Sesquiterpene quinones from a marine sponge Hippospongia sp. that inhibit maturation of starfish oocytes and induce cell cycle arrest with HepG2 cells

Pharmaceutical Biology

Volumn 44, Issue 7, 2006, Pages 522-527

  Liu, Hongwei ^a,c   Wang, Guanghui ^b   Namikoshi, Michio ^c   Kobayashi, Hisayoshi ^d   Yao, Xinsheng ^b   Cai, Guoping ^a  

^a TSINGHUA UNIVERSITY   (China)

^b Shenzhen University Town   (China)

^c TOKYO UNIVERSITY OF MARINE SCIENCE AND TECHNOLOGY   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

Cell cycle arrest; Cytotoxicity; Marine sponge; Sesquiterpene quinone

Indexed keywords

5 ILIMAQUINONE; 5 ISOSPONGIAQUINONE; ILIMAQUINONE; QUINONE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOASSAY; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL CYCLE ARREST; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL PROLIFERATION; CELL STRAIN HEPG2; CELL STRAIN HL 60; CELL STRAIN MCF 7; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG ISOLATION; DRUG SCREENING; FLOW CYTOMETRY; HELA CELL; HUMAN; HUMAN CELL; MEIOSIS; METABOLITE; NONHUMAN; OOCYTE MATURATION; PALAU; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STARFISH; STRUCTURE ACTIVITY RELATION;

ASTEROIDEA; HIPPOSPONGIA;

EID: 33750042567     PISSN: 13880209     EISSN: 17445116     Source Type: Journal    
DOI: 10.1080/13880200600883056     Document Type: Article

References (34)

1. Aoki S, Kong DX, Matsui K, Rachmat R, Kobayashi M (2004): Sesquiterpene aminoquinones, from a marine sponge, induce erythroid differentiation in human chronic myelogenous leukemia, K562 cells. Chem Pharm Bull 52: 935-937.
2. Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2004): Marine natural products. Nat Prod Rep 21: 1-49.
3. Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR (2005): Marine natural products. Nat Prod Rep 22: 15-61.
4. Capon JR, MacLeod JK (1987): Revision of the absolute stereochemistry of ilimaquinone. J Org Chem 52: 5059-5060.
5. Capon, RJ (1995): In: Atta-ur Rahman, ed., Studies in Natural Products Chemistry, Structure and Chemistry (Part C), Vol. 15. Chapter 6 Marine sesquiterpene quinines and antimicrobial activity of amphibian venoms. Elsevier, Amsterdam, pp. 289-326.
6. Duckworth AR (1999): The discovery and development of marine compounds with pharmaceutical potential. J Biotech 70: 15-25.
7. Evans TP, Cornell L, Peterson RW, Faulkner DJ (1994): Isolation and synthesis of a glycine derivative of ilimaquinone from Fasciospongia sp. Nat Prod Lett 4: 287-291.
8. Goclik E, Koenig GM, Wright AD, Kaminsky R (2000): Pelorol from the tropical marine sponge. Dactylospongia elegans. J Nat Prod 63: 1150-1152.
9. Hirsch S, Rudi A, Kashman Y, Loya Y (1991): New avarone and avarol derivatives from the marine sponge Dysidea cinerea. J Nat Prod 54: 92-96.
10. Kondracki ML, Guyot M (1989): Biologically active quinone and hydroquinone sesquiterpenoids from the sponge Smenospongia sp. Tetrahedron 45: 1995-2004.
11. Kushlan DM, Faukner DJ, Parkanyi L, Clardy J (1989): Metabolites of the Palauan sponge Dactylospongia sp. Tetrahedron 45: 3307-3312.
12. Kwak JH, Schmitz FJ, Kelly M (2000): Sesquiterpene quinols/quinines from the Micronesian sponge Petrosaspongia metachromia. J Nat Prod 63: 1153-1156.
13. Liu HW, Namikoshi M, Meguro S, Nagai H, Kobayashi H, Yao XS (2004): Isolation and characterization of polybrominated diphenyl ethers as inhibitors of microtubule assembly from the marine sponge Phyllospongia dendyi collected at Palau. J Nat Prod 67: 472-474.
14. Liu HW., Namikoshi M, Akano K, Kobayashi H, Nagai N, Yao X. S (2005): Seven new meroditerpenoids, from the marine sponge Strongylophora strongylata, that inhibited the maturation of starfish oocytes. J Asian Nat Prod Res 7: 661-670.
15. Loya S, Hizi A (1993): The interaction of illimaquinone, a selective inhibitor of the RNase H activity, with the reverse transcriptases of human immunodeficiency and murine leukemia retroviruses. J Biol Chem 268: 9323-9328.
16. Loya S, Tal R, Kashman Y, Hizi A (1990): Illimaquinone, a selective inhibitor of the RNase H activity of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother 34: 2009-2012.
17. Luibrand RT, Erdman TR, Vollmer JJ, Scheuer PJ, Finer J, Clardy J (1979): Ilimaquinone, a sesquiterpenoid quinone from a marine sponge. Tetrahedron 35: 609-612.
18. Marinlit A (2001): A marine literature database produced and maintained by the Department of Chemistry, University of Canterbury, New Zealand. http://www.Chem.Canterbury.ac.nz/marinlit.
19. McConnell OJ, Longley R, Gunasekera M (1992): Isometachromin, a new cytotoxic sesquiterpenoid from a deep water sponge of the family Spongiidae. Experientia 48: 891-892.
20. Mitome H, Nagasawa T, Miyaoka H, Yamada Y, Soest RWM (2001): Dactyloquinones A and B, novel sesquterpenoid quinines from the Okinawa marine sponge, Dactylospongia elegans. J Nat Prod 64: 1506-1508.
21. Mitome H, Nagasawa T, Miyaoka H, Yamada Y, Soest RWM (2002): Dactyloquinones C, D and E novel sesquterpenoid quinines, from the Okinawa marine sponge, Dactylospongia elegans. Tetrahedron 58: 693-1696.
22. Munro MHG, Blunt JW, Dumdei EJ, Hickford SJH, Lill RE, Li S, Battershill CN, Toraya T, Maoka T, Tsuji H, Kobayashi M (1995): Purification and structural determination of an inhibitor of starfish oocyte maturation from a Bacillus species. Appl Environ Microbiol 61: 1799-1804.
23. Nakamura H, Deng S, Kobayashi J, Ohizumi Y, Hirata Y (1986): Dictyoceratin-A and -B, novel antimicrobial terpenoids from the Okinawan marine sponge Hippospongia sp. Tetrahedron 42: 4197-4201.
24. Nambiar MP, Wu HC (1995): Ilimaquinone inhibits the cytotoxicities of ricin, diphtheria toxin, and other protein toxins in Vero cell. Exp Cell Res 219: 671-678.
25. Pous C, Chabin K, Drechou A, Barbot L, Phung-Koskas T, Settegrana C, Bourguet-Kondracki M, Maurice M, Cassio D, Guyot M, Durand G (1998): Functional specialization of stable and dynamic microtubules in protein traffic in XWIF-B cells. J Cell Biol 142: 153-165.
26. Rangel HR, Dagger F, Compagnone RS (1997): Antiproliferative effect of illimaquinone on Leishmania mexicana. Cell Biol Int 21: 337-339.
27. Rodriguez J, Quinoa E, Riguera R, Peters BM, Abrell LM, Crews P (1992): The structures and stereochemistry of cytotoxic sesquiterpene quinines from Dactylospongia elegans. Tetrahedron 32: 6667-6680.
28. Salmoun M, Devijver C, Daloze D, Braekman JC, Gomez R, Kluijver M, Van Soest RWM (2000): New sesquiterpene/quinines from two sponges of the genus Htrtios. J Nat Prod 63: 452-456.
29. Shen YC, Hsieh PW (1997): New sesquiterpene hydroquinones from a Taiwanese marine sponge. Polyfibrospongia australis. J Nat Prod 60: 93-97.
30. Takizawa PA, Yucel JK, Veit B, Faulkner DJ, Deerinck T, Soto G, Ellisman M, Malhotra V (1993): Complete vesiculation of golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone. Cell 73: 1079-1090.
31. Talpir R, Rudi A, Kashman Y, Loya Y, Hizi A (1994): Three new sesquiterpene hydroquinones from marine origin. Tetrahedron 50: 4179-4184.
32. Urban S, Capon RJ (1992): 5-epi-Isospongiaquinone, a newsesquiterpene/ quinone antibiotic from an Australian marine sponge, Spongia hispida. J Nat Prod 55: 1638-1642.
33. Utkina NK, Denisenko VA, Scholokova OV, Virovaya MV, Prokof'eva NG (2003): Cyclosmenospongine, a new sesquiterpenoid aminoquinone from an Australian marine sponge Spongia sp. Tetrahedron 44: 101-102.
34. Wang SL, Cai B, Cui CB, Liu HW, Wu CF, Yao XS (2004): Diosgenin-3-O-α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranoside, a new anticancer agent from plant resources, induces apoptosis on human colon carcinoma HCT-15 cells via mitochondria-controlled apoptotic pathway. J Asian Nat Prod Res 6: 115-125.