Biomimetic Transformations of 11,13-Dihydroparthenolide and Oxidative Rearrangements ofa Guai- 1(10)-en-6,12-olide

Parodi, Felix J.; Fronczek, Frank R.; Fischer, Nikolaus H.

doi:10.1021/np50063a014

Cited by 17 publications

(13 citation statements)

References 14 publications

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“…Compound (1) was prepared by the BF3-mediated rearrangement of l l~H, 13-dihydroparthenolide (Parodi, Fronczek & Fischer, 1989). Crystals were grown from ethyl acetatehexane.…”

Section: Methodsmentioning

confidence: 99%

The Guaianolide 11βH,13-Dihydromicheliolide

Castañeda‐Acosta¹,

Fischer²,

Fronczek³

1996

Acta Crystallogr C

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“…Compound (1) was prepared by the BF3-mediated rearrangement of l l~H, 13-dihydroparthenolide (Parodi, Fronczek & Fischer, 1989). Crystals were grown from ethyl acetatehexane.…”

Section: Methodsmentioning

confidence: 99%

The Guaianolide 11βH,13-Dihydromicheliolide

Castañeda‐Acosta¹,

Fischer²,

Fronczek³

1996

Acta Crystallogr C

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“…1). All compounds were identified based on 1 H-NMR comparison with literature, 2D-COSY, and high-resolution MS [15,[22][23][24][25][26][27][28][29][30]. The purest samples of each SL were selected for the hPAP assay (l " Fig.…”

mentioning

confidence: 99%

“…This suggests that the differences between the open, germacranolide ring and the bridged, guaianolide ring play an important role in the activity of these compounds. Lewis-acid catalyzed intramolecular cyclization reactions of germanacranolides into guaianolides are known to occur [23,31]. Other biological activities such as anticancer activity and anti-inflammatory action are known to differ between various SL skeletons [5,32].…”

mentioning

confidence: 99%

Activation of Antioxidant Response Element in Mouse Primary Cortical Cultures with Sesquiterpene Lactones Isolated from Tanacetum parthenium

et al. 2012

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Tanacetum parthenium (Asteraceae) produces biologically active sesquiterpene lactones (SL). Nuclear factor E2-related factor 2 (Nrf2) is a transcription factor known to activate a series of genes termed the antioxidant response element (ARE). Activation of the Nrf2/ARE may be useful for the treatment of neurodegenerative disease. In this study we isolated 11 sesquiterpene lactones from T. parthenium with centrifugal partition chromatography and semi-preparative HPLC. Compounds were screened in-vitro for their ability to activate the ARE on primary mouse cortical cultures as well as for their toxicity towards the cultures. All sesquiterpene lactones containing the α-methylene-γ-lactone moiety were able to activate the ARE although a number of compounds displayed significant cellular toxicity towards the cultures. The structure activity relationship of the sesquiterpene lactones indicate that the guaianolides isolated were more active and less toxic then the germacranolides.

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“…61 Rustaiyan et al isolated 8-epi-tomentosin ( 27) and 4,5-dioxo-11b-H-xanth-1(10)-en-12,8b-olide (52) from the aerial parts of Dittrichia graveolens. 62 65 This plant was investigated previously by Bohlmann et al and the isolation of 2-deacetyl-11b,13-dihydroxanthinin (17) was reported, but this was later revised to 11a,13dihydrotomentosin (15). 66 The investigation of the aerial parts of Postia bombycina yielded tomentosin (25).…”

Section: Ratibida Peduncularismentioning

confidence: 99%

“…Thus, guaian-1(10)-en-6,12-olide was transformed by a peroxy-acid-mediated oxidation to 4,5-dioxo-11,13a-xanth-1(10)-en-12,6a-olide. 15 Xanthanolides can be divided into two structural classes according to the lactone ring annelation: 12,6-and 12,8-olides. The members of the latter group occur more widely in plants and can be further classified depending upon the stereochemistry at C-8.…”

Section: Introductionmentioning

confidence: 99%