Acetogenin and prenylated flavonoids from Helminthostachys zeylanica with inhibitory activity on superoxide generation and elastase release by neutrophils.
One new acetogenin, 6-hydroxy-8-pentadecyloxocane-2,7-dione ( 1), and four new prenylated flavonoids, 4''a,5'',6'',7'',8'',8''a-hexahydro-5,3',4'-trihydroxy-5'',5'',8''a-trimethyl-4 H-chromeno[2'',3'':7,6]flavone ( 2), 4''a,5'',6'',7'',8'',8''a-hexahydro-5,3',4',-trihydroxy-5'',5'',8''a-trimethyl-4 H-chromeno[2'',3'':7,8]flavone ( 3), 2-(3,4-dihydroxyphenyl)-6-((2,2-dimethyl-6-methylenecyclohexyl)methyl)-5,7-dihydroxy-chroman-4-one ( 4), and 2-(3,4-dihydroxy-2-[(2,6,6-trimethylcyclohex-2-enyl)methyl]phenyl)-3,5,7-trihydroxy-4 H-chromen-4-one ( 5), together with six known compounds, were isolated and purified from the rhizomes of Helminthostachys zeylanica by column chromatography and high performance liquid chromatography (HPLC) via bioactivity-guided fractionation isolation. The structures of the new isolates were elucidated by spectroscopic methods. Compounds 1, 3, and 5 showed inhibitory activities on either superoxide anion generation or elastase release by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (FMLP/CB).
Huang
Yuan-Chao
YC
Graduate Institute of Pharmaceutical Chemistry, College of Pharmacy, China Medical University, Taichung, Taiwan.
Hwang
Tsong-Long
TL
Yang
Yu-Liang
YL
Wu
Shih-Hsiung
SH
Hsu
Mei-Hua
MH
Wang
Jih-Pyang
JP
Chen
Sheng-Chih
SC
Huang
Li-Jiau
LJ
Liaw
Chih-Chuang
CC
D054378:Acetogenins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D000293:Adolescent; D000328:Adult; D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D045744:Cell Line, Tumor; D029624:Ferns / Q000737:chemistry*; D005419:Flavonoids / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D006801:Humans; D009504:Neutrophils / Q000187:drug effects* / Q000201:enzymology; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity; D054876:Prenylation; D027343:Rhizome / Q000737:chemistry; D013481:Superoxides / Q000037:antagonists & inhibitors / Q000378:metabolism*; D055815:Young Adult
D054378:Acetogenins; D000893:Anti-Inflammatory Agents; D005419:Flavonoids; D010936:Plant Extracts; D013481:Superoxides; D010196:Pancreatic Elastase