Lirioresinol A (BioDeep_00000017525)

Secondary id: BioDeep_00000002747, BioDeep_00000395621

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

4-[6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxy-phenol

化学式: C22H26O8 (418.1628)
中文名称: (+)-丁香树脂酚, DL-丁香树脂酚, 丁香脂素
谱图信息: 最多检出来源 Escherichia coli(natural_products) 86.21%

分子结构信息

SMILES: COC1=CC(=CC(=C1O)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)O)OC
InChI: InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3

描述信息

Syringaresinol is a lignan that is 7,9:7,9-diepoxylignane substituted by hydroxy groups at positions 4 and 4 and methoxy groups at positions 3, 3, 5 and 5 respectively. It has a role as a plant metabolite. It is a lignan, a polyphenol, an aromatic ether, a furofuran and a polyether.
Syringaresinol is a natural product found in Dracaena draco, Ficus septica, and other organisms with data available.
A lignan that is 7,9:7,9-diepoxylignane substituted by hydroxy groups at positions 4 and 4 and methoxy groups at positions 3, 3, 5 and 5 respectively.
Isolated from Artemisia absinthium (wormwood). Lirioresinol A is found in alcoholic beverages and herbs and spices.
Lirioresinol A is found in alcoholic beverages. Lirioresinol A is isolated from Artemisia absinthium (wormwood).

同义名列表

23 个代谢物同义名

4-[6-(4-hydroxy-3,5-dimethoxy-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxy-phenol; 4-[6-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenol; Phenol,4,4-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2,6-dimethoxy-,(1R,3aS,4R,6aS)-rel-; 4-[4-(4-hydroxy-3,5-dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenol; Phenol,4,4-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2,6-dimethoxy-; 4,4-(Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis(2,6-dimethoxyphenol); 4,4-tetrahydro-1h,3h-furo[3,4-c]furan-1,4-diylbis(2,6-dimethoxyphenol); syringaresinol, (1alpha,3aalpha, 4alpha,6aalpha)-(+-)-isomer; syringaresinol, (1R-(1alpha, 3aalpha,4alpha,6aalpha))-isomer; 3,3,5,5-tetramethoxy-7,9:7,9-diepoxylignane-4,4-diol; 3,3,5,5-tetramethoxy-7,9,7,9-diepoxylignan-4,4-diol; (-)-Lirioresinol B;DL-Syringaresinol; (+)-Episyringaresinol; (+/-)-Syringaresinol;; (+)-Syringaresinol; DL-Syringaresinol; Symplicosigenol; Syringylresinol; syringa-resinol; syringaresinol; Lirioresinol A; S(8-8)S; (+)-Syringaresinol

数据库引用编号

26 个数据库交叉引用编号

ChEBI: CHEBI:49211
ChEBI: CHEBI:47
KEGG: C10889
PubChem: 100067
HMDB: HMDB0038928
ChEMBL: CHEMBL4469429
Wikipedia: Syringaresinol
MeSH: syringaresinol
KNApSAcK: C00053808
KNApSAcK: C00000625
KNApSAcK: C00044152
KNApSAcK: C00002631
foodb: FDB018395
chemspider: 90423
CAS: 21453-71-4
CAS: 1177-14-6
CAS: 487-35-4
CAS: 21453-69-0
medchemexpress: HY-N8307
medchemexpress: HY-N1190
PMhub: MS000004716
MetaboLights: MTBLC49211
PubChem: 13072
3DMET: B04193
NIKKAJI: J15.958A
KNApSAcK: 47

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)

88 个相关的物种来源信息

115911 - Achatinella: 10.1016/J.PHYTOCHEM.2006.03.005
3625 - Actinidia chinensis: 10.1021/JF051488W
4615 - Ananas comosus: 10.1021/JF051488W
49314 - Annona cherimola: 10.1021/NP9800046
2029787 - Annona emarginata: 10.1021/NP9800046
49857 - Annona montana: 10.1021/NP9800046
306945 - Annona senegalensis: 10.1021/NP9800046
3702 - Arabidopsis thaliana: 10.3390/IJMS17091565
432629 - Arcangelisia gusanlung: 10.1021/NP100900K
225832 - Artabotrys: 10.1248/CPB.55.1597
2750749 - Artemisia alpina:
262982 - Artemisia apiacea:
496566 - Artemisia carvifolia:
1227620 - Artemisia caucasica:
1227633 - Artemisia minor: 10.1055/S-2006-959408
223869 - Artemisia pedemontana:
528300 - Asclepias subulata: 10.1248/CPB.56.1159
4686 - Asparagus officinalis: 10.1021/JF051488W
2664285 - Aspidosperma excelsum: 10.1016/S0031-9422(00)82898-8
597276 - Aspidosperma marcgravianum: 10.1016/S0031-9422(00)82898-8
4498 - Avena sativa: 10.1021/JF051488W
280850 - Bambusa emeiensis: 10.1021/NP200117Y
210348 - Brucea javanica: 10.1021/JF0709808
1609857 - Casearia membranacea: 10.1055/S-2003-41120
121072 - Cassytha: 10.1021/NP970348G
146995 - Chrysanthemum indicum: 10.4268/CJCMM20100613
1132458 - Cinnamomum kotoense: 10.1021/NP900225P
258907 - Cinnamomum osmophloeum: 10.1055/S-0029-1240634
1222053 - Cinnamomum reticulatum: 10.1080/14786411003746476
977953 - Cinnamomum subavenium: 10.1021/NP900225P
86864 - Codonopsis pilosula: 10.1055/S-2006-959552
3659 - Cucumis sativus: 10.1021/JF051488W
136205 - Curcuma aeruginosa: 10.1021/NP300694A
885948 - Daphne tangutica: 10.1016/J.FITOTE.2009.07.002
257357 - Dendrobium longicornu: 10.1055/S-2008-1074492
94219 - Dendrobium nobile: 10.1021/NP070423F
1009467 - Diospyros eriantha: 10.1055/S-2006-959539
344434 - Drypetes littoralis: 10.1021/NP0005964
82096 - Eleutherococcus senticosus: 10.1080/14786419.2010.485304
105886 - Eleutherococcus sessiliflorus: 10.1016/J.BMCL.2014.11.045
115466 - Euterpe oleracea: 10.1021/JF801792N
3617 - Fagopyrum esculentum: 10.1021/JF051488W
100573 - Ficus septica: 10.1002/JCCS.200200019
3746 - Fragaria: 10.1016/J.FOODCHEM.2012.03.133
29849 - Gaeumannomyces: 10.1021/NP010037C
316718 - Garcia: 10.1021/NP100440P
3380 - Gnetum: 10.1016/S0031-9422(02)00670-2
4232 - Helianthus annuus: 10.1021/JF048945D
229543 - Hibiscus cannabinus: 10.1248/CPB.53.56
106335 - Hibiscus syriacus: 10.1248/CPB.53.56
9606 - Homo sapiens: -
4513 - Hordeum vulgare: 10.1021/JF051488W
215659 - Hornstedtia reticulata: 10.1080/14786411003746476
466205 - Juniperus scopulorum: 10.1055/S-2006-959460
4006 - Linum usitatissimum: 10.1021/JF051488W
126736 - Litsea coreana: 10.1021/NP010236W
453235 - Litsea hypophaea: 10.1021/NP100022S
128685 - Machilus thunbergii: 10.1021/NP2001896
337466 - Machilus zuihoensis: 10.1021/NP2001896
344115 - Neolitsea pulchella: 10.1021/NP010236W
217471 - Neopallasia pectinata:
1439913 - Papaver canescens: 10.1055/S-2006-959484
586100 - Phyllanthus oligospermus: 10.1021/NP010059Z
296033 - Phyllanthus virgatus: 10.1021/NP010059Z
538264 - Piper eucalyptifolium:
1008928 - Pittosporum illicioides: 10.1021/NP8004503
22663 - Punica granatum: 10.3390/MOLECULES22101606
240228 - Raphanus sativus var. sativus: 10.1021/JF051488W
78511 - Ribes nigrum: 10.1016/J.FOODCHEM.2012.03.133
57936 - Rubus chamaemorus: 10.1016/J.FOODCHEM.2012.03.133
2293688 - Sarcopyramis nepalensis: 10.1080/10286020.2010.547682
324593 - Saussurea costus: 10.1248/CPB.53.1416
243817 - Saussurea pulchella: 10.1248/CPB.53.1416
4550 - Secale cereale: 10.1021/JF051488W
3246 - Selaginella: 10.1055/S-2006-959443
4081 - Solanum lycopersicum: 10.1021/JF051488W
4111 - Solanum melongena: 10.1021/JF051488W
34270 - Syringa vulgaris:
183267 - Talipariti tiliaceum: 10.1248/CPB.53.56
58440 - Tarenna: 10.1021/NP0603931
289660 - Trigonostemon: 10.1248/CPB.53.1321
4565 - Triticum aestivum: 10.1021/JF051488W
180763 - Vaccinium myrtillus: 10.1016/J.FOODCHEM.2012.03.133
180772 - Vaccinium vitis-idaea: 10.1016/J.FOODCHEM.2012.03.133
2717252 - Viburnum foetidum var. foetidum: 10.1248/CPB.57.1129
999598 - Vismia guianensis: 10.1016/S0031-9422(00)80095-3
29760 - Vitis vinifera: 10.1016/S0308-8146(03)00222-X
354527 - Zanthoxylum avicennae: 10.1021/NP070594K

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。

亚细胞结构定位		关联基因列表

文献列表

Zak Towle, Faye Cruickshank, C Logan Mackay, David J Clarke, Louise E Horsfall. Utilising Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) to track the oxidation of lignin by an alkaliphilic laccase. The Analyst. 2024 Apr; 149(8):2399-2411. doi: 10.1039/d4an00124a. [PMID: 38477231]
Yunhe Liu, Junzhe Wu, Luying Tan, Zhuoqiao Li, Peng Gao, Shanmei He, Qianyun Wang, Daohao Tang, Cuizhu Wang, Fang Wang, Pingya Li, Jinping Liu. (-)-Syringaresinol attenuates ulcerative colitis by improving intestinal epithelial barrier function and inhibiting inflammatory responses. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2024 Feb; 124(?):155292. doi: 10.1016/j.phymed.2023.155292. [PMID: 38190784]
Xian-Mei Piao, Ming-Feng Feng, Wei-Ping Zhao, Zhi-Hang Wu, Wen-Wen Zhang, Hui-Min Hou, Jin-Hui Wang, Li-Bo Wang, Jian Huang, Yan Zhang. Dendrocandin U from Dendrobium officinale Kimura et Migo Inhibits M1 Polarization in Alveolar Macrophage by Suppressing NF-κB Signaling Pathway. Chemistry & biodiversity. 2023 Nov; ?(?):e202300999. doi: 10.1002/cbdv.202300999. [PMID: 37933979]
Sijia Zhang, Lei Yang, Dongsheng Hu, Siqi He, Lingzhi Cui, Jiuling Zhao, Yuzhen Zhuo, Lanqiu Zhang, Ximo Wang. Syringaresinol alleviates IgG immune complex induced acute lung injury via activating PPARγ and suppressing pyroptosis. International immunopharmacology. 2023 Nov; 124(Pt B):111071. doi: 10.1016/j.intimp.2023.111071. [PMID: 37857123]
Lin Zhang, Jinyan Li, Li Hu, Yawen Wang, Zhanghua Wu, Yuanjun Meng, Zhiyun Liang, Li'e Yang, Gang Wei, Yuechun Huang. Identification of lignans and quality assessment in Dendrobium officinale under different cultivation modes. Rapid communications in mass spectrometry : RCM. 2023 Aug; 37(16):e9541. doi: 10.1002/rcm.9541. [PMID: 37190851]
Jianjie Wang, Jianqin Zou, Cheng Zhao, Han Yu, Jiajia Teng, Lei Dong. Syringaresinol inhibits cardiorenal fibrosis through HSP90 in a cardiorenal syndrome type 2. Human & experimental toxicology. 2023 Jan; 42(?):9603271231165678. doi: 10.1177/09603271231165678. [PMID: 36960691]
Yuzhen Zhuo, Lei Yang, Dihua Li, Lanqiu Zhang, Qi Zhang, Shukun Zhang, Caixia Li, Lihua Cui, Jian Hao, Jiarui Li, Ximo Wang. Syringaresinol Resisted Sepsis-Induced Acute Lung Injury by Suppressing Pyroptosis Via the Oestrogen Receptor-β Signalling Pathway. Inflammation. 2022 Apr; 45(2):824-837. doi: 10.1007/s10753-021-01587-9. [PMID: 34807349]
Lanqiu Zhang, Xiaolin Jiang, Jinlu Zhang, Hejun Gao, Lei Yang, Dihua Li, Qi Zhang, Botao Wang, Lihua Cui, Ximo Wang. (-)-Syringaresinol suppressed LPS-induced microglia activation via downregulation of NF-κB p65 signaling and interaction with ERβ. International immunopharmacology. 2021 Oct; 99(?):107986. doi: 10.1016/j.intimp.2021.107986. [PMID: 34303280]
Jin-Qiang Li, Chao-Jiang Xiao, Ye-Meng Li, Xin-Yan Tian, Xiang Dong, Bei Jiang. Astrernestin, a novel aurone-phenylpropanoid adduct from the roots of Astragalus ernestii. Natural product research. 2020 Oct; 34(20):2894-2899. doi: 10.1080/14786419.2019.1596101. [PMID: 30990071]
Guangru Li, Lei Yang, Lifeng Feng, Jiu Yang, Yafei Li, Jiale An, Dihua Li, Yang Xu, Yang Gao, Jing Li, Jie Liu, Liang Yang, Zhi Qi. Syringaresinol Protects against Type 1 Diabetic Cardiomyopathy by Alleviating Inflammation Responses, Cardiac Fibrosis, and Oxidative Stress. Molecular nutrition & food research. 2020 09; 64(18):e2000231. doi: 10.1002/mnfr.202000231. [PMID: 32729956]
Yifei Ma, Yongrui Bao, Wenjie Zhang, Xixiang Ying, Didier Stien. Four lignans from Portulaca oleracea L. and its antioxidant activities. Natural product research. 2020 Aug; 34(16):2276-2282. doi: 10.1080/14786419.2018.1534852. [PMID: 30580585]
Zsuzsanna Hajdú, Peter Forgo, Gergely Király, Gyula Pinke, István Zupkó, Judit Hohmann. Isolation of chemical constituents from Filago vulgaris and antiproliferative activity of the plant extract and its flavonoid against human tumor cell lines. Pakistan journal of pharmaceutical sciences. 2020 Jul; 33(4):1593-1597. doi: . [PMID: 33583792]
Navneet Kishore, Pradeep Kumar, Karuna Shanker, Akhilesh Kumar Verma. Human disorders associated with inflammation and the evolving role of natural products to overcome. European journal of medicinal chemistry. 2019 Oct; 179(?):272-309. doi: 10.1016/j.ejmech.2019.06.034. [PMID: 31255927]
Young Seon Cho, Woo Seok Song, Sang Ho Yoon, Kyeong-Yeol Park, Myoung-Hwan Kim. Syringaresinol suppresses excitatory synaptic transmission and picrotoxin-induced epileptic activity in the hippocampus through presynaptic mechanisms. Neuropharmacology. 2018 03; 131(?):68-82. doi: 10.1016/j.neuropharm.2017.12.014. [PMID: 29225041]
Ying-Ying Song, Ying Liu, Yong-Ming Yan, Xi-Feng Lu, Yong-Xian Cheng. Phenolic Compounds from Belamcanda chinensis Seeds. Molecules (Basel, Switzerland). 2018 Mar; 23(3):. doi: 10.3390/molecules23030580. [PMID: 29510567]
Huan-Huan Zhao, Jiang-Tao He, Zhen-Xiu Liu, Ji-Guang Huang. Cytotoxicity of chemical constituents from Torricellia tiliifolia DC. on Spodoptera litura (SL-1) cells. Pesticide biochemistry and physiology. 2018 Jan; 144(?):19-26. doi: 10.1016/j.pestbp.2017.10.008. [PMID: 29463404]
Eun Jin Mo, Jong Hoon Ahn, Yang Hee Jo, Seon Beom Kim, Bang Yeon Hwang, Mi Kyeong Lee. Inositol Derivatives and Phenolic Compounds from the Roots of Taraxacum coreanum. Molecules (Basel, Switzerland). 2017 Aug; 22(8):. doi: 10.3390/molecules22081349. [PMID: 28805750]
Si-Young Cho, Juewon Kim, Ji Hae Lee, Ji Hyun Sim, Dong-Hyun Cho, Il-Hong Bae, Hyunbok Lee, Min A Seol, Hyun Mu Shin, Tae-Joo Kim, Dae-Yong Kim, Su-Hyung Lee, Song Seok Shin, Sin-Hyeog Im, Hang-Rae Kim. Modulation of gut microbiota and delayed immunosenescence as a result of syringaresinol consumption in middle-aged mice. Scientific reports. 2016 12; 6(?):39026. doi: 10.1038/srep39026. [PMID: 27976725]
Yan-xi Chang, Bao-quan Bao, Xuan Zhang, J I Rimubatu, Ping Zhang. [Chemical Constituents from A Taditional Mongolian Medicine Clematis aethusifolia]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Jul; 39(7):1545-9. doi: . [PMID: 30203953]
Yue-ping Jiang, Yu-feng Liu, Qing-lan Guo, Cheng-bo Xu, Sheng Lin, Cheng-gen Zhu, Yong-chun Yang, Jian-gong Shi. [Lignanoids from an aqueous extract of the roots of Codonopsis pilosula]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 04; 51(4):616-25. doi: . [PMID: 29860746]
Jiang-li Yu, Gen-hua Zhu, Fang Liang, Min Liu, Xing Liu, Feng-qin Li, Hui-lian Huang. [Phenylpropanoid Constituents of Smilax trinervula]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Apr; 39(4):782-5. doi: . [PMID: 30132319]
Qin-ling Zhang, Xiao-chun Bai, Xiao-lan Cao, Yun Yun. [Chemical Constituents from Drypetes hainanensis Stems and Leaves]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Oct; 38(10):2095-7. doi: . [PMID: 27254922]
Jing Sun, Hui-Xia Huo, Zheng Huang, Jing Zhang, Jun Li, Peng-Fei Tu. A new γ-alkylated-γ-butyrolactone from the roots of Solanum melongena. Chinese journal of natural medicines. 2015 Sep; 13(9):699-703. doi: 10.1016/s1875-5364(15)30068-6. [PMID: 26412430]
Wen-fang Yi, Jia-bing Peng, Gang Ren, Wei Jiang, Jian Liang, Wen-jun Yuan. [Chemical Constitutes from Root of Artocarpus styracifolius]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 May; 38(5):972-4. doi: . [PMID: 26767289]
Qiang Wei, Zhen Qiu, Fei Xu, Qian-rong Li, Hao Yin. [Chemical Components from Leaves of Fatsia japonica and Their Antitumor Activities in vitro]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Apr; 38(4):745-50. doi: . [PMID: 26672339]
Hyun Woo Park, Si Young Cho, Hyun Hee Kim, Bong Sik Yun, Jeong Un Kim, Sang Jun Lee, Jiyong Park. Enantioselective induction of SIRT1 gene by syringaresinol from Panax ginseng berry and Acanthopanax senticosus Harms stem. Bioorganic & medicinal chemistry letters. 2015 Jan; 25(2):307-9. doi: 10.1016/j.bmcl.2014.11.045. [PMID: 25479772]
Chun-Ling Zhu, Jian-Xiong Ma. [Chemical constituents of Mallotus paniculatus]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Aug; 37(8):1385-7. doi: ". [PMID: 25726646]
Hui Chen, Zhi-You Hao, Xiao-Lan Wang, Xiao-Ke Zheng, Wei-Sheng Feng, Yan-Zhi Wang. Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis. Chinese journal of natural medicines. 2014 Feb; 12(2):148-50. doi: 10.1016/s1875-5364(14)60024-8. [PMID: 24636067]
Manh Heun Kim, Jun Hye Jang, Myeong Hwan Oh, Jun Hyeok Heo, Min Won Lee. The comparison of DPPH-scavenging capacity and anti-inflammatory effects of phenolic compounds isolated from the stems of Stewartia koreana Nakai. Natural product research. 2014; 28(17):1409-12. doi: 10.1080/14786419.2014.905560. [PMID: 24749670]
Laila Meija, Paivi Söderholm, Adile Samaletdin, Gita Ignace, Inese Siksna, Rafaels Joffe, Aivars Lejnieks, Vilnis Lietuvietis, Indrikis Krams, Herman Adlercreutz. Dietary intake and major sources of plant lignans in Latvian men and women. International journal of food sciences and nutrition. 2013 Aug; 64(5):535-43. doi: 10.3109/09637486.2013.765835. [PMID: 23373826]
Tian-Min Wang, Ru-Feng Wang, Hu-Biao Chen, Ming-Ying Shang, Shao-Qing Cai. Alkyl and phenolic glycosides from Saussurea stella. Fitoterapia. 2013 Jul; 88(?):38-43. doi: 10.1016/j.fitote.2013.03.027. [PMID: 23567860]
Hugues Fouotsa, Armelle T Mbaveng, Celine D Mbazoa, Augustin E Nkengfack, Shaheen Farzana, Choudhary M Iqbal, Jacobus J Marion Meyer, Namrita Lall, Victor Kuete. Antibacterial constituents of three Cameroonian medicinal plants: Garcinia nobilis, Oricia suaveolens and Balsamocitrus camerunensis. BMC complementary and alternative medicine. 2013 Apr; 13(?):81. doi: 10.1186/1472-6882-13-81. [PMID: 23574627]
Alexia Agiomyrgianaki, Panos V Petrakis, Photis Dais. Influence of harvest year, cultivar and geographical origin on Greek extra virgin olive oils composition: a study by NMR spectroscopy and biometric analysis. Food chemistry. 2012 Dec; 135(4):2561-8. doi: 10.1016/j.foodchem.2012.07.050. [PMID: 22980843]
Pepijn Prinsen, Ana Gutiérrez, José C del Río. Lipophilic extractives from the cortex and pith of elephant grass ( Pennisetum purpureum Schumach.) stems. Journal of agricultural and food chemistry. 2012 Jun; 60(25):6408-17. doi: 10.1021/jf301753w. [PMID: 22646817]
Xiao-Feng Shi, Zhao-Hui Bai, Dong-Yan Liu, Shuang Li. [Study on the chemical constituent from the dichloromethane extract. of the pine needles of Cedrus deodara]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Mar; 35(3):404-6. doi: . [PMID: 22876679]
Liya Li, Navindra P Seeram. Further investigation into maple syrup yields 3 new lignans, a new phenylpropanoid, and 26 other phytochemicals. Journal of agricultural and food chemistry. 2011 Jul; 59(14):7708-16. doi: 10.1021/jf2011613. [PMID: 21675726]
Ting Zhang, Yan Yang, Guanhua Du, Ruoyun Chen. [Study on chemical constituents from the roots of Saussurea lappa]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jun; 36(12):1620-2. doi: ". [PMID: 22007546]
Huan-Kai Yao, Jing-Yu Duan, Yan Li, Jian-Hui Wang, Xiao-Xing Yin, Hong-Quan Duan. [Studies on the chemical constituents from the roots of Kalopanax septemlobus]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2011 May; 34(5):716-8. doi: . [PMID: 21954557]
Jin-Wen Zhang, Mei Liao, Hua-Dong Chen, Yong-Hui Zhang. Structural elucidation of a new flavone from Sarcopyramis nepalensis. Journal of Asian natural products research. 2011 Mar; 13(3):256-9. doi: 10.1080/10286020.2010.547682. [PMID: 21409688]
Jorge Rencoret, Ana Gutiérrez, Lidia Nieto, J Jiménez-Barbero, Craig B Faulds, Hoon Kim, John Ralph, Angel T Martínez, José C Del Río. Lignin composition and structure in young versus adult Eucalyptus globulus plants. Plant physiology. 2011 Feb; 155(2):667-82. doi: 10.1104/pp.110.167254. [PMID: 21098672]
A R Gohari, S Saeidnia, M Bayati-Moghadam, Gh Amin. Lignans and neolignans from Stelleropsis antoninae. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2011; 19(1):74-9. doi: . [PMID: 22615643]
Herman Adlercreutz. Can rye intake decrease risk of human breast cancer?. Food & nutrition research. 2010 Nov; 54(?):. doi: 10.3402/fnr.v54i0.5231. [PMID: 21311613]
Yanling Zhang, Maoluo Gan, Shuai Li, Sujuan Wang, Chenggen Zhu, Yongchun Yang, Jinfeng Hu, Naihong Chen, Jiangong Shi. [Chemical constituents of stems and branches of Adina polycephala]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 May; 35(10):1261-71. doi: 10.4268/cjcmm20101010. [PMID: 20707194]
Ying Zhao, Fei Liu, Hong-Xiang Lou. [Studies on the chemical constituents of Solanum nigrum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2010 Apr; 33(4):555-6. doi: ". [PMID: 20845784]
Chao Wang, Liping Zhu, Jingzhi Yang, Chuangjun Li, Dongming Zhang. [Chemical constituents from Sarcandra glabra]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Mar; 35(6):714-7. doi: 10.4268/cjcmm20100612. [PMID: 20545194]
Niina M Saarinen, Juhani Tuominen, Liisa Pylkkänen, Risto Santti. Assessment of information to substantiate a health claim on the prevention of prostate cancer by lignans. Nutrients. 2010 02; 2(2):99-115. doi: 10.3390/nu2020099. [PMID: 22254011]
Prathan Luecha, Kaoru Umehara, Toshio Miyase, Hiroshi Noguchi. Antiestrogenic constituents of the Thai medicinal plants Capparis flavicans and Vitex glabrata. Journal of natural products. 2009 Nov; 72(11):1954-9. doi: 10.1021/np9006298. [PMID: 19943620]
Chao Liu, Shao-Min Zhong, Ruo-Yun Chen, Yan Wu, Xue-Jun Zhu. Two new compounds from the dried tender stems of Cinnamomum cassia. Journal of Asian natural products research. 2009 Sep; 11(9):845-9. doi: 10.1080/10286020903185942. [PMID: 20183334]
Stella Christophoridou, Photis Dais. Detection and quantification of phenolic compounds in olive oil by high resolution 1H nuclear magnetic resonance spectroscopy. Analytica chimica acta. 2009 Feb; 633(2):283-92. doi: 10.1016/j.aca.2008.11.048. [PMID: 19166735]
Luis Enrique Cuca Suarez, Manuel Elkin Pattarroyo, Jose Manuel Lozano, Franco Delle Monache. Biological activity of secondary metabolites from Peltostigma guatemalense. Natural product research. 2009; 23(4):370-4. doi: 10.1080/14786410802228439. [PMID: 19296377]
Chien-Chang Shen, Ching-Li Ni, Yuh-Chiang Shen, Yu-Ling Huang, Ching-Hsia Kuo, Tian-Shung Wu, Chien-Chih Chen. Phenolic constituents from the stem bark of Magnolia officinalis. Journal of natural products. 2009 Jan; 72(1):168-71. doi: 10.1021/np800494e. [PMID: 19086868]
Li-hua Yan, Li-zhen Xu, Jia Lin, Zhong-mei Zou, Bao-hua Zhao, Shi-lin Yang. [Studies on lignan constituents of Clematis parviloba]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Aug; 33(15):1839-43. doi: . [PMID: 19007011]
Li Shao, Wei-hua Huang, Chao-feng Zhang, Lei Wang, Mian Zhang, Zheng-tao Wang. [Study on chemical constituents from stem of Dendrobium aphyllum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Jul; 33(14):1693-5. doi: ". [PMID: 18841768]
Ming-An Ouyang, Yung-Shung Wein, Zhen-Kun Zhang, Yueh-Hsiung Kuo. Inhibitory activity against tobacco mosaic virus (TMV) replication of pinoresinol and syringaresinol lignans and their glycosides from the root of Rhus javanica var. roxburghiana. Journal of agricultural and food chemistry. 2007 Aug; 55(16):6460-5. doi: 10.1021/jf0709808. [PMID: 17616139]
Annika I Smeds, Patrik C Eklund, Rainer E Sjöholm, Stefan M Willför, Sansei Nishibe, Takeshi Deyama, Bjarne R Holmbom. Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts. Journal of agricultural and food chemistry. 2007 Feb; 55(4):1337-46. doi: 10.1021/jf0629134. [PMID: 17261017]
Francesca Cutillo, Marina DellaGreca, Melania Gionti, Lucio Previtera, Armando Zarrelli. Phenols and lignans from Chenopodium album. Phytochemical analysis : PCA. 2006 Sep; 17(5):344-9. doi: 10.1002/pca.924. [PMID: 17019936]
Qiang Zhang, Long-Ru Sun. [Studies on chemical constituents of Serissa serissoides roots]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2006 Aug; 29(8):786-8. doi: ". [PMID: 17076236]
Johanna W Lampe, Charlotte Atkinson, Meredith A J Hullar. Assessing exposure to lignans and their metabolites in humans. Journal of AOAC International. 2006 Jul; 89(4):1174-81. doi: . [PMID: 16915861]
Yan-Qing Gong, Hong Yang, Yun Liu, Ai-Qun Liang, Zheng-Tao Wang, Luo-Shan Xu, Zhi-Bi Hu. [Studies on chemical constituents in stem of Dendrobium chrysotoxum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Feb; 31(4):304-6. doi: ". [PMID: 16706020]
Ji Ma, Shannon H Jones, Rebekah Marshall, Xihan Wu, Sidney M Hecht. DNA topoisomerase I inhibitors from Rinorea anguifera. Bioorganic & medicinal chemistry letters. 2005 Feb; 15(3):813-6. doi: 10.1016/j.bmcl.2004.10.095. [PMID: 15664863]
José L Peñalvo, Satu-M Heinonen, Tarja Nurmi, Takeshi Deyama, Sansey Nishibe, Herman Adlercreutz. Plant lignans in soy-based health supplements. Journal of agricultural and food chemistry. 2004 Jun; 52(13):4133-8. doi: 10.1021/jf0497509. [PMID: 15212459]
Shinya Sasaki, Tomoaki Nishida, Yuji Tsutsumi, Ryuichiro Kondo. Lignin dehydrogenative polymerization mechanism: a poplar cell wall peroxidase directly oxidizes polymer lignin and produces in vitro dehydrogenative polymer rich in beta-O-4 linkage. FEBS letters. 2004 Mar; 562(1-3):197-201. doi: 10.1016/s0014-5793(04)00224-8. [PMID: 15044025]
Hai-feng Gu, Ruo-yun Chen, Yu-hua Sun, Fa Liu. [Studies on chemical constituents from herb of Dracocephalum moldavica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Mar; 29(3):232-4. doi: ". [PMID: 15706847]
Tarja Nurmi, Sari Voutilainen, Kristiina Nyyssönen, Herman Adlercreutz, Jukka T Salonen. Liquid chromatography method for plant and mammalian lignans in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Dec; 798(1):101-10. doi: 10.1016/j.jchromb.2003.09.018. [PMID: 14630364]
Hyun-Ju Jung, Hee-Juhn Park, Ryung-Gue Kim, Kyoung-Min Shin, Joohun Ha, Jong-Won Choi, Hyoung Ja Kim, Yong Sup Lee, Kyung-Tae Lee. In vivo anti-inflammatory and antinociceptive effects of liriodendrin isolated from the stem bark of Acanthopanax senticosus. Planta medica. 2003 Jul; 69(7):610-6. doi: 10.1055/s-2003-41127. [PMID: 12898415]
A El-Hassan, M El-Sayed, A I Hamed, I K Rhee, A A Ahmed, K P Zeller, R Verpoorte. Bioactive constituents of Leptadenia arborea. Fitoterapia. 2003 Feb; 74(1-2):184-7. doi: 10.1016/s0367-326x(02)00314-3. [PMID: 12628421]
Ching-Chuan Kuo, Wenchang Chiang, Guey-Ping Liu, Ya-Lin Chien, Jang-Yang Chang, Ching-Kuo Lee, Jir-Mehng Lo, Shou-Ling Huang, Ming-Chih Shih, Yueh-Hsiung Kuo. 2,2'-Diphenyl-1-picrylhydrazyl radical-scavenging active components from adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) hulls. Journal of agricultural and food chemistry. 2002 Oct; 50(21):5850-5. doi: 10.1021/jf020391w. [PMID: 12358449]
Zhengbing Gu, Xinjian Chen, Genjin Yang, Tingzhao Li, Wenyong Liu, Weidong Zhang. [Studies on immunocompetent constituents of Patrinia scabra Bunge]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2002 Mar; 25(3):178-80. doi: ". [PMID: 12583160]
T Deyama, S Nishibe, Y Nakazawa. Constituents and pharmacological effects of Eucommia and Siberian ginseng. Acta pharmacologica Sinica. 2001 Dec; 22(12):1057-70. doi: ". [PMID: 11749801]
S Heinonen, T Nurmi, K Liukkonen, K Poutanen, K Wähälä, T Deyama, S Nishibe, H Adlercreutz. In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol. Journal of agricultural and food chemistry. 2001 Jul; 49(7):3178-86. doi: 10.1021/jf010038a. [PMID: 11453749]
S H Wu, X D Luo, Y B Ma, X J Hao, J Zhou, D G Wu. Two new germacranolides from Magnolia grandiflora. Journal of Asian natural products research. 2001; 3(2):95-102. doi: 10.1080/10286020108041376. [PMID: 11407820]
S J Lee, Y S Yun, I K Lee, I J Ryoo, B S Yun, I D Yoo. An antioxidant lignan and other constituents from the root bark of Hibiscus syriacus. Planta medica. 1999 Oct; 65(7):658-60. doi: 10.1055/s-2006-960841. [PMID: 10617409]
H Zhang, W Yan, Y Lu, Q Zheng. [Constituents of lignanoids in Siphonostegia chinensis Benth]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 1995 Apr; 20(4):230-1, 253. doi: ". [PMID: 7646792]
N Suh, L Luyengi, H H Fong, A D Kinghorn, J M Pezzuto. Discovery of natural product chemopreventive agents utilizing HL-60 cell differentiation as a model. Anticancer research. 1995 Mar; 15(2):233-9. doi: . [PMID: 7762989]
J X Guo, S S Handa, J M Pezzuto, A D Kinghorn, N R Farnsworth. Plant anticancer agents XXXIII. Constituents of Passerina vulgaris. Planta medica. 1984 Jun; 50(3):264-5. doi: ". [PMID: 6484032]