Lignans ofChamaecyparis obtusa

Abstract

Heartwood of Charnaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan, hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans -xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and matairesinol (11) -were isolated from young shoots of Chamaecyparis obtusa cv. Breviramea. Eight lignans (1, 2, 4, 5, 7, 9, 10, and 11) were isolated from this plant for the first time. Chiral high-performance liquid chromatographic analysis showed that 8, 9, 10, and 11, were found to be levorotatory and optically pure (>99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of 8 are discussed.

Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii

“…As part of serial investigations on the Gymnospermae plants and in order to seek more novel bioactive compounds, we carried out an extensive chemical study on S. gaussenii [4][5][6][7]. In this paper, we report the isolation and structure elucidation of two new cinnamyl isovalerate derivatives (1-2) together with eighteen other known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) from the branches and leaves of S. gaussenii, in addition to a screening of their cytotoxicities.…”

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Abstract: Chemical investigation of the 90% acetone extract of the branches and leaves of Sabina gaussenii led to the isolation of two new cinnamyl isovalerate derivatives (1-2) and eighteen known compounds (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). Their structures were determined mainly by means of MS, 1D-and 2D-NMR data, and this is the first time these compounds have been reported from this plant.

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Metabolismo secundário e ligninas de espécies de Piper

“…Esta lignana, isolada anteriormente de espécies de Myristicaceae (Vidigal, 1993), da familia Cupressaceae cuja espécie é Chamaecyparis obtusa (Takaku et al, 2001), também foi encontrada na família Asteraceae e espécie Artemisia absinthium (Greger e Hofer,1980 9 ax 9'ax 9 eq 9'eq O2CH2 H-Ar 8 e 8' 9 e 9' 7 e 7' 2 e 2' 5 e 5' 6 e 6' A lignana 3, identificado como sendo hinokinina, foi isolado das folhas de P.…”

“…Esta lignana foi isolada anteriormente de espécies de Myristicaceae (Vidigal, 1993) e Chamaecyparis obtusa (Takaku et al, 2001). A lignana 4, identificado como sendo kusunokinina foi isolado anteriormente de espécies de Myristicaceae (Vidigal, 1993), Piper chaba (Connolly et al, 1995).…”

“…Esta lignana, isolada anteriormente da família Cupressaceae, espécie Chamaecyparis obtusa (Takaku et al, 2001) e da espécie Haplophyllum myrtifolium uma Rutaceae (Evcim et al, 1986 …”