Spiraeoside (BioDeep_00000398273)

Secondary id: BioDeep_00000017644, BioDeep_00000270741

natural product PANOMIX_OTCML-2023

代谢物信息卡片

Quercetin 4-glucoside

化学式: C21H20O12 (464.09547200000003)
中文名称: 螺旋藻甙, 绣线菊甙
谱图信息: 最多检出来源 Viridiplantae(plant) 0.33%

分子结构信息

SMILES: C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)OC4C(C(C(C(O4)CO)O)O)O
InChI: InChI=1/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1

描述信息

Acquisition and generation of the data is financially supported in part by CREST/JST.

同义名列表

3 个代谢物同义名

Spiraeoside; Quercetin 4-glucoside; quercetin-4-glucoside

数据库引用编号

29 个数据库交叉引用编号

ChEBI: CHEBI:75839
PubChem: 5320844
Metlin: METLIN50600
ChEMBL: CHEMBL402947
CAS: 20229-56-5
MoNA: PS086901
MoNA: PS086902
MoNA: PS086903
MoNA: PS086904
MoNA: PS086905
MoNA: PS086906
MoNA: PS086907
MoNA: PS086908
MoNA: PS086909
MoNA: PS086910
MoNA: PS086911
MoNA: CCMSLIB00004684242
MoNA: CCMSLIB00004684184
MoNA: PM017606
MoNA: MetaboBASE0315
MoNA: MetaboBASE0314
MoNA: MetaboBASE0313
MoNA: MetaboBASE0312
MoNA: MetaboBASE0311
MoNA: PT208690
MoNA: PT108690
MoNA: PR100814
MoNA: PR100365
MoNA: PR020081

分类词条

黄酮醇

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)

24 个相关的物种来源信息

1476995 - Allium ascalonicum:
4679 - Allium cepa:
446321 - Althaea armeniaca: 10.1007/BF02319718
446322 - Althaea cannabina: 10.1007/BF02319718
145745 - Althaea officinalis: 10.1007/BF02319718
49045 - Anaphalis margaritacea: 10.1007/S10600-009-9411-1
7091 - Bombyx mori: 10.1271/BBB.66.1396
337351 - Erodium arborescens: 10.1016/0031-9422(83)80148-4
337368 - Erodium crassifolium: 10.1016/0031-9422(83)80148-4
34316 - Eucalyptus camaldulensis:
34317 - Eucalyptus globulus: 10.1271/BBB.80832
627158 - Eucalyptus robusta: 10.1016/0031-9422(93)85448-Z
57917 - Filipendula ulmaria:
32228 - Filipendula vulgaris: 10.1016/J.FITOTE.2007.01.004
122183 - Geranium robertianum: 10.1055/S-0032-1321052
13547 - Gerbera jamesonii: 10.1016/S0031-9422(00)84090-X
3486 - Humulus lupulus: 10.1002/ELPS.200500714
35883 - Ipomoea nil: 10.1016/S0031-9422(00)90588-0
141191 - Lawsonia inermis: 10.1016/J.BMCL.2015.04.052
174664 - Lysimachia thyrsiflora: 10.1007/BF00579657
23029 - Sedum album: 10.1016/S0031-9422(00)97941-X
49843 - Spartium junceum: 10.1016/S0378-8741(00)00327-5
3902 - Ulex europaeus: 10.1016/S0031-9422(00)82823-X
183290 - Ulex gallii: 10.1016/S0031-9422(00)82823-X

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

Arti Nile, Shivraj Hariram Nile, Carlos L Cespedes-Acuña, Jae-Wook Oh. Spiraeoside extracted from red onion skin ameliorates apoptosis and exerts potent antitumor, antioxidant and enzyme inhibitory effects. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2021 Aug; 154(?):112327. doi: 10.1016/j.fct.2021.112327. [PMID: 34116102]
Maël Gainche, Clémence Ogeron, Isabelle Ripoche, François Senejoux, Juliette Cholet, Caroline Decombat, Laetitia Delort, Jean-Yves Berthon, Etienne Saunier, Florence Caldefie Chezet, Pierre Chalard. Xanthine Oxidase Inhibitors from Filipendula ulmaria (L.) Maxim. and Their Efficient Detections by HPTLC and HPLC Analyses. Molecules (Basel, Switzerland). 2021 Mar; 26(7):. doi: 10.3390/molecules26071939. [PMID: 33808360]
Keshab Kumar Karna, Bo Ram Choi, Jae Hyung You, Yu Seob Shin, Wan Shou Cui, Sung Won Lee, Ji Hoon Kim, Chul Young Kim, Hye Kyung Kim, Jong Kwan Park. The ameliorative effect of monotropein, astragalin, and spiraeoside on oxidative stress, endoplasmic reticulum stress, and mitochondrial signaling pathway in varicocelized rats. BMC complementary and alternative medicine. 2019 Nov; 19(1):333. doi: 10.1186/s12906-019-2736-9. [PMID: 31771569]
Kayako Ogi, Hidenobu Sumitani. Elucidation of an α-glucosidase inhibitor from the peel of Allium cepa by principal component analysis. Bioscience, biotechnology, and biochemistry. 2019 Apr; 83(4):751-754. doi: 10.1080/09168451.2018.1564619. [PMID: 30621512]
Gabriele Rocchetti, Francesca Blasi, Domenico Montesano, Silvia Ghisoni, Maria Carla Marcotullio, Stefano Sabatini, Lina Cossignani, Luigi Lucini. Impact of conventional/non-conventional extraction methods on the untargeted phenolic profile of Moringa oleifera leaves. Food research international (Ottawa, Ont.). 2019 01; 115(?):319-327. doi: 10.1016/j.foodres.2018.11.046. [PMID: 30599948]
Katarzyna Grzelak-Błaszczyk, Joanna Milala, Monika Kosmala, Krzysztof Kołodziejczyk, Michał Sójka, Andrzej Czarnecki, Robert Klewicki, Jerzy Juśkiewicz, Bartosz Fotschki, Adam Jurgoński. Onion quercetin monoglycosides alter microbial activity and increase antioxidant capacity. The Journal of nutritional biochemistry. 2018 06; 56(?):81-88. doi: 10.1016/j.jnutbio.2018.02.002. [PMID: 29518727]
Loretta Pobłocka-Olech, Daniel Głód, Maria E Żebrowska, Małgorzata Sznitowska, Miroslawa Krauze-Baranowska. TLC determination of flavonoids from different cultivars of Allium cepa and Allium ascalonicum. Acta pharmaceutica (Zagreb, Croatia). 2016 Dec; 66(4):543-554. doi: 10.1515/acph-2016-0038. [PMID: 27749248]
Yasuaki Kashino, Kaeko Murota, Namiko Matsuda, Muneaki Tomotake, Takuya Hamano, Rie Mukai, Junji Terao. Effect of Processed Onions on the Plasma Concentration of Quercetin in Rats and Humans. Journal of food science. 2015 Nov; 80(11):H2597-602. doi: 10.1111/1750-3841.13079. [PMID: 26375490]
Souichi Nakashima, Yoshimi Oda, Seikou Nakamura, Jiang Liu, Koko Onishi, Miki Kawabata, Hisako Miki, Yugo Himuro, Masayuki Yoshikawa, Hisashi Matsuda. Inhibitors of melanogenesis in B16 melanoma 4A5 cells from flower buds of Lawsonia inermis (Henna). Bioorganic & medicinal chemistry letters. 2015 Jul; 25(13):2702-6. doi: 10.1016/j.bmcl.2015.04.052. [PMID: 25987378]
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]
Si-Hwan Park, Hyun Jung Kim, Soon-Ho Yim, Ah-Ra Kim, Nisha Tyagi, Haihong Shen, Kyung Keun Kim, Boo Ahn Shin, Da-Woon Jung, Darren R Williams. Delineation of the role of glycosylation in the cytotoxic properties of quercetin using novel assays in living vertebrates. Journal of natural products. 2014 Nov; 77(11):2389-96. doi: 10.1021/np500231g. [PMID: 25397870]
Soumendranath Bhakat, Wilson Karubiu, Venkatesan Jayaprakash, Mahmoud E S Soliman. A perspective on targeting non-structural proteins to combat neglected tropical diseases: Dengue, West Nile and Chikungunya viruses. European journal of medicinal chemistry. 2014 Nov; 87(?):677-702. doi: 10.1016/j.ejmech.2014.10.010. [PMID: 25305334]
Takahiro Shibata, Fumie Nakashima, Kazuya Honda, Yu-Jhang Lu, Tatsuhiko Kondo, Yusuke Ushida, Koichi Aizawa, Hiroyuki Suganuma, Sho Oe, Hiroshi Tanaka, Takashi Takahashi, Koji Uchida. Toll-like receptors as a target of food-derived anti-inflammatory compounds. The Journal of biological chemistry. 2014 Nov; 289(47):32757-72. doi: 10.1074/jbc.m114.585901. [PMID: 25294874]
Qun Sun, Ye Lu, Shuang-Qing Wu, Shi Yao, Jian Zhang. [Study on the chemical constituents from Gnaphalium hypoleucum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Apr; 35(4):566-8. doi: ". [PMID: 23019902]
Sadaf Naeem, Peter Hylands, David Barlow. Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase. Bioorganic & medicinal chemistry. 2012 Feb; 20(3):1251-8. doi: 10.1016/j.bmc.2011.12.033. [PMID: 22261024]
Di Wu, Mian Zhang, Chaofeng Zhang, Zhengtao Wang. [Flavonoids and phenolic acid derivatives from flos farfarae]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 May; 35(9):1142-4. doi: 10.4268/cjcmm20100912. [PMID: 20707069]
Xianglan Piao, Yanze Tian, Xiaoyuan Mi, Jian Cui. [Tyrosinase inhibition of Potentilla bifurca]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Aug; 34(15):1952-4. doi: ". [PMID: 19894542]
Danuta Zielinska, Wieslaw Wiczkowski, Mariusz Konrad Piskula. Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods. Journal of agricultural and food chemistry. 2008 May; 56(10):3524-31. doi: 10.1021/jf073521f. [PMID: 18454541]
Brigitte A Graf, William Mullen, Stuart T Caldwell, Richard C Hartley, Garry G Duthie, Michael E J Lean, Alan Crozier, Christine A Edwards. Disposition and metabolism of [2-14C]quercetin-4'-glucoside in rats. Drug metabolism and disposition: the biological fate of chemicals. 2005 Jul; 33(7):1036-43. doi: 10.1124/dmd.104.002691. [PMID: 15833931]
G P Hubbard, S Wolffram, J A Lovegrove, J M Gibbins. Ingestion of quercetin inhibits platelet aggregation and essential components of the collagen-stimulated platelet activation pathway in humans. Journal of thrombosis and haemostasis : JTH. 2004 Dec; 2(12):2138-45. doi: 10.1111/j.1538-7836.2004.01067.x. [PMID: 15613018]
Ilja C W Arts, Aloys L A Sesink, Maria Faassen-Peters, Peter C H Hollman. The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides. The British journal of nutrition. 2004 Jun; 91(6):841-7. doi: 10.1079/bjn20041123. [PMID: 15182387]
Kaeko Murota, Yuki Mitsukuni, Mami Ichikawa, Tojiro Tsushida, Sayuri Miyamoto, Junji Terao. Quercetin-4'-glucoside is more potent than quercetin-3-glucoside in protection of rat intestinal mucosa homogenates against iron ion-induced lipid peroxidation. Journal of agricultural and food chemistry. 2004 Apr; 52(7):1907-12. doi: 10.1021/jf035151a. [PMID: 15053527]
Yoshiaki Amakura, Tomoaki Tsutsumi, Kumiko Sasaki, Takashi Yoshida, Tamio Maitani. Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Biological & pharmaceutical bulletin. 2003 Dec; 26(12):1754-60. doi: 10.1248/bpb.26.1754. [PMID: 14646185]
William Mullen, Brigitte A Graf, Stuart T Caldwell, Richard C Hartley, Garry G Duthie, Christine A Edwards, Michael E J Lean, Alan Crozier. Determination of flavonol metabolites in plasma and tissues of rats by HPLC-radiocounting and tandem mass spectrometry following oral ingestion of [2-(14)C]quercetin-4'-glucoside. Journal of agricultural and food chemistry. 2002 Nov; 50(23):6902-9. doi: 10.1021/jf020598p. [PMID: 12405795]
A L Sesink, K A O'Leary, P C Hollman. Quercetin glucuronides but not glucosides are present in human plasma after consumption of quercetin-3-glucoside or quercetin-4'-glucoside. The Journal of nutrition. 2001 Jul; 131(7):1938-41. doi: 10.1093/jn/131.7.1938. [PMID: 11435510]
E U Graefe, J Wittig, S Mueller, A K Riethling, B Uehleke, B Drewelow, H Pforte, G Jacobasch, H Derendorf, M Veit. Pharmacokinetics and bioavailability of quercetin glycosides in humans. Journal of clinical pharmacology. 2001 May; 41(5):492-9. doi: 10.1177/00912700122010366. [PMID: 11361045]
J M Gee, M S DuPont, A J Day, G W Plumb, G Williamson, I T Johnson. Intestinal transport of quercetin glycosides in rats involves both deglycosylation and interaction with the hexose transport pathway. The Journal of nutrition. 2000 Nov; 130(11):2765-71. doi: 10.1093/jn/130.11.2765. [PMID: 11053519]
M R Olthof, P C Hollman, T B Vree, M B Katan. Bioavailabilities of quercetin-3-glucoside and quercetin-4'-glucoside do not differ in humans. The Journal of nutrition. 2000 May; 130(5):1200-3. doi: 10.1093/jn/130.5.1200. [PMID: 10801919]
P C Hollman, M N Bijsman, Y van Gameren, E P Cnossen, J H de Vries, M B Katan. The sugar moiety is a major determinant of the absorption of dietary flavonoid glycosides in man. Free radical research. 1999 Dec; 31(6):569-73. doi: 10.1080/10715769900301141. [PMID: 10630681]
A A Aziz, C A Edwards, M E Lean, A Crozier. Absorption and excretion of conjugated flavonols, including quercetin-4'-O-beta-glucoside and isorhamnetin-4'-O-beta-glucoside by human volunteers after the consumption of onions. Free radical research. 1998 Sep; 29(3):257-69. doi: 10.1080/10715769800300291. [PMID: 9802557]
G Williamson, G W Plumb, Y Uda, K R Price, M J Rhodes. Dietary quercetin glycosides: antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells. Carcinogenesis. 1996 Nov; 17(11):2385-7. doi: 10.1093/carcin/17.11.2385. [PMID: 8968052]
P C Hollman, M vd Gaag, M J Mengelers, J M van Trijp, J H de Vries, M B Katan. Absorption and disposition kinetics of the dietary antioxidant quercetin in man. Free radical biology & medicine. 1996; 21(5):703-7. doi: 10.1016/0891-5849(96)00129-3. [PMID: 8891673]
P Poukens-Renwart, M Tits, J N Wauters, L Angenot. Densitometric evaluation of spiraeoside after derivatization in flowers of Filipendula ulmaria (L.) Maxim. Journal of pharmaceutical and biomedical analysis. 1992 Oct; 10(10-12):1085-8. doi: 10.1016/0731-7085(91)80125-s. [PMID: 1298367]