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DOI: 10.1055/s-2005-837787
© Georg Thieme Verlag KG Stuttgart · New York
Miniaturization of the Structure Elucidation of Novel Natural Products - Two Trace Antibacterial Acylated Caprylic Alcohol Glycosides from Arctostaphylos pumila
Publication History
Received: May 17, 2004
Accepted: August 29, 2004
Publication Date:
24 February 2005 (online)
Abstract
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 μg) and 2,6-diacetyl-3,4-dimethylbutyl-1-O-octylglucopyranosid (2, 70 μg). Compounds 1 and 2 exhibited antibacterial activity against Gram-positive methicillin-resistant Staphylococcus aureus with an MIC of 128 μg/mL and 64 μg/mL, respectively.
Key words
High-throughput natural products chemistry - CapNMRTM probe - Arctostaphylos pumila - Ericaceae - acylated caprylic alcohol glycosides - antibacterial.
References
- 1 Eldridge G R, Vervoort H C, Lee C M, Cremin P A, Williams C T, Hart S M, Goering M G, O’Neil-Johnson M, Zeng L. High-throughput method for the production and analysis of large natural product libraries for drug discovery. Anal Chem. 2002; 74 3963-71
- 2 Cremin P A, Zeng L. High-throughput analysis of natural product compound libraries by parallel LC-MS evaporative light scattering detection. Anal Chem. 2002; 74 5492-500
- 3 Hu J F, Garo E, Yoo H D, Cremin P A, Zeng L, Goering M G, O’Neil-Johnson M, Eldridge G R. Application of capillary scale NMR for the structure determination of Phytochemicals. Phytochem. Anal. in press
- 4 Wells P V. In: The Jepson Manual: Higher Plants of California. Hickman JC editor University of California Press Berkeley; 1993: pp 544-59
- 5 Geiger H, Schucker U, Waldrum H, Vandervelde G, Mabry T J. Quercetine-3-beta-D-(6-O-galloyl-galactoside), a constituent of Arctostaphylos uva-ursi (L) Spreng (Ericaceae). Z Naturforsch C. 1975; 30 296
- 6 Slaveska-Raicki R, Rafajlovska V, Rizova V, Spirevska I. HPTLC determination of gallic acid and tannin in the extracts of bearberry leaves. J Planar Chrom. 2003; 16 396-401
- 7 Shiota S, Shimizu M, Sugiyama J, Morita Y, Mizushima T, Tsuchiya T. Mechanisms of action of corilagin and tellimagrandin I that remarkably potentiate the activity of beta-lactams against methicillin-resistant Staphylococcus aureus . Microbiology and Immunology. 2004; 48 67-73
- 8 Kim Y C, Kingston D GI. A new caprylic alcohol glycoside from Circaea lutetiana ssp. canadensis. J Nat Prod. 1996; 59 1096-8
- 9 Yoshikawa M, Shimada H, Shimoda H, Matsuda H, Yamahara J, Murakami N. Rhodiocyanoside-A and rhodiocyanoside-B, new antiallergic cyanoglycosides from Chinese natural medicine Si-Li-Hong-Jing-Tian, the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey. Chem Pharm Bull. 1995; 43 1245-7
- 10 Kurahashi T, Mizutani T, Yoshida J. Effect of intramolecular hydrogen-bonding network on the relative reactivities of carbohydrate OH groups. J Chem Soc Perkin Trans 1 1999: 465-73
- 11 Kurahashi T, Mizutani T, Yoshida J. Functionalized DMAP catalysts for regioselective acetylation of carbohydrates. Tetrahedron. 2002; 58 8669-77
- 12 DiModugno E, Erbetti I, Ferrari L, Galassi G, Hammond S M, Xerri L. In-vitro activity of the Tribactam GV 104 326 against Gram-positive, Gram-negative, and anaerobic bacteria. Antimicrobial Agents and Chemotherapy. 1994; 38 2362-8
- 13 Misiek M, Pursiano T A, Leitner F, Price K E. Micobiological properties of a new cephalosporin, BL-S 339 : 7-(phenylacetyimidoyl-aminoacetamido)-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)ceph-3-em-4-carboxylic acid. Antimicrobial Agents and Chemotherapy. 1973; 3 40-8
Dr. Jin-Feng Hu
Lead Discovery & Rapid Structure Elucidation Group
Sequoia Sciences, Inc.
11199 Sorrento Valley Road, Suite H
San Diego
CA 92121
USA
Fax: +1-858-623-0805
Email: jhu@sequoiasciences.com