Limonin

Limonin
Names
	IUPAC name 7,16-Dioxo-7,16-dideoxylimondiol
	Other names limonoate D-ring-lactone,; limonoic acid di-delta-lactone
Identifiers
CAS Number	1180-71-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16226 ;
ChEMBL	ChEMBL517449 ;
ChemSpider	156367 ;
ECHA InfoCard	100.236.039
PubChem CID	179651;
UNII	L0F260866S ;
CompTox Dashboard (EPA)	DTXSID8045985 ;
	InChI InChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 Key: KBDSLGBFQAGHBE-MSGMIQHVSA-N ; InChI=1/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3/t14-,15-,17-,19-,20+,23-,24-,25+,26+/m0/s1 Key: KBDSLGBFQAGHBE-MSGMIQHVBF;
	SMILES O=C4[C@@]6(C)[C@@]72O[C@@H]7C(=O)O[C@@H](c1ccoc1)[C@]2(C)CC[C@@H]6[C@]35COC(=O)C[C@@H]5OC([C@@H]3C4)(C)C;
Properties
Chemical formula	C26H30O8
Molar mass	470.52 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Limonin is a limonoid, and a bitter, white, crystalline substance found in citrus and other plants. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.

Sources

Limonin is enriched in citrus fruits and is often found at higher concentrations in seeds, for example orange and lemon seeds. Limonin is present in plants such as those of the Dictamnus genus.^[1]

Presence in citrus products

Limonin and other limonoid compounds contribute to the bitter taste of some citrus food products. Researchers have proposed removal of limonoids from orange juice and other products (known as "debittering") through the use of polymeric films.^[2]

Bioactivity and research

Ongoing research programs are examining the effects of limonin in human diseases. Citrus seed extracts reportedly have antiviral properties, inhibiting replication of retroviruses like HIV-1 and HTLV-I.^[3] Neuroprotective effects of limonin have also been described.^[1] Limonin reduces proliferation of colon cancer cells^[4] and has been tested as an anti-obesity agent in mice.^[5]

Limonin has been shown to be an inhibitor of p-glycoprotein, a cellular efflux pump.^[6]

References

^ ^a ^b Yoon, J. S.; Yang, H.; Kim, S. H.; Sung, S. H.; Kim, Y. C. (2010). "Limonoids from Dictamnus dasycarpus Protect Against Glutamate-induced Toxicity in Primary Cultured Rat Cortical Cells". Journal of Molecular Neuroscience. 42 (1): 9–16. doi:10.1007/s12031-010-9333-1. PMID 20155333.
^ Fayoux, S. P. C.; Hernandez, R. J.; Holland, R. V. (2007). "The Debittering of Navel Orange Juice Using Polymeric Films". Journal of Food Science. 72 (4): E143–E154. doi:10.1111/j.1750-3841.2007.00283.x. PMID 17995766.
^ Balestrieri, E.; Pizzimenti, F.; Ferlazzo, A.; Giofrè, S. V.; Iannazzo, D.; Piperno, A.; Romeo, R.; Chiacchio, M. A.; Mastino, A.; MacChi, B. (2011). "Antiviral activity of seed extract from Citrus bergamia towards human retroviruses". Bioorganic & Medicinal Chemistry. 19 (6): 2084–2089. doi:10.1016/j.bmc.2011.01.024. PMID 21334901.
^ Chidambara Murthy, K. N.; Jayaprakasha, G. K.; Kumar, V.; Rathore, K. S.; Patil, B. S. (2011). "Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis". Journal of Agricultural and Food Chemistry. 59 (6): 2314–2323. doi:10.1021/jf104498p. PMID 21338095.
^ Ono, E.; Inoue, J.; Hashidume, T.; Shimizu, M.; Sato, R. (2011). "Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet". Biochemical and Biophysical Research Communications. 410 (3): 677–681. doi:10.1016/j.bbrc.2011.06.055. PMID 21693102.
^ El-Readi, Mahmoud Zaki; Hamdan, Dalia; Farrag, Nawal; El-Shazly, Assem; Wink, Michael (January 2010). "Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines". European Journal of Pharmacology. 626 (2–3): 139–145. doi:10.1016/j.ejphar.2009.09.040.

External links

PubChem Compound Summary
"Citrus Compound: ready to help your body!" (Agricultural Research Service, USDA)

[Dictamnus-1] Yoon, J. S.; Yang, H.; Kim, S. H.; Sung, S. H.; Kim, Y. C. (2010). "Limonoids from Dictamnus dasycarpus Protect Against Glutamate-induced Toxicity in Primary Cultured Rat Cortical Cells". Journal of Molecular Neuroscience. 42 (1): 9–16. doi:10.1007/s12031-010-9333-1. PMID 20155333.

[2] Fayoux, S. P. C.; Hernandez, R. J.; Holland, R. V. (2007). "The Debittering of Navel Orange Juice Using Polymeric Films". Journal of Food Science. 72 (4): E143–E154. doi:10.1111/j.1750-3841.2007.00283.x. PMID 17995766.

[3] Balestrieri, E.; Pizzimenti, F.; Ferlazzo, A.; Giofrè, S. V.; Iannazzo, D.; Piperno, A.; Romeo, R.; Chiacchio, M. A.; Mastino, A.; MacChi, B. (2011). "Antiviral activity of seed extract from Citrus bergamia towards human retroviruses". Bioorganic & Medicinal Chemistry. 19 (6): 2084–2089. doi:10.1016/j.bmc.2011.01.024. PMID 21334901.

[4] Chidambara Murthy, K. N.; Jayaprakasha, G. K.; Kumar, V.; Rathore, K. S.; Patil, B. S. (2011). "Citrus Limonin and Its Glucoside Inhibit Colon Adenocarcinoma Cell Proliferation through Apoptosis". Journal of Agricultural and Food Chemistry. 59 (6): 2314–2323. doi:10.1021/jf104498p. PMID 21338095.

[5] Ono, E.; Inoue, J.; Hashidume, T.; Shimizu, M.; Sato, R. (2011). "Anti-obesity and anti-hyperglycemic effects of the dietary citrus limonoid nomilin in mice fed a high-fat diet". Biochemical and Biophysical Research Communications. 410 (3): 677–681. doi:10.1016/j.bbrc.2011.06.055. PMID 21693102.

[6] El-Readi, Mahmoud Zaki; Hamdan, Dalia; Farrag, Nawal; El-Shazly, Assem; Wink, Michael (January 2010). "Inhibition of P-glycoprotein activity by limonin and other secondary metabolites from Citrus species in human colon and leukaemia cell lines". European Journal of Pharmacology. 626 (2–3): 139–145. doi:10.1016/j.ejphar.2009.09.040.

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