Erythrodiol (BioDeep_00000000549)

 

Secondary id: BioDeep_00000604176

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol

化学式: C30H50O2 (442.38106)
中文名称: 高根二醇, 赤藓糖醇, 高根二醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.24%

分子结构信息

SMILES: CC1(C)CCC2(CO)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC43C)C2C1
InChI: InChI=1S/C30H50O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,21-24,31-32H,9-19H2,1-7H3/t21-,22-,23+,24-,27-,28+,29+,30+/m0/s1

描述信息

Erythrodiol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Erythrodiol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619, 15522132).
Erythrodiol is a pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a primary alcohol, a secondary alcohol and a diol. It is functionally related to a beta-amyrin.
Erythrodiol is a natural product found in Salacia chinensis, Monteverdia ilicifolia, and other organisms with data available.
See also: Calendula Officinalis Flower (part of); Centaurium erythraea whole (part of).
A pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species.
Found in grapes, olives, pot marigold (Calendula officinalis) and other plants
Erythrodiol is an olive oil component. Erythrodiol promotes Cholesterol efflux (ChE) by selectively inhibiting the degradation of ABCA1 protein. Erythrodiol is a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis[1].
Erythrodiol is an olive oil component. Erythrodiol promotes Cholesterol efflux (ChE) by selectively inhibiting the degradation of ABCA1 protein. Erythrodiol is a good candidate to be further explored for therapeutic or preventive application in the context of atherosclerosis[1].

同义名列表

28 个代谢物同义名

(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol; (3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol; Olean-12-ene-3,28-diol, (3.beta.)-; (3.beta.)-Olean-12-ene-3,28-diol; Erythrodiol, analytical standard; Olean-12-ene-3,28-diol, (3beta)-; 3.BETA.,28-DIHYDROXYOLEAN-12-ENE; (3beta)-Olean-12-ene-3,28-diol; 3beta,28-DIHYDROXYOLEAN-12-ENE; Olean-12-ene-3,28-diol, (3b)-; 3beta,28-dihydroxy-ole-12-ene; Olean-12-ene-3.beta.,28-diol; (3b)-Olean-12-ene-3,28-diol; (3Β)-olean-12-ene-3,28-diol; olean-12-ene-3beta,28-diol; 3Β,28-dihydroxy-ole-12-ene; 3b,28-Dihydroxy-ole-12-ene; 3.BETA.-ERYTHRODIOL; ERYTHRODIOL [INCI]; oleanolic alcohol; 3beta-Erythrodiol; ERYTHRODIOL, (+)-; UNII-3VWF903FSS; 3b-Erythrodiol; 3Β-erythrodiol; Erythrodiol; 3VWF903FSS; Oprea1_748027



数据库引用编号

18 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

5 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

  • oleanolate biosynthesis: O2 + a reduced [NADPH-hemoprotein reductase] + erythrodiol ⟶ H2O + an oxidized [NADPH-hemoprotein reductase] + oleanolic aldehyde

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(4)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

140 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

  • Fiammetta Alagna, James Reed, Ornella Calderini, Ramesha Thimmappa, Nicolò G M Cultrera, Alice Cattivelli, Davide Tagliazucchi, Soraya Mousavi, Roberto Mariotti, Anne Osbourn, Luciana Baldoni. OeBAS and CYP716C67 catalyze the biosynthesis of health-beneficial triterpenoids in olive (Olea europaea L.) fruits. The New phytologist. 2023 Mar; ?(?):. doi: 10.1111/nph.18863. [PMID: 36880371]
  • Santosh Kumar Singh, Shailesh Singh, Rajesh Singh. Targeting novel coronavirus SARS-CoV-2 spike protein with phytoconstituents of Momordica charantia. Journal of ovarian research. 2021 Sep; 14(1):126. doi: 10.1186/s13048-021-00872-3. [PMID: 34579761]
  • Roubi Abuobeid, Luis Herrera-Marcos, María A Navarro, Carmen Arnal, Roberto Martínez-Beamonte, Joaquín Surra, Jesús Osada. Dietary Erythrodiol Modifies Hepatic Transcriptome in Mice in a Sex and Dose-Dependent Way. International journal of molecular sciences. 2020 Oct; 21(19):. doi: 10.3390/ijms21197331. [PMID: 33020388]
  • Pingping Shen, Weiwei Wang, Shaohua Xu, Zhichao Du, Wei Wang, Boyang Yu, Jian Zhang. Biotransformation of Erythrodiol for New Food Supplements with Anti-Inflammatory Properties. Journal of agricultural and food chemistry. 2020 May; 68(21):5910-5916. doi: 10.1021/acs.jafc.0c01420. [PMID: 32351112]
  • 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]
  • Kai Liu, Yue-Hong Qin, Jian-Yong Yu, Heng Ma, Xi-Lin Song. 3-β-Εrythrodiol isolated from Conyza canadensis inhibits MKN‑45 human gastric cancer cell proliferation by inducing apoptosis, cell cycle arrest, DNA fragmentation, ROS generation and reduces tumor weight and volume in mouse xenograft model. Oncology reports. 2016 Apr; 35(4):2328-38. doi: 10.3892/or.2016.4610. [PMID: 26846256]
  • Yao-wu Tao, Ye Tian, Wen-dong Xu, Qing-lan Guo, Jian-gong Shi. [Terpenoids from Euphorbia micractina]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 03; 51(3):411-9. doi: ". [PMID: 29859022]
  • Lamice Habib, Alia Jraij, Nathalie Khreich, Catherine Charcosset, Hélène Greige-Gerges. Effect of Erythrodiol, A Natural Pentacyclic Triterpene from Olive Oil, on the Lipid Membrane Properties. The Journal of membrane biology. 2015 Dec; 248(6):1079-87. doi: 10.1007/s00232-015-9821-x. [PMID: 26141679]
  • Haoxin Li, Stéphanie Jean, Duncan Webster, Gilles A Robichaud, Larry A Calhoun, John A Johnson, Christopher A Gray. Dibenz[b,f]oxepin and Antimycobacterial Chalcone Constituents of Empetrum nigrum. Journal of natural products. 2015 Nov; 78(11):2837-40. doi: 10.1021/acs.jnatprod.5b00627. [PMID: 26473275]
  • Juan José Ramírez-Espinosa, Maria Yolanda Rios, Paolo Paoli, Virginia Flores-Morales, Guido Camici, Vianey de la Rosa-Lugo, Sergio Hidalgo-Figueroa, Gabriel Navarrete-Vázquez, Samuel Estrada-Soto. Synthesis of oleanolic acid derivatives: In vitro, in vivo and in silico studies for PTP-1B inhibition. European journal of medicinal chemistry. 2014 Nov; 87(?):316-27. doi: 10.1016/j.ejmech.2014.09.036. [PMID: 25264584]
  • Brian Mathison, Dirk Holstege. A rapid method to determine sterol, erythrodiol, and uvaol concentrations in olive oil. Journal of agricultural and food chemistry. 2013 May; 61(19):4506-13. doi: 10.1021/jf400254k. [PMID: 23587059]
  • Nguyen X Nhiem, Phan V Kiem, Chau V Minh, Nanyoung Kim, Seonju Park, Hwa Young Lee, Eun Sil Kim, Young Ho Kim, Sohyun Kim, Young-Sang Koh, Seung Hyun Kim. Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Journal of natural products. 2013 Apr; 76(4):495-502. doi: 10.1021/np300490v. [PMID: 23484668]
  • Ghayth Rigane, Mohamed Ayadi, Maher Boukhris, Sami Sayadi, Mohamed Bouaziz. Characterisation and phenolic profiles of two rare olive oils from southern Tunisia: Dhokar and Gemri-Dhokar cultivars. Journal of the science of food and agriculture. 2013 Feb; 93(3):527-34. doi: 10.1002/jsfa.5815. [PMID: 22886385]
  • Anna Szakiel, Cezary Pączkowski, Satu Huttunen. Triterpenoid content of berries and leaves of bilberry Vaccinium myrtillus from Finland and Poland. Journal of agricultural and food chemistry. 2012 Dec; 60(48):11839-49. doi: 10.1021/jf3046895. [PMID: 23157739]
  • Gassan Hodaifa, Leopoldo MartínezNieto, Juan L Lozano, Sebastián Sánchez. Changes of the wax contents in mixtures of olive oils as determined by gas chromatography with a flame ionization detector. Journal of AOAC International. 2012 Nov; 95(6):1720-4. doi: 10.5740/jaoacint.12-011. [PMID: 23451389]
  • R Martín, M Hernández, C Córdova, M L Nieto. Natural triterpenes modulate immune-inflammatory markers of experimental autoimmune encephalomyelitis: therapeutic implications for multiple sclerosis. British journal of pharmacology. 2012 Jul; 166(5):1708-23. doi: 10.1111/j.1476-5381.2012.01869.x. [PMID: 22260389]
  • Maria Carelli, Elisa Biazzi, Francesco Panara, Aldo Tava, Laura Scaramelli, Andrea Porceddu, Neil Graham, Miriam Odoardi, Efisio Piano, Sergio Arcioni, Sean May, Carla Scotti, Ornella Calderini. Medicago truncatula CYP716A12 is a multifunctional oxidase involved in the biosynthesis of hemolytic saponins. The Plant cell. 2011 Aug; 23(8):3070-81. doi: 10.1105/tpc.111.087312. [PMID: 21821776]
  • Wendong Xu, Chenggen Zhu, Wei Cheng, Xiaona Fan, Xiaoguang Chen, Sen Yang, Ying Guo, Fei Ye, Jiangong Shi. Chemical Constituents of the Roots of Euphorbia micractina. Journal of natural products. 2009 Sep; 72(9):1620-6. doi: 10.1021/np900305j. [PMID: 19702283]
  • Rubén Martín, Elvira Ibeas, Juliana Carvalho-Tavares, Marita Hernández, Valentina Ruiz-Gutierrez, María Luisa Nieto. Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation. PloS one. 2009 Jun; 4(6):e5975. doi: 10.1371/journal.pone.0005975. [PMID: 19543395]
  • Yosra Allouche, Antonio Jiménez, Marino Uceda, M Paz Aguilera, José Juan Gaforio, Gabriel Beltrán. Triterpenic content and chemometric analysis of virgin olive oils from forty olive cultivars. Journal of agricultural and food chemistry. 2009 May; 57(9):3604-10. doi: 10.1021/jf803237z. [PMID: 19326867]
  • Yi-Nan Zhang, Wei Zhang, Di Hong, Lei Shi, Qiang Shen, Jing-Ya Li, Jia Li, Li-Hong Hu. Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities. Bioorganic & medicinal chemistry. 2008 Sep; 16(18):8697-705. doi: 10.1016/j.bmc.2008.07.080. [PMID: 18707891]
  • M Emília Juan, Uwe Wenzel, Hannelore Daniel, Joana M Planas. Erythrodiol, a natural triterpenoid from olives, has antiproliferative and apoptotic activity in HT-29 human adenocarcinoma cells. Molecular nutrition & food research. 2008 May; 52(5):595-9. doi: 10.1002/mnfr.200700300. [PMID: 18384095]
  • Sara Hoet, Luc Pieters, Giulio G Muccioli, Jean-Louis Habib-Jiwan, Fred R Opperdoes, Joëlle Quetin-Leclercq. Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds. Journal of natural products. 2007 Aug; 70(8):1360-3. doi: 10.1021/np070038q. [PMID: 17637068]
  • Ana Marquez-Martin, Rocio De La Puerta, Angeles Fernandez-Arche, Valentina Ruiz-Gutierrez, Parveen Yaqoob. Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells. Cytokine. 2006 Dec; 36(5-6):211-7. doi: 10.1016/j.cyto.2006.12.007. [PMID: 17292619]
  • Hyung-In Moon, Dong Wan Seo, Kyu-Han Kim, Kwang-Hyun Cho, Hee-Chul Eun, Jin Ho Chung. Erythrodiol-3-acetate, pentacyclic triterpenoid from Styrax japonica, expressions of matrix metalloproteinase-1,2 in cultured human skin fibroblasts. Journal of ethnopharmacology. 2005 Mar; 97(3):567-71. doi: 10.1016/j.jep.2005.01.006. [PMID: 15740897]
  • Javier S Perona, Cesar Arcemis, Valentina Ruiz-Gutierrez, Angel Catalá. Effect of dietary high-oleic-acid oils that are rich in antioxidants on microsomal lipid peroxidation in rats. Journal of agricultural and food chemistry. 2005 Feb; 53(3):730-5. doi: 10.1021/jf048374p. [PMID: 15686427]
  • Dalila Smati, Arlette Longeon, Michèle Guyot. 3 Beta-(3,4-dihydroxycinnamoyl)-erythrodiol, a cytotoxic constituent of Zygophyllum geslini collected in the Algerian Sahara. Journal of ethnopharmacology. 2004 Dec; 95(2-3):405-7. doi: 10.1016/j.jep.2004.08.011. [PMID: 15507367]
  • Rosalía Rodríguez-Rodríguez, María Dolores Herrera, Javier S Perona, Valentina Ruiz-Gutiérrez. Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in 'orujo' olive oil, on rat aorta. The British journal of nutrition. 2004 Oct; 92(4):635-42. doi: 10.1079/bjn20041231. [PMID: 15522132]
  • Ayumi Ohsaki, Yoji Imai, Meiko Naruse, Shin-Ichi Ayabe, Kanki Komiyama, Junko Takashima. Four new triterpenoids from Maytenus ilicifolia. Journal of natural products. 2004 Mar; 67(3):469-71. doi: 10.1021/np030379d. [PMID: 15043435]
  • Hong-Jie Zhang, Ghee Teng Tan, Vu Dinh Hoang, Nguyen Van Hung, Nguyen Manh Cuong, D Doel Soejarto, John M Pezzuto, Harry H S Fong. Natural anti-HIV agents. Part IV. Anti-HIV constituents from Vatica cinerea. Journal of natural products. 2003 Feb; 66(2):263-8. doi: 10.1021/np020379y. [PMID: 12608862]
  • Jean Wandji, Francois Tillequin, Dulcie A Mulholland, Jean-Duplex Wansi, Tanee Z Fomum, Victorine Fuendjiep, Francine Libot, Nole Tsabang. Fatty acid esters of triterpenoids and steroid glycosides from Gambeya africana. Planta medica. 2002 Sep; 68(9):822-6. doi: 10.1055/s-2002-34416. [PMID: 12357395]
  • R de la Puerta, E Martínez-Domínguez, V Ruíz-Gutiérrez. Effect of minor components of virgin olive oil on topical antiinflammatory assays. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2000 Sep; 55(9-10):814-9. doi: 10.1515/znc-2000-9-1023. [PMID: 11098836]
  • J H Sung, J O Lee, J K Son, N S Park, M R Kim, J G Kim, D C Moon. Cytotoxic constituents from Solidago virga-aurea var. gigantea MIQ. Archives of pharmacal research. 1999 Dec; 22(6):633-7. doi: 10.1007/bf02975338. [PMID: 10615872]
  • M Amelio, R Rizzo, F Varazini. Determination of sterols, erythrodiol, uvaol and alkanols in olive oils using combined solid-phase extraction, high-performance liquid chromatographic and high-resolution gas chromatographic techniques. Journal of chromatography. 1992 Aug; 606(2):179-85. doi: 10.1016/0021-9673(92)87023-2. [PMID: 1430013]
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