PMID- 10552664
OWN - NLM
STAT- MEDLINE
DCOM- 20000912
LR  - 20190723
IS  - 0021-8561 (Print)
IS  - 0021-8561 (Linking)
VI  - 47
IP  - 8
DP  - 1999 Aug
TI  - NMR and molecular mechanics study of pyrethrins I and II.
PG  - 3402-10
AB  - Bioassay-directed fractionation of the organic extract of the Kenyan pyrethrum 
      flowers (Chrysanthemum cinerariaefolium Vissiani) resulted in the isolation of 
      two natural pyrethrin esters, pyrethrin I (PI) and pyrethrin II (PII) as the 
      major constituents. These esters elicited inhibition of the multiple drug 
      resistant (MDR) Mycobacterium tuberculosis. The high-field (1)H and (13)C nuclear 
      magnetic resonance (NMR) chemical shifts of PI and PII were unequivocally 
      assigned using modern two-dimensional (2D) proton-detected heteronuclear 
      multiple-quantum coherence (HMQC) and heteronuclear multiple-bond correlation 
      (HMBC) experiments. The conformations of both esters were deduced from (1)H-(1)H 
      vicinal coupling constants and confirmed by 2D nuclear Overhauser effect 
      spectroscopy (NOESY). Computer molecular modeling (MM) studies revealed that PI 
      and PII molecules adopt a "love-seat" conformation in chloroform (CDCl(3)) 
      solution.
FAU - Rugutt, J K
AU  - Rugutt JK
AD  - Department of Chemistry, Louisiana State University, Baton Rouge 70803, USA.
FAU - Henry, C W 3rd
AU  - Henry CW 3rd
FAU - Franzblau, S G
AU  - Franzblau SG
FAU - Warner, I M
AU  - Warner IM
LA  - eng
GR  - GM 39844/GM/NIGMS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - J Agric Food Chem
JT  - Journal of agricultural and food chemistry
JID - 0374755
RN  - 0 (Insecticides)
RN  - 0 (Plant Extracts)
RN  - 0 (Pyrethrins)
RN  - T018I9EQOL (pyrethrin I)
SB  - IM
MH  - Chrysanthemum cinerariifolium
MH  - Computer Simulation
MH  - Insecticides/*chemistry/isolation & purification
MH  - Magnetic Resonance Spectroscopy
MH  - Models, Molecular
MH  - Molecular Conformation
MH  - Plant Extracts/chemistry
MH  - Pyrethrins/*chemistry/isolation & purification
EDAT- 1999/12/20 09:00
MHDA- 2000/09/19 11:01
CRDT- 1999/12/20 09:00
PHST- 1999/12/20 09:00 [pubmed]
PHST- 2000/09/19 11:01 [medline]
PHST- 1999/12/20 09:00 [entrez]
AID - jf980660b [pii]
AID - 10.1021/jf980660b [doi]
PST - ppublish
SO  - J Agric Food Chem. 1999 Aug;47(8):3402-10. doi: 10.1021/jf980660b.