Polydatin and its derivatives inhibit fatty acid desaturases in microorganisms

Abstract

Antioxidant plant polyphenols resveratrol and its glycoside polydatin at 500 μg/L were found to have two distinct effects on yeasts and algae depending on the cell content of polyunsaturated fatty acids (PUFA). In yeasts that do not produce PUFA, resveratrol (0.5 mg/L) increased resistance to biosynthesized ethanol (an important property in winemaking) to 22% EtOH in Saccharomyces cerevisiae and 14% EtOH in Torulaspora delbrückii, the fatty acid content being changed only slightly, whereas in the PUFA‐producing algae Desmodesmus quadricauda and Euglena gracilis both compounds act as inhibitors of Δ4 desaturases blocking the formation of both even‐ and odd‐numbered PUFA having the first double‐bond in position 4. This leads to the biotechnologically desirable accumulation of the health‐beneficial polyunsaturated fatty acids (PUFAs), docosapentaenoic (DPA), and docosahexaenoic acid (DHA). Practical applications: Employing natural stilbene compounds has far‐reaching use in biotechnological applications such as the production of ethanol used for biofuels or production of wine and beer. It allows the production of beer with higher alcohol content, without resorting to the use of consumer‐unacceptable genetically modified yeast. In brewing, when the yeast is often repeatedly reused to ferment fresh wort, higher resistance of yeast in the presence of these compounds can lead to an increase in the number of yeast reuses and thereby reduce economic costs of the brewery needed for preparation of inocula. Using polydatin as inhibitor of Δ4 desaturase in Euglena and Desmodesmus algae blocks the biosynthesis of both even‐ and odd‐numbered PUFAs having a double bond in position 4. This leads to a change in the content of fatty acids and accumulation of biosynthetic precursors, e.g., 22:5n‐3 acid that has more favorable pharmacological effects than docosahexaenoic acid (22:6n‐3) Natural stilbenes such as polydatin and resveratrol have not yet been known as inhibitors of desaturases. We found that they alter the fatty acid composition in microorganisms containing PUFA (algae) by inhibiting Δ4 desaturase and thus blocking the biosynthesis of specific PUFAs. Inhibition of Δ4 desaturase produces oils with a higher proportion of DPA. Moreover, these compounds increase yeast resistance to ethanol.

Antifeedant Activities of Lignans from Stem Bark of Zanthoxylum armatum DC. against Tribolium castaneum

“…Salicifoliol ( 9 ), magnone A ( 11 ), and planispine A ( 5 ), having no methylenedioxy groups, showed much less or no antifeedant activity. As it was reported, compounds with methylenedioxy groups have various bioactivities, such as improving skin condition, antioxidant activity [ 28 ], anti-inflammatory activity [ 29 ], radical scavenging activity [ 30 ], insecticidal activity [ 31 ], antineuroinflammatory effects [ 32 ], antiparasitic activity, and anti-osteoporotic activity [ 33 ]. Therefore, methylenedioxy, as an active chemical group, may play a key role in antifeedant activities.…”

Microalgal polyunsaturated fatty acids: Hotspots and production techniques

“…The synthetic pathways of PUFAs in algae are relatively wellunderstood, and many desaturases and elongases in algae or other species have been identified. Additionally, the enzymes present in algae have also provided crucial information for the synthesis pathways of omega-3 PUFA in other species, such as fungi and plants (Rezanka et al, 2017). Compared to the fermentation mode and genetic engineering of yeast and other microorganisms, the tools available for algae still need to be developed (Xue et al, 2013;Xie et al, 2015;Khera and Srivastava, 2022).…”