Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions

Basset, Gilles J.; Latimer, Scott; Fatihi, Abdelhak; Soubeyrand, Eric; Block, Anna

doi:10.2174/1389557516666160623082714

Cited by 74 publications

(49 citation statements)

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“…16 Interestingly, not all of the enzymes have had signicant investigation into potential inhibitors. [18][19][20][21][22][23][24][25][26] To date the most promising results have come from inhibitors targeting the enzymes further downstream of the synthesis pathway. Major inhibitors that have been discovered to date will be reviewed in this article.…”

Section: Bacterial Synthesis Of Menaquinonementioning

confidence: 99%

Menaquinone biosynthesis inhibition: a review of advancements toward a new antibiotic mechanism

et al. 2018

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Section: Bacterial Synthesis Of Menaquinonementioning

confidence: 99%

Menaquinone biosynthesis inhibition: a review of advancements toward a new antibiotic mechanism

et al. 2018

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“…Because the quinone ring (ring B ) of phylloquinone originates from glutamate via α-ketoglutarate (Fig. 1 ) 18 , we therefore assessed the incorporation into juglone of 13 C 5 15 N 1 -labeled l -glutamate (Glu-[ 13 C 5 15 N 1 ]) fed to axenic black walnut root cultures. We predicted that if the naphthalenoid precursor for juglone is derived from the phylloquinone pathway, then juglone should be labeled by Glu-[ 13 C 5 15 N 1 ] with a mass shift of +3 (M3; Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Through a sequential series of phytylation 15 , reduction 16 , and methylation 17 reactions, DHNA is finally converted to phylloquinone (Fig. 1 ) 18 .…”

Section: Introductionmentioning

confidence: 99%

The origin and biosynthesis of the naphthalenoid moiety of juglone in black walnut

et al. 2018

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Several members of the Juglandaceae family produce juglone, a specialized 1,4-naphthoquinone (1,4-NQ) natural product that is responsible for the notorious allelopathic effects of black walnut (Juglans nigra). Despite its documented ecological roles and potential for being developed as a novel natural product-based herbicide, none of the genes involved in synthesizing juglone have been identified. Based on classical labeling studies, we hypothesized that biosynthesis of juglone’s naphthalenoid moiety is shared with biochemical steps of the phylloquinone pathway. Here, using comparative transcriptomics in combination with targeted metabolic profiling of 1,4-NQs in various black walnut organs, we provide evidence that phylloquinone pathway genes involved in 1,4-dihydroxynaphthoic acid (DHNA) formation are expressed in roots for synthesis of a compound other than phylloquinone. Feeding experiments using axenic black walnut root cultures revealed that stable isotopically labeled l-glutamate incorporates into juglone resulting in the same mass shift as that expected for labeling of the quinone ring in phylloquinone. Taken together, these results indicate that in planta, an intermediate from the phylloquinone pathway provides the naphthalenoid moiety of juglone. Moreover, this work shows that juglone can be de novo synthesized in roots without the contribution of immediate precursors translocated from aerial tissues. The present study illuminates all genes involved in synthesizing the juglone naphthoquinone ring and provides RNA-sequencing datasets that can be used with functional screening studies to elucidate the remaining juglone pathway genes. Translation of the generated knowledge is expected to inform future metabolic engineering strategies for harnessing juglone as a novel natural product-based herbicide.

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“…Witamina K należy do witamin rozpuszczalnych w tłuszczach. W żywności występuje w postaci synte tyzowanego przez rośliny filochinonu (witamina K 1 ) oraz zawartych w produktach zwierzęcych menachinonów (witamina K 2 , MK) [56]. Filochinon jest obecny przede wszystkim w zielonych warzywach liściastych i kapustnych, menachinony natomiast w mięsie, serze i jajach i są wytwarzane przez bak terie jelitowe [57].…”

Section: Witamina Kunclassified

Vitamin supplementation in oncological patients. Part II – vitamin C, fat-soluble vitamins and the elements calcium and iron

Badian¹,

Dzierżanowski²

2018

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Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions

Abstract: This review presents an update on recent studies of the central role of plastids in the biosynthesis of phylloquinone, in particular on the discovery of novel enzymatic steps that are likely paradigms for phylloquinone and menaquinone (vitamin K2)-synthesizing organisms alike.

Cited by 74 publications

References 0 publications

Menaquinone biosynthesis inhibition: a review of advancements toward a new antibiotic mechanism

Menaquinone biosynthesis inhibition: a review of advancements toward a new antibiotic mechanism

The origin and biosynthesis of the naphthalenoid moiety of juglone in black walnut

Vitamin supplementation in oncological patients. Part II – vitamin C, fat-soluble vitamins and the elements calcium and iron

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