Terpenoids and Their Biosynthesis in Cyanobacteria

Overview

Journal Life (Basel)

Specialty Biology

Date 2015 Jan 24

PMID 25615610

Citations 49

Authors

Bagmi Pattanaik

Pia Lindberg

Affiliations

Soon will be listed here.

Abstract

Terpenoids, or isoprenoids, are a family of compounds with great structural diversity which are essential for all living organisms. In cyanobacteria, they are synthesized from the methylerythritol-phosphate (MEP) pathway, using glyceraldehyde 3-phosphate and pyruvate produced by photosynthesis as substrates. The products of the MEP pathway are the isomeric five-carbon compounds isopentenyl diphosphate and dimethylallyl diphosphate, which in turn form the basic building blocks for formation of all terpenoids. Many terpenoid compounds have useful properties and are of interest in the fields of pharmaceuticals and nutrition, and even potentially as future biofuels. The MEP pathway, its function and regulation, and the subsequent formation of terpenoids have not been fully elucidated in cyanobacteria, despite its relevance for biotechnological applications. In this review, we summarize the present knowledge about cyanobacterial terpenoid biosynthesis, both regarding the native metabolism and regarding metabolic engineering of cyanobacteria for heterologous production of non-native terpenoids.

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References

ESTEVEZ J, Cantero A, Reindl A, Reichler S, Leon P . 1-Deoxy-D-xylulose-5-phosphate synthase, a limiting enzyme for plastidic isoprenoid biosynthesis in plants. J Biol Chem. 2001; 276(25):22901-9. DOI: 10.1074/jbc.M100854200. View

Halfmann C, Gu L, Gibbons W, Zhou R . Genetically engineering cyanobacteria to convert CO₂, water, and light into the long-chain hydrocarbon farnesene. Appl Microbiol Biotechnol. 2014; 98(23):9869-77. DOI: 10.1007/s00253-014-6118-4. View

Sozer O, Komenda J, Ughy B, Domonkos I, Laczko-Dobos H, Malec P . Involvement of carotenoids in the synthesis and assembly of protein subunits of photosynthetic reaction centers of Synechocystis sp. PCC 6803. Plant Cell Physiol. 2010; 51(5):823-35. DOI: 10.1093/pcp/pcq031. View

Sharkey T, Wiberley A, Donohue A . Isoprene emission from plants: why and how. Ann Bot. 2007; 101(1):5-18. PMC: 2701830. DOI: 10.1093/aob/mcm240. View

Poliquin K, Ershov Y, Cunningham Jr F, Woreta T, Gantt R, Gantt E . Inactivation of sll1556 in Synechocystis strain PCC 6803 impairs isoprenoid biosynthesis from pentose phosphate cycle substrates in vitro. J Bacteriol. 2004; 186(14):4685-93. PMC: 438581. DOI: 10.1128/JB.186.14.4685-4693.2004. View

Banthorpe D, Charlwood B, Francis M . The biosynthesis of monoterpenes. Chem Rev. 1972; 72(2):115-55. DOI: 10.1021/cr60276a002. View

Fujioka T, KASHIWADA Y, Kilkuskie R, Cosentino L, Ballas L, Jiang J . Anti-AIDS agents, 11. Betulinic acid and platanic acid as anti-HIV principles from Syzigium claviflorum, and the anti-HIV activity of structurally related triterpenoids. J Nat Prod. 1994; 57(2):243-7. DOI: 10.1021/np50104a008. View

Balcerzak L, Lipok J, Strub D, Lochynski S . Biotransformations of monoterpenes by photoautotrophic micro-organisms. J Appl Microbiol. 2014; 117(6):1523-36. DOI: 10.1111/jam.12632. View

Lindberg P, Park S, Melis A . Engineering a platform for photosynthetic isoprene production in cyanobacteria, using Synechocystis as the model organism. Metab Eng. 2009; 12(1):70-9. DOI: 10.1016/j.ymben.2009.10.001. View

10.

Robert F, Pandhal J, Wright P . Exploiting cyanobacterial P450 pathways. Curr Opin Microbiol. 2010; 13(3):301-6. DOI: 10.1016/j.mib.2010.02.007. View

11.

Doughty D, Hunter R, Summons R, Newman D . 2-Methylhopanoids are maximally produced in akinetes of Nostoc punctiforme: geobiological implications. Geobiology. 2009; 7(5):524-32. PMC: 2860729. DOI: 10.1111/j.1472-4669.2009.00217.x. View

12.

Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A . Local anaesthetic activity of beta-caryophyllene. Farmaco. 2001; 56(5-7):387-9. DOI: 10.1016/s0014-827x(01)01092-8. View

13.

Berry A, Harriott O, Moreau R, Osman S, Benson D, Jones A . Hopanoid lipids compose the Frankia vesicle envelope, presumptive barrier of oxygen diffusion to nitrogenase. Proc Natl Acad Sci U S A. 1993; 90(13):6091-4. PMC: 46873. DOI: 10.1073/pnas.90.13.6091. View

14.

Lois L, Campos N, Putra S, Danielsen K, Rohmer M, Boronat A . Cloning and characterization of a gene from Escherichia coli encoding a transketolase-like enzyme that catalyzes the synthesis of D-1-deoxyxylulose 5-phosphate, a common precursor for isoprenoid, thiamin, and pyridoxol biosynthesis. Proc Natl Acad Sci U S A. 1998; 95(5):2105-10. PMC: 19265. DOI: 10.1073/pnas.95.5.2105. View

15.

Seemann M, Tse Sum Bui B, Wolff M, Miginiac-Maslow M, Rohmer M . Isoprenoid biosynthesis in plant chloroplasts via the MEP pathway: direct thylakoid/ferredoxin-dependent photoreduction of GcpE/IspG. FEBS Lett. 2006; 580(6):1547-52. DOI: 10.1016/j.febslet.2006.01.082. View

16.

Sharkey T, Yeh S . ISOPRENE EMISSION FROM PLANTS. Annu Rev Plant Physiol Plant Mol Biol. 2001; 52:407-436. DOI: 10.1146/annurev.arplant.52.1.407. View

17.

Welander P, Doughty D, Wu C, Mehay S, Summons R, Newman D . Identification and characterization of Rhodopseudomonas palustris TIE-1 hopanoid biosynthesis mutants. Geobiology. 2012; 10(2):163-77. PMC: 3553210. DOI: 10.1111/j.1472-4669.2011.00314.x. View

18.

Umeno D, Tobias A, Arnold F . Evolution of the C30 carotenoid synthase CrtM for function in a C40 pathway. J Bacteriol. 2002; 184(23):6690-9. PMC: 135437. DOI: 10.1128/JB.184.23.6690-6699.2002. View

19.

Tholl D . Terpene synthases and the regulation, diversity and biological roles of terpene metabolism. Curr Opin Plant Biol. 2006; 9(3):297-304. DOI: 10.1016/j.pbi.2006.03.014. View

20.

Banerjee A, Sharkey T . Methylerythritol 4-phosphate (MEP) pathway metabolic regulation. Nat Prod Rep. 2014; 31(8):1043-55. DOI: 10.1039/c3np70124g. View