Xanthomicrol (BioDeep_00000009919)

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-

化学式: C18H16O7 (344.0895986)
中文名称: 黄姜味草醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(c(c2c(c1OC)oc(cc2=O)c1ccc(cc1)O)O)OC)OC
InChI: InChI=1S/C18H16O7/c1-22-16-14(21)13-11(20)8-12(9-4-6-10(19)7-5-9)25-15(13)17(23-2)18(16)24-3/h4-8,19,21H,1-3H3

描述信息

Isolated from Citrus sudachi, Mentha piperita, Sideritis subspecies and Thymus subspecies Xanthomicrol is found in many foods, some of which are citrus, herbs and spices, sweet basil, and winter savory.
low.

同义名列表

5 个代谢物同义名

4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-; 5-Hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-one; 5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one; 4,5-Dihydroxy-6,7,8-trimethoxyflavone; Xanthomicrol

数据库引用编号

14 个数据库交叉引用编号

ChEBI: CHEBI:35047
KEGG: C14476
PubChem: 73207
HMDB: HMDB0037600
Metlin: METLIN49870
ChEMBL: CHEMBL476121
LipidMAPS: LMPK12111447
KNApSAcK: C00003879
foodb: FDB016712
chemspider: 65965
CAS: 16545-23-6
PMhub: MS000023741
PubChem: 17395476
NIKKAJI: J14.449E

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)

75 个相关的物种来源信息

204144 Ocimum gratissimum:
171251 Citrus medica:
558546 Citrus sudachi:
2707514 Baccharis quitensis:
39350 Ocimum basilicum:
204141 Ocimum americanum:
1548556 Chiliadenus iphionoides:
155258 Sideritis pungens:
63803 Siparuna: 10.1016/0031-9422(93)85293-Z
125667 Xerochrysum viscosum: 10.1016/0031-9422(93)85293-Z
1392562 Olearia heterocarpa: 10.1071/CH9712621
546409 Satureja cuneifolia: 10.3109/13880208709055202
751874 Thymus saturejoides: 10.1055/S-2007-969583
49992 Thymus vulgaris: 10.1080/00021369.1989.10869758
1391983 Stachys schtschegleevii: 10.1016/J.BSE.2006.05.004
76707 Wilkesia hobdyi: 10.1016/0031-9422(90)85423-D
4263 Wilkesia gymnoxiphium: 10.1016/0031-9422(90)85423-D
76672 Argyroxiphium sandwicense: 10.1016/0031-9422(90)85423-D
1107925 Thymus herba-barona: 10.1016/0031-9422(95)00217-U
1391945 Sideritis leucantha:
751793 Clinopodium douglasii:
155232 Sideritis algarviensis: 10.1016/0305-1978(90)90068-Q
315439 Bellardia trixago: 10.3109/13880209009082777
1391947 Stachys aegyptiaca: 10.1016/S0031-9422(00)95197-5
59430 Helichrysum: 10.1515/ZNC-1992-1-203
200954 Ononis natrix: 10.1021/NP50119A018
1461643 Lavandula mairei var. mairei: 10.1016/S0305-1978(00)00013-2
309312 Ficus lyrata: 10.1080/10286020310001608958
45325 Bombax ceiba: 10.1080/14786419.2010.518146
2707489 Baccharis patens: 10.1021/NP50041A041
2024912 Dracocephalum multicaule: 10.1007/BF00630447
193336 Stachys chrysantha: 10.1248/BPB.23.47
2798873 Scutellaria drummondii: 10.1016/0031-9422(94)00531-W
180015 Dracocephalum kotschyi: 10.1016/J.PHYTOCHEM.2005.04.035
1550853 Brickellia paniculata:
2707841 Baccharis tucumanensis: 10.1016/0031-9422(82)85268-0
1461646 Lavandula pubescens: 10.1016/S0305-1978(99)00021-6
204144 Ocimum gratissimum:
171251 Citrus medica:
558546 Citrus sudachi:
2707514 Baccharis quitensis:
39350 Ocimum basilicum:
204141 Ocimum americanum:
1548556 Chiliadenus iphionoides:
155258 Sideritis pungens:
63803 Siparuna: 10.1016/0031-9422(93)85293-Z
125667 Xerochrysum viscosum: 10.1016/0031-9422(93)85293-Z
1392562 Olearia heterocarpa: 10.1071/CH9712621
546409 Satureja cuneifolia: 10.3109/13880208709055202
751874 Thymus saturejoides: 10.1055/S-2007-969583
49992 Thymus vulgaris: 10.1080/00021369.1989.10869758
1391983 Stachys schtschegleevii: 10.1016/J.BSE.2006.05.004
76707 Wilkesia hobdyi: 10.1016/0031-9422(90)85423-D
4263 Wilkesia gymnoxiphium: 10.1016/0031-9422(90)85423-D
76672 Argyroxiphium sandwicense: 10.1016/0031-9422(90)85423-D
1107925 Thymus herba-barona: 10.1016/0031-9422(95)00217-U
1391945 Sideritis leucantha:
751793 Clinopodium douglasii:
155232 Sideritis algarviensis: 10.1016/0305-1978(90)90068-Q
315439 Bellardia trixago: 10.3109/13880209009082777
1391947 Stachys aegyptiaca: 10.1016/S0031-9422(00)95197-5
59430 Helichrysum: 10.1515/ZNC-1992-1-203
200954 Ononis natrix: 10.1021/NP50119A018
1461643 Lavandula mairei var. mairei: 10.1016/S0305-1978(00)00013-2
309312 Ficus lyrata: 10.1080/10286020310001608958
45325 Bombax ceiba: 10.1080/14786419.2010.518146
2707489 Baccharis patens: 10.1021/NP50041A041
2024912 Dracocephalum multicaule: 10.1007/BF00630447
193336 Stachys chrysantha: 10.1248/BPB.23.47
2798873 Scutellaria drummondii: 10.1016/0031-9422(94)00531-W
180015 Dracocephalum kotschyi: 10.1016/J.PHYTOCHEM.2005.04.035
1550853 Brickellia paniculata:
2707841 Baccharis tucumanensis: 10.1016/0031-9422(82)85268-0
1461646 Lavandula pubescens: 10.1016/S0305-1978(99)00021-6
9606 Homo sapiens: -

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

Mariella Nieddu, Federica Pollastro, Paola Caria, Stefano Salamone, Antonella Rosa. Xanthomicrol Activity in Cancer HeLa Cells: Comparison with Other Natural Methoxylated Flavones. Molecules (Basel, Switzerland). 2023 Jan; 28(2):. doi: 10.3390/molecules28020558. [PMID: 36677614]
Ngoc Hong Nguyen, Qui Thanh Hoai Ta, Quang Thang Pham, Thi Ngoc Han Luong, Van Trung Phung, Thuc-Huy Duong, Van Giau Vo. Anticancer Activity of Novel Plant Extracts and Compounds from Adenosma bracteosum (Bonati) in Human Lung and Liver Cancer Cells. Molecules (Basel, Switzerland). 2020 Jun; 25(12):. doi: 10.3390/molecules25122912. [PMID: 32599892]
Ekaterina-Michaela Tomou, Maria V Chatziathanasiadou, Paschalina Chatzopoulou, Andreas G Tzakos, Helen Skaltsa. NMR-Based Chemical Profiling, Isolation and Evaluation of the Cytotoxic Potential of the Diterpenoid Siderol from Cultivated Sideritis euboea Heldr. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102382. [PMID: 32443927]
Ilias Stefanis, Dimitra Hadjipavlou-Litina, Anna-Rita Bilia, Anastasia Karioti. LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity. Planta medica. 2019 Aug; 85(11-12):941-946. doi: 10.1055/a-0927-7041. [PMID: 31163460]
Seyedeh-Somayeh Zamani, Mohsen Hossieni, Mahmoud Etebari, Pirooz Salehian, Soltan Ahmad Ebrahimi. Pharmacokinetics of calycopterin and xanthmicrol, two polymethoxylated hydroxyflavones with anti-angiogenic activities from Dracocephalum kotschyi Bioss. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2016 Oct; 24(1):22. doi: 10.1186/s40199-016-0161-x. [PMID: 27716340]
Fatma Pinar Turkmenoglu, İpek Baysal, Samiye Ciftci-Yabanoglu, Kemal Yelekci, Hamdi Temel, Salih Paşa, Nurten Ezer, İhsan Çalış, Gulberk Ucar. Flavonoids from Sideritis Species: Human Monoamine Oxidase (hMAO) Inhibitory Activities, Molecular Docking Studies and Crystal Structure of Xanthomicrol. Molecules (Basel, Switzerland). 2015 Apr; 20(5):7454-73. doi: 10.3390/molecules20057454. [PMID: 25915461]
Hassan Abbaszadeh, Soltan Ahmad Ebrahimi, Maziar Mohammad Akhavan. Antiangiogenic activity of xanthomicrol and calycopterin, two polymethoxylated hydroxyflavones in both in vitro and ex vivo models. Phytotherapy research : PTR. 2014 Nov; 28(11):1661-70. doi: 10.1002/ptr.5179. [PMID: 24895220]
Mohammad Fattahi, Rosa M Cusido, Abbas Khojasteh, Mercedes Bonfill, Javier Palazon. Xanthomicrol: a comprehensive review of its chemistry, distribution, biosynthesis and pharmacological activity. Mini reviews in medicinal chemistry. 2014; 14(9):725-33. doi: 10.2174/1389557514666140820122818. [PMID: 25138085]
Palatheeya Sujatha, Gandhe Sreekanth, Shaikh Khasim, Belvotagi Venkatrao Adavi Rao, Bobbala Ravi Kumar, Achanta Venkata Narasimha Appa Rao. Flavonoids of Dikamali: A phytochemical reinvestigation. Natural product research. 2013 Oct; 27(20):1930-2. doi: 10.1080/14786419.2013.782494. [PMID: 23537094]
Ghazaal Moghaddam, Soltan Ahmad Ebrahimi, Nahid Rahbar-Roshandel, Alireza Foroumadi. Antiproliferative activity of flavonoids: influence of the sequential methoxylation state of the flavonoid structure. Phytotherapy research : PTR. 2012 Jul; 26(7):1023-8. doi: 10.1002/ptr.3678. [PMID: 22184071]
Ahmad Reza Gohari, Seyed Nasser Ostad, Fahimeh Moradi-Afrapoli, Maryam Malmir, Shohreh Tavajohi, Hassan Akbari, Soodabeh Saeidnia. Evaluation of the cytotoxicity of Satureja spicigera and its main compounds. TheScientificWorldJournal. 2012; 2012(?):203861. doi: 10.1100/2012/203861. [PMID: 22623883]
Ali M El-Hagrassi, Mamdouh M Ali, Abeer F Osman, Mohamed Shaaban. Phytochemical investigation and biological studies of Bombax malabaricum flowers. Natural product research. 2011 Jan; 25(2):141-51. doi: 10.1080/14786419.2010.518146. [PMID: 21246441]
Esra Küpeli, F Pinar Sahin, Erdem Yeşilada, Ihsan Caliş, Nurten Ezer. In vivo anti-inflammatory and antinociceptive activity evaluation of phenolic compounds from Sideritis stricta. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 Jul; 62(7-8):519-25. doi: 10.1515/znc-2007-7-810. [PMID: 17913066]
Hector Ponce-Monter, Salud Perez, Miguel Angel Zavala, Cuauhtemoc Perez, Mariana Meckes, Arturo Macias, María Campos. Relaxant effect of xanthomicrol and 3alpha-angeloyloxy-2alpha-hydroxy-13,14z-dehydrocativic acid from Brickellia paniculata on rat uterus. Biological & pharmaceutical bulletin. 2006 Jul; 29(7):1501-3. doi: 10.1248/bpb.29.1501. [PMID: 16819199]
Fereshteh Jahaniani, Soltan Ahmed Ebrahimi, Nahid Rahbar-Roshandel, Massoud Mahmoudian. Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent. Phytochemistry. 2005 Jul; 66(13):1581-92. doi: 10.1016/j.phytochem.2005.04.035. [PMID: 15949825]
Soodabeh Saeidnia, Ahmad Reza Gohari, Michiho Ito, Fumiyuki Kiuchi, Gisho Honda. Bioactive constituents from Dracocephalum subcapitatum (O. Kuntze) Lipsky. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2005 Jan; 60(1-2):22-4. doi: 10.1515/znc-2005-1-204. [PMID: 15787238]
Fatma U Afifi, Talal Aburjai. Antiplatelet activity of Varthemia iphionoides. Fitoterapia. 2004 Dec; 75(7-8):629-33. doi: 10.1016/j.fitote.2004.04.014. [PMID: 15567236]
Roberto F Vieira, Renée J Grayer, Alan J Paton. Chemical profiling of Ocimum americanum using external flavonoids. Phytochemistry. 2003 Jul; 63(5):555-67. doi: 10.1016/s0031-9422(03)00143-2. [PMID: 12809716]
Mariana Meckes, Fernando Calzada, Daniel Paz, Jaime Rodríguez, Héctor Ponce-Monter. Inhibitory effect of xanthomicrol and 3 alpha-angeloyloxy-2 alpha-hydroxy-13,14Z-dehydrocativic acid from Brickellia paniculata on the contractility of guinea-pig ileum. Planta medica. 2002 May; 68(5):467-9. doi: 10.1055/s-2002-32092. [PMID: 12058331]
R J Grayer, N C Veitch, G C Kite, A M Price, T Kokubun. Distribution of 8-oxygenated leaf-surface flavones in the genus Ocimum. Phytochemistry. 2001 Mar; 56(6):559-67. doi: 10.1016/s0031-9422(00)00439-8. [PMID: 11281133]