The Bitter Principles of Citrus Fruit. I. Isolation of Nomilin, a New Bitter Principle from the Seeds of Oranges and Lemons

Emerson, Oliver H.

doi:10.1021/ja01182a034

Cited by 45 publications

(17 citation statements)

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“…At the time of its early isolation from orange seeds, deacetylnomilin (4) was erroneously considered as an isomer of limonin (1) and called isolimonin [130,131]. Indeed, 4 may be considered as the formal product of reductive cleavage of the A ring lactone of 1 and subsequent isomerization of the so-obtained carboxylic acid (isoobacunoic acid, 9) to give a β-hydroxy-ε-lactone ring (4-hydroxyoxepin-2-one) in lieu of the tetrahydrofuran one.…”

Section: Deacetylnomilin (4)mentioning

confidence: 99%

“…In 2001, Gai et al reported on the isolation of "a new compound" from Evodia rutaecarpa, 21-(R and S)-hydroxy-23-oxo-20-en-limonin, and named it shihulimonin A (Shihu is a word frequently found in the Chinese folk medicine but is commonly related to Dendrobium genus) [135]. Indeed 5 was early isolated by Emerson and generally referred to as 'Emerson's substance X' [131]. The agreeing works of several research groups [136][137][138] definitively demonstrated that 5 has the structure reported in Figure 1 while 6 is the 23-hydroxy, 21-oxo isomer of 5, notwithstanding contrasting literature graphics [25,28,118,120].…”

Section: Deacetylnomilin (4)mentioning

confidence: 99%

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The Chemistry and Pharmacology of Citrus Limonoids

et al. 2016

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Citrus limonoids (CLs) are a group of highly oxygenated terpenoid secondary metabolites found mostly in the seeds, fruits and peel tissues of citrus fruits such as lemons, limes, oranges, pumellos, grapefruits, bergamots, and mandarins. Represented by limonin, the aglycones and glycosides of CLs have shown to display numerous pharmacological activities including anticancer, antimicrobial, antioxidant, antidiabetic and insecticidal among others. In this review, the chemistry and pharmacology of CLs are systematically scrutinised through the use of medicinal chemistry tools and structure-activity relationship approach. Synthetic derivatives and other structurally-related limonoids from other sources are include in the analysis. With the focus on literature in the past decade, the chemical classification of CLs, their physico-chemical properties as drugs, their biosynthesis and enzymatic modifications, possible ways of enhancing their biological activities through structural modifications, their ligand efficiency metrics and systematic graphical radar plot analysis to assess their developability as drugs are among those discussed in detail.

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Section: Deacetylnomilin (4)mentioning

confidence: 99%

Section: Deacetylnomilin (4)mentioning

confidence: 99%

The Chemistry and Pharmacology of Citrus Limonoids

et al. 2016

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“…A white precipitate appeared when the concentrated solution was acidified to pH 1.0 with 4M HCl, and it was subsequently collected through centrifugation at 5000 r/min for 15 minutes. (c) Crystallisation: the obtained precipitate was dissolved in a mixed solution of dichloromethane/isopropanol (1:3, v/v), and was then kept at 4°C for 2 h (Emerson 1948). The limonin crystals obtained were dried at 60°C, and analysed by IR and HPLC.…”

Section: Methodsmentioning

confidence: 99%

Aqueous extraction of limonin from Citrus reticulate Blanco

Liu¹,

Liu²,

Rong³

et al. 2012

Czech J. Food Sci.

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The replacement of organic solutions in the extraction of limonin from citrus seeds with an alkaline solution was investigated. This method was based on the reversible conversion of limonin to limonoate A-ring lactone via ring-opening of D-ring lactone at different pH values. The extraction conditions, optimised using Taguchi experimental design, were as follows: pH 11, temperature 70°C, alkaline solution/seeds ratio 20:1 (v/w), ultrasonic power 800 W for 30 minutes. A yield of 7.5 mg/g (limonin/citrus seeds) of 98% pure limonin was obtained.  

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“…Limonin (Figure 1), also known as obaculactone and evodin, is a type of secondary metabolites belonging to the tetracyclic triterpenoids, which is usually found in the plants of Rutaceae and Meliaceae. Limonin is extensively distributed in citrus fruits, which is the main cause of citrus bitterness (Emerson, 1948). Limonin has broad‐spectrum biological activities, such as anticancer, antiviral, antioxidant, antimicrobial, anti‐inflammatory, anti‐obesity, liver protection, and anti‐atherosclerosis (Higby, 1938, Emerson, 1948, Kelley et al., 2015; Lee et al., 2016; Yang et al., 2014).…”

Section: Introductionmentioning

confidence: 99%

Limonin induces apoptosis of HL‐60 cells by inhibiting NQO1 activity

Chen

Liang

et al. 2021

Food Science & Nutrition

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Limonin is an important bioactive substance in citrus fruits, especially in seeds, which has great potential in cancer prevention and treatment. In order to explore the anticancer activity based on interaction between limonin and NQO1, Human promyelocytic leukemia cells (HL‐60) were studied in vitro. We found that limonin could inhibit proliferation and promote apoptosis of HL‐60 cells, and the effect was positively correlated with its dosage. Western blot results showed that limonin could activate the endogenous apoptosis pathway mediated by mitochondria via up‐regulating pro‐apoptotic proteins (Bax, cytochrome c, Caspase3, and Caspase9) and down‐regulating anti‐apoptotic proteins (Bcl‐2), thus inhibiting the proliferation of HL‐60 cells and promoting apoptosis, which further proved the anticancer activity of limonin from the molecular mechanism. At the same time, limonin down‐regulated the expression of NQO1, indicating that limonin may indirectly act on the apoptosis pathway by regulating the expression activity of antioxidant enzymes in vivo, thus exerting its inhibitory effect on tumor cells, which provides an idea for the molecular mechanism that natural products can indirectly exert their anticancer effect by regulating the activity of antioxidant enzymes.

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The Bitter Principles of Citrus Fruit. I. Isolation of Nomilin, a New Bitter Principle from the Seeds of Oranges and Lemons

Cited by 45 publications

References 0 publications

The Chemistry and Pharmacology of Citrus Limonoids

The Chemistry and Pharmacology of Citrus Limonoids

Aqueous extraction of limonin from Citrus reticulate Blanco

Limonin induces apoptosis of HL‐60 cells by inhibiting NQO1 activity

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