Structural diversity, biosynthesis, and function of plant falcarin-type polyacetylenic lipids

Abstract

The polyacetylenic lipids falcarinol, falcarindiol, and associated derivatives, termed falcarins, have a widespread taxonomical distribution in the plant kingdom and have received increasing interest for their demonstrated health-promoting properties as anti-cancer and anti-inflammatory agents. These fatty acid-derived compounds are also linked to plant pathogen resistance through their potent antimicrobial properties. Falcarin-type polyacetylenes, which contain two conjugated triple bonds, are derived from structural modifications of the common fatty acid oleic acid. In the past half century, much progress has been made on understanding the structural diversity of falcarins in the plant kingdom, while limited progress has been made on elucidating falcarin function in plant-pathogen interactions. More recently, an understanding of the biosynthetic machinery underlying falcarin biosynthesis has emerged. This review provides a concise summary of the current state of knowledge on falcarin structural diversity, biosynthesis, and plant defense properties. We also present major unanswered questions about falcarin biosynthesis and function.

Identification of resistance to black spot disease and potential defense mechanisms in Chrysanthemum-related genera

“…In addition, Pinus nigra volatile oil rich in terpenoids (Germacrene D-4-ol) and structurally similar terpenoids (Germacrene D) had inhibitory effects against Aspergillus niger and Bacillus subtilis (Sarac et al, 2014). Falcarinol was thought to act as a plant chemical defense agent to thwart infection by devastating pathogens (Santos et al, 2022). Falcarinol was also bene cial to human health because of its outstanding pharmacological effects (Dawid et Based on the evidence from this work, it would be seen that Germacrene D and falcarinol, which had antifungal activity in R2, might play a direct defense role in response to A. alternata mycelial invasion.…”

Phenyl dialkynylcarbinols, a Bioinspired Series of Synthetic Antitumor Acetylenic Lipids

“…13 C NMR (125 MHz, CDCl 3 ): δ (ppm) 147.2 (q, J = 1.6 Hz), 136.2, 130.6, 129.9, 123.5 (q, J = 1.6 Hz), 121.4, 120.6 (q, J = 257. 6 3- (3,7,phenyl)prop-2-yn-1-ol (27e). The crude mixture was purified by flash column chromatography using up to 30% diethyl ether in pentane.…”

Variation on a theme: the structures and biosynthesis of specialized fatty acid natural products in plants

“…Accordingly, the bioactivities of these compounds have been the subject of considerable study, which has led to the discovery that they have a variety of nutraceutical properties (Christensen & Brandt, 2006). Several reviews document the diverse structures of polyacetylenes, including structures of polyacetylenes from across the plant kingdom (Negri, 2015), specific core areas of the chemical space (Santos et al., 2022), and structures from specific groups such as the Asteraceae (Konovalov, 2014), the Apiaceae (Chen et al., 2015), and, for example, the genus Daucus (Dawid et al., 2015) and the genus Bupleurum (Lin et al., 2016). Here, we provide a general overview of those findings and describe polyacetylene structures and biosynthesis from across the plant kingdom.…”