Flavonoids from Stellaria nemorum and Stellaria holostea

Abstract

Stellaria nemorum L. and S. holostea L. (Caryophyllaceae) were investigated for their flavonoids. The new flavonoid 6-C-[(α-arabinopyranosyl)-(1→2)-O-βxylopyranosyl]apigenin (1) and the four known C-glycosides, 6-C-[(α-arabinopyranosyl)-(1→2)-O-β-glucopyranosyl]apigenin (2), apigenin 6-C-βgalactopyranoside-8-C-β-glucopyranoside (3), apigenin 6-C-β-glucopyranoside-8-C-α-arabinopyranoside (4), and apigenin 6-C-β-glucopyranoside-8-C-βxylopyranoside (5) were isolated from the aerial parts of S. nemorum for the first time. Furthemore, five known flavonoids, 3,5,7-trihydroxy-3',5'dimethoxyflavone (9), diosmetin 6-C-β-glucopyranoside (8), schaftoside (4), isoorientin (6) and orientin (7) were obtained from the aerial parts of S. holostea. Compounds 4, 8 and 9 are reported for the first time from this species. The structures of all isolated compounds were unambiguously elucidated by one-and two-dimensional NMR and mass spectral analysis, by acid hydrolysis, as well as by comparison with literature data. The crude extracts of the investigated species exhibited antimicrobial activity against Staphylococcus aureus, while none of the isolated compounds was found to be active.

UHPLC-MS Phytochemical Profiling and Insight into Bioactivity of Rabelera holostea (Greater Stitchwort) Extract

“…Boulliant et al [ 19 ], in one of the pioneer investigations of R. holostea chemical composition, also reported the isolation of apigenin C-glycosides, apigenin 6-C-(6- O -glucosylglucoside)-8-C-glucoside and 6-C-(6- O -glucosylglucoside)-8-C-glucoside. A more recent study by Ancheeva and coworkers [ 1 ], which evaluated and compared methanolic extracts from aerial parts of two species from the genus Stellaria , at that time, S. nemorum and S. holostea ( R. holostea ), showed the presence of luteolin-8-C-β-glucoside (orientin) and luteolin-6-C-β-glucoside (isoorientin) in R. holostea extract. Moreover, three flavonoids: apigenin 6-C-β-glucopyranoside-8-C-α-arabinopyranoside (schaftoside), diosmetin 6-C-β-glucopyranoside, and 3,5,7-trihydroxy-3′,5′-dimethoxyflavone, were also isolated from R. holostea in the same study.…”

“…Rabelera holostea (L.) M. T. Sharples & E. A. Tripp (greater stitchwort, Figure 1 ), formerly known as Stellaria holostea L., belongs to the family Caryophyllaceae, whose members are generally characterized by the presence of C-glycosyl-flavonoids with numerous biological activities [ 1 ]. According to Royal Botanical Gardens (KEW), the native range of this species is Europe up to West Siberia, the Middle East, and Northwest Africa.…”

“…It has a long tradition of ethnopharmacological use in the Eurasian region, mainly for some skin disorders, to treat cuts, bruises, and burns [ 7 ], but also to treat many inflammatory processes, such as digestive, respiratory, and reproductive tracts, bronchitis, asthma, rheumatic pains, arthritis, period pain, diarrhea, measles, and it is also used to reduce swelling [ 5 , 7 , 8 ]. R. holostea (greater stitchwort) is used similarly for the treatment of skin diseases, as an anti-inflammatory agent, but also for its anti-rheumatic, anti-hypertensive, and expectorant properties [ 1 ].…”

Recent Advances on Natural Aryl-C-glycoside Scaffolds: Structure, Bioactivities, and Synthesis—A Comprehensive Review

“…Besides the well-known flavonoid C -glycosides vitexin, isovitexin, orientin, isoorientin, schaftoside, isoshaftoside, neoshaftoside, and their O -glycosylated and or O -acylated derivatives, more and more flavonoid C -glycosides were disclosed. These 6- or 8- C - β -D-glucopyranosides can be divided into five groups: (1) mono- C -glycosylated flavonoids 1 – 3 [ 12 , 37 ], 39 – 42 [ 12 , 13 , 37 ]; (2) 6, 8-di- C -glycosylated flavonoids 4 [ 38 ], 43 [ 39 ]; (3) flavonoid 6- or 8- C - β -D-glucopyranoside-7- O - β -D-glucopyranosides 5 – 10 [ 40 , 41 , 42 , 43 ], 44 [ 44 ]; (4) 2″- or 6″- O -glycosylated flavonoid 6- or 8- C - β -D-glucopyranosides 11 – 31 [ 9 , 38 , 45 , 46 , 47 , 48 , 49 , 50 ], 45 – 55 [ 14 , 51 , 52 , 53 , 54 , 55 , 56 , 57 ]; (5) 2″- or 6″- O -acylated flavonoid 6- or 8- C - β -D-glucopyranosides 32 – 38 [ 10 , 11 , 55 , 56 ], 56 – 80 [ 57 , 58 , 59 , 60 ,…”

“…The sites of C -glycosylation of flavonoid C -xylosides are usually C6 and or C8. Compounds 102 – 106 can be divided into two groups: (1) flavonoid mono- C -xylopyranosides 102 – 103 and (2) di- C -glycosylflavonoids 4 , 43 , 82 , 91 , 104 – 106 [ 38 , 39 , 62 , 69 , 70 ]. All discovered flavonoid C -xylosides are in β configuration.…”