Classification Term: 1686

Limonoids (ontology term: CHEMONTID:0002380)

Highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17." [DOI:10.1016/0031-9422(92)90003-9, ISBN:9780412466205, PMID:16462017]

found 15 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Triterpenoids

Child Taxonomies: There is no child term of current ontology term.

Nomilin

(1S,3AS,4AR,4BR,6AR,11S,11AR,11BR,13AS)-11-(ACETYLOXY)-1-(3-FURANYL)DECAHYDRO-4B,7,7,11A,13A-PENTAMETHYLOXIRENO(4,4A)-2-BENZOPYRAN(6,5-G)(2)BENZOXEPIN-3,5,9(3AH,4BH,6H)-TRIONE

C28H34O9 (514.2202714)


Nomilin is a limonoid. 1-(Acetyloxy)-1,2-dihydroobacunoic acid e-lactone is a natural product found in Citrus latipes, Citrus hystrix, and other organisms with data available. Constituent of grapefruit (Citrus paradisi). Nomilin is found in lemon, sweet orange, and citrus. Nomilin is found in citrus. Nomilin is a constituent of grapefruit (Citrus paradisi) Nomilin is a limonoid compound obtained from the extracts of citrus fruits. Nomilin is an anti-obesity and anti-hyperglycemic agent [1][2]. Nomilin is a limonoid compound obtained from the extracts of citrus fruits. Nomilin is an anti-obesity and anti-hyperglycemic agent [1][2].

   

Linonin

11H,13H-Oxireno(d)pyrano(4,3:3,3a)isobenzofuro(5,4-f)(2)benzopyran-4,6,13(2H,5aH)-trione, 8-(3-furanyl)decahydro-2,2,4a,8a-tetramethyl-, (2aR-(2aalpha,4abeta,4bR,5aalpha,8alpha,8aalpha,10aalpha,10bR*,14aalpha))-

C26H30O8 (470.194058)


Linonin, also known as 7,16-dioxo-7,16-dideoxylimondiol or evodin, is a member of the class of compounds known as limonoids. Limonoids are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Linonin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Linonin can be found in lemon, which makes linonin a potential biomarker for the consumption of this food product. Limonin is a limonoid, an epoxide, a hexacyclic triterpenoid, a member of furans, an organic heterohexacyclic compound and a lactone. It has a role as a metabolite, an inhibitor and a volatile oil component. Limonin is a natural product found in Citrus tankan, Flacourtia jangomas, and other organisms with data available. Limonin is a triterpenoid compound rich in citrus fruits that has antiviral and antitumor activities. Limonin is a triterpenoid compound rich in citrus fruits that has antiviral and antitumor activities.

   

Obacunone

Oxireno(4,4a)-2-benzopyrano(6,5-g)(2)benzoxepin-3,5,9(3aH,4bH,6H)-trione, 1-(3-furanyl)-1,6a,7,11a,11b,12,13,13a-octahydro-4b,7,7,11a,13a-pentamethyl-, (1S,3aS,4aR,4bR,6aR,11aR,11bR,11bR,13aS)-

C26H30O7 (454.199143)


Constituent of Citrus subspecies, Fortunella margarita (oval kumquat) and Casimiroa edulis (Mexican apple). Obacunone is found in many foods, some of which are pomes, sweet orange, lemon, and fruits. Obacunone is found in fruits. Obacunone is a constituent of Citrus species, Fortunella margarita (oval kumquat) and Casimiroa edulis (Mexican apple) Obacunone is a limonoid. Obacunone is a natural product found in Limonia acidissima, Citrus latipes, and other organisms with data available. Obacunone, isolated from Citrus fruits, exhibits anti-tumor activity by the induction of apoptosis[1]. Obacunone, isolated from Citrus fruits, exhibits anti-tumor activity by the induction of apoptosis[1].

   

Linalool (8-hydroxydihydro-)

(1R,2R,2R,3S,5S,7R,10R,13S)-5-[(R)-(furan-3-yl)({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,7,11,11-tetramethyl-8,15-dioxo-12,16-dioxaspiro[oxirane-2,6-tetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadecane]-3-carboxylic acid

C32H42O14 (650.2574432)


   

Zapoterin

7-(furan-3-yl)-10-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-ene-5,15,20-trione

C26H30O8 (470.194058)


Zapoterin is found in pomes. Zapoterin is a constituent of the seeds of Casimiroa edulis (Mexican apple) Constituent of the seeds of Casimiroa edulis (Mexican apple). Zapoterin is found in pomes.

   

Limonoate a-ring-lactone

(1R,2R,2R,3S,5S,7R,10R,13S)-5-[(R)-(furan-3-yl)(hydroxy)methyl]-5,7,11,11-tetramethyl-8,15-dioxo-12,16-dioxaspiro[oxirane-2,6-tetracyclo[8.7.0.0¹,¹³.0²,⁷]heptadecane]-3-carboxylic acid

C26H32O9 (488.2046222)


Limonoate a-ring-lactone is a member of the class of compounds known as limonoids. Limonoids are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Limonoate a-ring-lactone is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Limonoate a-ring-lactone can be found in lemon and sweet orange, which makes limonoate a-ring-lactone a potential biomarker for the consumption of these food products.

   

Limonin

19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

C26H30O8 (470.194058)


Limonin is found in citrus. Limonin is isolated from oranges and other citrus fruits (Citrus species). Limonin is a limonoid, and a bitter, white, crystalline substance found in orange and lemon seeds. 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 Isolated from oranges and other citrus fruits (Citrus subspecies). Limonin is a triterpenoid compound rich in citrus fruits that has antiviral and antitumor activities. Limonin is a triterpenoid compound rich in citrus fruits that has antiviral and antitumor activities.

   

Limonexic acid

19-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione

C26H30O10 (502.183888)


Constituent of Citrus subspecies Limonexic acid is found in sweet orange and citrus. Limonexic acid is found in citrus. Limonexic acid is a constituent of Citrus species

   

Deacetylnomilin

7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione

C26H32O8 (472.20970719999997)


Isolated from orange (Citrus sinensis) and finger lime (Microcitrus australasica). Deacetylnomilin is found in lemon, sweet orange, and citrus. Deacetylnomilin is found in citrus. Deacetylnomilin is isolated from orange (Citrus sinensis) and finger lime (Microcitrus australasica

   

Nimbolide

Methyl 2-[6-(furan-3-yl)-7,9,11,15-tetramethyl-12,16-dioxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetic acid

C27H30O7 (466.199143)


Nimbolide is a triterpene derived from the leaves and flowers of neem (Azadirachta indica). Nimbolide induces apoptosis through inactivation of NF-κB. Nimbolide inhibits CDK4/CDK6 kinase activity. Nimbolide suppresses the NF-κB, Wnt, PI3K-Akt, MAPK and JAK-STAT signaling pathways[1].

   

Antibiotic 205t3

methyl 23-(dimethylamino)-4,8,12,22,24-pentahydroxy-1,12-dimethyl-6,17-dioxo-10-[(3,4,5-trimethoxy-4,6-dimethyloxan-2-yl)oxy]-20,25-dioxahexacyclo[19.3.1.0²,¹⁹.0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴]pentacosa-2,4,7(16),8,14,18-hexaene-13-carboxylate

C39H49NO16 (787.3051194)


D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D007364 - Intercalating Agents D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors D000970 - Antineoplastic Agents

   

Perforin A

9,19,20-Tris(acetyloxy)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icos-13-en-10-yl acetic acid

C34H40O14 (672.241794)


   

Salannin

14-(Acetyloxy)-6-(furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 2-methylbut-2-enoic acid

C34H44O9 (596.2985174)


   

Toosendanin

21-(acetyloxy)-6-(furan-3-yl)-12,16,19-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-4-yl acetate

C30H38O11 (574.2413998)


Toosendanin, a triterpenoid extracted from the bark of fruit of Melia toosendan Sieb. et Zucc., possesses analgesic, insecticidal and anti-inflammatory activities[1]. Toosendanin, a triterpenoid extracted from the bark of fruit of Melia toosendan Sieb. et Zucc., possesses analgesic, insecticidal and anti-inflammatory activities[1].

   

Obacunone 17-O-beta-D-glucoside

9-[furan-3-yl({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl]-5,5,7a,9,11b-pentamethyl-3,7-dioxo-5,5a,6,7,7a,9,10,11,11a,11b-decahydro-3H-spiro[naphtho[2,1-c]oxepine-8,2-oxirane]-3-carboxylic acid

C32H42O13 (634.2625282)


Obacunone 17-o-beta-d-glucoside is a member of the class of compounds known as limonoids. Limonoids are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Obacunone 17-o-beta-d-glucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Obacunone 17-o-beta-d-glucoside can be found in lemon, mandarin orange (clementine, tangerine), and sweet orange, which makes obacunone 17-o-beta-d-glucoside a potential biomarker for the consumption of these food products.