Rare Flavonoid Aglycones from Anaphalis margaritacea and Two Gnaphalium Species

Wollenweber, Eckhard; Fritz, Hannelore; Henrich, Birgit; Jakupovic, Jasmin; Schilling, Gerhard; Roitman, James N.

doi:10.1515/znc-1993-5-604

Cited by 9 publications

(3 citation statements)

References 16 publications

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“…Merrill was found to excrete the flavone luteolin-3'-Me and several flavonols: galangin, gal-3-Me, gal-7-Me, kaempferol, 8-OH-galangin-8-Me, 8-OH-gal-3,8-diMe, quercetin-3-Me, and qu-3,3'-diMe. Due to the presence of galangin and its derivatives as well as of 8-O-substituted flavonols the flavonoid pattern of this species is similar to those observed in Gnaphalium species, in Cassinia quinquefaria and in Anaphalis margaritacea (Wollenweber et al, 1993a, b).…”

Section: Gnaphalieaesupporting

confidence: 74%

Exudate Flavonoids in Several Asteroideae and Cichorioideae (Asteraceae)

Wollenweber

Dörr

Fritz

et al. 1997

Zeitschrift Für Naturforschung C

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Section: Gnaphalieaesupporting

confidence: 74%

Exudate Flavonoids in Several Asteroideae and Cichorioideae (Asteraceae)

Wollenweber

Dörr

Fritz

et al. 1997

Zeitschrift Für Naturforschung C

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“…To date, 28 flavone derivatives, 1 – 28 , 37 flavonol derivatives, 29 – 65 , one flavanone, 66 , and two chalcone derivatives, 67 , 68 , have been reported, which constitute the majority of the secondary metabolites from the genus Gnaphalium [17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48]. Among them, 28 compounds, 2 – 5 , 7 – 10 , 13 – 16 , 23 , 27 , 28 , 32 – 39 , 41 , 43 – 45 , and 68 , were isolated as O -glycosides.…”

Section: Chemical Constituentsmentioning

confidence: 99%

The Genus Gnaphalium L. (Compositae): Phytochemical and Pharmacological Characteristics

et al. 2013

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Abstract:The genus Gnaphalium, a herb distributed worldwide, comprises approximately 200 species of the Compositae (Asteraceae) family that belongs to the tribe Gnaphalieae. Some species are traditionally used as wild vegetables and in folk medicine. This review focuses on the phytochemical investigations and biological studies of plants from the genus Gnaphalium over the past few decades. More than 125 chemical constituents have been isolated from the genus Gnaphalium, including flavonoids, sesquiterpenes, diterpenes, triterpenes, phytosterols, anthraquinones, caffeoylquinic acid derivatives, and other compounds. The extracts of this genus, as well as compounds isolated from it, have been demonstrated to possess multiple pharmacological activities such as antioxidant, antibacterial and antifungal, anti-complement, antitussive and expectorant, insect antifeedant, cytotoxic, anti-inflammatory, antidiabetic and antihypouricemic properties. The present review compiles the information available on this genus because of its relevance to food and ethnopharmacology and the potential therapeutic uses of these species.

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Flavonoids and triterpenoids from Anaphalis margaritacea

Ren

Shi

2009

Chem Nat Compd

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We have carried out systematical phytochemical studies on several medicinal herbs used in traditional Tibetan medicine growing only at 2500-4000 m above sea level on Qinghai-Tibet Plateau and found that all these plants are abundant in flavonoids [1][2][3][4][5]. The genus Anaphalis (Compositae) is widely distributed in the west and southwest regions of China, and 17 species of them are used as medicinal plants. Anaphalis margaritacea (Linn.) Benth. et Hook. f. has long been used by local inhabitants as a Tibetan medicine for cough and respiratory problems as well as for colds and rheumatism. Previous chemical investigation of this plant only revealed the presence of flavonoids, polyacetylenes, and hydroxylactone [6-9].Herein we report the results of a thorough phytochemical study on flavonoids and triperpenoids from the whole plant of Anaphalis margaritacea (Linn.) Benth. et Hook. f. and their free-radical-scavenging potentials. Isolation of various fractions of the ethanol extract by column chromatography gave 12 known flavonoids. They were apigenin (1) [10], quercetin (2) [2, 8], kaempferol-3-O-β-D-glucopyranoside (3) [9], 3-methylquercetin (4) [5], spiraein (5) [10], 5,7-dihydroxy-3-methoxyflavone (6) [11], 5,7-dihydroxy-3,6,8-trimethoxyflavone (7), 5,7-dihydroxy-3,8-dimethoxyflavone (8), 5,6-dihydroxy-3,7-dimethoxyflavone (9) [4], 3,5-dihydroxy-6,7,8-trimethoxyflavone (10), tiliroside (11) (12) [12], together with four known triterpenoids, ursolic acid (13) [13], 3β-Ο-acetylursolic acid (14) [14], polnolic acid (15) [15], and 19α-hydroxy-3-acetylursolic acid (16) [16]. Their structures were established by direct comparison of their spectroscopic data with the corresponding literature values. Compounds 1-3, 5, 6, 12-16 were isolated from A. margaritacea for the first time. [5] and kaempferol-3-O-[6′′-O-(transp-coumaroyl)-4′′-O-acetyl]-β-D-glucopyranoside1: R 1 = R 3 = R 4 = R 6 = H, R 2 = R 5 = OH; 2: R 1 = R 2 = R 3 = R 5 = OH, R 4 = R 6 = H 3: R 1 = R 4 = R 6 = H, R 2 = R 5 = OH, R 3 = OGlc; 4: R 1 = R 2 = R 5 = OH, R 3 = OMe, R 4 = R 6 = H 5: R 1 = OGlc, R 2 = R 3 = R 5 = OH, R 4 = R 6 = H; 6: R 1 = R 2 = R 4 = R 6 = H, R 3 = OMe, R 5 = OH 7: R 1 = R 2 = H, R 3 = R 4 = R 6 = OMe, R 5 = OH; 8: R 1 = R 2 = R 4 = H, R 3 = R 6 = OMe, R 5 = OH 9: R 1 = R 2 = R 6 = H, R 3 = R 4 = OMe, R 5 = OH; 10: R 1 = R 2 = H, R 3 = OH, R 4 = R 5 = R 6 = OMe 11, 13, 15: R = OH, 12, 14, 16: R = OAc O O R 1 R 2 R 3 OH R 4 R 5 R 6

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Rare Flavonoid Aglycones from Anaphalis margaritacea and Two Gnaphalium Species

Abstract: In stitu t für B otanik der T echnischen H ochschule, S ch n ittsp ah n straß e 3, D-W -6100 D arm sta d t, B undesrepublik D eutschland J. Jakupovic Institut für O rganische Chem ie, FB-5, T echnische U n iv ersität Berlin, Straße des 17. Juni 135,

Cited by 9 publications

References 16 publications

Exudate Flavonoids in Several Asteroideae and Cichorioideae (Asteraceae)

Exudate Flavonoids in Several Asteroideae and Cichorioideae (Asteraceae)

The Genus Gnaphalium L. (Compositae): Phytochemical and Pharmacological Characteristics

Flavonoids and triterpenoids from Anaphalis margaritacea

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