Curcumenol (BioDeep_00000000314)

Main id: BioDeep_00000407249

 

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(3S,3aS,6R,8aS)-3,8-Dimethyl-5-(propan-2-ylidene)-2,3,4,5,6,8a-hexahydro-1H-3a,6-epoxyazulen-6-ol

化学式: C15H22O2 (234.1619712)
中文名称: 莪术烯醇, 莪术醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CC2(O)OC3(CC2=C(C)C)C(C)CCC13
InChI: InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3

描述信息

Curcumenol is a sesquiterpenoid.
(3S,3aS,6R,8aS)-3,8-Dimethyl-5-(propan-2-ylidene)-2,3,4,5,6,8a-hexahydro-1H-3a,6-epoxyazulen-6-ol is a natural product found in Curcuma longa and Curcuma phaeocaulis with data available.
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors
4-Epicurcumenol is a constituent of rhizomes of Curcuma zedoaria (zedoary).
Curcumenol ((+)-Curcumenol) is a potent CYP3A4 inhibitor with an IC50 of 12.6 μM, which is one of constituents in the plants of medicinally important genus of Curcuma zedoaria, with neuroprotection, anti-inflammatory, anti-tumor and hepatoprotective activities. Curcumenol ((+)-Curcumenol) suppresses Akt-mediated NF-κB activation and p38 MAPK signaling pathway in LPS-stimulated BV-2 microglial cells[1][2].
Curcumenol ((+)-Curcumenol) is a potent CYP3A4 inhibitor with an IC50 of 12.6 μM, which is one of constituents in the plants of medicinally important genus of Curcuma zedoaria, with neuroprotection, anti-inflammatory, anti-tumor and hepatoprotective activities. Curcumenol ((+)-Curcumenol) suppresses Akt-mediated NF-κB activation and p38 MAPK signaling pathway in LPS-stimulated BV-2 microglial cells[1][2].

同义名列表

14 个代谢物同义名

(3S,3aS,6R,8aS)-3,8-Dimethyl-5-(propan-2-ylidene)-2,3,4,5,6,8a-hexahydro-1H-3a,6-epoxyazulen-6-ol; 6H-3a,6-Epoxyazulen-6-ol, 1,2,3,4,5,8a-hexahydro-3,8-dimethyl-5-(1-methylethylidene)-; 2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0^{1,5}]undec-6-en-8-ol; 2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol; 9-isopropylidene-2,6-dimethyl-11-oxatricyclo[6.2.1.01,5]undec-6-en-8-ol; 3,8-Dimethyl-5-(1-methylethylidene)-,(3S,3aS,6R,8aS)-; 5,8-Epoxy-9-dien-8-.alpha.-ol-5-.beta.-guiaia-7(11); CC1CCC(C1(O2)C/3)C(C)=CC2(O)C3=C(C)/C; isopropylidene(dimethyl)[?]ol; ISFMXVMWEWLJGJ-UHFFFAOYSA-N; Curcumenol,(S); NCI60_029451; Curcumenol; (+)-Curcumenol



数据库引用编号

19 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)

49 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

  • Jie Li, Yitian Sun, Guohua Li, Chunsong Cheng, Xinbing Sui, Qibiao Wu. The Extraction, Determination, and Bioactivity of Curcumenol: A Comprehensive Review. Molecules (Basel, Switzerland). 2024 Jan; 29(3):. doi: 10.3390/molecules29030656. [PMID: 38338400]
  • Guanghui Zhong, Xudong Cai, Renxiong Wei, Sheng Wei, Xiaodan Cao. Curcumenol improves renal function in 5/6 nephrectomy-induced chronic renal failure rats via the SIRT1/NF-κB pathway. Anatomical record (Hoboken, N.J. : 2007). 2022 Dec; ?(?):. doi: 10.1002/ar.25137. [PMID: 36495299]
  • Xiao Yang, Yifan Zhou, Zhiqian Chen, Chen Chen, Chen Han, Xunlin Li, Haijun Tian, Xiaofei Cheng, Kai Zhang, Tangjun Zhou, Jie Zhao. Curcumenol mitigates chondrocyte inflammation by inhibiting the NF‑κB and MAPK pathways, and ameliorates DMM‑induced OA in mice. International journal of molecular medicine. 2021 10; 48(4):. doi: 10.3892/ijmm.2021.5025. [PMID: 34435650]
  • Bi Wang, Fei Liu, Qi Li, Shu Xu, Xingzeng Zhao, Peilin Xue, Xu Feng. Antifungal activity of zedoary turmeric oil against Phytophthora capsici through damaging cell membrane. Pesticide biochemistry and physiology. 2019 Sep; 159(?):59-67. doi: 10.1016/j.pestbp.2019.05.014. [PMID: 31400785]
  • Yuhua Chen, Yue Sun, Wende Li, Hong Wei, Tianlin Long, Hua Li, Quanhua Xu, Wei Liu. Systems pharmacology dissection of the anti-stroke mechanism for the Chinese traditional medicine Xing-Nao-Jing. Journal of pharmacological sciences. 2018 Jan; 136(1):16-25. doi: 10.1016/j.jphs.2017.11.005. [PMID: 29336875]
  • Chang-Xin Zhou, Li-Sha Zhang, Fei-Fei Chen, Hao-Shu Wu, Jian-Xia Mo, Li-She Gan. Terpenoids from Curcuma wenyujin increased glucose consumption on HepG2 cells. Fitoterapia. 2017 Sep; 121(?):141-145. doi: 10.1016/j.fitote.2017.06.011. [PMID: 28625730]
  • Ezzat Abdel-Lateef, Faten Mahmoud, Olfat Hammam, Eman El-Ahwany, Eman El-Wakil, Sherihan Kandil, Hoda Abu Taleb, Mortada El-Sayed, Hanaa Hassenein. Bioactive chemical constituents of Curcuma longa L. rhizomes extract inhibit the growth of human hepatoma cell line (HepG2). Acta pharmaceutica (Zagreb, Croatia). 2016 Sep; 66(3):387-98. doi: 10.1515/acph-2016-0028. [PMID: 27383887]
  • Weidong Pan, Lixin Yang, Weihong Feng, Limei Lin, Chun Li, Weiwei Liu, Guofeng Gan, Junhong Fan, Jigao Zou, Zhimin Wang, Haifeng Pan. Determination of five sesquiterpenoids in Xingnaojing injection by quantitative analysis of multiple components with a single marker. Journal of separation science. 2015 Oct; 38(19):3313-23. doi: 10.1002/jssc.201500494. [PMID: 26200507]
  • Li-Xia Chen, Qian Zhao, Meng Zhang, Yan-Yan Liang, Jiang-Hao Ma, Xue Zhang, Li-Qin Ding, Feng Zhao, Feng Qiu. Biotransformation of Curcumenol by Mucor polymorphosporus. Journal of natural products. 2015 Apr; 78(4):674-80. doi: 10.1021/np500845z. [PMID: 25821895]
  • Omer Abdalla Ahmed Hamdi, Shevin Rizal Feroz, Jamil A Shilpi, El Hassane Anouar, Abdul Kadir Mukarram, Saharuddin B Mohamad, Saad Tayyab, Khalijah Awang. Spectrofluorometric and molecular docking studies on the binding of curcumenol and curcumenone to human serum albumin. International journal of molecular sciences. 2015 Mar; 16(3):5180-93. doi: 10.3390/ijms16035180. [PMID: 25756376]
  • Aline Augusti Boligon, Thiago Guilherme Schwanz, Mariana Piana, Rose Vanessa Bandeira, Janaína Kieling Frohlich, Thiele Faccim de Brum, Marina Zadra, Margareth Linde Athayde. Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. Natural product research. 2013; 27(1):68-71. doi: 10.1080/14786419.2011.653971. [PMID: 22273350]
  • Xiang-hui Han, Yi-yi Ye, Bao-feng Guo, Sheng Liu. [Effects of platycodin D in combination with different active ingredients of Chinese herbs on proliferation and invasion of 4T1 and MDA-MB-231 breast cancer cell lines]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2012 Jan; 10(1):67-75. doi: 10.3736/jcim20120111. [PMID: 22237277]
  • Dong-Xue Sun, Zhong-Ze Fang, Yan-Yan Zhang, Yun-Feng Cao, Ling Yang, Jun Yin. Inhibitory effects of curcumenol on human liver cytochrome P450 enzymes. Phytotherapy research : PTR. 2010 Aug; 24(8):1213-6. doi: 10.1002/ptr.3102. [PMID: 20148399]