Miniaturization of the structure elucidation of novel natural products - two trace antibacterial acylated caprylic alcohol glycosides from Arctostaphylos pumila

• Published in: Planta medica Vol. 71; no. 2; pp. 176 - 180
• Main Authors: Hu, J.F, Yoo, H.D, Williams, C.T, Garo, E, Cremin, P.A, Zeng, L, Vervoort, H.C, Lee, C.M, Hart, S.M, Goering, M.G
• Format: Journal Article
• Language: English
• Published: Germany 01.02.2005
• Subjects: 2,6-diacetyl-3,4-diisobutyl-1-O-octylglucopyranoside; 2,6-diacetyl-3,4-dimethylbutyl-1-O-octylglucopyranoside; Anti-Bacterial Agents - administration & dosage; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Anti-Bacterial Agents - therapeutic use; antibacterial properties; Arctostaphylos; Arctostaphylos pumila; chemical structure; Ericaceae; glycosides; Glycosides - administration & dosage; Glycosides - chemistry; Glycosides - pharmacology; Glycosides - therapeutic use; human health; Humans; Methicillin Resistance; Microbial Sensitivity Tests; octanoic acid; Phytotherapy; Plant Extracts - administration & dosage; Plant Extracts - chemistry; Plant Extracts - pharmacology; Plant Extracts - therapeutic use; spectral analysis; Staphylococcus aureus; Staphylococcus aureus - drug effects; stereochemistry
• ISSN: 0032-0943; 1439-0221
• DOI: 10.1055/s-2005-837787

High-throughput isolation, purification and analysis methods applied to natural products libraries from plants gave rise to the discovery of two novel acylated caprylic alcohol glycosides (1, 2) produced by Arctostaphylos pumila. The NMR spectra were acquired using the CapNMR probe and performed on mass-limited samples, which enabled us to elucidate the structures of 2,6-diacetyl-3,4-diisobutyl-1- O-octylglucopyranoside (1, 200 microg) and 2,6-diacetyl-3,4-dimethylbutyl-1- O-octylglucopyranosid (2, 70 microg). Compounds 1 and 2 exhibited antibacterial activity against Gram-positive methicillin-resistant Staphylococcus aureus with an MIC of 128 microg/mL and 64 microg/mL, respectively.