Biological activities of pyrrolidinoindoline alkaloids from Calycodendron milnei.
Certain genera of the tribe Psychotrieae, specifically Calycodendron and Psychotria, found on Pacific Islands, synthesize a series of Nb-methyltryptamine-derived alkaloids made by linking together 2 to 8 pyrrolidinoindoline units. Nine alkaloids of this class have been isolated from the aerial parts and stem bark of Calycodendron milnei, a species endemic to the Vaté Islands (New Hebrides), and examined for potential application as anti-cancer and anti-infective agents. All members of the series exhibited readily detected cytotoxic activity against proliferating and non-proliferating Vero African green monkey kidney cells in culture, with the most potent activity being exhibited by vatamine and quadrigemine C. Only hodgkinsine A exhibited substantial antiviral activity against a DNA virus, herpes simplex type 1, and an RNA virus, vesicular stomatitis virus. All members of the series showed readily detected anti-bacterial, anti-fungal, and anti-candidal activities using both tube dilution and disc diffusion assay methods. The most potent anti-microbial alkaloids were hodgkinsine A and quadrigemine C, which exhibited minimum inhibitory concentration (MIC) values as low as 5 micrograms/ml.
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002455:Cell Division / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D005658:Fungi / Q000187:drug effects; D018259:Herpesvirus 1, Human / Q000187:drug effects; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010946:Plants, Medicinal; D011759:Pyrrolidines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014709:Vero Cells; D014721:Vesicular stomatitis Indiana virus / Q000187:drug effects
D000470:Alkaloids; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D007211:Indoles; D011759:Pyrrolidines