25. Uchimara M, Bonfils C, Sandeaux R, Terawaki T, Amade P, Larroque C (1999) Caulerpenyne,
the major terpene extracted from the alga Caulerpa taxifolia, is an inhibitor of cytochrome P450
dependent activities. In: 11th international conference on cytochrome P450, Sendai
26. Marić P, Ahel M, Senta I, Terzić S, Mikac I, Žuljević A, Smital T (2017) Effect-directed analysis
reveals inhibition of zebrafish uptake transporter Oatp1d1 by caulerpenyne, a major secondary
metabolite from the invasive marine alga Caulerpa taxifolia. Chemosphere 174:643–654.
https://doi.org/10.1016/j.chemosphere.2017.02.007
27. Popovic M, Zaja R, Fent K, Smital T (2013) Molecular characterization of zebrafish Oatp1d1
(Slco1d1), a novel organic anion-transporting polypeptide. J Biol Chem 288:33894–33911.
https://doi.org/10.1074/jbc.M113.518506
28. Aguilar-Santos G (1970) Caulerpin, a new red pigment from green algae of the genus Caulerpa.
J Chem Soc C 842–843. https://doi.org/10.1039/J39700000842
29. Maiti BC, Thomson RH (1977) Caulerpin. In: Faulkner DJ, Fenical WH (eds) Marine natural
products chemistry. Springer, Boston, pp 159–163
30. Cavalcante-Silva L, de Carvalho Correia A, Barbosa-Filho J, da Silva B, de Oliveira Santos B,
de Lira D, Sousa J, de Miranda G, de Andrade Cavalcante F, Alexandre-Moreira M (2013)
Spasmolytic effect of Caulerpine involves blockade of Ca
2+ influx on guinea pig ileum. Mar
Drugs 11:1553–1564. https://doi.org/10.3390/md11051553
31. Kamal C, Sethuraman MG (2012) Caulerpin – a bis-indole alkaloid as a green inhibitor for the
corrosion of mild steel in 1 M HCl solution from the marine alga Caulerpa racemosa. Ind Eng
Chem Res 51:10399–10407. https://doi.org/10.1021/ie3010379
32. Macedo NRPV, Ribeiro MS, Villaça RC, Ferreira W, Pinto AM, Teixeira VL, Cirne-Santos C,
Paixão ICNP, Giongo V (2012) Caulerpin as a potential antiviral drug against herpes simplex
virus type 1. Rev Bras 22:861–867. https://doi.org/10.1590/S0102-695X2012005000072
33. De Souza ÉT, Pereira de Lira D, Cavalcanti de Queiroz A, Costa da Silva DJ, Bezerra de Aquino
A, Campessato Mella E, Prates Lorenzo V, De Miranda GE, De Araújo-Júnior JX, De Oliveira
Chaves MC, Barbosa-Filho JM, Filgueiras de Athayde-Filho P, De Oliveira Santos BV,
Alexandre-Moreira MS (2009) The antinociceptive and anti-inflammatory activities of
caulerpin, a bisindole alkaloid isolated from seaweeds of the genus Caulerpa. Mar Drugs
7:689–704. https://doi.org/10.3390/md7040689
34. Alarif WM, Abou-Elnaga ZS, Ayyad S-EN, Al-lihaibi SS (2010) Insecticidal metabolites from
the green alga Caulerpa racemosa. Clean Soil Air Water 38:548–557. https://doi.org/10.1002/
clen.201000033
35. Raub MF, Cardellina JH, Schwede JG (1987) The green algal pigment caulerpin as a plant growth
regulator. Phytochemistry 26:619–620. https://doi.org/10.1016/S0031-9422(00)84752-4
36. Liu Y, Morgan JB, Coothankandaswamy V, Liu R, Jekabsons MB, Mahdi F, Nagle DG, Zhou YD (2009) The Caulerpa pigment caulerpin inhibits HIF-1 activation and mitochondrial respiration. J Nat Prod 72:2104–2109. https://doi.org/10.1021/np9005794
37. Ferramosca A, Conte A, Guerra F, Felline S, Rimoli MG, Mollo E, Zara V, Terlizzi A (2016)
Metabolites from invasive pests inhibit mitochondrial complex II: a potential strategy for the
treatment of human ovarian carcinoma? Biochem Biophys Res Commun 473:1133–1138.
https://doi.org/10.1016/j.bbrc.2016.04.028
38. Mao S-C, Guo Y-W, Shen X (2006) Two novel aromatic valerenane-type sesquiterpenes from
the Chinese green alga Caulerpa taxifolia. Bioorg Med Chem Lett 16:2947–2950. https://doi.
org/10.1016/j.bmcl.2006.02.074
39. Vottero E, Balgi A, Woods K, Tugendreich S, Melese T, Andersen RJ, Mauk AG, Roberge M
(2006) Inhibitors of human indoleamine 2,3-dioxygenase identified with a target-based screen
in yeast. Biotechnol J 1:282–288. https://doi.org/10.1002/biot.200600001
40. Schröder HC, Badria FA, Ayyad SN, Batel R, Wiens M, Hassanein HMA, Kurelec B, Müller
WEG (1998) Inhibitory effects of extracts from the marine alga Caulerpa taxifolia and of toxin
from Caulerpa racemosa on multixenobiotic resistance in the marine sponge Geodia cydonium.
Environ Toxicol Pharmacol 5:119–126. https://doi.org/10.1016/S1382-6689(97)10067-9
6 Molecular Interactions as Drivers of Changes in Marine Ecosystems
131
the major terpene extracted from the alga Caulerpa taxifolia, is an inhibitor of cytochrome P450
dependent activities. In: 11th international conference on cytochrome P450, Sendai
26. Marić P, Ahel M, Senta I, Terzić S, Mikac I, Žuljević A, Smital T (2017) Effect-directed analysis
reveals inhibition of zebrafish uptake transporter Oatp1d1 by caulerpenyne, a major secondary
metabolite from the invasive marine alga Caulerpa taxifolia. Chemosphere 174:643–654.
https://doi.org/10.1016/j.chemosphere.2017.02.007
27. Popovic M, Zaja R, Fent K, Smital T (2013) Molecular characterization of zebrafish Oatp1d1
(Slco1d1), a novel organic anion-transporting polypeptide. J Biol Chem 288:33894–33911.
https://doi.org/10.1074/jbc.M113.518506
28. Aguilar-Santos G (1970) Caulerpin, a new red pigment from green algae of the genus Caulerpa.
J Chem Soc C 842–843. https://doi.org/10.1039/J39700000842
29. Maiti BC, Thomson RH (1977) Caulerpin. In: Faulkner DJ, Fenical WH (eds) Marine natural
products chemistry. Springer, Boston, pp 159–163
30. Cavalcante-Silva L, de Carvalho Correia A, Barbosa-Filho J, da Silva B, de Oliveira Santos B,
de Lira D, Sousa J, de Miranda G, de Andrade Cavalcante F, Alexandre-Moreira M (2013)
Spasmolytic effect of Caulerpine involves blockade of Ca
2+ influx on guinea pig ileum. Mar
Drugs 11:1553–1564. https://doi.org/10.3390/md11051553
31. Kamal C, Sethuraman MG (2012) Caulerpin – a bis-indole alkaloid as a green inhibitor for the
corrosion of mild steel in 1 M HCl solution from the marine alga Caulerpa racemosa. Ind Eng
Chem Res 51:10399–10407. https://doi.org/10.1021/ie3010379
32. Macedo NRPV, Ribeiro MS, Villaça RC, Ferreira W, Pinto AM, Teixeira VL, Cirne-Santos C,
Paixão ICNP, Giongo V (2012) Caulerpin as a potential antiviral drug against herpes simplex
virus type 1. Rev Bras 22:861–867. https://doi.org/10.1590/S0102-695X2012005000072
33. De Souza ÉT, Pereira de Lira D, Cavalcanti de Queiroz A, Costa da Silva DJ, Bezerra de Aquino
A, Campessato Mella E, Prates Lorenzo V, De Miranda GE, De Araújo-Júnior JX, De Oliveira
Chaves MC, Barbosa-Filho JM, Filgueiras de Athayde-Filho P, De Oliveira Santos BV,
Alexandre-Moreira MS (2009) The antinociceptive and anti-inflammatory activities of
caulerpin, a bisindole alkaloid isolated from seaweeds of the genus Caulerpa. Mar Drugs
7:689–704. https://doi.org/10.3390/md7040689
34. Alarif WM, Abou-Elnaga ZS, Ayyad S-EN, Al-lihaibi SS (2010) Insecticidal metabolites from
the green alga Caulerpa racemosa. Clean Soil Air Water 38:548–557. https://doi.org/10.1002/
clen.201000033
35. Raub MF, Cardellina JH, Schwede JG (1987) The green algal pigment caulerpin as a plant growth
regulator. Phytochemistry 26:619–620. https://doi.org/10.1016/S0031-9422(00)84752-4
36. Liu Y, Morgan JB, Coothankandaswamy V, Liu R, Jekabsons MB, Mahdi F, Nagle DG, Zhou YD (2009) The Caulerpa pigment caulerpin inhibits HIF-1 activation and mitochondrial respiration. J Nat Prod 72:2104–2109. https://doi.org/10.1021/np9005794
37. Ferramosca A, Conte A, Guerra F, Felline S, Rimoli MG, Mollo E, Zara V, Terlizzi A (2016)
Metabolites from invasive pests inhibit mitochondrial complex II: a potential strategy for the
treatment of human ovarian carcinoma? Biochem Biophys Res Commun 473:1133–1138.
https://doi.org/10.1016/j.bbrc.2016.04.028
38. Mao S-C, Guo Y-W, Shen X (2006) Two novel aromatic valerenane-type sesquiterpenes from
the Chinese green alga Caulerpa taxifolia. Bioorg Med Chem Lett 16:2947–2950. https://doi.
org/10.1016/j.bmcl.2006.02.074
39. Vottero E, Balgi A, Woods K, Tugendreich S, Melese T, Andersen RJ, Mauk AG, Roberge M
(2006) Inhibitors of human indoleamine 2,3-dioxygenase identified with a target-based screen
in yeast. Biotechnol J 1:282–288. https://doi.org/10.1002/biot.200600001
40. Schröder HC, Badria FA, Ayyad SN, Batel R, Wiens M, Hassanein HMA, Kurelec B, Müller
WEG (1998) Inhibitory effects of extracts from the marine alga Caulerpa taxifolia and of toxin
from Caulerpa racemosa on multixenobiotic resistance in the marine sponge Geodia cydonium.
Environ Toxicol Pharmacol 5:119–126. https://doi.org/10.1016/S1382-6689(97)10067-9
6 Molecular Interactions as Drivers of Changes in Marine Ecosystems
131