Integrifolin, a guaianolide from Andryala integrifolia

Massanet, Guillermo M.; Collado, Isidro González; Macías, Francisco A.; Luis, F. Rodriguez; Vergara, Clarice Maria Araújo Chagas

doi:10.1016/s0031-9422(00)85061-x

Cited by 19 publications

(7 citation statements)

References 8 publications

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“…Finally, construction of the α‐methylene lactone by Eschenmoser's methylenation and deprotection of the TBS group with TBAF completed the first total synthesis of (±)‐integrifolin 1 . The 1 H NMR spectra of this synthetic compound matched nicely with the reported data of this natural product in CDCl 3 and CD 3 OD …”

Section: Figuresupporting

confidence: 82%

Total Synthesis of (±)‐Integrifolin

Shimomaki

Kusama

Iwasawa

2016

Chemistry A European J

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The total synthesis of (±)-integrifolin has been achieved for the first time through the stereoselective preparation of the bicyclo[5.3.0]decane skeleton based on the tungsten-catalyzed cyclization of acyclic trienynes under photoirradiation conditions. Further key transformations of the cyclized product are the Tamao oxidation through cyclic silyl ether, the introduction of two oxygen functionalities by the oxidation of the diene and the construction of three exo-methylene moieties.

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Section: Figuresupporting

confidence: 82%

Total Synthesis of (±)‐Integrifolin

Shimomaki

Kusama

Iwasawa

2016

Chemistry A European J

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“…1. The other purified components (4-12) were identified as ixerin N (4) [7], ixerisoside A (5) [8], ixerin M (6) [7], tectroside (7) [8,13], 8-epidesacylcynaropicrin glucoside (8) [7,14], 8-epiisolipidiol (9, 3β,8β-dihydroxy-guaia-10(14)-en-1α,4β,5α,6β,7α,11βH-12,6αolide) [11,12], 11βH-11,13-dihydrointegrifolin (10, 3β,8β-dihydroxy-guaia-4(15),10(14)-dien-1α,5α,6β,7α, 11βH-12,6α-olide) [15,16], 8β-hydroxy-4β,15-dihydrozaluzanin C (11, 3β,8β-dihydroxy-guaia-10(14),11(13)-dien-1α,4β,5α,6β,7αH-12,6α-olide) [11] and integrifolin (12, 3β,8β-dihydroxy-guaia-4(15),10(14),11 (13)-trien-1α,5α,6β,7αH-12,6α-olide) [17] by direct comparison of their spectral data with those in the literature. Details of the workup procedure and copies of the original spectra of 4-12 are obtainable from the author of correspondence.…”

mentioning

confidence: 99%

New Guaiane Sesquiterpene Lactones fromIxeris dentata

Cha

Choi

et al. 2010

Planta Med

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Three new guaiane-type sesquiterpene lactones (1-3), together with nine related sesquiterpenes (4-12), were isolated from the whole extract of Ixeris dentata (Asteraceae). The chemical structures of isolates 1-12 were established by spectroscopic analyses as 3 β,8 β-dihydroxy-guaia-10(14)-en-1 α,4 α,5 α,6 β,7 α,11 βH-12,6 α-olide (1), ixerin N 6'- O-acetate (2), ixerisoside A 6'- O-acetate (3), ixerin N ( 4), ixerisoside A (5), ixerin M (6), tectroside (7), 8-epidesacylcynaropicrin glucoside (8), 8-epiisolipidiol (9), 11 βH-11,13-dihydrointegrifolin (10) 8 β-hydroxy-4 β,15-dihydrozaluzanin C (11), and integrifolin (12). Compounds 1-12 were evaluated for their inhibitory effect on the proliferation of the cultured human tumor cell lines MES-SA, MES-SA/DX5, HCT-15, and HCT15/CL02 in vitro.

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“…This lactone has been previously reported as a synthetic compound obtained in the controlled acetylation of the natural guaianolide Integrifolin (8-epi-desacylcynaropicrin). 12 The IR spectrum displayed bands at 1750 cm -1 (γ-lactone), at 1730 cm -1 (acetyl group), at 3494 cm -1 (hydroxyl group) and weak bands at 1664, 1641 cm -1 (c=c double bonds). Inspection of the 1 H NMR spectrum of compound 1 indicated several signals very close to those observed in Zaluzanin D 15 .…”

Section: Resultsmentioning

confidence: 99%

“…Their structures were proposed on the basis of spectroscopic data and comparisons of the attributed signals with previously reported data. [12][13][14][15][16][17] Although the occurrence of sesquiterpene lactones is common in species of Mikania, guaianolides have been found in only 3 of the 46 species studied so far, e.g. in M. vitifolia, 18 M. haenkeana 19 and M. mendocina.…”

Section: Introductionmentioning

confidence: 99%