Table 4.
Biological activities of NRPs isolated from marine sponges and tunicates.
| NRPs | Chemical class | Origin | Disease/target | Biological active value (IC50/GI50/ID50/ED50) | Reference(s) |
|---|---|---|---|---|---|
| Miraziridine A (1) | Linear penta peptide | Theonella aff. mirabilis | Cancer/inhibit protease cathepsin B | 1.4 μg/mL | Nakao et al., 2000 |
| Haligramides A-B (2–3) | Cyclic hexapeptides | Haliclona nigra | Cancer/A-549 (lung) HCT-15(colon) SF-539 (CNS) SNB-19 (CNS) |
5.17–15.6 μg/mL 3.89–8.82 μg/mL | Rashid et al., 2000 |
| Prepatellamide A (4) | Cyclic peptide | Lissoclinum patella | Cancer/P388 murine leukemia cell lines | 5 μg/mL | Fu et al., 2000 |
| Tamandarins A-B (5–6) | Depsipeptides | Didemnid ascidian | Cancer/pancreatic carcinoma BX- PC3, prostatic cancer DU-145, head and neck carcinoma UMSCC10b |
1.79, 2.00 μg/mL 1.36, 1.53 μg/mL 0.99, 1.76 μg/mL |
Vervoort et al., 2000 |
| Microsclerodermins F–I (7–10) | Cyclic peptides | Microscleroderma sp. | Cancer/HCT-116 cell line | 1.8, 2.4, 1.0, and 1.1 μg/mL | Qureshi et al., 2000 |
| Wainunuamide (11) | Cyclic hexapeptide | Stylotella aurantium | Cancer/A2780 ovarian, K562 leukemia cancer cells | 19.15 and 18.36 μg/mL | Tabudravu et al., 2001 |
| Leucamide A (12) | Cyclic hexapeptide | Leucetta microraphis | Cancer/Tumor cell lines HM02, HepG2, Huh7 |
5.2 μg/mL 5.9 μg/mL 5.1 μg/mL |
Kehraus et al., 2002 |
| Axinellin C (13) | Cyclic octapeptide | S. aurantium | Cancer/A2780 ovarian, K562 leukemia cancer cells | 13.17 and 4.46 mg/mL | Tabudravu et al., 2002 |
| Milnamide D (14) | Linear peptide | Cymbastela sp. | Cancer/HCT-116 cells | 66 nM | Chevallier et al., 2003 |
| Kapakahines E–G (15–17) | – | Cribrochalina olemda | Cancer/P388 murine leukemia cells | 5.0 μg/mL | Nakao et al., 2003 |
| Didmolamides A- B (18–19) | Cyclic hexapeptides | Didemnum molle | Cancer Tumor cell lines (A549, HT29, and MEL28) | 10–20 μg/mL | Rudi et al., 2003 |
| Bistratamides E–J (20- 25) | Cyclic hexapeptides | Lissoclinum bistratum | Cancer/Human colon tumor (HCT-116) cell line | 3, 7.9; 4, 28; 5, 5; 6, 1.7; 7, 9; 8, 1 μg/mL | Perez and Faulkner, 2003 |
| Milnamide C (26) | – | Auletta sp. | Cancer/MDA-MB-435 cancer cells | 3.2 × 10−1 μg/mL | Sonnenschein et al., 2004 |
| Scleritodermin A (27) | Cyclic peptide | Scleritoderma nodosum | Cancer | <2 μM | Schmidt et al., 2004 |
| Microcionamides A-B (28–29) | – | Clathria abietina | Cancer/Human breast tumor cell lines MCF-7 and SKBR-3 |
125 and 98 nM 177 and 172 nM |
Davis et al., 2004 |
| Kendarimide A (30) | Linear peptide | Haliclona sp. | Cancer/KB-C2 cells | – | Aoki et al., 2004 |
| Phakellistatin 14 (31) | Cycloheptapeptide | Phakellia sp. | Cancer/Murine lymphocytic leukemia P388 cell line | 5 μg/mL | Pettit and Tan, 2005 |
| Polytheonamides A-B (32–33) | Polypeptides | T. swinhoei | Cancer/P388 murine leukemia cells | 78, 68 pg/mL | Hamada et al., 2005 |
| Neopetrosiamides A- B (34–35) | Tricyclic peptides | Neopetrosia sp. | Cancer | 6 μg/mL | Williams et al., 2005 |
| Seragamides A–F (36–37) | Depsipeptides | Suberites japonicus | Cancer | 0.01, 0.02, 0.01, 0.01, and 0.04 mg/mL | Tanaka et al., 2006 |
| Theopapuamide (38) | Cyclic depsipeptide | T. swinhoei | Cancer/CEM-TART HCT-116 cell lines |
0.5 μM 0.9 μM |
Ratnayake et al., 2006 |
| Azumamide A- E (39–47) | Cyclotetrapeptides | Mycale izuensis | Cancer | – | Maulucci et al., 2007 |
| Callyaerin G (48) | Cyclic peptide | Callyspongia aerizusa | Cancer/Mouse lymphoma cell line (L5178Y) and HeLa cells | 0.53 and 5.4 ug/mL | Ibrahim et al., 2008 |
| Stylopeptide 2 (49) | Cyclodecapeptide | Stylotella sp. | Cancer/BT-549 and HS 578T breast cancer cell lines | – | Brennan et al., 2008 |
| Ciliatamides A-C (50–52) | Lipopeptides | Aaptos ciliata | Cancer/HeLa cells | 50, 4.5, and 50 μg/mL | Nakao et al., 2008 |
| Diazonamides C–E (53–55) | Macrocyclic peptides | Diazona sp. | Cancer/Human tumor cell lines (A549, HT29, MDA-MB 231) |
2.2, 2.9, 8.0 μg/mL 1.8, 2.9, 5.2 μg/mL 2.2, 3.1, 9.0 μg/mL |
Fernández et al., 2008 |
| Rolloamide A- B (56–57) | Cyclic heptapeptides | Eurypon laughlini | Cancer | 0.4−5.8 μM | Williams et al., 2009 |
| Euryjanicin A (58) | Cycloheptapeptide | Prosuberites laughlini | Cancer | – | Vicente et al., 2009 |
| Callyaerin A–F (59–64) and H (65) | Cyclic peptides | C. aerizusa | Cancer/L5178Y cell line | 0.39 and 0.48 μM | Ibrahim et al., 2010 |
| Papuamides E-F (66–67) | Depsipeptides | Melophlus sp. | Cancer/Brine shrimp | 92 and 106 μg/mL | Prasad et al., 2011 |
| Stylissamide X (68) | Octapeptide | Stylissa sp. | Cancer/HeLa cells | 0.1 μM to 10 μM | Arai et al., 2012 |
| Gombamide A (69) | Hexapeptide | Clathria gombawuiensis | Cancer/K562 and A549 cell lines | 6.9 and 7.1 μM | Woo et al., 2013 |
| Microspinosamide (70) | Cyclic depsipeptide | Sidonops microspinosa | HIV | 0.2 μg/mL | Rashid et al., 2001 |
| Neamphamide A (71) | Cyclic depsipeptide | Neamphius huxleyi | HIV | 8 nM | Oku et al., 2004 |
| Mirabamides A-D (72–75) | Cyclic depsipeptide | Siliquariaspongia mirabilis | HIV | 40 and 140 nM, 140 nM and 1.3 μM 190 nM and 3.9 μM |
Plaza et al., 2007 |
| Homophymine A (76) | Cyclodepsipeptide | Homophymia sp. | HIV/PBMC cell line | 75 nM | Zampella et al., 2008 |
| Celebeside A-C (77–79) | Depsipeptides | S. mirabilis | HIV/Colon carcinoma (HCT-116) cells |
2.1 and 4.0 μg/mL 1.9 ± 0.4 μg/mL |
Plaza et al., 2008 |
| Theopapuamides B–D (80–82) | |||||
| Mutremdamide A (83) Koshikamides C-H (84–89) | Cyclic depsipeptide | Theonella sp. | HIV | 2.3 and 5.5 μM | Plaza et al., 2010 |
| Ceratospongamide (90) | Cyclic heptapeptide | Sigmadocia symbiotica | Inflammation | 32 nM | Tan et al., 2000 |
| Halipeptin A-B (91–92) | Cyclic depsipeptide | Haliclona sp. | Inflammation | 300 μg/kg (i.p.) | Randazzo et al., 2001 |
| Perthamide C-D (93–94) | Cyclopeptide | T. swinhoei | Inflammation | – | Festa et al., 2009 |
| Solomonamide A- B (95–96) | Cyclic peptide | T. swinhoei | Inflammation | – | Festa et al., 2011 |
| Stylissatin A (97) | Cyclic peptide | Stylissa massa | Murine macrophage RAW264.7 | 87 μM | Kita et al., 2013 |
| Dicynthaurin (98) | – | Halocynthia aurantium | Antimicrobial | – | Lee I. H. et al., 2001 |
| Nagahamide A (99) | Depsipeptide | T. swinhoei | Antibacterial | – | Okada et al., 2002 |
| Plicatamide (100) | Octapeptide | Styela plicata | Antimicrobial | – | Tincu et al., 2003 |
| Callipeltins F-I (101–104) | – | Latrunculia sp. | Antifungal/Candida albicans | 10−4 M | Sepe et al., 2006 |
| Callipeltins J-M (105–108) | – | Latrunculia sp. | Antifungal/C. albicans | 4−10 M | D'Auria et al., 2007 |
| Citronamides A- B (109–110) | – | Citronia astra | Antifungal/Saccharomyces cerevisiae | 8 μg/mL | Carroll et al., 2009 |
| Renieramide (111) | Cyclic tripeptide | Reniera sp. | – | – | Ciasullo et al., 2002 |
| Phoriospongins A- B (112–113) | Depsipeptide | Phoriospongia sp. and Callyspongia bilamellata | Nematocidal/Haemonchus contortus | 100, 194 μg/mL | Capon et al., 2002 |