275. Naturally occurring oxygen heterocyclics. Part XI. Veraguensin
About: This article is published in Journal of The Chemical Society (resumed).The article was published on 1962-01-01. It has received 24 citations till now.
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TL;DR: Although there is a great paucity of data, the variation in the arylpropanoids, alkaloids, flavanoids and terpene constituents is in general in agreement with the subdivision of the Lauraceae.
174 citations
TL;DR: A versatile route to the synthesis of 2,5-diaryl-3,4-dimethyltetrahydrofuran lignans, (-)-odoratisol C (1), (-)-futokadsurin A (2), (--veraguensin (3), (+)-fragransin A2 (4), (+-galbelgin (5), and (+)-talaumidin (6), is described.
49 citations
TL;DR: Acid-catalyzed cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes and have been used in the synthesis of the naturally occurring lignans (+/--cagayanin and (+/-)-galbulin.
Abstract: Acid-catalyzed cyclizations of E,E-dibenzylidenesuccinate esters have been developed as an efficient synthetic route to 1-aryl-1,2-dihydronaphthalenes. This reaction has been used in the synthesis of the naturally occurring lignans (+/-)-cagayanin and (+/-)-galbulin.
45 citations
TL;DR: These lignans inhibited nitric oxide production by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide and interferon-gamma.
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-γ.
44 citations
TL;DR: It was suggested that the analgesic effects obtained for EBCA could be due mainly to the presence of its major compound, α‐asarone (1), which showed activity in the abdominal constriction test and the anti‐inflammatory assay.
Abstract: The bioactivity-guided phytochemical investigation of the crude hydralcoholic extract of Nectandra megapotamica was carried out using the abdominal constriction test in mice, which led to the isolation of three active compounds: -asarone (1), galgravin (2) and veraguensin (3). The crude extract (EBCA, 300mgkg � 1 ) and isolated compounds 1, 2 ,a nd3, at different doses, were evaluated using the acetic acid-induced abdominal constriction test in mice, carrageenan-induced paw oedema in rats, and hot plate tests in rats. The EBCA showed a significant effect in the abdominal constriction and hot plate tests, but did not show activity in the rat paw oedema assay. All isolated compounds displayed activity in the abdominal constriction test, but only compound 1 was active in the hot plate test. Compounds 2 and 3 displayed activity in the anti-inflammatory assay. It was suggested that the analgesic effects obtained for EBCA could be due mainly to the presence of its major compound, -asarone (1).
37 citations
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...The spectral data of all isolated compounds were in agreement with those reported by other investigators: -asarone (1) (González et al 1996), galgravin (2) (Crossley & Djerassi 1962), and (þ)-veraguensin (3) (Crossley & Djerassi 1962)....
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