Hyrtimomines A-C, New Heteroaromatic Alkaloids from a Sponge Hyrtios sp.

被引:56
作者
Momose, Rei [1 ]
Tanaka, Naonobu [1 ]
Fromont, Jane [2 ]
Kobayashi, Jun'ichi [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Western Australian Museum, Weishpool Dc, WA 6986, Australia
关键词
INDOLE ALKALOIDS; MARINE;
D O I
10.1021/ol400687b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new alkaloids, hyrtimomines A-C (1-3), were isolated from an Okinawan marine sponge Hyrtios sp. The structures of 1-3 were elucidated on the basis of spectroscopic analysis and application of a phenylglycine methyl ester (PGME) method. Hyrtimomines A (1) and B (2) are heteroaromatic alkaloids possessing a fused hexacyclic 6/5/6/6/7/5 ring system, while hyrtimomine C (3) is an alkaloid consisting of hydroxyindole and azepino-hydroxyindole moieties. Hyrtimomine A (1) exhibited cytotoxicity against KB and L1210 cells.
引用
收藏
页码:2010 / 2013
页数:4
相关论文
共 12 条
  • [1] Novel neuronal nitric oxide synthase (nNOS) selective inhibitor, aplysinopsin-type indole alkaloid, from marine sponge Hyrtios erecta
    Aoki, S
    Ye, Y
    Higuchi, K
    Takashima, A
    Tanaka, Y
    Kitagawa, I
    Kobayashi, M
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (10) : 1372 - 1374
  • [2] Blunt JW, 2013, NAT PROD REP, V30, P237, DOI [10.1039/c2np20112g, 10.1039/d0np00089b]
  • [3] Hyrtinadine A, a bis-indole alkaloid from a marine sponge
    Endo, Taeko
    Tsuda, Masashi
    Fromont, Jane
    Kobayashi, Jun'ichi
    [J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (03): : 423 - 424
  • [4] Gesashidine a, β-carboline alkaloid with an imidazole ring from a thorectidae sponge
    Iinuma, Y
    Kozawa, S
    Ishiyama, H
    Tsuda, M
    Fukushi, E
    Kawabata, J
    Fromont, J
    Kobayashi, J
    [J]. JOURNAL OF NATURAL PRODUCTS, 2005, 68 (07): : 1109 - 1110
  • [5] A β-Carboline Alkaloid from the Papua New Guinea Marine Sponge Hyrtios reticulatus
    Inman, Wayne D.
    Bray, Walter M.
    Gassner, Nadine C.
    Lokey, R. Scott
    Tenney, Karen
    Shen, Young Yongchun
    TenDyke, Karen
    Suh, Ted
    Crews, Phillip
    [J]. JOURNAL OF NATURAL PRODUCTS, 2010, 73 (02): : 255 - 257
  • [6] HYRTIOSIN-A AND HYRTIOSIN-B, NEW INDOLE ALKALOIDS FROM THE OKINAWAN MARINE SPONGE HYRTIOS-ERECTA
    KOBAYASHI, J
    MURAYAMA, T
    ISHIBASHI, M
    KOSUGE, S
    TAKAMATSU, M
    OHIZUMI, Y
    KOBAYASHI, H
    OHTA, T
    NOZOE, S
    SASAKI, T
    [J]. TETRAHEDRON, 1990, 46 (23) : 7699 - 7702
  • [7] CLAVICIPITIC ACID - ITS STRUCTURE, BIOSYNTHESIS, AND ROLE IN ERGOT ALKALOID FORMATION
    ROBBERS, JE
    OTSUKA, H
    FLOSS, HG
    ARNOLD, EV
    CLARDY, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) : 1117 - 1121
  • [8] Hyrtiazepine, an azepino-indole-type alkaloid from the Red Sea marine sponge Hyrtios erectus
    Sauleau, Pierre
    Martin, Marie-Therese
    Dau, Marie-Elise Tran Huu
    Youssef, Diaa T. A.
    Bourguet-Kondracki, Marie-Lise
    [J]. JOURNAL OF NATURAL PRODUCTS, 2006, 69 (12): : 1676 - 1679
  • [9] Hyrtioseragamines A and B, New Alkaloids from the Sponge Hyrtios Species
    Takahashi, Yohei
    Iinuma, Yoshiro
    Kubota, Takaaki
    Tsuda, Masashi
    Sekiguchi, Mitsuhiro
    Mikami, Yuzuru
    Fromont, Jane
    Kobayashi, Jun'ichi
    [J]. ORGANIC LETTERS, 2011, 13 (04) : 628 - 631
  • [10] Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids
    Yabuuchi, T
    Kusumi, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) : 397 - 404