Isolation of saponins with the inhibitory effect on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha production from Pleurospermum kamtschaticum.
As an attempt to search for bioactive natural products exerting antiinflammatory activity, we have isolated two saponins were isolated from the aerial portion of Pleurospermum kamtschaticum (Umbelliferae) by nitrite assay activity-directed chromatographic fractionation. They were identified as saikogenin F 3-O-{beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-fucopyranoside} (buddlejasaponin IV, 1) and 3beta,16beta,23,28-tetrahydroxy-11alpha-methoxyolean-12-ene 3-O-{beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->3)]-beta-D-fucopyranoside} (buddlejasaponin IVa, 2). Compound 1 significantly inhibited nitric oxide (NO) production, and it also significantly decreased prostaglandin E2 (PGE2) and tumor necrosis factor-alpha (TNF-alpha) release in the lipopolysaccharide (LPS)-activated macrophage Raw 264.7 cells whereas compound 2 was much less active. Saikogenin A (3) and -H (4) were obtained by hydrolyzing 1 and 2. Although these sapogenin showed strong NO inhibition, these effects were caused by the cytotoxic effect on Raw 264.7 cells. These results supported the notion that buddlejasaponin IV is a major inhibitors of NO, PGE2 and TNF-alpha production in P. kamtschaticum.
Jung
Hyun-Ju
HJ
Division of Applied Plant Sciences, Sangji University, Wonju, Korea.
Kim
Sei-Gun
SG
Nam
Jung-Hwan
JH
Park
Kwang-Kyun
KK
Chung
Won-Yun
WY
Kim
Won-Bae
WB
Lee
Kyung-Tae
KT
Won
Jong-Heon
JH
Choi
Jong-Won
JW
Park
Hee-Juhn
HJ
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000302:isolation & purification* / Q000494:pharmacology*; D019661:Apiaceae / Q000737:chemistry*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D015232:Dinoprostone / Q000037:antagonists & inhibitors*; D006801:Humans; D008070:Lipopolysaccharides / Q000037:antagonists & inhibitors / Q000633:toxicity; D008264:Macrophages / Q000187:drug effects / Q000378:metabolism; D009569:Nitric Oxide / Q000037:antagonists & inhibitors*; D010936:Plant Extracts / Q000494:pharmacology; D011448:Prostaglandin Antagonists; D012502:Sapogenins / Q000302:isolation & purification / Q000494:pharmacology; D012503:Saponins / Q000302:isolation & purification* / Q000494:pharmacology*; D013778:Tetrazolium Salts; D013844:Thiazoles; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000096:biosynthesis*
D000894:Anti-Inflammatory Agents, Non-Steroidal; D008070:Lipopolysaccharides; D010936:Plant Extracts; D011448:Prostaglandin Antagonists; D012502:Sapogenins; D012503:Saponins; D013778:Tetrazolium Salts; D013844:Thiazoles; D014409:Tumor Necrosis Factor-alpha; C104869:buddlejasaponin; C439329:saikogenin F; D009569:Nitric Oxide; C022616:thiazolyl blue; D015232:Dinoprostone