Apiin (BioDeep_00000269952)

Main id: BioDeep_00000000228

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


7-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

化学式: C26H28O14 (564.1478988)
中文名称: 芹菜苷, 芹菜甙
谱图信息: 最多检出来源 Homo sapiens(natural_products) 0.17%

分子结构信息

SMILES: c(c13)c(OC(O4)C(OC(O5)C(O)C(O)(C5)CO)C(O)C(C(CO)4)O)cc(c(C(C=C(O3)c(c2)ccc(c2)O)=O)1)O
InChI: InChI=1S/C26H28O14/c27-8-18-20(32)21(33)22(40-25-23(34)26(35,9-28)10-36-25)24(39-18)37-13-5-14(30)19-15(31)7-16(38-17(19)6-13)11-1-3-12(29)4-2-11/h1-7,18,20-25,27-30,32-35H,8-10H2/t18-,20-,21+,22-,23+,24-,25+,26-/m1/s1

描述信息

Apiin is a beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4-dihydroxyflavon-7-yl moiety at the anomeric position. It has a role as an EC 3.2.1.18 (exo-alpha-sialidase) inhibitor and a plant metabolite. It is a beta-D-glucoside, a dihydroxyflavone and a glycosyloxyflavone. It is functionally related to an apigenin. It is a conjugate acid of an apiin(1-).
Apiin is a natural product found in Crotalaria micans, Limonium axillare, and other organisms with data available.
See also: Chamomile (part of); Chamaemelum nobile flower (part of).
A beta-D-glucoside having a beta-D-apiosyl residue at the 2-position and a 5,4-dihydroxyflavon-7-yl moiety at the anomeric position.
Apiin, a major constituent of Apium graveolens leaves with anti-inflammatory properties. Apiin shows significant inhibitory activity on nitrite (NO) production (IC50 = 0.08 mg/mL) in-vitro and iNOS expression (IC50 = 0.049 mg/ mL) in LPS-activated J774.A1 cells[1].
Apiin, a major constituent of Apium graveolens leaves with anti-inflammatory properties. Apiin shows significant inhibitory activity on nitrite (NO) production (IC50 = 0.08 mg/mL) in-vitro and iNOS expression (IC50 = 0.049 mg/ mL) in LPS-activated J774.A1 cells[1].

同义名列表

41 个代谢物同义名

7-(((2S,3R,4S,5S,6R)-3-(((2S,3R,4R)-3,4-Dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 7-{[(2S,3R,4S,5S,6R)-3-{[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 7-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one; 7-[(2S,3R,4S,5S,6R)-3-[(3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one; 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]-beta-D-glucopyranoside; 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)-beta-D-glucopyranoside; 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 3-C-(hydroxymethyl)-beta-D-glycero-tetrofuranosyl-(1->2)-beta-D-glucopyranoside; 7-((2-O-D-APIO-.BETA.-D-FURANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)- 5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE; 4H-1-Benzopyran-4-one, 7-[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-; 7-((2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one; 7-[(2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]-5-hydroxy-2-(4-hydroxy-phenyl)-4H-1-benzopyran-4-one; 7-((2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-((2-O-.BETA.-D-APIOFURANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-5- HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRANONE; 7-((2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyranone; 7-O-(beta-D-apiofuranosyl-(1-2)-beta-D-glucosyl)-5,7,4-trihydroxyflavone; 7-O-(beta-D-Apiofuranosyl-1,2-beta-D-glucosyl)-5,7,4-trihydroxyflavone; 5,7,4-trihydroxyflavone 7-O-(beta-D-apiosyl-(1->2)-beta-D-glucoside); 5,7,4-trihydroxyflavone 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]; 7-O-(beta-D-apiofuranosyl-(1-2)-beta-D-glucosyl)-apigenin; apigenin 7-O-(beta-D-apiosyl-(1->2)-beta-D-glucoside); Apigenin 7-O-[beta-D-apiosyl-(1->2)-beta-D-glucoside]; NTDLXWMIWOECHG-YRCFQSNFSA-N; Apigenin-7-apioglucoside; Spectrum2_001800; Spectrum3_001787; Spectrum5_000553; Spectrum4_001817; UNII-6QU3EZE37U; DivK1c_007035; 6-acetylapiin; KBio2_003252; KBio3_002815; KBio1_001979; KBio2_005820; KBio2_000684; APIIN [MI]; Apiin (11); 6QU3EZE37U; Apioside; Apiin; 7- [ (2-O-D-Apio-beta-D-furanosyl-beta-D-glucopyranosyl) oxy ] -5-hydroxy-2- (4-hydroxyphenyl) -4H-1-benzopyran-4-one



数据库引用编号

35 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)

19 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

  • Maho Yamashita, Tae Fujimori, Song An, Sho Iguchi, Yuto Takenaka, Hiroyuki Kajiura, Takuya Yoshizawa, Hiroyoshi Matsumura, Masaru Kobayashi, Eiichiro Ono, Takeshi Ishimizu. The apiosyltransferase celery UGT94AX1 catalyzes the biosynthesis of the flavone glycoside apiin. Plant physiology. 2023 Jul; ?(?):. doi: 10.1093/plphys/kiad402. [PMID: 37433052]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Valentina Roviello, Melinda Gilhen-Baker, Caterina Vicidomini, Giovanni N Roviello. The Healing Power of Clean Rivers: In Silico Evaluation of the Antipsoriatic Potential of Apiin and Hyperoside Plant Metabolites Contained in River Waters. International journal of environmental research and public health. 2022 02; 19(5):. doi: 10.3390/ijerph19052502. [PMID: 35270196]
  • Neide Mara de Menezes Epifanio, Lynn Rykiel Iglesias Cavalcanti, Karine Falcão Dos Santos, Priscila Soares Coutinho Duarte, Piotr Kachlicki, Marcin Ożarowski, Cristiano Jorge Riger, Douglas Siqueira de Almeida Chaves. Chemical characterization and in vivo antioxidant activity of parsley (Petroselinum crispum) aqueous extract. Food & function. 2020 Jun; 11(6):5346-5356. doi: 10.1039/d0fo00484g. [PMID: 32462155]
  • Izabela Szymborska-Sandhu, Jarosław L Przybył, Olga Kosakowska, Katarzyna Bączek, Zenon Węglarz. Chemical Diversity of Bastard Balm (Melittis melisophyllum L.) as Affected by Plant Development. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102421. [PMID: 32455929]
  • Yearam Jung, Soon Young Shin, Yeonjoong Yong, Hyeryoung Jung, Seunghyun Ahn, Young Han Lee, Yoongho Lim. Plant-derived flavones as inhibitors of aurora B kinase and their quantitative structure-activity relationships. Chemical biology & drug design. 2015 May; 85(5):574-85. doi: 10.1111/cbdd.12445. [PMID: 25298094]
  • Peng Li, Jia Jia, Daihui Zhang, Jingli Xie, Xueshu Xu, Dongzhi Wei. In vitro and in vivo antioxidant activities of a flavonoid isolated from celery (Apium graveolens L. var. dulce). Food & function. 2014 Jan; 5(1):50-6. doi: 10.1039/c3fo60273g. [PMID: 24232123]
  • Douglas S A Chaves, Flávia S Frattani, Mariane Assafim, Ana Paula de Almeida, Russolina B de Zingali, Sônia S Costa. Phenolic chemical composition of Petroselinum crispum extract and its effect on haemostasis. Natural product communications. 2011 Jul; 6(7):961-4. doi: . [PMID: 21834233]
  • Kailan Zhou, Feng Zhao, Zhihui Liu, Yulei Zhuang, Lixia Chen, Feng Qiu. Triterpenoids and flavonoids from celery (Apium graveolens). Journal of natural products. 2009 Sep; 72(9):1563-7. doi: 10.1021/np900117v. [PMID: 19778086]
  • J Kasthuri, S Veerapandian, N Rajendiran. Biological synthesis of silver and gold nanoparticles using apiin as reducing agent. Colloids and surfaces. B, Biointerfaces. 2009 Jan; 68(1):55-60. doi: 10.1016/j.colsurfb.2008.09.021. [PMID: 18977643]
  • Ai-Lin Liu, Bo Liu, Hai-Lin Qin, Simon Mingyuen Lee, Yi-Tao Wang, Guan-Hua Du. Anti-influenza virus activities of flavonoids from the medicinal plant Elsholtzia rugulosa. Planta medica. 2008 Jun; 74(8):847-51. doi: 10.1055/s-2008-1074558. [PMID: 18553272]
  • M Lechtenberg, S Zumdick, C Gerhards, T J Schmidt, A Hensel. Evaluation of analytical markers characterising different drying methods of parsley leaves (Petroselinum crispum L.). Die Pharmazie. 2007 Dec; 62(12):949-54. doi: ". [PMID: 18214349]
  • T Mencherini, A Cau, G Bianco, R Della Loggia, R P Aquino, G Autore. An extract of Apium graveolens var. dulce leaves: structure of the major constituent, apiin, and its anti-inflammatory properties. The Journal of pharmacy and pharmacology. 2007 Jun; 59(6):891-7. doi: 10.1211/jpp.59.6.0016. [PMID: 17637182]
  • Ya-li Zong, Yu-ping Lin, Qiong-e Ding, Hui He, Gao-xiong Rao. [Studies on the chemical constituents of the aerial parts of Seseli mairei]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Jan; 30(1):42-4. doi: . [PMID: 17539301]
  • Hellen Meyer, Adrian Bolarinwa, Guenther Wolfram, Jakob Linseisen. Bioavailability of apigenin from apiin-rich parsley in humans. Annals of nutrition & metabolism. 2006; 50(3):167-72. doi: 10.1159/000090736. [PMID: 16407641]
  • Botros R Mikhaeil, Farid A Badria, Galal T Maatooq, Mohamed M A Amer. Antioxidant and immunomodulatory constituents of henna leaves. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Jul; 59(7-8):468-76. doi: 10.1515/znc-2004-7-803. [PMID: 15813363]
  • M Yoshikawa, T Uemura, H Shimoda, A Kishi, Y Kawahara, H Matsuda. Medicinal foodstuffs. XVIII. Phytoestrogens from the aerial part of Petroselinum crispum MIll. (Parsley) and structures of 6"-acetylapiin and a new monoterpene glycoside, petroside. Chemical & pharmaceutical bulletin. 2000 Jul; 48(7):1039-44. doi: 10.1248/cpb.48.1039. [PMID: 10923837]