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 (482.2304)
中文名称: 葛杜宁
谱图信息: 最多检出来源 Viridiplantae(plant) 51.91%

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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 BCL2, CASP3, CASP7, CASP9, EGFR, MTOR, NFE2L2, NLRP3, PIK3CA, PTGES3, TLR4
Peripheral membrane protein 2 ACHE, MTOR
Endosome membrane 2 EGFR, TLR4
Endoplasmic reticulum membrane 5 BCL2, EGFR, HMOX1, HSP90B1, MTOR
Nucleus 12 ACHE, BCL2, CASP3, CASP7, CASP9, EGFR, HMOX1, HSP90B1, MTOR, NFE2L2, NLRP3, PTGES3
autophagosome 1 MAP1LC3A
cytosol 13 AHSA1, BCL2, CASP3, CASP7, CASP9, HMOX1, HSP90B1, MAP1LC3A, MTOR, NFE2L2, NLRP3, PIK3CA, PTGES3
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
centrosome 1 NFE2L2
nucleoplasm 6 CASP3, CASP7, HMOX1, MTOR, NFE2L2, PTGES3
RNA polymerase II transcription regulator complex 1 NFE2L2
Cell membrane 4 ACHE, EGFR, TLR4, TNF
Lipid-anchor 1 MAP1LC3A
Cytoplasmic side 2 HMOX1, MTOR
lamellipodium 1 PIK3CA
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Golgi apparatus membrane 2 MTOR, NLRP3
Synapse 1 ACHE
cell junction 1 EGFR
cell surface 4 ACHE, EGFR, TLR4, TNF
glutamatergic synapse 3 CASP3, EGFR, MAP1LC3A
Golgi apparatus 2 ACHE, NFE2L2
Golgi membrane 3 EGFR, MTOR, NLRP3
lysosomal membrane 1 MTOR
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 4 AHSA1, CASP7, NFE2L2, NLRP3
Lysosome 1 MTOR
endosome 1 EGFR
plasma membrane 6 ACHE, EGFR, NFE2L2, PIK3CA, TLR4, TNF
Membrane 8 ACHE, BCL2, EGFR, HMOX1, HSP90B1, MTOR, NLRP3, TLR4
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
extracellular exosome 3 AHSA1, AMY2A, HSP90B1
Lysosome membrane 1 MTOR
endoplasmic reticulum 5 AHSA1, BCL2, HMOX1, HSP90B1, NLRP3
extracellular space 8 ACHE, AMY2A, CASP7, EGFR, HMOX1, IL10, IL6, TNF
perinuclear region of cytoplasm 6 ACHE, EGFR, HMOX1, HSP90B1, PIK3CA, TLR4
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, CASP9, NLRP3
protein-containing complex 5 BCL2, CASP9, EGFR, HSP90B1, PTGES3
intracellular membrane-bounded organelle 1 MAP1LC3A
Microsome membrane 1 MTOR
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 EGFR, TLR4
Secreted 4 ACHE, IL10, IL6, NLRP3
extracellular region 7 ACHE, AMY2A, HSP90B1, IL10, IL6, NLRP3, TNF
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 3 BCL2, HMOX1, MTOR
Extracellular side 1 ACHE
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, EGFR
external side of plasma membrane 2 TLR4, TNF
midbody 1 HSP90B1
Early endosome 1 TLR4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 EGFR, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 MAP1LC3A
focal adhesion 2 EGFR, HSP90B1
microtubule 1 MAP1LC3A
basement membrane 1 ACHE
intracellular vesicle 1 EGFR
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 HSP90B1
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Cell projection, ruffle 1 TLR4
Late endosome 1 MAP1LC3A
ruffle 1 TLR4
receptor complex 2 EGFR, TLR4
chromatin 1 NFE2L2
mediator complex 1 NFE2L2
Cytoplasmic vesicle, autophagosome membrane 1 MAP1LC3A
autophagosome membrane 1 MAP1LC3A
phagocytic cup 2 TLR4, TNF
Secreted, extracellular space 1 CASP7
chromosome, telomeric region 1 PTGES3
Lipid-anchor, GPI-anchor 1 ACHE
organelle membrane 1 MAP1LC3A
nuclear envelope 1 MTOR
Endomembrane system 3 MAP1LC3A, MTOR, NLRP3
microtubule organizing center 1 NLRP3
Melanosome 1 HSP90B1
side of membrane 1 ACHE
myelin sheath 1 BCL2
sperm plasma membrane 1 HSP90B1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
lipopolysaccharide receptor complex 1 TLR4
endoplasmic reticulum lumen 2 HSP90B1, IL6
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
telomerase holoenzyme complex 1 PTGES3
clathrin-coated endocytic vesicle membrane 1 EGFR
Sarcoplasmic reticulum lumen 1 HSP90B1
protein folding chaperone complex 1 PTGES3
synaptic cleft 1 ACHE
protein-DNA complex 1 NFE2L2
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, phagosome 1 MTOR
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
endocytic vesicle lumen 1 HSP90B1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
Autolysosome 1 MAP1LC3A
interleukin-6 receptor complex 1 IL6
endoplasmic reticulum chaperone complex 1 HSP90B1
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]