Peroxycostunolide and peroxyparthenolide: two cytotoxic germacranolide hydroperoxides from . Structural revision of verlotorin and artemorin.

El-Feraly, S.; Chan, Yee-Ming; Fairchild, Edward H.; Doskotch, Raymond W.

doi:10.1016/s0040-4039(01)83656-x

Cited by 29 publications

(23 citation statements)

References 7 publications

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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.…”

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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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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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“…The sesquiterpene lactones in the bark and leaves are also effective deterrents against insects (Castro et al, 2000) and phytopathogens (Fischer, 1991). Besides parthenolide and costunolide, peroxyparthenolide and peroxycostunolide were also found in M. grandiflora (El-Feraly et al, 1977. These compounds also show considerable cytotoxic activity.…”

Section: Sesquiterpene Lactonesmentioning

confidence: 93%

The Ethnomedicinal Uses of Magnoliaceae from the Southeastern United States as Leads in Drug Discovery

Schühly

Khan

Fischer

2001

Pharmaceutical Biology

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In Asia and North America, members of the family Magnoliaceae have been and are presently used extensively in indigenous herbal medicine. Many taxa of the genus Magnolia produce lignans and sesquiterpene lactones, some with considerable in vitro bioactivities. This review focuses on selected natural products of the genus Magnolia from the southeastern United States with demonstrated biological and pharmacological properties. Ethnomedicinal data obtained from the Native Americans of the southeastern United States correlate well with the results of pharmacological investigations.

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“…The desired material was finally secured by acetylating deacetyllaurenobiolide (1 0) which was isolated in in one pair and a in the other, it was expected that its sensitized photo-oxygenation would yield more than one hydroperoxide. Indeed two products were produced (Scheme 2), the first one, (12), was obtained as colourless needles, m.p. 148-149 "C (with bubbling), while the other one, (ll), occurred as a colourless oil which was still partially contaminated with (12).…”

Section: Biogenetic-type Synthesis Of Santoninmentioning

confidence: 99%

“…Singlecrystal X-ray analyses unequivocally established the 1 S configuration in dihydrochrysanolide (1 4) and its hydroperoxy-analogue (1 2). lsomorphous crystals of (1 2) and (1 4) belong to the monoclinic system, space group P 2 , , with a = 14.350 (6), b = 5.882 (3), c = 10.343(3) A, p = 107.64(2)", Z = 2, for (12), and a = 14.461 (6), b = 5.887 (3), c = 9.698(4) A, p = 107.44(2)", 2 = 2, for (14). Least-squares refinement of atomic parameters converged to R 0.040 for (1 2) and 0.033 for (1 4) over 1 484 and 1 300 reflections, respectively, measured by diffractometer.…”

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confidence: 99%

Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin

El‐Feraly¹,

Benigni²,

McPhail³

1983

J. Chem. Soc., Perkin Trans. 1

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Peroxycostunolide and peroxyparthenolide: two cytotoxic germacranolide hydroperoxides from . Structural revision of verlotorin and artemorin.

Cited by 29 publications

References 7 publications

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

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

The Ethnomedicinal Uses of Magnoliaceae from the Southeastern United States as Leads in Drug Discovery

Biogenetic-type synthesis of santonin, chrysanolide, dihydrochrysanolide, tulirinol, arbusculin-C, tanacetin, and artemin

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