Dehydroconicasterol and Aurantoic Acid, a Chlorinated Polyene Derivative, from the Indonesian Sponge Theonella swinhoei

被引:16
作者
Angawi, Rihab F. [1 ]
Calcinai, Barbara [2 ]
Cerrano, Carlo [3 ]
Dien, Henny Adeleida [4 ]
Fattorusso, Ernesto [1 ]
Scala, Fernando [1 ]
Taglialatela-Scafati, Orazio [1 ]
机构
[1] Univ Naples Federico 2, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy
[2] Univ Politecn Marche, Dipartimento Sci Mare, I-60131 Ancona, Italy
[3] Univ Genoa, Dipartimento Studio Terr & Risorse, I-16132 Genoa, Italy
[4] Sam Ratulangi Univ, Fac Fishery & Marine Sci, Manado, Indonesia
来源
JOURNAL OF NATURAL PRODUCTS | 2009年 / 72卷 / 12期
关键词
PAPUA-NEW-GUINEA; MARINE SPONGE; BIOSYNTHESIS; GLYCOSIDES; MACROLIDE; STEROLS;
D O I
10.1021/np900669d
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
The chlorinated polyene aurantoic acid (1) and the 4-methylene sterol dehydroconicasterol (2) were isolated from the Indonesian sponge Theonella swinhoei, and their structures were elucidated by interpretation of spectroscopic data. Aurantoic acid is a unique member in the class of naturally occurring conjugated polyene derivatives, while dehydroconicasterol is the likely biogenetic precursor of the major Theonella 4-methylene sterols.
引用
收藏
页码:2195 / 2198
页数:4
相关论文
共 16 条
  • [1] Isolation of swinholide A and related glycosylated derivatives from two field collections of marine cyanobacteria
    Andrianasolo, EH
    Gross, H
    Goeger, D
    Musafija-Girt, M
    McPhail, KP
    Leal, RM
    Mooberry, SL
    Gerwick, WH
    [J]. ORGANIC LETTERS, 2005, 7 (07) : 1375 - 1378
  • [2] STRUCTURE OF SWINHOLIDE-A, A NEW MACROLIDE FROM THE MARINE SPONGE THEONELLA-SWINHOEI
    CARMELY, S
    KASHMAN, Y
    [J]. TETRAHEDRON LETTERS, 1985, 26 (04) : 511 - 514
  • [3] IDENTIFICATION OF 2 CONJUGATED PENTAENOIC ACIDS IN INSECT FAT, AJE
    CASON, J
    DAVIS, R
    SHEEHAN, MH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (18) : 2621 - &
  • [4] Oxygenated cembranoids of the decaryiol type from the Indonesian soft coral Lobophytum sp.
    Fattorusso, Ernesto
    Romano, Adriana
    Taglialatela-Scafati, Orazio
    Irace, Carlo
    Maffettone, Carmen
    Bavestrello, Giorgio
    Cerrano, Carlo
    [J]. TETRAHEDRON, 2009, 65 (15) : 2898 - 2904
  • [5] Papuamides A-D, HIV-inhibitory and cytotoxic depsipeptides from the sponges Theonella mirabilis and Theonella swinhoei collected in Papua New Guinea
    Ford, PW
    Gustafson, KR
    McKee, TC
    Shigematsu, N
    Maurizi, LK
    Pannell, LK
    Williams, DE
    de Silva, ED
    Lassota, P
    Allen, TM
    Van Soest, R
    Andersen, RJ
    Boyd, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (25) : 5899 - 5909
  • [6] BIOSYNTHESIS OF STEROLS IN HIGHER PLANTS
    GOAD, LJ
    GOODWIN, TW
    [J]. BIOCHEMICAL JOURNAL, 1966, 99 (03) : 735 - &
  • [7] Polytheonamides A and B, highly cytotoxic, linear polypeptides with unprecedented structural features, from the marine sponge, Theonella swinhoeiii
    Hamada, T
    Matsunaga, S
    Yano, G
    Fusetani, N
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) : 110 - 118
  • [8] STEROLS IN MARINE-INVERTEBRATES .22. ISOLATION AND STRUCTURE ELUCIDATION OF CONICASTEROL AND THEONELLASTEROL, 2 NEW 4-METHYLENE STEROLS FROM THE RED-SEA SPONGES THEONELLA-CONICA AND THEONELLA-SWINHOEI
    KHO, E
    IMAGAWA, DK
    ROHMER, M
    KASHMAN, Y
    DJERASSI, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) : 1836 - 1839
  • [9] STRUCTURE OF SWINHOLIDE-A - A POTENT CYTO-TOXIC MACROLIDE FROM THE OKINAWAN MARINE SPONGE THEONELLA-SWINHOEI
    KOBAYASHI, M
    TANAKA, J
    KATORI, T
    MATSUURA, M
    KITAGAWA, I
    [J]. TETRAHEDRON LETTERS, 1989, 30 (22) : 2963 - 2966
  • [10] THEONELLAMIDES A-E, CYTOTOXIC BICYCLIC PEPTIDES, FROM A MARINE SPONGE THEONELLA SP
    MATSUNAGA, S
    FUSETANI, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) : 1177 - 1181