Abstract
Vitamin K is classified into three homologs depending on the side-chain structure, with 2-methyl-1,4-naphthoqumone as the basic skeleton. These homologs are vitamin K1 (phylloquinone: PK), derived from plants with a phythyl side chain; vitamin K2 (menaquinone-n: MK-n), derived from intestinal bacteria with an isoprene side chain; and vitamin K3 (menadione: MD), a synthetic product without a side chain. Vitamin K homologs have physiological effects, including in blood coagulation and in osteogenic activity via γ-glutamyl carboxylase and are used clinically. Recent studies have revealed that vitamin K homologs are converted to MK-4 by the UbiA prenyltransferase domain-containing protein 1 (UBIAD1) in vivo and accumulate in all tissues. Although vitamin K is considered to have important physiological effects, its precise activities and mechanisms largely remain unclear. Recent research on vitamin K has suggested various new roles, such as transcriptional activity as an agonist of steroid and xenobiotic nuclear receptor and differentiation-inducing activity in neural stem cells. In this review, we describe synthetic ligands based on vitamin K and exhibit that the strength of biological activity can be controlled by modification of the side chain part.
Highlights
Vitamin K plays an important role in blood coagulation and bone formation and has been clinically applied for the treatment and prevention of bleeding and osteoporosis
Because the structure of MK-4 can be roughly divided into a 2-methyl-1,4-naphthoquinone ring and chain, we focused on the features of the ring structure and the side-chain structure of vitamin K and a geranylgeranyl side chain, we focused on the features of the ring structure and the side-chain its various homologs
We recently reported that MKs show weak activity in differentiation of progenitor cells to neuronal cells [45], which depended on the number of isoprene driving the differentiation of progenitor cells to neuronal cells [45], which depended on the number units of the side chain in the vitamin K homolog
Summary
Vitamin K plays an important role in blood coagulation and bone formation and has been clinically applied for the treatment and prevention of bleeding and osteoporosis. This compound is classified into various homologs that share a basic skeleton of 2-methyl-1,4-naphthoquinone and differ by side-chain structure [1,2]. Mice,abundant and rats ingest only amounts of MK-4, resolve this apparent inconsistency, we have focused on elucidating the mechanism for converting it is the most abundant vitamin K homolog in the tissues. Further modification of the side-chain structure is anticipated from synthesis of vitamin derivatives that yield stronger activity. GGCX and other factors [31]
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