Friedelin (BioDeep_00000000543)

   

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4.ALPHA.,4A.ALPHA.,6A.BETA.,6B.ALPHA.,8A.ALPHA.,12A.ALPHA.,12B.BETA.,14A.ALPHA.,14B.BETA.))-

化学式: C30H50O (426.386145)
中文名称: 软木三萜酮, 弗里德林, 木栓酮, 无羁萜
谱图信息: 最多检出来源 Viridiplantae(plant) 6.52%

分子结构信息

SMILES: CC1(C)CCC2(C)CCC3(C)C4CCC5C(C)(C)C(=O)CCC5(C)C4CCC3(C)C2C1
InChI: InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3

描述信息

Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone.
Friedelin is a natural product found in Diospyros eriantha, Salacia chinensis, and other organisms with data available.
A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork.
Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as pomegranate, sugar apple, apple, and mammee apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

同义名列表

28 个代谢物同义名

3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4.ALPHA.,4A.ALPHA.,6A.BETA.,6B.ALPHA.,8A.ALPHA.,12A.ALPHA.,12B.BETA.,14A.ALPHA.,14B.BETA.))-; (4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one; 24,25,26-TRINOROLEANAN-3-ONE, 5,9,13-TRIMETHYL-, (4.BETA.,5.BETA.,8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.)-; 3(2H)-Picenone, eicosahydro-4,4a,6b,8a,11,11,12b,14a-octamethyl-, (4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-; (4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one; 24,25,26-trinoroleanan-3-one, 5,9,13-trimethyl-, (4beta,5beta,8alpha,9beta,10alpha,13alpha,14beta)-; 24,25,26-Trinoroleanan-3-one, 5,9,13-trimethyl-,(4b,5b,8a,9b,10a,13a,14b)-; Friedelin, analytical standard; D:A-Friedooleanan-3-one (VAN); Friedelin, technical grade; D:A-Friedooleanan-3-one; friedelan-3-one; 3-OXOFRIEDELANE; 3-friedelanone; FRIEDELIN [MI]; (-)-Friedelin; friedelanone; friedeline; Friedelin; Fridelin; D:A-Friedooleanan-3-one (VAN) (8CI)(9CI); DA-friedooleanan-3-one; EINECS 209-205-1; 855022_ALDRICH; NSC 55141; 559-74-0; C08626; Friedlein



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

769 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

  • John Staton Laws, Scott D Smid. Characterizing cannabis-prevalent terpenes for neuroprotection reveal a role for α and β-pinenes in mitigating amyloid β-evoked neurotoxicity and aggregation in vitro. Neurotoxicology. 2024 Jan; 100(?):16-24. doi: 10.1016/j.neuro.2023.12.004. [PMID: 38070653]
  • Santosh Kumar Singh, Shweta Shrivastava, Awdhesh Kumar Mishra, Darshan Kumar, Vijay Kant Pandey, Pratima Srivastava, Biswaranjan Pradhan, Bikash Chandra Behera, Ashutosh Bahuguna, Kwang-Hyun Baek. Friedelin: Structure, Biosynthesis, Extraction, and Its Potential Health Impact. Molecules (Basel, Switzerland). 2023 Nov; 28(23):. doi: 10.3390/molecules28237760. [PMID: 38067489]
  • Yunfeng Luo, Xiaoli Ma, Yufan Qiu, Yun Lu, Siyu Shen, Yang Li, Haiyun Gao, Kang Chen, Jiawei Zhou, Tianyuan Hu, Lichan Tu, Huan Zhao, Dan Li, Faqiang Leng, Wei Gao, Tao Jiang, Changli Liu, Luqi Huang, Ruibo Wu, Yuru Tong. Structural and Catalytic Insight into the Unique Pentacyclic Triterpene Synthase TwOSC. Angewandte Chemie (International ed. in English). 2023 Oct; ?(?):e202313429. doi: 10.1002/anie.202313429. [PMID: 37840440]
  • Brice Maxime Nkouayeb Nangmou, Hermine Laure Maza Djomkam, Georges Bellier Tabekoueng, Willifred Dongmo Tékapi Tsopgni, Gabin Thierry Mbahbou Bitchagno, Michel Arnaud Mbock, Raceline Gounoue Kamkumo, Marcel Frese, Bruno Ndjakou Lenta, Silvère Augustin Ngouela, Nobert Sewald, Anatole Guy Blaise Azebaze. Bioguided Fractionation and Isolation of an Antiplasmodial Saponin from the Roots of Nauclea xanthoxylon (A.Chev.) Aubrév. (Rubiaceae). Chemistry & biodiversity. 2023 Mar; ?(?):e202200271. doi: 10.1002/cbdv.202200271. [PMID: 36890112]
  • Janaine Almeida Neto, Daniel Amando Nery, Katia Simoni Bezerra Lima, Maria Eduarda Gomes da Cruz Silva, Tarcísio Cícero de Lima Araújo, Nathália Andrezza Carvalho de Souza, Rodolfo Hideki Vicente Nishimura, Camila de Souza Araújo, Ana Paula de Oliveira, Jackson Roberto Guedes da Silva Almeida, Larissa Araújo Rolim. Phytochemical Characterization of Cannabis sativa L. Roots from Northeastern Brazil. Chemistry & biodiversity. 2023 Jan; ?(?):e202201039. doi: 10.1002/cbdv.202201039. [PMID: 36662379]
  • Xiao-Chao Chen, Yun Lu, Yuan Liu, Jia-Wei Zhou, Yi-Feng Zhang, Hai-Yun Gao, Dan Li, Wei Gao. Identification of a cytochrome P450 from Tripterygium hypoglaucum (Levl.) Hutch that catalyzes polpunonic acid formation in celastrol biosynthesis. Chinese journal of natural medicines. 2022 Sep; 20(9):691-700. doi: 10.1016/s1875-5364(22)60205-x. [PMID: 36162954]
  • Marva Sandhu, Hafiz Muhammad Irfan, Shahid Ali Shah, Madiha Ahmed, Iffat Naz, Muhammad Akram, Humaira Fatima, Ayesha Shuja Farooq. Friedelin Attenuates Neuronal Dysfunction and Memory Impairment by Inhibition of the Activated JNK/NF-κB Signalling Pathway in Scopolamine-Induced Mice Model of Neurodegeneration. Molecules (Basel, Switzerland). 2022 Jul; 27(14):. doi: 10.3390/molecules27144513. [PMID: 35889382]
  • Mapula Razwinani, Keolebogile Shirley Motaung. The influence of friedelin, resinone, tingenone and betulin of compounds on chondrogenic differentiation of porcine adipose-derived mesenchymal stem cells (pADMSCs). Biochimie. 2022 May; 196(?):234-242. doi: 10.1016/j.biochi.2022.01.018. [PMID: 35121053]
  • Bruna F Mazzeu, Tatiana M Souza-Moreira, Andrew A Oliveira, Melissa Remlinger, Lidiane G Felippe, Sandro R Valentini, Rafael V C Guido, Cleslei F Zanelli, Maysa Furlan. The Methionine 549 and Leucine 552 Residues of Friedelin Synthase from Maytenus ilicifolia Are Important for Substrate Binding Specificity. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226806. [PMID: 34833897]
  • Fabio Ferrini, Daniele Fraternale, Sabrina Donati Zeppa, Giancarlo Verardo, Andrea Gorassini, Vittoria Carrabs, Maria Cristina Albertini, Piero Sestili. Yield, Characterization, and Possible Exploitation of Cannabis Sativa L. Roots Grown under Aeroponics Cultivation. Molecules (Basel, Switzerland). 2021 Aug; 26(16):. doi: 10.3390/molecules26164889. [PMID: 34443479]
  • Benjamin Kingsley Harley, Isaac Kingsley Amponsah, Inemesit Okon Ben, Donatus Wewura Adongo, Nana Ama Mireku-Gyimah, Michael Kwesi Baah, Abraham Yeboah Mensah, Theophilus Christian Fleischer. Myrianthus libericus: Possible mechanisms of hypoglycaemic action and in silico prediction of pharmacokinetics and toxicity profile of its bioactive metabolite, friedelan-3-one. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111379. doi: 10.1016/j.biopha.2021.111379. [PMID: 33761602]
  • Christudas Sunil, Santiagu Stephen Irudayaraj, Veeramuthu Duraipandiyan, Sara T Alrashood, Sulaiman Ali Alharbi, Savarimuthu Ignacimuthu. Friedelin exhibits antidiabetic effect in diabetic rats via modulation of glucose metabolism in liver and muscle. Journal of ethnopharmacology. 2021 Mar; 268(?):113659. doi: 10.1016/j.jep.2020.113659. [PMID: 33271243]
  • Peng Li, Shao-Xin Shen, Ling-Xue Liu, Jian-Hua Xu, Xin-Hua Ma, Dong-Mei Shi, Zhi-Qiang Zhang. A new demethyl abietane diterpenoid from the roots of Tripterygium wilfordii. Natural product research. 2020 Nov; 34(21):3094-3100. doi: 10.1080/14786419.2019.1610749. [PMID: 31230492]
  • Aristide Mfifen Munvera, Blandine Marlyse Wache Ouahouo, Pierre Mkounga, Michelle Ines Kanko Mbekou, Shehla Nuzhat, Muhammad Iqbal Choudhary, Augustin Ephrem Nkengfack. Chemical constituents from leaves and trunk bark of Rinorea oblongifolia (Violaceae). Natural product research. 2020 Jul; 34(14):2014-2021. doi: 10.1080/14786419.2019.1573230. [PMID: 30784307]
  • Jung Yeon Han, Chang-Ho Ahn, Prakash Babu Adhikari, Subramanyam Kondeti, Yong Eui Choi. Functional characterization of an oxidosqualene cyclase (PdFRS) encoding a monofunctional friedelin synthase in Populus davidiana. Planta. 2019 Jan; 249(1):95-111. doi: 10.1007/s00425-018-2985-8. [PMID: 30145615]
  • Keng Hong Tee, Gwendoline Cheng Lian Ee, Intan Safinar Ismail, Thiruventhan Karunakaran, Soek Sin Teh, Vivien Yi Mian Jong, Siti Mariam Mohd Nor. A new coumarin from stem bark of Calophyllum wallichianum. Natural product research. 2018 Nov; 32(21):2565-2570. doi: 10.1080/14786419.2018.1428588. [PMID: 29355031]
  • Zhijian Li, Qingxi Min, Haoji Huang, Ruixuan Liu, Yongyan Zhu, Quanhong Zhu. Design, synthesis and biological evaluation of seco-A-pentacyclic triterpenoids-3,4-lactone as potent non-nucleoside HBV inhibitors. Bioorganic & medicinal chemistry letters. 2018 05; 28(9):1501-1506. doi: 10.1016/j.bmcl.2018.03.076. [PMID: 29627260]
  • Thaís B Alves, Tatiana M Souza-Moreira, Sandro R Valentini, Cleslei F Zanelli, Maysa Furlan. Friedelin in Maytenus ilicifolia Is Produced by Friedelin Synthase Isoforms. Molecules (Basel, Switzerland). 2018 Mar; 23(3):. doi: 10.3390/molecules23030700. [PMID: 29558378]
  • Jin-Ah Lee, Sang Keun Ha, Young-Chan Kim, Inwook Choi. Effects of friedelin on the intestinal permeability and bioavailability of apigenin. Pharmacological reports : PR. 2017 Oct; 69(5):1044-1048. doi: 10.1016/j.pharep.2017.04.012. [PMID: 28939344]
  • CuiCui Jia, Tong Han, Jun Xu, ShengGe Li, YaTing Sun, DaHong Li, ZhanLin Li, HuiMing Hua. A new biflavonoid and a new triterpene from the leaves of Garcinia paucinervis and their biological activities. Journal of natural medicines. 2017 Oct; 71(4):642-649. doi: 10.1007/s11418-017-1092-7. [PMID: 28550652]
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  • Tatiana M Souza-Moreira, Thaís B Alves, Karina A Pinheiro, Lidiane G Felippe, Gustavo M A De Lima, Tatiana F Watanabe, Cristina C Barbosa, Vânia A F F M Santos, Norberto P Lopes, Sandro R Valentini, Rafael V C Guido, Maysa Furlan, Cleslei F Zanelli. Friedelin Synthase from Maytenus ilicifolia: Leucine 482 Plays an Essential Role in the Production of the Most Rearranged Pentacyclic Triterpene. Scientific reports. 2016 11; 6(?):36858. doi: 10.1038/srep36858. [PMID: 27874020]
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  • Qiang Wei, Xiao-ying Ji, Fei Xu, Qian-rong Li, Hao Yin. [Chemical Constituents from Leaves of Hibiscus syriacus and Their α-Glucosidase Inhibitory Activities]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 May; 38(5):975-9. doi: . [PMID: 26767290]
  • Paulrayer Antonisamy, Veeramuthu Duraipandiyan, Adithan Aravinthan, Naif Abdullah Al-Dhabi, Savarimuthu Ignacimuthu, Ki Choon Choi, Jong-Hoon Kim. Protective effects of friedelin isolated from Azima tetracantha Lam. against ethanol-induced gastric ulcer in rats and possible underlying mechanisms. European journal of pharmacology. 2015 Mar; 750(?):167-75. doi: 10.1016/j.ejphar.2015.01.015. [PMID: 25617794]
  • Ahmad Azri Fitri Bin Ismail, Gwendoline Cheng Lian Ee, Shaari Bin Daud, Soek Sin Teh, Najihah Mohd Hashim, Khalijah Awang. Venuloxanthone, a new pyranoxanthone from the stem bark of Calophyllum venulosum. Journal of Asian natural products research. 2015; 17(11):1104-8. doi: 10.1080/10286020.2015.1047353. [PMID: 26023810]
  • Hai-jun Hu, Qing Liu, Ying-bo Yang, Li Yang, Zheng-tao Wang. [Chemical constituents of Clerodendrum trichotomum Leaves]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Sep; 37(9):1590-3. doi: . [PMID: 25857158]
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  • Xing-Rong Peng, Jie-Qing Liu, Cui-Fang Wang, Xu-Yang Li, Yi Shu, Lin Zhou, Ming-Hua Qiu. Hepatoprotective effects of triterpenoids from Ganoderma cochlear. Journal of natural products. 2014 Apr; 77(4):737-43. doi: 10.1021/np400323u. [PMID: 24559087]
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  • Christudas Sunil, Veeramuthu Duraipandiyan, Savarimuthu Ignacimuthu, Naif Abdullah Al-Dhabi. Antioxidant, free radical scavenging and liver protective effects of friedelin isolated from Azima tetracantha Lam. leaves. Food chemistry. 2013 Aug; 139(1-4):860-5. doi: 10.1016/j.foodchem.2012.12.041. [PMID: 23561182]
  • Jun Chen, Jian-Hua Wei, Shao-Fang Cai, Hong-Jian Zhang, Xiao-Hua Zhang, Wen-Jing Liang, Shan-Guang Wu. [Chemical constituents in whole herb of Bidens pilosa var. radiata]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Mar; 36(3):410-3. doi: . [PMID: 24010324]
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