Legumelin (BioDeep_00000002571)

 

Secondary id: BioDeep_00000230126

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one

化学式: C23H22O6 (394.1416312)
中文名称: (-)-鱼藤素, 魚藤素
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 1.81%

分子结构信息

SMILES: C12OC(C)(C)C=CC1=C1O[C@]3([H])COC4C=C(OC)C(OC)=CC=4[C@]3([H])C(=O)C1=CC=2
InChI: InChI=1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3

描述信息

Legumelin, also known as (-)-cis-deguelin, is a member of the class of compounds known as rotenones. Rotenones are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, legumelin is considered to be a flavonoid lipid molecule. Legumelin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Legumelin can be found in soy bean, which makes legumelin a potential biomarker for the consumption of this food product.
Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB.
Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB.
Deguelin, a naturally occurring rotenoid, acts as a chemopreventive agent by blocking multiple pathways like PI3K-Akt, IKK-NF-κB, and MAPK-mTOR-survivin-mediated apoptosis. Deguelin binding to Hsp90 leads to a decreased expression of numerous oncogenic proteins, including MEK1/2, Akt, HIF1α, COX-2, and NF-κB.

同义名列表

7 个代谢物同义名

(1S,14S)-17,18-dimethoxy-7,7-dimethyl-2,8,21-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁵,²⁰]docosa-3(12),4(9),5,10,15,17,19-heptaen-13-one; 13,13a-dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis(1)benzopyrano(3,4-b:6,5-e)pyran-7(7aH)-one; (-)-Deguelin;(-)-cis-Deguelin; (-)-cis-deguelin; Legumelin; Deguelin; (-)-Deguelin



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

35 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

  • Peiwen Zhang, Mengzi Zhang, Terri A Mellich, Brian J Pearson, Jianjun Chen, Zhixiang Zhang. Variation in Rotenone and Deguelin Contents among Strains across Four Tephrosia Species and Their Activities against Aphids and Whiteflies. Toxins. 2022 05; 14(5):. doi: 10.3390/toxins14050339. [PMID: 35622585]
  • Hardeep Singh Tuli, Sonam Mittal, Mariam Loka, Vaishali Aggarwal, Diwakar Aggarwal, Akshara Masurkar, Ginpreet Kaur, Mehmet Varol, Katrin Sak, Manoj Kumar, Gautam Sethi, Anupam Bishayee. Deguelin targets multiple oncogenic signaling pathways to combat human malignancies. Pharmacological research. 2021 04; 166(?):105487. doi: 10.1016/j.phrs.2021.105487. [PMID: 33581287]
  • Aziza H Said, Anita Solhaug, Morten Sandvik, Flower E Msuya, Margareth S Kyewalyanga, Aviti J Mmochi, Jan L Lyche, Selma Hurem. Isolation of the Tephrosia vogelii extract and rotenoids and their toxicity in the RTgill-W1 trout cell line and in zebrafish embryos. Toxicon : official journal of the International Society on Toxinology. 2020 Aug; 183(?):51-60. doi: 10.1016/j.toxicon.2020.05.013. [PMID: 32454059]
  • Weibo Liao, Xin Liu, Quanlue Yang, Huifang Liu, Bingyu Liang, Junjun Jiang, Jiegang Huang, Chuanyi Ning, Ning Zang, Bo Zhou, Yanyan Liao, Jingzhao Chen, Li Tian, Wenzhe Ho, Abu S Abdullah, Lingbao Kong, Hao Liang, Hui Chen, Li Ye. Deguelin inhibits HCV replication through suppressing cellular autophagy via down regulation of Beclin1 expression in human hepatoma cells. Antiviral research. 2020 02; 174(?):104704. doi: 10.1016/j.antiviral.2020.104704. [PMID: 31917237]
  • Yanbei Tu, Chuanhai Wu, Yunyao Kang, Qin Li, Chao Zhu, Yanfang Li. Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa. Bioorganic & medicinal chemistry letters. 2019 05; 29(10):1194-1198. doi: 10.1016/j.bmcl.2019.03.024. [PMID: 30910460]
  • Tan Zhang, Kangxian Zhao, Weiqi Han, Wanlei Yang, Xuanyuan Lu, Qian Liu, Xiucheng Li, Yu Qian. Deguelin inhibits RANKL-induced osteoclastogenesis in vitro and prevents inflammation-mediated bone loss in vivo. Journal of cellular physiology. 2019 03; 234(3):2719-2729. doi: 10.1002/jcp.27087. [PMID: 30078209]
  • Wei Zeng, Wei Qi, Jiao Mu, Yi Wei, Li-Ling Yang, Qian Zhang, Qiong Wu, Jian-Ying Tang, Bing Feng. MG132 protects against renal dysfunction by regulating Akt-mediated inflammation in diabetic nephropathy. Scientific reports. 2019 02; 9(1):2049. doi: 10.1038/s41598-018-38425-2. [PMID: 30765727]
  • Mehmet A Kocdor, Hakan Cengiz, Halil Ates, Hilal Kocdor. Inhibition of Cancer Stem-Like Phenotype by Curcumin and Deguelin in CAL-62 Anaplastic Thyroid Cancer Cells. Anti-cancer agents in medicinal chemistry. 2019; 19(15):1887-1898. doi: 10.2174/1871520619666191004144025. [PMID: 31584382]
  • Ji Chen, Wenjie Liu, Han Yi, Xiaoling Hu, Liangyu Peng, Fengrui Yang. The Natural Rotenoid Deguelin Ameliorates Diabetic Neuropathy by Decreasing Oxidative Stress and Plasma Glucose Levels in Rats via the Nrf2 Signalling Pathway. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 48(3):1164-1176. doi: 10.1159/000491983. [PMID: 30045011]
  • Yung-Ting Hsiao, Ming-Jen Fan, An-Cheng Huang, Jin-Cherng Lien, Jen-Jyh Lin, Jaw-Chyun Chen, Te-Chun Hsia, Rick Sai-Chuen Wu, Jing-Gung Chung. Deguelin Impairs Cell Adhesion, Migration and Invasion of Human Lung Cancer Cells through the NF-[Formula: see text]B Signaling Pathways. The American journal of Chinese medicine. 2018; 46(1):209-229. doi: 10.1142/s0192415x1850012x. [PMID: 29402127]
  • Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy. Journal of natural products. 2017 10; 80(10):2602-2608. doi: 10.1021/acs.jnatprod.6b01052. [PMID: 29043803]
  • Sarah Preston, Pasi K Korhonen, Laurent Mouchiroud, Matteo Cornaglia, Sean L McGee, Neil D Young, Rohan A Davis, Simon Crawford, Cameron Nowell, Brendan R E Ansell, Gillian M Fisher, Katherine T Andrews, Bill C H Chang, Martin A M Gijs, Paul W Sternberg, Johan Auwerx, Jonathan Baell, Andreas Hofmann, Abdul Jabbar, Robin B Gasser. Deguelin exerts potent nematocidal activity via the mitochondrial respiratory chain. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2017 10; 31(10):4515-4532. doi: 10.1096/fj.201700288r. [PMID: 28687609]
  • H M P Dilrukshi Herath, Sarah Preston, Andreas Hofmann, Rohan A Davis, Anson V Koehler, Bill C H Chang, Abdul Jabbar, Robin B Gasser. Screening of a small, well-curated natural product-based library identifies two rotenoids with potent nematocidal activity against Haemonchus contortus. Veterinary parasitology. 2017 Sep; 244(?):172-175. doi: 10.1016/j.vetpar.2017.07.005. [PMID: 28917310]
  • Xia Zhang, Zichu Zhao, Sha Yi, Lu Wen, Jing He, Jingyu Hu, Jun Ruan, Jun Fang, Yan Chen. Deguelin induced differentiation of mutated NPM1 acute myeloid leukemia in vivo and in vitro. Anti-cancer drugs. 2017 08; 28(7):723-738. doi: 10.1097/cad.0000000000000494. [PMID: 28471807]
  • Rini Muharini, Adriana Díaz, Weaam Ebrahim, Attila Mándi, Tibor Kurtán, Nidja Rehberg, Rainer Kalscheuer, Rudolf Hartmann, Raha S Orfali, Wenhan Lin, Zhen Liu, Peter Proksch. Antibacterial and Cytotoxic Phenolic Metabolites from the Fruits of Amorpha fruticosa. Journal of natural products. 2017 01; 80(1):169-180. doi: 10.1021/acs.jnatprod.6b00809. [PMID: 28075580]
  • Yuh Baba, Toyonobu Maeda, Atsuko Suzuki, Satoshi Takada, Masato Fujii, Yasumasa Kato. Deguelin Potentiates Apoptotic Activity of an EGFR Tyrosine Kinase Inhibitor (AG1478) in PIK3CA-Mutated Head and Neck Squamous Cell Carcinoma. International journal of molecular sciences. 2017 Jan; 18(2):. doi: 10.3390/ijms18020262. [PMID: 28134774]
  • Zhang Bao, Pei Zhang, Yinan Yao, Guohua Lu, Zhongkai Tong, Bing Yan, Lingfang Tu, Guangdie Yang, Jianying Zhou. Deguelin Attenuates Allergic Airway Inflammation via Inhibition of NF-κb Pathway in Mice. International journal of biological sciences. 2017; 13(4):492-504. doi: 10.7150/ijbs.17238. [PMID: 28529457]
  • 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]
  • Danielle da Costa, Consuelo E Silva, Aline Pinheiro, Débora Frommenwiler, Mara Arruda, Giselle Guilhon, Cláudio Alves, Alberto Arruda, Milton Da Silva. Using LC and Hierarchical Cluster Analysis as Tools to Distinguish Timbó Collections into Two Deguelia Species: A Contribution to Chemotaxonomy. Molecules (Basel, Switzerland). 2016 Apr; 21(5):. doi: 10.3390/molecules21050569. [PMID: 27144548]
  • Curtis J Henrich, Laura K Cartner, Jennifer A Wilson, Richard W Fuller, Anthony E Rizzo, Karlyne M Reilly, James B McMahon, Kirk R Gustafson. Deguelins, Natural Product Modulators of NF1-Defective Astrocytoma Cell Growth Identified by High-Throughput Screening of Partially Purified Natural Product Extracts. Journal of natural products. 2015 Nov; 78(11):2776-81. doi: 10.1021/acs.jnatprod.5b00753. [PMID: 26467198]
  • Sha Yi, Lu Wen, Jing He, Youping Wang, Fei Zhao, Jie Zhao, Zichu Zhao, Guohui Cui, Yan Chen. Deguelin, a selective silencer of the NPM1 mutant, potentiates apoptosis and induces differentiation in AML cells carrying the NPM1 mutation. Annals of hematology. 2015 Feb; 94(2):201-10. doi: 10.1007/s00277-014-2206-x. [PMID: 25242579]
  • Yuh Baba, Masato Fujii, Toyonobu Maeda, Atsuko Suzuki, Satoshi Yuzawa, Yasumasa Kato. Deguelin induces apoptosis by targeting both EGFR-Akt and IGF1R-Akt pathways in head and neck squamous cell cancer cell lines. BioMed research international. 2015; 2015(?):657179. doi: 10.1155/2015/657179. [PMID: 26075254]
  • Haoyu Ye, Caifeng Xie, Wenshuang Wu, Minli Xiang, Zhuowei Liu, Yanfang Li, Minghai Tang, Shucai Li, Jianhong Yang, Huan Tang, Kai Chen, Chaofeng Long, Aihua Peng, Lijuan Chen. Millettia pachycarpa exhibits anti-inflammatory activity through the suppression of LPS-induced NO/iNOS expression. The American journal of Chinese medicine. 2014; 42(4):949-65. doi: 10.1142/s0192415x14500608. [PMID: 25004885]
  • Julie A Vrana, Nathan Boggs, Holly N Currie, Jonathan Boyd. Amelioration of an undesired action of deguelin. Toxicon : official journal of the International Society on Toxinology. 2013 Nov; 74(?):83-91. doi: 10.1016/j.toxicon.2013.07.028. [PMID: 23933198]
  • Mei-ling Bai, Hai-jun Li, Lin-xi Zhang. [Effects of deguelin on the proliferation and apoptosis of human esophageal cancer cell Ec-109: an experimental research]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2013 Mar; 33(3):397-400. doi: . [PMID: 23713258]
  • Rajeshwari Mehta, Harshadadevi Katta, Fatouma Alimirah, Rutulkumar Patel, Genoveva Murillo, Xinjian Peng, Miguel Muzzio, Rajendra G Mehta. Deguelin action involves c-Met and EGFR signaling pathways in triple negative breast cancer cells. PloS one. 2013; 8(6):e65113. doi: 10.1371/journal.pone.0065113. [PMID: 23762292]
  • M K Kalume, B Losson, L Angenot, M Tits, J N Wauters, M Frédérich, C Saegerman. Rotenoid content and in vitro acaricidal activity of Tephrosia vogelii leaf extract on the tick Rhipicephalus appendiculatus. Veterinary parasitology. 2012 Nov; 190(1-2):204-9. doi: 10.1016/j.vetpar.2012.06.015. [PMID: 22795670]
  • Steven R Belmain, Barbara A Amoah, Stephen P Nyirenda, John F Kamanula, Philip C Stevenson. Highly variable insect control efficacy of Tephrosia vogelii chemotypes. Journal of agricultural and food chemistry. 2012 Oct; 60(40):10055-63. doi: 10.1021/jf3032217. [PMID: 22970736]
  • John E Casida. The greening of pesticide-environment interactions: some personal observations. Environmental health perspectives. 2012 Apr; 120(4):487-93. doi: 10.1289/ehp.1104405. [PMID: 22472325]
  • Cheng Jiang, Shengzi Liu, Weihong He, Xiongming Luo, Si Zhang, Zhihui Xiao, Ximin Qiu, Hao Yin. A new prenylated flavanone from Derris trifoliata Lour. Molecules (Basel, Switzerland). 2012 Jan; 17(1):657-63. doi: 10.3390/molecules17010657. [PMID: 22237680]
  • Gabriele Multhoff, Jürgen Radons. Radiation, inflammation, and immune responses in cancer. Frontiers in oncology. 2012; 2(?):58. doi: 10.3389/fonc.2012.00058. [PMID: 22675673]
  • Hyunseung Lee, Ju-Hee Lee, Kyung Hee Jung, Soon-Sun Hong. Deguelin promotes apoptosis and inhibits angiogenesis of gastric cancer. Oncology reports. 2010 Oct; 24(4):957-63. doi: 10.3892/or.2010.957. [PMID: 20811676]
  • Wei Ji, Yulan Cui, Renjuan Chen, Xinren Lin, Qingxin Zhou, Chunji Gan. [Separation and preparation of two rotenoids from the roots of Derris by high-speed counter-current chromatography]. Se pu = Chinese journal of chromatography. 2010 Aug; 28(8):813-6. doi: 10.3724/sp.j.1123.2010.00813. [PMID: 21261054]
  • Ville Härmä, Johannes Virtanen, Rami Mäkelä, Antti Happonen, John-Patrick Mpindi, Matias Knuuttila, Pekka Kohonen, Jyrki Lötjönen, Olli Kallioniemi, Matthias Nees. A comprehensive panel of three-dimensional models for studies of prostate cancer growth, invasion and drug responses. PloS one. 2010 May; 5(5):e10431. doi: 10.1371/journal.pone.0010431. [PMID: 20454659]
  • Kwangmi Kim, Lin Wang, Inkyu Hwang. Acute inhibition of selected membrane-proximal mouse T cell receptor signaling by mitochondrial antagonists. PloS one. 2009 Nov; 4(11):e7738. doi: 10.1371/journal.pone.0007738. [PMID: 19901985]
  • Genoveva Murillo, Xinjian Peng, Karen E O Torres, Rajendra G Mehta. Deguelin inhibits growth of breast cancer cells by modulating the expression of key members of the Wnt signaling pathway. Cancer prevention research (Philadelphia, Pa.). 2009 Nov; 2(11):942-50. doi: 10.1158/1940-6207.capr-08-0232. [PMID: 19861542]
  • Supinya Tewtrakul, Sarot Cheenpracha, Chatchanok Karalai. Nitric oxide inhibitory principles from Derris trifoliata stems. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2009 Jun; 16(6-7):568-72. doi: 10.1016/j.phymed.2008.12.015. [PMID: 19303755]
  • Nguyen Tien Dat, Jeong-Hyung Lee, Kyeong Lee, Young-Soo Hong, Young Ho Kim, Jung Joon Lee. Phenolic constituents of Amorpha fruticosa that inhibit NF-kappaB activation and related gene expression. Journal of natural products. 2008 Oct; 71(10):1696-700. doi: 10.1021/np800383q. [PMID: 18841906]
  • Tsung-Hsien Chou, Ih-Sheng Chen, Tsong-Long Hwang, Tai-Chi Wang, Tzong-Huei Lee, Lin-Yang Cheng, Ya-Chih Chang, Jui-Ying Cho, Jih-Jung Chen. Phthalides from Pittosporum illicioides var. illicioides with inhibitory activity on superoxide generation and elastase release by neutrophils. Journal of natural products. 2008 Oct; 71(10):1692-5. doi: 10.1021/np8004503. [PMID: 18817445]
  • Ju-Hee Lee, Don-Haeng Lee, Hyun-Seung Lee, Joon-Seok Choi, Kyu-Won Kim, Soon-Sun Hong. Deguelin inhibits human hepatocellular carcinoma by antiangiogenesis and apoptosis. Oncology reports. 2008 Jul; 20(1):129-34. doi: . [PMID: 18575727]
  • Haoyu Ye, Lijuan Chen, Yanfang Li, Aihua Peng, Afu Fu, Hang Song, Minghai Tang, Houding Luo, Youfu Luo, Yongbin Xu, Jianyou Shi, Yuquan Wei. Preparative isolation and purification of three rotenoids and one isoflavone from the seeds of Millettia pachycarpa Benth by high-speed counter-current chromatography. Journal of chromatography. A. 2008 Jan; 1178(1-2):101-7. doi: 10.1016/j.chroma.2007.11.060. [PMID: 18082754]
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  • Raffaella Dell'Eva, Claudia Ambrosini, Simona Minghelli, Douglas M Noonan, Adriana Albini, Nicoletta Ferrari. The Akt inhibitor deguelin, is an angiopreventive agent also acting on the NF-kappaB pathway. Carcinogenesis. 2007 Feb; 28(2):404-13. doi: 10.1093/carcin/bgl162. [PMID: 16952909]
  • Toshio Morikawa, Fengming Xu, Hisashi Matsuda, Masayuki Yoshikawa. Structures of new flavonoids, erycibenins D, E, and F, and NO production inhibitors from Erycibe expansa originating in Thailand. Chemical & pharmaceutical bulletin. 2006 Nov; 54(11):1530-4. doi: 10.1248/cpb.54.1530. [PMID: 17077549]
  • Asha S Nair, Shishir Shishodia, Kwang Seok Ahn, Ajaikumar B Kunnumakkara, Gautam Sethi, Bharat B Aggarwal. Deguelin, an Akt inhibitor, suppresses IkappaBalpha kinase activation leading to suppression of NF-kappaB-regulated gene expression, potentiation of apoptosis, and inhibition of cellular invasion. Journal of immunology (Baltimore, Md. : 1950). 2006 Oct; 177(8):5612-22. doi: 10.4049/jimmunol.177.8.5612. [PMID: 17015749]
  • Ho-Young Lee, Seung-Hyun Oh, Jong K Woo, Woo-Young Kim, Carolyn S Van Pelt, Roger E Price, Dianna Cody, Hai Tran, John M Pezzuto, Robert M Moriarty, Waun Ki Hong. Chemopreventive effects of deguelin, a novel Akt inhibitor, on tobacco-induced lung tumorigenesis. Journal of the National Cancer Institute. 2005 Nov; 97(22):1695-9. doi: 10.1093/jnci/dji377. [PMID: 16288123]
  • J J Gills, J Kosmeder, R C Moon, D D Lantvit, J M Pezzuto. Effect of deguelin on UVB-induced skin carcinogenesis. Journal of chemotherapy (Florence, Italy). 2005 Jun; 17(3):297-301. doi: 10.1179/joc.2005.17.3.297. [PMID: 16041863]
  • Abiy Yenesew, Eluid K Mushibe, Martha Induli, Solomon Derese, J O Midiwo, Jacques M Kabaru, Matthias Heydenreich, Andreas Koch, Martin G Peter. 7a-O-methyldeguelol, a modified rotenoid with an open ring-C, from the roots of Derris trifoliata. Phytochemistry. 2005 Mar; 66(6):653-7. doi: 10.1016/j.phytochem.2005.02.005. [PMID: 15771885]
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  • N Hail, R Lotan. Apoptosis induction by the natural product cancer chemopreventive agent deguelin is mediated through the inhibition of mitochondrial bioenergetics. Apoptosis : an international journal on programmed cell death. 2004 Jul; 9(4):437-47. doi: 10.1023/b:appt.0000031449.57551.e1. [PMID: 15192326]
  • Chihiro Ito, Masataka Itoigawa, Naoki Kojima, Hugh T-W Tan, Junko Takayasu, Harukuni Tokuda, Hoyoku Nishino, Hiroshi Furukawa. Cancer chemopreventive activity of rotenoids from Derris trifoliata. Planta medica. 2004 Jun; 70(6):585-8. doi: 10.1055/s-2004-815447. [PMID: 15229812]
  • Maddalena Cabizza, Alberto Angioni, Marinella Melis, Marco Cabras, Carlo V Tuberoso, Paolo Cabras. Rotenone and rotenoids in cubè resins, formulations, and residues on olives. Journal of agricultural and food chemistry. 2004 Jan; 52(2):288-93. doi: 10.1021/jf034987a. [PMID: 14733510]
  • Chihiro Ito, Masataka Itoigawa, Naoki Kojima, Hugh T-W Tan, Junko Takayasu, Harukuni Tokuda, Hoyoku Nishino, Hiroshi Furukawa. Cancer chemopreventive activity of rotenoids from Derris trifoliata. Planta medica. 2004 Jan; 70(1):8-11. doi: 10.1055/s-2004-815447. [PMID: 14765285]
  • Abiy Yenesew, Solomon Derese, Jacob O Midiwo, Matthias Heydenreich, Martin G Peter. Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti. Pest management science. 2003 Oct; 59(10):1159-61. doi: 10.1002/ps.740. [PMID: 14561074]
  • Kyung-Hee Chun, Jerome W Kosmeder, Shihua Sun, John M Pezzuto, Reuben Lotan, Waun Ki Hong, Ho-Young Lee. Effects of deguelin on the phosphatidylinositol 3-kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells. Journal of the National Cancer Institute. 2003 Feb; 95(4):291-302. doi: 10.1093/jnci/95.4.291. [PMID: 12591985]
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