Table 1.
Examples of cyclic peptides and their structural features characterized from ascidians and sponges
| Compound | Molecular weight | Number of amino acids | Amino acids | Oxazole | Oxazoline | Thiazole | Thiazoline | Prenyl | SS bridge | Bioactivity | Source organism | Reference |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Ascidiacyclamide | 757.0 | 8 | ITVCITVC | 2 | 2 | Cytotoxic | Lissoclinum patella | Ishida et al. 1988; Schmitz et al. 1989 | ||||
| Axinastatin 1 | 752.9 | 7 | FVVPVNP | Cytostatic against cancer cells | Axinella sp. | Pettit et al. 1994 | ||||||
| Axinastatin 2 | 766.9 | 7 | FVLPVNP | |||||||||
| Axinastatin 3 | 781.0 | 7 | FILPVNP | |||||||||
| Axinellin C | 938.1 | 8 | FPLTVPWP | Stylotella aurantium | Tabudravu et al. 2002a | |||||||
| Bistratamide A | 570.7 | 6 | ITACFC | 1 | 2 | Cytotoxic | Lissoclinum bistratum | Degnan et al. 1989b; Foster et al. 1992; Perez and Faulkner 2003 | ||||
| Bistratamide B | 568.7 | 6 | ITACFC | 1 | 1 | 1 | ||||||
| Bistratamide C | 503.6 | 6 | VSACVC | 1 | 2 | |||||||
| Bistratamide D | 530.6 | 6 | VTVSVC | 1 | 1 | 1 | ||||||
| Bistratamide E | 543.2 | 6 | VTVCVC | 1 | 2 | |||||||
| Bistratamide F | 532.7 | 6 | VTVSVC | 2 | 1 | |||||||
| Bistratamide G | 528.6 | 6 | VTVSVC | 2 | 1 | |||||||
| Bistratamide H | 544.7 | 6 | VTVCVC | 1 | 2 | |||||||
| Bistratamide I | 548.7 | 6 | VTVSVC | 1 | 1 | |||||||
| Bistratamide J | 564.7 | 6 | VTVCVC | 2 | ||||||||
| Comoramide A | 668.9 | 6 | ITFTAC | 1 | 1 | 1 | Mild cytotoxicity against tumor cells | Didemnum molle | Rudi et al. 1998 | |||
| Comoramide B | 686.9 | 6 | ITFTAC | 1 | 1 | |||||||
| Cyclodidemnamide | 693.9 | 7 | FTVPCVC | 1 | 1 | 1 | Weakly cytotoxic | Didemnum molle | Toske and Fenical 1995; Arrault et al. 2002 | |||
| Cyclodidemnamide B | 689.9 | 7 | ITVPCLC | 2 | ||||||||
| Cyclonellin | 963.1 | 8 | YTANPRYP | Axinella carteri | Milanowski et al. 2004 | |||||||
| Cycloxazoline | 546.7 | 6 | VTVTVT | 3 | Cytotoxic | Lissoclinum bistratum | Hambley et al. 1992 | |||||
| Didmolamide A | 538.6 | 6 | ACFTAC | 1 | 2 | Didemnum molle | Rudi et al. 2003 | |||||
| Didmolamide B | 556.7 | 6 | ACFTAC | 2 | ||||||||
| Dolastatin I | 516.6 | 6 | ITVSAC | 1 | 1 | 1 | Cytotoxic | Dolabella auricularia | Sone et al. 1997 | |||
| Dolastatin E | 490.6 | 6 | ASACIC | 1 | 1 | 1 | Ojika et al. 1995 | |||||
| Haliclonamide A | 857.0 | 8 | PASYPTIP | 1 | 1 | 1 | Antifouling | Haliclona sp. | Guan et al. 2001; Sera et al. 2003 | |||
| Haliclonamide B | 788.9 | 8 | PASYPTIP | 1 | 1 | |||||||
| Haliclonamide D | 806.9 | 8 | PASYPTIP | 1 | ||||||||
| Haliclonamide E | 875.0 | 8 | PASYPTIP | 1 | 1 | |||||||
| Hexamollamide | 696.9 | 6 | VVCTFP | 1 | 1 | Moderate cytotoxicity against HeLa S3 cells | Didemnum molle | Teruya et al. 2008 | ||||
| Hymenamide A | 880.1 | 7 | VPFWRPP | Immunomodulating activity | Hymeniacidon sp. | Kobayashi et al. 1993 | ||||||
| Hymenamide B | 830.9 | 7 | NFVEFPP | |||||||||
| Hymenamide C | 826.9 | 7 | FGPELWP | Napolitano et al. 2001 | ||||||||
| Hymenamide D | 769.9 | 7 | YDPLAIP | |||||||||
| Hymenamide E | 854.0 | 7 | TTPYFFP | |||||||||
| Hymenamide F | 765.0 | 7 | AVMLRPP | |||||||||
| Hymenamide G | 893.1 | 8 | YVPLILPP | Tsuda et al. 1994 | ||||||||
| Hymenamide H | 904.1 | 8 | LPWVPLTP | |||||||||
| Hymenamide J | 1,099.3 | 8 | YDFWKVYP | |||||||||
| Hymenamide K | 1,007.2 | 8 | YDFWKAVP | |||||||||
| Lissoclinamide 1 | 705.9 | 7 | ICFPTVC | 1 | 2 | Cytotoxic | Lissoclinum patella a | Wasylyk et al. 1983; Degnan et al. 1989a; Schmitz et al. 1989; Donia et al. 2006; Hawkins et al. 1990; Morris et al. 2000 | ||||
| Lissoclinamide 2 | 679.9 | 7 | ACFPTIC | 1 | 1 | 1 | ||||||
| Lissoclinamide 3 | 679.9 | 7 | ACFPTIC | 1 | 1 | 1 | ||||||
| Lissoclinamide 4 | 741.9 | 7 | FCFPTVC | 1 | 1 | 1 | ||||||
| Lissoclinamide 5 | 739.9 | 7 | FCFPTVC | 1 | 2 | |||||||
| Lissoclinamide 6 | 741.9 | 7 | FCFPTVC | 1 | 1 | 1 | ||||||
| Lissoclinamide 7 | 743.9 | 7 | FCFPTVC | 1 | 2 | |||||||
| Lissoclinamide 8 | 741.9 | 7 | FCFPTVC | 1 | 1 | 1 | ||||||
| Lissoclinamide 9 | 707.9 | 7 | VCFPTIC | 1 | 1 | 1 | ||||||
| Lissoclinamide 10 | 726.9 | 7 | ICFPTIC | 1 | 2 | |||||||
| Mayotamide A | 694.0 | 7 | VPCICMC | 1 | 2 | Didemnum molle | Rudi et al. 1998 | |||||
| Mayotamide B | 679.9 | 7 | VPCVCMC | 1 | 2 | |||||||
| Mollamide | 808.0 | 7 | IPISFPC | 1 | 1 | Cytotoxic | Didemnum molle | McKeever and Pattenden 2003; Donia et al. 2008b | ||||
| Mollamide B | 696.9 | 6 | VFPTVC | 1 | 1 | Cytotoxic against several cancer cell lines | ||||||
| Mollamide C | 618.8 | 6 | IPGSLC | 1 | 1 | |||||||
| Nairaiamide A | 802.1 | 7 | VTIPIIP | 1 | Lissoclinum bistratum | Foster and Ireland 1993 | ||||||
| Nairaiamide B | 816.1 | 7 | ITIPIIP | 1 | ||||||||
| Patellamide A | 743.0 | 8 | ISVCITVC | 2 | 2 | Cytotoxic antineoplastic; patellamides B and C had multidrug reversing activity | Lissoclinum patella a | Ireland et al. 1982; Fu et al. 1998; Schmitz et al. 1989; McDonald and Ireland 1992; Rashid et al. 1995; Schmidt et al. 2005; Donia et al. 2006 | ||||
| Patellamide B | 777.0 | 8 | LTACITFC | 2 | 2 | |||||||
| Patellamide C | 763.0 | 8 | VTACITFC | 2 | 2 | |||||||
| Patellamide D | 777.0 | 8 | ITACITFC | 2 | 2 | |||||||
| Patellamide E | 791.0 | 8 | VTVCITFC | 2 | 2 | |||||||
| Patellamide F | 763.0 | 8 | VTVCITFC | 2 | 2 | |||||||
| Patellamide G | 795.0 | 8 | ITACLTFC | 1 | 2 | |||||||
| Patellin 2 | 733.0 | 6 | TVPTLC | 1 | 2 | Moderately cytotoxic | Lissoclinum patella a | Donia et al. 2008a, Zabriskie et al. 1990 | ||||
| Patellin 3 | 943.0 | 8 | TLPVPTLC | 1 | 2 | |||||||
| Patellin 6 | 963.2 | 8 | TFPVPTVC | 1 | 2 | |||||||
| Phakellistatin 1 | 828.0 | 7 | YPIPIFP | Cancer cell growth inhibitory | Phakellia costata sponge and Stylotella aurantium | Pettit et al. 1993a, b | ||||||
| Phakellistatin 2 | 828.0 | 7 | YPFPIIP | Cell growth inhibitory | Phakellia carteri | Tabudravu et al. 2002b | ||||||
| Phakellistatin 7 | 1,109.4 | 10 | YIPPIFALPP | Cancer cell growth inhibitory | Phakellia costata sponge | Pettit et al. 1995 | ||||||
| Phakellistatin 8 | 1,137.4 | 10 | YIPPIFVLPP | |||||||||
| Phakellistatin 9 | 1,123.4 | 10 | YVPPIFVLPP | |||||||||
| Phakellistatin 12 | 1,139.4 | 10 | IFTLPPYIPP | Phakellia sp. | Pettit and Tan 2003; Li et al. 2003 | |||||||
| Phakellistatin 13 | 798.9 | 7 | LWPFGPT | Phakellia fusca | ||||||||
| Stylisin 1 | 828.0 | 7 | LPYPIFP | Stylissa caribica | Mohammed et al. 2006 | |||||||
| Stylisin 2 | 812.0 | 7 | IPYPPFP | |||||||||
| Stylissamide A | 845.0 | 7 | VYPYKPP | Stylissa caribica | Schmidt et al. 2007 | |||||||
| Stylissamide B | 812.0 | 7 | IYPFPPP | |||||||||
| Stylissamide C | 862.0 | 7 | FIPYPFP | |||||||||
| Stylissamide D | 828.0 | 7 | FIPYPLP | |||||||||
| Tawicyclamide A | 806.1 | 8 | VCFCICVP | 2 | 1 | Weakly cytotoxic | Lissoclinum patella | McDonald et al. 1992 | ||||
| Tawicyclamide B | 772.0 | 8 | VCLCICVP | 2 | 1 | |||||||
| Trunkamide A | 838.0 | 7 | TSIAPFC | 1 | 2 | Cytotoxic, multidrug reversing activity | Lissoclinum patella a | Caba et al. 2001; Salvatella et al. 2003; Donia et al. 2008a | ||||
| Ulicyclamide | 677.8 | 7 | FPTICAC | 1 | 2 | Not reported | Lissoclinum patella | Ireland and Scheuer 1980; Wasylyk et al. 1983 | ||||
| Ulithiacyclamide | 763.0 | 8 | CTLCCTLC | 2 | 2 | 1 | Cytotoxic | Lissoclinum patella a | Ireland and Scheuer 1980; Ireland et al. 1982; Williams et al. 1989; Fu et al. 1998 | |||
| Ulithiacyclamide B | 797.0 | 8 | CTFCCTLC | 2 | 2 | 1 | ||||||
| Ulithiacyclamide E | 833.0 | 8 | CTFCCTLC | 2 | 1 | |||||||
| Ulithiacyclamide F | 815.0 | 8 | CTFCCTLC | 1 | 2 | 1 | ||||||
| Ulithiacyclamide G | 815.0 | 8 | CTFCCTLC | 1 | 2 | 1 | ||||||
| Wainunuamide | 745.9 | 7 | GLFPHPP | Weakly cytotoxic | Stylotella aurantium | Tabudravu et al. 2001 |
The peptides are organized alphabetically. The sequence of the peptide is presented in linear form so that the last amino acid is cysteine or proline. The number of each modification is given after the amino acids of the core peptide
aConfirmed to be produced by the Prochloron spp. symbiotic partner of the ascidian