title: Potential allelopathic indole diketopiperazines produced by the plant endophytic Aspergillus fumigatus using the one strain-many compounds method.
abstract: On the basis of the OSMAC (one strain-many compounds) strategy, 14 indole diketopiperazine (DKP) alkaloids, including spirotryprostatins (1-3), tryprostatins (4-6), and cyclotryprostatins (7-14), were isolated from the endophyte Aspergillus fumigatus associated with Melia azedarach L. Their structures were identified by nuclear magnetic resonance and electrospray ionization mass spectrometry data. All the indole DKPs were evaluated for plant growth regulation using the lettuce (Lactuca sativa) seedling growth bioassay, which showed the plant growth influence of the seedling. Among these compounds tested, a tryprostatin-type compound, brevianamide F (6), was identified as a new type of natural potential plant growth inhibitor with a response index (RI) higher than that of the positive control glyphosate, a broad-spectrum systemic herbicide. 6 can also inhibit turnip (Raphanus sativus) shoot and root elongation with RIs of -0.76 and -0.70, respectively, at 120 ppm, and it strongly inhibits amaranth (Amaranthus mangostanus) seedling growth with a high RI of -0.9 at 40 ppm. The structure-allelopathic activity relationship analysis of these isolated alkaloids indicates that tryprostatin-type alkaloids without the C5 prenyl and methoxy group give the most potent inhibition of seedling growth. Brevianamide F (6) could be used to develop a natural eco-friendly herbicide.
authors.affiliation: Shaanxi Engineering Center of Bioresource Chemistry & Sustainable Utilization, College of Science, Northwest A&F University , Yangling 712100, Shaanxi, China.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhang
authors.forename: Shi-Qiong
authors.initials: SQ
authors.lastname: Wang
authors.forename: Hao-Yu
authors.initials: HY
authors.lastname: Tang
authors.forename: Xiao-Jun
authors.initials: XJ
authors.lastname: Li
authors.forename: Lu
authors.initials: L
authors.lastname: Zhang
authors.forename: Jian
authors.initials: J
authors.lastname: Xiao
authors.forename: Yu-Qi
authors.initials: YQ
authors.lastname: Gao
authors.forename: An-Ling
authors.initials: AL
authors.lastname: Zhang
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
mesh_terms: D027721:Amaranthus / Q000187:drug effects; D001232:Aspergillus fumigatus / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D054659:Diketopiperazines / Q000737:chemistry / Q000494:pharmacology*; D060026:Endophytes / Q000737:chemistry; D018525:Germination / Q000187:drug effects; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology*; D026121:Indole Alkaloids / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology; D018545:Lactuca / Q000187:drug effects / Q000254:growth & development; D009682:Magnetic Resonance Spectroscopy; D031585:Melia / Q000382:microbiology; D015394:Molecular Structure; D010937:Plant Growth Regulators / Q000494:pharmacology; D031224:Raphanus / Q000187:drug effects; D036226:Seedlings / Q000187:drug effects; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
chemical_list: D054659:Diketopiperazines; D006540:Herbicides; D026121:Indole Alkaloids; D007211:Indoles; D010937:Plant Growth Regulators; C000590722:brevianamide F