Capsanthin (BioDeep_00000280681)

Main id: BioDeep_00000000683

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


(2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethyl-19-[(4R)-2,6,6-trimethyl-4-oxidanyl-cyclohexen-1-yl]-1-[(1R,4S)-1,2,2-trimethyl-4-oxidanyl-cyclopentyl]nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

化学式: C40H56O3 (584.4229)
中文名称: 辣椒红(油状)
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(=O)[C@]1(C)C[C@H](CC1(C)C)O)/C=C/C=C(\C)/C=C/C1=C(C)C[C@H](CC1(C)C)O
InChI: InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1

描述信息

Capsanthin is a carotenone. It has a role as a plant metabolite.
Capsanthin is a natural product found in Capsicum annuum, Lilium lancifolium, and Gallus gallus with data available.
See also: Red Pepper (part of).
D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

同义名列表

36 个代谢物同义名

(2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethyl-19-[(4R)-2,6,6-trimethyl-4-oxidanyl-cyclohexen-1-yl]-1-[(1R,4S)-1,2,2-trimethyl-4-oxidanyl-cyclopentyl]nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one; (2E,4E,6E,8E,10E,12E,14E,16E,18E)-1-((1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl)-19-((R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one; (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethyl-1-nonadeca-2,4,6,8,10,12,14,16,18-nonaenone; (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one; (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one; 2,4,6,8,10,12,14,16,18-NONADECANONAEN-1-ONE, 19-(4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-1-(4-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-, (ALL-E)-; 2,4,6,8,10,12,14,16,18-NONADECANONAEN-1-ONE, 19-(4-HYDROXY-2,6,6-TRIMETHYL-1-CYCLOHEXEN-1-YL)-1-(5-HYDROXY-1,2,2-TRIMETHYLCYCLOPENTYL)-4,8,13,17-TETRAMETHYL-; (3R,3S,5R)-3,3-DIHYDROXY-.BETA.,.KAPPA.-CAROTEN-6-ONE; (3R,3S,5R)-3,3-Dihydroxy-beta,kappa-caroten-6-one; .BETA.,.KAPPA.-CAROTEN-6ONE, 3,3DIHYDROXY-; 3,3-DIHYDROXY-.BETA.,.KAPPA.-CAROTEN-6ON; beta,kappa-Caroten-6one, 3,3dihydroxy-; 3,3-Dihydroxy-beta,kappa-caroten-6one; capsanthin, (3R,3S,5R,13-cis)-isomer; 3,3-DIHYDROXY-beta,kappa-CAROTEN-6ON; CAPSANTHIN/CAPSORUBIN [INCI]; Capsanthin, >=90.0\\% (HPLC); Capsanthin/capsorubin; all-trans-capsanthin; all trans Capsanthin; CAPSANTHIN [MI]; Capsanthin; (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethyl-cyclopentyl]-4,8,13,17-tetramethyl-nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one; (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one; SDCCGMLS-0066894.P001; Capsanthin\capsorubin; UPCMLD-DP025:001; EINECS 207-364-1; SPECTRUM1505276; Paprika extract; NCGC00161603-01; LMPR01070265; CHEBI:3375; 465-42-9; C08584; Capsanthin



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

26 个相关的物种来源信息

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。

亚细胞结构定位 关联基因列表
Cytoplasm 5 ABCB1, ADIG, APOE, CAT, PTGS2
Peripheral membrane protein 2 MBP, PTGS2
Endoplasmic reticulum membrane 1 PTGS2
Nucleus 5 ADIG, APOE, EZH2, MBP, MMP2
cytosol 4 ACOX1, CAT, LEP, MBP
dendrite 1 APOE
nucleoplasm 1 EZH2
Cell membrane 3 ABCB1, TNF, VCAM1
Cytoplasmic side 1 MBP
Multi-pass membrane protein 2 ABCB1, CPT1A
Synapse 2 EZH2, MBP
cell surface 5 ABCB1, ADIPOQ, MBP, TNF, VCAM1
glutamatergic synapse 1 APOE
Golgi apparatus 2 APOE, VCAM1
Golgi membrane 1 INS
neuronal cell body 3 APOE, MBP, TNF
sarcolemma 1 VCAM1
plasma membrane 6 ABCB1, APOE, MBP, MMP2, TNF, VCAM1
Membrane 7 ABCB1, ACOX1, ADIG, APOE, CAT, CPT1A, VCAM1
apical plasma membrane 1 ABCB1
caveola 1 PTGS2
extracellular exosome 5 ABCB1, APOE, CAT, MBP, VCAM1
endoplasmic reticulum 4 ADIPOQ, APOE, PTGS2, VCAM1
extracellular space 11 ADIPOQ, APOE, CCL2, IL2, IL4, IL6, INS, LEP, MMP2, TNF, VCAM1
mitochondrion 3 CAT, CPT1A, MMP2
protein-containing complex 3 CAT, MBP, PTGS2
intracellular membrane-bounded organelle 1 CAT
Microsome membrane 1 PTGS2
filopodium 1 VCAM1
chromatin silencing complex 1 EZH2
ESC/E(Z) complex 1 EZH2
pericentric heterochromatin 1 EZH2
pronucleus 1 EZH2
Single-pass type I membrane protein 1 VCAM1
Secreted 9 ADIG, ADIPOQ, APOE, CCL2, IL2, IL4, IL6, INS, LEP
extracellular region 13 ADIG, ADIPOQ, APOE, CAT, CCL2, IL2, IL4, IL6, INS, LEP, MBP, MMP2, TNF
Mitochondrion outer membrane 1 CPT1A
Single-pass membrane protein 1 ADIG
mitochondrial outer membrane 1 CPT1A
mitochondrial matrix 1 CAT
external side of plasma membrane 2 TNF, VCAM1
Endosome, multivesicular body 1 APOE
Extracellular vesicle 1 APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 1 APOE
high-density lipoprotein particle 1 APOE
low-density lipoprotein particle 1 APOE
multivesicular body 1 APOE
very-low-density lipoprotein particle 1 APOE
Early endosome 2 APOE, VCAM1
apical part of cell 1 VCAM1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCB1
Membrane raft 1 TNF
focal adhesion 1 CAT
extracellular matrix 2 APOE, MMP2
Peroxisome 2 ACOX1, CAT
collagen trimer 1 ADIPOQ
Peroxisome matrix 1 CAT
peroxisomal matrix 2 ACOX1, CAT
peroxisomal membrane 2 ACOX1, CAT
collagen-containing extracellular matrix 4 ADIPOQ, APOE, MBP, MMP2
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
sarcomere 1 MMP2
neuron projection 1 PTGS2
chromatin 1 EZH2
phagocytic cup 1 TNF
cell periphery 1 MBP
Chromosome 1 EZH2
podosome 1 VCAM1
[Isoform 3]: Nucleus 1 MBP
Secreted, extracellular space 1 APOE
chromosome, telomeric region 1 EZH2
blood microparticle 1 APOE
endosome lumen 1 INS
microvillus 1 VCAM1
Lipid droplet 1 ADIG
Melanosome 1 APOE
myelin sheath 1 MBP
ficolin-1-rich granule lumen 2 CAT, MBP
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 4 APOE, IL6, INS, PTGS2
transport vesicle 2 INS, MBP
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 APOE
synaptic cleft 1 APOE
external side of apical plasma membrane 1 ABCB1
discoidal high-density lipoprotein particle 1 APOE
endocytic vesicle lumen 1 APOE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
compact myelin 1 MBP
internode region of axon 1 MBP
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
[Bone marrow proteoglycan]: Secreted 1 MBP
[Vascular cell adhesion protein 1]: Cell membrane 1 VCAM1
[Soluble Vascular Cell Adhesion Molecule-1]: Secreted 1 VCAM1
alpha9-beta1 integrin-vascular cell adhesion molecule-1 complex 1 VCAM1
Myelin membrane 1 MBP
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Seo-Young Lee, So-Jeong Jang, Hyo-Bong Jeong, Joung-Ho Lee, Geon Woo Kim, Jelli Venkatesh, Seungki Back, Jin-Kyung Kwon, Da-Min Choi, Jeong-Ll Kim, Geun-Joong Kim, Byoung-Cheorl Kang. Leaky mutations in the zeaxanthin epoxidase in Capsicum annuum result in bright-red fruit containing a high amount of zeaxanthin. The Plant journal : for cell and molecular biology. 2024 Jan; ?(?):. doi: 10.1111/tpj.16619. [PMID: 38180307]
  • Zhimin Lin, Muhammad Moaaz Ali, Xiaoyan Yi, Lijuan Zhang, Shaojuan Wang. Fast and High-Efficiency Synthesis of Capsanthin in Pepper by Transient Expression of Geminivirus. International journal of molecular sciences. 2023 Oct; 24(19):. doi: 10.3390/ijms241915008. [PMID: 37834456]
  • Leenet Edward Kennedy, Annie Abraham, Gunjan Kulkarni, Navya Shettigar, Tanika Dave, Madhur Kulkarni. Capsanthin, a Plant-Derived Xanthophyll: a Review of Pharmacology and Delivery Strategies. AAPS PharmSciTech. 2021 Jul; 22(5):203. doi: 10.1208/s12249-021-02065-z. [PMID: 34244867]
  • Hee Kyoung Joo, Yu Ran Lee, Eun-Ok Lee, Sungmin Kim, Hao Jin, Suna Kim, Yong Pyo Lim, Chul Geon An, Byeong Hwa Jeon. Protective Role of Dietary Capsanthin in a Mouse Model of Nonalcoholic Fatty Liver Disease. Journal of medicinal food. 2021 Jun; 24(6):635-644. doi: 10.1089/jmf.2020.4866. [PMID: 34161164]
  • Maiko Furubayashi, Akiko Kubo, Miho Takemura, Yuko Otani, Takashi Maoka, Yoshinobu Terada, Katsuro Yaoi, Kohji Ohdan, Norihiko Misawa, Yasuo Mitani. Capsanthin Production in Escherichia coli by Overexpression of Capsanthin/Capsorubin Synthase from Capsicum annuum. Journal of agricultural and food chemistry. 2021 May; 69(17):5076-5085. doi: 10.1021/acs.jafc.1c00083. [PMID: 33890772]
  • Yavuz Erden. Capsanthin Stimulates the Mitochondrial Apoptosis-Mediated Cell Death, following DNA Damage in MCF-7 Cells. Nutrition and cancer. 2021; 73(4):662-670. doi: 10.1080/01635581.2020.1819347. [PMID: 32933334]
  • Yuqi Niu, Wenhui Gao, Hui Li, Jingxuan Zhang, Yunhe Lian. Rapid Determination of 17 Phthalate Esters in Capsanthin by QuEChERS Coupled with Gas Chromatography-Mass Spectrometry. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2020 Apr; 36(4):485-490. doi: 10.2116/analsci.19p421. [PMID: 31904006]
  • Tao Wu, Yufang Gao, Junyu Hao, Jieting Geng, Jiaojiao Zhang, Jinjin Yin, Rui Liu, Wenjie Sui, Lingxiao Gong, Min Zhang. Capsanthin extract prevents obesity, reduces serum TMAO levels and modulates the gut microbiota composition in high-fat-diet induced obese C57BL/6J mice. Food research international (Ottawa, Ont.). 2020 02; 128(?):108774. doi: 10.1016/j.foodres.2019.108774. [PMID: 31955744]
  • Wissanee Pola, Sumiko Sugaya, Songsin Photchanachai. Color Development and Phytochemical Changes in Mature Green Chili (Capsicum annuum L.) Exposed to Red and Blue Light-Emitting Diodes. Journal of agricultural and food chemistry. 2020 Jan; 68(1):59-66. doi: 10.1021/acs.jafc.9b04918. [PMID: 31816240]
  • Dario Piano, Emma Cocco, Giulia Guadalupi, Hazem M Kalaji, Joanna Kirkpatrick, Domenica Farci. Characterization under quasi-native conditions of the capsanthin/capsorubin synthase from Capsicum annuum L. Plant physiology and biochemistry : PPB. 2019 Oct; 143(?):165-175. doi: 10.1016/j.plaphy.2019.09.007. [PMID: 31505449]
  • Julie Le Grandois, Delphine Guffond, Erwann Hamon, Eric Marchioni, Dalal Werner. Combined microplate-ABTS and HPLC-ABTS analysis of tomato and pepper extracts reveals synergetic and antagonist effects of their lipophilic antioxidative components. Food chemistry. 2017 May; 223(?):62-71. doi: 10.1016/j.foodchem.2016.12.008. [PMID: 28069124]
  • Ji-Sun Kim, Woo-Moon Lee, Han Cheol Rhee, Suna Kim. Red paprika (Capsicum annuum L.) and its main carotenoids, capsanthin and β-carotene, prevent hydrogen peroxide-induced inhibition of gap-junction intercellular communication. Chemico-biological interactions. 2016 Jul; 254(?):146-55. doi: 10.1016/j.cbi.2016.05.004. [PMID: 27154496]
  • Tania Chacón-Ordóñez, Patricia Esquivel, Víctor M Jiménez, Reinhold Carle, Ralf M Schweiggert. Deposition Form and Bioaccessibility of Keto-carotenoids from Mamey Sapote (Pouteria sapota), Red Bell Pepper (Capsicum annuum), and Sockeye Salmon (Oncorhynchus nerka) Filet. Journal of agricultural and food chemistry. 2016 Mar; 64(9):1989-98. doi: 10.1021/acs.jafc.5b06039. [PMID: 26888016]
  • Azusa Nishino, Takashi Ichihara, Takeshi Takaha, Takashi Kuriki, Hideko Nihei, Kazuhisa Kawamoto, Hiroyuki Yasui, Takashi Maoka. Accumulation of Paprika Carotenoids in Human Plasma and Erythrocytes. Journal of oleo science. 2015; 64(10):1135-42. doi: 10.5650/jos.ess15118. [PMID: 26369598]
  • Shi-Lin Tian, Li Li, Wei-Guo Chai, Syed Noor Muhammad Shah, Zhen-Hui Gong. Effects of silencing key genes in the capsanthin biosynthetic pathway on fruit color of detached pepper fruits. BMC plant biology. 2014 Nov; 14(?):314. doi: 10.1186/s12870-014-0314-3. [PMID: 25403855]
  • Ji-Sun Kim, Jiyun Ahn, Sung-Joon Lee, Bokyung Moon, Tae-Youl Ha, Suna Kim. Phytochemicals and antioxidant activity of fruits and leaves of paprika (Capsicum Annuum L., var. special) cultivated in Korea. Journal of food science. 2011 Mar; 76(2):C193-8. doi: 10.1111/j.1750-3841.2010.01891.x. [PMID: 21535734]
  • Koichi Aizawa, Takahiro Inakuma. Dietary capsanthin, the main carotenoid in paprika (Capsicum annuum), alters plasma high-density lipoprotein-cholesterol levels and hepatic gene expression in rats. The British journal of nutrition. 2009 Dec; 102(12):1760-6. doi: 10.1017/s0007114509991309. [PMID: 19646292]
  • T Sun, Z Xu, C-T Wu, M Janes, W Prinyawiwatkul, H K No. Antioxidant activities of different colored sweet bell peppers (Capsicum annuum L.). Journal of food science. 2007 Mar; 72(2):S98-102. doi: 10.1111/j.1750-3841.2006.00245.x. [PMID: 17995862]
  • Muhammad Asim Siddique, Jonas Grossmann, Wilhelm Gruissem, Sacha Baginsky. Proteome analysis of bell pepper (Capsicum annuum L.) chromoplasts. Plant & cell physiology. 2006 Dec; 47(12):1663-73. doi: 10.1093/pcp/pcl033. [PMID: 17098784]
  • Genoveva Ingle de la Mora, J L Arredondo-Figueroa, Irene de los Angeles Barriga-Sosa, J Bazán-Arias, J Vernon-Carter. [Effects of the dietary incorporation of carotenoid pigments on gonad development and oocyte maturity in females of rainbow trout (Oncorhynchus mykiss, Walbaum, 1972)]. Archivos latinoamericanos de nutricion. 2004 Jun; 54(2):235-40. doi: ". [PMID: 15586694]
  • Antonio Pérez-Gálvez, Hans D Martin, Helmut Sies, Wilhelm Stahl. Incorporation of carotenoids from paprika oleoresin into human chylomicrons. The British journal of nutrition. 2003 Jun; 89(6):787-93. doi: 10.1079/bjn2003842. [PMID: 12828795]
  • D E Breithaupt, P Weller, M A Grashorn. Quantification of carotenoids in chicken plasma after feeding free or esterified lutein and capsanthin using high-performance liquid chromatography and liquid chromatography-mass spectrometry analysis. Poultry science. 2003 Mar; 82(3):395-401. doi: 10.1093/ps/82.3.395. [PMID: 12705399]
  • A Pérez-Gálvez, M I Mínguez-Mosquera. Structure-reactivity relationship in the oxidation of carotenoid pigments of the pepper (Capsicum annuum L.). Journal of agricultural and food chemistry. 2001 Oct; 49(10):4864-9. doi: 10.1021/jf010547c. [PMID: 11600036]
  • T Narisawa, Y Fukaura, M Hasebe, S Nomura, S Oshima, T Inakuma. Prevention of N-methylnitrosourea-induced colon carcinogenesis in rats by oxygenated carotenoid capsanthin and capsanthin-rich paprika juice. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 2000 Jun; 224(2):116-22. doi: 10.1046/j.1525-1373.2000.22409.x. [PMID: 10806419]
  • M H Kumagai, Y Keller, F Bouvier, D Clary, B Camara. Functional integration of non-native carotenoids into chloroplasts by viral-derived expression of capsanthin-capsorubin synthase in Nicotiana benthamiana. The Plant journal : for cell and molecular biology. 1998 May; 14(3):305-15. doi: 10.1046/j.1365-313x.1998.00128.x. [PMID: 9628025]
  • S Oshima, H Sakamoto, Y Ishiguro, J Terao. Accumulation and clearance of capsanthin in blood plasma after the ingestion of paprika juice in men. The Journal of nutrition. 1997 Aug; 127(8):1475-9. doi: 10.1093/jn/127.8.1475. [PMID: 9237940]
  • M Weissenberg, I Schaeffler, E Menagem, M Barzilai, A Levy. Isocratic non-aqueous reversed-phase high-performance liquid chromatographic separation of capsanthin and capsorubin in red peppers (Capsicum annuum L.), paprika and oleoresin. Journal of chromatography. A. 1997 Jan; 757(1-2):89-95. doi: 10.1016/s0021-9673(96)00665-6. [PMID: 9025261]
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