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Oxygenated Terpenoids from the Australian Sponges Coscinoderma matthewsi and Dysidea sp., and the Nudibranch Chromodoris albopunctata
Peter L.
Katavic
A
,
Pinus
Jumaryatno
A
B
,
John N. A.
Hooper
C
,
Joanne T.
Blanchfield
A
and
Mary J.
Garson
A
D
A
School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia. B
Pharmacy Department, Faculty of Mathematics and Natural Sciences, Universitas Islam Indonesia, Yogyakarta, Indonesia. C
Queensland Museum, PO Box 3300, South Brisbane, Qld 4101, Australia. D
Corresponding author. Email: m.garson@uq.edu.au
Australian Journal of Chemistry
65(5)
531-538 http://dx.doi.org/10.1071/CH12010
Submitted: 13 January 2012 Accepted: 3 April 2012 Published:
28
May
2012
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Abstract
The isolation and structure elucidation of seven new oxygenated terpenoids and eight known terpene metabolites from marine invertebrates collected at the Inner Gneerings Reef, South East Queensland, is discussed. Investigation of the sponge Coscinoderma matthewsi yielded an epoxylactone derivative (1) of the known furanoterpene tetradehydrofurospongin-1 (2). A chemical investigation of the dissected nudibranch Chromodoris albopunctata provided the new oxygenated diterpenes 12α-acetoxyspongian-16-one (10), 20-acetoxyspongian-16-one (12), 20-oxyspongian-16-one propionate (13) and 12α,20-dioxyspongian-16-one dipropionate (14) in conjunction with three other known diterpene metabolites, while two new chromodorolides, D (17) and E (18), in addition to four known diterpenes were isolated from a Dysidea sp. 
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References
[1]
G. Cimino, A. Fontana, A. Cutignano, M. Gavagnin, Phytochem. Rev. 2004, 3, 285.
| CrossRef | CAS |
[2]
M. Gavagnin, A. Fontana, Curr. Org. Chem. 2000, 4, 1201.
| CrossRef | CAS |
[3]
G. Cimino, Phytochem. Rev. 2010, 9, 547.
| CrossRef | CAS |
[4]
(a) M. A. González, Curr. Bioact. Comp. 2007, 3, 1.
| CrossRef | (b) R. A. Keyzers, P. T. Northcote, M. T. Davies-Coleman, Nat. Prod. Rep. 2006, 23, 321.
| CrossRef |
[5]
(a) M. Hyosu, J. Kimura, J. Nat. Prod. 2000, 63, 422.
| CrossRef | CAS | (b) S. De Marino, C. Festa, M. V. D’Auria, M.-L. Bourguet-Kondracki, S. Petek, C. Debitus, R. M. Andres, M. C. Terenico, M. Paya, A. Zampella, Tetrahedron 2009, 65, 2905.
| CrossRef | (c) A. Loukaci, I. Le Saout, M. Samadi, S. Leclerc, E. Damiens, L. Meijer, C. Debitus, M. Guyot, Bioorg. Med. Chem. 2001, 9, 3049.
| CrossRef | (d) J. Kimura, M. Hyosu, Chem. Lett. 1999, 28, 61.
| CrossRef | (e) J. Kimura, E. Ishizuka, Y. Nakao, W. Y. Yoshida, P. J. Scheuer, M. Kelly-Borges, J. Nat. Prod. 1998, 61, 248.
| CrossRef | (f) J. Kimura, E. Ishizuka, Y. Nakao, W. Y. Yoshida, P. J. Scheuer, M. Kelly-Borges, J. Nat. Prod. 1998, 61, 862.
| CrossRef |
[6]
K. W. L. Yong, J. N. A. Hooper, M. J. Garson, ARKIVOC 2008, vi, 100.
[7]
A. Fontana, L. Albarella, G. Scognamiglio, M. Uriz, G. Cimino, J. Nat. Prod. 1996, 59, 869.
| CrossRef | CAS |
[8]
I. A. van Altena, D. A. Miller, Aust. J. Chem. 1989, 42, 2181.
| CrossRef | CAS |
[9]
N. H. Tran, J. N. A. Hooper, R. J. Capon, Aust. J. Chem. 1995, 48, 1757.
| CrossRef |
[10]
G. Cimino, S. De Stefano, L. Minale, Experientia 1974, 30, 18.
| CrossRef | CAS |
[11]
X.-D. Luo, S.-H. Wu, Y.-B. Ma, D.-G. Wu, J. Nat. Prod. 2000, 63, 947.
| CrossRef | CAS |
[12]
M. R. Kernan, D. J. Faulkner, J. Org. Chem. 1988, 53, 2773.
| CrossRef | CAS |
[13]
C. J. Barrow, J. W. Blunt, M. H. G. Munro, J. Nat. Prod. 1989, 52, 346.
| CrossRef | CAS |
[14]
K. W. L. Yong, A. A. Salim, M. J. Garson, Tetrahedron 2008, 64, 6733.
| CrossRef | CAS |
[15]
Suciati, L. K., Lambert, M. J. Garson, Aust. J. Chem. 2011, 64, 757.
| CrossRef |
[16]
M. R. Kernan, R. C. Cambie, P. R. Bergquist, J. Nat. Prod. 1990, 53, 724.
| CrossRef | CAS |
[17]
P. Karuso, W. C. Taylor, Aust. J. Chem. 1986, 39, 1629.
| CAS |
[18]
G. Cimino, D. De Rosa, S. De Stefano, L. Minale, Tetrahedron 1974, 30, 645.
| CrossRef | CAS |
[19]
T. Miyamoto, K. Sakamoto, H. Amano, Y. Arakawa, Y. Nagarekawa, T. Komori, R. Higuchi, T. Sasaki, Tetrahedron 1999, 55, 9133.
| CrossRef | CAS |
[20]
E. Manzo, M. Gavagnin, M. J. Somerville, S.-C. Mao, M. L. Ciavatta, E. Mollo, P. J. Schupp, M. J. Garson, G. Cimino, J. Chem. Ecol. 2007, 33, 2325.
| CrossRef | CAS |
[21]
W. C. Taylor, S. Toth, Aust. J. Chem. 1997, 50, 895.
| CrossRef | CAS |
[22]
M. Arnó, M. A. González, R. J. Zaragozá, J. Org. Chem. 2003, 68, 1242.
| CrossRef |
[23]
A. J. Blake, M. A. González, M. J. Gil-Gimeno, Acta Crystallogr. 2006, C62, o208.
| CAS |
[24]
K. Gustafson, R. J. Andersen, H. Cun-Heng, J. Clardy, Tetrahedron Lett. 1985, 26, 2521.
| CrossRef | CAS |
[25]
E. J. Dumdei, J. Kubanek, J. E. Coleman, J. Pika, R. J. Andersen, J. R. Steiner, J. Clardy, Can. J. Chem. 1997, 75, 773.
| CrossRef | CAS |
[26]
A. R. Carroll, J. Lamb, R. Moni, J. N. A. Hooper, R. J. Quinn, J. Nat. Prod. 2008, 71, 884.
| CrossRef | CAS |
[27]
MARINLIT database, Department of Chemistry, University of Canterbury: http://www.chem.canterbury.ac.nz/marinlit/marinlit.html.
[28]
K. H. Jang, J. Jeon, S. Ryu, H.-S. Lee, K.-B. Oh, J. Shin, J. Nat. Prod. 2008, 71, 1701.
| CrossRef | CAS |
[29]
B. C. M. Potts, D. J. Faulkner, J. Am. Chem. Soc. 1991, 113, 6321.
| CrossRef | CAS |
[30]
C. M. Ireland, J. E. Biskupiak, G. J. Hite, M. Rapposch, P. J. Scheuer, J. R. Ruble, J. Org. Chem. 1984, 49, 559.
| CrossRef | CAS |
[31]
J. Rodriguez, R. Riguera, C. Debitus, J. Org. Chem. 1992, 57, 4624.
| CrossRef | CAS |
[32]
R. N. Asolkar, R. P. Maskey, E. Helmke, H. Laatsch, J. Antibiot. 2002, 55, 893.
| CrossRef | CAS |
[33]
K. W. L. Yong, M. J. Garson, P. V. Bernhardt, Acta Crystallogr. 2009, C65, o167.
| CAS |
[34]
The specific rotation of 7α-acetoxyspongian-16-one ( 8) was not published; [17] however, our sample gave –34.7 ( c 0.047, CHCl 3).
[35]
A. G. Gonzalez, D. M. Estrada, J. D. Martin, V. S. Martin, C. Perez, R. Perez, Tetrahedron 1984, 40, 4109.
| CrossRef | CAS |
[36]
A. Rudi, Y. Kashman, Tetrahedron 1990, 46, 4019.
| CrossRef | CAS |
[37]
E. J. Dumdei, E. D. de Silva, R. J. Andersen, M. I. Choudhary, J. Clardy, J. Am. Chem. Soc. 1989, 111, 2712.
| CrossRef | CAS |
[38]
S. A. Morris, E. D. de Silva, R. J. Andersen, Can. J. Chem. 1991, 69, 768.
| CrossRef | CAS |
[39]
W. Rungprom, W. Chavasiri, U. Kokpol, A. Kotze, M. J. Garson, Mar. Drugs 2004, 2, 101.
| CrossRef | CAS |
[40]
Suciati, L. K., Lambert, B. P., Ross, M. A., Deseo, M. J., Garson, Aust. J. Chem. 2011, 64, 489.
| CrossRef |
[41]
N. Coleman, 1001 Nudibranchs: Catalogue of Indo-Pacific Sea Slugs 2000, p. 67 (Neville Coleman’s Underwater Geographic: Springwood, Qld).
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