Antifungal Activity of Alkaloids from the Seeds of Chimonanthus praecox

Abstract

Two alkaloids, D-calycanthine (1) and L-folicanthine (2), were isolated from the active MeOH extract of the seeds of Chimonanthus praecox LINK. The structures of the two compounds were established by (1)H- and (13)C-NMR, and MS (FAB, ESI) analyses. In the in vitro tests, compounds 1 and 2 showed significant inhibitory activities against five plant pathogenic fungi Exserohilum turcicum, Bipolaris maydis, Alternaria solani, Sclerotinia sderotiorum, and Fusarium oxysportium, among which B. maydis was found to be the most susceptible to 1 with an EC(50) value of 29.3 microg/ml, followed by S. sderotiorum to 2 with an EC(50) value of 61.2 microg/ml. To our knowledge, this is the first report of isolation and LC/MS/MS identification as well as of antifungal properties of these alkaloids from the seeds of this plant.

Effects of Medicinal Plant Extracts and Photosensitization on Aflatoxin Producing Aspergillus flavus (Raper and Fennell)

“…The bioactive compounds detected in this study have been shown to cause antimicrobial activities in other studies through various mechanisms [27, 36–38]. Increase in the concentration of bioactive compounds increases the antifungal activity as reported by [39].…”

Plant poisoning in domestic animals: epidemiological data from an Italian survey (2000–2011)

“…An unusual cattle poisoning case caused by wintersweet ( C praecox ) was reported. Calycanthine is the principal representative alkaloid of this plant and has long been recognised as a very powerful convulsant (Zhang and others 2009). According to CAV data, ingestion of the plant led to limb rigidity, hyperaesthesia and severe dyspnoea followed by death in the case of two out of three animals.…”

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

“…[52] Chimonanthines are dimeric HPIs linked between the C 3a of each unit. Related compounds include meso-chimonanthine; [53] (À)-chimonanthidine (29); [51] (À)-calycanthidine (30); [51] N chimonanthine; [50] and the antifungal agent (À)-folicanthine (31) [54] which was isolated from both Calycanthus floridus [55,56] and the seeds of Chimonanthus praecox. [51] The absolute configuration of (À)-31 was determined by chemical correlation with (À)-28 [51] and the total synthesis of its enantiomer (+)-31.…”

“…[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. [85] Natural products with an HPIC integrated into the peptide chain include omphalotins B-I (D: 55), [86,87] phakellistatin 3 (56) and isophakellistatin 3; [88] himastatin (57), in which the HPIC is part of a depsipeptide-chain; [89,90] its structure and stereochemistry was revised after the total synthesis.…”