Germacranolide (BioDeep_00000227209)
human metabolite
代谢物信息卡片
(3R,3aR,5E,9E,11aS)-3,6,10-Trimethyl-3a,4,7,8,11,11a-hexahydrocyclodeca[b]furan-2(3H)-one
化学式: C15H22O2 (234.1619712)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1=CCC2C(CC(C)=CCC1)OC(=O)C2C
InChI: InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h6-7,12-14H,4-5,8-9H2,1-3H3/b10-7+,11-6+
描述信息
Germacranolides are a group of sesquiterpene lactones. Germacranolide is found in burdock and dandelion.
同义名列表
数据库引用编号
5 个数据库交叉引用编号
- PubChem: 91694425
- HMDB: HMDB0302311
- foodb: FDB004104
- LOTUS: LTS0106982
- wikidata: Q105222830
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- Qian Li, Jia-Qi Niu, Jian-Huan Jia, Wei Xu, Ming Bai, Guo-Dong Yao, Shao-Jiang Song. A highly oxidized germacranolide from elephantopus tomentosus inhibits the growth of hepatocellular carcinoma cells by targeting EGFR in vitro and in vivo.
Bioorganic chemistry.
2024 Feb; 143(?):107007. doi:
10.1016/j.bioorg.2023.107007. [PMID: 38039928] - Jia-Xin Yan, Qi-Hao Li, Tian-Ze Li, Zhi-Yan Huang, Yun-Bao Ma, Ji-Jun Chen. Design and synthesis of guaianolide-germacranolide heterodimers as novel anticancer agents against hepatocellular carcinoma.
Drug development research.
2023 09; 84(6):1285-1298. doi:
10.1002/ddr.22087. [PMID: 37345274] - Ming Bai, Wei Xu, Qian Li, De-Feng Liu, Tian-Ming Lv, Ning-Ning Du, Guo-Dong Yao, Bin Lin, Shao-Jiang Song, Xiao-Xiao Huang. Highly Oxidized Germacranolides from Elephantopus tomentosus and the Configurational Revision of Some Previously Reported Analogues.
Journal of natural products.
2022 10; 85(10):2433-2444. doi:
10.1021/acs.jnatprod.2c00630. [PMID: 36223633] - Weihong Zhong, Min Li, Shan Han, Jie Sun, Lan Cao, Zejing Mu, Xiaolang Du, Yushun Cui, Yulin Feng, Guoyue Zhong. Carpelipines C and D, Two Anti-Inflammatory Germacranolides from the Flowers of Carpesium lipskyi Winkl. (Asteraceae).
Chemistry & biodiversity.
2022 Jul; 19(7):e202200415. doi:
10.1002/cbdv.202200415. [PMID: 35608872] - Yi-Fan Yu, Yue-Qian Li, Ru-Yue Wang, Xu Liu, Wen-Bo Cui, Xiao-Han Chen, Cheng-Mu Zhao, Feng-Ming Qi, Zhan-Xin Zhang, Dong-Qing Fei. A new highly oxygenated germacranolide from Carpesium nepalense var. lanatum (C.B.Clarke) Kitam.
Natural product research.
2022 May; 36(9):2306-2313. doi:
10.1080/14786419.2020.1833199. [PMID: 33089720] - Chen Yan, Qun Long, Yun-Dong Zhang, Gajendran Babu, Madhu Varier Krishnapriya, Jian-Fei Qiu, Jing-Rui Song, Qing Rao, Ping Yi, Mao Sun, Yan-Mei Li. Germacranolide sesquiterpenes from Carpesium cernuum and their anti-leukemia activity.
Chinese journal of natural medicines.
2021 Jul; 19(7):528-535. doi:
10.1016/s1875-5364(21)60052-3. [PMID: 34247776] - Li Zhu, Xiao-Qin Liu, Yao-Lan Lin, Wen-Li Wang, Jian-Guang Luo, Ling-Yi Kong. Cytotoxic Germacranolides from the Whole Plant of Carpesium minus.
Journal of natural products.
2020 11; 83(11):3230-3238. doi:
10.1021/acs.jnatprod.0c00428. [PMID: 33035058] - Federica Pollastro, Annalisa Lopatriello, José F Vouillamoz, Giovanni Appendino, Orazio Taglialatela-Scafati, Martino Forino. Non volatile constituents of the vermouth ingredient Artemisia vallesiaca.
Fitoterapia.
2019 Oct; 138(?):104312. doi:
10.1016/j.fitote.2019.104312. [PMID: 31419464] - Carmina Sirignano, Alì Snene, Alain Rodrigue Tenoh, Ridha El Mokni, Daniela Rigano, Annette Habluetzel, Saoussen Hammami, Orazio Taglialatela-Scafati. Daucovirgolides I-L, four congeners of the antimalarial daucovirgolide G from Daucus virgatus.
Fitoterapia.
2019 Sep; 137(?):104188. doi:
10.1016/j.fitote.2019.104188. [PMID: 31158428] - Sahar Mofidi Tabatabaei, Samad Nejad Ebrahimi, Peyman Salehi, Ali Sonboli, Marzieh Tabefam, Marcel Kaiser, Matthias Hamburger, Mahdi Moridi Farimani. Antiprotozoal Germacranolide Sesquiterpene Lactones from Tanacetum sonbolii.
Planta medica.
2019 Mar; 85(5):424-430. doi:
10.1055/a-0824-1294. [PMID: 30620946] - Dong-Dong Xu, Yuan Yan, Chun-Xiao Jiang, Jing-Jing Liang, Hong-Fang Li, Quan-Xiang Wu, Ying Zhu. Sesquiterpenes and diterpenes with cytotoxic activities from the aerial parts of Carpesium humile.
Fitoterapia.
2018 Jul; 128(?):50-56. doi:
10.1016/j.fitote.2018.04.015. [PMID: 29689329] - Tao Zhang, Jin-Guang Si, Qiu-Bo Zhang, Jia-Huan Chen, Gang Ding, Hong-Wu Zhang, Hong-Mei Jia, Zhong-Mei Zou. Three New Highly Oxygenated Germacranolides from Carpesium Divaricatum and Their Cytotoxic Activity.
Molecules (Basel, Switzerland).
2018 May; 23(5):. doi:
10.3390/molecules23051078. [PMID: 29751555] - Zhi Kai Guo, Bei Wang, Cai Hong Cai, Sheng Zhuo Huang, Jing Zhe Yuan, Wen Li Mei, Hao Fu Dai. Tomenphantadenine, an unprecedented germacranolide-adenine hybrid heterodimer from the medicinal plant Elephantopus tomentosus L.
Fitoterapia.
2018 Mar; 125(?):217-220. doi:
10.1016/j.fitote.2017.11.022. [PMID: 29197542] - Njogu M Kimani, Josphat C Matasyoh, Marcel Kaiser, Reto Brun, Thomas J Schmidt. Antiprotozoal Sesquiterpene Lactones and Other Constituents from Tarchonanthus camphoratus and Schkuhria pinnata.
Journal of natural products.
2018 01; 81(1):124-130. doi:
10.1021/acs.jnatprod.7b00747. [PMID: 29244495] - Jerónimo L Ulloa, Renata Spina, Agustina Casasco, Patricia B Petray, Virginia Martino, Miguel A Sosa, Fernanda M Frank, Liliana V Muschietti. Germacranolide-type sesquiterpene lactones from Smallanthus sonchifolius with promising activity against Leishmania mexicana and Trypanosoma cruzi.
Parasites & vectors.
2017 Nov; 10(1):567. doi:
10.1186/s13071-017-2509-6. [PMID: 29132413] - Carmina Sirignano, Alì Snene, Daniela Rigano, Sofia Tapanelli, Carmen Formisano, Paolo Luciano, Ridha El Mokni, Saoussen Hammami, Alain Rodrigue Tenoh, Annette Habluetzel, Orazio Taglialatela-Scafati. Angeloylated Germacranolides from Daucus virgatus and Their Plasmodium Transmission Blocking Activity.
Journal of natural products.
2017 10; 80(10):2787-2794. doi:
10.1021/acs.jnatprod.7b00603. [PMID: 28976194] - Sergio Ortiz, Kamel Dali-Yahia, Pedro Vasquez-Ocmin, Raphaël Grougnet, Philippe Grellier, Sylvie Michel, Alexandre Maciuk, Sabrina Boutefnouchet. Heme-binding activity of methoxyflavones from Pentzia monodiana Maire (Asteraceae).
Fitoterapia.
2017 Apr; 118(?):1-5. doi:
10.1016/j.fitote.2017.01.012. [PMID: 28167052] - Francesco Molinaro, Chiara Mozzetti Monterumici, Aldo Ferrero, Silvia Tabasso, Michèle Negre. Bioherbicidal activity of a germacranolide sesquiterpene dilactone from Ambrosia artemisiifolia L.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes.
2016 Dec; 51(12):847-852. doi:
10.1080/03601234.2016.1208466. [PMID: 27494298] - Qing-Xin Liu, Yong-Xun Yang, Jian-Ping Zhang, Li-Ping Chen, Yun-Heng Shen, Hui-Liang Li, Wei-Dong Zhang. Isolation, Structure Elucidation, and Absolute Configuration of Highly Oxygenated Germacranolides from Carpesium cernuum.
Journal of natural products.
2016 10; 79(10):2479-2486. doi:
10.1021/acs.jnatprod.6b00315. [PMID: 27668963] - Tao Zhang, Jin-Guang Si, Qiu-Bo Zhang, Gang Ding, Zhong-Mei Zou. New Highly Oxygenated Germacranolides from Carpesium divaricatum and their Cytotoxic Activity.
Scientific reports.
2016 06; 6(?):27237. doi:
10.1038/srep27237. [PMID: 27265755] - Christine Unger, Izabella Kiss, Andrea Vasas, Ildikó Lajter, Nina Kramer, Atanas Georgiev Atanasov, Chi Huu Nguyen, Waranya Chatuphonprasert, Stefan Brenner, Sigurd Krieger, Ruxandra McKinnon, Andrea Peschel, Renate Kain, Philipp Saiko, Thomas Szekeres, Lukas Kenner, Melanie R Hassler, Rene Diaz, Richard Frisch, Verena M Dirsch, Walter Jäger, Rainer de Martin, Valery N Bochkov, Claus M Passreiter, Barbara Peter-Vörösmarty, Robert M Mader, Michael Grusch, Helmut Dolznig, Brigitte Kopp, Istvan Zupko, Judit Hohmann, Georg Krupitza. The germacranolide sesquiterpene lactone neurolenin B of the medicinal plant Neurolaena lobata (L.) R.Br. ex Cass inhibits NPM/ALK-driven cell expansion and NF-κB-driven tumour intravasation.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2015 Aug; 22(9):862-74. doi:
10.1016/j.phymed.2015.06.003. [PMID: 26220634] - G Sánchez-Toranzo, J Zapata-Martínez, C Catalán, M I Bühler. Effect of different types of sesquiterpene lactones on the maturation of Rhinella arenarum oocytes.
Zygote (Cambridge, England).
2015 Jun; 23(3):406-11. doi:
10.1017/s0967199413000695. [PMID: 24522008] - Emilie Destandau, Meryem Alaoui Boukhris, Sandrine Zubrzycki, Mohamed Akssira, Lhoucine El Rhaffari, Claire Elfakir. Centrifugal partition chromatography elution gradient for isolation of sesquiterpene lactones and flavonoids from Anvillea radiata.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2015 Mar; 985(?):29-37. doi:
10.1016/j.jchromb.2015.01.019. [PMID: 25647341] - Zsuzsanna Hajdú, Judit Hohmann, Peter Forgo, Imre Máthé, Judit Molnár, István Zupkó. Antiproliferative activity of Artemisia asiatica extract and its constituents on human tumor cell lines.
Planta medica.
2014 Dec; 80(18):1692-7. doi:
10.1055/s-0034-1383146. [PMID: 25295671] - Xiang-Rong Cheng, Chun-Hui Wang, Pan-Lei Wei, Xu-Feng Zhang, Qi Zeng, Shi-Kai Yan, Hui-Zi Jin, Wei-Dong Zhang. New sesquiterpenic acids from Inula wissmanniana.
Fitoterapia.
2014 Jun; 95(?):139-46. doi:
10.1016/j.fitote.2014.03.013. [PMID: 24685502] - Yoshinori Saito, Tomomi Mukai, Yuko Iwamoto, Makiko Baba, Koji Takiguchi, Yasuko Okamoto, Xun Gong, Takayuki Kawahara, Chiaki Kuroda, Motoo Tori. Germacranolides and their diversity of Eupatorium heterophyllum collected in P. R. China.
Chemical & pharmaceutical bulletin.
2014; 62(11):1092-9. doi:
10.1248/cpb.c14-00426. [PMID: 25212243] - Tanja Milošević Ifantis, Slavica Solujić, Dragana Pavlović-Muratspahić, Helen Skaltsa. Secondary metabolites from the aerial parts of Centaurea pannonica (Heuff.) Simonk. from Serbia and their chemotaxonomic importance.
Phytochemistry.
2013 Oct; 94(?):159-70. doi:
10.1016/j.phytochem.2013.05.014. [PMID: 23827325] - Yuan-Feng Yang, Jie-Qing Liu, Zhong-Rong Li, Yan Li, Ming-Hua Qiu. New eudesmenoic acid methyl esters from the seed oil of Jatropha curcas.
Fitoterapia.
2013 Sep; 89(?):278-84. doi:
10.1016/j.fitote.2013.06.011. [PMID: 23811432] - Jiang-Jiang Qin, Jia-Xian Zhu, Qi Zeng, Xiang-Rong Cheng, Shou-De Zhang, Hui-Zi Jin, Wei-Dong Zhang. Sesquiterpene lactones from Inula hupehensis inhibit nitric oxide production in RAW264.7 macrophages.
Planta medica.
2012 Jun; 78(10):1002-9. doi:
10.1055/s-0031-1298621. [PMID: 22648378] - Hyun Jung Shin, So Young Lee, Ju Sun Kim, Sanghyun Lee, Ran Joo Choi, Ha Sook Chung, Yeong Shik Kim, Sam Sik Kang. Sesquiterpenes and other constituents from Dendranthema zawadskii var. latilobum.
Chemical & pharmaceutical bulletin.
2012; 60(3):306-14. doi:
10.1248/cpb.60.306. [PMID: 22382409] - Bei Wang, Wen-Li Mei, Yan-Bo Zeng, Zhi-Kai Guo, Guo-Dao Liu, Hao-Fu Dai. A new sesquiterpene lactone from Elephantopus tomentosus.
Journal of Asian natural products research.
2012; 14(7):700-3. doi:
10.1080/10286020.2012.682153. [PMID: 22582752] - Akbar Esmaeili, Nasrin Moazami, Abdolhossein Rustaiyan. Biotransformation of germacranolide from Onopordon leptolepies by Aspergillus niger.
Pakistan journal of pharmaceutical sciences.
2012 Jan; 25(1):155-9. doi:
. [PMID: 22186324] - Hankui Wu, Frank R Fronczek, Charles L Burandt, Jordan K Zjawiony. Antileishmanial Germacranolides from Calea zacatechichi.
Planta medica.
2011 May; 77(7):749-53. doi:
10.1055/s-0030-1250584. [PMID: 21128202] - Sergio Rosselli, Antonella Maria Maggio, Rosa Angela Raccuglia, Susan L Morris-Natschke, Kenneth F Bastow, Kuo-Hsiung Lee, Maurizio Bruno. Acid rearrangment of epoxy-germacranolides and absolute configuration of 1beta,10alpha-epoxy-salonitenolide.
Natural product communications.
2010 May; 5(5):675-80. doi:
. [PMID: 20521529] - Hee Wook Park, Jae Hyeok Lee, Sang-Un Choi, Nam-In Baek, Sung-Hoon Kim, Jae Heon Yang, Dae Keun Kim. Cytotoxic germacranolide sesquiterpenes from the bark of Magnolia kobus.
Archives of pharmacal research.
2010 Jan; 33(1):71-4. doi:
10.1007/s12272-010-2227-5. [PMID: 20191346] - Hong-Gang Xie, Hong Chen, Bo Cao, Hong-Wu Zhang, Zhong-Mei Zou. Cytotoxic germacranolide sesquiterpene from Inula cappa.
Chemical & pharmaceutical bulletin.
2007 Aug; 55(8):1258-60. doi:
10.1248/cpb.55.1258. [PMID: 17666855] - Nobuyasu Matsuura, Masashi Yamada, Hiroto Suzuki, Naoko Hasegawa, Chihiro Kurosaka, Makoto Ubukata, Toshiyuki Tanaka, Munekazu Iinuma. Inhibition of preadipocyte differentiation by germacranolides from Calea urticifolia in 3T3-L1 cells.
Bioscience, biotechnology, and biochemistry.
2005 Dec; 69(12):2470-4. doi:
10.1271/bbb.69.2470. [PMID: 16377913] - Yoshihito Nakagawa, Munekazu Iinuma, Nobuyasu Matsuura, Kong Yi, Makoto Naoi, Toshihiro Nakayama, Yoshinori Nozawa, Yukihiro Akao. A potent apoptosis-inducing activity of a sesquiterpene lactone, arucanolide, in HL60 cells: a crucial role of apoptosis-inducing factor.
Journal of pharmacological sciences.
2005 Feb; 97(2):242-52. doi:
10.1254/jphs.fp0040456. [PMID: 15699578] - B El Hassany, F El Hanbali, M Akssira, F Mellouki, A Haidour, A F Barrero. Germacranolides from Anvillea radiata.
Fitoterapia.
2004 Sep; 75(6):573-6. doi:
10.1016/j.fitote.2004.06.003. [PMID: 15351111] - Jan-Willem de Kraker, Maurice C R Franssen, Maaike Joerink, Aede de Groot, Harro J Bouwmeester. Biosynthesis of costunolide, dihydrocostunolide, and leucodin. Demonstration of cytochrome p450-catalyzed formation of the lactone ring present in sesquiterpene lactones of chicory.
Plant physiology.
2002 May; 129(1):257-68. doi:
10.1104/pp.010957. [PMID: 12011356] - P P Pujar, D D Sawaikar, S R Rojatkar, B A Nagasampagi. A new germacranolide from Artemisia pallens.
Fitoterapia.
2000 Sep; 71(5):590-2. doi:
10.1016/s0367-326x(00)00168-4. [PMID: 11449517]