Centaureidin (BioDeep_00000266252)

PANOMIX_OTCML-2023

代谢物信息卡片

5,7-Dihydroxy-2- (3-hydroxy-4-methoxyphenyl) -3,6-dimethoxy-4H-1-benzopyran-4-one

化学式: C18H16O8 (360.0845136)
中文名称: 矢车菊黄素, 矢车菊黄素
谱图信息: 最多检出来源 Astragalus membranaceus(otcml) 50%

分子结构信息

SMILES: c(c3OC)(O)cc(O1)c(c3O)C(C(=C1c(c2)cc(O)c(OC)c2)OC)=O
InChI: InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3

描述信息

A trihydroxyflavone that consists of quercetagetin in which the hydroxy groups at positions 3, 6 and 4 have been replaced by methoxy groups. It has been isolated from Eremophila mitchellii and Athroisma proteiforme.

同义名列表

7 个代谢物同义名

4H-1-Benzopyran-4-one,5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-; Centaureidin; 5,7,3-Trihydroxy-3,6,4-trimethoxyflavone; Desmethoxycentaureidine; 5,7-Dihydroxy-2- (3-hydroxy-4-methoxyphenyl) -3,6-dimethoxy-4H-1-benzopyran-4-one; 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-1-benzopyran-4-one; Quercetagetin 3,4,6-trimethyl ether

数据库引用编号

9 个数据库交叉引用编号

ChEBI: CHEBI:69356
PubChem: 5315773
Metlin: METLIN51412
ChEMBL: CHEMBL77552
LipidMAPS: LMPK12113000
KNApSAcK: C00004694
CAS: 17313-52-9
Flavonoid: FL5FECNS0019
MetaboLights: MTBLC69356

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)

62 个相关的物种来源信息

1744983 - Acanthostyles buniifolius: 10.1055/S-2001-18355
282714 - Achillea abrotanoides: 10.1016/S0031-9422(00)97843-9
282719 - Achillea asiatica: 10.1016/0305-1978(88)90071-3
282720 - Achillea aspleniifolia:
282721 - Achillea atrata:
282726 - Achillea clavennae:
282727 - Achillea clusiana:
282730 - Achillea collina:
282733 - Achillea distans: 10.1016/0305-1978(88)90071-3
359926 - Achillea latiloba: 10.1016/S0305-1978(98)00112-4
282745 - Achillea ligustica: 10.1016/0305-1978(88)90033-6
13329 - Achillea millefolium:
482479 - Achillea millefolium var. borealis: 10.1016/0305-1978(88)90071-3
282751 - Achillea multifida:
282753 - Achillea nobilis: 10.1016/0305-1978(88)90033-6
282756 - Achillea pannonica: 10.1016/0305-1978(88)90071-3
282770 - Achillea virescens:
22994 - Aeonium: 10.1016/0031-9422(93)00074-P
99024 - Ajania fruticulosa:
3517 - Alnus glutinosa:
2065844 - Ambrosia chamissonis:
314052 - Anthemis candidissima: 10.1021/NP020472M
589788 - Anthemis ruthenica:
86306 - Artemisia abrotanum:
1227615 - Artemisia alba: 10.1016/S0031-9422(00)81695-7
72335 - Artemisia barrelieri:
205368 - Artemisia incanescens: 10.1016/S0031-9422(00)81695-7
86312 - Artemisia ludoviciana: 10.1515/ZNC-1995-5-604
72347 - Artemisia molinieri: 10.1515/ZNC-1995-5-604
1903237 - Artemisia vachanica:
1654445 - Baccharis neaei: 10.1021/NP50045A025
1573918 - Baccharis salicina:
2603409 - Baccharis sarothroides: 10.1016/S0031-9422(98)00363-X
1550803 - Brickellia baccharidea: 10.1016/S0031-9422(00)98581-9
1550813 - Brickellia cylindracea: 10.1016/0305-1978(83)90027-3
162709 - Cassia grandis: 10.1055/S-2006-957847
1033235 - Centaurea bracteata:
1436089 - Centaurea corcubionensis: 10.1055/S-2006-957386
351340 - Centaurea jacea:
910632 - Centaurea phrygia: 10.1016/0031-9422(91)85119-K
1458965 - Chiliadenus montanus: 10.1016/0031-9422(89)80084-6
589812 - Cota altissima: 10.1021/NP020472M
2652576 - Eremophila mitchellii: 10.1021/NP2003676
102770 - Eupatorium cannabinum: 10.1016/0305-1978(95)00011-I
662482 - Grindelia camporum: 10.1515/ZNC-1994-5-618
1114741 - Grindelia hirsutula: 10.1515/ZNC-1994-5-618
1114766 - Grindelia tarapacana:
2907093 - Heterotheca canescens: 10.1021/NP50021A021
1504456 - Maclurodendron porteri: 10.1021/NP50109A024
176559 - Pericome caudata: 10.1016/S0031-9422(00)82480-2
1936779 - Picradeniopsis schaffneri: 10.1016/S0031-9422(00)90497-7
1936782 - Picradeniopsis xylopoda: 10.1016/0031-9422(90)80042-F
1548625 - Pluchea chingoyo: 10.1016/S0031-9422(00)82733-8
175519 - Pluchea sagittalis: 10.1016/S0031-9422(00)84421-0
2950952 - Rhaponticoides africana: 10.1007/S10600-006-0228-X
185193 - Smallanthus fruticosus: 10.1016/S0960-894X(01)81233-6
558486 - Stevia monardifolia: 10.1021/NP50039A036
558490 - Stevia nepetifolia: 10.1021/NP50033A038
558494 - Stevia origanoides: 10.1021/NP50039A036
55670 - Stevia rebaudiana: 10.1021/NP50026A010
118510 - Tanacetum cinerariifolium:
127999 - Tanacetum parthenium:

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

Lysanne Salomon, Peter Lorenz, Marek Bunse, Otmar Spring, Florian C Stintzing, Dietmar R Kammerer. Comparison of the Phenolic Compound Profile and Antioxidant Potential of Achillea atrata L. and Achillea millefolium L. Molecules (Basel, Switzerland). 2021 Mar; 26(6):. doi: 10.3390/molecules26061530. [PMID: 33799635]
Samia Baatouche, Thamere Cheriet, Djamel Sarri, Ratiba Mekkiou, Ouahiba Boumaza, Samir Benayache, Fadila Benayache, Ignacio Brouard, Francisco León, Ramdane Seghiri. Centaurea microcarpa Coss. & Dur. (Asteraceae) extracts: New cyanogenic glucoside and other constituents. Natural product research. 2019 Nov; 33(21):3070-3076. doi: 10.1080/14786419.2018.1517343. [PMID: 30445872]
Kaan Polatoğlu, Omer Cem Karakoç, Fatih Demirci, Ayhan Gökçe, Nezhun Gören. Chemistry and biological activities of Tanacetum chiliophyllum var. oligocephalum extracts. Journal of AOAC International. 2013 Nov; 96(6):1222-7. doi: 10.5740/jaoacint.sgepolatoglu. [PMID: 24645497]
Jia-Ling Song, Yong-Jian Yang, Huan-Yang Qi, Qiang Li. [Chemical constituents from flowers of Gardenia jasminoides]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 May; 36(5):752-5. doi: ". [PMID: 24218967]
Peter Forgo, István Zupkó, Judit Molnár, Andrea Vasas, György Dombi, Judit Hohmann. Bioactivity-guided isolation of antiproliferative compounds from Centaurea jacea L. Fitoterapia. 2012 Jul; 83(5):921-5. doi: 10.1016/j.fitote.2012.04.006. [PMID: 22537643]
Shinji Nakama, Kazumi Tamaki, Chie Ishikawa, Masayuki Tadano, Naoki Mori. Efficacy of Bidens pilosa Extract against Herpes Simplex Virus Infection In Vitro and In Vivo. Evidence-based complementary and alternative medicine : eCAM. 2012; 2012(?):413453. doi: 10.1155/2012/413453. [PMID: 22474501]
Ende Pan, Alexander P Gorka, John N Alumasa, Carla Slebodnick, Liva Harinantenaina, Peggy J Brodie, Paul D Roepe, Richard Randrianaivo, Chris Birkinshaw, David G I Kingston. Antiplasmodial and antiproliferative pseudoguaianolides of Athroisma proteiforme from the Madagascar Dry Forest. Journal of natural products. 2011 Oct; 74(10):2174-80. doi: 10.1021/np200499d. [PMID: 21995542]
Nima D Namsa, Manabendra Mandal, Sumpam Tangjang, Subhash C Mandal. Ethnobotany of the Monpa ethnic group at Arunachal Pradesh, India. Journal of ethnobiology and ethnomedicine. 2011 Oct; 7(?):31. doi: 10.1186/1746-4269-7-31. [PMID: 21995750]
Emma C Barnes, Anthony R Carroll, Rohan A Davis. Mitchellenes A-E, cyclic sesquiterpenes from the Australian plant Eremophila mitchellii. Journal of natural products. 2011 Sep; 74(9):1888-93. doi: 10.1021/np2003676. [PMID: 21877688]
Sanjay M Jachak, Raju Gautam, C Selvam, Himanshu Madhan, Amit Srivastava, Taj Khan. Anti-inflammatory, cyclooxygenase inhibitory and antioxidant activities of standardized extracts of Tridax procumbens L. Fitoterapia. 2011 Mar; 82(2):173-7. doi: 10.1016/j.fitote.2010.08.016. [PMID: 20804828]
S Saeidnia, Ar Gohari, N Mokhber-Dezfuli, F Kiuchi. A review on phytochemistry and medicinal properties of the genus Achillea. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2011; 19(3):173-86. doi: ". [PMID: 22615655]
Zsuzsanna Hajdú, István Zupkó, Borbála Réthy, Peter Forgo, Judit Hohmann. Bioactivity-guided isolation of cytotoxic sesquiterpenes and flavonoids from Anthemis ruthenica. Planta medica. 2010 Jan; 76(1):94-6. doi: 10.1055/s-0029-1185942. [PMID: 19639540]
Paul R Hanlon, Melissa G Robbins, Chris Scholl, David M Barnes. Aqueous extracts from dietary supplements influence the production of inflammatory cytokines in immortalized and primary T lymphocytes. BMC complementary and alternative medicine. 2009 Dec; 9(?):51. doi: 10.1186/1472-6882-9-51. [PMID: 20003431]
Boglárka Csupor-Löffler, Zsuzsanna Hajdú, István Zupkó, Borbála Réthy, George Falkay, Peter Forgo, Judit Hohmann. Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines. Phytotherapy research : PTR. 2009 May; 23(5):672-6. doi: 10.1002/ptr.2697. [PMID: 19107850]
Shu-Lin Chang, Yi-Ming Chiang, Cicero Lee-Tian Chang, Hsu-Hua Yeh, Lie-Fen Shyur, Yueh-Hsiung Kuo, Tung-Kung Wu, Wen-Chin Yang. Flavonoids, centaurein and centaureidin, from Bidens pilosa, stimulate IFN-gamma expression. Journal of ethnopharmacology. 2007 Jun; 112(2):232-6. doi: 10.1016/j.jep.2007.03.001. [PMID: 17408892]
José Antonio Guerra, María Francisca Molina, María José Abad, Angel María Villar, Bermejo Paulina. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 expression by flavonoids isolated from Tanacetum microphyllum. International immunopharmacology. 2006 Nov; 6(11):1723-8. doi: 10.1016/j.intimp.2006.07.012. [PMID: 16979127]
Snezana Trifunović, Vlatka Vajs, Zorica Juranić, Zeljko Zizak, Vele Tesević, Slobodan Macura, Slobodan Milosavljević. Cytotoxic constituents of Achillea clavennae from Montenegro. Phytochemistry. 2006 May; 67(9):887-93. doi: 10.1016/j.phytochem.2006.02.026. [PMID: 16616262]
Gordana Stojanović, Niko Radulović, Toshihiro Hashimoto, Radosav Palić. In vitro antimicrobial activity of extracts of four Achillea species: the composition of Achillea clavennae L. (Asteraceae) extract. Journal of ethnopharmacology. 2005 Oct; 101(1-3):185-90. doi: 10.1016/j.jep.2005.04.026. [PMID: 15978758]
Tawfeq A Al-Howiriny, Adnan J Al-Rehaily, Joanna R Polsc, John R Porter, Jaber S Mossa, Bahar Ahmed. Three new diterpenes and the biological activity of different extracts of Jasonia montana. Natural product research. 2005 Apr; 19(3):253-65. doi: 10.1080/14786410410001712715. [PMID: 15702639]
R M Pérez G, R Vargas S, F J Martinez M, I Cordova R. Antioxidant and free radical scavenging activities of 5,7,3'-trihydroxy-3,6,4'-trimethoxyflavone from Brickellia veronicaefolia. Phytotherapy research : PTR. 2004 May; 18(5):428-30. doi: 10.1002/ptr.1445. [PMID: 15174007]
María José Abad, Paulina Bermejo, María Alvarez, José Antonio Guerra, Ana María Silván, Angel Maria Villar. Flavonoids and a sesquiterpene lactone from Tanacetum microphyllum inhibit anti-inflammatory mediators in LPS-stimulated mouse peritoneal macrophages. Planta medica. 2004 Jan; 70(1):34-8. doi: 10.1055/s-2004-815452. [PMID: 14765290]
Christophe Long, Pierre Sauleau, Bruno David, Catherine Lavaud, Valérie Cassabois, Frédéric Ausseil, Georges Massiot. Bioactive flavonoids of Tanacetum parthenium revisited. Phytochemistry. 2003 Sep; 64(2):567-9. doi: 10.1016/s0031-9422(03)00208-5. [PMID: 12943776]
Sabine Glasl, Pavel Mucaji, Ingrid Werner, Armin Presser, Johann Jurenitsch. Sesquiterpenes and flavonoid aglycones from a Hungarian taxon of the Achillea millefolium group. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2002 Nov; 57(11-12):976-82. doi: 10.1515/znc-2002-11-1203. [PMID: 12562079]
J C Meng, Y F Hu, J H Chen, R X Tan. Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa. Phytochemistry. 2001 Dec; 58(7):1141-5. doi: 10.1016/s0031-9422(01)00389-2. [PMID: 11730880]
L Muschietti, S Gorzalczany, G Ferraro, C Acevedo, V Martino. Phenolic compounds with anti-inflammatory activity from Eupatorium buniifolium. Planta medica. 2001 Nov; 67(8):743-4. doi: 10.1055/s-2001-18355. [PMID: 11731917]
R M Perez, H Cervantes, M A Zavala, J Sanchez, S Perez, C Perez. Isolation and hypoglycemic activity of 5, 7,3'-trihydroxy-3,6,4'-trimethoxyflavone from Brickellia veronicaefolia. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2000 Mar; 7(1):25-9. doi: 10.1016/s0944-7113(00)80018-5. [PMID: 10782487]
I Aljancić, V Vajs, N Menković, I Karadzić, N Juranić, S Milosavljević, S Macura. Flavones and sesquiterpene lactones from Achillea atrata subsp. multifida: antimicrobial activity. Journal of natural products. 1999 Jun; 62(6):909-11. doi: 10.1021/np980536m. [PMID: 10395518]
J J Lichius, O Thoison, A Montagnac, M Païs, F Guéritte-Voegelein, T Sévenet, J P Cosson, A H Hadi. Antimitotic and cytotoxic flavonols from Zieridium pseudobtusifolium and Acronychia porteri. Journal of natural products. 1994 Jul; 57(7):1012-6. doi: 10.1021/np50109a024. [PMID: 7964782]
M J Abad, P Bermejo, A Villar, S Valverde. Anti-inflammatory activity of two flavonoids from Tanacetum microphyllum. Journal of natural products. 1993 Jul; 56(7):1164-7. doi: 10.1021/np50097a022. [PMID: 8377020]