Neolignans from Piper futokadsura and Their Inhibition of Nitric Oxide Production

Abstract

From a MeOH extract of the aerial part of Piper futokadsura, the tetrahydrofuran lignans, futokadsurin A [(7S,8S,7'S,8'R)-3,4,3'-trimethoxy-4'-hydroxy-7,7'-epoxylignan], futokadsurin B [(7R,8R,7'R,8'S)-3,4-dimethoxy-3',4'-methylenedioxy-7,7'-epoxylignan], and futokadsurin C [(7R,8R,7'S,8'S)-3,4-methylenedioxy-3',4'-dimethoxy-7,7'-epoxylignan] were isolated, together with nine known neolignans. In addition, L-tryptophan, pellitorine, phytol, elemicin, and 1,2,4-trimethoxyphenyl-5-aldehyde were isolated. The structures of the new compounds were elucidated using spectroscopic methods. These lignans inhibited nitric oxide production by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide and interferon-gamma.

Total synthesis of (−)-talaumidin and (−)-galbelgin

“…(2 )-Talaumidin (1) and (2 )-galbelgin (2) are naturally occurring lignans isolated from Aristolochia arcuata [1] and Piper futokadsura [2]. They belong to 2,5-diaryl-3,4-dimethyl-tetrahydrofuran lignans, an important subclass of lignans, which, recently, have stimulated substantial synthetic efforts due to their structural diversity and biological activity [3].…”

Manipulating JNK Signaling with (−)-Zuonin A

“…(−)-zuonin A ( 1 ) is a 2,5-diaryl-3,4-dimethyltetrahydrofuranoid lignan which has been isolated from Aristolochia chilensis (27) , Saururus cernuus (28) , Piper schmidtii (29) , Chamaecyparis obtusa var. formosana (30), and Piper futokadsura (31). Notably, two recent reports have implicated other lignan derivatives as having biological effects resulting from their activity towards MAP kinases.…”

Total Synthesis and Stereochemical Confirmation of 2,5-Diaryl-3,4-dimethyltetrahydrofuran Lignans: (+)-Fragransin A2, (+)-Galbelgin, (+)-Talaumidin, (-)-Saucernetin and (-)-Verrucosin

“…Intermediate 6 is readily available in enantiomerically pure form as recently reported in the total synthesis of manassantin A, B and B 1 (Scheme 1). 14 Treatment with 4benzyloxy-3-methoxyphenylmagnesium bromide in the presence of CeCl 3 as an additive 15 gave an epimeric mixture of alcohols, which could be separated into major (8) and minor ( 9) compounds as MOM ethers, after removal of the TBS and allyl groups. Oxidation of the mixture of alcohols 7a and 7b under Dess-Martin conditions to the ketone, followed by reduction with NaBH 4 in the presence of CeCl 3 16 gave the R-alcohol 7b as the major product (90:10, Scheme 2).…”