Flavone 8‐C‐Glycosides from Haberlea rhodopensisFriv. (Gesneriaceae)

Abstract

Phytochemical profiling of a MeOH extract from Haberlea rhodopensis by a combination of liquid/liquid extraction, and preparative and semi‐preparative HPLC afforded three new flavone C‐glycosides, hispidulin‐8‐C‐(2″‐O‐syringoyl)‐β‐glucopyranoside (3), hispidulin 8‐C‐(6‐O‐acetyl‐β‐glucopyranoside) (4), and hispidulin 8‐C‐(6‐O‐acetyl‐2‐O‐syringoyl‐β‐glucopyranoside) (5), along with two known phenolic glycosides, myconoside (1) and paucifloside (2). The structures were established by extensive spectroscopic analyses including 1D‐ and 2D‐NMR (COSY, HSQC, and HMBC), and HR‐ESI‐TOF‐MS, and by comparison with published data.

Molecular mechanisms of desiccation tolerance in the resurrection glacial relic Haberlea rhodopensis

“…The obtained data matrix of peak area was normalized using the internal standard (isovitexin, CAS: 29702-25-8). Metabolite identification and annotation were performed using metabolite databases [34] and literature survey of H. rhodopensis [35] and Gesneriaceae species [36]. Peak annotation of detected compounds is shown in Supplemental Table 5 with information on ''Recommendations for Reporting Metabolite Data'' described in [37].…”

Haberlea rhodopensis: pharmaceutical and medical potential as a food additive

“…The presence of flavonoids and tannins, due to the limitations of GC -MS, was not detected (Berkov et al 2011). Phytochemical profiling of methanol extract from H. rhodopensis by combination of liquid/liquid extraction, preparative and semi-preparative HPLC showed two known phenolic glycosides, myconoside and paucifloside, together with three new flavone C-glycosides, hispidulin-8-C-(2 00 -O-syringoyl)-bglucopyranoside, hispidulin 8-C-(6-O-acetyl-b-glucopyranoside), and hispidulin 8-C-(6-Oacetyl-2-O-syringoyl-b-glucopyranoside) (Ebrahimi et al 2011), later confirmed by KondevaBurdina et al (2013). Thus, the biologically active compounds in H. rhodopensis are intensively studied and these experiments should continue further.…”

“…The phytochemical profiling of methanol extract from H. rhodopensis, by using a combination of liquid/liquid extraction, preparative and semi-preparative HPLC, revealed flavone C-glycosides hispidulin-8-C-(2 00 -O-syringoyl)-b-glucopyranoside, hispidulin 8-C-(6-Oacetyl-b-glucopyranoside), hispidulin 8-C-(6-O-acetyl-2-O-syringoyl-b-glucopyranoside), as well as phenolic glycosides myconoside and paucifloside (Ebrahimi et al 2011). A specific fraction was rich in myconoside, a caffeoyl phenylethanoid glycoside with a potential role in the plant survival (Dell'Acqua & Schweikert 2012).…”

“…A specific fraction was rich in myconoside, a caffeoyl phenylethanoid glycoside with a potential role in the plant survival (Dell'Acqua & Schweikert 2012). Paucifloside (Ebrahimi et al 2011), a phenylethanoid glycosidewas also extracted, which possesses antioxidant activity, due to the presence of a caffeoyl and two free hydroxyl groups on phenyl ring (Phakeovilay et al 2013). The antioxidant capacity of the pure compounds myconoside and C-flavone glycosides from H. rhodopensis was studied using DPPH assay, ABTS assay, FRAP and inhibition of lipid peroxidation (LPO) in linoleic acid system.…”

“…The structures of active compounds were established by extensive spectroscopic analyses including 1D and 2D NMR (COSY, HSQC and HMBC), HR-ESI-TOF-MS, and compared with published data (Ebrahimi et al 2011).…”