Flavonoids enantiomer distribution in different parts of goldenrod (Solidago virgaurea L.), lucerne (Medicago sativa L.) and phacelia (Phacelia tanacetifolia Benth.)

Abstract

Plant material is a rich source of valuable compounds such as flavanones. Their different forms influence bioavailability and biological activity, causing problems with the selection of plant material for specific purposes. The purpose of this research was to determine selected flavanone (eriodictyol, naringenin, liquiritigenin, and hesperetin) enantiomer contents in free form and bonded to glycosides by an RP‐UHPLC‐ESI‐MS/MS method. Different parts (stems, leaves, and flowers) of goldenrod (Solidago virgaurea L.), lucerne (Medicago sativa L.), and phacelia (Phacelia tanacetifolia Benth.) were used. The highest content of eriodictyol was found in goldenrod flowers (13.1 μg/g), where it occurred mainly as the (S)‐enantiomer, and the greatest proportion of the total amount was bonded to glycosides. The richest source of naringenin was found to be lucerne leaves (4.7 μg/g), where it was mainly bonded to glycosides and with the (S)‐enantiomer as the dominant form. Liquiritigenin was determined only in lucerne, where the flowers contained the highest amount (1.2 μg/g), with the (R)‐enantiomer as dominant aglycone form and the (S)‐enantiomer as the dominant glycosylated form. The highest hesperetin content was determined in phacelia leaves (0.38 μg/g), where it was present in the form of a glycoside and only as the (S)‐enantiomer. A comparison of the different analyte forms occurring in different plant parts was performed for the first time.

Solidago virgaurea L.: A Review of Its Ethnomedicinal Uses, Phytochemistry, and Pharmacological Activities

“…Among the flavonoids, rutin, quercetrin, astragalin, nicotiflorin, biorobin, and narcissin have been considered "the most representative" [62], and they are accompanied by their aglycons [49,84]. More recently, flavanones aglycones and glycosides have also been detected and quantified in the different parts of the plant: eriodictyol (the largest amount in the flowers, followed by leaves and then stems, mostly as glycosides), naringenin (similar quantitative distribution in flowers, leaves, and stems, mostly as glycosides), and very small amounts of hesperitin (not assessed separately in each aerial parts) [98]. Eriodictyol and naringenin are present in the form of both R and S enantiomers, whereas hesperitin was detected only as the S enantiomer [98].…”

“…More recently, flavanones aglycones and glycosides have also been detected and quantified in the different parts of the plant: eriodictyol (the largest amount in the flowers, followed by leaves and then stems, mostly as glycosides), naringenin (similar quantitative distribution in flowers, leaves, and stems, mostly as glycosides), and very small amounts of hesperitin (not assessed separately in each aerial parts) [98]. Eriodictyol and naringenin are present in the form of both R and S enantiomers, whereas hesperitin was detected only as the S enantiomer [98]. All flavonoid heterosides seem to be 3-O-glycosides, as for the majority of Solidago species (the notable exception being S. graminifolia (L.) Salisb, in which mono-and di-C-glycosylflavonoids have also been reported [58], but which now is considered a synonym for the Euthamia graminifolia (L.) Nutt [1]).…”

Flavonoid Glycosides from Ulmus macrocarpa Inhibit Osteoclast Differentiation via the Downregulation of NFATc1

“…Among them, diastereoisomers 1 and 2 were obtained in a 3:1 ratio and diastereoisomers 7 and 8 were isolated in a 4:1 ratio. Both pairs of diastereoisomers were for the first time found to co-occur in the genus Ulmus , but it is unsurprising given that flavonoid enantiomers have been characterized in free form or bonded to glycosides in some other plants. − Identification and determination of these diastereoisomers will allow for the selection of a specific pharmaceutical application since most enzymatic reactions acquire high stereoselectivity.…”

Solidago virgaurea L.: A Review of Its Ethnomedicinal Uses, Phytochemistry, and Pharmacological Activities

“…Among the flavonoids, rutin, quercetrin, astragalin, nicotiflorin, biorobin, and narcissin have been considered "the most representative" [64], and they are accompanied by their aglycons [49,95]. More recently, flavanones aglycones and glycosides have also been detected and quantified in the different parts of the plant: eriodictyol (the largest amount in the flowers, followed by leaves and then stems, mostly as glycosides), naringenin (similar quantitative distribution in flowers, leaves, and stems, mostly as glycosides), and very small amounts of hesperitin (not assessed separately in each aerial parts) [102]. Eriodictyol and naringenin are present in the form of both R and S enantiomers, whereas hesperitin was detected only as the S enantiomer [102].…”

“…More recently, flavanones aglycones and glycosides have also been detected and quantified in the different parts of the plant: eriodictyol (the largest amount in the flowers, followed by leaves and then stems, mostly as glycosides), naringenin (similar quantitative distribution in flowers, leaves, and stems, mostly as glycosides), and very small amounts of hesperitin (not assessed separately in each aerial parts) [102]. Eriodictyol and naringenin are present in the form of both R and S enantiomers, whereas hesperitin was detected only as the S enantiomer [102]. All flavonoid heterosides seem to be 3-O-glycosides, as for the majority of Solidago species (the notable exception being S. graminifolia (L.) Salisb, in which mono-and di-C-glycosylflavonoids have also been reported [58], but which now is considered a synonym for the Euthamia graminifolia (L.) Nutt [1]).…”