Lariciresinol (BioDeep_00000396578)

Main id: BioDeep_00000004010

 

PANOMIX_OTCML-2023


代谢物信息卡片


3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2R-(2alpha,3beta,4beta))-

化学式: C20H24O6 (360.1572804)
中文名称: 落叶松树脂醇, (+)-落叶松树脂醇
谱图信息: 最多检出来源 Viridiplantae(plant) 3.03%

分子结构信息

SMILES: COC1=C(C=CC(=C1)CC2COC(C2CO)C3=CC(=C(C=C3)O)OC)O
InChI: InChI=1S/C20H24O6/c1-24-18-8-12(3-5-16(18)22)7-14-11-26-20(15(14)10-21)13-4-6-17(23)19(9-13)25-2/h3-6,8-9,14-15,20-23H,7,10-11H2,1-2H3

描述信息

(+)-lariciresinol is a lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). It has a role as an antifungal agent and a plant metabolite. It is a member of oxolanes, a member of phenols, a lignan, a primary alcohol and an aromatic ether. It is an enantiomer of a (-)-lariciresinol.
Lariciresinol is a natural product found in Magnolia kachirachirai, Euterpe oleracea, and other organisms with data available.
See also: Acai fruit pulp (part of).
A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer).
(-)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as ostrich fern, pepper (c. frutescens), ohelo berry, and guava, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products.
Annotation level-1
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.823
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.820
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.818
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.812

同义名列表

33 个代谢物同义名

3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2R-(2alpha,3beta,4beta))-; (2S,3R,4R)-Tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-furanmethanol; (+)-Lariciresinol; 3-furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2S,3R,4R)-; 3-furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-, (2R,3S,4S)-; 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxy-phenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl]methyl]-2-methoxy-phenol; 3-Furanmethanol,tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-, (2S,3R,4R)-; (+)-4-[[(3S,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol; 4-[[(3R,4R,5S)-4-(hydroxymethyl)-5-(3-methoxy-4-oxidanyl-phenyl)oxolan-3-yl]methyl]-2-methoxy-phenol; 4-[(2S,3R,4R)-4-(4-Hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydro-2-furanyl]-2-methoxyphenol; 4-[(2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methoxyphenol; 4-((2S,3R,4R)-4-(4-hydroxy-3-methoxybenzyl)-3-(hydroxymethyl)tetrahydrofuran-2-yl)-2-methoxyphenol; 4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxymethyl)oxolan-3-yl]methyl]-2-methoxyphenol; tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-((4-hydroxy-3-methoxyphenyl)methyl)-3-furanmethanol; 3-Furanmethanol, tetrahydro-2-(4-hydroxy-3-methoxyphenyl)-4-vanillyl-; lariciresinol (2R-(2alpha,3beta,4beta))-isomer; (+)-Lariciresinol, >=95.0\\% (HPLC); MHXCIKYXNYCMHY-AUSJPIAWSA-N; Lariciresinol, (+)-; (+)-lariciresinol; (-)-lariciresinol; UNII-73XCE5OZB0; larici-resinol; Lariciresinol; 73XCE5OZB0; 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxy-phenyl)methyl]-3-(hydroxymethyl)tetrahydrofuran-2-yl]-2-methoxy-phenol; 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-tetrahydrofuranyl]-2-methoxyphenol; 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxy-phenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxy-phenol; 4-[(2S,3R,4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol; 4-[(2S,3R,4R)-4-(4-hydroxy-3-methoxy-benzyl)-3-methylol-tetrahydrofuran-2-yl]-2-methoxy-phenol; 27003-73-2; NSC329247; C10646; Arbo 4



数据库引用编号

46 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

116 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(113)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

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

  • Jingxian Feng, Yuan Yao, Yuqi Qiao, Xueqi Ma, Zongtai Wu, Yonghao Duan, Peng Di, Wansheng Chen, Ying Xiao. Effect of pinoresinol-lariciresinol reductases on biosynthesis of lignans with substrate selectivity in Schisandra chinensis. Phytochemistry. 2024 May; 221(?):114053. doi: 10.1016/j.phytochem.2024.114053. [PMID: 38479587]
  • Mona Soltani, Reza Fotovat, Mohsen Sharifi, Najmeh Ahmadian Chashmi, Mehrdad Behmanesh. In Vitro Comparative Study on Antineoplastic Effects of Pinoresinol and Lariciresinol on Healthy Cells and Breast Cancer-Derived Human Cells. Iranian journal of medical sciences. 2024 Jan; 49(1):30-39. doi: 10.30476/ijms.2023.94805.2611. [PMID: 38322161]
  • Sikiru Olaitan Balogun, Amilcar Sabino Damazo, Eduarda Pavan, Fabiana de Freitas Figueiredo, Karuppusamy Arunachalam, Leonardo M de Souza Mesquita, Wagner Vilegas, Domingos Tabajara de Oliveira Martins. Evidence for the Involvement of Cytokines Modulation and Prokinetic Properties in Gastric Ulcer Healing Effects of Helicteres sacarolha A. St.-Hil. A. Juss. Chemistry & biodiversity. 2022 Dec; 19(12):e202200322. doi: 10.1002/cbdv.202200322. [PMID: 36269048]
  • Joanda P R E Silva, Laiane C O Pereira, Lucas S Abreu, Francisca S V Lins, Thalisson A de Souza, Renan F do Espírito-Santo, Renata P C Barros, Cristiane F Villarreal, José I M de Melo, Marcus T Scotti, Vicente C de O Costa, Lucas H Martorano, Fernando M Dos Santos, Raimundo Braz Filho, Marcelo S da Silva, Josean F Tavares. Targeted Isolation of Anti-inflammatory Lignans from Justicia aequilabris by Molecular Networking Approach. Journal of natural products. 2022 09; 85(9):2184-2191. doi: 10.1021/acs.jnatprod.2c00478. [PMID: 35998343]
  • Lu Yang, Huiqiang Wang, Haiyan Yan, Kun Wang, Shuo Wu, Yuhuan Li. (-)-Lariciresinol Isolated from the Roots of Isatis indigotica Fortune ex Lindl. Inhibits Hepatitis B Virus by Regulating Viral Transcription. Molecules (Basel, Switzerland). 2022 May; 27(10):. doi: 10.3390/molecules27103223. [PMID: 35630700]
  • Jyoti Mehta, Rajan Rolta, Kamal Dev. Role of medicinal plants from North Western Himalayas as an efflux pump inhibitor against MDR AcrAB-TolC Salmonella enterica serovar typhimurium: In vitro and In silico studies. Journal of ethnopharmacology. 2022 Jan; 282(?):114589. doi: 10.1016/j.jep.2021.114589. [PMID: 34492321]
  • Bushra Asad, Taimoor Khan, Faiza Zareen Gul, Muhammad Asad Ullah, Samantha Drouet, Sara Mikac, Laurine Garros, Manon Ferrier, Shankhamala Bose, Thibaut Munsch, Duangjai Tungmunnithum, Arnaud Lanoue, Nathalie Giglioli-Guivarc'h, Christophe Hano, Bilal Haider Abbasi. Scarlet Flax Linum grandiflorum (L.) In Vitro Cultures as a New Source of Antioxidant and Anti-Inflammatory Lignans. Molecules (Basel, Switzerland). 2021 Jul; 26(15):. doi: 10.3390/molecules26154511. [PMID: 34361665]
  • InWha Park, Hee Sun Byun, Gang Min Hur, MinKyun Na. Tulipiferamide A, an Alkamide from Liriodendron tulipifera, Exhibits an Anti-Inflammatory Effect via Targeting IKKβ Phosphorylation. Journal of natural products. 2021 05; 84(5):1598-1606. doi: 10.1021/acs.jnatprod.1c00146. [PMID: 33939429]
  • Ying Xiao, Kai Shao, Jingwen Zhou, Lian Wang, Xueqi Ma, Di Wu, Yingbo Yang, Junfeng Chen, Jingxian Feng, Shi Qiu, Zongyou Lv, Lei Zhang, Peng Zhang, Wansheng Chen. Structure-based engineering of substrate specificity for pinoresinol-lariciresinol reductases. Nature communications. 2021 05; 12(1):2828. doi: 10.1038/s41467-021-23095-y. [PMID: 33990581]
  • Hui Zheng, Li Wang, Tao Yang, Dan Liu, Hong-Mei Li, Xuan-Qin Chen, Rong-Tao Li. New Terpenoids And Lignans From The Twigs Of Tripterygium Hypoglaucum. Natural product research. 2020 Jul; 34(13):1853-1861. doi: 10.1080/14786419.2018.1564297. [PMID: 30691300]
  • Yingling Wu, Dawei Xing, Guoliang Ma, Xinlong Dai, Liping Gao, Tao Xia. A variable loop involved in the substrate selectivity of pinoresinol/lariciresinol reductase from Camellia sinensis. Phytochemistry. 2019 Jun; 162(?):1-9. doi: 10.1016/j.phytochem.2019.02.003. [PMID: 30844490]
  • Lucija Markulin, Cyrielle Corbin, Sullivan Renouard, Samantha Drouet, Laurent Gutierrez, Ivan Mateljak, Daniel Auguin, Christophe Hano, Elisabeth Fuss, Eric Lainé. Pinoresinol-lariciresinol reductases, key to the lignan synthesis in plants. Planta. 2019 Jun; 249(6):1695-1714. doi: 10.1007/s00425-019-03137-y. [PMID: 30895445]
  • Luca Pompermaier, Elke H Heiss, Mostafa Alilou, Fabian Mayr, Mawunu Monizi, Thea Lautenschlaeger, Daniela Schuster, Stefan Schwaiger, Hermann Stuppner. Dihydrochalcone Glucosides from the Subaerial Parts of Thonningia sanguinea and Their in Vitro PTP1B Inhibitory Activities. Journal of natural products. 2018 09; 81(9):2091-2100. doi: 10.1021/acs.jnatprod.8b00450. [PMID: 30207720]
  • Yun-Seo Kil, Seong Min Kim, Unwoo Kang, Hae Young Chung, Eun Kyoung Seo. Peroxynitrite-Scavenging Glycosides from the Stem Bark of Catalpa ovata. Journal of natural products. 2017 08; 80(8):2240-2251. doi: 10.1021/acs.jnatprod.7b00139. [PMID: 28787158]
  • Beixian Zhou, Jing Li, Xiaoli Liang, Zifeng Yang, Zhihong Jiang. Transcriptome profiling of influenza A virus-infected lung epithelial (A549) cells with lariciresinol-4-β-D-glucopyranoside treatment. PloS one. 2017; 12(3):e0173058. doi: 10.1371/journal.pone.0173058. [PMID: 28273165]
  • Zhan-Jun Ma, Xue-Xi Wang, Gang Su, Jing-Jing Yang, Ya-Juan Zhu, You-Wei Wu, Jing Li, Li Lu, Long Zeng, Hai-Xia Pei. Proteomic analysis of apoptosis induction by lariciresinol in human HepG2 cells. Chemico-biological interactions. 2016 Aug; 256(?):209-19. doi: 10.1016/j.cbi.2016.07.011. [PMID: 27417256]
  • Won Se Suh, Lalita Subedi, Sun Yeou Kim, Sang Un Choi, Kang Ro Lee. Bioactive lignan constituents from the twigs of Sambucus williamsii. Bioorganic & medicinal chemistry letters. 2016 Apr; 26(8):1877-80. doi: 10.1016/j.bmcl.2016.03.023. [PMID: 26988298]
  • 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]
  • Nuoendagula, Naofumi Kamimura, Tetsuya Mori, Ryo Nakabayashi, Yukiko Tsuji, Shojiro Hishiyama, Kazuki Saito, Eiji Masai, Shinya Kajita. Expression and functional analyses of a putative phenylcoumaran benzylic ether reductase in Arabidopsis thaliana. Plant cell reports. 2016 Mar; 35(3):513-26. doi: 10.1007/s00299-015-1899-1. [PMID: 26601823]
  • Thao Quyen Cao, Manh Hung Tran, Jeong Ah Kim, Phuong Thao Tran, Jeong-Hyung Lee, Mi Hee Woo, Hyeong-Kyu Lee, Byung Sun Min. Inhibitory effects of compounds from Styrax obassia on NO production. Bioorganic & medicinal chemistry letters. 2015 Nov; 25(22):5087-91. doi: 10.1016/j.bmcl.2015.10.020. [PMID: 26483135]
  • Ying Xiao, Qian Ji, Shouhong Gao, Hexin Tan, Ruibing Chen, Qing Li, Junfeng Chen, Yingbo Yang, Lei Zhang, Zhengtao Wang, Wansheng Chen, Zhibi Hu. Combined transcriptome and metabolite profiling reveals that IiPLR1 plays an important role in lariciresinol accumulation in Isatis indigotica. Journal of experimental botany. 2015 Oct; 66(20):6259-71. doi: 10.1093/jxb/erv333. [PMID: 26163698]
  • Ya-mei Zhang, Pu-zhao Zhang. [Lignans from Stem Bark of Styrax perkinsiae]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1202-5. doi: ". [PMID: 26762060]
  • Sullivan Renouard, Marie-Aude Tribalatc, Frederic Lamblin, Gaëlle Mongelard, Ophélie Fliniaux, Cyrielle Corbin, Djurdjica Marosevic, Serge Pilard, Hervé Demailly, Laurent Gutierrez, Christophe Hano, François Mesnard, Eric Lainé. RNAi-mediated pinoresinol lariciresinol reductase gene silencing in flax (Linum usitatissimum L.) seed coat: consequences on lignans and neolignans accumulation. Journal of plant physiology. 2014 Sep; 171(15):1372-7. doi: 10.1016/j.jplph.2014.06.005. [PMID: 25046758]
  • Eliana Spilioti, Bjarne Holmbom, Athanasios G Papavassiliou, Paraskevi Moutsatsou. Lignans 7-hydroxymatairesinol and 7-hydroxymatairesinol 2 exhibit anti-inflammatory activity in human aortic endothelial cells. Molecular nutrition & food research. 2014 Apr; 58(4):749-59. doi: 10.1002/mnfr.201300318. [PMID: 24311533]
  • Oue-artorn Rajachan, Somdej Kanokmedhakul, Phitak Nasomjai, Kwanjai Kanokmedhakul. Chemical constituents and biological activities from roots of Enkleia siamensis. Natural product research. 2014; 28(4):268-70. doi: 10.1080/14786419.2013.838241. [PMID: 24047498]
  • Satoshi Yamauchi, Mitsuko Kumamoto, Yuki Ochi, Hisashi Nishiwaki, Yoshihiro Shuto. Structure-plant growth inhibitory activity relationship of lariciresinol. Journal of agricultural and food chemistry. 2013 Dec; 61(50):12297-306. doi: 10.1021/jf404292w. [PMID: 24274795]
  • 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]
  • Y Fukuhara, N Kamimura, M Nakajima, S Hishiyama, H Hara, D Kasai, Y Tsuji, S Narita-Yamada, S Nakamura, Y Katano, N Fujita, Y Katayama, M Fukuda, S Kajita, E Masai. Discovery of pinoresinol reductase genes in sphingomonads. Enzyme and microbial technology. 2013 Jan; 52(1):38-43. doi: 10.1016/j.enzmictec.2012.10.004. [PMID: 23199737]
  • Alexandrine During, Céline Debouche, Thomas Raas, Yvan Larondelle. Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells. The Journal of nutrition. 2012 Oct; 142(10):1798-805. doi: 10.3945/jn.112.162453. [PMID: 22955517]
  • Liang Chen, Lei Wang, Qingwen Zhang, Shengyuan Zhang, Wencai Ye. [Non-alkaloid chemical constituents from Coptis chinensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 May; 37(9):1241-4. doi: 10.4268/cjcmm20120915. [PMID: 22803368]
  • Sedigheh Esmaeilzadeh Bahabadi, Mozafar Sharifi, Mehrdad Behmanesh, Naser Safaie, Jun Murata, Ryoichi Araki, Tohru Yamagaki, Honoo Satake. Time-course changes in fungal elicitor-induced lignan synthesis and expression of the relevant genes in cell cultures of Linum album. Journal of plant physiology. 2012 Mar; 169(5):487-91. doi: 10.1016/j.jplph.2011.12.006. [PMID: 22218086]
  • Sullivan Renouard, Cyrielle Corbin, Tatiana Lopez, Josiane Montguillon, Laurent Gutierrez, Frédéric Lamblin, Eric Lainé, Christophe Hano. Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds. Planta. 2012 Jan; 235(1):85-98. doi: 10.1007/s00425-011-1492-y. [PMID: 21837520]
  • Hisashi Nishiwaki, Mitsuko Kumamoto, Yoshihiro Shuto, Satoshi Yamauchi. Stereoselective syntheses of all stereoisomers of lariciresinol and their plant growth inhibitory activities. Journal of agricultural and food chemistry. 2011 Dec; 59(24):13089-95. doi: 10.1021/jf203222w. [PMID: 22066904]
  • Bomi Hwang, Jaeyong Cho, In-sok Hwang, Hong-Guang Jin, Eun-Rhan Woo, Dong Gun Lee. Antifungal activity of lariciresinol derived from Sambucus williamsii and their membrane-active mechanisms in Candida albicans. Biochemical and biophysical research communications. 2011 Jul; 410(3):489-93. doi: 10.1016/j.bbrc.2011.06.004. [PMID: 21679690]
  • Qing-Huang Wang, Ke Peng, Le-He Tan, Hao-Fu Dai. Aquilarin A, a new benzenoid derivative from the fresh stem of Aquilaria sinensis. Molecules (Basel, Switzerland). 2010 Jun; 15(6):4011-6. doi: 10.3390/molecules15064011. [PMID: 20657422]
  • Souichi Nakashima, Hisashi Matsuda, Yoshimi Oda, Seikou Nakamura, Fengming Xu, Masayuki Yoshikawa. Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorganic & medicinal chemistry. 2010 Mar; 18(6):2337-2345. doi: 10.1016/j.bmc.2010.01.046. [PMID: 20189399]
  • N Pellegrini, S Valtueña, D Ardigò, F Brighenti, L Franzini, D Del Rio, F Scazzina, P M Piatti, I Zavaroni. Intake of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, and lariciresinol in relation to vascular inflammation and endothelial dysfunction in middle age-elderly men and post-menopausal women living in Northern Italy. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2010 Jan; 20(1):64-71. doi: 10.1016/j.numecd.2009.02.003. [PMID: 19361969]
  • Izabela Redzynia, Natasza E Ziółkowska, Wiesław R Majzner, Stefan Willför, Rainer Sjöholm, Patrik Eklund, Grzegorz D Bujacz. Structural investigation of biologically active phenolic compounds isolated from European tree species. Molecules (Basel, Switzerland). 2009 Oct; 14(10):4147-58. doi: 10.3390/molecules14104147. [PMID: 19924053]
  • Shun-ichi Wada, Yumiko Yasui, Harukuni Tokuda, Reiko Tanaka. Anti-tumor-initiating effects of phenolic compounds isolated from the bark of Picea jezoensis var. jezoensis. Bioorganic & medicinal chemistry. 2009 Sep; 17(17):6414-21. doi: 10.1016/j.bmc.2009.07.016. [PMID: 19646881]
  • Shuang Liang, Yun-Heng Shen, Jun-Mian Tian, Zhi-Jun Wu, Hui-Zi Jin, Wei-Dong Zhang, Shi-Kai Yan. Phenylpropanoids from Daphne feddei and their inhibitory activities against NO production. Journal of natural products. 2008 Nov; 71(11):1902-5. doi: 10.1021/np8004166. [PMID: 18986199]
  • Liu-Yi Tang, Ming-Hua Luo, Ning Jiang, Hong-Hui Lin. [Studies on chemical constituents of Sambucus adnata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 May; 30(5):549-51. doi: ". [PMID: 17727059]
  • Li Zuo, Jian-bei Li, Jing Xu, Jing-zhi Yang, Dong-ming Zhang, Yong-ling Tong. [Studies on chemical constituents in root of Isatis indigotica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 Apr; 32(8):688-91. doi: . [PMID: 17608220]
  • Ji-feng Liu, Xue-mei Zhang, Duo-qing Xue, Zhi-yong Jiang, Qiong Gu, Ji-jun Chen. [Studies on chemical constituents from leaves of Isatis indigotica]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Dec; 31(23):1961-5. doi: . [PMID: 17348190]
  • Ivon E J Milder, Edith J M Feskens, Ilja C W Arts, H Bas Bueno-de-Mesquita, Peter C H Hollman, Daan Kromhout. Intakes of 4 dietary lignans and cause-specific and all-cause mortality in the Zutphen Elderly Study. The American journal of clinical nutrition. 2006 Aug; 84(2):400-5. doi: 10.1093/ajcn/84.1.400. [PMID: 16895890]
  • Heidi Schwartz, Gerhard Sontag. Determination of secoisolariciresinol, lariciresinol and isolariciresinol in plant foods by high performance liquid chromatography coupled with coulometric electrode array detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jul; 838(2):78-85. doi: 10.1016/j.jchromb.2006.03.058. [PMID: 16750660]
  • Ivon E J Milder, Ilja C W Arts, Betty van de Putte, Dini P Venema, Peter C H Hollman. Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol. The British journal of nutrition. 2005 Mar; 93(3):393-402. doi: 10.1079/bjn20051371. [PMID: 15877880]
  • Bao-hua Yang, Wei-dong Zhang, Zheng-bing Gu, Ting-zhao Li, Chuang Zhang, Yun Zhou. [Studies on chemical constituents in bark of Larix olgensis var. koreana]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Feb; 30(4):270-2. doi: . [PMID: 15724403]
  • Shuichi Yamamoto, Angelika Otto, Bernd R T Simoneit. Lignans in resin of Araucaria angustifolia by gas chromatography/mass spectrometry. Journal of mass spectrometry : JMS. 2004 Nov; 39(11):1337-47. doi: 10.1002/jms.726. [PMID: 15532064]
  • Ivon E J Milder, Ilja C W Arts, Dini P Venema, Johan J P Lasaroms, Kristina Wähälä, Peter C H Hollman. Optimization of a liquid chromatography-tandem mass spectrometry method for quantification of the plant lignans secoisolariciresinol, matairesinol, lariciresinol, and pinoresinol in foods. Journal of agricultural and food chemistry. 2004 Jul; 52(15):4643-51. doi: 10.1021/jf0497556. [PMID: 15264894]
  • Ilhan Gurbuz, Nurgun Erdemoglu, Erdem Yesilada, Bilge Sener. Anti-ulcerogenic lignans from Taxus baccata L. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Mar; 59(3-4):233-6. doi: 10.1515/znc-2004-3-420. [PMID: 15241933]
  • Francesca Cutillo, Brigida D'Abrosca, Marina DellaGreca, Antonio Fiorentino, Armando Zarrelli. Lignans and neolignans from Brassica fruticulosa: effects on seed germination and plant growth. Journal of agricultural and food chemistry. 2003 Oct; 51(21):6165-72. doi: 10.1021/jf034644c. [PMID: 14518939]
  • Ting-zhao Li, Wei-dong Zhang, Zheng-bing Gu, Wen-yong Liu, Jing Zhou, Wan-sheng Chen. [Studies on the lignans from Patrinia scabra]. Yao xue xue bao = Acta pharmaceutica Sinica. 2003 Jul; 38(7):520-2. doi: ". [PMID: 14515797]
  • Li-Hua Xie, Teruaki Akao, Kenjiro Hamasaki, Takeshi Deyama, Masao Hattori. Biotransformation of pinoresinol diglucoside to mammalian lignans by human intestinal microflora, and isolation of Enterococcus faecalis strain PDG-1 responsible for the transformation of (+)-pinoresinol to (+)-lariciresinol. Chemical & pharmaceutical bulletin. 2003 May; 51(5):508-15. doi: 10.1248/cpb.51.508. [PMID: 12736449]
  • Toshio Morikawa, Jing Tao, Shin Ando, Hisashi Matsuda, Masayuki Yoshikawa. Absolute stereostructures of new arborinane-type triterpenoids and inhibitors of nitric oxide production from Rubia yunnanensis. Journal of natural products. 2003 May; 66(5):638-45. doi: 10.1021/np0205710. [PMID: 12762798]
  • Tina Sicilia, Heike B Niemeyer, Doris M Honig, Manfred Metzler. Identification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. Journal of agricultural and food chemistry. 2003 Feb; 51(5):1181-8. doi: 10.1021/jf0207979. [PMID: 12590454]
  • 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]
  • D R Gang, H Kasahara, Z Q Xia, K Vander Mijnsbrugge, G Bauw, W Boerjan, M Van Montagu, L B Davin, N G Lewis. Evolution of plant defense mechanisms. Relationships of phenylcoumaran benzylic ether reductases to pinoresinol-lariciresinol and isoflavone reductases. The Journal of biological chemistry. 1999 Mar; 274(11):7516-27. doi: 10.1074/jbc.274.11.7516. [PMID: 10066819]
  • 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]
  • A F Barrero, A Haïdour, M Muñoz Dorado. Lignans from the wood of Abies pinsapo. Journal of natural products. 1994 Jun; 57(6):713-9. doi: 10.1021/np50108a005. [PMID: 7931362]
  • C Bannwart, H Adlercreutz, K Wähälä, G Brunow, T Hase. Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine. Clinica chimica acta; international journal of clinical chemistry. 1989 Apr; 180(3):293-301. doi: 10.1016/0009-8981(89)90011-9. [PMID: 2545375]
  • C Y Duh, C H Phoebe, J M Pezzuto, A D Kinghorn, N R Farnsworth. Plant anticancer agents, XLII. Cytotoxic constituents from Wikstroemia elliptica. Journal of natural products. 1986 Jul; 49(4):706-9. doi: 10.1021/np50046a031. [PMID: 3783168]
  • . . . . doi: . [PMID: 18489708]
  • . . . . doi: . [PMID: 17257599]