ABSTRACT
Apocarotenoids are metabolites originated by degradation of carotenes through the loss of carbon atoms placed at the side chain of their structure as consequence of oxydative reactions. We present here the first review of apocarotenoids in the fungi mucorales Phycomyces blakesleeanus, Blakeslea trispora and Mucor mucedo. This review is divided into two parts: the first one presents their structures and sources, whereas the second part is dedicated to their chemical synthesis.
Subject(s)
Carotenoids/chemistry , Carotenoids/chemical synthesis , Mucorales/chemistry , Molecular StructureABSTRACT
Several preparations were obtained from the aerial parts of predomesticated Lavandula luisieri, including the essential oil and ethanolic, hexane, and ethyl acetate extractives. Additionally, pilot plant vapor pressure extraction was carried out at a pressure range of 0.5-1.0 bar to give a vapor pressure oil and an aqueous residue. A chemical study of the hexane extract led to the isolation of six necrodane derivatives (1, 2, and 4-7), with four of these (1, 2, 5, and 7) being new, as well as camphor, a cadinane sesquiterpene (9), tormentic acid, and ursolic acid. The EtOAc and EtOH extracts contained a mixture of phenolic compounds with rosmarinic acid being the major component. Workup of the aqueous residue resulted in the isolation of the necrodane 3 and (1R*,2S*,4R*)-p-menth-5-ene-1,2,8-triol (8), both new natural compounds. The structures of the new compounds were established based on their spectroscopic data. The phytotoxic and nematicidal activities of these compounds were evaluated.
Subject(s)
Antinematodal Agents/isolation & purification , Antinematodal Agents/pharmacology , Terpenes/isolation & purification , Terpenes/pharmacology , Animals , Anti-Infective Agents/pharmacology , Antinematodal Agents/chemistry , Aphids/drug effects , Lavandula/chemistry , Molecular Structure , Monoterpenes , Nuclear Magnetic Resonance, Biomolecular , Oils, Volatile/analysis , Plant Components, Aerial/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacology , Spain , Spodoptera/drug effects , Terpenes/chemistry , Triterpenes/isolation & purification , Ursolic AcidABSTRACT
A simple method to obtain extracts enriched in bioactive limonoids from Citrus aurantium L. seeds has been developed, using solvents of increasing polarity. 1H NMR data from the extracts revealed that the highest amounts of limonoids were present in the t-butylmethylether extract. The comparison between extracts obtained from dormant and germinating seeds showed that the latter contained almost double amounts of limonoids, revealing germinating seeds as an excellent source of those bioactive compounds.
Subject(s)
Citrus/chemistry , Plant Extracts/analysis , Seeds/growth & development , Citrus/growth & development , Germination , Limonins , Seeds/chemistryABSTRACT
Artemisia granatensis, an endemic endangered plant species from Sierra Nevada (Spain) has been successfully cultivated in artificial systems (plants in artificial soil and transformed in vitro roots) to generate enough plant biomass (aerial and root) to allow for its chemical and biological study and at the same time to provide with methods for the sustainable production of the plant and its metabolites. A eudesmanolide (17) along with six sesquiterpenes (11-16), nine monoterpenes (2-10), one nor-monoterpene (1), three acetylenic spiroacetal enoleters (18-20) and one coumarin (21) have been identified from the aerial plant ethanolic extract. Acetylenic spiroacetal enoleters 18-19 and coumarins 21-23 have been isolated from the transformed root ethanolic extract. These extracts and some isolated compounds or mixtures of them have been tested for their insect antifeedant effects against Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi. Significant antifeedant properties were determined for the aerial plant extract, spiroacetals 19-20 and secoguaianolides 13+14 and 16.
