Inconspicamide, new N-acylated serinol from the marine sponge Stelletta inconspicua

Bioscience, Biotechnology and Biochemistry

Volumn 72, Issue 11, 2008, Pages 3055-3058

  Ueoka, Reiko ^a   Fujita, Tsuyoshi ^b   Iwashita, Takashi ^b   Van Soest, Rob W M ^c   Matsunaga, Shigeki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

Amide; Cytotoxic metabolite; Marine sponge

Indexed keywords

AMIDES; ETHERS; ORGANIC COMPOUNDS; SPECTROSCOPIC ANALYSIS;

CERVICAL CANCER CELLS; CYTOTOXIC ACTIVITIES; CYTOTOXIC METABOLITE; MARINE SPONGE; MARINE SPONGES; SPECTROSCOPIC DATUMS;

DATA STRUCTURES;

ANTINEOPLASTIC AGENT; INCONSPICAMIDE; PROPANEDIOL DERIVATIVE; SERINOL; STEARIC ACID DERIVATIVE;

ACYLATION; ANIMAL; ARTICLE; CHEMISTRY; DRUG DEVELOPMENT; HELA CELL; HUMAN; ISOLATION AND PURIFICATION; SPONGE (PORIFERA);

ACYLATION; ANIMALS; ANTINEOPLASTIC AGENTS; DRUG DISCOVERY; HELA CELLS; HUMANS; PORIFERA; PROPYLENE GLYCOLS; STEARIC ACIDS;

STELLETTA;

EID: 56749174732     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.80457     Document Type: Article

References (17)

1. Cragg, G. M., Kingston, D. G. I., and Newman, D. J., "Anticancer Agents from Natural Products," Taylor & Francis, Boca Raton (2005).
2. Lee, S. Y., Zhao, Q., Choi, K., Hong, J., Lee, D. S., Lee, C. O., and Jung, J. H., A new glycerol ether from a marine sponge Stelletta species. Nat. Prod. Sci., 9, 232-234 (2003).
3. Kobayashi, H., Miyata, Y., Okada, K., Fujita, T., Iwashita, T., Nakao, Y., Fusetani, N., and Matsunaga, S., The structures of three new shishididemniols from a tunicate of the family Didemnidae. Tetrahedron, 63, 6748-6754 (2007).
4. Kupchan, S. M., Britton, R. W., Ziegler, M. F., and Sigel, C. W., Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica. J. Org. Chem., 38, 178-179 (1973).
5. Kay, L. E., Keifer, P., and Saarinen, T., Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity. J. Am. Chem. Soc., 114, 10663-10665 (1992).
6. Bax, A., Azolos, A., Dinya, Z., and Sudo, K., Structure elucidation of the antibiotic desertomycin through the use of new two-dimensional NMR techniques. J. Am. Chem. Soc., 108, 8056-8063 (1986).
7. Ohtani, I., Kusumi, T., Kashman, Y., and Kakisawa, H., High-field FT NMR application of Mosher's method. The absolute configuration of marine terpenoids. J. Am. Chem. Soc., 113, 4092-4096 (1991).
8. 1H NMR spectroscopy: principles and applications. Chem. Eur. J., 11, 5509-5522 (2005).
9. Mayer, M., and Guyot, M., New sphingosines from the marine sponge Grayella cyatophora. J. Nat. Prod., 65, 1722-1723 (2002).
10. Sun, Y., Xu, Y., Liu, K., Hua, H., Zhu, H., and Pei, Y., Gracilarioside and graciliamides from the red alga Gracilaria asiatica. J. Nat. Prod., 69, 1488-1491 (2006).
11. Chakrabarty, M., Batabyal, A., and Barua, A. K., New ceramides from the hypotensive extract of a sea anemone, Paracondylactis indicus. J. Nat. Prod., 57, 393-395 (1994).
12. Shin, J., and Seo, Y., Isolation of new ceramides from the gorgonian Acabaria undulate. J. Nat. Prod., 58, 948-953 (1995).
13. Garg, H. S., and Agrawal, S., A novel sphingosine derivative from the sponge Spirastrella inconstans. J. Nat. Prod., 58, 442-445 (1995).
14. Hattori, T., Adachi, K., and Shizuri, Y., New ceramide from marine sponge Haliclona koremella and related compounds as antifouling substances against macroalgae. J. Nat. Prod., 61, 823-826 (1998).
15. Tanaka, I., Matsuoka, S., Murata, M., and Tachibana, K., A new ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate Coolia monotis. J. Nat. Prod., 61, 685-688 (1998).
16. Chalfant, C. E., and Spiegel, S., Sphingosine 1-phosphate and ceramide 1-phosphate: expanding roles in cell signaling. J. Cell Sci., 118, 4605-4612 (2005).
17. Bieberich, E., Kawaguchi, T., and Yu, R. K., N-acylated serinol is a novel ceramide mimic inducing apoptosis in neuroblastoma cells. J. Biol. Chem., 275, 177-181 (2000).