First stereoselective synthesis of meso-secoisolariciresinol and comparison of its biological activity with (+) and (-)-secoisolariciresinol.
The first stereoselective synthesis of meso-secoisolariciresinol is reported. A comparison of the cytotoxic and immunosuppressive activity between meso-secoisolariciresinol and optically active secoisolariciresinols was similarly performed for the first time. Both enantiomers of secoisolariciresinol accelerated IgM production, although meso-secoisolariciresinol did not affect IgM production. Only meso-secoisolariciresinol showed cytotoxic activity.
Sugahara
Takuya
T
Faculty of Agriculture, Ehime University, Matsuyama, Ehime, Japan.
Yamauchi
Satoshi
S
Kondo
Ai
A
Ohno
Fumi
F
Tominaga
Siori
S
Nakashima
Yuki
Y
Kishida
Taro
T
Akiyama
Koichi
K
Maruyama
Masafumi
M
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002072:Butylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D007075:Immunoglobulin M / Q000096:biosynthesis; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D008807:Mice, Inbred BALB C; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D002072:Butylene Glycols; D007075:Immunoglobulin M; D007166:Immunosuppressive Agents; D017705:Lignans; C060283:secoisolariciresinol