PMID- 20000781
OWN - NLM
STAT- MEDLINE
DCOM- 20100217
LR  - 20101118
IS  - 1520-6025 (Electronic)
IS  - 0163-3864 (Linking)
VI  - 73
IP  - 1
DP  - 2010 Jan
TI  - Iridoids from Fraxinus excelsior with adipocyte differentiation-inhibitory and 
      PPARalpha activation activity.
PG  - 2-6
LID - 10.1021/np9003118 [doi]
AB  - Two new secoiridoid glucosides, excelsides A (1) and B (2), were isolated from 
      the seeds of Fraxinus excelsior. Their structures were elucidated as 
      (2S,4S,3E)-methyl 
      3-ethylidene-4-(2-methoxy-2-oxoethyl)-2-[(6-O-beta-D-glucopyranosyl-beta-d-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate 
      and (2S,4S,3E)-methyl 
      3-ethylidene-4-2-[2-(4-hydroxyphenyl)ethyl]oxy-2-oxoethyl-2-[(6-O-beta-d-glucopyranosyl-beta-d-glucopyranosyl)oxy]-3,4-dihydro-2H-pyran-5-carboxylate, 
      respectively, on the basis of NMR and MS data. Eight known compounds were 
      identified as nuzhenide (3), GI3 (4), GI5 (5), ligstroside (6), oleoside 
      11-methyl ester (7), oleoside dimethyl ester (8), 1'''-O-beta-D-glucosylformoside 
      (9), and salidroside (10). Compounds 1-9 inhibited adipocyte differentiation in 
      3T3-L1 cells. Dilutions of the aqueous extract of F. excelsior (1:10,000) as well 
      as compounds 2, 3, 4, 5, and 8 activated the peroxisome proliferator-mediated 
      receptor-alpha (PPARalpha) reporter cell system in the range of 10(-4) M, 
      compared to 10(-7)-10(-8) M for the synthetic PPARalpha activator, WY14,643. Both 
      biological activity profiles support the hypothesis that inhibition of adipocyte 
      differentiation and PPARalpha-mediated mechanisms might be relevant pathways for 
      the antidiabetic activity of F. excelsior extract.
FAU - Bai, Naisheng
AU  - Bai N
AD  - Naturex, Inc., 375 Huyler Street, South Hackensack, New Jersey 07606, USA.
FAU - He, Kan
AU  - He K
FAU - Ibarra, Alvin
AU  - Ibarra A
FAU - Bily, Antoine
AU  - Bily A
FAU - Roller, Marc
AU  - Roller M
FAU - Chen, Xiaozhuo
AU  - Chen X
FAU - Ruhl, Ralph
AU  - Ruhl R
LA  - eng
PT  - Journal Article
PL  - United States
TA  - J Nat Prod
JT  - Journal of natural products
JID - 7906882
RN  - 0 (Iridoid Glucosides)
RN  - 0 (Iridoid Glycosides)
RN  - 0 (Iridoids)
RN  - 0 (PPAR alpha)
RN  - 0 (excelside A)
RN  - 0 (excelside B)
SB  - IM
MH  - Adipocytes/drug effects
MH  - Animals
MH  - Fraxinus/*chemistry
MH  - Iridoid Glucosides
MH  - Iridoid Glycosides
MH  - Iridoids/chemistry/*isolation & purification/*pharmacology
MH  - Mice
MH  - Molecular Structure
MH  - PPAR alpha/*drug effects
MH  - Plants, Medicinal/*chemistry
MH  - Seeds/chemistry
MH  - Stereoisomerism
EDAT- 2009/12/17 06:00
MHDA- 2010/02/18 06:00
CRDT- 2009/12/17 06:00
PHST- 2009/12/17 06:00 [entrez]
PHST- 2009/12/17 06:00 [pubmed]
PHST- 2010/02/18 06:00 [medline]
AID - 10.1021/np9003118 [doi]
PST - ppublish
SO  - J Nat Prod. 2010 Jan;73(1):2-6. doi: 10.1021/np9003118.