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Volumn 2, Issue 4, 2004, Pages 154-163

Isolation of araguspongine M, a new stereoisomer of an Araguspongine/ Xestospongin Alkaloid, and dopamine from the marine sponge Neopetrosia exigua collected in Palau

Author keywords

Araguspongine xestospongin alkaloid; Cytotoxicity; HL 60; Marine sponge; Neopetrosia exigua

Indexed keywords


EID: 84902436174     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md204154     Document Type: Article
Times cited : (40)

References (41)
  • 1
    • 0000615497 scopus 로고
    • Significance of microbial symbionts in sponge evolution and ecology
    • Wilkinson, C. R. Significance of microbial symbionts in sponge evolution and ecology. Symbiosis 1987, 4, 135-146.
    • (1987) Symbiosis , vol.4 , pp. 135-146
    • Wilkinson, C.R.1
  • 2
    • 0000393614 scopus 로고
    • Electron microscope study of the association between some sponges and bacteria
    • Vacelet, J.; Donadey, C. Electron microscope study of the association between some sponges and bacteria. J. Exp. Mar. Ecol. 1977, 30, 301-314.
    • (1977) J. Exp. Mar. Ecol. , vol.30 , pp. 301-314
    • Vacelet, J.1    Donadey, C.2
  • 3
    • 0000379653 scopus 로고
    • Micromorphology and ultrastructure of Caribbean sclerosponges. I. Ceratoporella nicholsoni and Stromatospongia norae (Ceratoporellidae: Porifera)
    • Willenz, P.; Hartman, W. D. Micromorphology and ultrastructure of Caribbean sclerosponges. I. Ceratoporella nicholsoni and Stromatospongia norae (Ceratoporellidae: Porifera). Mar. Biol. 1989, 103, 387-402.
    • (1989) Mar. Biol , vol.103 , pp. 387-402
    • Willenz, P.1    Hartman, W.D.2
  • 5
    • 0002256581 scopus 로고    scopus 로고
    • Symbiotic bacteria in sponges: Sources of bioactive substances
    • Fusetani, N., Ed., Kaeger: Basel
    • Faulkner, D. J.; Harper, M. K.; Haygood, M. G.; Salomon, C. E.; Schmidt, E. W. Symbiotic bacteria in sponges: Sources of bioactive substances. In Drugs from the Sea; Fusetani, N., Ed., Kaeger: Basel, 2002; pp 107-119.
    • (2002) Drugs from the Sea , pp. 107-119
    • Faulkner, D.J.1    Harper, M.K.2    Haygood, M.G.3    Salomon, C.E.4    Schmidt, E.W.5
  • 6
    • 84902523364 scopus 로고    scopus 로고
    • Thin slices and homogenized samples were prepared from N. exigua and observed under a microscope in a laboratory at the Palau International Coral Reef Center in March, 2004
    • Thin slices and homogenized samples were prepared from N. exigua and observed under a microscope in a laboratory at the Palau International Coral Reef Center in March, 2004.
  • 7
    • 0024355073 scopus 로고
    • Araguspongines B, C, D, E, F, G, H, and J, new vasodilative bis-1-oxaquinolizidine alkaloids from an Okinawan marine sponge, Xestospongia sp
    • Kobayashi, M.; Kawazoe, K.; Kitagawa, I. Araguspongines B, C, D, E, F, G, H, and J, new vasodilative bis-1-oxaquinolizidine alkaloids from an Okinawan marine sponge, Xestopongia sp. Chem. Pharm. Bull. 1989, 37, 1676-1678. (Pubitemid 19176854)
    • (1989) Chemical and Pharmaceutical Bulletin , vol.37 , Issue.6 , pp. 1676-1678
    • Kobayashi, M.1    Kawazoe, K.2    Kitagawa, I.3
  • 8
    • 0000170122 scopus 로고    scopus 로고
    • Isomerization of dimeric 2,9-disubstituted 1-oxa-quinolizidine alkaloids and structural revision of araguspongines B and E, isolated from a marine sponge of Xestospongia sp
    • Kobayashi, M.; Miyamota, Y.; Aoki, S.; Murakami, N.; Kitagawa, I.; Ishida, T. Isomerization of dimeric 2, 9-disubstituted 1-oxaquinolizidine alkaloids and structural revision of araguspongines B and E, isolated from a marine sponge of Xestospongia sp. Heterocycles 1998, 47, 195-203. (Pubitemid 128658232)
    • (1998) Heterocycles , vol.47 , Issue.1 , pp. 195-203
    • Kobayashi, M.1    Miyamoto, Y.2    Aoki, S.3    Murakami, N.4    Kitagawa, I.5    In, Y.6    Ishida, T.7
  • 9
    • 0027489311 scopus 로고
    • Studies on glycolipids. VII. Isolation of two new sulfoquinovosyl diacylglycerols from the green alga Chlorella vulgaris
    • Morimoto, T.; Murakami, N.; Nagatsu, A.; Sakakibara, J. Studies on glycolipids VII. Isolation of two new sulfoquinovosyl diacylglycerols from green alga Chlorella vulgaris. Chem. Pharm. Bull. 1993, 41, 1545-1548. (Pubitemid 23326780)
    • (1993) Chemical and Pharmaceutical Bulletin , vol.41 , Issue.9 , pp. 1545-1548
    • Morimoto, T.1    Murakami, N.2    Nagatsu, A.3    Sakakibara, J.4
  • 11
    • 0028272376 scopus 로고
    • A monogalactosyl diacylglycerol from a cultured marine dinoflagellate, Scrippsiella trochoidea
    • Oshima, Y.; Yamada, S. H.; Matsunaga, K.; Moriya, T.; Ohizumi, Y. A monogalactosyl diacylglycerol from a cultured marine dinoflagellate, Scrippsiella trochoidea. J. Nat. Prod. 1994, 57, 534-536. (Pubitemid 24152913)
    • (1994) Journal of Natural Products , vol.57 , Issue.4 , pp. 534-536
    • Oshima, Y.1    Yamada, S.-H.2    Matsunaga, K.3    Moriya, T.4    Ohizumi, Y.5
  • 12
    • 0026650557 scopus 로고
    • Marine natural products. XXIX. Heterosigma-glycolipids I, II, III, and IV, four diacylglyceroglycolipids possessing σ3-polyunsaturated fatty acid residues, from the raphidophycean dinoflagellate heterosigma akashiwo
    • Kobayashi, M.; Hayashi, K.; Kawazoe, K.; Kitagawa, I. Marine natural products. XXIX. Heterosigma-glycolipids I, II, III, and IV, four diacylglyceroglycolipids possessing σ3-polyunsaturated fatty acid residues, from the raphidophycean dinoflagellate Heterosigma akashiwo. Chem. Pharm. Bull. 1992, 40, 1404-1410.
    • (1992) Chem. Pharm. Bull. , vol.40 , pp. 1404-1410
    • Kobayashi, M.1    Hayashi, K.2    Kawazoe, K.3    Kitagawa, I.4
  • 13
    • 0035862445 scopus 로고    scopus 로고
    • Characterization of lyso-galactolipids, C-2 and C-3 O-acyl trigalactosylglycerol isomers, obtained from the lichenized fungus Dictyonema glabratum
    • DOI 10.1016/S0378-1097(00)00520-6, PII S0378109700005206
    • Sassaki, G. L.; Gorin, P. A. J.; Iacomini, M. Characterization of lyso-galactolipids, C-2 and C-3 O-acyltrigalactosylglycerol isomers, obtained from the lichenized fungus Dictyonema glabratum. FEMS Microbiol. Lett. 2001, 194, 155-158. (Pubitemid 32332776)
    • (2001) FEMS Microbiology Letters , vol.194 , Issue.2 , pp. 155-158
    • Sassaki, G.L.1    Gorin, P.A.J.2    Iacomini, M.3
  • 14
    • 4644301905 scopus 로고    scopus 로고
    • Chemical constituents from typhonium flagelliforme
    • Huang P.; Karagianis G; Waterman P.G. Chemical constituents from Typhonium flagelliforme. Zhong Yao Cai 2004, 27, 173-175.
    • (2004) Zhong Yao Cai , vol.27 , pp. 173-175
    • Huang, P.1    Karagianis, G.2    Waterman, P.G.3
  • 15
    • 77951236331 scopus 로고    scopus 로고
    • Study on the steroid constituents of soft coral lobophytum microspiculatum
    • Xu X.; Guan Z.; Zeng L.; Su J.; Study on the steroid constituents of soft coral Lobophytum microspiculatum. Se Pu 1999, 17, 225-228.
    • (1999) Se Pu , vol.17 , pp. 225-228
    • Xu, X.1    Guan, Z.2    Zeng, L.3    Su, J.4
  • 16
    • 0036750304 scopus 로고    scopus 로고
    • The steroids of hexactinellid sponges
    • DOI 10.1007/s00114-002-0343-x
    • Blumenberg M.; Thiel V.; Pape T.; Michaelis W. The steroids of hexactinellid sponges. Naturwissenschaften 2002, 89, 415-419. (Pubitemid 35192096)
    • (2002) Naturwissenschaften , vol.89 , Issue.9 , pp. 415-419
    • Blumenberg, M.1    Thiel, V.2    Pape, T.3    Michaelis, W.4
  • 17
    • 0033842160 scopus 로고    scopus 로고
    • Isolation of bioactive 5,-epidioxy sterols from the marine sponge Luffariella cf variabilis
    • Gauvin, A.; Smadja, J.; Aknin, M.; Faure, R.; Gaydou, E. M. Isolation of bioactive 5α, 8α-epidioxy sterols from the marine sponge Luffariella cf. variabilis. Can. J. Chem. 2000, 78, 986-992. (Pubitemid 30666817)
    • (2000) Canadian Journal of Chemistry , vol.78 , Issue.7 , pp. 986-992
    • Gauvin, A.1    Smadja, J.2    Aknin, M.3    Faure, R.4    Gaydou, E.-M.5
  • 18
    • 0001679909 scopus 로고
    • Isolation and structure elucidation of nine new 5α,8α-epidoxy sterols from four marine organisms
    • Gunatilaka, A. A. L.; Gopichand, Y.; Francis, J. S.; Djerassi, C. Isolation and structure elucidation of nine new 5α,8α-epidoxy sterols from four marine organisms. J. Org. Chem. 1981, 46, 3860-3866.
    • (1981) J. Org. Chem. , vol.46 , pp. 3860-3866
    • Gunatilaka, A.A.L.1    Gopichand, Y.2    Francis, J.S.3    Djerassi, C.4
  • 19
    • 12244253707 scopus 로고    scopus 로고
    • Araguspongines K and L, new bioactive bis-1-oxaquinolizidine N-oxide alkaloids from red sea specimens of Xestospongia exigua
    • DOI 10.1021/np0202226
    • Orabi, K. Y.; El Sayed, K. A.; Hamann, M. T.; Dunbar, D. C; Al-Said, M. S.; Higa, T.; Kelly, M. Araguspongines K and L, new bioactive bis-oxaquinozilidine N-oxide alkaloids from red sea specimens of Xestospongia exigua. J. Nat. Prod. 2002, 65, 1782-1785. (Pubitemid 36055423)
    • (2002) Journal of Natural Products , vol.65 , Issue.12 , pp. 1782-1785
    • Orabi, K.Y.1    El Sayed, K.A.2    Hamann, M.T.3    Chuck Dunbar, D.4    Al-Said, M.S.5    Higa, T.6    Kelly, M.7
  • 20
    • 0036198872 scopus 로고    scopus 로고
    • (+)-7S-hydroxyxestospongin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D
    • DOI 10.1021/np010427z
    • Moon, S. S.; Macmillan, J. B.; Olmstead, M. M.; Ta, T. A.; Pessah, I. N.; Molinski, T. F. (+)-7S-hydroxyxestosponin A from the marine sponge Xestospongia sp. and absolute configuration of (+)-xestospongin D. J. Nat. Prod. 2002, 65, 249-254. (Pubitemid 34260788)
    • (2002) Journal of Natural Products , vol.65 , Issue.3 , pp. 249-254
    • Moon, S.-S.1    MacMillan, J.B.2    Olmstead, M.M.3    Ta, T.A.4    Pessah, I.N.5    Molinski, T.F.6
  • 21
    • 0001729486 scopus 로고
    • Structures of xestospongin A, B, C and D, novel vasodilative compounds from marine sponge, xestospongia exigua
    • Nakagawa, M.; Endo, M.; Tanaka, N.; Lee, G.-P. Structures of xestospongin A, B, C and D, novel vasodilative compounds from marine sponge, Xestospongia exigua. Tetrahedron Lett. 1984, 25, 3227-3230.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 3227-3230
    • Nakagawa, M.1    Endo, M.2    Tanaka, N.3    Lee, G.-P.4
  • 22
    • 0002566117 scopus 로고    scopus 로고
    • 3β, 3'β,-dimethylxestospongin C, a new bis-1-oxa quinolizidine alkaloid from the Palauan sponge xestospongia sp
    • Reddy, M. V. R.; Faulker, D. J. 3β, 3'β,-dimethylxestospongin C, a new bis-1-oxa quinolizidine alkaloid from the Palauan sponge Xestospongia sp. Nat. Prod. Lett. 1997, 11, 53-59.
    • (1997) Nat. Prod. Lett. , vol.11 , pp. 53-59
    • Reddy, M.V.R.1    Faulker, D.J.2
  • 23
    • 0028097087 scopus 로고
    • Bis-1-oxaquinolizidine from the sponge haliclona exigua
    • Venkateswarlu, Y.; Reddy, M. V. R.; Rao, J. V. Bis-1-oxaquinolizidine from the sponge Haliclona exigua. J. Nat. Prod. 1994, 57, 1283-1285.
    • (1994) J. Nat. Prod. , vol.57 , pp. 1283-1285
    • Venkateswarlu, Y.1    Reddy, M.V.R.2    Rao, J.V.3
  • 24
    • 0000406044 scopus 로고
    • Zur konfigurationsbestimmung von chinolizin-derivaten
    • Bohlmannn, F. Zur konfigurationsbestimmung von chinolizin-derivaten. Angew. Chem. 1957, 69, 641-644.
    • (1957) Angew. Chem. , vol.69 , pp. 641-644
    • Bohlmannn, F.1
  • 25
    • 0027998285 scopus 로고
    • Conformational considerations in 1-oxaquinolizidines related to the xestospongin/araguspongine family: Reassignment of stereostructures for araguspongines B and E
    • DOI 10.1021/jo00102a012
    • Hoye, T. R.; North, J. T.; Yao, L. J. Conformational considerations in 1-oxaquinolizidines related to the Xestospongin/araguspongine family: Reassignment of stereostructures for araguspongines B and E. J. Org. Chem. 1994, 59, 6904-6910. (Pubitemid 24375926)
    • (1994) Journal of Organic Chemistry , vol.59 , Issue.23 , pp. 6904-6910
    • Hoye, T.R.1    North, J.T.2    Yao, L.J.3
  • 26
    • 84902506344 scopus 로고
    • Structure correction of araguspongine B
    • (Structure correction of araguspongine B, J. Org. Chem. 1995, 60, 4958)
    • (1995) J. Org. Chem. , vol.60 , pp. 4958
  • 27
    • 0032555783 scopus 로고    scopus 로고
    • Marine biomolecules inhibit rat brain nitric oxide synthase activity
    • DOI 10.1016/S0300-483X(98)00067-5, PII S0300483X98000675
    • Rao, J.; Desaiah, D.; Vig, P.; Venkateswarlu, Y. Marine biomolecules inhibit rat brain nitric oxide synthase activity. Toxicology 1998, 129, 103-112. (Pubitemid 29023139)
    • (1998) Toxicology , vol.129 , Issue.2-3 , pp. 103-112
    • Venkateswara Rao, J.1    Desaiah, D.2    Vig, P.J.S.3    Venkateswarlu, Y.4
  • 29
    • 0030022491 scopus 로고    scopus 로고
    • Naturally occurring somatostatin and vasoactive intestinal peptide inhibitors. Isolation of alkaloids from two marine sponges
    • DOI 10.1055/s-2006-957790
    • Vassas, A.; Bourdy, G.; Paillard, J.; Lavayre, J.; Pais, M.; Quirion, J.; Debitus, C. Naturally occurring somatosatatin and vasoactive intestinal peptide inhibitors: Isolation of alkaloids from two marine sponges. Planta Med. 1996, 62, 28-30. (Pubitemid 26056305)
    • (1996) Planta Medica , vol.62 , Issue.1 , pp. 28-30
    • Vassas, A.1    Bourdy, G.2    Paillard, J.J.3    Lavayre, J.4    Pais, M.5    Quirion, J.C.6    Debitus, C.7
  • 31
    • 0021750742 scopus 로고
    • L-3, 4-dihydroxyphenylalanine-3-sulfate from the brown alga, ascophyllum nodosum
    • Laycock, M. V.; Rogan, M. A. L-3, 4-Dihydroxyphenylalanine-3-sulfate from the brown alga, Ascophyllum nodosum. J. Nat. Prod. 1984, 47, 1033-1036.
    • (1984) J. Nat. Prod. , vol.47 , pp. 1033-1036
    • Laycock, M.V.1    Rogan, M.A.2
  • 33
    • 0142063549 scopus 로고    scopus 로고
    • Are green tides harmful algal blooms? Toxic properties of water-soluble extracts from two bloom-forming macroalgae, Ulva fenestrata and Ulvaria obscura (ulvophyceae)
    • Nelson, T. A.; Lee, D. J.; Smith, B. C. Are green tides harmful algal blooms? Toxic properties of water-soluble extracts from two bloom-forming macroalgae, Ulva fenestrata and Ulvaria obscura (Ulvophyceae). J. Phycol. 2003, 39, 874-879. (Pubitemid 37274255)
    • (2003) Journal of Phycology , vol.39 , Issue.5 , pp. 874-879
    • Nelson, T.A.1    Lee, D.J.2    Smith, B.C.3
  • 34
    • 0025913248 scopus 로고
    • Varacin: A novel benzopentathiepin from lissoclinum vareau that is cytotoxic toward a human colon tumor
    • Davidson, B. S.; Molinski, T. F.; Barrows, L.; Ireland, C. M. Varacin: a novel benzopentathiepin from Lissoclinum vareau that is cytotoxic toward a human colon tumor. J. Am. Chem. Soc. 1991, 113, 4709-4710.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4709-4710
    • Davidson, B.S.1    Molinski, T.F.2    Barrows, L.3    Ireland, C.M.4
  • 35
    • 0028275466 scopus 로고
    • Lissoclinotoxins: Antibiotic polysulfur derivatives from the tunicate Lissoclinum perforatum. Revised structure of lissoclinotoxin A
    • DOI 10.1016/S0040-4020(01)80690-6
    • Litaudon, M.; Trigalo, F.; Martin, M. T.; Frappier, F.; Guyot, M. Lissoclinotoxins: Antibiotic polysulfur derivatives from the tunicate Lissoclinum perforatum. Revised structure of lissoclinotoxin A. Tetrahedron. 1994, 50, 5323-5334. (Pubitemid 24152214)
    • (1994) Tetrahedron , vol.50 , Issue.18 , pp. 5323-5334
    • Litaudon, M.1    Trigalo, F.2    Martin, M.-T.3    Frappier, F.4    Guyot, M.5
  • 36
    • 0028135113 scopus 로고
    • Pentathiepins and trithianes from two Lissoclinum species and a Eudistoma sp.: Inhibitors of protein kinase C
    • DOI 10.1016/S0040-4020(01)81200-X
    • Compagnone, R. S.; Faulkner, D. J. Carté, B. K., Chan, G., Freyer, A., Hemling, M. E., Hofmann, G. A., Mattern, M. R. Pentathiepins and trithianes from two Lissoclinum species and a Eudistoma sp.: inhibitors of protein kinase C. Tetrahedron. 1994, 50, 12785-12792. (Pubitemid 24337224)
    • (1994) Tetrahedron , vol.50 , Issue.45 , pp. 12785-12792
    • Compagnone, R.S.1    John Faulkner, D.2    Carte, B.K.3    Chan, G.4    Freyer, A.5    Hemling, M.E.6    Hofmann, G.A.7    Mattern, M.R.8
  • 37
    • 0027986753 scopus 로고
    • Five new alkaloids from the tropical ascidian, Lissoclinum sp. Lissoclinotoxin A is chiral
    • DOI 10.1021/jo00101a018
    • Searle, P. A.; Molinski, T. F. Five new alkaloids from the tropical ascidian, Lissoclinum sp. lissoclinotoxin A is chiral. J. Org. Chem. 1994, 59, 6600-6605. (Pubitemid 24356819)
    • (1994) Journal of Organic Chemistry , vol.59 , Issue.22 , pp. 6600-6605
    • Searle, P.A.1    Molinski, T.F.2
  • 38
    • 0020464178 scopus 로고
    • Marine natural products. X. Pharmacologically active glycolipids from the Okinawan marine sponge Phyllospongia foliascens (Pallas)
    • Kikuchi, H.; Tsukitani, Y.; Manda, T.; Fujii, T.; Nakanishi, H.; Kobayashi, M.; Kitagawa, Marine natural products X. Pharmacologically active glycolipids from the Okinawan marin sponge Phyllospongia foliascens. Chem. Pharm. Bull. 1982, 30, 3544-3547. (Pubitemid 13210095)
    • (1982) Chemical and Pharmaceutical Bulletin , vol.30 , Issue.10 , pp. 3544-3547
    • Kikuchi, H.1    Tsukitani, Y.2    Manda, T.3
  • 39
    • 0036221685 scopus 로고    scopus 로고
    • A new screening method for antimitotic substances and isolation of glycolipids as stimulators of tubulin polymerization from Okinawan sponge Pseudoceratina sp
    • Meguro, S.; Namikoshi, M.; Kobayashi, H. A new screening method for antimitotic substances and isolation of glycolipids as stimulators of tubulin polymerization form Okinawan sponge Pseudoceratian sp. J. Antibiot. 2002, 55, 256-262. (Pubitemid 34296236)
    • (2002) Journal of Antibiotics , vol.55 , Issue.3 , pp. 256-262
    • Meguro, S.1    Namikoshi, M.2    Kobayashi, H.3
  • 40
    • 84902523365 scopus 로고    scopus 로고
    • The voucher specimen of the same sponge is also kept in the Marine Biotechnology Institute, Japan as 02PA-006, which was identified by Professor P. Bergquist as Neopetrosia exigua Kirkpatrick (Order Petrosida, Family Petrosiidae)
    • The voucher specimen of the same sponge is also kept in the Marine Biotechnology Institute, Japan as 02PA-006, which was identified by Professor P. Bergquist as Neopetrosia exigua Kirkpatrick (Order Petrosida, Family Petrosiidae).
  • 41
    • 0141892547 scopus 로고    scopus 로고
    • Three new chlorine containing antibiotics from a marine-derived fungus Aspergillus ostianus collected in Pohnpei
    • Namikoshi, M.; Negishi, R.; Nagai, H.; Dmitrenok, A.; Kobayashi, H. Three new chlorin containing antibiotics from a marine-derived fungus Aspergillus ostianus collected in Pohnpe J. Antibiot. 2003, 56, 755-761. (Pubitemid 37258871)
    • (2003) Journal of Antibiotics , vol.56 , Issue.9 , pp. 755-761
    • Namikoshi, M.1    Negishi, R.2    Nagai, H.3    Dmitrenok, A.4    Kobayashi, H.5


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