and defensive weapons in aquatic environments. Proc Natl Acad Sci 114:3451–3456. https://
doi.org/10.1073/pnas.1614655114
8. Huey RB, Gilchrist GW, Hendry AP (2005) Using invasive species to study evolution: case
studies with Drosophila and Salmon. In: Sax DF, Stachowicz JJ, Gaines SD (eds) Species
invasions: insights into ecology, evolution and biogeography. Sinauer Associates, Inc, Sunderland, pp 139–164. 01375
9. Mollo E, Cimino G, Ghiselin MT (2015) Alien biomolecules: a new challenge for natural
product chemists. Biol Invasions 17:941–950. https://doi.org/10.1007/s10530-014-0835-6
10. Mollo E, Gavagnin M, Carbone M, Castelluccio F, Pozone F, Roussis V, Templado J, Ghiselin
MT, Cimino G (2008) Factors promoting marine invasions: a chemoecological approach. Proc
Natl Acad Sci U S A 105:4582–4586. https://doi.org/10.1073/pnas.0709355105
11. Boudouresque CF, Verlaque M (2002) Biological pollution in the Mediterranean Sea: invasive
versus introduced macrophytes. Mar Pollut Bull 44:32–38. https://doi.org/10.1016/S0025326X(01)00150-3
12. Máximo P, Ferreira L, Branco P, Lima P, Lourenço A (2018) Secondary metabolites and
biological activity of invasive macroalgae of Southern Europe. Mar Drugs 16:265. https://doi.
org/10.3390/md16080265
13. Raniello R, Mollo E, Lorenti M, Gavagnin M, Buia MC (2007) Phytotoxic activity of
caulerpenyne from the Mediterranean invasive variety of Caulerpa racemosa: a potential
allelochemical. Biol Invasions 9:361–368. https://doi.org/10.1007/s10530-006-9044-2
14. Ruíz JM, Boudouresque CF, Enríquez S (2009) Mediterranean seagrasses. Bot Mar 52. https://
doi.org/10.1515/BOT.2009.058
15. Amico V, Oriente G, Piattelli M, Tringali C, Fattorusso E, Magno S, Mayol L (1978)
Caulerpenyne, an unusual sequiterpenoid from the green alga Caulerpa prolifera. Tetrahedron
Lett 19:3593–3596. https://doi.org/10.1016/S0040-4039(01)95003-8
16. Sfecci E, Le Quemener C, Lacour T, Massi L, Amade P, Audo G, Mehiri M (2017)
Caulerpenyne from Caulerpa taxifolia: a comparative study between CPC and classical
chromatographic techniques. Phytochem Lett 20:406–409. https://doi.org/10.1016/j.
phytol.2017.01.014
17. Brunelli M, Garcia-Gil M, Mozzachiodi R, Scuri MRR, Traina G, Zaccardi ML (2000)
Neurotoxic effects of caulerpenyne. Prog Neuro-Psychopharmacology Biol Psychiatry.
https://doi.org/10.1016/S0278-5846(00)00112-3
18. Commeiras L, Bourdron J, Douillard S, Barbier P, Vanthuyne N, Peyrot V, Parrain J-L (2006)
Total synthesis of terpenoids isolated from caulerpale algae and their inhibition of tubulin
assembly. Synthesis-Stuttgart 2006:166–181. https://doi.org/10.1055/s-2005-921760
19. Cavas L, Baskin Y, Yurdakoc K, Olgun N (2006) Antiproliferative and newly attributed
apoptotic activities from an invasive marine alga: Caulerpa racemosa var. cylindracea. J Exp
Mar Biol Ecol 339:111–119. https://doi.org/10.1016/j.jembe.2006.07.019
20. Barbier P, Guise S, Huitorel P, Amade P, Pesando D, Briand C, Peyrot V (2001) Caulerpenyne
from Caulerpa taxifolia has an antiproliferative activity on tumor cell line SK-N-SH and
modifies the microtubule network. Life Sci 70:415–429. https://doi.org/10.1016/S0024-3205
(01)01396-0
21. Cengiz S, Cavas L, Yurdakoc K (2010) Alpha-amylase inhibition kinetics by caulerpenyne.
Mediterr Mar Sci 11:93–103. https://doi.org/10.12681/mms.93
22. Cengiz S, Cavas L, Yurdakoc K, Pohnert G (2011) The sesquiterpene caulerpenyne from
Caulerpa spp. is a lipoxygenase inhibitor. Mar Biotechnol. https://doi.org/10.1007/s10126010-9303-1
23. Richter P, Schubert G, Schaible AM, Cavas L, Werz O, Pohnert G (2014) Caulerpenyne and
related bis-enol esters are novel-type inhibitors of human 5-lipoxygenase. Chem Med Chem 9.
https://doi.org/10.1002/cmdc.201402065
24. Cengiz S, Cavas L, Yurdakoc K, Aksu S (2012) Inhibition of xanthine oxidase by Caulerpenyne
from Caulerpa prolifera. Turk J Biochem 37:445–451. https://doi.org/10.5505/tjb.2012.98698
130
F. Defranoux and E. Mollo
doi.org/10.1073/pnas.1614655114
8. Huey RB, Gilchrist GW, Hendry AP (2005) Using invasive species to study evolution: case
studies with Drosophila and Salmon. In: Sax DF, Stachowicz JJ, Gaines SD (eds) Species
invasions: insights into ecology, evolution and biogeography. Sinauer Associates, Inc, Sunderland, pp 139–164. 01375
9. Mollo E, Cimino G, Ghiselin MT (2015) Alien biomolecules: a new challenge for natural
product chemists. Biol Invasions 17:941–950. https://doi.org/10.1007/s10530-014-0835-6
10. Mollo E, Gavagnin M, Carbone M, Castelluccio F, Pozone F, Roussis V, Templado J, Ghiselin
MT, Cimino G (2008) Factors promoting marine invasions: a chemoecological approach. Proc
Natl Acad Sci U S A 105:4582–4586. https://doi.org/10.1073/pnas.0709355105
11. Boudouresque CF, Verlaque M (2002) Biological pollution in the Mediterranean Sea: invasive
versus introduced macrophytes. Mar Pollut Bull 44:32–38. https://doi.org/10.1016/S0025326X(01)00150-3
12. Máximo P, Ferreira L, Branco P, Lima P, Lourenço A (2018) Secondary metabolites and
biological activity of invasive macroalgae of Southern Europe. Mar Drugs 16:265. https://doi.
org/10.3390/md16080265
13. Raniello R, Mollo E, Lorenti M, Gavagnin M, Buia MC (2007) Phytotoxic activity of
caulerpenyne from the Mediterranean invasive variety of Caulerpa racemosa: a potential
allelochemical. Biol Invasions 9:361–368. https://doi.org/10.1007/s10530-006-9044-2
14. Ruíz JM, Boudouresque CF, Enríquez S (2009) Mediterranean seagrasses. Bot Mar 52. https://
doi.org/10.1515/BOT.2009.058
15. Amico V, Oriente G, Piattelli M, Tringali C, Fattorusso E, Magno S, Mayol L (1978)
Caulerpenyne, an unusual sequiterpenoid from the green alga Caulerpa prolifera. Tetrahedron
Lett 19:3593–3596. https://doi.org/10.1016/S0040-4039(01)95003-8
16. Sfecci E, Le Quemener C, Lacour T, Massi L, Amade P, Audo G, Mehiri M (2017)
Caulerpenyne from Caulerpa taxifolia: a comparative study between CPC and classical
chromatographic techniques. Phytochem Lett 20:406–409. https://doi.org/10.1016/j.
phytol.2017.01.014
17. Brunelli M, Garcia-Gil M, Mozzachiodi R, Scuri MRR, Traina G, Zaccardi ML (2000)
Neurotoxic effects of caulerpenyne. Prog Neuro-Psychopharmacology Biol Psychiatry.
https://doi.org/10.1016/S0278-5846(00)00112-3
18. Commeiras L, Bourdron J, Douillard S, Barbier P, Vanthuyne N, Peyrot V, Parrain J-L (2006)
Total synthesis of terpenoids isolated from caulerpale algae and their inhibition of tubulin
assembly. Synthesis-Stuttgart 2006:166–181. https://doi.org/10.1055/s-2005-921760
19. Cavas L, Baskin Y, Yurdakoc K, Olgun N (2006) Antiproliferative and newly attributed
apoptotic activities from an invasive marine alga: Caulerpa racemosa var. cylindracea. J Exp
Mar Biol Ecol 339:111–119. https://doi.org/10.1016/j.jembe.2006.07.019
20. Barbier P, Guise S, Huitorel P, Amade P, Pesando D, Briand C, Peyrot V (2001) Caulerpenyne
from Caulerpa taxifolia has an antiproliferative activity on tumor cell line SK-N-SH and
modifies the microtubule network. Life Sci 70:415–429. https://doi.org/10.1016/S0024-3205
(01)01396-0
21. Cengiz S, Cavas L, Yurdakoc K (2010) Alpha-amylase inhibition kinetics by caulerpenyne.
Mediterr Mar Sci 11:93–103. https://doi.org/10.12681/mms.93
22. Cengiz S, Cavas L, Yurdakoc K, Pohnert G (2011) The sesquiterpene caulerpenyne from
Caulerpa spp. is a lipoxygenase inhibitor. Mar Biotechnol. https://doi.org/10.1007/s10126010-9303-1
23. Richter P, Schubert G, Schaible AM, Cavas L, Werz O, Pohnert G (2014) Caulerpenyne and
related bis-enol esters are novel-type inhibitors of human 5-lipoxygenase. Chem Med Chem 9.
https://doi.org/10.1002/cmdc.201402065
24. Cengiz S, Cavas L, Yurdakoc K, Aksu S (2012) Inhibition of xanthine oxidase by Caulerpenyne
from Caulerpa prolifera. Turk J Biochem 37:445–451. https://doi.org/10.5505/tjb.2012.98698
130
F. Defranoux and E. Mollo