Carapanosins A-C from Seeds of Andiroba (Carapa guianensis, Meliaceae) and Their Effects on LPS-Activated NO Production.
Two new phragmalin-type limonoids, Carapanosins A and B (1and2), and a new gedunin-type limonoid, Carapansin C (3), together with five known limonoids (4-8) were isolated from the oil ofCarapa guianensisAUBLET(Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and HRFABMS. Compounds1-8were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that Compounds3,6, and8may be valuable as potential inhibitors of macrophage activation.
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. rikiaifuni815@yahoo.co.jp.
Keiichiro
K
Higuchi
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. teppei-727@ezweb.ne.jp.
Teppei
T
Miyake
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. syokentosmar0316@gmail.com.
Shoko
S
Ohmori
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tora-love.19920906@ezweb.ne.jp.
Yoshimi
Y
Tani
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. minoura@gly.oups.ac.jp.
Katsuhiko
K
Minoura
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. t.kikuchi@gly.oups.ac.jp.
Takashi
T
Kikuchi
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. yamada@gly.oups.ac.jp.
Takeshi
T
Yamada
Laboratory of Medicinal Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. tanakar@gly.oups.ac.jp.
Reiko
R
Tanaka
D000818:Animals; D002460:Cell Line; D036701:Limonins / Q000737:chemistry* / Q000494:pharmacology*; D008070:Lipopolysaccharides / Q000276:immunology; D008262:Macrophage Activation / Q000187:drug effects / Q000276:immunology; D008264:Macrophages / Q000187:drug effects* / Q000276:immunology / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D029582:Meliaceae / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis / Q000378:metabolism*; D010938:Plant Oils / Q000737:chemistry / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry*
D036701:Limonins; D008070:Lipopolysaccharides; D010938:Plant Oils; D009569:Nitric Oxide
Carapa guianensis; Carapanosins A–C; Meliaceae; limonoid; seed oil