Beilstein J. Org. Chem.2025,21, 1489–1495, doi:10.3762/bjoc.21.111
enzymatic terpene cyclization and chemical synthesis [30][31][32][33]. Briefly, the carbon scaffolds are forged by terpene cyclases, followed by concise chemical transformations to yield the desired natural products. Here, we describe heterologousbiosynthesis of cotylenol by engineering the biosynthetic
diterpenoids, including alterbrassicicene E and brassicicenes A and R in 4 or 5 chemical steps from brassicicene I. This strategy lays the foundation for the preparation of fusicoccane diterpenoids and their analogues for biological studies.
Keywords: cotylenol; fusicoccane diterpenoids; heterologous
biosynthesis; P450 oxidation; synthesis; Introduction
Fusicoccanes are a family of 5-8-5 tricyclic diterpenoid natural products that are produced by bacteria, fungi, algae, and plants (Figure 1a) [1][2][3][4][5][6][7]. Fusicoccanes possess a broad range of biological activities, including anticancer, anti
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Graphical Abstract
Figure 1:
Selected fusicoccane diterpenoids and overview of this study. (a) Representative members of the fus...
Beilstein J. Org. Chem.2024,20, 741–752, doi:10.3762/bjoc.20.68
cell suspension culture, heterologousbiosynthesis, and total synthesis [16][17]. Crocins can be obtained from plant cell culture, but the production is prone to epigenetic silencing and toxic intermediates. The chemical synthesis of crocins is challenging due to the presence of numerous chiral centers
adjusting the molar ratio of CsCCD2-M1 and SynALD in the system, the yield of crocetin (1) reached 5.92 mg/L with a conversion rate of 80.8% [110].
Heterologousbiosynthesis of crocins
The heterologous production of crocins has been achieved in various hosts, including E. coli, N. benthamiana, and S
produced crocins were not reported. Heterologousbiosynthesis of crocins was also attempted in Nicotiana tabacum and Lycopersicon esculentum [85]. Because CsCCD2L exhibited high CCD activity against zeaxanthin (7), Martí et al. used a virus-driven transduction system to transfer CsCCD2L, PaCrtB (the gene
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Graphical Abstract
Figure 1:
Principal structure of crocin and crocetin derivatives, including common substituents of the crocet...