Medicarpin (BioDeep_00000000959)

 

Secondary id: BioDeep_00000180701, BioDeep_00000403167, BioDeep_00000869063

natural product PANOMIX_OTCML-2023


代谢物信息卡片


9-Methoxy-6a,11a-dimethyl-6a,11a-dihydro-6H-\ 1-benzofuro[3,2-c]chromen-3-ol from Dalbergia Oliveri

化学式: C16H14O4 (270.0892044)
中文名称: (+)-美迪紫檀素, 美迪紫檀素, 美迪紫檀素, 美迪紫檀素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.13%

分子结构信息

SMILES: c1(ccc2c(c1)OC[C@@H]1[C@H]2Oc2c1ccc(c2)OC)O
InChI: InChI=1S/C16H14O4/c1-18-10-3-5-11-13-8-19-14-6-9(17)2-4-12(14)16(13)20-15(11)7-10/h2-7,13,16-17H,8H2,1H3

描述信息

A member of the class of pterocarpans that is 3-hydroxyptercarpan with a methoxy substituent at position 9.
(+)-medicarpin is the (+)-enantiomer of medicarpin. It is an enantiomer of a (-)-medicarpin.
(+)-Medicarpin is a natural product found in Dalbergia sissoo, Machaerium acutifolium, and other organisms with data available.
The (+)-enantiomer of medicarpin.
(-)-medicarpin is the (-)-enantiomer of medicarpin. It has a role as a plant metabolite. It is an enantiomer of a (+)-medicarpin.
Medicarpin is a natural product found in Cicer chorassanicum, Melilotus dentatus, and other organisms with data available.
See also: Glycyrrhiza uralensis Root (part of); Medicago sativa whole (part of).
The (-)-enantiomer of medicarpin.
Medicarpin is a flavonoid isolated from Medicago sativa. Medicarpin induces apoptosis and overcome multidrug resistance in leukemia P388 cells by modulating P-gp-mediated efflux of agents[1].
Medicarpin is a flavonoid isolated from Medicago sativa. Medicarpin induces apoptosis and overcome multidrug resistance in leukemia P388 cells by modulating P-gp-mediated efflux of agents[1].

同义名列表

60 个代谢物同义名

Medicarpin; 9-Methoxy-6a,11a-dimethyl-6a,11a-dihydro-6H-\ 1-benzofuro[3,2-c]chromen-3-ol from Dalbergia Oliveri; (1S,10S)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0?,?.0??,??]heptadeca-2(7),3,5,11,13,15-hexaen-5-ol; (6aS,11aS)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol; (6aS,11aS)-9-methoxy-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-3-ol; (6aS,11aS)-Demethylhomopterocarpin; 3-Hydroxy-9-methoxypterocarpan; (+)-(6aS,11aS)-medicarpin; (6aS, 11aS)-Medicarpin; (6As,11As)-Medicarpan; (6As,11As)-Medicarpin; (+/-)-Medicarpin; (+)-Medicarpin; (+)-Medicrpin; (1R,10R)-14-methoxy-8,17-dioxatetracyclo[8.7.0.0?,?.0??,??]heptadeca-2,4,6,11,13,15-hexaen-5-ol; 6H-Benzofuro[3,2-c][1]benzopyran-3-ol,6a,11a-dihydro-9-methoxy-,(6ar,11ar)-rel-; 6H-Benzofuro[3, 2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, (6aR-cis)-; 6H-Benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-,(6aR,11aR)-; 6H-Benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, (6aR-cis)-; 6H-Benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, cis-(-)-; (6AR,11AR)-6A,11A-DIHYDRO-9-METHOXY-6H-BENZOFURO(3,2-C)(1)BENZOPYRAN-3-OL; rel-(6aR,11aR)-9-Methoxy-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-3-ol; (6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-(1)benzofuro(3,2-c)chromen-3-ol; 6H-Benzofuro(3,2-c)(1)benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, cis-; (6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol; 6H-Benzofuro[3,2-c][1]benzopyran-3-ol, 6a,11a-dihydro-9-methoxy-, cis-; (6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-3-ol; 9-Methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-ol, cis-; 6a,11a-dihydro-9-methoxy-6H-benzofuro(3,2-c)(1)benzopyran-3-ol; 6H-Benzofuro[3, 6a,11a-dihydro-9-methoxy-, (6aR-cis)-; 6H-Benzofuro[3, 6a,11a-dihydro-9-methoxy-, cis-; 3-Hydroxy-9-methoxypterocarpan, (-); (-)-3-Hydroxy-9-methoxypterocarpan; (4-Ethoxyphenyl)-oxo-acetonitrile; l-3-Hydroxy-9-methoxypterocarpan; (l)-De-o-methylhomopterocarpan; medicarpin, (cis-(+-))-isomer; medicarpin, (6aS-cis)-isomer; NSRJSISNDPOJOP-BBRMVZONSA-N; (-)-Demethylhomopterocarpin; Demethylhomopterocarpin; (6aR,11aR)-medicarpin; Medicarpin, (-)-; UNII-6TX086I6IG; MEDICARPIN [MI]; (-) Medicarpin; (-)-Medicarpin; MEGxp0_001319; NCI60_003118; ACon1_001568; 6TX086I6IG; (6aR,11aR)-6a,11a-dihydro-9-methoxy-6H-benzofuro[3,2c][1]benzopyran-3-ol; (6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzoxolo[3,2-c]chromen-3-ol; (6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-benzofurano[3,2-c]chromen-3-ol; CHEBI:16114; AIDS-031298; 32383-76-9; AIDS031298; NSC350085; C10503



数据库引用编号

38 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(3)

代谢反应

43 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(6)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(34)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

440 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

  • Arunima Gupta, Pallavi Awasthi, Neha Sharma, Sajiya Parveen, Ravi P Vats, Nirpendra Singh, Yashwant Kumar, Atul Goel, Divya Chandran. Medicarpin confers powdery mildew resistance in Medicago truncatula and activates the salicylic acid signalling pathway. Molecular plant pathology. 2022 07; 23(7):966-983. doi: 10.1111/mpp.13202. [PMID: 35263504]
  • Chang-Ming Chern, Chung-Kuang Lu, Kuo-Tong Liou, Yea-Hwey Wang, Keng-Chang Tsai, Chia-Lin Chang, Chia-Che Chang, Yuh-Chiang Shen. Medicarpin isolated from Radix Hedysari ameliorates brain injury in a murine model of cerebral ischemia. Journal of food and drug analysis. 2021 12; 29(4):581-605. doi: 10.38212/2224-6614.3377. [PMID: 35649147]
  • Dongli Li, Chuipu Cai, Yanfang Liao, Qihui Wu, Hanzhong Ke, Pengfei Guo, Qi Wang, Banghan Ding, Jiansong Fang, Shuhuan Fang. Systems pharmacology approach uncovers the therapeutic mechanism of medicarpin against scopolamine-induced memory loss. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Oct; 91(?):153662. doi: 10.1016/j.phymed.2021.153662. [PMID: 34333326]
  • Yan Li, Jie-Wei Wu, Hai-Bo Tan, Bai-Lin Li, Sheng-Xiang Qiu. Three new pterocarpans from the aerial parts of Abrus Precatorius. Natural product research. 2020 Jul; 34(13):1836-1844. doi: 10.1080/14786419.2018.1564293. [PMID: 31328559]
  • Gari Vidal Ccana-Ccapatinta, Jennyfer Andrea Aldana Mejía, Matheus Hikaru Tanimoto, Milton Groppo, Jean Carlos Andrade Sarmento de Carvalho, Jairo Kenupp Bastos. Dalbergia ecastaphyllum (L.) Taub. and Symphonia globulifera L.f.: The Botanical Sources of Isoflavonoids and Benzophenones in Brazilian Red Propolis. Molecules (Basel, Switzerland). 2020 Apr; 25(9):. doi: 10.3390/molecules25092060. [PMID: 32354180]
  • Fatma Tuğçe Gürağaç Dereli, Haroon Khan, Eduardo Sobarzo-Sánchez, Esra Küpeli Akkol. Antidepressant Potential of Lotus corniculatus L. subsp. corniculatus: An Ethnobotany Based Approach. Molecules (Basel, Switzerland). 2020 Mar; 25(6):. doi: 10.3390/molecules25061299. [PMID: 32178424]
  • Isha Taneja, Ashutosh Raghuvanshi, Kanumuri Siva Rama Raju, Pallavi Awasthi, Mamunur Rashid, Sandeep Singh, Atul Goel, Sheelendra Pratap Singh, Muhammad Wahajuddin. Bioavailability, tissue distribution and excretion studies of a potential anti-osteoporotic agent, medicarpin, in female rats using validated LC-MS/MS method. Journal of pharmaceutical and biomedical analysis. 2020 Feb; 180(?):112978. doi: 10.1016/j.jpba.2019.112978. [PMID: 31855725]
  • Hong-Yan Wang, Teng Li, Rui Ji, Feng Xu, Guang-Xue Liu, Yao-Li Li, Ming-Ying Shang, Shao-Qing Cai. Metabolites of Medicarpin and Their Distributions in Rats. Molecules (Basel, Switzerland). 2019 May; 24(10):. doi: 10.3390/molecules24101966. [PMID: 31121832]
  • Aleksandra Golonko, Tomasz Pienkowski, Renata Swislocka, Ryszard Lazny, Marek Roszko, Wlodzimierz Lewandowski. Another look at phenolic compounds in cancer therapy the effect of polyphenols on ubiquitin-proteasome system. European journal of medicinal chemistry. 2019 Apr; 167(?):291-311. doi: 10.1016/j.ejmech.2019.01.044. [PMID: 30776692]
  • John Nii Addotey, Isabelle Lengers, Joachim Jose, Nóra Gampe, Szabolcs Béni, Frank Petereit, Andreas Hensel. Isoflavonoids with inhibiting effects on human hyaluronidase-1 and norneolignan clitorienolactone B from Ononis spinosa L. root extract. Fitoterapia. 2018 Oct; 130(?):169-174. doi: 10.1016/j.fitote.2018.08.013. [PMID: 30176279]
  • Upinder S Gill, Srinivasa R Uppalapati, Lina Gallego-Giraldo, Yasuhiro Ishiga, Richard A Dixon, Kirankumar S Mysore. Metabolic flux towards the (iso)flavonoid pathway in lignin modified alfalfa lines induces resistance against Fusarium oxysporum f. sp. medicaginis. Plant, cell & environment. 2018 09; 41(9):1997-2007. doi: 10.1111/pce.13093. [PMID: 29047109]
  • Tao Jiang, Kaifu Li, Honghai Liu, Lin Yang. Extraction of biomedical compounds from the wood of Pterocarpus macarocarpus Kurz heartwood. Pakistan journal of pharmaceutical sciences. 2018 May; 31(3):913-918. doi: . [PMID: 29716873]
  • Khan Mohammad Imran, Dahyeon Yoon, Tae-Jin Lee, Yong-Sik Kim. Medicarpin induces lipolysis via activation of Protein Kinase A in brown adipocytes. BMB reports. 2018 May; 51(5):249-254. doi: 10.5483/bmbrep.2018.51.5.228. [PMID: 29353597]
  • Khan Mohammad Imran, Dahyeon Yoon, Yong-Sik Kim. A pivotal role of AMPK signaling in medicarpin-mediated formation of brown and beige. BioFactors (Oxford, England). 2018 Mar; 44(2):168-179. doi: 10.1002/biof.1392. [PMID: 29064586]
  • Rajni Sharma, Linda Gatchie, Ibidapo S Williams, Shreyans K Jain, Ram A Vishwakarma, Bhabatosh Chaudhuri, Sandip B Bharate. Glycyrrhiza glabra extract and quercetin reverses cisplatin resistance in triple-negative MDA-MB-468 breast cancer cells via inhibition of cytochrome P450 1B1 enzyme. Bioorganic & medicinal chemistry letters. 2017 12; 27(24):5400-5403. doi: 10.1016/j.bmcl.2017.11.013. [PMID: 29150398]
  • Wanda Biala, Joanna Banasiak, Karolina Jarzyniak, Aleksandra Pawela, Michal Jasinski. Medicago truncatula ABCG10 is a transporter of 4-coumarate and liquiritigenin in the medicarpin biosynthetic pathway. Journal of experimental botany. 2017 06; 68(12):3231-3241. doi: 10.1093/jxb/erx059. [PMID: 28369642]
  • Xinzhou Yang, Shihao Deng, Mi Huang, Jialin Wang, Li Chen, Mingrui Xiong, Jie Yang, Sijiang Zheng, Xinhua Ma, Ping Zhao, Yunjiang Feng. Chemical constituents from Sophora tonkinensis and their glucose transporter 4 translocation activities. Bioorganic & medicinal chemistry letters. 2017 03; 27(6):1463-1466. doi: 10.1016/j.bmcl.2017.01.078. [PMID: 28236591]
  • Chelliah Selvam, Brian C Jordan, Sandhya Prakash, Daniel Mutisya, Ramasamy Thilagavathi. Pterocarpan scaffold: A natural lead molecule with diverse pharmacological properties. European journal of medicinal chemistry. 2017 Mar; 128(?):219-236. doi: 10.1016/j.ejmech.2017.01.023. [PMID: 28189086]
  • Kaitlin Deardorff, William Ray, Eric Winterstein, MacKenzie Brown, Jocelyn McCornack, Brianda Cardenas-Garcia, Kiah Jones, Sarah McNutt, Shannon Fulkerson, Daneel Ferreira, Charlotte Gény, Xiaoyan Chen, Gil Belofsky, Blaise Dondji. Phenolic Metabolites of Dalea ornata Affect Both Survival and Motility of the Human Pathogenic Hookworm Ancylostoma ceylanicum. Journal of natural products. 2016 09; 79(9):2296-303. doi: 10.1021/acs.jnatprod.6b00444. [PMID: 27584977]
  • Nóra Gampe, András Darcsi, Szilvia Lohner, Szabolcs Béni, László Kursinszki. Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC-MS/MS and NMR. Journal of pharmaceutical and biomedical analysis. 2016 May; 123(?):74-81. doi: 10.1016/j.jpba.2016.01.058. [PMID: 26874257]
  • Grégory Gatouillat, Abdulmagid Alabdul Magid, Eric Bertin, Hassan El btaouri, Hamid Morjani, Catherine Lavaud, Claudie Madoulet. Medicarpin and millepurpan, two flavonoids isolated from Medicago sativa, induce apoptosis and overcome multidrug resistance in leukemia P388 cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 Dec; 22(13):1186-94. doi: 10.1016/j.phymed.2015.09.005. [PMID: 26598918]
  • Lotfi Ghribi, Pierre Waffo-Téguo, Stéphanie Cluzet, Axel Marchal, Jessica Marques, Jean-Michel Mérillon, Hichem Ben Jannet. Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L. Bioorganic & medicinal chemistry letters. 2015 Sep; 25(18):3825-30. doi: 10.1016/j.bmcl.2015.07.076. [PMID: 26248805]
  • Isha Taneja, Kanumuri Siva Rama Raju, Muralikrishna Challagundla, Ashutosh Raghuvanshi, Atul Goel, Muhammad Wahajuddin. LC-ESI-MS/MS method for bioanalytical determination of osteogenic phytoalexin, medicarpin, and its application to preliminary pharmacokinetic studies in rats. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Sep; 1001(?):9-16. doi: 10.1016/j.jchromb.2015.06.025. [PMID: 26241182]
  • Yasuhiro Ishiga, Srinivasa Rao Uppalapati, Upinder S Gill, David Huhman, Yuhong Tang, Kirankumar S Mysore. Transcriptomic and metabolomic analyses identify a role for chlorophyll catabolism and phytoalexin during Medicago nonhost resistance against Asian soybean rust. Scientific reports. 2015 Aug; 5(?):13061. doi: 10.1038/srep13061. [PMID: 26267598]
  • Patrícia C Bezerra-Silva, Jefferson C Santos, Geanne K N Santos, Kamilla A Dutra, Andrea L B D Santana, Claudia A Maranhão, Márcia S Nascimento, Daniela M A F Navarro, Lothar W Bieber. Extract of Bowdichia virgilioides and maackiain as larvicidal agent against Aedes aegypti mosquito. Experimental parasitology. 2015 Jun; 153(?):160-4. doi: 10.1016/j.exppara.2015.03.018. [PMID: 25819294]
  • Sima Ghelich, Fatemeh Zarinkamar, Bahram Mohammad Soltani, Vahid Niknam. Effect of lead treatment on medicarpin accumulation and on the gene expression of key enzymes involved in medicarpin biosynthesis in Medicago sativa L. Environmental science and pollution research international. 2014 Dec; 21(24):14091-8. doi: 10.1007/s11356-014-3335-4. [PMID: 25053287]
  • R Trivedi, R Maurya, D P Mishra. Medicarpin, a legume phytoalexin sensitizes myeloid leukemia cells to TRAIL-induced apoptosis through the induction of DR5 and activation of the ROS-JNK-CHOP pathway. Cell death & disease. 2014 Oct; 5(?):e1465. doi: 10.1038/cddis.2014.429. [PMID: 25321472]
  • Hao Wang, Wen-Li Mei, Zhi-Kai Guo, Zhan-Feng Xia, Hui-Min Zhong, Hao-Fu Dai. [Chemical constituents of Dalbergia odorifera]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 May; 39(9):1625-9. doi: . [PMID: 25095373]
  • N F Kushnerova, S A Fedoreev, S E Fomenko, V G Sprygin, N I Kulesh, N P Mishchenko, M V Veselova, T V Momot. [Hepatoprotective properties of isoflavonoids from roots of Maackia amurensis on experimental carbon tetrachloride-induced hepatic damage]. Eksperimental'naia i klinicheskaia farmakologiia. 2014; 77(2):26-30. doi: . [PMID: 24791337]
  • Chul Lee, Jin Woo Lee, Qinghao Jin, Dae Sik Jang, Sung-Joon Lee, Dongho Lee, Jin Tae Hong, Youngsoo Kim, Mi Kyeong Lee, Bang Yeon Hwang. Inhibitory constituents of the heartwood of Dalbergia odorifera on nitric oxide production in RAW 264.7 macrophages. Bioorganic & medicinal chemistry letters. 2013 Jul; 23(14):4263-6. doi: 10.1016/j.bmcl.2013.04.032. [PMID: 23743282]
  • Agnieszka Kicel, Maria Wolbiś. Study on the phenolic constituents of the flowers and leaves of Trifolium repens L. Natural product research. 2012 Nov; 26(21):2050-4. doi: 10.1080/14786419.2011.637217. [PMID: 22117193]
  • Achref Aloui, Eliane Dumas-Gaudot, Zeina Daher, Diederik van Tuinen, Samira Aschi-Smit, Dominique Morandi. Influence of arbuscular mycorrhizal colonisation on cadmium induced Medicago truncatula root isoflavonoid accumulation. Plant physiology and biochemistry : PPB. 2012 Nov; 60(?):233-9. doi: 10.1016/j.plaphy.2012.08.014. [PMID: 23000816]
  • A M Tyagi, K Srivastava, J Kureel, A Kumar, A Raghuvanshi, D Yadav, R Maurya, A Goel, D Singh. Premature T cell senescence in Ovx mice is inhibited by repletion of estrogen and medicarpin: a possible mechanism for alleviating bone loss. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA. 2012 Mar; 23(3):1151-61. doi: 10.1007/s00198-011-1650-x. [PMID: 21562872]
  • Zhi Liu, Jie Zhao, Yunhe Li, Wenwei Zhang, Guiliang Jian, Yufa Peng, Fangjun Qi. Non-uniform distribution pattern for differentially expressed genes of transgenic rice Huahui 1 at different developmental stages and environments. PloS one. 2012; 7(5):e37078. doi: 10.1371/journal.pone.0037078. [PMID: 22606331]
  • Kanok-On Rayanil, Pastraporn Bunchornmaspan, Pittaya Tuntiwachwuttikul. A new phenolic compound with anticancer activity from the wood of Millettia leucantha. Archives of pharmacal research. 2011 Jun; 34(6):881-6. doi: 10.1007/s12272-011-0603-4. [PMID: 21725807]
  • Sang Hee Shim. 20S proteasome inhibitory activity of flavonoids isolated from Spatholobus suberectus. Phytotherapy research : PTR. 2011 Apr; 25(4):615-8. doi: 10.1002/ptr.3342. [PMID: 21104764]
  • Marek Mutwil, Sebastian Klie, Takayuki Tohge, Federico M Giorgi, Olivia Wilkins, Malcolm M Campbell, Alisdair R Fernie, Björn Usadel, Zoran Nikoloski, Staffan Persson. PlaNet: combined sequence and expression comparisons across plant networks derived from seven species. The Plant cell. 2011 Mar; 23(3):895-910. doi: 10.1105/tpc.111.083667. [PMID: 21441431]
  • Jiyoung Seo, Su-Il Kang, Dongho Won, Mihyang Kim, Ji-Young Ryu, Suk-Woo Kang, Byung-Hun Um, Cheol-Ho Pan, Joong-Hoon Ahn, Youhoon Chong, Robert A Kanaly, Jaehong Han, Hor-Gil Hur. Absolute configuration-dependent epoxide formation from isoflavan-4-ol stereoisomers by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes strain KF707. Applied microbiology and biotechnology. 2011 Mar; 89(6):1773-82. doi: 10.1007/s00253-010-2989-1. [PMID: 21063701]
  • Caren Rodriguez-Medina, Craig A Atkins, Anthea J Mann, Megan E Jordan, Penelope Mc Smith. Macromolecular composition of phloem exudate from white lupin (Lupinus albus L.). BMC plant biology. 2011 Feb; 11(?):36. doi: 10.1186/1471-2229-11-36. [PMID: 21342527]
  • Rajib Saha, Patrick F Suthers, Costas D Maranas. Zea mays iRS1563: a comprehensive genome-scale metabolic reconstruction of maize metabolism. PloS one. 2011; 6(7):e21784. doi: 10.1371/journal.pone.0021784. [PMID: 21755001]
  • Chun Whan Choi, Yeon Hee Choi, Mi-Ran Cha, Dae Seok Yoo, Young Sup Kim, Gyu Hwan Yon, Kyung Sik Hong, Young Ho Kim, Shi Yong Ryu. Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose. Journal of agricultural and food chemistry. 2010 Sep; 58(18):9988-93. doi: 10.1021/jf101926j. [PMID: 20734984]
  • Rashmi Pandey, Abnish K Gautam, Biju Bhargavan, Ritu Trivedi, Gaurav Swarnkar, Geet K Nagar, Dinesh K Yadav, Manmeet Kumar, Preeti Rawat, Lakshmi Manickavasagam, Amit Kumar, Rakesh Maurya, Atul Goel, Girish K Jain, Naibedya Chattopadhyay, Divya Singh. Total extract and standardized fraction from the stem bark of Butea monosperma have osteoprotective action: evidence for the nonestrogenic osteogenic effect of the standardized fraction. Menopause (New York, N.Y.). 2010 May; 17(3):602-10. doi: 10.1097/gme.0b013e3181d0f7f0. [PMID: 20395887]
  • Yi Liu, Yuying Zhao, Hubiao Chen, Bin Wang, Qingying Zhang. Chemical analysis of the principal flavonoids of Radix Hedysari by HPLC. Natural product communications. 2010 Apr; 5(4):541-4. doi: ". [PMID: 20433068]
  • Hamid Sobhanian, Roya Razavizadeh, Yohei Nanjo, Ali Akbar Ehsanpour, Ferdous Rastgar Jazii, Nasrin Motamed, Setsuko Komatsu. Proteome analysis of soybean leaves, hypocotyls and roots under salt stress. Proteome science. 2010 Mar; 8(?):19. doi: 10.1186/1477-5956-8-19. [PMID: 20350314]
  • Mukesh Jain, Challa Ghanashyam, Annapurna Bhattacharjee. Comprehensive expression analysis suggests overlapping and specific roles of rice glutathione S-transferase genes during development and stress responses. BMC genomics. 2010 Jan; 11(?):73. doi: 10.1186/1471-2164-11-73. [PMID: 20109239]
  • Jing Liu, Xuguang Hu, Quan Yang, Zhiling Yu, Zhongzhen Zhao, Tao Yi, Hubiao Chen. Comparison of the immunoregulatory function of different constituents in radix astragali and radix hedysari. Journal of biomedicine & biotechnology. 2010; 2010(?):479426. doi: 10.1155/2010/479426. [PMID: 20224658]
  • Michał Jasiński, Piotr Kachlicki, Paweł Rodziewicz, Marek Figlerowicz, Maciej Stobiecki. Changes in the profile of flavonoid accumulation in Medicago truncatula leaves during infection with fungal pathogen Phoma medicaginis. Plant physiology and biochemistry : PPB. 2009 Sep; 47(9):847-53. doi: 10.1016/j.plaphy.2009.05.004. [PMID: 19541494]
  • Marcello Iriti, Franco Faoro. Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution. International journal of molecular sciences. 2009 Jul; 10(8):3371-3399. doi: 10.3390/ijms10083371. [PMID: 20111684]
  • Xin-Kai Zong, Fu-Li Lai, Zhu-Nian Wang, Jian-Rong Wang. [Studies on chemical constituents of root of Millettia speciosa]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Apr; 32(4):520-1. doi: . [PMID: 19645236]
  • Marina A Naoumkina, XianZhi He, Richard A Dixon. Elicitor-induced transcription factors for metabolic reprogramming of secondary metabolism in Medicago truncatula. BMC plant biology. 2008 Dec; 8(?):132. doi: 10.1186/1471-2229-8-132. [PMID: 19102779]
  • Bruno B Silva, Pedro L Rosalen, Jaime A Cury, Masaharu Ikegaki, Vinícius C Souza, Alessandro Esteves, Severino M Alencar. Chemical composition and botanical origin of red propolis, a new type of brazilian propolis. Evidence-based complementary and alternative medicine : eCAM. 2008 Sep; 5(3):313-6. doi: 10.1093/ecam/nem059. [PMID: 18830449]
  • Sergey A Fedoreyev, Victor P Bulgakov, Olga V Grishchenko, Marina V Veselova, Olga E Krivoschekova, Nadezda I Kulesh, Vladimir A Denisenko, Galina K Tchernoded, Yury N Zhuravlev. Isoflavonoid composition of a callus culture of the relict tree Maackia amurensis Rupr. et Maxim. Journal of agricultural and food chemistry. 2008 Aug; 56(16):7023-31. doi: 10.1021/jf801227q. [PMID: 18671403]
  • Yuki Tsunoda, Masafumi Okawa, Junei Kinjo, Tsuyoshi Ikeda, Toshihiro Nohara. Studies on the constituents of Gueldenstaedtia multiflora. Chemical & pharmaceutical bulletin. 2008 Aug; 56(8):1138-42. doi: 10.1248/cpb.56.1138. [PMID: 18670114]
  • Michael C Puckette, Yuhong Tang, Ramamurthy Mahalingam. Transcriptomic changes induced by acute ozone in resistant and sensitive Medicago truncatula accessions. BMC plant biology. 2008 Apr; 8(?):46. doi: 10.1186/1471-2229-8-46. [PMID: 18433496]
  • Suresh Awale, Feng Li, Hiroko Onozuka, Hiroyasu Esumi, Yasuhiro Tezuka, Shigetoshi Kadota. Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition. Bioorganic & medicinal chemistry. 2008 Jan; 16(1):181-9. doi: 10.1016/j.bmc.2007.10.004. [PMID: 17950610]
  • Gardenia C G Militão, Sávio M Pinheiro, Ivana N F Dantas, Cláudia Pessoa, Manoel Odorico de Moraes, Leti Cia V Costa-Lotufo, Mary Anne S Lima, Edilberto R Silveira. Bioassay-guided fractionation of pterocarpans from roots of Harpalyce brasiliana Benth. Bioorganic & medicinal chemistry. 2007 Nov; 15(21):6687-91. doi: 10.1016/j.bmc.2007.08.011. [PMID: 17764956]
  • Hui Shao, Richard A Dixon, Xiaoqiang Wang. Crystal structure of vestitone reductase from alfalfa (Medicago sativa L.). Journal of molecular biology. 2007 May; 369(1):265-76. doi: 10.1016/j.jmb.2007.03.040. [PMID: 17433362]
  • Norimoto Shimada, Shusei Sato, Tomoyoshi Akashi, Yasukazu Nakamura, Satoshi Tabata, Shin-Ichi Ayabe, Toshio Aoki. Genome-wide analyses of the structural gene families involved in the legume-specific 5-deoxyisoflavonoid biosynthesis of Lotus japonicus. DNA research : an international journal for rapid publication of reports on genes and genomes. 2007 Feb; 14(1):25-36. doi: 10.1093/dnares/dsm004. [PMID: 17452423]
  • Chang-Jun Liu, Bettina E Deavours, Stéphane B Richard, Jean-Luc Ferrer, Jack W Blount, David Huhman, Richard A Dixon, Joseph P Noel. Structural basis for dual functionality of isoflavonoid O-methyltransferases in the evolution of plant defense responses. The Plant cell. 2006 Dec; 18(12):3656-69. doi: 10.1105/tpc.106.041376. [PMID: 17172354]
  • James David Adams, Rubin Wang, Jun Yang, Eric Jungchi Lien. Preclinical and clinical examinations of Salvia miltiorrhiza and its tanshinones in ischemic conditions. Chinese medicine. 2006 Nov; 1(?):3. doi: 10.1186/1749-8546-1-3. [PMID: 17302964]
  • Jong Min Kim, Yun Mi Lee, Ga Young Lee, Dae Sik Jang, Ki Hwan Bae, Jin Sook Kim. Constituents of the roots of Pueraria lobata inhibit formation of advanced glycation end products (AGEs). Archives of pharmacal research. 2006 Oct; 29(10):821-5. doi: 10.1007/bf02973900. [PMID: 17121174]
  • Yi Liu, Hu-Biao Chen, Yu-Ying Zhao, Bin Wang, Qing-Ying Zhang, Lei Zhang, Pengfei Tu. Quantification and stability studies on the flavonoids of Radix hedysari. Journal of agricultural and food chemistry. 2006 Sep; 54(18):6634-9. doi: 10.1021/jf061335o. [PMID: 16939320]
  • Gil Belofsky, Roberto Carreno, Kim Lewis, Anthony Ball, Gabriele Casadei, George P Tegos. Metabolites of the 'smoke tree', Dalea spinosa, potentiate antibiotic activity against multidrug-resistant Staphylococcus aureus. Journal of natural products. 2006 Feb; 69(2):261-4. doi: 10.1021/np058057s. [PMID: 16499327]
  • Rong-Xia Liu, Qiao Wang, Hong-Zhu Guo, Li Li, Kai-Shun Bi, De-An Guo. Simultaneous determination of 10 major flavonoids in Dalbergia odorifera by high performance liquid chromatography. Journal of pharmaceutical and biomedical analysis. 2005 Sep; 39(3-4):469-76. doi: 10.1016/j.jpba.2005.04.007. [PMID: 15935596]
  • S F Wang, T J Ridsdill-Smith, E L Ghisalberti. Chemical defenses of Trifolium glanduliferum against redlegged earth mite Halotydeus destructor. Journal of agricultural and food chemistry. 2005 Aug; 53(16):6240-5. doi: 10.1021/jf0502202. [PMID: 16076100]
  • Bettina E Deavours, Richard A Dixon. Metabolic engineering of isoflavonoid biosynthesis in alfalfa. Plant physiology. 2005 Aug; 138(4):2245-59. doi: 10.1104/pp.105.062539. [PMID: 16006598]
  • A S Saratikov, V S Chuchalin, A V Rat'kin, E V Rat'kin, S A Fedoreev, V P Bulgakov. [Hepatoprotector properties of polyphenolic complexes from wood and cell culture of Maackia amurensis]. Eksperimental'naia i klinicheskaia farmakologiia. 2005 Mar; 68(2):51-4. doi: . [PMID: 15934369]
  • Katja Schwalm, Roni Aloni, Markus Langhans, Werner Heller, Susanne Stich, Cornelia I Ullrich. Flavonoid-related regulation of auxin accumulation in Agrobacterium tumefaciens-induced plant tumors. Planta. 2003 Dec; 218(2):163-78. doi: 10.1007/s00425-003-1104-6. [PMID: 14523649]
  • Richard A Dixon, Lloyd W Sumner. Legume natural products: understanding and manipulating complex pathways for human and animal health. Plant physiology. 2003 Mar; 131(3):878-85. doi: 10.1104/pp.102.017319. [PMID: 12644640]
  • Li-qian Hai, Hong Liang, Yu-ying Zhao, Nian-sheng Du. [Studies on chemical constituents in the root of Hedysarum polybotrys]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2002 Nov; 27(11):843-5. doi: ". [PMID: 12776590]
  • Wei Li, Kazuo Koike, Yoshihisa Asada, Masao Hirotani, Hekai Rui, Takafumi Yoshikawa, Tamotsu Nikaido. Flavonoids from Glycyrrhiza pallidiflora hairy root cultures. Phytochemistry. 2002 Jun; 60(4):351-5. doi: 10.1016/s0031-9422(02)00093-6. [PMID: 12031424]
  • Brandi R Baggett, John D Cooper, Eric T Hogan, Jason Carper, Nancy L Paiva, Joel T Smith. Profiling isoflavonoids found in legume root extracts using capillary electrophoresis. Electrophoresis. 2002 Jun; 23(11):1642-51. doi: 10.1002/1522-2683(200206)23:11<1642::aid-elps1642>3.0.co;2-y. [PMID: 12179983]
  • Zhen-Li Liu, Sachiko Tanaka, Hiroshi Horigome, Toshihiko Hirano, Kitaro Oka. Induction of apoptosis in human lung fibroblasts and peripheral lymphocytes in vitro by Shosaiko-to derived phenolic metabolites. Biological & pharmaceutical bulletin. 2002 Jan; 25(1):37-41. doi: 10.1248/bpb.25.37. [PMID: 11824553]
  • Philippe Thoquet, Michele Ghérardi, Etienne-Pascal Journet, Attila Kereszt, Jean-Michel Ané, Jean-Marie Prosperi, Thierry Huguet. The molecular genetic linkage map of the model legume Medicago truncatula: an essential tool for comparative legume genomics and the isolation of agronomically important genes. BMC plant biology. 2002; 2(?):1. doi: 10.1186/1471-2229-2-1. [PMID: 11825338]
  • C J Liu, R A Dixon. Elicitor-induced association of isoflavone O-methyltransferase with endomembranes prevents the formation and 7-O-methylation of daidzein during isoflavonoid phytoalexin biosynthesis. The Plant cell. 2001 Dec; 13(12):2643-58. doi: 10.1105/tpc.010382. [PMID: 11752378]
  • E K Seo, N C Kim, Q Mi, H Chai, M E Wall, M C Wani, H A Navarro, J P Burgess, J G Graham, F Cabieses, G T Tan, N R Farnsworth, J M Pezzuto, A D Kinghorn. Macharistol, a new cytotoxic cinnamylphenol from the stems of Machaerium aristulatum. Journal of natural products. 2001 Nov; 64(11):1483-5. doi: 10.1021/np0103158. [PMID: 11720542]
  • M S Abdel-Kader. Phenolic constituents of Ononis vaginalis roots. Planta medica. 2001 Jun; 67(4):388-90. doi: 10.1055/s-2001-14325. [PMID: 11458469]
  • V A Yaylayan, J R Paré, G Matni, J M Bélanger. MAP: microwave-assisted extraction of fatty acids and Py/GC/MS analysis of selected insects. Natural product letters. 2001; 15(3):187-95. doi: 10.1080/10575630108041279. [PMID: 11858551]
  • D J Allen, J C Gray, N L Paiva, J T Smith. An enantiomeric assay for the flavonoids medicarpin and vestitone using capillary electrophoresis. Electrophoresis. 2000 Jun; 21(10):2051-7. doi: 10.1002/1522-2683(20000601)21:10<2051::aid-elps2051>3.0.co;2-6. [PMID: 10879965]
  • J C Le Bail, Y Champavier, A J Chulia, G Habrioux. Effects of phytoestrogens on aromatase, 3beta and 17beta-hydroxysteroid dehydrogenase activities and human breast cancer cells. Life sciences. 2000 Feb; 66(14):1281-91. doi: 10.1016/s0024-3205(00)00435-5. [PMID: 10755463]
  • X Z He, J T Reddy, R A Dixon. Stress responses in alfalfa (Medicago sativa L). XXII. cDNA cloning and characterization of an elicitor-inducible isoflavone 7-O-methyltransferase. Plant molecular biology. 1998 Jan; 36(1):43-54. doi: 10.1023/a:1005938121453. [PMID: 9484461]
  • L C Chang, C Gerhäuser, L Song, N R Farnsworth, J M Pezzuto, A D Kinghorn. Activity-guided isolation of constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase. Journal of natural products. 1997 Sep; 60(9):869-73. doi: 10.1021/np970236p. [PMID: 9322358]
  • T Fahrendorf, W Ni, B S Shorrosh, R A Dixon. Stress responses in alfalfa (Medicago sativa L.) XIX. Transcriptional activation of oxidative pentose phosphate pathway genes at the onset of the isoflavonoid phytoalexin response. Plant molecular biology. 1995 Aug; 28(5):885-900. doi: 10.1007/bf00042073. [PMID: 7640360]
  • N L Paiva, R Edwards, Y J Sun, G Hrazdina, R A Dixon. Stress responses in alfalfa (Medicago sativa L.) 11. Molecular cloning and expression of alfalfa isoflavone reductase, a key enzyme of isoflavonoid phytoalexin biosynthesis. Plant molecular biology. 1991 Oct; 17(4):653-67. doi: 10.1007/bf00037051. [PMID: 1912490]
  • D K Miller, S Sadowski, G Q Han, H Joshua. Identification and isolation of medicarpin and a substituted benzofuran as potent leukotriene inhibitors in an anti-inflammatory Chinese herb. Prostaglandins, leukotrienes, and essential fatty acids. 1989 Nov; 38(2):137-43. doi: 10.1016/0952-3278(89)90098-7. [PMID: 2559412]
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  • . . . . doi: . [PMID: 8071365]
  • . . . . doi: . [PMID: 11006341]
  • . . . . doi: . [PMID: 18055588]
  • . . . . doi: . [PMID: 7805842]
  • . . . . doi: . [PMID: 7625843]