Brief Introduction to Citrus Limonoids.ppt

Brief Introduction to Citrus Limonoids Jiaxing Li TAMU-College Station TAMUK-Citrus Center Bitterness problem in citrus industry Cause 1. The flavonoids e.g. naringin-- species related to pumello Cause 2. The limonoids e.g. limonin Biochemistry of Limonoids in Citrus A group of highly oxygenated tetracyclic triterpenoids -- Citrus related genera Tow forms in citrus: 1. Limonoid aglycones (LA) -- 50 isolated from the Rutaceae (36 from Citrusrelated genera) 2. Limonoid glucosides (LG) -- 17 isolated Biochemistry Cont. Relation between LA and LG 1. LA: bitter, insoluble in water 2. LG: non-bitter, water-soluble 3. LA glucosidated to LG--fruit maturation --- Natural Debittering process --- Occurs only in fruit tissues and seeds Delayed bitterness PH6.5 Limonoid D-ring lactone hydrolase Closed D-ring is the key structure An example of natural debittering and delayed bitterness Navel oranges and Valencia oranges in California Early to mid-season Navel juice has delayed bitterness, Valencia dose not Reason: Short maturation period of the Navel (2 months); 6 months for the Valencia allow: LA LG Structures of some of the major Limonoids in citrus Structures Cont. Biosynthesis of Citrus Limonoids Four groups of LA 1. Limonin group 2. Calamin group 3. Ichangensin group 4. 7α-acetate limonoid Biosynthetic pathways of each group of these limonoids have been elucidated Example of Biosynthetic pathways: limonin group Analytical Methods of Citrus Limonoids Thin-layer chromatography (TLC) -- for limonoid detection Nuclear Magnetic Resonance (NMR) -- determination of limonoid structure HPLC -- detection quantification Radioimmunoassay --detectionquantif. HPLC-MS -- detection quantification Distribution of limonin in Citrus fruit and vegetative tissues -- by Radioimmunoassay Limonin levels in fruit and vegetative tissue (White Marsh) High: Seeds Pith Lamella Albedo F