African Elephant Sesquiterpenes. II. Identification and Synthesis of New Derivatives of 2,3-Dihydrofarnesol

African Elephant Sesquiterpenes. II. Identification and Synthesis of New Derivatives of 2,3-Dihydrofarnesol

A search for potential semiochemicals revealed nerolidol (6), albicanol (7), and the new 2,3-dihydrofarnesol derivatives 8−10 in the temporal gland secretions of African elephants. A novel synthesis from (E,E)-farnesol (1) provided compounds 8−10 for GC−MS comparison to the natural products. This st...

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Veröffentlicht in:Journal of natural products (Washington, D.C.) D.C.), 2002-09, Vol.65 (9), p.1319-1322
Hauptverfasser: Goodwin, Thomas E, Brown, Felisia D, Counts, Richard W, Dowdy, Nichole C, Fraley, Patrick L, Hughes, Randall A, Liu, Daniel Z, Mashburn, Courtney D, Rankin, Josh D, Roberson, Russell S, Wooley, Katie D, Rasmussen, Elizabeth L, Riddle, Scott W, Riddle, Heidi S, Schulz, Stefan
Format: Artikel
Sprache:eng
Schlagworte:
Africa
Analytical, structural and metabolic biochemistry
Animals
Apocrine Glands - metabolism
Biological and medical sciences
Elephants - metabolism
Farnesol - analogs & derivatives
Farnesol - chemical synthesis
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Intermediate and energetic metabolism
Male
Metabolisms and neurohumoral controls
Molecular Structure
Naphthalenes - chemistry
Other biological molecules
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Spectroscopy, Fourier Transform Infrared
Stereoisomerism
Terpenes, steroids. Hormones
Vertebrates: anatomy and physiology, studies on body, several organs or systems
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Zusammenfassung:A search for potential semiochemicals revealed nerolidol (6), albicanol (7), and the new 2,3-dihydrofarnesol derivatives 8−10 in the temporal gland secretions of African elephants. A novel synthesis from (E,E)-farnesol (1) provided compounds 8−10 for GC−MS comparison to the natural products. This study confirms the farnesol family as frequently occurring secondary metabolites in African elephant temporal gland secretions.
ISSN:0163-3864
1520-6025
DOI:10.1021/np010647c