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Brief Introduction to Citrus Limonoids

Jiaxing Li TAMU-College Station TAMUK-Citrus Center

species related to pumello • Cause 2. The flavonoids e. The limonoids e. naringin-.Bitterness problem in citrus industry • Cause 1.g.g. limonin .

Limonoid aglycones (LA) -.17 isolated .Citrus & related genera • Tow forms in citrus: 1.>50 isolated from the Rutaceae (36 from Citrus&related genera) 2.Biochemistry of Limonoids in Citrus • A group of highly oxygenated tetracyclic triterpenoids -. Limonoid glucosides (LG) -.

LA: bitter. insoluble in water 2. LA glucosidated to LG--fruit maturation --.Biochemistry Cont. • Relation between LA and LG 1. LG: non-bitter. water-soluble 3.Occurs only in fruit tissues and seeds .Natural Debittering process --.

5 • Limonoid D-ring lactone hydrolase • Closed D-ring is the key structure .Delayed bitterness • PH<6.

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. 7α-acetate limonoid • Biosynthetic pathways of each group of these limonoids have been elucidated . Calamin group 3. Ichangensin group 4.

Example of Biosynthetic pathways: limonin group .

detection& quantification .Analytical Methods of Citrus Limonoids • Thin-layer chromatography (TLC) -. • HPLC-MS -.detection & quantification • Radioimmunoassay --detection&quantif.determination of limonoid structure • HPLC -.for limonoid detection • Nuclear Magnetic Resonance (NMR) -.

Distribution of limonin in Citrus fruit and vegetative tissues Radioimmunoassay • Limonin levels in fruit and vegetative tissue (White Marsh) High: Seeds Pith Lamella Albedo Flavedo Low: Juice vesicles .

Limonin distribution within grapefruit leaves • More concentrated in areas adjacent to the conductive tissues • flushing leaves > mature leaves .

to inhibit formation of chemicallyinduced neoplasia in forestomach. inhibit the proliferation of breast cancer cells in culture .Biological activities of citrus limonoids • Inducers of GST. a detoxifying enzyme in mice and rats: -. -. skin and oral of lab animals. small intestine. lung.

Biological activities contd. • • • • Antifeedant activity insect repellents growth disrupters reproduction inhibitors .

Different compounds are responsible for identical functions in different species. . 3.Limonoids and the Taxonomic Studies of Citrus • Theoretical bases 1. Plants have incorporated many secondary metabolites into specialized physiological functions such as reproduction and intracelluar signaling 2. secondary metabolites are often functionally unique at the species level.

Different Limonoid groups and the Chemotaxonomy of the true-citrus tree species and hybrids .

Future research • Nutritional research: determination of the roles phytochemicals play in the long term health of humans. -.Food additives for cancer prevention .

The End • Thank You • References Mark A. Berhow. Shin Hasegwa. Manners. .Citrus Limonoids -. American Chemical Society.Functional Chemicals in Agriculture and Food/ 2000. and Gary D.