C-NMR dereplication of Garcinia extracts: Predicted chemical shifts as reliable databases.

Antoine Bruguière, Séverine Derbré, Chloé Coste, Maxime Le Bot, Benjamin Siegler, Sow Tein Leong, Syazreen Nadia Sulaiman, Khalijah Awang, Pascal Richomme

Journal: Fitoterapia 2018;131():59-64

PMID: 30321650

Full Text on Elsevier Science View on PubMed

Abstract

Usually isolated from Garcinia (Clusiaceae) or Hypericum (Hypericaceae) species, some Polycyclic Polyprenylated AcylPhloroglucinols (PPAPs) have been recently reported as potential research tools for immunotherapy. Aiming at exploring the chemodiversity of PPAPs amongst Garcinia genus, a dereplication process suitable for such natural compounds has been developed. Although less sensitive than mass spectrometry, NMR spectroscopy is perfectly reproducible and allows stereoisomers distinction, justifying the development of C-NMR strategies. Dereplication requires the use of databases (DBs). To define if predicted DBs were accurate enough as dereplication tools, experimental and predicted δ of natural products usually isolated from Clusiaceae were compared. The ACD/Labs commercial software allowed to predict 73% of δ in a 1.25 ppm range around the experimental values. Consequently, with these parameters, the major PPAPs from a Garcinia bancana extract were successfully identified using a predicted DB.

Address: SONAS SFR QUASAV, University of Angers, France.; SONAS SFR QUASAV, University of Angers, France. Electronic address: [email protected].; SFR MATRIX, University of Angers, France.; Department of Chemistry, Faculty of sciences, University of Malaya, Malaysia.

DOI: 10.1016/j.fitote.2018.10.003

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MeSH Terms: Databases, Chemical, Garcinia, Magnetic Resonance Spectroscopy, Phloroglucinol, Phytochemicals, Plant Extracts