Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

Sommerwerk, Sven; Heller, Lucie; Siewert, Bianka; Csuk, René

doi:10.1016/j.bmc.2015.07.031

Cited by 5 publications

(4 citation statements)

References 42 publications

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“…6S in the Electronic Supplementary Materials). The chemical identity of the compound was additionally verified through comparison to published chemical shift values [26]. Like anhydrosugars, unsaturated compounds including (2E)-2,4-pentadienal are early intermediates in the pyrolysis of biomass [27].…”

Section: Dehydration Reactions Different From Hmf Formationmentioning

confidence: 98%

Uncharted Pathways for CrCl3 Catalyzed Glucose Conversion in Aqueous Solution

et al. 2019

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Section: Dehydration Reactions Different From Hmf Formationmentioning

confidence: 98%

Uncharted Pathways for CrCl3 Catalyzed Glucose Conversion in Aqueous Solution

et al. 2019

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“…Bupleurotoxin is closely related to oenanthotoxin (94) that occurs in Oenanthe species such as O. crocata [154]. Oenanthotoxin has been tested for its cytotoxicity against six different human cancer cell lines but did only show significant cytotoxicity against an ovarian adenocarcinoma (A2780) cell line with an EC 50 (half maximal effective concentration) value of 3.8 µM, and moderate cytotoxicity against thyroid carcinoma (8505C) and alveolar basal epithelial adenocarcinoma (A549) cell lines with EC 50 values around 10 µM [155]. In the same study, synthetic analogues of oenanthotoxin did not result in any improvement of the cytotoxicity compared to oenanthotoxin, and therefore the results are not included.…”

Section: Cytotoxic C 17 and C 18 Acetylenic Oxylipins From Apiaceae Mmentioning

confidence: 99%

“…In the same study, synthetic analogues of oenanthotoxin did not result in any improvement of the cytotoxicity compared to oenanthotoxin, and therefore the results are not included. However, a full description of their activity can be found in [155]. Based on the above studies, it appears that the toxic polyacetylenes from Bupleurum and Oenanthe species are not obvious sources for interesting new cytotoxic acetylenic oxylipins.…”

Section: Cytotoxic C 17 and C 18 Acetylenic Oxylipins From Apiaceae Mmentioning

confidence: 99%

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Christensen

2020

Molecules

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Bioactive C17 and C18 acetylenic oxylipins have shown to contribute to the cytotoxic, anti-inflammatory, and potential anticancer properties of terrestrial plants. These acetylenic oxylipins are widely distributed in plants belonging to the families Apiaceae, Araliaceae, and Asteraceae, and have shown to induce cell cycle arrest and/or apoptosis of cancer cells in vitro and to exert a chemopreventive effect on cancer development in vivo. The triple bond functionality of these oxylipins transform them into highly alkylating compounds being reactive to proteins and other biomolecules. This enables them to induce the formation of anti-inflammatory and cytoprotective phase 2 enzymes via activation of the Keap1–Nrf2 signaling pathway, inhibition of proinflammatory peptides and proteins, and/or induction of endoplasmic reticulum stress, which, to some extent, may explain their chemopreventive effects. In addition, these acetylenic oxylipins have shown to act as ligands for the nuclear receptor PPARγ, which play a central role in growth, differentiation, and apoptosis of cancer cells. Bioactive C17 and C18 acetylenic oxylipins appear, therefore, to constitute a group of promising lead compounds for the development of anticancer drugs. In this review, the cytotoxic, anti-inflammatory and anticancer effects of C17 and C18 acetylenic oxylipins from terrestrial plants are presented and their possible mechanisms of action and structural requirements for optimal cytotoxicity are discussed.

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“…It is in line with the predominant E,Econfiguration of the natural products that most synthetic efforts have also addressed this configuration. 18 For example, (E)dihaloethenes have been elaborated into E,E-configured diene− diynes with retention of the configuration through successive Pdcatalyzed cross-coupling reactions. 17,19−21 A rare example for the stereoselective synthesis of an E,Z-diene−yne sequence was published by Taylor and co-workers in the course of a synthesis of the marine polyacetylene metabolite carduusyne A.…”

mentioning

confidence: 99%

Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne

Schmidt

Audörsch

2016

Org. Lett.

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The first total synthesis of the polyacetylene natural product atractylodemayne A is reported. Stereoselective construction of the conjugated 8(Z),10(E)-diene moiety was achieved through a tethered ring-closing metathesis approach, comprising a Ru-catalyzed RCM followed by a base-induced elimination. A Pd-catalyzed Cadiot-Chodkiewicz coupling was used for the synthesis of the diyne. Overall, atractylodemayne A was synthesized in nine steps for the longest linear sequence.

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Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

Cited by 5 publications

References 42 publications

Uncharted Pathways for CrCl3 Catalyzed Glucose Conversion in Aqueous Solution

Uncharted Pathways for CrCl3 Catalyzed Glucose Conversion in Aqueous Solution

Bioactive C17 and C18 Acetylenic Oxylipins from Terrestrial Plants as Potential Lead Compounds for Anticancer Drug Development

Stereoselective Total Synthesis of Atractylodemayne A, a Conjugated 2(E),8(Z),10(E)-Triene-4,6-diyne

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