Gedunin (BioDeep_00000271608)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00179126-03_C28H34O7_(6R,6aS,6bR,7aS,10S,10aS,12bR)-10-(3-Furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl acetate

化学式: C28H34O7 (482.2304414)
中文名称: 葛杜宁
谱图信息: 最多检出来源 Viridiplantae(plant) 1.64%

分子结构信息

SMILES: CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C45C(O4)C(=O)OC(C5(CC3)C)C6=COC=C6)C)C)(C)C
InChI: InChI=1S/C28H34O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h8-10,12,14,17-18,20-22H,7,11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1

描述信息

A natural product found in Azadirachta indica.
Gedunin is a pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata. It has a role as an antimalarial, an antineoplastic agent, a Hsp90 inhibitor and a plant metabolite. It is a limonoid, an acetate ester, an epoxide, an enone, a member of furans, a pentacyclic triterpenoid, an organic heteropentacyclic compound and a lactone.
Gedunin is a natural product found in Azadirachta indica, Cedrela odorata, and other organisms with data available.
A pentacyclic triterpenoid natural product found particularly in Azadirachta indica and Cedrela odorata.

同义名列表

14 个代谢物同义名

Gedunin; (6R,6aS,6bR,7aS,10R,10aS,12bR)-10-(furan-3-yl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl acetate; (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-1-(Furan-3-yl)-4b,7,7,10a,12a-pentamethyl-3,8-dioxo-1,3,3a,4b,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate; (4aR,6R,6aS,6bR,7aS,10S,10aS,12aR,12bR)-10-(furan-3-yl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl acetate; (4aR,6R,6aS,6bR,7aS,10R,10aS,12aR,12bR)-10-(3-furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydrooxireno[c]phenanthro[1,2-d]pyran-6-yl acetate; Oxireno(c)phenanthro(1,2-d)pyran-3,8(3aH,4bH)-dione, 5-(acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a-decahydro-4b,7,7,10a,12a-pentamethyl-,(1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-; (1S,3aS,4aR,4bS,5R,6aR,10aR,10bR,12aS)-5-(Acetyloxy)-1-(3-furanyl)-1,5,6,6a,7,10a,10b,11,12,12a,decahydro-4b,7,7,10a,12a,-pentamethyloxireno[c]phenanthro[1,2-d]pyran-3,8(3aH,4bH)-dione; D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,14beta,15beta,17aalpha)-; D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-(5alpha,7alpha,13alpha,14beta,15beta,17aalpha)-; (-)-gedunin; VH4BN8F5Z5; A1-06837; Gedunine; NCGC00179126-03_C28H34O7_(6R,6aS,6bR,7aS,10S,10aS,12bR)-10-(3-Furyl)-4,4,6a,10a,12b-pentamethyl-3,8-dioxo-3,4,4a,5,6,6a,7a,8,10,10a,11,12,12a,12b-tetradecahydronaphtho[2,1-f]oxireno[d]isochromen-6-yl acetate



数据库引用编号

30 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

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)

43 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

  • Siddavaram Nagini, Manikandan Palrasu, Anupam Bishayee. Limonoids from neem (Azadirachta Indica A. Juss.) are potential anticancer drug candidates. Medicinal research reviews. 2023 Aug; ?(?):. doi: 10.1002/med.21988. [PMID: 37589457]
  • Akifumi Nagatomo, Kiyofumi Ninomiya, Shinsuke Marumoto, Chie Sakai, Shuta Watanabe, Wakana Ishikawa, Yoshiaki Manse, Takashi Kikuchi, Takeshi Yamada, Reiko Tanaka, Osamu Muraoka, Toshio Morikawa. A Gedunin-Type Limonoid, 7-Deacetoxy-7-Oxogedunin, from Andiroba (Carapa guianensis Aublet) Reduced Intracellular Triglyceride Content and Enhanced Autophagy in HepG2 Cells. International journal of molecular sciences. 2022 Oct; 23(21):. doi: 10.3390/ijms232113141. [PMID: 36361930]
  • Priya Dagar, Abha Mishra. Molecular modeling and in vitro studies of gedunin a potent alpha-amylase inhibitor and alpha-glucosidase inhibitor. BioFactors (Oxford, England). 2022 Sep; 48(5):1118-1128. doi: 10.1002/biof.1846. [PMID: 35608401]
  • Mary Olufunmilayo Ologe. A novel gedunin-2-hydroxypropyl-β-cyclodextrin inclusion complex improves anti-nociceptive and anti-inflammatory activities of gedunin in rodents. Nigerian journal of physiological sciences : official publication of the Physiological Society of Nigeria. 2022 Jun; 37(1):9-19. doi: 10.54548/njps.v37i1.2. [PMID: 35947833]
  • JianYu Chen, GuoYuan Zhu, YiBin Sun, YueChan Wu, BaoKun Wu, WanTing Zheng, XueQin Ma, YanFang Zheng. 7-deacetyl-gedunin suppresses proliferation of Human rheumatoid arthritis synovial fibroblast through activation of Nrf2/ARE signaling. International immunopharmacology. 2022 Jun; 107(?):108557. doi: 10.1016/j.intimp.2022.108557. [PMID: 35247778]
  • Jian-Yu Chen, Xiao-Yun Tian, Wen-Jing Liu, Bao-Kun Wu, Yue-Chan Wu, Ming-Xing Zhu, Jin-Liu, Xian Zhou, Yan-Fang Zheng, Xue-Qin Ma, Ming-Qing Huang. Importance of Gedunin in Antagonizing Rheumatoid Arthritis via Activating the Nrf2/ARE Signaling. Oxidative medicine and cellular longevity. 2022; 2022(?):6277760. doi: 10.1155/2022/6277760. [PMID: 35432723]
  • Rohit Sahai, Arindam Bhattacharjee, Vishwa Nath Shukla, Pragya Yadav, Mohammad Hasanain, Jayanta Sarkar, T Narender, Kalyan Mitra. Gedunin isolated from the mangrove plant Xylocarpus granatum exerts its anti-proliferative activity in ovarian cancer cells through G2/M-phase arrest and oxidative stress-mediated intrinsic apoptosis. Apoptosis : an international journal on programmed cell death. 2020 08; 25(7-8):481-499. doi: 10.1007/s10495-020-01605-5. [PMID: 32399945]
  • Toshio Morikawa, Akifumi Nagatomo, Kayako Kitazawa, Osamu Muraoka, Takashi Kikuchi, Takeshi Yamada, Reiko Tanaka, Kiyofumi Ninomiya. Collagen Synthesis-Promoting Effects of Andiroba Oil and its Limonoid Constituents in Normal Human Dermal Fibroblasts. Journal of oleo science. 2018; 67(10):1271-1277. doi: 10.5650/jos.ess18143. [PMID: 30305560]
  • Subash Chandra Gupta, Sahdeo Prasad, Amit K Tyagi, Ajaikumar B Kunnumakkara, Bharat B Aggarwal. Neem (Azadirachta indica): An indian traditional panacea with modern molecular basis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Oct; 34(?):14-20. doi: 10.1016/j.phymed.2017.07.001. [PMID: 28899496]
  • Chanin Sarigaputi, Nuanpan Sangpech, Tanapat Palaga, Khanitha Pudhom. Suppression of inducible nitric oxide synthase pathway by 7-deacetylgedunin, a limonoid from Xylocarpus sp. Planta medica. 2015 Mar; 81(4):312-9. doi: 10.1055/s-0034-1396308. [PMID: 25714725]
  • Fernando P Conte, Fausto K Ferraris, Thadeu E M M Costa, Patricia Pacheco, Leonardo N Seito, Waldiceu A Verri, Fernando Q Cunha, Carmen Penido, Maria G Henriques. Effect of gedunin on acute articular inflammation and hypernociception in mice. Molecules (Basel, Switzerland). 2015 Feb; 20(2):2636-57. doi: 10.3390/molecules20022636. [PMID: 25654532]
  • Sudha Ponnusamy, Saikat Haldar, Fayaj Mulani, Smita Zinjarde, Hirekodathakallu Thulasiram, Ameeta RaviKumar. Gedunin and Azadiradione: Human Pancreatic Alpha-Amylase Inhibiting Limonoids from Neem (Azadirachta indica) as Anti-Diabetic Agents. PloS one. 2015; 10(10):e0140113. doi: 10.1371/journal.pone.0140113. [PMID: 26469405]
  • Sweta Misra, Meenakshi Verma, Sunil Kumar Mishra, Shishir Srivastava, Vijai Lakshmi, Shailja Misra-Bhattacharya. Gedunin and photogedunin of Xylocarpus granatum possess antifilarial activity against human lymphatic filarial parasite Brugia malayi in experimental rodent host. Parasitology research. 2011 Nov; 109(5):1351-60. doi: 10.1007/s00436-011-2380-x. [PMID: 21523424]
  • Giuseppina Chianese, Serge R Yerbanga, Leonardo Lucantoni, Annette Habluetzel, Nicoletta Basilico, Donatella Taramelli, Ernesto Fattorusso, Orazio Taglialatela-Scafati. Antiplasmodial triterpenoids from the fruits of neem, Azadirachta indica. Journal of natural products. 2010 Aug; 73(8):1448-52. doi: 10.1021/np100325q. [PMID: 20669933]
  • V Lakshmi, N Singh, S Shrivastva, S K Mishra, P Dharmani, V Mishra, G Palit. Gedunin and photogedunin of Xylocarpus granatum show significant anti-secretory effects and protect the gastric mucosa of peptic ulcer in rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Jul; 17(8-9):569-74. doi: 10.1016/j.phymed.2009.10.016. [PMID: 19962286]
  • Siddharth G Kamath, Ning Chen, Yin Xiong, Robert Wenham, Sachin Apte, Marcia Humphrey, Janiel Cragun, Johnathan M Lancaster. Gedunin, a novel natural substance, inhibits ovarian cancer cell proliferation. International journal of gynecological cancer : official journal of the International Gynecological Cancer Society. 2009 Dec; 19(9):1564-9. doi: 10.1111/igc.0b013e3181a83135. [PMID: 19955938]
  • Hallur Gurulingappa, Vrushali Tare, Pushpa Pawar, Vijay Tungikar, Yogesh R Jorapur, Sriram Madhavi, Sujata V Bhat. Susceptibility of Aedes aegypti and Culex quinquefasciatus Larvae to gedunin-related limonoids. Chemistry & biodiversity. 2009 Jun; 6(6):897-902. doi: 10.1002/cbdv.200800105. [PMID: 19551731]
  • Andreia P Matos, Ana C Leite, Luciane G Batista-Pereira, Paulo C Vieira, Josäo B Fernandes, Maria Fátima das G F da Silva. Effects of limonoids from Cipadessa fruticosa on fall armyworm. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 May; 64(5-6):441-6. doi: 10.1515/znc-2009-5-623. [PMID: 19678552]
  • Heather A Hostetler, Lindsay R Syler, Lindy N Hall, Guan Zhu, Friedhelm Schroeder, Ann B Kier. A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions. Journal of biomolecular screening. 2008 Oct; 13(9):855-61. doi: 10.1177/1087057108323127. [PMID: 18812576]
  • Carlos L Céspedes, J Rodrigo Salazar, Mariano Martínez, Eduardo Aranda. Insect growth regulatory effects of some extracts and sterols from Myrtillocactus geometrizans (Cactaceae) against Spodoptera frugiperda and Tenebrio molitor. Phytochemistry. 2005 Oct; 66(20):2481-93. doi: 10.1016/j.phytochem.2005.07.010. [PMID: 16122768]
  • Patricio Torres, J Guillermo Avila, Alfonso Romo de Vivar, Ana M García, Juan C Marín, Eduardo Aranda, Carlos L Céspedes. Antioxidant and insect growth regulatory activities of stilbenes and extracts from Yucca periculosa. Phytochemistry. 2003 Sep; 64(2):463-73. doi: 10.1016/s0031-9422(03)00348-0. [PMID: 12943764]
  • J Bickii, N Njifutie, J A Foyere, L K Basco, P Ringwald. In vitro antimalarial activity of limonoids from Khaya grandifoliola C.D.C. (Meliaceae). Journal of ethnopharmacology. 2000 Jan; 69(1):27-33. doi: 10.1016/s0378-8741(99)00117-8. [PMID: 10661881]
  • S MacKinnon, T Durst, J T Arnason, C Angerhofer, J Pezzuto, P E Sanchez-Vindas, L J Poveda, M Gbeassor. Antimalarial activity of tropical Meliaceae extracts and gedunin derivatives. Journal of natural products. 1997 Apr; 60(4):336-41. doi: 10.1021/np9605394. [PMID: 9134742]