New chlorogenic acid derivatives and triterpenoids from Scorzonera aucheriana

Abstract

Chromatographic separation of n-hexane and ethyl acetate fraction of a crude methanol extract obtained from aerial parts of the Scorzonera aucheriana DC collected from Sivas province of Turkey yielded nine natural compounds, including two new 3caffeoyl-quinic acid analogs (1-2), and one new taraxasterol oleate (3), as well as six known triterpenoids taraxasterol (4), taraxasterol acetate (5), ptiloepoxide (6), lupeol (7), lupeol acetate (8), and β-sitosterol (9) were characterized. The structures of the 2 isolated compounds were elucidated on the basis of NMR (1 H, 13 C, COSY, HMBC, HSQC, and TOCSY), UV, FT-IR and LC-Q-TOF-MS spectrometric data.

Phytochemical Composition and Biological Activities of Scorzonera Species

“…Samples of S. aucheriana were collected in central Turkey and aerial parts were extracted with methanol at room temperature [ 7 , 29 ].…”

“…Investigation on aerial parts of the plant led to the isolation of dihydroisocoumarins and dihydroisocoumarin derivatives (scorzopygmaecoside, scorzocreticoside II, iso-scorzopygmaecoside, scorzoaucherioside I and II), quinic acid derivatives (3,5- O -dicaffeoyl- epi -quinic acid and 3,5- O -dicaffeoylquinic acid), and 3,4-dihydroxyphenyl caffeate [ 7 ]. In another study, chlorogenic acid derivatives (methyl 1-(2-methylcyclopropyl-1-carbonyloxy)chlorogenate and 3,4-bis[(3′,4-dioxo-1′,3′,5′,6′-tetrahydrospiro[cyclohexa-2,5-diene-1,4′-cyclopenta[ c ]-furan]-1′-yl)]chlorogenic acid), triterpenoids (taraxasterol, taraxasterol acetate, taraxasterol oleate, lupeol, lupeol acetate and ptiloepoxide) and β-sitosterol were isolated from the methanol extract of S. aucheriana aerial parts [ 29 ].…”

“…Biennial plants or dwarf subshrubs are rare [ 19 ]. Plants within the genus Scorzonera are reported to contain flavonoids [ 12 , 13 , 22 , 23 , 24 ], phenolic acid derivatives [ 8 , 13 , 25 , 26 ], triterpenoids [ 18 , 23 , 27 , 28 , 29 , 30 , 31 ], sesquiterpenoids [ 14 , 17 , 20 , 32 , 33 , 34 ], dihydroisocoumarins [ 7 , 35 , 36 , 37 ], and other bioactive compounds. Scorzonera species have been commonly used as medicinal plants in European and Asian herbal therapy for ages.…”

A Comprehensive Study on a Medicinal and Edible Plant Scorzonera incisa DC., Discussing the Natural Limits of Phytochemical Profiling

“…However, results revealed that the majority of the PE fraction is consisted of triterpenoids. Among them, the most abundant peaks belonged to ß‐amyrin, lupeol, 13,27‐cycloursan‐3‐ol‐acetate, two cholestane derivatives, taraxasterol, germanicol, and lupeyl acetate which were previously reported from different Scorzonera species [28,38–40] . Particularly, taraxasteryl acetate, olean‐12‐en‐11‐one‐3‐acetyl, lupeol, and lupeyl acetate were reported from S. incisa collected from a different location, by HPLC‐DAD [28] .…”

Dihydroisocoumarins and Phenylglycosides from Scorzonera longiana, Their Antimicrobial Activities and Molecular Docking Studies

“…Numerous phytochemical analyses and studies on the biological activity of Scorzonera species have been conducted with regard to the ethnobotanical value of the genus [3,10–12] . Phytochemical studies on Scorzonera species have shown the presence of flavonoids, dihydroisocoumarins, sesquiterpenes, triterpenes, stilbenes, quinic acid, chlorogenic acid, caffeic acid derivatives, and other bioactive compounds [3,7,8,9,11–37] . Biological evaluation of the isolated compounds and extracts/fractions of Scorzonera species was also reported [3,11,12,36–43] …”