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Ancient plant-like terpene biosynthesis in corals

Nature Chemical Biology volume 18, pages 664–669 (2022)Cite this article

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Abstract

Octocorals are major contributors of terpenoid chemical diversity in the ocean. Natural products from other sessile marine animals are primarily biosynthesized by symbiotic microbes rather than by the host. Here, we challenge this long-standing paradigm by describing a monophyletic lineage of animal-encoded terpene cyclases (TCs) ubiquitous in octocorals. We characterized 15 TC enzymes from nine genera, several of which produce precursors of iconic coral-specific terpenoids, such as pseudopterosin, lophotoxin and eleutherobin. X-ray crystallography revealed that coral TCs share conserved active site residues and structural features with bacterial TCs. The identification of coral TCs enabled the targeted identification of the enzyme that constructs the coral-exclusive capnellane scaffold. Several TC genes are colocalized with genes that encode enzymes known to modify terpenes. This work presents an example of biosynthetic capacity in the kingdom Animalia that rivals the chemical complexity generated by plants, unlocking the biotechnological potential of octocorals for biomedical applications.

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Fig. 1: Bioactive terpenoids extracted from different octocorals linked to their proposed biosynthetic precursor terpenes.
Fig. 2: Phylogeny of octocoral TCs and their terpene products.
Fig. 3: Structure of the coral cembrene A synthase ErTC-2 and other TCs.
Fig. 4: Possible timeline of TC evolution in octocorals.
Fig. 5: Directed approach to the discovery of capnellene synthase CiTC-1.

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Data availability

Shotgun sequencing reads for C. imbricata are available at NCBI SRA under project accession PRJNA761189. The crystal structure of ErTC-2 has been deposited at PDB under the accession number 7S5L. NMR and electron ionization MS spectra of characterized compounds are available in the Supplementary Information. Structure elucidation data are shown in Supplementary Note 1. Sequences used in this study are listed in Supplementary Note 2. Accession numbers of proteins used for HMM building are listed in Supplementary Table 1. Accession data for the literature genomic and transcriptomic data used in this study are summarized in Supplementary Tables 2 and 3, respectively. Accession data for raw genomic data used for mapping are listed in Supplementary Table 4. Accession numbers for proteins used for the phylogenetic analysis are listed in Supplementary Table 10. The PDB accession numbers for reference protein structures in Fig. 3 are 4LZ0, 3P5R and 5JA0.

References

  1. Christianson, D. W. Structural and chemical biology of terpenoid cyclases. Chem. Rev. 117, 11570–11648 (2017).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Karunanithi, P. S. & Zerbe, P. Terpene synthases as metabolic gatekeepers in the evolution of plant terpenoid chemical diversity. Front. Plant Sci. 10, 1166 (2019).

  3. Dickschat, J. S. Bacterial terpene cyclases. Nat. Prod. Rep. 33, 87–110 (2016).

    Article  CAS  PubMed  Google Scholar 

  4. Quin, M. B., Flynn, C. M. & Schmidt-Dannert, C. Traversing the fungal terpenome. Nat. Prod. Rep. 31, 1449–1473 (2014).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Chen, X. et al. Terpene synthase genes in eukaryotes beyond plants and fungi: occurrence in social amoebae. Proc. Natl Acad. Sci. USA 113, 12132–12137 (2016).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Schiff, P. B., Fant, J. & Horwitz, S. B. Promotion of microtubule assembly in vitro by taxol. Nature 277, 665–667 (1979).

    Article  CAS  PubMed  Google Scholar 

  7. Eckstein-Ludwig, U. et al. Artemisinins target the SERCA of Plasmodium falciparum. Nature 424, 957–961 (2003).

    Article  CAS  PubMed  Google Scholar 

  8. Lyu, C. et al. CMNPD: a comprehensive marine natural products database towards facilitating drug discovery from the ocean. Nucleic Acids Res. 49, D509–D515 (2021).

    Article  CAS  PubMed  Google Scholar 

  9. Giordano, G. et al. Volatile secondary metabolites as aposematic olfactory signals and defensive weapons in aquatic environments. Proc. Natl Acad. Sci. USA 114, 3451–3456 (2017).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Berrue, F. & Kerr, R. G. Diterpenes from gorgonian corals. Nat. Prod. Rep. 26, 681–710 (2009).

    Article  CAS  PubMed  Google Scholar 

  11. Li, G., Dickschat, J. S. & Guo, Y.-W. Diving into the world of marine 2,11-cyclized cembranoids: a summary of new compounds and their biological activities. Nat. Prod. Rep. 37, 1367–1383 (2020).

    Article  PubMed  Google Scholar 

  12. Look, S. A., Fenical, W., Jacobs, R. S. & Clardy, J. The pseudopterosins: anti-inflammatory and analgesic natural products from the sea whip Pseudopterogorgia elisabethae. Proc. Natl Acad. Sci. USA 83, 6238–6240 (1986).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Hassan, H. M. et al. Pachycladins A–E, prostate cancer invasion and migration inhibitory eunicellin-based diterpenoids from the red sea soft coral Cladiella pachyclados. J. Nat. Prod. 73, 848–853 (2010).

    Article  CAS  PubMed  Google Scholar 

  14. Fenical, W., Okuda, R. K., Bandurraga, M. M., Culver, P. & Jacobs, R. S. Lophotoxin: a novel neuromuscular toxin from Pacific sea whips of the genus Lophogorgia. Science 212, 1512–1514 (1981).

    Article  CAS  PubMed  Google Scholar 

  15. Wilson, M. C. et al. An environmental bacterial taxon with a large and distinct metabolic repertoire. Nature 506, 58–62 (2014).

    Article  CAS  PubMed  Google Scholar 

  16. Smith, T. E. et al. Accessing chemical diversity from the uncultivated symbionts of small marine animals. Nat. Chem. Biol. 14, 179–185 (2018).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Sudek, S. et al. Identification of the putative bryostatin polyketide synthase gene cluster from “Candidatus Endobugula sertula”, the uncultivated microbial symbiont of the marine bryozoan Bugula neritina. J. Nat. Prod. 70, 67–74 (2007).

    Article  CAS  PubMed  Google Scholar 

  18. Torres, J. P. & Schmidt, E. W. The biosynthetic diversity of the animal world. J. Biol. Chem. 294, 17684–17692 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Shinzato, C. et al. Using the Acropora digitifera genome to understand coral responses to environmental change. Nature 476, 320–323 (2011).

    Article  CAS  PubMed  Google Scholar 

  20. McCauley, E. P. et al. Highlights of marine natural products having parallel scaffolds found from marine-derived bacteria, sponges, and tunicates. J. Antibiot. 73, 504–525 (2020).

    Article  CAS  Google Scholar 

  21. Mydlarz, L. D., Jacobs, R. S., Boehnlein, J. & Kerr, R. G. Pseudopterosin biosynthesis in Symbiodinium sp., the dinoflagellate symbiont of Pseudopterogorgia elisabethae. Chem. Biol. 10, 1051–1056 (2003).

    Article  CAS  PubMed  Google Scholar 

  22. Frenz-Ross, J. L., Enticknap, J. J. & Kerr, R. G. The effect of bleaching on the terpene chemistry of Plexaurella fusifera: evidence that zooxanthellae are not responsible for sesquiterpene production. Mar. Biotechnol. 10, 572–578 (2008).

    Article  CAS  Google Scholar 

  23. Kohl, A. C. & Kerr, R. G. Identification and characterization of the pseudopterosin diterpene cyclase, elisabethatriene synthase, from the marine gorgonian, Pseudopterogorgia elisabethae. Arch. Biochem. Biophys. 424, 97–104 (2004).

    Article  CAS  PubMed  Google Scholar 

  24. Wei, G. et al. Terpene biosynthesis in red algae is catalyzed by microbial type but not typical plant terpene synthases. Plant Physiol. 179, 382–390 (2019).

    Article  CAS  PubMed  Google Scholar 

  25. Yamada, Y. et al. Terpene synthases are widely distributed in bacteria. Proc. Natl Acad. Sci. USA 112, 857–862 (2015).

    Article  CAS  PubMed  Google Scholar 

  26. Mistry, J. et al. Pfam: the protein families database in 2021. Nucleic Acids Res. 49, D412–D419 (2021).

    Article  CAS  PubMed  Google Scholar 

  27. Jeon, Y. et al. The draft genome of an octocoral, Dendronephthya gigantea. Genome Biol. Evol. 11, 949–953 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Huber, T., Weisheit, L. & Magauer, T. Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms. Beilstein J. Org. Chem. 11, 2521–2539 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Hu, M., Zheng, X., Fan, C. -M. & Zheng, Y. Lineage dynamics of the endosymbiotic cell type in the soft coral Xenia. Nature 582, 534–538 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Krissinel, E. & Henrick, K. Inference of macromolecular assemblies from crystalline state. J. Mol. Biol. 372, 774–797 (2007).

    Article  CAS  PubMed  Google Scholar 

  31. Li, R. et al. Reprogramming the chemodiversity of terpenoid cyclization by remolding the active site contour of epi-isozizaene synthase. Biochemistry 53, 1155–1168 (2014).

    Article  CAS  PubMed  Google Scholar 

  32. Köksal, M., Jin, Y., Coates, R. M., Croteau, R. & Christianson, D. W. Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis. Nature 469, 116–120 (2011).

    Article  PubMed  CAS  Google Scholar 

  33. Park, J., Zielinski, M., Magder, A., Tsantrizos, Y. S. & Berghuis, A. M. Human farnesyl pyrophosphate synthase is allosterically inhibited by its own product. Nat. Commun. 8, 14132 (2017).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Lancaster, J. et al. De novo formation of an aggregation pheromone precursor by an isoprenyl diphosphate synthase-related terpene synthase in the harlequin bug. Proc. Natl Acad. Sci. USA 115, E8634–E8641 (2018).

    CAS  PubMed  PubMed Central  Google Scholar 

  35. McFadden, C. S. et al. Phylogenomics, origin, and diversification of anthozoans (phylum Cnidaria). Syst. Biol. 70, 635–647 (2021).

    Article  PubMed  Google Scholar 

  36. Morris, J. L. et al. The timescale of early land plant evolution. Proc. Natl Acad. Sci. USA 115, E2274–E2283 (2018).

    CAS  PubMed  PubMed Central  Google Scholar 

  37. Medema, M. H., de Rond, T. & Moore, B. S. Mining genomes to illuminate the specialized chemistry of life. Nat. Rev. Genet. 22, 553–571 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  38. Nützmann, H. -W., Huang, A. & Osbourn, A. Plant metabolic clusters—from genetics to genomics. New Phytol. 211, 771–789 (2016).

    Article  PubMed  PubMed Central  Google Scholar 

  39. De La Peña, R. & Sattely, E. S. Rerouting plant terpene biosynthesis enables momilactone pathway elucidation. Nat. Chem. Biol. 17, 205–212 (2021).

    Article  CAS  Google Scholar 

  40. Morris, L. A., Jaspars, M., Adamson, K., Woods, S. & Wallace, H. M. The capnellenes revisited: new structures and new biological activity. Tetrahedron 54, 12953–12958 (1998).

    Article  CAS  Google Scholar 

  41. Jean, Y.-H. et al. Capnellene, a natural marine compound derived from soft coral, attenuates chronic constriction injury-induced neuropathic pain in rats. Br. J. Pharmacol. 158, 713–725 (2009).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Ayanoglu, E., Gebreyesus, T., Beechan, C. M., Djerassi, C. & Kaisin, M. Terpenoids LXXV. Δ9(12)-Capnellene, a new sesquiterpene hydrocarbon from the soft coral Capnella imbricata. Tetrahedron Lett. 19, 1671–1674 (1978).

    Article  Google Scholar 

  43. DeLeo, D. M. et al. Gene expression profiling reveals deep-sea coral response to the Deepwater Horizon oil spill. Mol. Ecol. 27, 4066–4077 (2018).

    Article  CAS  PubMed  Google Scholar 

  44. Todaro, D. & Watson, G. M. Force-dependent discharge of nematocysts in the sea anemone Haliplanella luciae (Verrill). Biol. Open 1, 582–587 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. Woodside, A. B., Huang, Z. & Poulter, C. D. Trisammonium geranyl diphosphate. Org. Synth. 66, 211 (1988).

    Article  CAS  Google Scholar 

  46. Jo Davisson, V., Woodside, A. B. & Dale Poulter, C. D. Synthesis of allylic and homoallylic isoprenoid pyrophosphates. Methods Enzymol. 110, 130–144 (1985).

    Article  Google Scholar 

  47. Eddy, S. R. Accelerated profile HMM searches. PLoS Comput. Biol. 7, e1002195 (2011).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Grabherr, M. G. et al. Full-length transcriptome assembly from RNA-seq data without a reference genome. Nat. Biotechnol. 29, 644–652 (2011).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. Haas, B. J. et al. De novo transcript sequence reconstruction from RNA-seq using the Trinity platform for reference generation and analysis. Nat. Protoc. 8, 1494–1512 (2013).

    Article  CAS  PubMed  Google Scholar 

  50. Priyam, A. et al. Sequenceserver: a modern graphical user interface for custom BLAST databases. Mol. Biol. Evol. 36, 2922–2924 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  51. Lassmann, T., Frings, O. & Sonnhammer, E. L. L. Kalign2: high-performance multiple alignment of protein and nucleotide sequences allowing external features. Nucleic Acids Res. 37, 858–865 (2009).

    Article  CAS  PubMed  Google Scholar 

  52. Kumar, S., Stecher, G., Li, M., Knyaz, C. & Tamura, K. MEGA X: molecular evolutionary genetics analysis across computing platforms. Mol. Biol. Evol. 35, 1547–1549 (2018).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  53. Robert, X. & Gouet, P. Deciphering key features in protein structures with the new ENDscript server. Nucleic Acids Res. 42, W320–W324 (2014).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  54. Minh, B. Q. et al. IQ-TREE 2: new models and efficient methods for phylogenetic inference in the genomic era. Mol. Biol. Evol. 37, 1530–1534 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  55. Kabsch, W. XDS. Acta Crystallogr. D Biol. Crystallogr. 66, 125–132 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  56. Skubák, P. & Pannu, N. S. Automatic protein structure solution from weak X-ray data. Nat. Commun. 4, 2777 (2013).

    Article  PubMed  CAS  Google Scholar 

  57. Winn, M. D. et al. Overview of the CCP4 suite and current developments. Acta Crystallogr. D Biol. Crystallogr. 67, 235–242 (2011).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  58. Schneider, T. R. & Sheldrick, G. M. Substructure solution with SHELXD. Acta Crystallogr. D Biol. Crystallogr. 58, 1772–1779 (2002).

    Article  PubMed  CAS  Google Scholar 

  59. Cowtan, K. Recent developments in classical density modification. Acta Crystallogr. D Biol. Crystallogr. 66, 470–478 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  60. Skubák, P., Waterreus, W.-J. & Pannu, N. S. Multivariate phase combination improves automated crystallographic model building. Acta Crystallogr. D Biol. Crystallogr. 66, 783–788 (2010).

    Article  PubMed  CAS  Google Scholar 

  61. Cowtan, K. The Buccaneer software for automated model building. 1. Tracing protein chains. Acta Crystallogr. D Biol. Crystallogr. 62, 1002–1011 (2006).

    Article  PubMed  CAS  Google Scholar 

  62. Emsley, P., Lohkamp, B., Scott, W. G. & Cowtan, K. Features and development of Coot. Acta Crystallogr. D Biol. Crystallogr. 66, 486–501 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  63. Liebschner, D. et al. Macromolecular structure determination using X-rays, neutrons and electrons: recent developments in Phenix. Acta Crystallogr. D Biol. Crystallogr. 75, 861–877 (2019).

    Article  CAS  Google Scholar 

  64. Pont-Kingdon, G. A. et al. A coral mitochondrial mutS gene. Nature 375, 109–111 (1995).

    Article  CAS  PubMed  Google Scholar 

  65. France, S. C. & Hoover, L. L. DNA sequences of the mitochondrial COI gene have low levels of divergence among deep-sea octocorals (Cnidaria: Anthozoa). Hydrobiologia 471, 149–155 (2002).

    Article  Google Scholar 

  66. Sánchez, J. A., McFadden, C. S., France, S. C. & Lasker, H. R. Molecular phylogenetic analyses of shallow-water Caribbean octocorals. Mar. Biol. 142, 975–987 (2003).

    Article  Google Scholar 

  67. Bolger, A. M., Lohse, M. & Usadel, B. Trimmomatic: a flexible trimmer for Illumina sequence data. Bioinformatics 30, 2114–2120 (2014).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. Bankevich, A. et al. SPAdes: a new genome assembly algorithm and its applications to single-cell sequencing. J. Comp. Biol. 19, 455–477 (2012).

    Article  CAS  Google Scholar 

  69. Miller, I. J. et al. Autometa: automated extraction of microbial genomes from individual shotgun metagenomes. Nucleic Acids Res. 47, e57 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

We thank our University of California San Diego colleagues W. Fenical, L. Aluwihare and B. Duggan for critical feedback, access to GC–MS equipment and assistance with NMR measurements, respectively, C. Delbeek (California Academy of Sciences) for access to C. imbricata, J. Keasling and J. Blake-Hedges (University of California Berkeley) for assisting in genome sequencing, J. Bailey and the University of California San Diego Crystallography Facility for collecting the X-ray diffraction data used for phasing and J.P. Noel and G. Louie (Salk Institute for Biological Studies) for beamtime coordination. Use of the Stanford Synchrotron Radiation Lightsource is supported by the US Department of Energy, Office of Science, Office of Basic Energy Sciences under contract number DE-AC02-76SF00515, the Department of Energy Office of Biological and Environmental Research and the NIH and NIGMS (including P41GM103393). This work was supported by National Institutes of Health awards F32GM129960 to T.d.R. and R01GM085770 to B.S.M. and a Leopoldina postdoctoral fellowship (LPDS 2019-04) to I.B.

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Author notes

  1. Tristan de Rond

    Present address: School of Chemical Sciences, University of Auckland, Auckland, New Zealand

  2. Percival Yang-Ting Chen

    Present address: Morphic Therapeutics, Waltham, MA, USA

Authors and Affiliations

  1. Scripps Institution of Oceanography, University of California San Diego, La Jolla, CA, USA

    Immo Burkhardt, Tristan de Rond, Percival Yang-Ting Chen & Bradley S. Moore

  2. Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, CA, USA

    Bradley S. Moore

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Contributions

I.B., T.d.R. and B.S.M. conceived the project, designed the experiments, analyzed the data and wrote the paper with input from all authors. I.B. performed the protein expression and purification, enzymatic assays, product analyses and data analyses with help from T.d.R. who additionally performed the C. imbricata experiments. P.Y.-T.C. performed crystallography experiments and subsequent data analysis.

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Correspondence to Bradley S. Moore.

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Nature Chemical Biology thanks Thu-Thuy Dang and the other, anonymous, reviewer(s) for their contribution to the peer review of this work.

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Extended data

Extended Data Fig. 1 Radial depiction of the phylogenetic tree from Fig. 2.

The IDS clade is used as outgroup and bootstrap values for the branches are shown. The representative enzymes used for structure comparison in Fig. 3 are indicated by arrows.

Extended Data Fig. 2 Examples of octocoral derived terpenoid structures sharing a common terpene carbon backbone8.

Structures marked with an asterisk have been found as both enantiomers.

Extended Data Fig. 3 Genetic context of octocoral TCs.

Mapped transcripts (top), gene annotations (middle) and mapped long-reads (bottom) for the indicated regions are shown. a) Context of XsTC-1 from Xenia sp. b) Context of DgTC-1 from D. gigantea. c) Context of DgTC-2 from D. gigantea. All genes are coded on long eukaryotic contigs (see Supplementary Table 4) with continuous long read coverage between 60 and 130 (Oxford Nanopore for a, PacBio for b and c). While the expression of DgTC-1 and DgTC-2 is low, XsTC-1 is highly expressed. For gene IDs see Supplementary Tables 5-7. The co-occurrence of two different bases in the same position (marked by colors) results from the heterozygosity of D. gigantea and Xenia sp.

Extended Data Fig. 4 Octocoral gene clusters.

Genomic contigs from Xenia sp., Renilla muelleri and Trachythela sp. show the physical co-localization of TCs with genes coding for CYP and SHD enzymes. Genes on the Xenia scaffold that are marked in grey are either annotated as unknown proteins or show similarity to enzymes with non-biosynthetic functions. CYP = cytochrome P450 monooxygenase, IDS = isoprenyl diphosphate synthase, SDH = short-chain dehydrogenase, TC = terpene cyclase.

Extended Data Fig. 5 Putative biochemical pathway from 7 to oxidized Xenia diterpenoids.

A: Putative terpenoid cluster including Cytochrome P450 genes and short chain dehydrogenase genes additionally to the characterized terpene cyclase XsTC-1, which produces 7. B: Putative overview how different compounds isolated from Xenia spp. and closely related corals could be explained from 7 using CYP and SHD chemistry. The oxidative cleavage of the cyclobutene ring in 7 has been proposed in the literature28. The end points of these putative biochemical pathways all represent isolated molecules from different Xenia spp8. and could all result from CYP and SDH chemistry following the outlined scheme. Acylations and methylations are also observed in some compounds but could be the result of non-clustered specific or promiscuous enzymatic activity. CYP = cytochrome P450 monooxygenase, IDS = isoprenyl diphosphate synthase, SDH = short-chain dehydrogenase, TC = terpene cyclase, MT = methyl transferase, AT = acyl transferase.

Extended Data Fig. 6 Analysis of a dichloromethane extract of Capnella imbricata by GC-MS.

Signals for capnellene (11), capnellene-8β,10α-diol (12) and putative terpenoid compounds are labeled.

Supplementary information

Supplementary Information

Supplementary Figs. 1–21, Notes 1 and 2, Tables 1–11 and references 1–51.

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Burkhardt, I., de Rond, T., Chen, P.YT. et al. Ancient plant-like terpene biosynthesis in corals. Nat Chem Biol 18, 664–669 (2022). https://doi.org/10.1038/s41589-022-01026-2

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