Tectochrysin (BioDeep_00000003602)

natural product PANOMIX_OTCML-2023

代谢物信息卡片

4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-phenyl- (9CI)

化学式: C16H12O4 (268.0735552)
中文名称: 杨芽黄素, 柚木柯因
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 91.84%

分子结构信息

SMILES: c1(cc(c2c(c1)oc(cc2=O)c1ccccc1)O)OC
InChI: InChI=1S/C16H12O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-9,17H,1H3

描述信息

7-methylchrysin, also known as 5-hydroxy-7-methoxyflavone or techtochrysin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 7-methylchrysin is considered to be a flavonoid lipid molecule. 7-methylchrysin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-methylchrysin can be found in pine nut, prunus (cherry, plum), sour cherry, and sweet cherry, which makes 7-methylchrysin a potential biomarker for the consumption of these food products.
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.330
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.324
Tectochrysin (Techtochrysin) is one of the major flavonoids of Alpinia oxyphylla Miquel. Tectochrysin inhibits activity of NF-κB.
Tectochrysin (Techtochrysin) is one of the major flavonoids of Alpinia oxyphylla Miquel. Tectochrysin inhibits activity of NF-κB.

同义名列表

33 个代谢物同义名

7-Methylchrysin; Tectochrysin; 4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-phenyl- (9CI); 4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-phenyl-; 5-Hydroxy-7-methoxy-2-phenyl-chromen-4-one; 5-hydroxy-7-methoxy-2-phenylchromen-4-one; 5-hydroxy-7-methoxy-2-phenyl-4-chromenone; 5-hydroxy-7-methoxy-2-phenyl-chromone; Flavone, 5-hydroxy-7-methoxy- (8CI); Flavone, 5-hydroxy-7-methoxy-; 5-Hydroxy-7-methoxyflavone; 7-Methoxy-5-hydroxyflavone; Maybridge3_003219; SR-01000402578-2; NCGC00142540-01; NCGC00017176-01; Oprea1_023530; Oprea1_215176; Techtochrysin; MLS001049041; SMR000387029; ZINC00042243; BAS 00872586; MLS000697658; AIDS-059327; IDI1_014606; AIDS059327; NSC 80687; ST057541; NSC80687; TNP00038; 520-28-5; C11621

数据库引用编号

25 个数据库交叉引用编号

ChEBI: CHEBI:9426
KEGG: C11621
PubChem: 5281954
Metlin: METLIN48621
ChEMBL: CHEMBL164841
LipidMAPS: LMPK12110190
KNApSAcK: C00003795
foodb: FDB015536
CAS: 520-28-5
MoNA: CCMSLIB00000081300
MoNA: CCMSLIB00000081301
MoNA: MetaboBASE0552
MoNA: MetaboBASE0551
MoNA: MetaboBASE0550
MoNA: MetaboBASE0549
MoNA: MetaboBASE0548
MoNA: BML82232
MoNA: BML82230
MoNA: BML00756
MoNA: BML00749
PMhub: MS000010220
Flavonoid: FL3FA9NS0003
PubChem: 13786
NIKKAJI: J61.252I
medchemexpress: HY-14592

分类词条

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)

86 个相关的物种来源信息

203717 防风: -
33090 益智: -
73824 Populus balsamifera:
1616482 Populus candicans:
3696 Populus deltoides:
7460 Apis mellifera: 10.1021/NP50028A007
588669 Aster tataricus:
405331 Piper khasianum:
405345 Piper sylvaticum:
2306373 Helichrysum kraussii: 10.1016/0031-9422(89)80195-5
1754142 Helichrysum tomentosulum: 10.1016/0031-9422(89)80195-5
630334 Helichrysum schimperi: 10.1016/0031-9422(90)80127-3
130377 Piper aduncum: 10.1016/S0031-9422(97)00828-5
88733 Pinus armandii: 10.1016/0031-9422(88)80201-2
139307 Pinus morrisonicola:
113624 Populus laurifolia: 10.1007/BF00630627
3691 Populus nigra:
140311 Prunus cerasus: 10.1021/JF980936F
42229 Prunus avium:
3345 Pinus monticola: 10.3891/ACTA.CHEM.SCAND.03-1147
253221 Alnus sieboldiana: 10.1246/BCSJ.44.2761
45164 Muntingia calabura: 10.1055/S-2005-871223
83951 Oroxylum indicum: 10.1016/J.BMCL.2009.11.024
1417776 Pelargonium crispum: 10.1016/S0031-9422(97)00514-1
392618 Cunila: 10.1007/S00299-018-2303-8
993104 Picea abies var. abies: 10.3891/ACTA.CHEM.SCAND.03-1375
7459 Apis: 10.4103/0971-4065.82131
97729 Boesenbergia rotunda:
1569415 Maschalostachys markgrafii: 10.1016/S0305-1978(01)00127-2
1202417 Monanthotaxis enghiana: 10.1016/S0031-9422(96)00527-4
29742 Comptonia peregrina: 10.1016/S0176-1617(85)80049-3
2651278 Pongamia pinnata var. pinnata: 10.1016/J.BMC.2009.05.051
2566160 Andrographis macrobotrys: 10.1016/S0031-9422(03)00051-7
2058692 Bryobium eriaeoides:
97751 Kaempferia parviflora:
39289 Collinsonia canadensis: 10.1021/NP980421I
204228 Hoslundia opposita: 10.1016/S0031-9422(00)95112-4
125261 Alpinia oxyphylla:
429669 Godmania aesculifolia: 10.1016/0305-1978(96)88880-6
174980 Uvaria rufa:
225837 Uvaria lucida: 10.1071/CH9892289
110723 Hedychium spicatum: 10.1016/J.BMCL.2008.10.121
73824 Populus balsamifera:
1616482 Populus candicans:
3696 Populus deltoides:
7460 Apis mellifera: 10.1021/NP50028A007
588669 Aster tataricus:
405331 Piper khasianum:
405345 Piper sylvaticum:
2306373 Helichrysum kraussii: 10.1016/0031-9422(89)80195-5
1754142 Helichrysum tomentosulum: 10.1016/0031-9422(89)80195-5
630334 Helichrysum schimperi: 10.1016/0031-9422(90)80127-3
130377 Piper aduncum: 10.1016/S0031-9422(97)00828-5
88733 Pinus armandii: 10.1016/0031-9422(88)80201-2
139307 Pinus morrisonicola:
113624 Populus laurifolia: 10.1007/BF00630627
3691 Populus nigra:
140311 Prunus cerasus: 10.1021/JF980936F
42229 Prunus avium:
3345 Pinus monticola: 10.3891/ACTA.CHEM.SCAND.03-1147
253221 Alnus sieboldiana: 10.1246/BCSJ.44.2761
45164 Muntingia calabura: 10.1055/S-2005-871223
83951 Oroxylum indicum: 10.1016/J.BMCL.2009.11.024
1417776 Pelargonium crispum: 10.1016/S0031-9422(97)00514-1
392618 Cunila: 10.1007/S00299-018-2303-8
993104 Picea abies var. abies: 10.3891/ACTA.CHEM.SCAND.03-1375
7459 Apis: 10.4103/0971-4065.82131
97729 Boesenbergia rotunda:
1569415 Maschalostachys markgrafii: 10.1016/S0305-1978(01)00127-2
1202417 Monanthotaxis enghiana: 10.1016/S0031-9422(96)00527-4
29742 Comptonia peregrina: 10.1016/S0176-1617(85)80049-3
2651278 Pongamia pinnata var. pinnata: 10.1016/J.BMC.2009.05.051
2566160 Andrographis macrobotrys: 10.1016/S0031-9422(03)00051-7
2058692 Bryobium eriaeoides:
97751 Kaempferia parviflora:
39289 Collinsonia canadensis: 10.1021/NP980421I
204228 Hoslundia opposita: 10.1016/S0031-9422(00)95112-4
125261 Alpinia oxyphylla:
429669 Godmania aesculifolia: 10.1016/0305-1978(96)88880-6
174980 Uvaria rufa:
225837 Uvaria lucida: 10.1071/CH9892289
110723 Hedychium spicatum: 10.1016/J.BMCL.2008.10.121
569774 金线莲: -
125261 Alpinia oxyphylla Miq.: -
266767 Populus davidiana: -
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

Dinesh Kumar Patel. Ethnopharmacological uses, pharmacological activities, and therapeutic applications of tectochrysin in Medicine: An important class of dietary flavonoid. Cardiovascular & hematological disorders drug targets. 2023 Jul; ?(?):. doi: 10.2174/1871529x23666230726143243. [PMID: 37496140]
Lei Fang, Ying Yan, Zhengxin Xu, Zhenpeng He, Shuting Zhou, Xin Jiang, Fan Wu, Xiaoling Yuan, Tong Zhang, Duonan Yu. Tectochrysin ameliorates murine allergic airway inflammation by suppressing Th2 response and oxidative stress. European journal of pharmacology. 2021 Jul; 902(?):174100. doi: 10.1016/j.ejphar.2021.174100. [PMID: 33878335]
Noriyuki Natsume, Aki Yamano, Akio Watanabe, Takayuki Yonezawa, Je-Tae Woo, Tohru Yamakuni, Toshiaki Teruya. Effect of methoxyflavones contained in Kaempferia parviflora on CRE-mediated transcription in PC12D cells. Bioorganic & medicinal chemistry letters. 2020 12; 30(23):127606. doi: 10.1016/j.bmcl.2020.127606. [PMID: 33038547]
Min Lu, Lin Tan, Xiao-Gang Zhou, Zhong-Lin Yang, Qing Zhu, Jian-Ning Chen, Huai-Rong Luo, Gui-Sheng Wu. Tectochrysin increases stress resistance and extends the lifespan of Caenorhabditis elegans via FOXO/DAF-16. Biogerontology. 2020 10; 21(5):669-682. doi: 10.1007/s10522-020-09884-w. [PMID: 32506187]
Alvaro José Hernández Tasco, Román Yesid Ramírez Rueda, Carlos José Alvarez, Fabiana Terezinha Sartori, Ana Claudia B C Sacilotto, Izabel Yoko Ito, Walter Vichnewski, Marcos José Salvador. Antibacterial and antifungal properties of crude extracts and isolated compounds from Lychnophora markgravii. Natural product research. 2020 Mar; 34(6):863-867. doi: 10.1080/14786419.2018.1503263. [PMID: 30445853]
Qing Niu, Yumei Gao, Pinghuai Liu. Optimization of microwave-assisted extraction, antioxidant capacity, and characterization of total flavonoids from the leaves of Alpinia oxyphylla Miq. Preparative biochemistry & biotechnology. 2020; 50(1):82-90. doi: 10.1080/10826068.2019.1663535. [PMID: 31545661]
Pornphimol Meesakul, Christopher Richardson, Stephen G Pyne, Surat Laphookhieo. α-Glucosidase Inhibitory Flavonoids and Oxepinones from the Leaf and Twig Extracts of Desmos cochinchinensis. Journal of natural products. 2019 04; 82(4):741-747. doi: 10.1021/acs.jnatprod.8b00581. [PMID: 30835120]
Qamar Uddin Ahmed, Murni Nazira Sarian, Siti Zaiton Mat So'ad, Jalifah Latip, Solachuddin Jauhari Arief Ichwan, Nurlaili Najmie Hussein, Muhammad Taher, Alhassan Muhammad Alhassan, Hanisuhana Hamidon, Sharida Fakurazi. Methylation and Acetylation Enhanced the Antidiabetic Activity of Some Selected Flavonoids: In Vitro, Molecular Modelling and Structure Activity Relationship-Based Study. Biomolecules. 2018 11; 8(4):. doi: 10.3390/biom8040149. [PMID: 30445784]
Xu Zhao, Xin Su, Chunmei Liu, Ying Jia. Simultaneous Determination of Chrysin and Tectochrysin from Alpinia oxyphylla Fruits by UPLC-MS/MS and Its Application to a Comparative Pharmacokinetic Study in Normal and Dementia Rats. Molecules (Basel, Switzerland). 2018 Jul; 23(7):. doi: 10.3390/molecules23071702. [PMID: 30002311]
Rui Hou, Yixin Han, Qiaoling Fei, Yuan Gao, Ruijuan Qi, Runlan Cai, Yun Qi. Dietary Flavone Tectochrysin Exerts Anti-Inflammatory Action by Directly Inhibiting MEK1/2 in LPS-Primed Macrophages. Molecular nutrition & food research. 2018 01; 62(2):. doi: 10.1002/mnfr.201700288. [PMID: 28980448]
Junqing Zhang, Sheng Wang, Yonghui Li, Peng Xu, Feng Chen, Yinfeng Tan, Jinao Duan. Anti-diarrheal constituents of Alpinia oxyphylla. Fitoterapia. 2013 Sep; 89(?):149-56. doi: 10.1016/j.fitote.2013.04.001. [PMID: 23583435]
Catheleeya Mekjaruskul, Michael Jay, Bungorn Sripanidkulchai. Pharmacokinetics, bioavailability, tissue distribution, excretion, and metabolite identification of methoxyflavones in Kaempferia parviflora extract in rats. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2342-53. doi: 10.1124/dmd.112.047142. [PMID: 22961680]
Hsiang-Ruei Liao, Jih-Jung Chen, Yin-Huan Chien, Shinn-Zhi Lin, Shunchih Lin, Ching-Ping Tseng. 5-Hydroxy-7-methoxyflavone inhibits N-formyl-L-methionyl-L-leucyl-L-phenylalanine-induced superoxide anion production by specific modulate membrane localization of Tec with a PI3K independent mechanism in human neutrophils. Biochemical pharmacology. 2012 Jul; 84(2):182-91. doi: 10.1016/j.bcp.2012.03.015. [PMID: 22484311]
Lingyun Zhong, Ligang Zhou, Yaming Zhou, Yuanquan Chen, Peng Sui, Jingguo Wang, Mingan Wang. Antimicrobial flavonoids from the twigs of Populus nigra x Populus deltoides. Natural product research. 2012; 26(4):307-13. doi: 10.1080/14786411003675667. [PMID: 21416454]
Xu-Dong Cao, Zhi-Shan Ding, Fu-Sheng Jiang, Xing-Hong Ding, Jian-Zhen Chen, Su-Hong Chen, Gui-Yuan Lv. Antitumor constituents from the leaves of Carya cathayensis. Natural product research. 2012; 26(22):2089-94. doi: 10.1080/14786419.2011.628174. [PMID: 22007794]
Monika Barbarić, Katarina Mišković, Mirza Bojić, Mirela Baus Lončar, Asja Smolčić-Bubalo, Zeljko Debeljak, Marica Medić-Šarić. Chemical composition of the ethanolic propolis extracts and its effect on HeLa cells. Journal of ethnopharmacology. 2011 Jun; 135(3):772-8. doi: 10.1016/j.jep.2011.04.015. [PMID: 21515353]
K Boutabet, W Kebsa, M Alyane, M Lahouel. Polyphenolic fraction of Algerian propolis protects rat kidney against acute oxidative stress induced by doxorubicin. Indian journal of nephrology. 2011 Apr; 21(2):101-6. doi: 10.4103/0971-4065.82131. [PMID: 21769172]
Elizabeth A Mazzio, Fran Close, Karam F A Soliman. The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease. International journal of molecular sciences. 2011 Jan; 12(1):506-69. doi: 10.3390/ijms12010506. [PMID: 21340000]
Bo Zhao, Xinbao Yang, Xiuwei Yang, Lianxue Zhang. [Chemical constituents of roots of Saposhnikovia divaricata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Jun; 35(12):1569-72. doi: 10.4268/cjcmm20101214. [PMID: 20815209]
T Hari Babu, K Manjulatha, G Suresh Kumar, A Hymavathi, Ashok K Tiwari, Muraleedhar Purohit, J Madhusudana Rao, K Suresh Babu. Gastroprotective flavonoid constituents from Oroxylum indicum Vent. Bioorganic & medicinal chemistry letters. 2010 Jan; 20(1):117-20. doi: 10.1016/j.bmcl.2009.11.024. [PMID: 19948405]
Marica Medić-Sarić, Vesna Rastija, Mirza Bojić, Zeljan Males. From functional food to medicinal product: systematic approach in analysis of polyphenolics from propolis and wine. Nutrition journal. 2009 Jul; 8(?):33. doi: 10.1186/1475-2891-8-33. [PMID: 19624827]
R Ranga Rao, Ashok K Tiwari, P Prabhakar Reddy, K Suresh Babu, Amtul Z Ali, K Madhusudana, J Madhusudana Rao. New furanoflavanoids, intestinal alpha-glucosidase inhibitory and free-radical (DPPH) scavenging, activity from antihyperglycemic root extract of Derris indica (Lam.). Bioorganic & medicinal chemistry. 2009 Jul; 17(14):5170-5. doi: 10.1016/j.bmc.2009.05.051. [PMID: 19515570]
Junju Xu, Ninghua Tan, Guangzhi Zeng, Hongjin Han, Huoqiang Huang, Changjiu Ji, Meiju Zhu, Yumei Zhang. [Studies on chemical constituents in fruit of Alpinia oxyphylla]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Apr; 34(8):990-3. doi: . [PMID: 19639783]
Bruno B Silva, Pedro L Rosalen, Jaime A Cury, Masaharu Ikegaki, Vinícius C Souza, Alessandro Esteves, Severino M Alencar. Chemical composition and botanical origin of red propolis, a new type of brazilian propolis. Evidence-based complementary and alternative medicine : eCAM. 2008 Sep; 5(3):313-6. doi: 10.1093/ecam/nem059. [PMID: 18830449]
Mansoor Ahmad, Noor Muhammad, Manzoor Ahmad, Muhammad Arif Lodhi, Noor Jehan, Zahid Khan, Rosa Ranjit, Farzana Shaheen, Muhammad Iqbal Choudhary. Urease inhibitor from Datisca cannabina linn. Journal of enzyme inhibition and medicinal chemistry. 2008 Jun; 23(3):386-90. doi: 10.1080/14756360701536513. [PMID: 18569344]
Supinya Tewtrakul, Sanan Subhadhirasakul, Sopa Kummee. Anti-allergic activity of compounds from Kaempferia parviflora. Journal of ethnopharmacology. 2008 Feb; 116(1):191-3. doi: 10.1016/j.jep.2007.10.042. [PMID: 18077118]
K Sookkongwaree, M Geitmann, S Roengsumran, A Petsom, U H Danielson. Inhibition of viral proteases by Zingiberaceae extracts and flavones isolated from Kaempferia parviflora. Die Pharmazie. 2006 Aug; 61(8):717-21. doi: . [PMID: 16964717]
Björn M Hausen. Evaluation of the main contact allergens in propolis (1995 to 2005). Dermatitis : contact, atopic, occupational, drug. 2005 Sep; 16(3):127-9. doi: . [PMID: 16242084]
Shafii Khamis, Michael C Bibby, John E Brown, Patricia A Cooper, Ian Scowen, Colin W Wright. Phytochemistry and preliminary biological evaluation of Cyathostemma argenteum, a malaysian plant used traditionally for the treatment of breast cancer. Phytotherapy research : PTR. 2004 Jul; 18(7):507-10. doi: 10.1002/ptr.1318. [PMID: 15305306]
R Takeara, S Albuquerque, N P Lopes, J L C Lopes. Trypanocidal activity of Lychnophora staavioides Mart. (Vernonieae, Asteraceae). Phytomedicine : international journal of phytotherapy and phytopharmacology. 2003; 10(6-7):490-3. doi: 10.1078/094471103322331430. [PMID: 13678232]
Sanghyun Lee, Kyoung Soon Kim, Youmie Park, Kuk Hyun Shin, Bak-Kwang Kim. In vivo anti-oxidant activities of tectochrysin. Archives of pharmacal research. 2003 Jan; 26(1):43-6. doi: 10.1007/bf03179930. [PMID: 12568357]
L Zhou, J Guo, J Yu. [Flavonoids from Beijing propolis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1999 Mar; 24(3):162-4, 191. doi: . [PMID: 12242799]