title: Acridone Alkaloids from Swinglea glutinosa (Rutaceae) and Their Effects on Photosynthesis.
abstract: Continuing our search for herbicide models based on natural products, we investigated the action mechanisms of five alkaloids isolated from Swinglea glutinosa (Rutaceae): Citrusinine-I (1), glycocitrine-IV (2), 1,3,5-trihydroxy-10-methyl- 2,8-bis(3-methylbut-2-en-1-yl)-9(10H)-acridinone (3), (2R)-2-tert-butyl-3,10-dihydro-4,9-dihydroxy-11-methoxy-10-methylfuro[3,2-b]acridin-5(2H)-one (4), and (3R)-2,3,4,7-tetrahydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-12H-pyrano[2,3-a]acridin-12-one (5) on several photosynthetic activities in an attempt to find new compounds that affect photosynthesis. Through polarographic techniques, the compounds inhibited the non-cyclic electron transport in the basal, phosphorylating, and uncoupled conditions from H2 O to methylviologen (=MV). Therefore, they act as Hill reaction inhibitors. This approach still suggested that the compounds 4 and 5 had their interaction site located at photosystem I. Studies on fluorescence of chlorophyll a suggested that acridones (1-3) have different modes of interaction and inhibition sites on the photosystem II electron transport chain.
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo (UNIFESP), 09972270, Diadema, SP, Brazil.
authors.forename: Pedro H
authors.initials: PH
authors.lastname: Arato Ferreira
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos (UFSCar), 13565905, São Carlos, SP, Brazil.
authors.forename: Djalma A P
authors.initials: DA
authors.lastname: Dos Santos
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos (UFSCar), 13565905, São Carlos, SP, Brazil.
authors.forename: Maria Fátima das G F
authors.initials: MF
authors.lastname: da Silva
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos (UFSCar), 13565905, São Carlos, SP, Brazil.
authors.forename: Paulo C
authors.initials: PC
authors.lastname: Vieira
authors.affiliation: Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, 04510 México, DF, Mexico.
authors.forename: Beatriz
authors.initials: B
authors.lastname: King-Diaz
authors.affiliation: Departamento de Bioquímica, Facultad de Química, Universidad Nacional Autónoma de México (UNAM), Ciudad Universitaria, 04510 México, DF, Mexico. blas@servidor.unam.mx.
authors.forename: Blas
authors.initials: B
authors.lastname: Lotina-Hennsen
authors.affiliation: Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo (UNIFESP), 09972270, Diadema, SP, Brazil. tveiga@unifesp.br.
authors.forename: Thiago A M
authors.initials: TA
authors.lastname: Veiga
mesh_terms: D000166:Acridines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D054831:Acridones; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002734:Chlorophyll / Q000737:chemistry / Q000378:metabolism; D004579:Electron Transport / Q000187:drug effects; D005453:Fluorescence; D010788:Photosynthesis / Q000187:drug effects*; D045331:Photosystem I Protein Complex / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D045332:Photosystem II Protein Complex / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D027821:Rutaceae / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000166:Acridines; D054831:Acridones; D000470:Alkaloids; D045331:Photosystem I Protein Complex; D045332:Photosystem II Protein Complex; D002734:Chlorophyll; C041300:acridone
keywords: Acridone alkaloids; Hill reaction inhibitors; Photosynthesis; Swinglea glutinosa