Biochemistry of Citrus Limonoids. Metabolism and Biological Functions.

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... To date, 36 types of aglycones and 17 types of glycosides have been identified mainly in citrus fruits of the family Rutaceae, which is composed of 160 genera and about 2,070 species [13]. The first study of the physiological effects of Citrus limonoids reported inhibitory effects on the eating behaviors of armyworms and predatory insects [14]. Strong inhibitory effects on eating were subsequently observed in termites. ...
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This section is focused on the physiological functions of yuzu (Citrus junos) to improve health. The modern lifestyle involves number of modern lifestyles involve various factors that may increase the production of active oxygen species. Nutritional supplements and medicines are commonly utilized to maintain health. Yuzu seeds contain >100-fold the limonoid content of grapefruit seeds and are rich in polyamines (PAs), including putrescine, spermidine, and spermine. Limonoid components mediate the antioxidant properties of citrus. Limonoids and PAs convey various bioactivities. PAs are closely associated with maintaining the function of the intestinal mucosal barrier, which might be involved in the metabolic processes of indigenous intestinal bacteria and in the health of the host. After ingestion, food is digested and absorbed in the intestinal tract, which is also responsible for immune responses against food antigens and intestinal bacteria. Detailed investigations of the physiological functions of extracted yuzu seed extracts may help to develop new treatment strategies against diseases associated with inflammatory responses.
... This suggests that CitLGT gene has certainly a regulatory role in LG accumulation and reducing the bitterness in fruit tissues of citrus especially in navel orange (29). In contrast to these studies, i.e. despite to the high transcription of CitLGT mRNA in flower and fruit of navel orange at young stage (40 DAF), LG was not detected probably because of high glucosidase activity (30). In lemon, LG Please note that this is an unedited version of the manuscript that has been accepted for publication. ...
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Kinnow mandarin (Citrus reticulata Blanco) is a popular citrus crop of northwestern India and it occupies maximum fruit area in Punjab. However, citrus juice processing industry is still suffering from delayed bitterness problem caused mainly by limonoid aglycones such as limonin. In order to study citrus limonoid metabolism, limonoid glucosyltransferase (LGT) gene, which encodes a natural debittering enzyme, was isolated from the fruit tissues of Kinnow mandarin. After confirmation and characterization, its full-length gene sequence (1533 bp) was submitted to National Centre for Biotechnology Information. Citrus reticulata limonoid glucosyltransferase (CrLGT) occupies a position on an independent branch in the largest subgroup and is phylogenetically different from those in other mandarin species like C. unshiu, showing its uniqueness in several features. The transcript expression of CrLGT, evaluated in different tissues such as young leaf, flavedo, albedo, sac covering and seed of Kinnow mandarin during early (90 days after flowering (DAF)), mid (150-210 DAF) and late (240 DAF) fruit developmental stages using semi-quantitative method, showed the highest expression in flavedo. Thus, it was concluded that the isolated LGT gene has an effect on limonoid metabolic engineering in citrus. Overexpression of this gene can reduce the delayed bitterness problem in citrus juice and enhance the accumulation of specific glucosides that have anticancer effects.
... Yuzu seeds can provide over 100 times the amount of limonoids found in grapefruit seed in commercial production (Minamisawa et al., 2014). The first study of the physiological effects of citrus limonoids reported inhibitory effects on eating in the case of armyworms and predatory insects (Hasegawa & Ifuku, 1994). Strong inhibitory effects on eating were subsequently observed in termites. ...
We determined high concentrations of arginine and polyamines (putrescine, spermidine, and spermine) in yuzu (Citrus junos) seeds. Yuzu produces large quantities of limonoids. We fed limonoid aglycones extracted from yuzu seeds and commercial spermine as a polyamine to Sandhoff disease (SD) mice with abnormal glycolipid metabolism and autosomal recessive inheritance, as found in humans. Ingestion of limonoid aglycones and spermine by SD mice extended their longevity by about 10–12%, where it alleviated inflammation of the central nervous system. After administering limonoid aglycones or limonoid aglycones/spermine, analyses of the bacterial flora in the feces based on 16S rDNA indicated changes in the relative ratio between Bacteroidetes (Bacteroidales and Lactobacillus) and Firmicutes (Clostridiales and Erysipelotrichaceae). In both SD and wild-type mice, the amount of short-chain fatty acids produced by the bacterial flora increased according to the intake of limonoid aglycones and spermine.
The limonoids of the seeds and the flavonoids of the leaves of a number of species of the Citrus sub-genus Papeda were examined. The seeds contained only the normal citrus limonoids and did not contain ichangensin, the unique limonoid found in C. ichangensis. A flavonoid analysis showed that a number of papeda varieties including C. latipes and C. hystrix may be a papeda hybrid species. C. junos had flavanone neoheperidosides, which are also found in cultivars related to the pummelo. All papedas examined had rutin present, which is characteristic of cultivars related to the citron. Citrus ichangensis had the most complex flavone/flavonol pattern of all the papedas examined. This suggests that Citrus ichangensis may truly be a unique papeda species unlike that of the other papedas.
We isolated a cDNA clone encoding limonoid UDP-glucosyltransferase (limonoid GTase) from the albedo of Satsuma mandarin (Citrus unshiu Marc.) and investigated the contribution to limonoid glucoside accumulation in fruit. The isolated cDNA clone (CitLGT) was 1732 bp in length encoding 511 deduced amino acids with a predicted molecular mass of 57.5 kDa. The products of in vitro translation from an expression vector had the limonoid GTase activity. Southern blot analysis of genomic DNA indicated that CitLGT was present as a single copy gene in the Citrus genome. The amount of transcript corresponding to CitLGT mRNA changed the same way as the fluctuation of limonin glucoside content during fruit development of navel orange (Citrus sinensis Osb.). This indicates that the transcription of CitLGT regulates the conversion of limonoid aglycones to glucosides in citrus fruit.
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