Rocaglamide (BioDeep_00000395717)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


1H-Cyclopenta[b]benzofuran-2-carboxamide,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy- 3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, [1R-(1.alpha.,2.alpha.,3.beta.,3a.beta.,8b.beta.)]-

化学式: C29H31NO7 (505.2100416)
中文名称: 楝酰胺
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 2.83%

分子结构信息

SMILES: CN(C)C(=O)C1C(C2(C(C1O)(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5
InChI: InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1

描述信息

Rocaglamide is an organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity. It has a role as a metabolite, an antineoplastic agent and an antileishmanial agent. It is an organic heterotricyclic compound, a monomethoxybenzene and a monocarboxylic acid amide.
Rocaglamide, also referred to as rocaglamide-A, is the eponymous member of a class of anti-cancer phytochemicals known as rocaglamides. Rocaglamides are secondary metabolites of the plant genus Aglaia, and extracts of the plant have traditionally been used as a form of insect repellant due to its natural insecticidal properties. Reports of Aglaia anti-tumor activity date back as far as 1973, and rocaglamide-A was first isolated in 1982 from the species A. elliptifolia. Rocaglamide and a number of its derivatives (e.g. [didesmethylrocaglamide]) are currently being studied for use as chemotherapeutic agents in the treatment of various leukemias, lymphomas, and carcinomas, as well as adjuvant therapy in the treatment of certain chemotherapy-resistant cancers.
Rocaglamide is a natural product found in Aglaia rimosa, Aglaia elliptifolia, and other organisms with data available.
An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity.

同义名列表

19 个代谢物同义名

1H-Cyclopenta[b]benzofuran-2-carboxamide,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy- 3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, [1R-(1.alpha.,2.alpha.,3.beta.,3a.beta.,8b.beta.)]-; (-)-(1alpha,2alpha,3beta,3abeta,8bbeta)-2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta(b)benzofuran-2-carboxamide; 1H-Cyclopenta[b]benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-; 1H-Cyclopenta(b)benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-; (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-2-carboxamide; 1H-Cyclopenta[b]benzofuran-2-carboxamide,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy- 3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-,(1R,2R,3S,3aR,8bS)-; (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide; (1R,2R,3S,3aR,8bS)-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-1,8b-bis(oxidanyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide; (1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide; ROCAGLAMIDE (FR AGLAIA ELLIPTIFOLIA); Rocaglamide; Rocaglamide A; (-)-ROCAGLAMIDE; rocaglamide A; NCI60_002832; Rocaglamide; FRG4N852F7; C29H31NO7; Roc-A; RCG



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

32 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

  • Lorenzo Pedroni, Luca Dellafiora, Maria Olga Varrà, Gianni Galaverna, Sergio Ghidini. In silico study on the Hepatitis E virus RNA Helicase and its inhibition by silvestrol, rocaglamide and other flavagline compounds. Scientific reports. 2022 09; 12(1):15512. doi: 10.1038/s41598-022-19818-w. [PMID: 36109625]
  • Yoon-Su Ha, Taek-Kyong Kim, Ki-Sun Park, Seonghwan Hwang, Jeongkyu Kim, Seung-Jin Kim. Inhibitory effects of Rocaglamide-A on PPARγ-driven adipogenesis through regulation of mitotic clonal expansion involving the JAK2/STAT3 pathway. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2022 06; 1867(6):159148. doi: 10.1016/j.bbalip.2022.159148. [PMID: 35248800]
  • Xuewei Yan, Chao Yao, Cheng Fang, Min Han, Chenyuan Gong, Dan Hu, Weiming Shen, Lixin Wang, Suyun Li, Shiguo Zhu. Rocaglamide promotes the infiltration and antitumor immunity of NK cells by activating cGAS-STING signaling in non-small cell lung cancer. International journal of biological sciences. 2022; 18(2):585-598. doi: 10.7150/ijbs.65019. [PMID: 35002511]
  • J J David Ho, Tyler A Cunningham, Paola Manara, Caroline A Coughlin, Artavazd Arumov, Evan R Roberts, Ashanti Osteen, Preet Kumar, Daniel Bilbao, Jonathan R Krieger, Stephen Lee, Jonathan H Schatz. Proteomics reveal cap-dependent translation inhibitors remodel the translation machinery and translatome. Cell reports. 2021 10; 37(2):109806. doi: 10.1016/j.celrep.2021.109806. [PMID: 34644561]
  • Mingming Chen, Miwako Asanuma, Mari Takahashi, Yuichi Shichino, Mari Mito, Koichi Fujiwara, Hironori Saito, Stephen N Floor, Nicholas T Ingolia, Mikiko Sodeoka, Kosuke Dodo, Takuhiro Ito, Shintaro Iwasaki. Dual targeting of DDX3 and eIF4A by the translation inhibitor rocaglamide A. Cell chemical biology. 2021 04; 28(4):475-486.e8. doi: 10.1016/j.chembiol.2020.11.008. [PMID: 33296667]
  • Canan G Nebigil, Christiane Moog, Stéphan Vagner, Nadia Benkirane-Jessel, Duncan R Smith, Laurent Désaubry. Flavaglines as natural products targeting eIF4A and prohibitins: From traditional Chinese medicine to antiviral activity against coronaviruses. European journal of medicinal chemistry. 2020 Oct; 203(?):112653. doi: 10.1016/j.ejmech.2020.112653. [PMID: 32693294]
  • Shintaro Iwasaki, Wakana Iwasaki, Mari Takahashi, Ayako Sakamoto, Chiduru Watanabe, Yuichi Shichino, Stephen N Floor, Koichi Fujiwara, Mari Mito, Kosuke Dodo, Mikiko Sodeoka, Hiroaki Imataka, Teruki Honma, Kaori Fukuzawa, Takuhiro Ito, Nicholas T Ingolia. The Translation Inhibitor Rocaglamide Targets a Bimolecular Cavity between eIF4A and Polypurine RNA. Molecular cell. 2019 02; 73(4):738-748.e9. doi: 10.1016/j.molcel.2018.11.026. [PMID: 30595437]
  • Ancy D Nalli, Lauren E Brown, Cheryl L Thomas, Thomas J Sayers, John A Porco, Curtis J Henrich. Sensitization of renal carcinoma cells to TRAIL-induced apoptosis by rocaglamide and analogs. Scientific reports. 2018 11; 8(1):17519. doi: 10.1038/s41598-018-35908-0. [PMID: 30504817]
  • Yulin Ren, Gerardo D Anaya-Eugenio, Austin A Czarnecki, Tran Ngoc Ninh, Chunhua Yuan, Hee-Byung Chai, Djaja D Soejarto, Joanna E Burdette, Esperanza J Carcache de Blanco, A Douglas Kinghorn. Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives. Bioorganic & medicinal chemistry. 2018 08; 26(15):4452-4460. doi: 10.1016/j.bmc.2018.07.025. [PMID: 30057155]
  • Chao Yao, Zhongya Ni, Chenyuan Gong, Xiaowen Zhu, Lixin Wang, Zihang Xu, Chunxian Zhou, Suyun Li, Wuxiong Zhou, Chunpu Zou, Shiguo Zhu. Rocaglamide enhances NK cell-mediated killing of non-small cell lung cancer cells by inhibiting autophagy. Autophagy. 2018; 14(10):1831-1844. doi: 10.1080/15548627.2018.1489946. [PMID: 29969944]
  • H Yurugi, F Marini, C Weber, K David, Q Zhao, H Binder, L Désaubry, K Rajalingam. Targeting prohibitins with chemical ligands inhibits KRAS-mediated lung tumours. Oncogene. 2017 08; 36(33):4778-4789. doi: 10.1038/onc.2017.93. [PMID: 28414306]
  • Wei-Hua Jiao, Guo-Hua Shi, Ting-Ting Xu, Guo-Dong Chen, Bin-Bin Gu, Zhuo Wang, Shuang Peng, Shu-Ping Wang, Jia Li, Bing-Nan Han, Wei Zhang, Hou-Wen Lin. Dysiherbols A-C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge. Journal of natural products. 2016 Feb; 79(2):406-11. doi: 10.1021/acs.jnatprod.5b01079. [PMID: 26863083]
  • Shufeng Liu, Wenyu Wang, Lauren E Brown, Chao Qiu, Neil Lajkiewicz, Ting Zhao, Jianhua Zhou, John A Porco, Tony T Wang. A Novel Class of Small Molecule Compounds that Inhibit Hepatitis C Virus Infection by Targeting the Prohibitin-CRaf Pathway. EBioMedicine. 2015 Nov; 2(11):1600-6. doi: 10.1016/j.ebiom.2015.09.018. [PMID: 26870784]
  • Aiguo Li, Libin Yang, Xiaolin Geng, Xingmei Peng, Tan Lu, Yanjun Deng, Yuzheng Dong. Rocaglamide-A Potentiates Osteoblast Differentiation by Inhibiting NF-κB Signaling. Molecules and cells. 2015 Nov; 38(11):941-9. doi: 10.14348/molcells.2015.2353. [PMID: 26549505]
  • Ngoc Tu Duong, RuAngelie Edrada-Ebel, Rainer Ebel, Wenhan Lin, Anh Tuan Duong, Xuan Quy Dang, Ngoc Hieu Nguyen, Peter Proksch. New rocaglamide derivatives from Vietnamese Aglaia species. Natural product communications. 2014 Jun; 9(6):833-4. doi: ". [PMID: 25115092]
  • Jennifer Neumann, Melanie Boerries, Rebecca Köhler, Marco Giaisi, Peter H Krammer, Hauke Busch, Min Li-Weber. The natural anticancer compound rocaglamide selectively inhibits the G1-S-phase transition in cancer cells through the ATM/ATR-mediated Chk1/2 cell cycle checkpoints. International journal of cancer. 2014 Apr; 134(8):1991-2002. doi: 10.1002/ijc.28521. [PMID: 24150948]
  • M S Becker, P Schmezer, R Breuer, S F Haas, M A Essers, P H Krammer, M Li-Weber. The traditional Chinese medical compound Rocaglamide protects nonmalignant primary cells from DNA damage-induced toxicity by inhibition of p53 expression. Cell death & disease. 2014 Jan; 5(?):e1000. doi: 10.1038/cddis.2013.528. [PMID: 24434508]
  • Yulin Ren, Susan Matthew, Daniel D Lantvit, Tran Ngoc Ninh, Heebyung Chai, James R Fuchs, Djaja D Soejarto, Esperanza J Carcache de Blanco, Steven M Swanson, A Douglas Kinghorn. Cytotoxic and NF-κB inhibitory constituents of the stems of Cratoxylum cochinchinense and their semisynthetic analogues. Journal of natural products. 2011 May; 74(5):1117-25. doi: 10.1021/np200051j. [PMID: 21428375]
  • Yulin Ren, Leonardus B S Kardono, Soedarsono Riswan, Heebyung Chai, Norman R Farnsworth, Djaja D Soejarto, Esperanza J Carcache de Blanco, A Douglas Kinghorn. Cytotoxic and NF-kappaB inhibitory constituents of Artocarpus rigida. Journal of natural products. 2010 May; 73(5):949-55. doi: 10.1021/np1002065. [PMID: 20384315]
  • J Y Zhu, M Giaisi, R Köhler, W W Müller, A Mühleisen, P Proksch, P H Krammer, M Li-Weber. Rocaglamide sensitizes leukemic T cells to activation-induced cell death by differential regulation of CD95L and c-FLIP expression. Cell death and differentiation. 2009 Sep; 16(9):1289-99. doi: 10.1038/cdd.2009.42. [PMID: 19373244]
  • Ye Deng, Marcy J Balunas, Jeong-Ah Kim, Daniel D Lantvit, Young-Won Chin, Heebyung Chai, Sugeng Sugiarso, Leonardus B S Kardono, Harry H S Fong, John M Pezzuto, Steven M Swanson, Esperanza J Carcache de Blanco, A Douglas Kinghorn. Bioactive 5,6-dihydro-alpha-pyrone derivatives from Hyptis brevipes. Journal of natural products. 2009 Jun; 72(6):1165-9. doi: 10.1021/np9001724. [PMID: 19422206]
  • Angela A Salim, Alison D Pawlus, Hee-Byung Chai, Norman R Farnsworth, A Douglas Kinghorn, Esperanza J Carcache-Blanco. Ponapensin, a cyclopenta[bc]benzopyran with potent NF-kappaB inhibitory activity from Aglaia ponapensis. Bioorganic & medicinal chemistry letters. 2007 Jan; 17(1):109-12. doi: 10.1016/j.bmcl.2006.09.084. [PMID: 17055270]
  • Soyoung Kim, Angela A Salim, Steven M Swanson, A Douglas Kinghorn. Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy. Anti-cancer agents in medicinal chemistry. 2006 Jul; 6(4):319-45. doi: 10.2174/187152006777698123. [PMID: 16842234]
  • Barbara Hausott, Harald Greger, Brigitte Marian. Flavaglines: a group of efficient growth inhibitors block cell cycle progression and induce apoptosis in colorectal cancer cells. International journal of cancer. 2004 May; 109(6):933-40. doi: 10.1002/ijc.20033. [PMID: 15027128]
  • Gerhard Bringmann, Jörg Mühlbacher, Kim Messer, Michael Dreyer, Rainer Ebel, Bambang W Nugroho, Victor Wray, Peter Proksch. Cyclorocaglamide, the first bridged cyclopentatetrahydrobenzofuran, and a related 'open chain' rocaglamide derivative from Aglaia oligophylla. Journal of natural products. 2003 Jan; 66(1):80-5. doi: 10.1021/np020291k. [PMID: 12542350]
  • Chaidir, W H Lin, R Ebel, R A Edrada, V Wray, M Nimtz, W Sumaryono, P Proksch. Rocaglamides, glycosides, and putrescine bisamides from Aglaia dasyclada. Journal of natural products. 2001 Sep; 64(9):1216-20. doi: 10.1021/np0102354. [PMID: 11575959]
  • D Engelmeier, F Hadacek, T Pacher, S Vajrodaya, H Greger. Cyclopenta[b]benzofurans from Aglaia species with pronounced antifungal activity against rice blast fungus (Pyricularia grisea). Journal of agricultural and food chemistry. 2000 Apr; 48(4):1400-4. doi: 10.1021/jf990509h. [PMID: 10775404]
  • F I Bohnenstengel, K G Steube, C Meyer, B W Nugroho, P D Hung, L C Kiet, P Proksch. Structure activity relationships of antiproliferative rocaglamide derivatives from Aglaia species (Meliaceae). Zeitschrift fur Naturforschung. C, Journal of biosciences. 1999 Jan; 54(1-2):55-60. doi: 10.1515/znc-1999-1-210. [PMID: 10223787]
  • T S Wu, M J Liou, C S Kuoh, C M Teng, T Nagao, K H Lee. Cytotoxic and antiplatelet aggregation principles from Aglaia elliptifolia. Journal of natural products. 1997 Jun; 60(6):606-8. doi: 10.1021/np970163+. [PMID: 9214732]