Table 1.
Summary of the reported biological activity of hapalindole-type alkaloids from Stigonematales including inhibition of microbes, cytotoxicity and plant/animal toxicity, as well as biochemical, molecular and cellular targets.
| Antimicrobial | Cytotoxicity | Biochemical, Molecular or Cellular | Plant/Animal Toxicity | |||
|---|---|---|---|---|---|---|
| Bacteria | Fungi | Algae | ||||
| Hapalindoles | ||||||
| Tetracyclic (Group 1) | A, G–H, I–J, T, X [29,31,34,42] | G [42] | A, J, X [34] | A, H–J, U, X [34] | Modulate Na+ channels in neuroblastoma [59] | Insecticidal [32,60,61] Teratogenicity/vertebrate toxicity [39,41] |
| Tricyclic (Group 2) | E [62] | E [62] | E–F [62,63] | C, E [34,62] | Modulate Na+ channels in neuroblastoma [59] RNA polymerase inhibition [62,64] |
Insecticidal [32,60] |
| Hapalindolinones (Group 3) | Inhibits arginine vassopressin binding, and adenylate cyclase [35] | |||||
| Ambiguines | ||||||
| Tetracyclic (Group 4) | A–C, H [38,42] | A–C, H [38,42] | A–C [42] | Teratogenicity/vertebrate toxicity [39,41] | ||
| Pentacyclic (Group 5) | E–F, G nitrile, I, K–O [37,38,42] | E–F, I, K–O, P [37,38,42] | E–F, G nitrile, K–O [37,42] | Apoptosis, inhibition of NF-kb, IKKb and ICAM-1 [65] Inhibits mitosis (plant cells) [66] Elevates ROS [65,66] |
Phytotoxic [66] | |
| Fischambiguines (Group 6) | A, B [42] | A [42] | ||||
| Fischerindoles (Group 7) | L [34] | L [34] | descholor I nitrile, L [34,44] | Teratogenicity/vertebrate toxicity [41] | ||
| Welwitindolinones | ||||||
| Welwitindolinone A (Group 8) | A [45] | |||||
| Welwitindolinone B (Group 9) | N-methyl C isothiocyanate [67] | Inhibits microtubules and mitosis [67] Inhibit P-glycoprotein MDR [67,68] |
Insecticidal [45] | |||