Evolvosides C–E, flavonol-4'-O-triglycosides from evolvulus alsinoides and their anti-stress activity [corrected].
Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1-3) along with six known compounds (4-9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4'-O-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside, whereas evolvosides D and E (2-3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1-3) represent rare triglycoside derivatives of flavonol at C-4'. The isolated compounds (1-6) were screened for acute stress-induced biochemical changes in male Sprague-Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects.
Division of Medicinal Chemistry, Central Drug Research Institute, Lucknow 226001, Uttar Pradesh, India. prasoonfau@gmail.com
Prasoon
P
Gupta
Upasana
U
Sharma
Praveen
P
Gupta
Kiran Babu
KB
Siripurapu
Rakesh
R
Maurya
D000818:Animals; D027722:Convolvulaceae / Q000737:chemistry*; D003345:Corticosterone / Q000097:blood; D003402:Creatine Kinase / Q000097:blood; D044948:Flavonols / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D006943:Hyperglycemia / Q000188:drug therapy; D044949:Kaempferols / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D008968:Molecular Conformation; D051381:Rats; D017207:Rats, Sprague-Dawley; D013312:Stress, Physiological / Q000187:drug effects; D014312:Trisaccharides / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use
D044948:Flavonols; D006027:Glycosides; D044949:Kaempferols; D014312:Trisaccharides; C582993:kaempferol 4'-O-glucopyranosyl-(1-2)-rhamnopyranosyl-(1-6)-glucopyranoside; C582995:kaempferol-5,7-dimethoxy-4'-O-glucopyranosyl-(1-2)-rhamnopyranosyl-(1-6)-glucopyranoside; C582994:kaempferol-7-methoxy-4'-O-glucopyranosyl-(1-2)-rhamnopyranosyl-(1-6)-glucopyranoside; D003402:Creatine Kinase; D003345:Corticosterone