Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata

Nanzad Tsevegsuren, Ruangelie Edrada-Ebel, Wenhan Lin, Rainer Ebel, Claudia Torre, Sofia Ortlepp, Victor Wray, Peter Proksch

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

Chromatographic separation of a crude extract obtained from the aerial parts of the Mongolian medicinal plant Scorzonera divaricata yielded the two new quinic acid derivatives feruloylpodospermic acids A and B. Both compounds feature a feruloyl group and two dihydrocaffeoyl substituents. For feruloylpodospermic acid A, the dihydrocaffeic acid substituents were found esterified at positions 1 and 5 of the quinic acid moiety, while the feruloyl group was attached at position 3. For feruloylpodospermic acid B, the substituents were linked at positions 1, 3, and 4. The aerial parts of S. pseudodivaricata that are likewise used in Mongolian traditional medicine yielded two further new natural products, for which the names scorzoneric acid and scorzonerin are proposed. Scorzoneric acid is an unusual phenolic compound featuring a central tetrasubstituted phenyl ring to which a glucose unit is bound, which in turn is substituted by an esterified acyl side chain. Further substituents of the central phenyl ring system include a butan-2-one group, which is linked to a second para-substituted phenyl ring system. Scorzonerin is a matricarin-based sesquiterpene lactone that carries an esterified dihydrocoumaric acid moiety, which in turn is glycosidically bound to glucose. The structures of all new compounds were unambiguously established from NMR (1H, 13C, COSY, HMBC) spectroscopic and mass spectrometric data. The new quinic acid derivatives feruloylpodospermic acids A and B exhibited strong antioxidative activity when analyzed in the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay.

LanguageEnglish
Pages962-967
Number of pages6
JournalJournal of Natural Products
Volume70
Issue number6
Early online date2 Jun 2007
DOIs
Publication statusPublished - Jun 2007

Fingerprint

Scorzonera
Quinic Acid
Medicinal Plants
Biological Products
Mongolian Traditional Medicine
Acids
Antennas
Derivatives
Glucose
Sesquiterpenes
Lactones
Complex Mixtures
Medicine
Names
Assays
Nuclear magnetic resonance
feruloylpodospermic acid A
feruloylpodospermic acid B

Keywords

  • animals
  • antineoplastic agents
  • antioxidants
  • biological products
  • biphenyl compounds
  • drug screening assays, antitumor
  • mice
  • molecular structure
  • mongolia
  • picrates
  • plants, Medicinal
  • quinic acid
  • scorzonera

Cite this

Tsevegsuren, Nanzad ; Edrada-Ebel, Ruangelie ; Lin, Wenhan ; Ebel, Rainer ; Torre, Claudia ; Ortlepp, Sofia ; Wray, Victor ; Proksch, Peter. / Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata. In: Journal of Natural Products. 2007 ; Vol. 70, No. 6. pp. 962-967.
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abstract = "Chromatographic separation of a crude extract obtained from the aerial parts of the Mongolian medicinal plant Scorzonera divaricata yielded the two new quinic acid derivatives feruloylpodospermic acids A and B. Both compounds feature a feruloyl group and two dihydrocaffeoyl substituents. For feruloylpodospermic acid A, the dihydrocaffeic acid substituents were found esterified at positions 1 and 5 of the quinic acid moiety, while the feruloyl group was attached at position 3. For feruloylpodospermic acid B, the substituents were linked at positions 1, 3, and 4. The aerial parts of S. pseudodivaricata that are likewise used in Mongolian traditional medicine yielded two further new natural products, for which the names scorzoneric acid and scorzonerin are proposed. Scorzoneric acid is an unusual phenolic compound featuring a central tetrasubstituted phenyl ring to which a glucose unit is bound, which in turn is substituted by an esterified acyl side chain. Further substituents of the central phenyl ring system include a butan-2-one group, which is linked to a second para-substituted phenyl ring system. Scorzonerin is a matricarin-based sesquiterpene lactone that carries an esterified dihydrocoumaric acid moiety, which in turn is glycosidically bound to glucose. The structures of all new compounds were unambiguously established from NMR (1H, 13C, COSY, HMBC) spectroscopic and mass spectrometric data. The new quinic acid derivatives feruloylpodospermic acids A and B exhibited strong antioxidative activity when analyzed in the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay.",
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Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata. / Tsevegsuren, Nanzad; Edrada-Ebel, Ruangelie; Lin, Wenhan; Ebel, Rainer; Torre, Claudia; Ortlepp, Sofia; Wray, Victor; Proksch, Peter.

In: Journal of Natural Products, Vol. 70, No. 6, 06.2007, p. 962-967.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Biologically active natural products from Mongolian medicinal plants Scorzonera divaricata and Scorzonera pseudodivaricata

AU - Tsevegsuren, Nanzad

AU - Edrada-Ebel, Ruangelie

AU - Lin, Wenhan

AU - Ebel, Rainer

AU - Torre, Claudia

AU - Ortlepp, Sofia

AU - Wray, Victor

AU - Proksch, Peter

PY - 2007/6

Y1 - 2007/6

N2 - Chromatographic separation of a crude extract obtained from the aerial parts of the Mongolian medicinal plant Scorzonera divaricata yielded the two new quinic acid derivatives feruloylpodospermic acids A and B. Both compounds feature a feruloyl group and two dihydrocaffeoyl substituents. For feruloylpodospermic acid A, the dihydrocaffeic acid substituents were found esterified at positions 1 and 5 of the quinic acid moiety, while the feruloyl group was attached at position 3. For feruloylpodospermic acid B, the substituents were linked at positions 1, 3, and 4. The aerial parts of S. pseudodivaricata that are likewise used in Mongolian traditional medicine yielded two further new natural products, for which the names scorzoneric acid and scorzonerin are proposed. Scorzoneric acid is an unusual phenolic compound featuring a central tetrasubstituted phenyl ring to which a glucose unit is bound, which in turn is substituted by an esterified acyl side chain. Further substituents of the central phenyl ring system include a butan-2-one group, which is linked to a second para-substituted phenyl ring system. Scorzonerin is a matricarin-based sesquiterpene lactone that carries an esterified dihydrocoumaric acid moiety, which in turn is glycosidically bound to glucose. The structures of all new compounds were unambiguously established from NMR (1H, 13C, COSY, HMBC) spectroscopic and mass spectrometric data. The new quinic acid derivatives feruloylpodospermic acids A and B exhibited strong antioxidative activity when analyzed in the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay.

AB - Chromatographic separation of a crude extract obtained from the aerial parts of the Mongolian medicinal plant Scorzonera divaricata yielded the two new quinic acid derivatives feruloylpodospermic acids A and B. Both compounds feature a feruloyl group and two dihydrocaffeoyl substituents. For feruloylpodospermic acid A, the dihydrocaffeic acid substituents were found esterified at positions 1 and 5 of the quinic acid moiety, while the feruloyl group was attached at position 3. For feruloylpodospermic acid B, the substituents were linked at positions 1, 3, and 4. The aerial parts of S. pseudodivaricata that are likewise used in Mongolian traditional medicine yielded two further new natural products, for which the names scorzoneric acid and scorzonerin are proposed. Scorzoneric acid is an unusual phenolic compound featuring a central tetrasubstituted phenyl ring to which a glucose unit is bound, which in turn is substituted by an esterified acyl side chain. Further substituents of the central phenyl ring system include a butan-2-one group, which is linked to a second para-substituted phenyl ring system. Scorzonerin is a matricarin-based sesquiterpene lactone that carries an esterified dihydrocoumaric acid moiety, which in turn is glycosidically bound to glucose. The structures of all new compounds were unambiguously established from NMR (1H, 13C, COSY, HMBC) spectroscopic and mass spectrometric data. The new quinic acid derivatives feruloylpodospermic acids A and B exhibited strong antioxidative activity when analyzed in the DPPH (2,2-diphenyl-1-picrylhydrazyl) assay.

KW - animals

KW - antineoplastic agents

KW - antioxidants

KW - biological products

KW - biphenyl compounds

KW - drug screening assays, antitumor

KW - mice

KW - molecular structure

KW - mongolia

KW - picrates

KW - plants, Medicinal

KW - quinic acid

KW - scorzonera

U2 - 10.1021/np070013r

DO - 10.1021/np070013r

M3 - Article

VL - 70

SP - 962

EP - 967

JO - Journal of Natural Products

T2 - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 6

ER -