Luteolin (BioDeep_00000017328)

Secondary id: BioDeep_00000000423, BioDeep_00000018820, BioDeep_00000403152

human metabolite PANOMIX_OTCML-2023 blood metabolite

代谢物信息卡片

(2S,3S,4S,5R,6S)-6-((2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

化学式: C21H18O12 (462.0798228)
中文名称: 木犀草素-7-O-葡萄糖醛酸苷, 木犀草素-7-葡萄糖醛酸苷
谱图信息: 最多检出来源 Viridiplantae(plant) 5.51%

分子结构信息

SMILES: C1(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](C(=O)O)O2)=CC2OC(C3C=C(O)C(O)=CC=3)=CC(=O)C=2C(O)=C1
InChI: InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

描述信息

Luteolin 7-O-beta-D-glucosiduronic acid is a luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position. It has a role as a metabolite. It is a trihydroxyflavone, a glycosyloxyflavone, a monosaccharide derivative and a luteolin O-glucuronoside. It is a conjugate acid of a luteolin 7-O-beta-D-glucosiduronate and a luteolin 7-O-beta-D-glucosiduronate(2-).
Luteolin 7-glucuronide is a natural product found in Galeopsis tetrahit, Galeopsis ladanum, and other organisms with data available.
A luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position.
Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.
Luteolin 7-O-glucuronide could inhibit Matrix Metalloproteinases (MMP) activities, with IC50s of 17.63, 7.99, 11.42, 12.85, 0.03 μM for MMP-1, MMP-3, MMP-8, MMP-9, MMP-13, respectively.

同义名列表

23 个代谢物同义名

(2S,3S,4S,5R,6S)-6-((2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid; (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-chromen-7-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid; (2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid; GLUCOPYRANOSIDURONIC ACID, 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-4-OXO-4H-1-BENZOPYRAN-7-YL, .BETA.-D-; .BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-4-OXO-4H-1-BENZOPYRAN-7-YL; 2-(3,4-DIHYDROXYPHENYL)-5-HYDROXY-4-OXO-4H-1-BENZOPYRAN-7-YL .BETA.-D-GLUCOPYRANOSIDURONIC ACID; beta-D-Glucopyranosiduronic acid, 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-1-benzopyran-7-yl; 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(.beta.-D-glucopyranuronosyloxy)-5-hydroxy-; 2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl beta-D-glucopyranosiduronic acid; FLAVONE, 3,4,5,7-TETRAHYDROXY-, 7-.BETA.-D-GLUCOPYRANURONOSIDE; Luteolin 7-O-beta-D-glucuronopyranoside; CYANIDENON-7-O-.BETA.-D-GLUCURONIC ACID; luteolin 7-O-beta-D-glucosiduronic acid; Cyanidenon-7-O-beta-D-glucuronic acid; Luteolin 7-O-beta-D-glucuronide (14); LUTEOLIN-7-.BETA.-D-GLUCURONIDE; Luteolin 7-O-beta-D-Glucuronide; Luteolin-7-O-glucuronside; Luteolin 7-O-glucuronide; luteolin-7-glucuronide; Luteolin 7-glucuronide; MEGxp0_000794; Luteolin

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:18128
KEGG: C03515
PubChem: 13607752
PubChem: 5280601
HMDB: HMDB0240541
ChEMBL: CHEMBL464224
LipidMAPS: LMPK12110644
MeSH: luteolin-7-glucuronide
ChemIDplus: 0029741104
chemspider: 4444211
CAS: 29741-10-4
medchemexpress: HY-N1463
MetaboLights: MTBLC18128
PubChem: 6324
KNApSAcK: C00004268
3DMET: B01665
NIKKAJI: J387.924K

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)

128 个相关的物种来源信息

13326 - Acanthus: 10.1016/S0031-9422(01)00306-5
241842 - Acanthus ebracteatus: 10.1016/S0031-9422(01)00306-5
282730 - Achillea collina: 10.3797/SCIPHARM.AUT-01-09
57912 - Agrimonia eupatoria: 10.1271/BBB.100200
4151 - Antirrhinum majus: 10.1016/S0031-9422(00)84856-6
7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
53173 - Betonica officinalis: 10.1016/J.PHYTOCHEM.2004.04.014
536997 - Callicarpa macrophylla Vahl: -
36622 - Chaenomeles sinensis: 10.1007/BF02977002
109094 - Chaerophyllum aureum:
146995 - Chrysanthemum indicum: 10.1248/CPB.47.340
146995 - Chrysanthemum indicum L.: -
13427 - Cichorium intybus:
4265 - Cynara cardunculus:
59895 - Cynara cardunculus var. scolymus: 10.1016/J.FOODCHEM.2005.01.013
4039 - Daucus carota: 10.1016/0031-9422(88)80745-3
56917 - Dumortiera hirsuta: 10.1016/0031-9422(96)00242-7
253483 - Fuchsia excorticata: 10.1016/0031-9422(83)80021-1
85206 - Fuchsia procumbens: 10.1016/0031-9422(83)80021-1
13070 - Fuchsia triphylla: 10.1016/0031-9422(83)80021-1
457138 - Galeopsis angustifolia: 10.1016/0031-9422(91)83199-U
572113 - Galeopsis bifida: 10.1016/0031-9422(91)83199-U
1030043 - Galeopsis ladanum: 10.1016/0031-9422(91)83199-U
457139 - Galeopsis pubescens: 10.1016/0031-9422(91)83199-U
1081551 - Galeopsis pyrenaica: 10.1016/0031-9422(91)83199-U
1081552 - Galeopsis segetum: 10.1016/0031-9422(91)83199-U
457140 - Galeopsis speciosa: 10.1016/0031-9422(91)83199-U
1000418 - Galeopsis tetrahit: 10.1016/0031-9422(91)83199-U
82755 - Gymnanthemum amygdalinum: 10.1021/JF00047A015
9606 - Homo sapiens: -
75953 - Lactuca indica:
268080 - Lapsana communis: 10.1515/ZNC-1998-11-1224
313095 - Lathyrus laxiflorus: 10.1016/0305-1978(93)90077-5
254779 - Lathyrus pratensis: 10.1016/0305-1978(93)90077-5
320345 - Lippia alba: 10.1016/J.JEP.2007.11.044
932105 - Lycopus americanus: 10.1055/S-2006-958111
1720382 - Lycopus asper: 10.1007/BF02980102
260603 - Lycopus europaeus:
260604 - Lycopus exaltatus: 10.1055/S-2006-958111
516551 - Lycopus lucidus: 10.1007/BF02980102
1620142 - Lycopus virginicus: 10.1055/S-2006-958111
3197 - Marchantia polymorpha: 10.1016/0031-9422(75)85194-6
3197 - Marchantia polymorpha: 10.1016/S0031-9422(97)00875-3
41230 - Marrubium vulgare: 10.1016/J.FOODCHEM.2011.07.112
70936 - Medicago arabica: 10.1016/0305-1978(82)90048-5
47084 - Medicago polymorpha: 10.1016/0305-1978(82)90048-5
70968 - Medicago radiata: 10.1016/0305-1978(82)90048-5
3879 - Medicago sativa: 10.1021/JF000876P
3880 - Medicago truncatula: 10.1021/JF063635B
1611021 - Meehania fargesii: 10.1248/CPB.58.696
672825 - Meehania urticifolia: 10.1007/S11418-010-0501-Y
182387 - Monarda punctata: 10.1016/J.PHYTOCHEM.2010.08.009
204144 - Ocimum gratissimum: 10.1002/1099-1565(200007/08)11:4<257::AID-PCA521>3.0.CO;2-A
39352 - Origanum vulgare:
388205 - Penstemon serrulatus: 10.1515/ZNC-1997-7-803
48386 - Perilla frutescens: 10.1248/BPB.25.1197
943712 - Phagnalon rupestre: 10.1016/S0031-9422(02)00011-0
255872 - Picria fel-terrae: 10.1016/S0031-9422(99)00242-3
255872 - Picria felterrae: 10.1016/S0031-9422(99)00242-3
26867 - Plantago: 10.1007/BF00564976
197796 - Plantago asiatica: 10.1086/325089
29818 - Plantago major:
33090 - Plants: -
57926 - Potentilla anserina: 10.1080/10286020.2010.489826
347942 - Pyrrosia serpens: 10.1016/0031-9422(90)85359-N
295715 - Rhizomnium magnifolium: 10.1515/ZNC-1986-11-1203
295714 - Rhizomnium pseudopunctatum: 10.1515/ZNC-1986-11-1203
41844 - Riccia fluitans: 10.1016/0031-9422(75)85037-0
41844 - Riccia fluitans: 10.1016/S0031-9422(00)81767-7
75099 - Rubus ulmifolius: 10.1016/S0378-8741(01)00363-4
268906 - Salvia fruticosa:
38868 - Salvia officinalis:
268920 - Salvia palaestina:
49216 - Salvia pratensis: 10.1016/S0031-9422(01)00415-0
41644 - Santolina chamaecyparissus: 10.1055/S-0028-1097749
200489 - Saussurea involucrata: 10.1002/RCM.7014
212686 - Scorzoneroides autumnalis: 10.1016/J.PHYTOCHEM.2005.10.019
50191 - Sonchus acaulis: 10.1016/0031-9422(83)83031-3
50192 - Sonchus arvensis:
50192 - Sonchus arvensis: 10.1016/0031-9422(83)83031-3
50193 - Sonchus asper: 10.1016/0031-9422(83)83031-3
381729 - Sonchus bipontini: 10.1016/0031-9422(83)83031-3
50195 - Sonchus brachylobus: 10.1016/0031-9422(83)83031-3
381730 - Sonchus brachyotus: 10.1016/0031-9422(83)83031-3
50196 - Sonchus canariensis: 10.1016/0031-9422(83)83031-3
50221 - Sonchus capillaris: 10.1016/0031-9422(83)83031-3
50197 - Sonchus congestus: 10.1016/0031-9422(83)83031-3
381731 - Sonchus crassifolius: 10.1016/0031-9422(83)83031-3
50199 - Sonchus fauces-orci: 10.1016/0031-9422(83)83031-3
50200 - Sonchus fruticosus: 10.1016/0031-9422(83)83031-3
50201 - Sonchus gandogeri: 10.1016/0031-9422(83)83031-3
1519691 - Sonchus gomerensis: 10.1016/0031-9422(83)83031-3
43192 - Sonchus grandifolius: 10.1016/0031-9422(83)83031-3
159710 - Sonchus gummifer: 10.1016/0031-9422(83)83031-3
50222 - Sonchus heterophyllus: 10.1016/0031-9422(83)83031-3
50203 - Sonchus hierrensis: 10.1016/0031-9422(83)83031-3
255580 - Sonchus hydrophilus: 10.1016/0031-9422(83)83031-3
50205 - Sonchus luxurians: 10.1016/0031-9422(83)83031-3
50206 - Sonchus maritimus: 10.1016/0031-9422(83)83031-3
381734 - Sonchus mauritanicus:
381734 - Sonchus mauritanicus: 10.1016/0031-9422(83)83031-3
329331 - Sonchus microcarpus: 10.1016/0031-9422(83)83031-3
50207 - Sonchus oleraceus:
50209 - Sonchus palmensis: 10.1016/0031-9422(83)83031-3
50211 - Sonchus pinnatifidus: 10.1016/0031-9422(83)83031-3
50212 - Sonchus pinnatus: 10.1016/0031-9422(83)83031-3
43190 - Sonchus platylepis: 10.1016/0031-9422(83)83031-3
332207 - Sonchus radicatus: 10.1016/0031-9422(83)83031-3
50224 - Sonchus regis-jubae: 10.1016/0031-9422(83)83031-3
50213 - Sonchus schweinfurthii: 10.1016/0031-9422(83)83031-3
255578 - Sonchus tenerrimus: 10.1016/0031-9422(83)83031-3
50215 - Sonchus ustulatus: 10.1016/0031-9422(83)83031-3
37410 - Sphaerocarpos texanus: 10.1016/S0031-9422(00)89073-1
467599 - Stachys alopecuros: 10.1016/J.PHYTOCHEM.2004.04.014
127999 - Tanacetum parthenium:
128002 - Tanacetum vulgare: 10.1016/S0031-9422(99)00021-7
49992 - Thymus vulgaris: 10.1021/NP010636J
79184 - Torilis arvensis: 10.1016/S0031-9422(00)84026-1
40891 - Torilis nodosa: 10.1016/S0031-9422(00)84026-1
79189 - Torilis tenella: 10.1016/S0031-9422(00)84026-1
97032 - Trifolium pannonicum: 10.1016/S0031-9422(00)97413-2
54463 - Tripora divaricata: 10.1016/S0031-9422(02)00192-9
163752 - Veronica parviflora: 10.1016/S0031-9422(00)00397-6
1367250 - Veronica strictissima: 10.1016/S0031-9422(00)00397-6
2820225 - Veronica traversii: 10.1016/S0031-9422(00)00397-6
204215 - Vitex trifolia: 10.4268/CJCMM20141115
89039 - Youngia japonica: 10.1248/CPB.57.719
33090 - 苦碟子: -

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

Jun Gu Kim, Jin Woo Lee, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Haeun Kwon, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang. Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production. Journal of natural products. 2021 03; 84(3):562-569. doi: 10.1021/acs.jnatprod.0c01121. [PMID: 33667099]
Xing Wang, Ying Li, Meiling Chen, Chunyan Li, Wei Huang, Kun Gu, Hongxin Yu, Yu Yuan, Yuming Wang, Bin Yang, Yubo Li. Stepwise rapid tracking strategy to identify active molecules from Ixeris sonchifolia Hance based on ''affinity mass spectrometry-atomic force microscopy imaging'' technology. Talanta. 2020 Sep; 217(?):121031. doi: 10.1016/j.talanta.2020.121031. [PMID: 32498901]
Jingyi Zhu, Han Xiao, Qi Chen, Min Zhao, Dong Sun, Shunshan Duan. Growth Inhibition of Phaeocystis Globosa Induced by Luteolin-7-O-glucuronide from Seagrass Enhalus acoroides. International journal of environmental research and public health. 2019 07; 16(14):. doi: 10.3390/ijerph16142615. [PMID: 31340457]
C T Sulaiman, Indira Balachandran. LC/MS characterization of phenolic antioxidants of Brindle berry (Garcinia gummi-gutta (L.) Robson). Natural product research. 2017 May; 31(10):1191-1194. doi: 10.1080/14786419.2016.1224871. [PMID: 27583573]
Peng-Fei Yang, Zi-Ming Feng, Ya-Nan Yang, Jian-Shuang Jiang, Pei-Cheng Zhang. Neuroprotective Caffeoylquinic Acid Derivatives from the Flowers of Chrysanthemum morifolium. Journal of natural products. 2017 04; 80(4):1028-1033. doi: 10.1021/acs.jnatprod.6b01026. [PMID: 28248102]
Fuad Al-Rimawi, Saleh Abu-Lafi, Jehad Abbadi, Ayman A A Alamarneh, Raneen A Sawahreh, Imad Odeh. ANALYSIS OF PHENOLIC AND FLAVONOIDS OF WILD EPHEDRA ALATA PLANT EXTRACTS BY LC/PDA AND LC/MS AND THEIR ANTIOXIDANT ACTIVITY. African journal of traditional, complementary, and alternative medicines : AJTCAM. 2017; 14(2):130-141. doi: 10.21010/ajtcam.v14i2.14. [PMID: 28573229]
Bo Zhang, Tiegui Nan, Zhilai Zhan, Liping Kang, Jian Yang, Yuan Yuan, Baomin Wang, Luqi Huang. Development of a monoclonal antibody-based enzyme-linked immunosorbent assay for luteoloside detection in Flos Lonicerae Japonicae. Analytical and bioanalytical chemistry. 2016 Sep; 408(22):6053-61. doi: 10.1007/s00216-016-9396-0. [PMID: 26892641]
Ayako Kure, Kiyotaka Nakagawa, Momoko Kondo, Shunji Kato, Fumiko Kimura, Akio Watanabe, Naoki Shoji, Sakiko Hatanaka, Tojiro Tsushida, Teruo Miyazawa. Metabolic Fate of Luteolin in Rats: Its Relationship to Anti-inflammatory Effect. Journal of agricultural and food chemistry. 2016 Jun; 64(21):4246-54. doi: 10.1021/acs.jafc.6b00964. [PMID: 27170112]
Carla Pereira, Lillian Barros, Ana Maria Carvalho, Celestino Santos-Buelga, Isabel C F R Ferreira. Infusions of artichoke and milk thistle represent a good source of phenolic acids and flavonoids. Food & function. 2015 Jan; 6(1):56-62. doi: 10.1039/c4fo00834k. [PMID: 25367590]
Sinikka Rahte, Richard Evans, Philippe J Eugster, Laurence Marcourt, Jean-Luc Wolfender, Andreas Kortenkamp, Deniz Tasdemir. Salvia officinalis for hot flushes: towards determination of mechanism of activity and active principles. Planta medica. 2013 Jun; 79(9):753-60. doi: 10.1055/s-0032-1328552. [PMID: 23670626]
Ran Yin, Fei Han, Zheng Tang, Ran Liu, Xu Zhao, Xiaohui Chen, Kaishun Bi. UFLC-MS/MS method for simultaneous determination of luteolin-7-O-gentiobioside, luteolin-7-O-β-D-glucoside and luteolin-7-O-β-D-glucuronide in beagle dog plasma and its application to a pharmacokinetic study after administration of traditional Chinese medicinal preparation: Kudiezi injection. Journal of pharmaceutical and biomedical analysis. 2013 Jan; 72(?):127-33. doi: 10.1016/j.jpba.2012.09.028. [PMID: 23146236]
Jun Zhao, Fang Xu, Jin-Hua He, Wei Tan, Zheng-Yi Gu, Long Ma. [Study on chemical constituents of Hyssopus cuspidatus]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Jan; 36(1):54-7. doi: . [PMID: 23750409]
Hong-Li Liu, Bai-Lian Liu, Guo-Cai Wang, Yi Dai, Wen-Cai Ye, Yao-Lan Li. [Studies on the chemical constituents from Conyza canadensis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 May; 34(5):718-20. doi: . [PMID: 21954558]
Kyoung-Sook Kim, Yeon-Joo Kwak, Kyung-Mi Kim, Hai Yang Yu, Byoung-Won Kang, Eunsook Chung, Young-Choon Lee, Jung-In Kim, Jai-Heon Lee. Purification and structure determination of gelatinase and collagenase inhibitors from Viola patrinii fermentation extracts. Immunopharmacology and immunotoxicology. 2010 Dec; 32(4):614-6. doi: 10.3109/08923971003645631. [PMID: 20196628]
Seval Capanlar, Nazli Böke, Ihsan Yaşa, Süheyla Kirmizigül. A novel glycoside from Acanthus hirsutus (Acanthaceae). Natural product communications. 2010 Apr; 5(4):563-6. doi: ". [PMID: 20433073]
B Benedek, N Geisz, W Jäger, T Thalhammer, B Kopp. Choleretic effects of yarrow (Achillea millefolium s.l.) in the isolated perfused rat liver. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006 Nov; 13(9-10):702-6. doi: 10.1016/j.phymed.2005.10.005. [PMID: 16303291]
Shoko Kobayashi, Jun Watanabe, Eri Fukushi, Jun Kawabata, Mitsutoshi Nakajima, Michiko Watanabe. Polyphenols from some foodstuffs as inhibitors of ovalbumin permeation through caco-2 cell monolayers. Bioscience, biotechnology, and biochemistry. 2003 Jun; 67(6):1250-7. doi: 10.1271/bbb.67.1250. [PMID: 12843650]
Supinya Tewtrakul, Hirotsugu Miyashiro, Norio Nakamura, Masao Hattori, Takuya Kawahata, Toru Otake, Tomokazu Yoshinaga, Tamio Fujiwara, Tanomjit Supavita, Supreeya Yuenyongsawad, Pranee Rattanasuwon, Sukanya Dej-Adisai. HIV-1 integrase inhibitory substances from Coleus parvifolius. Phytotherapy research : PTR. 2003 Mar; 17(3):232-9. doi: 10.1002/ptr.1111. [PMID: 12672152]
Liselotte Krenn, Anca Miron, Enne Pemp, Ursula Petr, Brigitte Kopp. Flavonoids from Achillea nobilis L. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2003 Jan; 58(1-2):11-6. doi: 10.1515/znc-2003-1-202. [PMID: 12622219]
Ming Hong Lee, Yeon Kyoung Son, Yong Nam Han. Tissue factor inhibitory flavonoids from the fruits of Chaenomeles sinensis. Archives of pharmacal research. 2002 Dec; 25(6):842-50. doi: 10.1007/bf02977002. [PMID: 12510836]
Luis Góngora, Salvador Máñez, Rosa M Giner, M Carmen Recio, Alexander I Gray, José Luis Ríos. Phenolic glycosides from Phagnalon rupestre. Phytochemistry. 2002 Apr; 59(8):857-60. doi: 10.1016/s0031-9422(02)00011-0. [PMID: 11937166]
Gerd Vanhoenacker, Philippe Van Rompaey, Denis De Keukeleire, Pat Sandra. Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.). Natural product letters. 2002 Feb; 16(1):57-63. doi: 10.1080/1057563029001/4863. [PMID: 11942684]
H G Gumbinger, H Winterhoff, R Wylde, A Sosa. On the influence of the sugar moiety on the antigonadotropic activity of luteoline glycosides. Planta medica. 1992 Feb; 58(1):49-50. doi: 10.1055/s-2006-961388. [PMID: 1620743]