Santalol (BioDeep_00000396395)
PANOMIX_OTCML-2023
代谢物信息卡片
2-Penten-1-ol, 2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl]-, (2Z)-
化学式: C15H24O (220.18270539999997)
中文名称: 檀香醇
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 66.67%
分子结构信息
SMILES: CC(=CCCC1(C2CCC(C2)C1=C)C)CO
InChI: InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)12(2)13-6-7-14(15)9-13/h5,13-14,16H,2,4,6-10H2,1,3H3/b11-5+
描述信息
同义名列表
7 个代谢物同义名
2-Penten-1-ol, 2-methyl-5-[(1S,2R,4R)-2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl]-, (2Z)-; Santalol; (2E)-2-METHYL-5-[(1S,2S,4R)-2-METHYL-3-METHYLIDENEBICYCLO[2.2.1]HEPTAN-2-YL]PENT-2-EN-1-OL; rel-(2E)-2-Methyl-5-[(1R,2R,4S)-2-methyl-3-methylenebicyclo[2.2.1]hept-2-yl]-2-penten-1-ol; (E)-2-methyl-5-[(1S,2S,4R)-2-methyl-3-methylidene-2-bicyclo[2.2.1]heptanyl]pent-2-en-1-ol; (E)-2-methyl-5-((1S,2S,4R)-2-methyl-3-methylenebicyclo[2.2.1]heptan-2-yl)pent-2-en-1-ol; 2-Methyl-5-((1S,2S,4R)-2-methyl-3-methylenebicyclo[2.2.1]heptan-2-yl)pent-2-en-1-ol
数据库引用编号
6 个数据库交叉引用编号
- PubChem: 5368798
- PubChem: 12315259
- MeSH: santalol
- CAS: 11031-45-1
- CAS: 73890-74-1
- medchemexpress: HY-N2059
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)
0 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
- Xiaohong Chen, Yueya Zhang, Haifeng Yan, Meiyun Niu, Yuping Xiong, Xinhua Zhang, Yuan Li, Jaime A Teixeira da Silva, Guohua Ma. Cloning and functional analysis of 1-deoxy-d-xylulose-5-phosphate synthase (DXS) in Santalum album L.
Gene.
2023 Jan; 851(?):146762. doi:
10.1016/j.gene.2022.146762. [PMID: 35933050] - Javad Sharifi-Rad, Cristina Quispe, Aknur Turgumbayeva, Zehra Mertdinç, Sena Tütüncü, Elif Feyza Aydar, Beraat Özçelik, Stępień-Warda Anna, Staniak Mariola, Anna Koziróg, Anna Otlewska, Hubert Antolak, Surjit Sen, Krishnendu Acharya, Natallia Lapava, Simin Emamzadeh-Yazdi, Miquel Martorell, Manoj Kumar, Elena Maria Varoni, Marcello Iriti, Daniela Calina. Santalum Genus: phytochemical constituents, biological activities and health promoting-effects.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2023 Jan; 78(1-2):9-25. doi:
10.1515/znc-2022-0076. [PMID: 36069757] - Yuchen Wang, Xiaowei Gong, Fan Li, Shasha Zuo, Minggang Li, Jiangyuan Zhao, Xiulin Han, Mengliang Wen. Optimized biosynthesis of santalenes and santalols in Saccharomyces cerevisiae.
Applied microbiology and biotechnology.
2021 Dec; 105(23):8795-8804. doi:
10.1007/s00253-021-11661-9. [PMID: 34738171] - Ajay Bommareddy, Danielle McGlynn, Marissa Lewis, Lauren Lockus, Jonathan Seward, Ka Lok Hong, Adam L VanWert, Chandradhar Dwivedi. Akt/survivin pathway inhibition enhances the apoptotic cell death-induced by alpha-santalol in human prostate cancer cells.
Fitoterapia.
2020 Jun; 143(?):104552. doi:
10.1016/j.fitote.2020.104552. [PMID: 32173422] - Ajay Bommareddy, Sarah Brozena, James Steigerwalt, Terra Landis, Sarah Hughes, Erica Mabry, Aaron Knopp, Adam L VanWert, Chandradhar Dwivedi. Medicinal properties of alpha-santalol, a naturally occurring constituent of sandalwood oil: review.
Natural product research.
2019 Feb; 33(4):527-543. doi:
10.1080/14786419.2017.1399387. [PMID: 29130352] - Ajay Bommareddy, Kacey Knapp, Abigail Nemeth, James Steigerwalt, Terra Landis, Adam L Vanwert, Harsha P Gorijavolu, Chandradhar Dwivedi. Alpha-Santalol, a Component of Sandalwood Oil Inhibits Migration of Breast Cancer Cells by Targeting the β-catenin Pathway.
Anticancer research.
2018 08; 38(8):4475-4480. doi:
10.21873/anticanres.12750. [PMID: 30061212] - Yuchen Wang, Mengliang Wen, Minggang Li, Jiangyuan Zhao, Xiulin Han. [Progress in biosynthesis of santalene and santalol].
Sheng wu gong cheng xue bao = Chinese journal of biotechnology.
2018 Jun; 34(6):862-875. doi:
10.13345/j.cjb.170465. [PMID: 29943532] - Tae Hoon Kim, Tsutomu Hatano, Keinosuke Okamoto, Takashi Yoshida, Hiroshi Kanzaki, Michiko Arita, Hideyuki Ito. Antifungal and Ichthyotoxic Sesquiterpenoids from Santalum album Heartwood.
Molecules (Basel, Switzerland).
2017 Jul; 22(7):. doi:
10.3390/molecules22071139. [PMID: 28698478] - Cecilia Cagliero, Carlo Bicchi, Chiara Cordero, Erica Liberto, Patrizia Rubiolo, Barbara Sgorbini. Analysis of essential oils and fragrances with a new generation of highly inert gas chromatographic columns coated with ionic liquids.
Journal of chromatography. A.
2017 Apr; 1495(?):64-75. doi:
10.1016/j.chroma.2017.03.029. [PMID: 28343686] - Jose M Celedon, Angela Chiang, Macaire M S Yuen, Maria L Diaz-Chavez, Lufiani L Madilao, Patrick M Finnegan, Elizabeth L Barbour, Jörg Bohlmann. Heartwood-specific transcriptome and metabolite signatures of tropical sandalwood (Santalum album) reveal the final step of (Z)-santalol fragrance biosynthesis.
The Plant journal : for cell and molecular biology.
2016 05; 86(4):289-99. doi:
10.1111/tpj.13162. [PMID: 26991058] - J M Celedon, J Bohlmann. Genomics-Based Discovery of Plant Genes for Synthetic Biology of Terpenoid Fragrances: A Case Study in Sandalwood oil Biosynthesis.
Methods in enzymology.
2016; 576(?):47-67. doi:
10.1016/bs.mie.2016.03.008. [PMID: 27480682] - Sebastiano Pantò, Danilo Sciarrone, Mariarosa Maimone, Carla Ragonese, Salvatore Giofrè, Paola Donato, Sara Farnetti, Luigi Mondello. Performance evaluation of a versatile multidimensional chromatographic preparative system based on three-dimensional gas chromatography and liquid chromatography-two-dimensional gas chromatography for the collection of volatile constituents.
Journal of chromatography. A.
2015 Oct; 1417(?):96-103. doi:
10.1016/j.chroma.2015.09.039. [PMID: 26410184] - Tadaaki Satou, Yuko Ogawa, Kazuo Koike. Relationship Between Emotional Behavior in Mice and the Concentration of (+)-α-Santalol in the Brain.
Phytotherapy research : PTR.
2015 Aug; 29(8):1246-50. doi:
10.1002/ptr.5372. [PMID: 25991569] - Jessie Moniodis, Christopher G Jones, E Liz Barbour, Julie A Plummer, Emilio L Ghisalberti, Joerg Bohlmann. The transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of Western Australian sandalwood (Santalum spicatum).
Phytochemistry.
2015 May; 113(?):79-86. doi:
10.1016/j.phytochem.2014.12.009. [PMID: 25624157] - M Sharma, C Levenson, R H Bell, S A Anderson, J B Hudson, C C Collins, M E Cox. Suppression of lipopolysaccharide-stimulated cytokine/chemokine production in skin cells by sandalwood oils and purified α-santalol and β-santalol.
Phytotherapy research : PTR.
2014 Jun; 28(6):925-32. doi:
10.1002/ptr.5080. [PMID: 24318647] - Biswapriya B Misra, Satyahari Dey. Evaluation of in vivo anti-hyperglycemic and antioxidant potentials of α-santalol and sandalwood oil.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2013 Mar; 20(5):409-16. doi:
10.1016/j.phymed.2012.12.017. [PMID: 23369343] - Biswapriya B Misra, Satyahari Dey. TLC-bioautographic evaluation of in vitro anti-tyrosinase and anti-cholinesterase potentials of sandalwood oil.
Natural product communications.
2013 Feb; 8(2):253-6. doi:
. [PMID: 23513742] - Maria L Diaz-Chavez, Jessie Moniodis, Lufiani L Madilao, Sharon Jancsik, Christopher I Keeling, Elizabeth L Barbour, Emilio L Ghisalberti, Julie A Plummer, Christopher G Jones, Jörg Bohlmann. Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol.
PloS one.
2013; 8(9):e75053. doi:
10.1371/journal.pone.0075053. [PMID: 24324844] - Pankaj P Daramwar, Prabhakar Lal Srivastava, Balaraman Priyadarshini, Hirekodathakallu V Thulasiram. Preparative separation of α- and β-santalenes and (Z)-α- and (Z)-β-santalols using silver nitrate-impregnated silica gel medium pressure liquid chromatography and analysis of sandalwood oil.
The Analyst.
2012 Oct; 137(19):4564-70. doi:
10.1039/c2an35575b. [PMID: 22900258] - Ajay Bommareddy, Brittny Rule, Adam L VanWert, Sreevidya Santha, Chandradhar Dwivedi. α-Santalol, a derivative of sandalwood oil, induces apoptosis in human prostate cancer cells by causing caspase-3 activation.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Jun; 19(8-9):804-11. doi:
10.1016/j.phymed.2012.04.003. [PMID: 22571975] - Hyun Sik Roh, Kye Chung Park, Chung Gyoo Park. Repellent effect of santalol from sandalwood oil against Tetranychus urticae (Acari: Tetranychidae).
Journal of economic entomology.
2012 Apr; 105(2):379-85. doi:
10.1603/ec11262. [PMID: 22606807] - Toshio Hasegawa, Hiroaki Izumi, Yuji Tajima, Hideo Yamada. Structure-odor relationships of α-santalol derivatives with modified side chains.
Molecules (Basel, Switzerland).
2012 Feb; 17(2):2259-70. doi:
10.3390/molecules17022259. [PMID: 22357322] - Manickam Paulpandi, Soundarapandian Kannan, Ramar Thangam, Krishnasamy Kaveri, Palani Gunasekaran, Chandrababu Rejeeth. In vitro anti-viral effect of β-santalol against influenza viral replication.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 Feb; 19(3-4):231-5. doi:
10.1016/j.phymed.2011.11.006. [PMID: 22192867] - Xin Hua Zhang, Jaime A Teixeira da Silva, Yong Xia Jia, Jie Tang Zhao, Guo Hua Ma. Chemical composition of volatile oils from the pericarps of Indian sandalwood (Santalum album) by different extraction methods.
Natural product communications.
2012 Jan; 7(1):93-6. doi:
". [PMID: 22428257] - Xiaoying Zhang, Chandradhar Dwivedi. Skin cancer chemoprevention by α-santalol.
Frontiers in bioscience (Scholar edition).
2011 01; 3(2):777-87. doi:
10.2741/s186. [PMID: 21196411] - Constanze Brocke, Marcus Eh, Anja Finke. Recent developments in the chemistry of sandalwood odorants.
Chemistry & biodiversity.
2008 Jun; 5(6):1000-10. doi:
10.1002/cbdv.200890080. [PMID: 18618410] - Ajay Bommareddy, Justin Hora, Bruce Cornish, Chandradhar Dwivedi. Chemoprevention by alpha-santalol on UVB radiation-induced skin tumor development in mice.
Anticancer research.
2007 Jul; 27(4B):2185-8. doi:
". [PMID: 17695502] - Manjinder Kaur, Chapla Agarwal, Rana P Singh, Xiangming Guan, Chandradhar Dwivedi, Rajesh Agarwal. Skin cancer chemopreventive agent, {alpha}-santalol, induces apoptotic death of human epidermoid carcinoma A431 cells via caspase activation together with dissipation of mitochondrial membrane potential and cytochrome c release.
Carcinogenesis.
2005 Feb; 26(2):369-80. doi:
10.1093/carcin/bgh325. [PMID: 15528219] - Qun Hu, Wilhelm Boland, Ji-Kai Liu. 6-Substituted indanoyl isoleucine conjugate induces tobacco plant responses in secondary metabolites.
Zeitschrift fur Naturforschung. C, Journal of biosciences.
2005 Jan; 60(1-2):1-4. doi:
10.1515/znc-2005-1-201. [PMID: 15787235] - Christian Chapuis. In the quest for a virtual pseudo receptor for sandalwood-like odorants. Part I: The empirical approach.
Chemistry & biodiversity.
2004 Jul; 1(7):980-1021. doi:
10.1002/cbdv.200490084. [PMID: 17191895] - T Hongratanaworakit, E Heuberger, G Buchbauer. Evaluation of the effects of East Indian sandalwood oil and alpha-santalol on humans after transdermal absorption.
Planta medica.
2004 Jan; 70(1):3-7. doi:
10.1055/s-2004-815446. [PMID: 14765284] - G Buchbauer, A Sunara, P Weiss-Greiler, P Wolschann. Synthesis and olfactoric activity of side-chain modified beta-santalol analogues.
European journal of medicinal chemistry.
2001 Jul; 36(7-8):673-83. doi:
10.1016/s0223-5234(01)01271-5. [PMID: 11600236] - H Okugawa, R Ueda, K Matsumoto, K Kawanishi, K Kato. Effects of sesquiterpenoids from "Oriental incenses" on acetic acid-induced writhing and D2 and 5-HT2A receptors in rat brain.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2000 Oct; 7(5):417-22. doi:
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Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2000 Mar; 23(3):152-4. doi:
". [PMID: 12575135] - G Buchbauer, F Zechmeister-Machhart, P Weiss-Greiler, P Wolschann. Structure-activity relationships of sandalwood odorants: synthesis and odour of methyl-beta-santalol.
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