New Type of Trimeric and Pentameric Indole Alkaloids from Psychotria rostrata

Abstract

Two new tryptamine-related alkaloids, psychotrimine and psychopentamine, were isolated from the leaves of Psychotria rostrata, and their novel structures were elucidated on the basis of spectroscopic analyses.

The GenusPsychotria: Phytochemistry, Chemotaxonomy, Ethnopharmacology and Biological Properties

“…44 Two tryptamine-related alkaloids, psychotrimine (17) and psychopentamine (18), were isolated from the leaves of P. rostrata. 77 The crude extracts from the roots and branches of P. prunifolia led to the isolation of several alkaloids such as 10-hydroxyisodeppeaninol (19), 10-hydroxyantirhine N-oxide (20), 14-oxoprunifoleine (21) and strictosamide (22). 74 From the leaves of P. pilifera was isolated the compound psychotripine (23), a trimeric pyrroloindoline derivative with a hendecacyclic system bearing a hexahydro-1,3,5-triazine unit.…”

“…76 From the leaves of the same species were isolated some other alkaloids like psychotrimine (17) and psychopentamine (18), which showed anti-bactericidal activity against resistant grampositive bacteria Bacillus subtilis and S. aureus. 77,117 In a study made by Moraes et al, 111 ten Psychotria species (P. pubigera, P. ruelliifolia, P. suterela, P. stachyoides, P. capitata, P. glaziovii, P. leiocarpa, P. nuda, P. racemosa and P. vellosiana) were evaluated for antimycobacterial activity, in an attempt to find new antituberculosis agents. From the evaluated extracts the species P. pubigera, P. ruelliifolia and P. stachyoides were the most active against Mycobacterium.…”

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

“…[57] Furthermore, psycholeine, [58] meso-pseudophrynamine A [15] and the recently isolated flustramines O (32) and P (33) [9] each have two HPI units (Scheme 2). Natural compounds containing more than two HPI units comprise idiospermuline (34) [59] and the hodgkinsines (35), [50,52,60,61] with three HPI units; psychopentamine [62] and quadrigemines A, B, C (36), and I, [50,52,58,61,63] with four. Quadrigemine C is a weak antagonist of the SRIF (somatostatin) receptor, like psycholeine and meso-pseudophrynamine A. Isopsychotridines A and B (37) [61] and psychotridine, with five; [50,61] oleoidine, [50] with six; and caledonine, [50] with seven.…”

“…[62] Another noteworthy example is the epipolythiodioxopiperazine family, whose members exhibit numerous bioactivities, including antitumor, antimicrobial, antinematodal and cytotoxicity; notable members include the chetomin (50), chaetocochins A (51), B (52), and C, and dethio-tetra(methylthio)chetomin, all isolated from the solid-state fermented rice culture of the fungus Chaetomium cochliodes. [78][79][80][81][82][83][84] An extra degree of complexity is shown in kapakahines C (53) and D (54), which are macrocyclic peptides formed through a bond between the N 8 of an HPIC located at the N-terminal of the linear structure and the C 4a of an a-carboline unit, located close to the C-terminal.…”

Antioxidant Research in Asia in the Period from 2000-2008

“…Chinese Wolf-berry Solanaceae Leaf Antioxidant [99,100] Solanum melongena L. Egg plant Solanaceae Fruit Antioxidant [100] Chasalia chartacea No common name Rubiaceae Whole plant Antioxidant and NO inhibitory [135] Hedyotis verticillata L. Hedyotis plant Rubiaceae Whole plant Antioxidant and NO inhibitory [135] Lasianthus oblongus No common name Rubiaceae Whole plant Antioxidant and NO [135] King [135,151,152] Spermacoce articularis L. f. poaia Rubiaceae Whole plant Antioxidant and NO inhibitory [135] Spermacoce exilis (L. O. Pacific false buttonweed Rubiaceae Whole plant Antioxidant [135] Williams) C. D. Adams Citrus hystrix D.C Kaffir lime Rutaceae Leaf Antioxidant [99,100] Thea chinensis Sims. Green tea Theaceae Leaf Antioxidant [99,100] Piper sarmentosum Roxb.…”