New flavonoids from Punica granatum flowers

Bagri, Priyanka; Ali, Mazhar; Sultana, Shahnaz; Aeri, Vidhu

doi:10.1007/s10600-010-9568-7

Cited by 19 publications

(12 citation statements)

References 9 publications

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“…According to the results (Table 1) and additional 2D NMR experimens performed by us, which agreed with results from an analogous analysis of a similar structure [30], the chemical shifts and SSCC for the protons (characteristic [24] of H-2E, H-3 ax , and H-3 eq ) of the ABX system of flavanone 8 ring C belonged to the 2S-isomer.…”

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confidence: 88%

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New flavanone and other constituents of Helichrysum arenarium indigenous to China

et al. 2011

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A new flavonoid for which the structure (2S) -5,8,4c-trihydroxy-6,7-vinylenedioxyflavanone was established and the known compounds stigmasterol, stigmasterol E-D-glucopyranoside, caffeic acid ethyl ester, and 3,4-methylenedioxycinnamic acid were isolated from Helichrysum arenarium.Keywords: Helichrysum arenarium, triterpenoids, phenylcarboxylic acid derivatives, flavonoids, PMR and 13 C NMR spectra.Helichrysum arenarium L. or everlasting is a perennial medicinal plant that is included in the pharmacopoeias of several European countries and has a long history of use in folk and practical medicine for treating various diseases [1, 2]. Recent research found strong antibacterial and anti-oxidant properties for various extracts of this plant [3][4][5][6].This species of everlasting has a very broad natural distribution because it grows in all regions of Europe, Asia Minor, Central Asia and in the Altai, Mongolia, and China [1].Populations of this plant indigenous to Europe are well studied with respect to their chemistry. It was found that the characteristic secondary metabolites of everlasting are isoprenoids (mono-, sesqui-, di-, and triterpenoids) and phenolic compounds (aromatic phenols and acids, coumarins, phthalides, flavonoids, etc.) [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20].It is well known that the qualitative and quantitative compositions of plant secondary metabolites can change depending on the habitat and vegetation period. Studies of the chemistry of the H. arenarium population indigenous to China were begun because of this and due to its broad use in traditional Chinese medicine [21][22][23].In continuation of the study of the chemical composition of everlasting indigenous to Xinjiang Autonomous Province of the PRC, the known compounds E-sitosterol (1), stigmasterol (2), E-sitosterol E-D-glucopyranoside (3), stigmasterol E-D-glucopyranoside (4), caffeic acid ethyl ester (5), 3,4-methylenedioxycinnamic acid (6), 3,5-dihydroxy-6,7,8-trimethoxyflavonol (7), and the new flavanone 8 were isolated by separation of the total EtOAc extract obtained by work up of the alcohol extract. Flavanone 8 is a yellow crystalline compound with formula C 17 H 12 O 7 , mp 224-225°C, [D] D -77.5°. The IR spectrum of 8 shows absorption bands characteristic of hydroxyls (3298 cm -1 ), carbonyl (1630), and an aromatic ring (1602 and 1498).

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confidence: 88%

“…An ABX system was observed in the PMR spectrum as a doublet of doublets with chemical shifts G 5.43, 3.26, and 2.68 ppm with SSCC characteristic of the H-2E, H-3 ax , and H-3 eq protons of flavanone ring C [24].…”

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confidence: 99%

New flavanone and other constituents of Helichrysum arenarium indigenous to China

et al. 2011

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“…Inhibition of inflammation by pomegranate components involves inhibition of both COX and LOX enzymes (Schubert et al, 1999) and a decline in prostaglandin release from cells (Polagruto et al, 2003). The phytochemical analysis of flower extract also revealed that it contains flavonoids characterized as 5,6,7,8,2′,3′,5′-heptahydroxy-4′-methoxyflavanone (punicaflavanol) and 5,6,7,8,2′,5′hexahydroxy-4′-methoxyflavanone -7-β-D-xylopyranoside (granatumfla vanyl xyloside) (Bagri et al, 2010). Flavonoids are well known for their ability to inhibit pain perception.…”

Section: Discussionmentioning

confidence: 99%

Analgesic and Anti-inflammatory Activities of Flower Extracts of Punica granatum Linn. (Punicaceae)

Sarkar¹

2012

J. App. Pharm. Sci

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Punica granatum has been used for centuries to confer health benefits in a number of inflammatory diseases. Based on its usage in Ayurvedic and Unani medicine, dietary supplements containing pomegranate extract are becoming popular for the treatment and prevention of arthritis and other inflammatory diseases. Pet-ether, dichloromethane and methanol fractions of flower part were chosen for pharmacological screening and analgesic and anti-inflammatory activities in animal model. The anti-inflammatory activity was assessed using the carrageenan-induced rat paw edema model. The analgesic effect was measured in mice using the acetic acid-induced writhing test. In the acetic acid-induced writhing test in mice, pet-ether, dichloromethane and methanol fractions at 200 mg/kg doses level showed 75.77% (p<0.001), 68.56% (p<0.001), 54.64% (p<0.001) inhibition of writhing, respectively. In rat paw edema model induced by carrageenan, pet-ether, dichloromethane and methanol fractions were found to reduce significantly (p<0.001) the formation of edema at the 100 mg/kg dose level and showed 26.92% (p<0.001), 27.97%(p<0.001), 21.85%(p<0.001) inhibition respectively of edema volume at the end of 4 h. Punica granatum possesses evident analgesic and anti-inflammatory activities. The results signify the traditional uses of Punica granatum for inflammation and pain.

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“…Two flavones, luteolin and tricetin, were found in a methanolic extract of pomegranate flowers [ 23 ]. Structures of two flavanones, punicaflavanol (a misnomer; it is a flavanone) and granatumflavanyl xyloside, were elucidated by NMR [ 25 ], while hovetrichoside C (a glycoside of an auronol) and phlorizin (a glycoside of the dihydrochalone phloretin) were identified by IR in pomegranate flowers [ 24 ].…”

Section: Occurrence and Structure Of Diverse Phytochemicals In Pommentioning

confidence: 99%

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum)

2017

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Having served as a symbolic fruit since ancient times, pomegranate (Punica granatum) has also gained considerable recognition as a functional food in the modern era. A large body of literature has linked pomegranate polyphenols, particularly anthocyanins (ATs) and hydrolyzable tannins (HTs), to the health-promoting activities of pomegranate juice and fruit extracts. However, it remains unclear as to how, and to what extent, the numerous phytochemicals in pomegranate may interact and exert cooperative activities in humans. In this review, we examine the structural and analytical information of the diverse phytochemicals that have been identified in different pomegranate tissues, to establish a knowledge base for characterization of metabolite profiles, discovery of novel phytochemicals, and investigation of phytochemical interactions in pomegranate. We also assess recent findings on the function and molecular mechanism of ATs as well as urolithins, the intestinal microbial derivatives of pomegranate HTs, on human nutrition and health. A better understanding of the structural diversity of pomegranate phytochemicals as well as their bioconversions and bioactivities in humans will facilitate the interrogation of their synergistic/antagonistic interactions and accelerate their applications in dietary-based cancer chemoprevention and treatment in the future.

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New flavonoids from Punica granatum flowers

Cited by 19 publications

References 9 publications

New flavanone and other constituents of Helichrysum arenarium indigenous to China

New flavanone and other constituents of Helichrysum arenarium indigenous to China

Analgesic and Anti-inflammatory Activities of Flower Extracts of Punica granatum Linn. (Punicaceae)

Diverse Phytochemicals and Bioactivities in the Ancient Fruit and Modern Functional Food Pomegranate (Punica granatum)

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