Xanthoangelol (BioDeep_00000395489)

 

Secondary id: BioDeep_00000265945

PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1/C25H28O4/c1-17(2)5-4-6-18(3)7-13-21-24(28)16-14-22(25(21)29)23(27)15-10-19-8-11-20(26)12-9-19/h5,7-12,14-16,26,28-29H,4,6,13H2,1-3H3/b15-10+,18-7

化学式: C25H28O4 (392.19874880000003)
中文名称: 黄色当归醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(O)=CC=C1/C=C/C(=O)C1C(O)=C(C/C=C(\C)/CC/C=C(\C)/C)C(O)=CC=1
InChI: InChI=1S/C25H28O4/c1-17(2)5-4-6-18(3)7-13-21-24(28)16-14-22(25(21)29)23(27)15-10-19-8-11-20(26)12-9-19/h5,7-12,14-16,26,28-29H,4,6,13H2,1-3H3/b15-10+,18-7+

描述信息

Xanthoangelol is a natural product found in Artocarpus altilis, Artocarpus nobilis, and other organisms with data available.
See also: Angelica keiskei top (part of); Angelica keiskei root (part of).
D004791 - Enzyme Inhibitors > D054328 - Proton Pump Inhibitors
Xanthoangelol, extracted from Angelica keiskei, suppresses obesity-induced inflammatory responses. Xanthoangelol possesses antibacterial activity[1][2]. Xanthoangelol inhibits monoamine oxidases[3]. Xanthoangelol induces apoptosis in neuroblastoma and leukemia cells[4].

同义名列表

16 个代谢物同义名

InChI=1/C25H28O4/c1-17(2)5-4-6-18(3)7-13-21-24(28)16-14-22(25(21)29)23(27)15-10-19-8-11-20(26)12-9-19/h5,7-12,14-16,26,28-29H,4,6,13H2,1-3H3/b15-10+,18-7; 2-PROPEN-1-ONE, 1-(3-((2E)-3,7-DIMETHYL-2,6-OCTADIEN-1-YL)-2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (2E)-; 2-Propen-1-one, 1-[3-[(2E)-3,7-dimethyl-2,6-octadienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)-, (2E)-; (2E)-1-(3-((2E)-3,7-DIMETHYL-2,6-OCTADIEN-1-YL)-2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-2-PROPEN-1-ONE; (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-bis(oxidanyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one; (2E)-1-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one; (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxy-phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one; 2-Propen-1-one, 1-(3-(3,7-dimethyl-2,6-octadienyl)-2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (E,E)-; (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)-2-propen-1-one; (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one; 1-[3-(3,7-Dimethyl-octa-2,6-dienyl)-2,4-dihydroxy-phenyl]-3-(4-hydroxy-phenyl)-propenone; CC(C)=CCCC(C)=CCc1c(O)ccc(C(=O)C=Cc2ccc(O)cc2)c1O; 2,4,4-Trihydroxy-3-geranylchalcone; UNII-91D4GN26Z1; Xanthoangelol; 91D4GN26Z1



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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)

0 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。



文献列表

  • Yasukiyo Yoshioka, Yumi Samukawa, Yoko Yamashita, Hitoshi Ashida. 4-Hydroxyderricin and xanthoangelol isolated from Angelica keiskei prevent dexamethasone-induced muscle loss. Food & function. 2020 Jun; 11(6):5498-5512. doi: 10.1039/d0fo00720j. [PMID: 32510085]
  • Dieter Meier, Melissa Vázquez Hernández, Lasse van Geelen, Rini Muharini, Peter Proksch, Julia E Bandow, Rainer Kalscheuer. The plant-derived chalcone Xanthoangelol targets the membrane of Gram-positive bacteria. Bioorganic & medicinal chemistry. 2019 12; 27(23):115151. doi: 10.1016/j.bmc.2019.115151. [PMID: 31648878]
  • Jia-Hao Lee, Hui-Ching Mei, I-Chih Kuo, Tzong-Huei Lee, Yu-Hsin Chen, Ching-Kuo Lee. Characterizing Tyrosinase Modulators from the Roots of Angelica keiskei Using Tyrosinase Inhibition Assay and UPLC-MS/MS as the Combinatorial Novel Approach. Molecules (Basel, Switzerland). 2019 Sep; 24(18):. doi: 10.3390/molecules24183297. [PMID: 31510069]
  • Daichi Kokubu, Ryousuke Ooba, Yukiko Abe, Hana Ishizaki, Shigeki Yoshida, Atsushi Asano, Shin-Ichi Kashiwabara, Hitoshi Miyazaki. Angelica keiskei (Ashitaba) powder and its functional compound xanthoangelol prevent heat stress-induced impairment in sperm density and quality in mouse testes. The Journal of reproduction and development. 2019 Apr; 65(2):139-146. doi: 10.1262/jrd.2018-141. [PMID: 30686791]
  • Tianshun Zhang, Qiushi Wang, Mangaladoss Fredimoses, Ge Gao, Keke Wang, Hanyong Chen, Ting Wang, Naomi Oi, Tatyana A Zykova, Kanamata Reddy, Ke Yao, Weiya Ma, Xiaoyu Chang, Mee-Hyun Lee, Moeez Ghani Rathore, Ann M Bode, Hitoshi Ashida, Scott M Lippman, Zigang Dong. The Ashitaba (Angelica keiskei) Chalcones 4-hydroxyderricin and Xanthoangelol Suppress Melanomagenesis By Targeting BRAF and PI3K. Cancer prevention research (Philadelphia, Pa.). 2018 10; 11(10):607-620. doi: 10.1158/1940-6207.capr-18-0092. [PMID: 29980517]
  • Lindsay K Caesar, Joshua J Kellogg, Olav M Kvalheim, Richard A Cech, Nadja B Cech. Integration of Biochemometrics and Molecular Networking to Identify Antimicrobials in Angelica keiskei. Planta medica. 2018 Jul; 84(9-10):721-728. doi: 10.1055/a-0590-5223. [PMID: 29571174]
  • Rini Muharini, Adriana Díaz, Weaam Ebrahim, Attila Mándi, Tibor Kurtán, Nidja Rehberg, Rainer Kalscheuer, Rudolf Hartmann, Raha S Orfali, Wenhan Lin, Zhen Liu, Peter Proksch. Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa. Journal of natural products. 2017 01; 80(1):169-180. doi: 10.1021/acs.jnatprod.6b00809. [PMID: 28075580]
  • Yongjia Li, Tsuyoshi Goto, Ryuma Ikutani, Shan Lin, Nobuyuki Takahashi, Haruya Takahashi, Huei-Fen Jheng, Rina Yu, Masahiko Taniguchi, Kimiye Baba, Shigeru Murakami, Teruo Kawada. Xanthoangelol and 4-hydroxyderrcin suppress obesity-induced inflammatory responses. Obesity (Silver Spring, Md.). 2016 11; 24(11):2351-2360. doi: 10.1002/oby.21611. [PMID: 27619735]
  • Yun-Seo Kil, Seul-Ki Choi, Yun-Sil Lee, Mahtab Jafari, Eun-Kyoung Seo. Chalcones from Angelica keiskei: Evaluation of Their Heat Shock Protein Inducing Activities. Journal of natural products. 2015 Oct; 78(10):2481-7. doi: 10.1021/acs.jnatprod.5b00633. [PMID: 26431394]
  • Maho Sumiyoshi, Masahiko Taniguchi, Kimiye Baba, Yoshiyuki Kimura. Antitumor and antimetastatic actions of xanthoangelol and 4-hydroxyderricin isolated from Angelica keiskei roots through the inhibited activation and differentiation of M2 macrophages. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Jul; 22(7-8):759-67. doi: 10.1016/j.phymed.2015.05.005. [PMID: 26141763]
  • Mitsuhiro Ohta, Aya Fujinami, Norihiro Kobayashi, Akiko Amano, Akihito Ishigami, Harukuni Tokuda, Nobutaka Suzuki, Fumitake Ito, Taisuke Mori, Morio Sawada, Koichi Iwasa, Jo Kitawaki, Katsunori Ohnishi, Muneo Tsujikawa, Hiroshi Obayashi. Two chalcones, 4-hydroxyderricin and xanthoangelol, stimulate GLUT4-dependent glucose uptake through the LKB1/AMP-activated protein kinase signaling pathway in 3T3-L1 adipocytes. Nutrition research (New York, N.Y.). 2015 Jul; 35(7):618-25. doi: 10.1016/j.nutres.2015.05.010. [PMID: 26077869]
  • Robert R Maronpot. Toxicological assessment of Ashitaba Chalcone. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2015 Mar; 77(?):111-9. doi: 10.1016/j.fct.2014.12.021. [PMID: 25576957]
  • Jin-Long Li, Li-Xin Gao, Fan-Wang Meng, Chun-Lan Tang, Ru-Jun Zhang, Jing-Ya Li, Cheng Luo, Jia Li, Wei-Min Zhao. PTP1B inhibitors from stems of Angelica keiskei (Ashitaba). Bioorganic & medicinal chemistry letters. 2015; 25(10):2028-32. doi: 10.1016/j.bmcl.2015.04.003. [PMID: 25891102]
  • Tianshun Zhang, Norio Yamamoto, Hitoshi Ashida. Chalcones suppress fatty acid-induced lipid accumulation through a LKB1/AMPK signaling pathway in HepG2 cells. Food & function. 2014 Jun; 5(6):1134-41. doi: 10.1039/c3fo60694e. [PMID: 24722377]
  • Dong Ju Son, Ye Oak Park, Chengguang Yu, Sung Eun Lee, Young Hyun Park. Bioassay-guided isolation and identification of anti-platelet-active compounds from the root of Ashitaba (Angelica keiskei Koidz.). Natural product research. 2014; 28(24):2312-6. doi: 10.1080/14786419.2014.931389. [PMID: 25019280]
  • Tianshun Zhang, Keisuke Sawada, Norio Yamamoto, Hitoshi Ashida. 4-Hydroxyderricin and xanthoangelol from Ashitaba (Angelica keiskei) suppress differentiation of preadiopocytes to adipocytes via AMPK and MAPK pathways. Molecular nutrition & food research. 2013 Oct; 57(10):1729-40. doi: 10.1002/mnfr.201300020. [PMID: 23681764]
  • Christian Limper, Yao Wang, Sven Ruhl, Zhiqiang Wang, Yijia Lou, Frank Totzke, Michael H G Kubbutat, Yvonni Chovolou, Peter Proksch, Wim Wätjen. Compounds isolated from Psoralea corylifolia seeds inhibit protein kinase activity and induce apoptotic cell death in mammalian cells. The Journal of pharmacy and pharmacology. 2013 Sep; 65(9):1393-408. doi: 10.1111/jphp.12107. [PMID: 23927478]
  • Toshiyuki Nakamura, Takahiro Tokushima, Kyuichi Kawabata, Norio Yamamoto, Masaaki Miyamoto, Hitoshi Ashida. Absorption and metabolism of 4-hydroxyderricin and xanthoangelol after oral administration of Angelica keiskei (Ashitaba) extract in mice. Archives of biochemistry and biophysics. 2012 May; 521(1-2):71-6. doi: 10.1016/j.abb.2012.03.013. [PMID: 22452965]
  • Hiromu Ohnogi, Yoko Kudo, Kenichi Tahara, Katsumi Sugiyama, Tatsuji Enoki, Shoko Hayami, Hiroaki Sagawa, Yuko Tanimura, Wataru Aoi, Yuji Naito, Ikunoshin Kato, Toshikazu Yoshikawa. Six new chalcones from Angelica keiskei inducing adiponectin production in 3T3-L1 adipocytes. Bioscience, biotechnology, and biochemistry. 2012; 76(5):961-6. doi: 10.1271/bbb.110976. [PMID: 22738967]
  • Naoki Ohkura, Yoshitaka Nakakuki, Masahiko Taniguchi, Shiho Kanai, Akiko Nakayama, Katsunori Ohnishi, Toshiyuki Sakata, Tomoyoshi Nohira, Juzo Matsuda, Kimiye Baba, Gen-Ichi Atsumi. Xanthoangelols isolated from Angelica keiskei inhibit inflammatory-induced plasminogen activator inhibitor 1 (PAI-1) production. BioFactors (Oxford, England). 2011 Nov; 37(6):455-61. doi: 10.1002/biof.187. [PMID: 22038782]
  • Kyuichi Kawabata, Keisuke Sawada, Kazunori Ikeda, Itsuko Fukuda, Kengo Kawasaki, Norio Yamamoto, Hitoshi Ashida. Prenylated chalcones 4-hydroxyderricin and xanthoangelol stimulate glucose uptake in skeletal muscle cells by inducing GLUT4 translocation. Molecular nutrition & food research. 2011 Mar; 55(3):467-75. doi: 10.1002/mnfr.201000267. [PMID: 20938990]
  • Maya Mori-Hongo, Hiromi Yamaguchi, Tsutomu Warashina, Toshio Miyase. Melanin synthesis inhibitors from Lespedeza cyrtobotrya. Journal of natural products. 2009 Jan; 72(1):63-71. doi: 10.1021/np800535g. [PMID: 19102656]
  • Nguyen Tien Dat, Jeong-Hyung Lee, Kyeong Lee, Young-Soo Hong, Young Ho Kim, Jung Joon Lee. Phenolic constituents of Amorpha fruticosa that inhibit NF-kappaB activation and related gene expression. Journal of natural products. 2008 Oct; 71(10):1696-700. doi: 10.1021/np800383q. [PMID: 18841906]
  • Nobuwa Aoki, Mai Muko, Emi Ohta, Shinji Ohta. C-geranylated chalcones from the stems of Angelica keiskei with superoxide-scavenging activity. Journal of natural products. 2008 Jul; 71(7):1308-10. doi: 10.1021/np800187f. [PMID: 18558745]
  • Kou Motani, Keiichi Tabata, Yumiko Kimura, Soichiro Okano, Yasuko Shibata, Yoshimitsu Abiko, Hisashi Nagai, Toshihiro Akihisa, Takashi Suzuki. Proteomic analysis of apoptosis induced by xanthoangelol, a major constituent of Angelica keiskei, in neuroblastoma. Biological & pharmaceutical bulletin. 2008 Apr; 31(4):618-26. doi: 10.1248/bpb.31.618. [PMID: 18379052]
  • Hiroshi Ogawa, Yukiko Okada, Toshinori Kamisako, Kimiye Baba. Beneficial effect of xanthoangelol, a chalcone compound from Angelica keiskei, on lipid metabolism in stroke-prone spontaneously hypertensive rats. Clinical and experimental pharmacology & physiology. 2007 Mar; 34(3):238-43. doi: 10.1111/j.1440-1681.2007.04578.x. [PMID: 17250645]
  • Masato Sugii, Mamoru Ohkita, Masahiko Taniguchi, Kimiye Baba, Yu Kawai, Chiyoko Tahara, Masanori Takaoka, Yasuo Matsumura. Xanthoangelol D isolated from the roots of Angelica keiskei inhibits endothelin-1 production through the suppression of nuclear factor-kappaB. Biological & pharmaceutical bulletin. 2005 Apr; 28(4):607-10. doi: 10.1248/bpb.28.607. [PMID: 15802795]
  • Toshihiro Akihisa, Harukuni Tokuda, Motohiko Ukiya, Masao Iizuka, Stefan Schneider, Kazuya Ogasawara, Teruo Mukainaka, Kenji Iwatsuki, Takashi Suzuki, Hoyoku Nishino. Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects. Cancer letters. 2003 Nov; 201(2):133-7. doi: 10.1016/s0304-3835(03)00466-x. [PMID: 14607326]
  • Yoshiyuki Kimura, Kimiye Baba. Antitumor and antimetastatic activities of Angelica keiskei roots, part 1: Isolation of an active substance, xanthoangelol. International journal of cancer. 2003 Sep; 106(3):429-37. doi: 10.1002/ijc.11256. [PMID: 12845685]
  • T Fujita, S Sakuma, T Sumiya, H Nishida, Y Fujimoto, K Baba, M Kozawa. The effects of xanthoangelol E on arachidonic acid metabolism in the gastric antral mucosa and platelet of the rabbit. Research communications in chemical pathology and pharmacology. 1992 Aug; 77(2):227-40. doi: ". [PMID: 1439191]
  • Y Inamori, K Baba, H Tsujibo, M Taniguchi, K Nakata, M Kozawa. Antibacterial activity of two chalcones, xanthoangelol and 4-hydroxyderricin, isolated from the root of Angelica keiskei KOIDZUMI. Chemical & pharmaceutical bulletin. 1991 Jun; 39(6):1604-5. doi: 10.1248/cpb.39.1604. [PMID: 1934181]
  • L A Barness. Safety considerations with high ascorbic acid dosage. Annals of the New York Academy of Sciences. 1975 Sep; 258(?):523-8. doi: 10.1111/j.1749-6632.1975.tb29311.x. [PMID: 946]