Identification and Production of Phenolic Nicotiflorin in Astragalus Chrysochlorus Callus

Abstract

Astragalus chrysochlorus Boiss. & Kotschy (2n = 16) is one of the rare Turkish endemic species and it is listed in the Red Data Book of Turkish Plants as endangered. This species has been used traditionally for its wound healing properties and a crude ethanol extract prepared from the roots exhibits antioxidant and cytotoxic activities. In this study, a detailed phytochemical analysis was performed on A. chrysochlorus calli that resulted in the isolation of a major constituent. The purified molecule's structure elucidation was completed by spectral methods [nuclear magnetic resonance (NMR) and mass spectrometry (MS)], which revealed a rarely encountered the flavonoid in the Astragalus genus, nicotiflorin. In order to increasing nicotiflorin content in the callus cultures, the effects of culturing time and elicitor treatment were investigated. The HPLC analyses showed that the maximal production of nicotiflorin occurred with long-term cultured (13 years old) callus as 4775 µg/g dry weight (DW), whereas it was 132 µg/g DW for short-term cultured (2 months old) ones. Then, the 24 h treatment of the yeast extract that was used as biotic elicitor had negative effect on the production of nicotiflorin. The data obtained from this study could be significant for the mass production of nicotiflorin from long term in vitro cultured A. chrysochlorus callus. RezumatAstragalus chrysochlorus Boiss. & Kotschy (2n = 16) este una dintre speciile endemice din Turcia și este încadrată în lista roșie ca fiind pe cale de dispariție. Această specie a fost folosită în mod tradițional pentru proprietățile sale de vindecare a rănilor, iar un extract etanolic a fost preparat din rădăcini și prezintă activitate antioxidantă și citotoxică. În acest studiu s-a efectuat o analiză fitochimică detaliată pe A. chrysochlorus calli care a dus la izolarea unui constituent major. Elucidarea moleculei purificate a fost completată prin metode spectrale (rezonanță magnetică nucleară (NMR) și spectrometrie de masă (MS)), care au evidențiat flavonoidul nicotiflorin. Pentru a crește conținutul de nicotiflorin în culturile de calus, s-au investigat efectele timpului de cultivare și tratamentul elicitor. Analizele HPLC au arătat că producția maximă de nicotiflorin a apărut la calusul de lungă durată (13 ani), 4775 µg/g DW, în timp ce acesta a fost de 132 µg/g DW pentru culturile de scurtă durată (cu vârsta de 2 luni).

Novel Flavonoid Glycosides of Quercetin from Leaves and Flowers of Gaiadendron punctatum G.Don. (Violeta de Campo), used by the Saraguro Community in Southern Ecuador, Inhibit α-Glucosidase Enzyme

“…The 1D and 2D NMR experiments and hydrolysis–GC-MS analysis of glycosides determined that compounds hecpatrin ( 4 ) , gaiadendrin ( 5 ), and puchikrin ( 6 ) had not previously been reported, while nicotiflorin ( 1 ), rutin ( 2 ), and artabotryside A ( 3 ) had already been reported, according to bibliographic comparisons [33,35,36,37].…”

Molecular cloning and biotic elicitation response of phenylalanine ammonia-lyase gene of Astragalus chrysochlorus

“…In our previous study, we showed that a bioactive flavonol glucosides, nicotiflorin, accumulated in callus tissues of A. chrysochlorus which were the starting material of cell suspension cultures in this study (18). PAL is the first enzyme in biosynthesis of phenylpropanoids, that is also the key of secondary phenylpropanoid metabolism in plants (1).…”

“…NMR (nuclear magnetic resonance) analysis demonstrated that a natural flavonoid, a type of bioactive flavonol glucosides, nicotiflorin accumulated in callus tissues of A. chrysochlorus which were the starting material of cell suspension cultures (18). In this study, we have cloned and examined well studied enzyme phenylalanine ammonia-lyase (PAL) belonging to phenylpropanoid pathway, is necessary to upregulate flavonoid biosynthesis in most of the plant species.…”

Chemical constituents from Hibiscus hamabo and their antiphotoaging effects on UVA‐induced CCD‐986sk

“…According to Gwgotek, it regulated the skin inflammatory response upon UVB and UVA exposure and exhibited antioxidant activity as confirmed by tests such as 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) and FRAP. 71,72 Additionally, nicotiflorin (4), astragalin (5), and trans-tiliroside (6) have been reported to exhibit radical scavenging effects 41,61,73 and antiprotozoal activities [74][75][76] and serve as plant metabolites [77][78][79] ; cis-tiliroside (11) also reportedly induces a radical scavenging effect. 80 N-trans-feruloyltyramine (7) is known to act on cyclooxygenase (COX), an in vivo enzyme.…”