African elephant sesquiterpenes. II. Identification and synthesis of new derivatives of 2,3-dihydrofarnesol

Journal of Natural Products

Volumn 65, Issue 9, 2002, Pages 1319-1322

  Goodwin, Thomas E ^a   Brown, Felisia D ^a   Counts, Richard W ^a   Dowdy, Nichole C ^a   Fraley, Patrick L ^a   Hughes, Randall A ^a   Liu, Daniel Z ^a   Mashburn, Courtney D ^a   Rankin, Josh D ^a   Roberson, Russell S ^a   Wooley, Katie D ^a   Rasmussen, Elizabeth L ^b   Riddle, Scott W ^c   Riddle, Heidi S ^c   Schulz, Stefan ^d  

^a HENDRIX COLLEGE   (United States)

^b OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^c Riddle's Elephant Wildl Sanctuary   (United States)

^d TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDROFARNESOL DERIVATIVE; 3,7,11 TRIMETHYL 1,7,11 DODECANETRIOL; 3,7,11 TRIMETHYL 10 DODECEN 1,7 DIOL; 3,7,11 TRIMETHYL 6 DODECEN 1,11 DIOL; ALBICANOL; FARNESOL; NEROLIDOL; SESQUITERPENE; UNCLASSIFIED DRUG;

ANIMAL ANATOMY; ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; ELEPHANT; EXTRACTION; FEMALE; GAS CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; METABOLITE; NONHUMAN; SECRETION; SYNTHESIS; TEMPORAL GLAND;

AFRICA; ANIMALS; APOCRINE GLANDS; ELEPHANTS; FARNESOL; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MALE; MOLECULAR STRUCTURE; NAPHTHALENES; SESQUITERPENES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

ANIMALIA; ELEPHANT; ELEPHANTIDAE; LOXODONTA;

EID: 0036741271     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np010647c     Document Type: Article

References (35)

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13. SPME has also been used to extract the preovulatory pheromone from the urine of female Asian elephants: (a) Rasmussen, L. E. L.; Lee, T. D.; Zhang, A.; Roelofs, W. L.; Daves, G. D., Jr. Chem. Senses 1997, 22, 417-437. (b) Rasmussen, L. E. L. Chem. Senses 2001, 26, 611-624.
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25. 13C NMR spectrum of triol 10, absorbances are seen at 29.12, 29.23, 29.36, 29.46, and 29.54 ppm. The DEPT spectra reveal that these peaks represent not only C-12 and C-15 but also C-3. The large number of peaks is due not only to the presence of two diastereomers but also to the fact that C-12 and C-15 in triol 10 are diastereotopic. These carbons are diastereotopic also in compounds 3 and 9, yet spectral differences were not discernible. Observable resonances of the minor diastereomer of triol 10 (not listed in Table 1) are δ 37.8 (C-4), 18.4 (C-5), 42.0 and 41.9 (C-6 and C-8), 21.0 (C-9), and 27.0 (C-14). Other peaks for the minor diastereomer could not be determined due to weak and/or overlapping absorbances.
26. 13C NMR spectrum of triol 10, absorbances are seen at 29.12, 29.23, 29.36, 29.46, and 29.54 ppm. The DEPT spectra reveal that these peaks represent not only C-12 and C-15 but also C-3. The large number of peaks is due not only to the presence of two diastereomers but also to the fact that C-12 and C-15 in triol 10 are diastereotopic. These carbons are diastereotopic also in compounds 3 and 9, yet spectral differences were not discernible. Observable resonances of the minor diastereomer of triol 10 (not listed in Table 1) are δ 37.8 (C-4), 18.4 (C-5), 42.0 and 41.9 (C-6 and C-8), 21.0 (C-9), and 27.0 (C-14). Other peaks for the minor diastereomer could not be determined due to weak and/or overlapping absorbances.
27. 13C NMR spectrum of triol 10, absorbances are seen at 29.12, 29.23, 29.36, 29.46, and 29.54 ppm. The DEPT spectra reveal that these peaks represent not only C-12 and C-15 but also C-3. The large number of peaks is due not only to the presence of two diastereomers but also to the fact that C-12 and C-15 in triol 10 are diastereotopic. These carbons are diastereotopic also in compounds 3 and 9, yet spectral differences were not discernible. Observable resonances of the minor diastereomer of triol 10 (not listed in Table 1) are δ 37.8 (C-4), 18.4 (C-5), 42.0 and 41.9 (C-6 and C-8), 21.0 (C-9), and 27.0 (C-14). Other peaks for the minor diastereomer could not be determined due to weak and/or overlapping absorbances.
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34. Compounds 2-5 and 8-11 were submitted to the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (Southern Research Institute) to assay for antimycobacterial activity. Compounds 2, 3, 5, and 11 showed very low percent inhibitions at the highest test concentrations. Bioassay results for the remaining compounds will be reported in due course. Testing of these compounds was prompted by the observation that farnesol (1) is active against tuberculosis (Mycobacterium tuberculosis): Rajab, M. S.; Cantrell, C. L.; Franzblau, S. G.; Fischer, N. H. Planta Med. 1998, 64, 2-4.
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