosides C and D. This paper deals with the structural elucidation of calendasaponins (1-4). In addition, we describe the inhibitory effects of the glycoside fraction and principal saponin constituents on the increase of serum glucose levels in glucose-loaded mice, gastric emptying, and ethanol-and indomethacin-induced gastric lesions.The dried flowers of C. officinalis cultivated in Egypt were extracted with methanol under reflux. The methanol extract was partitioned into an ethyl acetate-water mixture to furnish the ethyl acetate-soluble fraction and water phase. The water phase was further extracted with 1-butanol to give a 1-butanol-soluble fraction (the glycoside fraction) and water-soluble fraction. The methanolic extract was found to exhibit inhibitory activity on the increase of serum glucose levels in glucose-loaded mice after a single oral administration of 1000 mg/kg. In the same bioassay, the 1-butanol-soluble fraction showed potent activity at a lower dose (500 mg/kg), as shown in Table 1. As shown in Table 2, the methanolic extract also inhibited gastric emptying in carboxymethyl cellulose sodium salt (CMC-Na) meal-loaded mice after an oral application (500, 1000 mg/kg). The 1-butanol-soluble fraction showed a potent inhibitory effect on gastric emptying at lower doses (250, 500 mg/kg). Furthermore, these extracts were found to show a potent gastroprotective effect in rats (Table 3). Namely, the methanolic extract inhibited gastric lesions induced by ethanol after an oral application (100, 200 mg/kg) in rats, while the 1-butanol-soluble fraction was found to completely inhibit ethanol-induced gastric lesions at a 100 mg/kg dose. On the other hand, the methanolic extract and 1-butanol-soluble fraction completely inhibited indomethacin-induced gastric lesions. The 1...

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“…This may be attributed to the previously reported sitosterol, stigmasterol, taraxasterol, lupeol, faradiol 3-O-Laurate in addition to quercetin isoquercetin and calendoflaside (Vidal-Ollivier et al, 1989).…”

Section: Discussionmentioning

confidence: 72%

Antioxidant and anti-listerial activities of selected Egyptian medicinal plants

Bakr¹,

Omer²,

El-Razik³

et al. 2013

Afr. J. Microbiol. Res.

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This work investigates the phenolic, antioxidant capacity of crude extracts of eight Egyptian medicinal plants (Syrian oregano, marjoram, rosemary, lemongrass, thyme, yarrow, marigold and sweet wormwood) and estimates their activity against Listeria monocytogenes, one of the most virulent food borne pathogens. Antioxidant activity of Rosemary (70.6±1.65%) and thyme (70.8±1.72%) based on TBA assay was significantly higher compared to other plants and ascorbic acid. Rosemary was found to possess the best antilisterial activity with lowest MBC (8 µl/ml); while its total phenolic content (TPC) represented 69.73 ± 0.47 mg/g GAE. Thyme showed MBC of 46 µl/ml with TPC 96.85±0.56 mg/g GAE. Lemon grass and marigold showed considerable antilisterial activity (MBC 31, 46 µl/ml respectively), although they had lower phenolic contents and low thiobarbituric acid inhibition. Sweet wormwood, marjoram and yarrow were inactive against listeria. Rosemary and thyme appeared as possible alternatives for synthetic food additives and preservatives.

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Flavonol Glycosides fromCalendula officinalisFlowers

Cited by 68 publications

References 0 publications

HPLC method to assay total saponins in Ilex paraguariensis aqueous extract

HPLC method to assay total saponins in Ilex paraguariensis aqueous extract

Medicinal Flowers. III. Marigold. (1): Hypoglycemic, Gastric Emptying Inhibitory, and Gastroprotective Principles and New Oleanane-Type Triterpene Oligoglycosides, Calendasaponins A, B, C, and D, from Egyptian Calendula officinalis.

Antioxidant and anti-listerial activities of selected Egyptian medicinal plants

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