Trigonelline (N'-methylnicotinate) (BioDeep_00000000769)

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite

代谢物信息卡片

Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt

化学式: C7H7NO2 (137.0476762)
中文名称: 葫芦巴碱, 三叶草碱
谱图信息: 最多检出来源 Homo sapiens(blood) 0.05%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Trigonelline (N'-methylnicotinate). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/trigonelline_(n_-methylnicotinate) (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000000769). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C[n+1](c1)cc(cc1)C([O-1])=O
InChI: InChI=1/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3

描述信息

Trigonelline, also known as caffearin or gynesine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. It is also found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. High amounts of trigonelline have been found in arabica coffee, fenugreeks, and common peas. Another foods such as yellow bell peppers, orange bellpeppers and muskmelons also contain trigonelline but in lower concentrations. Trigonelline has also been detected but not quantified in several different foods, such as rices, triticales, alfalfa, cereals and cereal products, and ryes. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products.
Alkaloid from fenugreek (Trigonella foenum-graecum) (Leguminosae), and very many other subspecies; also present in coffee beans and many animals. Trigonelline is an alkaloid with chemical formula C7H7NO2 and CAS number 535-83-1. It is found in coffee, where it may help to prevent dental caries by preventing the bacteria Streptococcus mutans from adhering to teeth.; Trigonelline is an alkaloid with chemical formula C7H7NO2. It is an inner salt formed by the addition of a methyl group to the nitrogen atom of niacin. Trigonelline is a product of the metabolism of niacin (vitamin B3) which is excreted in the urine. Trigonelline in the urine is a biomarker for the consumption of coffee, legumes and soy products.
N-methylnicotinate is an iminium betaine that is the conjugate base of N-methylnicotinic acid, arising from deprotonation of the carboxy group. It has a role as a plant metabolite, a food component and a human urinary metabolite. It is an iminium betaine and an alkaloid. It is functionally related to a nicotinate. It is a conjugate base of a N-methylnicotinic acid.
Trigonelline is a natural product found in Hypoestes phyllostachya, Schumanniophyton magnificum, and other organisms with data available.
See also: Fenugreek seed (part of).
Acquisition and generation of the data is financially supported in part by CREST/JST.
CONFIDENCE standard compound; ML_ID 52
KEIO_ID T060
Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis.
Trigonelline is an alkaloid with potential antidiabetic activity that can be isolated from Trigonella foenum-graecum L or Leonurus artemisia. Trigonelline is a potent Nrf2 inhibitor that blocks Nrf2-dependent proteasome activity, thereby enhancing apoptosis in pancreatic cancer cells. Trigonelline also has anti-HSV-1, antibacterial, and antifungal activity and induces ferroptosis.

同义名列表

55 个代谢物同义名

Pyridinium, 3-carboxy-1-methyl-, hydroxide, inner salt; 3-Carboxy-1-methylpyridinium, Hydroxide, Inner salt; 3-Carboxy-1-methylpyridinium hydroxide, inner salt; TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED) [DSC]; 3-carboxy-1-methyl-Pyridinium hydroxide inner salt; 3-Carboxy-1-methylpyridinium hydroxide inner salt; 5-22-02-00143 (Beilstein Handbook Reference); TRIGONELLINE (CONSTITUENT OF FENUGREEK SEED); 1-Methyl-Nicotinic Acid Anion(Trigonelline); Pyridinium, 3-carboxy-1-methyl-, inner salt; 3-Carboxy-1-methylpyridin-1-ium hydroxide; 1-methylpyridin-1-ium-3-carboxylic acid; 3-Carboxy-1-methylpyridinium inner salt; 1-Methyl-3-pyridiniumcarboxylic acid; 1-Methylpyridinio-3-carboxylic acid; 1-methylpyridin-1-ium-3-carboxylate; 1-methylpyridinium-3-carboxylate; 1-Methyl-3-pyridiniumcarboxylate; 1-Methylpyridinio-3-carboxylate; Nicotinic acid N-methylbetaine; N-Methylnicotinic acid betaine; WWNNZCOKKKDOPX-UHFFFAOYSA-N; Nicotinate N-methylbetaine; N-Methyl-nicotinic acid; Betaine nicotinic acid; N-Methylnicotinic acid; 1-Methylnicotinic acid; trigonelline tosylate; TRIGONELLINE [USP-RS]; Betain nicotinic acid; trigonelline chloride; TRIGONELLINE (USP-RS); trigonelline iodide; N-methyl-nicotinate; TRIGONELLINE [HSDB]; 1-methylnicotinate; N-Methylnicotinate; Betaine nicotinate; TRIGONELLINE [MI]; Betain nicotinate; Trigonelline,(S); trigonelline ion; UNII-3NQ9N60I00; Trigenelline; Trigenolline; Trigonelline; Trigonellin; Coffearine; Caffearine; 3NQ9N60I00; Coffearin; Caffearin; Gynesine; Trigonelline hydrochloride; Trigonelline

数据库引用编号

29 个数据库交叉引用编号

ChEBI: CHEBI:18123
KEGG: C01004
PubChem: 5570
HMDB: HMDB0000875
Metlin: METLIN273
ChEMBL: CHEMBL350675
Wikipedia: Trigonelline
MeSH: trigonelline
ChemIDplus: 0000535831
MetaCyc: METHYLNICOTINATE
KNApSAcK: C00001555
foodb: FDB002237
chemspider: 5369
CAS: 535-83-1
MoNA: PS102601
MoNA: PS102602
MoNA: ML005201
MoNA: KO004202
MoNA: KO004205
MoNA: PR100409
MoNA: PR100410
MoNA: KO004204
MoNA: KO004201
MoNA: KO004203
MoNA: PS102603
medchemexpress: HY-N0414
PMhub: MS000007667
NIKKAJI: J6.346K
RefMet: Trigonelline

分类词条

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

trigonelline biosynthesis: SAM + nicotinate ⟶ SAH + trigonelline

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

trigonelline biosynthesis: SAM + nicotinate ⟶ SAH + trigonelline
trigonelline biosynthesis: SAM + nicotinate ⟶ SAH + trigonelline

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

202 个相关的物种来源信息

3483 Cannabis sativa: 10.1021/NP50008A001
670328 Grona triflora: 10.1016/S0031-9422(00)97411-9
7227 Drosophila melanogaster: 10.1038/S41467-019-11933-Z
5691 Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
3702 Arabidopsis thaliana: 10.1104/PP.109.148031
49837 Retama raetam: 10.2307/4117899
13329 Achillea millefolium: 10.1007/BF02908196
282720 Achillea aspleniifolia: 10.1007/BF02908196
282770 Achillea virescens: 10.1007/BF02908196
183589 Pseudo-nitzschia multistriata: 10.3390/MD18060313
78534 Trigonella foenum-graecum: 10.1016/S0031-9422(00)83050-2
35128 Thalassiosira pseudonana: 10.1016/J.PROTIS.2019.05.004
2708974 Schumanniophyton problematicum: 10.1002/PCA.2800040103
114490 Schumanniophyton magnificum:
183298 Hibiscus rosa-sinensis: 10.1002/PTR.1628
183260 Hibiscus sabdariffa: 10.1002/PTR.1628
70838 Pterocladiella capillacea: 10.1021/NP50056A023
141992 Justicia spicigera: 10.1016/0031-9422(88)87029-8
141299 Dicliptera suberecta: 10.1016/0031-9422(88)87029-8
34260 Crossandra nilotica: 10.1016/0031-9422(88)87029-8
34262 Eranthemum pulchellum: 10.1016/0031-9422(88)87029-8
101678 Hypoestes phyllostachya: 10.1016/0031-9422(88)87029-8
76374 Pachystachys lutea: 10.1016/0031-9422(88)87029-8
504049 Thunbergia grandiflora: 10.1016/0031-9422(88)87029-8
13327 Acanthus montanus: 10.1016/0031-9422(88)87029-8
504047 Thunbergia fragrans: 10.1016/0031-9422(88)87029-8
139222 Thunbergia mysorensis: 10.1016/0031-9422(88)87029-8
1454542 Amaranthus graecizans: 10.1016/S0305-1978(98)00072-6
3567 Amaranthus caudatus: 10.1016/S0305-1978(98)00072-6
117272 Amaranthus cruentus: 10.1016/S0305-1978(98)00072-6
2613834 Amaranthus aureus: 10.1016/S0305-1978(98)00072-6
169208 Froelichia gracilis: 10.1016/S0305-1978(98)00072-6
221778 Gomphrena serrata: 10.1016/S0305-1978(98)00072-6
124761 Amaranthus blitoides: 10.1016/S0305-1978(98)00072-6
169210 Iresine herbstii: 10.1016/S0305-1978(98)00072-6
1167244 Alternanthera paronychioides: 10.1016/S0305-1978(98)00072-6
221762 Alternanthera sessilis: 10.1016/S0305-1978(98)00072-6
158579 Amaranthus powellii: 10.1016/S0305-1978(98)00072-6
29722 Amaranthus tricolor: 10.1016/S0305-1978(98)00072-6
3565 Amaranthus hybridus: 10.1016/S0305-1978(98)00072-6
124763 Amaranthus retroflexus: 10.1016/S0305-1978(98)00072-6
28502 Amaranthus hypochondriacus: 10.1016/S0305-1978(98)00072-6
46112 Celosia argentea: 10.1016/S0305-1978(98)00072-6
240037 Chamissoa altissima: 10.1016/S0305-1978(98)00072-6
240008 Aerva: 10.1016/S0305-1978(98)00072-6
217685 Iresine diffusa: 10.1016/S0305-1978(98)00072-6
124765 Amaranthus spinosus: 10.1016/S0305-1978(98)00072-6
3847 Glycine max:
159386 Nothapodytes nimmoniana:
13443 Coffea arabica:
241872 Castilla ulei: 10.1016/0031-9422(91)83194-P
681459 Maquira guianensis: 10.1016/0031-9422(91)83194-P
241907 Perebea mollis: 10.1016/0031-9422(91)83194-P
241915 Pseudolmedia laevigata: 10.1016/0031-9422(91)83194-P
1904798 Helicostylis elegans: 10.1016/0031-9422(91)83194-P
241916 Pseudolmedia laevis: 10.1016/0031-9422(91)83194-P
33153 Gnetum parvifolium:
2795856 Eusynstyela latericius: 10.1021/NP900099J
85810 Astrosclera willeyana: 10.1016/S0040-4039(97)00846-0
32198 Thunbergia alata: 10.1016/0031-9422(89)80280-8
150421 Panulirus cygnus: 10.1071/CH9810787
49390 Coffea canephora:
3816 Abrus precatorius:
3879 Medicago sativa: 10.1104/PP.99.4.1526
3888 Pisum sativum:
798309 Cymbastela cantharella: 10.1021/NP960562P
4577 Zea mays:
4550 Secale cereale:
3726 Raphanus sativus:
3661 Cucurbita maxima:
4679 Allium cepa:
3818 Arachis hypogaea:
3656 Cucumis melo:
3885 Phaseolus vulgaris:
3906 Vicia faba:
4513 Hordeum vulgare:
4565 Triticum aestivum:
4072 Capsicum annuum:
4111 Solanum melongena:
4236 Lactuca sativa:
3864 Lens culinaris:
3891 Psophocarpus tetragonolobus:
4560 Sorghum halepense:
49389 Coffea brevipes: 10.1016/0031-9422(91)83637-Z
49377 Coffea racemosa: 10.1016/0031-9422(91)83637-Z
49373 Coffea liberica: 10.1016/0031-9422(91)83637-Z
49383 Coffea stenophylla: 10.1016/0031-9422(91)83637-Z
49380 Coffea salvatrix: 10.1016/0031-9422(91)83637-Z
49387 Coffea travancorensis: 10.1016/0031-9422(91)83637-Z
185542 Ilex paraguariensis: 10.1016/0031-9422(91)83637-Z
213301 Coffea liberica var. dewevrei: 10.1016/0031-9422(91)83637-Z
413686 Bauhinia forficata: 10.1021/NP50029A028
47083 Melilotus officinalis: 10.1007/BF00628729
89585 Lemna aequinoctialis: 10.1271/BBB1961.53.2867
161103 Lemna perpusilla: 10.1271/BBB1961.53.2867
76396 Sesbania sesban: 10.1016/0031-9422(95)00064-E
47065 Astragalus sinicus: 10.1021/JO01198A013
3483 Cannabis sativa: 10.1021/NP50008A001
670328 Grona triflora: 10.1016/S0031-9422(00)97411-9
7227 Drosophila melanogaster: 10.1038/S41467-019-11933-Z
5691 Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
3702 Arabidopsis thaliana: 10.1104/PP.109.148031
49837 Retama raetam: 10.2307/4117899
13329 Achillea millefolium: 10.1007/BF02908196
282720 Achillea aspleniifolia: 10.1007/BF02908196
282770 Achillea virescens: 10.1007/BF02908196
183589 Pseudo-nitzschia multistriata: 10.3390/MD18060313
78534 Trigonella foenum-graecum: 10.1016/S0031-9422(00)83050-2
35128 Thalassiosira pseudonana: 10.1016/J.PROTIS.2019.05.004
2708974 Schumanniophyton problematicum: 10.1002/PCA.2800040103
114490 Schumanniophyton magnificum:
183298 Hibiscus rosa-sinensis: 10.1002/PTR.1628
183260 Hibiscus sabdariffa: 10.1002/PTR.1628
70838 Pterocladiella capillacea: 10.1021/NP50056A023
141992 Justicia spicigera: 10.1016/0031-9422(88)87029-8
141299 Dicliptera suberecta: 10.1016/0031-9422(88)87029-8
34260 Crossandra nilotica: 10.1016/0031-9422(88)87029-8
34262 Eranthemum pulchellum: 10.1016/0031-9422(88)87029-8
101678 Hypoestes phyllostachya: 10.1016/0031-9422(88)87029-8
76374 Pachystachys lutea: 10.1016/0031-9422(88)87029-8
504049 Thunbergia grandiflora: 10.1016/0031-9422(88)87029-8
13327 Acanthus montanus: 10.1016/0031-9422(88)87029-8
504047 Thunbergia fragrans: 10.1016/0031-9422(88)87029-8
139222 Thunbergia mysorensis: 10.1016/0031-9422(88)87029-8
1454542 Amaranthus graecizans: 10.1016/S0305-1978(98)00072-6
3567 Amaranthus caudatus: 10.1016/S0305-1978(98)00072-6
117272 Amaranthus cruentus: 10.1016/S0305-1978(98)00072-6
2613834 Amaranthus aureus: 10.1016/S0305-1978(98)00072-6
169208 Froelichia gracilis: 10.1016/S0305-1978(98)00072-6
221778 Gomphrena serrata: 10.1016/S0305-1978(98)00072-6
124761 Amaranthus blitoides: 10.1016/S0305-1978(98)00072-6
169210 Iresine herbstii: 10.1016/S0305-1978(98)00072-6
1167244 Alternanthera paronychioides: 10.1016/S0305-1978(98)00072-6
221762 Alternanthera sessilis: 10.1016/S0305-1978(98)00072-6
158579 Amaranthus powellii: 10.1016/S0305-1978(98)00072-6
29722 Amaranthus tricolor: 10.1016/S0305-1978(98)00072-6
3565 Amaranthus hybridus: 10.1016/S0305-1978(98)00072-6
124763 Amaranthus retroflexus: 10.1016/S0305-1978(98)00072-6
28502 Amaranthus hypochondriacus: 10.1016/S0305-1978(98)00072-6
46112 Celosia argentea: 10.1016/S0305-1978(98)00072-6
240037 Chamissoa altissima: 10.1016/S0305-1978(98)00072-6
240008 Aerva: 10.1016/S0305-1978(98)00072-6
217685 Iresine diffusa: 10.1016/S0305-1978(98)00072-6
124765 Amaranthus spinosus: 10.1016/S0305-1978(98)00072-6
3847 Glycine max:
159386 Nothapodytes nimmoniana:
13443 Coffea arabica:
241872 Castilla ulei: 10.1016/0031-9422(91)83194-P
681459 Maquira guianensis: 10.1016/0031-9422(91)83194-P
241907 Perebea mollis: 10.1016/0031-9422(91)83194-P
241915 Pseudolmedia laevigata: 10.1016/0031-9422(91)83194-P
1904798 Helicostylis elegans: 10.1016/0031-9422(91)83194-P
241916 Pseudolmedia laevis: 10.1016/0031-9422(91)83194-P
33153 Gnetum parvifolium:
2795856 Eusynstyela latericius: 10.1021/NP900099J
85810 Astrosclera willeyana: 10.1016/S0040-4039(97)00846-0
32198 Thunbergia alata: 10.1016/0031-9422(89)80280-8
150421 Panulirus cygnus: 10.1071/CH9810787
49390 Coffea canephora:
3816 Abrus precatorius:
3879 Medicago sativa: 10.1104/PP.99.4.1526
3888 Pisum sativum:
798309 Cymbastela cantharella: 10.1021/NP960562P
4577 Zea mays:
4550 Secale cereale:
3726 Raphanus sativus:
3661 Cucurbita maxima:
4679 Allium cepa:
3818 Arachis hypogaea:
3656 Cucumis melo:
3885 Phaseolus vulgaris:
3906 Vicia faba:
4513 Hordeum vulgare:
4565 Triticum aestivum:
4072 Capsicum annuum:
4111 Solanum melongena:
4236 Lactuca sativa:
3864 Lens culinaris:
3891 Psophocarpus tetragonolobus:
4560 Sorghum halepense:
49389 Coffea brevipes: 10.1016/0031-9422(91)83637-Z
49377 Coffea racemosa: 10.1016/0031-9422(91)83637-Z
49373 Coffea liberica: 10.1016/0031-9422(91)83637-Z
49383 Coffea stenophylla: 10.1016/0031-9422(91)83637-Z
49380 Coffea salvatrix: 10.1016/0031-9422(91)83637-Z
49387 Coffea travancorensis: 10.1016/0031-9422(91)83637-Z
185542 Ilex paraguariensis: 10.1016/0031-9422(91)83637-Z
213301 Coffea liberica var. dewevrei: 10.1016/0031-9422(91)83637-Z
413686 Bauhinia forficata: 10.1021/NP50029A028
47083 Melilotus officinalis: 10.1007/BF00628729
89585 Lemna aequinoctialis: 10.1271/BBB1961.53.2867
161103 Lemna perpusilla: 10.1271/BBB1961.53.2867
76396 Sesbania sesban: 10.1016/0031-9422(95)00064-E
47065 Astragalus sinicus: 10.1021/JO01198A013
9606 Homo sapiens: -
569774 金线莲: -
3483 Cannabis Sativa L.: -
714465 Dictamnus dasycarpus Turcz.: -
199225 Pinellia ternata (Thunb. )Breit.: -
78534 Trigonella foenum-graecum L.: -
3498 Morus alba L.: -
33090 Plants: -

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Menna S Zeyada, Salma M Eraky, Mamdouh M El-Shishtawy. Trigonelline mitigates bleomycin-induced pulmonary inflammation and fibrosis: Insight into NLRP3 inflammasome and SPHK1/S1P/Hippo signaling modulation. Life sciences. 2024 Jan; 336(?):122272. doi: 10.1016/j.lfs.2023.122272. [PMID: 37981228]
Minmin Gong, Yujin Guo, Hui Dong, Wenbin Wu, Fan Wu, Fuer Lu. Trigonelline inhibits tubular epithelial-mesenchymal transformation in diabetic kidney disease via targeting Smad7. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Dec; 168(?):115747. doi: 10.1016/j.biopha.2023.115747. [PMID: 37864898]
Sharmin Aktar, Farhana Ferdousi, Shinji Kondo, Tamami Kagawa, Hiroko Isoda. Transcriptomics and biochemical evidence of trigonelline ameliorating learning and memory decline in the senescence-accelerated mouse prone 8 (SAMP8) model by suppressing proinflammatory cytokines and elevating neurotransmitter release. GeroScience. 2023 Sep; ?(?):. doi: 10.1007/s11357-023-00919-x. [PMID: 37721682]
Nick Konstantinidis, Heike Franke, Steffen Schwarz, Dirk W Lachenmeier. Risk Assessment of Trigonelline in Coffee and Coffee By-Products. Molecules (Basel, Switzerland). 2023 Apr; 28(8):. doi: 10.3390/molecules28083460. [PMID: 37110693]
Youdan Liang, Xiaolin Dai, Yi Cao, Xian Wang, Jing Lu, Long Xie, Kai Liu, Xiaofang Li. The neuroprotective and antidiabetic effects of trigonelline: A review of signaling pathways and molecular mechanisms. Biochimie. 2023 Mar; 206(?):93-104. doi: 10.1016/j.biochi.2022.10.009. [PMID: 36257493]
M A Hamzawy, A M Abo-Youssef, M N Malak, M M Khalaf. Multiple targets of Nrf 2 inhibitor; trigonelline in combating urethane-induced lung cancer by caspase-executioner apoptosis, cGMP and limitation of cyclin D1 and Bcl2. European review for medical and pharmacological sciences. 2022 12; 26(24):9393-9408. doi: 10.26355/eurrev_202212_30690. [PMID: 36591848]
Moein Masjedi, Aida Solhjoo. Does trigonelline help skin tone? Molecular docking studies of trigonelline on the human tyrosinase, formulation, optimization, and characterization of an emulgel-containing Trigonella foenum-graecum L. fenugreek standardized hydroalcoholic extract. Journal of cosmetic dermatology. 2022 Dec; 21(12):7178-7193. doi: 10.1111/jocd.15453. [PMID: 36217567]
Paleerath Peerapen, Wanida Boonmark, Visith Thongboonkerd. Trigonelline prevents kidney stone formation processes by inhibiting calcium oxalate crystallization, growth and crystal-cell adhesion, and downregulating crystal receptors. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 May; 149(?):112876. doi: 10.1016/j.biopha.2022.112876. [PMID: 35367760]
Geetika Wadhwa, Kowthavarapu Venkata Krishna, Rajeev Taliyan, Neeraj Tandon, Satyapal Singh Yadav, Dipankar Banerjee, Avinash Narwaria, Chandrakant Katiyar, Sunil Kumar Dubey. A novel UPLC-MS/MS method for simultaneous quantification of trigonelline, 4-hydroxyisoleucine, and diosgenin from Trigonella foenum-graecum extract: Application to pharmacokinetic study in healthy and type 2 diabetic rats. Biomedical chromatography : BMC. 2022 Feb; 36(2):e5275. doi: 10.1002/bmc.5275. [PMID: 34738247]
Weijie Zou, Shuang Yang, Li Chen, Su Hu, Guangyu Hao, Chunhong Hu. Iodixanol activation of mast cells: Implications in the pathogenesis of iodixanol-induced delayed cutaneous adverse reactions. Toxicology. 2022 01; 465(?):153034. doi: 10.1016/j.tox.2021.153034. [PMID: 34774977]
Gustavo Galo Marcheafave, Cláudia Domiciano Tormena, Amelia Elena Terrile, Carlos Alberto Rossi Salamanca-Neto, Elen Romão Sartori, Miroslava Rakocevic, Roy Edward Bruns, Ieda Spacino Scarminio, Elis Daiane Pauli. Ecometabolic mixture design-fingerprints from exploratory multi-block data analysis in Coffea arabica beans from climate changes: Elevated carbon dioxide and reduced soil water availability. Food chemistry. 2021 Nov; 362(?):129716. doi: 10.1016/j.foodchem.2021.129716. [PMID: 34006394]
Nuntouchaporn Hutachok, Pimpisid Koonyosying, Tanachai Pankasemsuk, Pongsak Angkasith, Chaiwat Chumpun, Suthat Fucharoen, Somdet Srichairatanakool. Chemical Analysis, Toxicity Study, and Free-Radical Scavenging and Iron-Binding Assays Involving Coffee (Coffea arabica) Extracts. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144169. [PMID: 34299444]
Lone A Nazir, Malik A Tanveer, Sheikh A Umar, Sharma Love, Gupta Divya, Sheikh A Tasduq. Inhibition of Ultraviolet-B Radiation Induced Photodamage by Trigonelline Through Modulation of Mitogen Activating Protein Kinases and Nuclear Factor-κB Signaling Axis in Skin. Photochemistry and photobiology. 2021 07; 97(4):785-794. doi: 10.1111/php.13369. [PMID: 33345344]
Neda Mohamadi, Fariba Sharififar, Mehdi Ansari, Mostafa Pournamdari, Mahdieh Rezaei, Navid Hassanabadi. Pharmacokinetic profile of diosgenin and trigonelline following intravenous and oral administration of fenugreek seed extract and pure compound in rabbit. Journal of Asian natural products research. 2021 May; 23(5):466-477. doi: 10.1080/10286020.2020.1769609. [PMID: 32447972]
Maria Alessia Schouten, Silvia Tappi, Simone Angeloni, Manuela Cortese, Giovanni Caprioli, Sauro Vittori, Santina Romani. Acrylamide formation and antioxidant activity in coffee during roasting - A systematic study. Food chemistry. 2021 May; 343(?):128514. doi: 10.1016/j.foodchem.2020.128514. [PMID: 33187741]
Minji Choi, Sulagna Mukherjee, Jong Won Yun. Trigonelline induces browning in 3T3-L1 white adipocytes. Phytotherapy research : PTR. 2021 Feb; 35(2):1113-1124. doi: 10.1002/ptr.6892. [PMID: 33015893]
Neda Mohamadi, Fariba Sharififar, Mostafa Pournamdari, Mehdi Ansari. Determination of trigonelline in human plasma by magnetic solid-phase extraction: a pharmacokinetic study. Nanomedicine (London, England). 2021 02; 16(4):323-333. doi: 10.2217/nnm-2020-0365. [PMID: 33501838]
Flávia de Abreu Pinheiro, Luzia Ferreira Elias, Milton de Jesus Filho, Mariana Uliana Modolo, Juliana de Cássia Gomes Rocha, Mayara Fumiere Lemos, Rodrigo Scherer, Wilton Soares Cardoso. Arabica and Conilon coffee flowers: Bioactive compounds and antioxidant capacity under different processes. Food chemistry. 2021 Jan; 336(?):127701. doi: 10.1016/j.foodchem.2020.127701. [PMID: 32781354]
Wen-Yu Zeng, Lin Tan, Cong Han, Zhuo-Ya Zheng, Gui-Sheng Wu, Huai-Rong Luo, Su-Lian Li. Trigonelline Extends the Lifespan of C. Elegans and Delays the Progression of Age-Related Diseases by Activating AMPK, DAF-16, and HSF-1. Oxidative medicine and cellular longevity. 2021; 2021(?):7656834. doi: 10.1155/2021/7656834. [PMID: 34616504]
Grace F Crotty, Romeo Maciuca, Eric A Macklin, Junhua Wang, Manuel Montalban, Sonnet S Davis, Jamal I Alkabsh, Rachit Bakshi, Xiqun Chen, Alberto Ascherio, Giuseppe Astarita, Sarah Huntwork-Rodriguez, Michael A Schwarzschild. Association of caffeine and related analytes with resistance to Parkinson disease among LRRK2 mutation carriers: A metabolomic study. Neurology. 2020 12; 95(24):e3428-e3437. doi: 10.1212/wnl.0000000000010863. [PMID: 32999056]
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Taehoon Lee, Hyesung Park, Pradeep Puligundla, Gwi-Hee Koh, Jungro Yoon, Chulkyoon Mok. Degradation of benzopyrene and acrylamide in roasted coffee beans by corona discharge plasma jet (CDPJ) and its effects on biochemical and sensory properties. Food chemistry. 2020 Oct; 328(?):127117. doi: 10.1016/j.foodchem.2020.127117. [PMID: 32474240]
Mai M Farid, Ximeng Yang, Tomoharu Kuboyama, Chihiro Tohda. Trigonelline recovers memory function in Alzheimer's disease model mice: evidence of brain penetration and target molecule. Scientific reports. 2020 10; 10(1):16424. doi: 10.1038/s41598-020-73514-1. [PMID: 33009465]
Juliana dePaula, Sara C Cunha, Ildi Revi, Alessandro M Batista, Soraia V M D Sá, Veronica Calado, José O Fernandes, Adriano Cruz, Adriana Farah. Contents of key bioactive and detrimental compounds in health performance coffees compared to conventional types of coffees sold in the United States market. Food & function. 2020 Sep; 11(9):7561-7575. doi: 10.1039/d0fo01674h. [PMID: 32820768]
Letizia Bresciani, Michele Tassotti, Alice Rosi, Daniela Martini, Monica Antonini, Alessandra Dei Cas, Riccardo Bonadonna, Furio Brighenti, Daniele Del Rio, Pedro Mena. Absorption, Pharmacokinetics, and Urinary Excretion of Pyridines After Consumption of Coffee and Cocoa-Based Products Containing Coffee in a Repeated Dose, Crossover Human Intervention Study. Molecular nutrition & food research. 2020 09; 64(18):e2000489. doi: 10.1002/mnfr.202000489. [PMID: 32776430]
Mar Garcia-Aloy, Marynka Ulaszewska, Pietro Franceschi, Sheila Estruel-Amades, Christoph H Weinert, Alba Tor-Roca, Mireia Urpi-Sarda, Fulvio Mattivi, Cristina Andres-Lacueva. Discovery of Intake Biomarkers of Lentils, Chickpeas, and White Beans by Untargeted LC-MS Metabolomics in Serum and Urine. Molecular nutrition & food research. 2020 07; 64(13):e1901137. doi: 10.1002/mnfr.201901137. [PMID: 32420683]
Maho Sasaki, Yuri Nonoshita, Takashi Kajiya, Nobuhiko Atsuchi, Megumi Kido, Djong-Chi Chu, Lekh Raj Juneja, Yuji Minami, Katsuko Kajiya. Characteristic Analysis of Trigonelline Contained in Raphanus sativus Cv. Sakurajima Daikon and Results from the First Trial Examining Its Vasodilator Properties in Humans. Nutrients. 2020 Jun; 12(6):. doi: 10.3390/nu12061872. [PMID: 32585930]
Wenjing Liu, Mengqin Xia, Li Yang, Zhengtao Wang, Rui Wang, Yanhong Shi. Development and optimization of a method for determining betaine and trigonelline in the fruits of Lycium species by using solid-phase extraction combined with high-performance liquid chromatography-diode array detector. Journal of separation science. 2020 Jun; 43(11):2073-2078. doi: 10.1002/jssc.201901124. [PMID: 32129569]
Guilin Hu, Xingrong Peng, Xia Wang, Xian Li, Xing Li, Minghua Qiu. Excavation of coffee maturity markers and further research on their changes in coffee cherries of different maturity. Food research international (Ottawa, Ont.). 2020 06; 132(?):109121. doi: 10.1016/j.foodres.2020.109121. [PMID: 32331680]
Akshoo Rathi, Mohd Ishaq, Abul Kalam Najmi, Mohd Akhtar. Trigonelline Demonstrated Ameliorative Effects in Dexamethasone Induced Osteoporotic Rats. Drug research. 2020 Jun; 70(6):257-264. doi: 10.1055/a-1147-5724. [PMID: 32289834]
Mayara Fumiere Lemos, Consuelo Perez, Pedro Henrique Pereira da Cunha, Paulo Roberto Filgueiras, Lucas Louzada Pereira, Aymbiré Francisco Almeida da Fonseca, Demian R Ifa, Rodrigo Scherer. Chemical and sensory profile of new genotypes of Brazilian Coffea canephora. Food chemistry. 2020 Apr; 310(?):125850. doi: 10.1016/j.foodchem.2019.125850. [PMID: 31771915]
Erikka Loftfield, Joseph A Rothwell, Rashmi Sinha, Pekka Keski-Rahkonen, Nivonirina Robinot, Demetrius Albanes, Stephanie J Weinstein, Andriy Derkach, Joshua Sampson, Augustin Scalbert, Neal D Freedman. Prospective Investigation of Serum Metabolites, Coffee Drinking, Liver Cancer Incidence, and Liver Disease Mortality. Journal of the National Cancer Institute. 2020 03; 112(3):286-294. doi: 10.1093/jnci/djz122. [PMID: 31168595]
Yin-Pan Chau, Philip C M Au, Gloria H Y Li, Chor-Wing Sing, Vincent K F Cheng, Kathryn C B Tan, Annie W C Kung, Ching-Lung Cheung. Serum Metabolome of Coffee Consumption and its Association With Bone Mineral Density: The Hong Kong Osteoporosis Study. The Journal of clinical endocrinology and metabolism. 2020 03; 105(3):. doi: 10.1210/clinem/dgz210. [PMID: 31750515]
Mariana Campos Costa, Tayra Ferreira Oliveira Lima, Carlos Alberto Arcaro, Maiara Destro Inacio, Alexander Batista-Duharte, Iracilda Zeppone Carlos, Luís Carlos Spolidorio, Renata Pires Assis, Iguatemy Lourenço Brunetti, Amanda Martins Baviera. Trigonelline and curcumin alone, but not in combination, counteract oxidative stress and inflammation and increase glycation product detoxification in the liver and kidney of mice with high-fat diet-induced obesity. The Journal of nutritional biochemistry. 2020 02; 76(?):108303. doi: 10.1016/j.jnutbio.2019.108303. [PMID: 31812909]
Arita Dewi Nugrahini, Momoko Ishida, Toshifumi Nakagawa, Kosuke Nishi, Takuya Sugahara. Trigonelline: An alkaloid with anti-degranulation properties. Molecular immunology. 2020 02; 118(?):201-209. doi: 10.1016/j.molimm.2019.12.020. [PMID: 31896496]
Zhengguo Qiu, Kefeng Wang, Chao Jiang, Yuqiang Su, Xiaoying Fan, Jing Li, Sha Xue, Li Yao. Trigonelline protects hippocampal neurons from oxygen-glucose deprivation-induced injury through activating the PI3K/Akt pathway. Chemico-biological interactions. 2020 Feb; 317(?):108946. doi: 10.1016/j.cbi.2020.108946. [PMID: 31935362]
Zahra Lorigooini, Keyhan Sadeghi Dehsahraei, Elham Bijad, Saied Habibian Dehkordi, Hossein Amini-Khoei. Trigonelline through the Attenuation of Oxidative Stress Exerts Antidepressant- and Anxiolytic-Like Effects in a Mouse Model of Maternal Separation Stress. Pharmacology. 2020; 105(5-6):289-299. doi: 10.1159/000503728. [PMID: 31630147]
Paleerath Peerapen, Visith Thongboonkerd. Protective roles of trigonelline against oxalate-induced epithelial-to-mesenchymal transition in renal tubular epithelial cells: An in vitro study. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Jan; 135(?):110915. doi: 10.1016/j.fct.2019.110915. [PMID: 31669600]
Hossein Omidi-Ardali, Zahra Lorigooini, Amin Soltani, Shima Balali-Dehkordi, Hossein Amini-Khoei. Inflammatory responses bridge comorbid cardiac disorder in experimental model of IBD induced by DSS: protective effect of the trigonelline. Inflammopharmacology. 2019 Dec; 27(6):1265-1273. doi: 10.1007/s10787-019-00581-w. [PMID: 30924005]
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Thomas Sevrin, Marie-Cécile Alexandre-Gouabau, Blandine Castellano, Audrey Aguesse, Khadija Ouguerram, Patrick Ngyuen, Dominique Darmaun, Clair-Yves Boquien. Impact of Fenugreek on Milk Production in Rodent Models of Lactation Challenge. Nutrients. 2019 Oct; 11(11):. doi: 10.3390/nu11112571. [PMID: 31653107]
Xiaona Shao, Chen Chen, Chunsheng Miao, Xiaoyan Yu, Xiangjun Li, Jianan Geng, Dongyan Fan, Xueyuan Lin, Zhen Chen, Yan Shi. Expression analysis of microRNAs and their target genes during experimental diabetic renal lesions in rats administered with ginsenoside Rb1 and trigonelline. Die Pharmazie. 2019 08; 74(8):492-498. doi: 10.1691/ph.2019.8903. [PMID: 31526443]
Kanta Pravalika, Deepaneeta Sarmah, Harpreet Kaur, Kanchan Vats, Jackson Saraf, Madhuri Wanve, Kiran Kalia, Anupom Borah, Dileep R Yavagal, Kunjan R Dave, Pallab Bhattacharya. Trigonelline therapy confers neuroprotection by reduced glutathione mediated myeloperoxidase expression in animal model of ischemic stroke. Life sciences. 2019 Jan; 216(?):49-58. doi: 10.1016/j.lfs.2018.11.014. [PMID: 30414429]
Claire Lande, Sujaya Rao, Jeffrey T Morré, Gracie Galindo, Julie Kirby, Patrick N Reardon, Gerd Bobe, Jan Frederik Stevens. Linden (Tilia cordata) associated bumble bee mortality: Metabolomic analysis of nectar and bee muscle. PloS one. 2019; 14(7):e0218406. doi: 10.1371/journal.pone.0218406. [PMID: 31291287]
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Daiha Shin, Eun Hye Kim, Jaewang Lee, Jong-Lyel Roh. Nrf2 inhibition reverses resistance to GPX4 inhibitor-induced ferroptosis in head and neck cancer. Free radical biology & medicine. 2018 12; 129(?):454-462. doi: 10.1016/j.freeradbiomed.2018.10.426. [PMID: 30339884]
Love Sharma, Nazir A Lone, Rachel M Knott, Adil Hassan, Tasduq Abdullah. Trigonelline prevents high cholesterol and high fat diet induced hepatic lipid accumulation and lipo-toxicity in C57BL/6J mice, via restoration of hepatic autophagy. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Nov; 121(?):283-296. doi: 10.1016/j.fct.2018.09.011. [PMID: 30208301]
Filipe Corrêa Guizellini, Gustavo Galo Marcheafave, Miroslava Rakocevic, Roy Edward Bruns, Ieda Spacino Scarminio, Patricia Kaori Soares. PARAFAC HPLC-DAD metabolomic fingerprint investigation of reference and crossed coffees. Food research international (Ottawa, Ont.). 2018 11; 113(?):9-17. doi: 10.1016/j.foodres.2018.06.070. [PMID: 30195550]
Pedram Shokouh, Per Bendix Jeppesen, Kjeld Hermansen, Christoffer Laustsen, Hans Stødkilde-Jørgensen, Stephen Jacques Hamilton-Dutoit, Mette Søndergaard Schmedes, Haiyun Qi, Thomas Stokholm Nørlinger, Søren Gregersen. Effects of Unfiltered Coffee and Bioactive Coffee Compounds on the Development of Metabolic Syndrome Components in a High-Fat-/High-Fructose-Fed Rat Model. Nutrients. 2018 Oct; 10(10):. doi: 10.3390/nu10101547. [PMID: 30347674]
Lu Liu, Xiaohuang Du, Zuo Zhang, Jiyin Zhou. Trigonelline inhibits caspase 3 to protect β cells apoptosis in streptozotocin-induced type 1 diabetic mice. European journal of pharmacology. 2018 Oct; 836(?):115-121. doi: 10.1016/j.ejphar.2018.08.025. [PMID: 30130525]
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Siraj Anwar, Uma Bhandari, Bibhu Prasad Panda, Kiran Dubey, Washim Khan, Sayeed Ahmad. Trigonelline inhibits intestinal microbial metabolism of choline and its associated cardiovascular risk. Journal of pharmaceutical and biomedical analysis. 2018 Sep; 159(?):100-112. doi: 10.1016/j.jpba.2018.06.027. [PMID: 29980011]
Mohsen Khalili, Mitra Alavi, Elham Esmaeil-Jamaat, Tourandokht Baluchnejadmojarad, Mehrdad Roghani. Trigonelline mitigates lipopolysaccharide-induced learning and memory impairment in the rat due to its anti-oxidative and anti-inflammatory effect. International immunopharmacology. 2018 Aug; 61(?):355-362. doi: 10.1016/j.intimp.2018.06.019. [PMID: 29935483]
Francisco Madrid-Gambin, Carl Brunius, Mar Garcia-Aloy, Sheila Estruel-Amades, Rikard Landberg, Cristina Andres-Lacueva. Untargeted 1H NMR-Based Metabolomics Analysis of Urine and Serum Profiles after Consumption of Lentils, Chickpeas, and Beans: An Extended Meal Study To Discover Dietary Biomarkers of Pulses. Journal of agricultural and food chemistry. 2018 Jul; 66(27):6997-7005. doi: 10.1021/acs.jafc.8b00047. [PMID: 29920085]
Roshana Devi Vellai, Sharmila Chandiran, Subramanian Sorimuthu Pillai. GTF-231, a Mixture of Gymnemic Acid, Trigonelline and Ferulic Acid Significantly Ameliorates Oxidative Stress in Experimental Type 2 Diabetes in Rats. Canadian journal of diabetes. 2018 Jun; 42(3):237-244. doi: 10.1016/j.jcjd.2017.05.007. [PMID: 28728928]
Amrita A Chowdhury, Nitin B Gawali, Renuka Munshi, Archana R Juvekar. Trigonelline insulates against oxidative stress, proinflammatory cytokines and restores BDNF levels in lipopolysaccharide induced cognitive impairment in adult mice. Metabolic brain disease. 2018 06; 33(3):681-691. doi: 10.1007/s11011-017-0147-5. [PMID: 29277879]
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Mostafa Pournamdari, Ali Mandegary, Fariba Sharififar, Ghazaleh Zarei, Rahele Zareshahi, Amir Asadi, Mohammad Mehdipour. Anti-Inflammatory Subfractions Separated from Acidified Chloroform Fraction of Fenugreek Seeds (Trigonella foenum-graecum L.). Journal of dietary supplements. 2018 Jan; 15(1):98-107. doi: 10.1080/19390211.2017.1326431. [PMID: 28558255]
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Wei Li, Fengxia Zhang, Ranran Wu, Lijia Jia, Guosheng Li, Yalong Guo, Cuimin Liu, Guodong Wang. A Novel N-Methyltransferase in Arabidopsis Appears to Feed a Conserved Pathway for Nicotinate Detoxification among Land Plants and Is Associated with Lignin Biosynthesis. Plant physiology. 2017 Jul; 174(3):1492-1504. doi: 10.1104/pp.17.00259. [PMID: 28533213]
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Joanna Folwarczna, Aleksandra Janas, Maria Pytlik, Urszula Cegieła, Leszek Śliwiński, Zora Krivošíková, Kornélia Štefíková, Martin Gajdoš. Effects of Trigonelline, an Alkaloid Present in Coffee, on Diabetes-Induced Disorders in the Rat Skeletal System. Nutrients. 2016 Mar; 8(3):133. doi: 10.3390/nu8030133. [PMID: 26950142]
Paulrayer Antonisamy, Mariadhas Valan Arasu, Muniappan Dhanasekaran, Ki Choon Choi, Adithan Aravinthan, Nam Soo Kim, Chang-Won Kang, Jong-Hoon Kim. Protective effects of trigonelline against indomethacin-induced gastric ulcer in rats and potential underlying mechanisms. Food & function. 2016 Jan; 7(1):398-408. doi: 10.1039/c5fo00403a. [PMID: 26499137]
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