Abstract
Natural products provide an important source of new therapeutic drugs and biochemical tools. In the last decades researchers of natural products chemistry focused their research in a wide variety of bioactive compounds from marine species. Marine sponges have been considered as a very fertile field for the discovery of bioactive natural chemical substances with respect to the diversity of their primary and secondary chemical components and metabolites. Triterpenoids are the most abundant secondary metabolite present in marine sponges. A large number of triterpenoids are known to exhibit cytotoxicity against a variety of tumor cells as well as anticancer efficacy in preclinical animal models. Therefore, triterpenoids from marine sponges leads to be used in the pharmaceutical industry as new chemical classes of anticancer agents.
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References
Da Frota Jr MLC, da Silva RB, Mothes B, Teresinha Henriques A, Fonseca Moreira JC (2012) Current status on natural products with antitumor activity from Brazilian marine sponges. Curr Pharm Biotechnol 13:235–244
Perdicaris S, Vlachogianni T, Valavanidis A (2013) Bioactive natural substances from marine sponges: new developments and prospects for future pharmaceuticals. Nat Prod Chem Res 1:3
Valeriote FA, Tenney K, Medla J, Pietraszkiewicz H, Edelstein M, Johnson TA, Amagata T, Crews P (2012) Discovery and development of anticancer agents from marine sponges: perspectives based on a chemistry-experimental therapeutics collaborative program. J Exp Ther Oncol 10:119–134
Petronelli A, Pannitteri G, Testa U (2009) Triterpenoids as new promising anticancer drugs. Anticancer Drugs 20:880–892
Connolly JD, Hill RA (1997) Triterpenoids. Nat Prod Rep 14:661–679
Connolly JD, Hill RA (2002) Triterpenoids. Nat Prod Rep 19:494–513
Ravi BN, Wells RJ (1981) Malabaricane triterpenes from a fijian collection of the sponge Jaspis stellifera. J Org Chem 46:1998–2001
Rao ZG, Deng SZ, Wu HM, Jiang SK (1997) Rhabdastrellic acid-A, a novel triterpenoid from the marine sponge Rhabdastrella globostellata. J Nat Prod 60:1163–1164
Bishayee A, Ahmed S, Brankov N, Perloff M (2011) Triterpenoids as potential agents for the chemoprevention and therapy of breast cancer. Front Biosci 16:980–996
Drag M, Surowiak P, Drag-Zalesinska M, Dietel M, Lage H, Oleksyszyn J (2009) Comparision of the cytotoxic effects of birch bark extract, betulin and betulinic acid towards human gastric carcinoma and pancreatic carcinoma drug-sensitive and drug-resistant cell lines. Molecule 14:1639–1651
Liby KT, Yore MM, Sporn MB (2007) Triterpenoids and rexinoids as multifunctional agents for the prevention and treatment of cancer. Nat Rev Cancer 7:357–369
Hill RA, Connolly, JD (2012) Triterpenoids. Nat Prod Rep 29:780–818
Ebada SS, Lin WH, Proksch P (2010) Bioactive sesterterpenes and triterpenes from marine sponges: occurrence and pharmacological significance. Mar Drugs 8:313–346
Tang SA, Deng ZW, Li J, Fu HZ, Pei YH, Zhang S, Lin, WH (2005) A new isomalabaricane triterpenoid from sponge Jaspis sp. Chin Chem Lett 16:353–355
McCormick JL, McKee TC, Cardellina JH, Leid M, Boyd MR (1996) Cytotoxic triterpenes from a marine sponge, Stelletta sp. J Nat Prod 59:1047–1050
Ryu G, Matsunaga S, Fusetani N (1996) Globostellatic acids A-D, new cytotoxic isomalabaricane triterpenes from the marine sponge Stelletta globostellata. J Nat Prod 59:512–514
Lin HW, Wang ZL, Wu JH, Shi N, Zhang HJ, Chen WS, Morris-Natschke SL, Lin AS (2007) Stellettins L and M, cytotoxic isomalabaricane-type triterpenes, and sterols from the marine sponge Stelletta tenuis. J Nat Prod 70:1114–1117
Lv F, Deng ZW, Li J, Fu HZ, Soest RWM, Proksch P, Lin WH (2004) Isomalabaricane-type compounds from the marine sponge rhabdastrella aff. distincta. J Nat Prod 67:2033–2036
Su JY, Meng YH, Zen LM (1994) Stelletttin A, a new triterpenoid pigment from the marine sponge Stelletta tenuzs. J Nat Prod 57:1450–1451
Essack M, Bajic VB, Archer JAC (2011) Recently confirmed apoptosis-inducing lead compounds isolated from marine sponge of potential relevance in cancer treatment. Mar Drugs 9:1580–1606
Tasdemir D, Mangalindan GC, Concepcion GP, Verbitski SM, Rabindran S, Miranda M, Greenstein M, Hooper JNA, Harper MK, Ireland CM (2002) Bioactive isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata. J Nat Prod 65:210–214
Clement JA, Li M, Hecht, SM, Kingston DG (2006) I Bioactive isomalabaricane triterpenoids from Rhabdastrella globostellata that stabilize the binding of DNA polymerase β to DNA. J Nat Prod 69:373–376
Tsuda M, Ishibashi M, Agemi K, Sasaki T, Kobayashi J (1991) Stelliferins A–F, new antineoplastic isomalabaricane triterpenes from the Okinawan marine sponge Jaspis stellifera. Tetrahedron 47:2181–2194
Meragelman KM, McKee TC, Boyd MR (2001) New cytotoxic isomalabaricane triterpenes from the sponge Jaspis Species. J Nat Prod 64:389–392
Liu WK, Ho JCK, Che CT (2005) Apoptotic activity of isomalabaricane triterpenes on human promyelocytic leukemia HL60 cells. Cancer Lett 230:102–110
Antonov AS, Kalinovsky AI, Stonik VA, Afiyatullov SS, Aminin DL, Dmitrenok PS, Mollo E, Cimino G (2007) Isolation and structures of erylosides from the Carribean sponge Erylus formosus. J Nat Prod 70:169–178
Rudi A, Kashman Y (1994) Sodwanones A-F, new triterpenoids from the marine sponge Axinella weltneri. J Nat Prod 57:1416–1423
Rudi A, Goldberg I, Stein Z, Kashman Y (1995) Sodwanones G, H, I, new cytotoxic triterpenes from a marine sponge. J Nat Prod 58:1702–1712
Rudi A, Aknin M, Gaydou EM, Kashman Y (1997) Sodwanones K, L, M; new triterpenes from the marine sponge Axinella weltneri. J Nat Prod 60:700–703
Bon CF, Berrue F, Thomas OP, Reyes F, Amade P (2005) Sodwanone S, a triterpene from the marine sponge Axinella weltneri. J Nat Prod 68:1284–1287
Dai JQ, Fishback JA, Zhou YD, Nagle DG (2006) Sodwanone and yardenone triterpenes from a South African species of the marine sponge Axinella inhibit hypoxia-inducible factor-1 (HIF-1) activation in both breast and prostate tumor cells. J Nat Prod 69:1715–1720
Cimino G, Crispino A, Madaio A, Trivellone E (1993a) Raspacionin B, a further triterpenoid from the mediterranean sponge Raspaciona aculeata. J Nat Prod 56:534–538
Cimino G, Epifanio RDA, Madaio A, Puliti R, Trivellone E (1993b) Absolute stereochemistry of raspacionin, the main triterpenoid from the marine sponge Raspaciona aculeata. J Nat Prod 56:1622–1626
Cimino G, Madaio A, Trivellone E (1994) Minor triterpenoids from the mediterranean sponge, Raspaciona aculeata. J Nat Prod 57:784–790
Jain S, Abraham I, Carvalho P, Kuang YH, Shaala L, Youssef DTA, Avery MA, Chen ZS, Sayed KE (2009) Sipholane triterpenoids: chemistry, reversal of ABCB1/P-glycoprotein-mediated multidrug resistance, and pharmacophore modeling. J Nat Prod 72:1291–1298
Jain S, Laphookhieo S, Shi Z, Fu LW, Akiyama S, Chen ZS, Youssef DTA, Soest RWM, Sayed KE (2007) Reversal of P-glycoprotein-mediated multidrug resistance by sipholane triterpenoids. J Nat Prod 70:928–931
Shi Z, Jain S, Kim IW, Peng XX, Abraham I, Youssef DTA, Fu LW, Sayed KE, Ambudkar SV, Chen ZS (2007) Sipholenol A, a marine-derived sipholane triterpene, potently reverses P-glycoprotein (ABCB1)-mediated multidrug resistance in cancer cells. Cancer Sci 98:1373–380
Abraham I, Jain S, Wu CP, Khanfar M, Kuang YH, Dai CL, Shi Z, Chen X, Fu LW, Ambudkar SV, Sayed KE, Chen ZS (2010) Marine sponge-derived sipholane triterpenoids reverse P-glycoprotein (ABCB1)-mediated multidrug resistance in cancer cells. Biochem Pharmacol 80:1497–1506
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Li, YX., Kim, SK. (2015). Triterpenoids as Anticancer Drugs from Marine Sponges. In: Kim, SK. (eds) Handbook of Anticancer Drugs from Marine Origin. Springer, Cham. https://doi.org/10.1007/978-3-319-07145-9_2
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DOI: https://doi.org/10.1007/978-3-319-07145-9_2
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