Sanctis A–C: Three Racemic Procyanidin Analogues from The Lichen Parmotrema sancti-angelii

Thuc Huy Duong, Xuan Phong Ha, Warinthorn Chavasiri, Mehdi A. Beniddir, Grégory Genta-Jouve, Joël Boustie, Marylène Chollet-Krugler, Solenn Ferron, Hung Huy Nguyen, Bohari Mohd. Yamin, Bui Linh Chi Huynh, Pierre Le Pogam, Kim Phi Phung Nguyen

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The phytochemical investigation of the lichen Parmotrema sancti-angelii afforded three racemic compounds, sanctis A–C, which feature an original dibenzo-2,8-dioxabicyclo[3.3.1]nonane scaffold. These compounds were structurally characterized by extensive NMR spectroscopy analyses, comparison between experimental and theoretical NMR spectroscopic data, and X-ray crystallography. These metabolites are similar to procyanidin A and display a methyl group instead of a pendant aromatic ring at C-9, a so far unprecedented structural feature. A biosynthetic route to sanctis A–C is proposed.

Original languageEnglish
Pages (from-to)2247-2253
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number19
DOIs
Publication statusPublished - 24 May 2018

Fingerprint

lichens
X ray crystallography
Phytochemicals
Metabolites
Scaffolds
Nuclear magnetic resonance spectroscopy
alternating current
Nuclear magnetic resonance
analogs
nonanes
nuclear magnetic resonance
metabolites
crystallography
routes
rings
spectroscopy
x rays
procyanidin
Lichens
2,8-dioxabicyclo(3.3.1)nonane

Keywords

  • Biosynthesis
  • Cytotoxicity
  • Natural products
  • Procyanidin analogues
  • Structure elucidation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Duong, T. H., Ha, X. P., Chavasiri, W., Beniddir, M. A., Genta-Jouve, G., Boustie, J., ... Nguyen, K. P. P. (2018). Sanctis A–C: Three Racemic Procyanidin Analogues from The Lichen Parmotrema sancti-angelii. European Journal of Organic Chemistry, 2018(19), 2247-2253. https://doi.org/10.1002/ejoc.201800202

Sanctis A–C : Three Racemic Procyanidin Analogues from The Lichen Parmotrema sancti-angelii. / Duong, Thuc Huy; Ha, Xuan Phong; Chavasiri, Warinthorn; Beniddir, Mehdi A.; Genta-Jouve, Grégory; Boustie, Joël; Chollet-Krugler, Marylène; Ferron, Solenn; Nguyen, Hung Huy; Mohd. Yamin, Bohari; Huynh, Bui Linh Chi; Le Pogam, Pierre; Nguyen, Kim Phi Phung.

In: European Journal of Organic Chemistry, Vol. 2018, No. 19, 24.05.2018, p. 2247-2253.

Research output: Contribution to journalArticle

Duong, TH, Ha, XP, Chavasiri, W, Beniddir, MA, Genta-Jouve, G, Boustie, J, Chollet-Krugler, M, Ferron, S, Nguyen, HH, Mohd. Yamin, B, Huynh, BLC, Le Pogam, P & Nguyen, KPP 2018, 'Sanctis A–C: Three Racemic Procyanidin Analogues from The Lichen Parmotrema sancti-angelii', European Journal of Organic Chemistry, vol. 2018, no. 19, pp. 2247-2253. https://doi.org/10.1002/ejoc.201800202
Duong, Thuc Huy ; Ha, Xuan Phong ; Chavasiri, Warinthorn ; Beniddir, Mehdi A. ; Genta-Jouve, Grégory ; Boustie, Joël ; Chollet-Krugler, Marylène ; Ferron, Solenn ; Nguyen, Hung Huy ; Mohd. Yamin, Bohari ; Huynh, Bui Linh Chi ; Le Pogam, Pierre ; Nguyen, Kim Phi Phung. / Sanctis A–C : Three Racemic Procyanidin Analogues from The Lichen Parmotrema sancti-angelii. In: European Journal of Organic Chemistry. 2018 ; Vol. 2018, No. 19. pp. 2247-2253.
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