Marine Polyacetylenes: Distribution, Biological Properties, and Synthesis

Legrave, Nathalie; Fahmi, Elsebai Mahmoud; Mendili, Mohamed; Amade, Philippe

doi:10.1016/b978-0-444-63473-3.00008-3

Cited by 5 publications

(5 citation statements)

References 97 publications

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“…Polyacetylenes are widely distributed in nature, occurring in terrestrial plants, fungi, bacteria, mosses, lichens, marine algae, and invertebrates. The majority of polyacetylenes are characterized by a long hydrocarbon chain consisting of 10 to 42 carbons, and among these, C 17 and C 18 -polyacetylenes have often been reported to possess potential anticancer effects [1][2][3][4][5]. More than 2500 polyacetylenes are known, of which the majority have been isolated from terrestrial plants and, in particular, from the botanically related plant families Apiaceae, Araliaceae, and Asteraceae [1,3].…”

Section: Introductionmentioning

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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Section: Introductionmentioning

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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“…All reactions were carried out under a dry argon atmosphere. 1 H and 13 C NMR spectra were obtained using a Bruker AVANCE 400 spectrometer in CDCl 3 operating at 400 MHz for 1 H and 100 MHz for 13 C. High-resolution mass spectra (HRMS) were measured on an instrument using a time-of-flight (TOF) mass analyzer with electrospray ionization (ESI). Elemental analyses were performed on an 1106 Carlo Erba apparatus.…”

Section: Methodsmentioning

confidence: 99%

“…(13Z,17Z)-Tetraconta-13,17-dien-1-al (4). 1 H NMR (400 MHz) δ 0.88 (3H, t, J = 6.6 Hz, CH 3 ), 1.42− 1.15 (44H, m, CH 2 ), 1.56−1.66 (2H, m, CH 2 ), 1.96−2.10 (8H, m, CH 2 −CH), 2.40 (2H, t, J = 7.3 Hz,), 5.41−5.32 (4H, m, J = 5.4 Hz,), 9.74 (1H, s, OCH). 13 5).…”

Section: Methodsmentioning

confidence: 99%

“…Higher acetylenic alcohols and their derivatives are encountered in many plants, algae, marine invertebrates, and higher fungus species, − and more than 1000 acetylenic compounds have been isolated and identified to date. For many years, increasing interest has been shown in these organic compounds, largely owing to the important biological activities they exhibit, in particular, antitumor, antimicrobial, antiparasitic, antibacterial, antifungal, and other types of activities. − …”

Section: Introductionmentioning

confidence: 99%

“…Among the diverse alkynol derivatives known to date, derivatives of carbinols containing one or several triple bonds in the α-position to the hydroxy group are the most abundant. − …”

Section: Introductionmentioning

confidence: 99%

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New 1,3-Diynoic Derivatives of Natural Lembehyne B: Stereoselective Synthesis, Anticancer, and Neuritogenic Activity

et al. 2020

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An original method has been developed for the synthesis of 1,3-dyine derivatives of natural lembehyne B in high yields (50–67%) and with high selectivity (>98%). The key stage of the synthesis is new Ti-catalyzed cross-cyclomagnesiation of oxygenated and aliphatic 1,2-dienes induced by Grignard reagents. For studying the effect of the structure on the antitumor and neuritogenic activities, a series of lembehyne B analogues with different distances between the terminal hydroxy group and the 1,3-diyne moiety was prepared and tested for neuritogenic activity on mouse neuroblastoma Neuro 2A cells and for cytotoxicity, induction of apoptosis, and effects on the cell cycle using Jurkat, U937, K562, HeLa, and Hek293 tumor cell lines.

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DFT mechanistic investigation of the 1,2‐reduction of α,β‐unsaturated ynones

2022

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The reaction mechanism of the phosphane catalyzed chemoselective 1,2-reduction of ynones using pinacolborane has been explored computationally. Numerous plausible reaction routes were investigated, and calculations based on density function theory showed that the hydride transfer to the vinylphosphonium cations in the catalytic cycle leads to dead-ends. The in situ formed dioxaborolane acts as the hydride donor and the reaction proceeds on a parallel path. Alternative mechanisms have also been examined alongside the crucial role of theoretical levels, moreover, the effect of a solvent was taken into consideration by applying the implicit polarizable continuum model.

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Marine Polyacetylenes: Distribution, Biological Properties, and Synthesis

Cited by 5 publications

References 97 publications

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

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

New 1,3-Diynoic Derivatives of Natural Lembehyne B: Stereoselective Synthesis, Anticancer, and Neuritogenic Activity

DFT mechanistic investigation of the 1,2‐reduction of α,β‐unsaturated ynones

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