Biosynthetic study of conidiation-inducing factor conidiogenone: heterologous production and cyclization mechanism of a key bifunctional diterpene synthase

References

• Roncal T, Cordobés S, Ugalde U, et al Novel diterpenes with potent conidiation inducing activity. Tetrahedron Lett. 2002;43:6799–6802.
   Web of Science ®Google Scholar
• Roncal T, Cordobés S, Sterner O, et al Conidiation in Penicillium cyclopium is induced by conidiogenone, an endogenous diterpene. Eukaryot Cell. 2002;1:823–829.
   PubMed Web of Science ®Google Scholar
• Du L, Li DH, Zhu TJ, et al New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron. 2009;65:1033–1039.
   Web of Science ®Google Scholar
• Niu SW, Fan ZW, Xie CL, et al Spirograterpene A, a Tetracyclic spiro-diterpene with a fused 5/5/5/5 ring system from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475. J Nat Prod. 2017;80:2174–2177.
   PubMed Web of Science ®Google Scholar
• Niu SW, Fan ZW, Tang XX, et al Cyclopiane-type diterpenes from the deep-sea-derived fungus Penicillium commune MCCC 3A00940. Tetrahedron Lett. 2018;59:375–378.
   Web of Science ®Google Scholar
• Hou SH, Tu YQ, Wang SH, et al Total syntheses of the tetracyclic cyclopiane diterpenes conidiogenone, conidiogenol, and conidiogenone B. Angew Chem Int Edit. 2016;55:4456–4460.
   PubMed Web of Science ®Google Scholar
• Toyomasu T, Tsukahara M, Kaneko A, et al Fusicoccins are biosynthesized by an unusual chimera diterpene synthase in fungi. Proc Natl Acad Sci U S A. 2007;104:3084–3088.
   PubMed Web of Science ®Google Scholar
• Toyomasu T, Kaneko A, Tokiwano T, et al Biosynthetic gene-based secondary metabolite screening: a new diterpene, methyl phomopsenonate, from the fungus Phomopsis amygdali. J Org Chem. 2009;74:1541–1548.
   PubMed Web of Science ®Google Scholar
• Chiba R, Minami A, Gomi K, et al Identification of ophiobolin F synthase by a genome mining approach: a sesterterpene synthase from Aspergillus clavatus. Org Lett. 2013;15:594–597.
   PubMed Web of Science ®Google Scholar
• Ye Y, Minami A, Mandi A, et al Genome mining for sesterterpenes using bifunctional terpene synthases reveals a unified intermediate of di/sesterterpenes. J Am Chem Soc. 2015;137:11846–11853.
   PubMed Web of Science ®Google Scholar
• Qin B, Matsuda Y, Mori T, et al An unusual chimeric diterpene synthase from Emericella variecolor and its functional conversion into a sesterterpene synthase by domain swapping. Angew Chem Int Ed Engl. 2016;55:1658–1661.
   PubMed Web of Science ®Google Scholar
• Matsuda Y, Mitsuhashi T, Quan Z, et al Molecular basis for stellatic acid biosynthesis: A genome mining approach for discovery of sesterterpene synthases. Org Lett. 2015;17:4644–4647.
   PubMed Web of Science ®Google Scholar
• Okada M, Matsuda Y, Mitsuhashi T, et al Genome-based discovery of an unprecedented cyclization mode in fungal sesterterpenoid biosynthesis. J Am Chem Soc. 2016;138:10011–10018.
   PubMed Web of Science ®Google Scholar
• Matsuda Y, Mitsuhashi T, Lee S, et al Astellifadiene: structure determination by NMR spectroscopy and crystalline sponge method, and elucidation of its biosynthesis. Angew Chem Int Ed Engl. 2016;55:5785–5788.
   PubMed Web of Science ®Google Scholar
• Bian G, Han Y, Hou A, et al Releasing the potential power of terpene synthases by a robust precursor supply platform. Metab Eng. 2017;42:1–8.
   PubMed Web of Science ®Google Scholar
• Mitsuhashi T, Rinkel J, Okada M, et al Mechanistic characterization of two chimeric sesterterpene synthases from Penicillium. Chemistry. 2017;23:10053–10057.
   PubMed Web of Science ®Google Scholar
• Renner MK, Jensen PR, Fenical W. Mangicols: structures and biosynthesis of a new class of sesterterpene polyols from a marine fungus of the genus Fusarium. J Org Chem. 2000;65:4843–4852.
   PubMed Web of Science ®Google Scholar
• Shinde SS, Minami A, Chen Z, et al Cyclization mechanism of phomopsene synthase: mass spectrometry based analysis of various site-specifically labeled terpenes. J Antibiot (Tokyo). 2017;70:632–638.
   PubMed Web of Science ®Google Scholar
• Lauterbach L, Rinkel J, Dickschat JS. Two bacterial diterpene synthases from Allokutzneria albata produce bonnadiene, phomopsene, and allokutznerene. Angew Chem Int Edit. 2018;57:8280–8283.
   PubMed Web of Science ®Google Scholar
• Sugai Y, Miyazaki S, Mukai S, et al Enzymatic total synthesis of gibberellin A4 from acetate. Biosci Biotech Bioch. 2011;75:128–135.
   PubMed Web of Science ®Google Scholar
• Shimane M, Ueno Y, Morisaki K, et al Molecular evolution of the substrate specificity of ent-kaurene synthases to adapt to gibberellin biosynthesis in land plants. Biochem J. 2014;462:539–546.
   PubMed Web of Science ®Google Scholar
• Minami A, Ozaki T, Liu C, et al. Cyclopentane-forming di/sesterterpene synthases: widely distributed enzymes in bacteria, fungi, and plants. Nat Prod Rep. 2018. DOI:10.1039/c8np00026c
   PubMed Web of Science ®Google Scholar
• Lodewyk MW, Siebert MR, Tantillo DJ. Computational prediction of 1H and 13C chemical shifts: A useful tool for natural product, mechanistic, and synthetic organic chemistry. Chem Rev. 2012;112:1839–1862.
   PubMed Web of Science ®Google Scholar
• Nguyen QNN, Tantillo DJ. Using quantum chemical computations of NMR chemical shifts to assign relative configurations of terpenes from an engineered Streptomyces host. J Antibiot. 2016;69:534–540.
   PubMed Web of Science ®Google Scholar
• Hong YJ, Tantillo DJ. Is a 1,4-alkyl shift involved in the biosynthesis of ledol and viridiflorol? J Org Chem. 2017;82:3957–3959.
   PubMed Web of Science ®Google Scholar
• Sugai Y, Ueno Y, Hayashi K, et al Enzymatic 13C labeling and multidimensional NMR analysis of miltiradiene synthesized by bifunctional diterpene cyclase in Selaginella moellendorffii. J Biol Chem. 2011;286:42840–42847.
   PubMed Web of Science ®Google Scholar
• Halgren TA. Merck molecular force field .1. Basis, form, scope, parameterization, and performance of MMFF94. J Comput Chem. 1996;17:490–519.
   Web of Science ®Google Scholar