3-Butylidene-1(3H)-isobenzofuranone (BioDeep_00000000323)

 

Secondary id: BioDeep_00000227164, BioDeep_00000279236, BioDeep_00000872173, BioDeep_00001867488

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


InChI=1/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8

化学式: C12H12O2 (188.0837252)
中文名称: 丁烯基苯酞
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 14.29%

分子结构信息

SMILES: c1ccc2c(c1)C(=O)O/C/2=C\CCC
InChI: InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+

描述信息

(Z)-3-butylidenephthalide is a gamma-lactone that is phthalide substituted by a butylidene group at position 3. Isolated from Ligusticum porteri, it exhibits hypoglycemic activity. It has a role as a metabolite, a hypoglycemic agent and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a member of 2-benzofurans and a gamma-lactone. It is functionally related to a 2-benzofuran-1(3H)-one.
Butylidenephthalide is a natural product found in Ligusticum striatum, Angelica sinensis, and other organisms with data available.
(Z)-3-Butylidene-1(3H)-isobenzofuranone is found in herbs and spices. (Z)-3-Butylidene-1(3H)-isobenzofuranone is a constituent of Angelica glauca
Flavouring ingredient. 3-Butylidene-1(3H)-isobenzofuranone is found in wild celery and lovage.
3-Butylidenephthalide (Butylidenephthalide) is a phthalic anhydride derivative identified in Ligusticum chuanxiong Hort, and has larvicidal activity (LC50 of 1.56 mg/g for Spodoptera litura larvae)[1].
3-Butylidenephthalide (Butylidenephthalide) is a phthalic anhydride derivative identified in Ligusticum chuanxiong Hort, and has larvicidal activity (LC50 of 1.56 mg/g for Spodoptera litura larvae)[1].

同义名列表

32 个代谢物同义名

InChI=1/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8; (3E)-3-butylidene-1,3-dihydro-2-benzofuran-1-one; 1(3H)-Isobenzofuranone, 3-butylidene-, (3Z)-; 1(3H)-ISOBENZOFURANONE, 3-BUTYLIDENE-, (Z)-; (3Z)-3-BUTYLIDENE-1(3H)-ISOBENZOFURANONE; (3Z)-3-Butylidene-2-benzofuran-1(3H)-one; (Z)-3-butylideneisobenzofuran-1(3H)-one; (3Z)-3-butylidene-2-benzofuran-1-one; (3Z)-3-butylideneisobenzofuran-1-one; 3-Butylideneisobenzofuran-1(3H)-one; 3-butylidene-1(3H)-isobenzofuranone; trans-3n-butylidenephthalide; 3-Butylidenephthalide, (Z)-; WMBOCUXXNSOQHM-FLIBITNWSA-N; 3-Butylidenephthalide, 8ci; BUTYLIDENEPHTHALIDE, (Z)-; (e)-3-Butylidenephthalide; (Z)-3-Butylidenephthalide; Phthalide, 3-butylidene-; 3-Butylidenephthalide-d8; (E)-Butylidene phthalide; (Z)-Butylidenephthalide; 3-Butylidene-phthalide; Z-butylidenephthalide; n-butylidenephthalide; 3-Butylidenephthalide; butylidenephthalide; Ligusticum lactone; UNII-6GM611H175; 6GM611H175; FEMA 3333; BdPh



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(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)

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

  • Kaidi Cui, Ya He, Mengke Wang, Min Li, Chaofan Jiang, Meizi Wang, Leiming He, Fulong Zhang, Lin Zhou. Antifungal activity of Ligusticum chuanxiong essential oil and its active composition butylidenephthalide against Sclerotium rolfsii. Pest management science. 2023 Sep; ?(?):. doi: 10.1002/ps.7751. [PMID: 37656744]
  • Kang-Yun Lu, Kingsley Theras Primus Dass, Shinn-Zong Lin, Yu-Hua Tseng, Shih-Ping Liu, Horng-Jyh Harn. N-butylidenephthalide ameliorates high-fat diet-induced obesity in mice and promotes browning through adrenergic response/AMPK activation in mouse beige adipocytes. Biochimica et biophysica acta. Molecular and cell biology of lipids. 2021 12; 1866(12):159033. doi: 10.1016/j.bbalip.2021.159033. [PMID: 34487913]
  • Kai-Fu Chang, Xiao-Fan Huang, Yu-Ling Lin, Kuang-Wen Liao, Ming-Chang Hsieh, Jinghua Tsai Chang, Nu-Man Tsai. Positively Charged Nanoparticle Delivery of n-Butylidenephthalide Enhances Antitumor Effect in Hepatocellular Carcinoma. BioMed research international. 2021; 2021(?):8817875. doi: 10.1155/2021/8817875. [PMID: 33791383]
  • Cheng Luo, Dong-Liang Li, Yang Wang, Shan-Shan Guo, Shu-Shan Du. Bioactivities of 3-Butylidenephthalide and n-Butylbenzene from the Essential Oil ofLigusticum jeholense against Stored-product Insects. Journal of oleo science. 2019 Sep; 68(9):931-937. doi: 10.5650/jos.ess19080. [PMID: 31413242]
  • Wonseok Lee, Hye Ryoung Koo, You-Jin Choi, Jin Gyu Choi, Myung Sook Oh, Xing Jin, Munki Choo, Sunghyouk Park, Yoo-Seong Jeong, Suk-Jae Chung, Byung-Hoon Lee. Z-ligustilide and n-Butylidenephthalide Isolated from the Aerial Parts of Angelica tenuissima Inhibit Lipid Accumulation In Vitro and In Vivo. Planta medica. 2019 Jul; 85(9-10):719-728. doi: 10.1055/a-0901-1307. [PMID: 31137047]
  • Hong-Wei Gao, Kai-Fu Chang, Xiao-Fan Huang, Yu-Ling Lin, Jun-Cheng Weng, Kuang-Wen Liao, Nu-Man Tsai. Antitumor Effect of n-Butylidenephthalide Encapsulated on B16/F10 Melanoma Cells In Vitro with a Polycationic Liposome Containing PEI and Polyethylene Glycol Complex. Molecules (Basel, Switzerland). 2018 Dec; 23(12):. doi: 10.3390/molecules23123224. [PMID: 30563276]
  • Hui-Fei Wu, Xiang-Yu Wang, Ji-Feng Deng, Shi-Jian Quan, Qi Wang, Wei-Rong Li. Pharmacokinetic Profiling of Butylidenephthalide and Alisol B in Danggui-Shaoyao-San in Rats. European journal of drug metabolism and pharmacokinetics. 2018 Dec; 43(6):645-653. doi: 10.1007/s13318-018-0476-8. [PMID: 29704095]
  • Hyun Kyung Kim, Seung Ju Lee, Bang-Yeon Hwang, Jong Ung Yoon, Gil-Hah Kim. Acaricidal and repellent effects of Cnidium officinale-derived material against Dermanyssus gallinae (Acari: Dermanyssidae). Experimental & applied acarology. 2018 Apr; 74(4):403-414. doi: 10.1007/s10493-018-0249-8. [PMID: 29569074]
  • Yi-Ju Su, Sung-Ying Huang, Yu-Hui Ni, Kuan-Fu Liao, Sheng-Chun Chiu. Anti-Tumor and Radiosensitization Effects of N-Butylidenephthalide on Human Breast Cancer Cells. Molecules (Basel, Switzerland). 2018 Jan; 23(2):. doi: 10.3390/molecules23020240. [PMID: 29370116]
  • Kuan-Fu Liao, Tsung-Lang Chiu, Sung-Ying Huang, Teng-Fu Hsieh, Shu-Fang Chang, Jhen-Wei Ruan, Shee-Ping Chen, Cheng-Yoong Pang, Sheng-Chun Chiu. Anti-Cancer Effects of Radix Angelica Sinensis (Danggui) and N-Butylidenephthalide on Gastric Cancer: Implications for REDD1 Activation and mTOR Inhibition. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2018; 48(6):2231-2246. doi: 10.1159/000492641. [PMID: 30114701]
  • Iveta Bartoňková, Zdeněk Dvořák. Essential oils of culinary herbs and spices display agonist and antagonist activities at human aryl hydrocarbon receptor AhR. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Jan; 111(?):374-384. doi: 10.1016/j.fct.2017.11.049. [PMID: 29191726]
  • Sheng-Chun Chiu, Tsung-Lang Chiu, Sung-Ying Huang, Shu-Fang Chang, Shee-Ping Chen, Cheng-Yoong Pang, Teng-Fu Hsieh. Potential therapeutic effects of N-butylidenephthalide from Radix Angelica Sinensis (Danggui) in human bladder cancer cells. BMC complementary and alternative medicine. 2017 Dec; 17(1):523. doi: 10.1186/s12906-017-2034-3. [PMID: 29207978]
  • Karthyayani Rajamani, Jen-Wei Liu, Cheng-Han Wu, I-Tsang Chiang, Deng-Huwei You, Si-Yin Lin, Dean-Kuo Hsieh, Shinn-Zong Lin, Horng-Jyh Harn, Tzyy-Wen Chiou. n-Butylidenephthalide exhibits protection against neurotoxicity through regulation of tryptophan 2, 3 dioxygenase in spinocerebellar ataxia type 3. Neuropharmacology. 2017 05; 117(?):434-446. doi: 10.1016/j.neuropharm.2017.02.014. [PMID: 28223212]
  • Yun Mi Lee, Yu-Ri Lee, Chan-Sik Kim, Kyuhyung Jo, Eunjin Sohn, Jin Sook Kim, Junghyun Kim. Cnidium officinale extract and butylidenephthalide inhibits retinal neovascularization in vitro and in vivo. BMC complementary and alternative medicine. 2016 Jul; 16(?):231. doi: 10.1186/s12906-016-1216-8. [PMID: 27435599]
  • Danita Champakaew, Anuluck Junkum, Udom Chaithong, Atchariya Jitpakdi, Doungrat Riyong, Anchalee Wannasan, Jitrawadee Intirach, Roongtawan Muangmoon, Arpaporn Chansang, Benjawan Tuetun, Benjawan Pitasawat. Assessment of Angelica sinensis (Oliv.) Diels as a repellent for personal protection against mosquitoes under laboratory and field conditions in northern Thailand. Parasites & vectors. 2016 06; 9(1):373. doi: 10.1186/s13071-016-1650-y. [PMID: 27357395]
  • Yun Mi Lee, Yu Ri Lee, Jin Sook Kim, Young Ho Kim, Junghyun Kim. Cinidium officinale and its Bioactive Compound, Butylidenephthalide, Inhibit Laser-Induced Choroidal Neovascularization in a Rat Model. Molecules (Basel, Switzerland). 2015 Nov; 20(11):20699-708. doi: 10.3390/molecules201119728. [PMID: 26610445]
  • Yan Yang, Jin-hai Yi, Zhi-fang Huang, Yun-hua Liu, Yu-hong Liu, Yan Chen. [Comparative Study on Volatile Oil Composition of Chuanxiong Rhizoma, Angelicae Sinensis Radix and Ligustici Rhizoma et Radix]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Jun; 38(6):1212-6. doi: . [PMID: 26762063]
  • Zhi-rong Gu, Ya-li Wang, Yu-jing Sun, Jun-xia Dind. [Application of entropy-weight TOPSIS model in synthetical quality evaluation of Angelica sinensis growing in Gansu Province]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Sep; 37(9):1549-53. doi: ". [PMID: 25857151]
  • Ru-Huei Fu, Horng-Jyh Harn, Shih-Ping Liu, Chang-Shi Chen, Wen-Lin Chang, Yue-Mi Chen, Jing-En Huang, Rong-Jhu Li, Sung-Yu Tsai, Huey-Shan Hung, Woei-Cherng Shyu, Shinn-Zong Lin, Yu-Chi Wang. n-butylidenephthalide protects against dopaminergic neuron degeneration and α-synuclein accumulation in Caenorhabditis elegans models of Parkinson's disease. PloS one. 2014; 9(1):e85305. doi: 10.1371/journal.pone.0085305. [PMID: 24416384]
  • Constance Lay Lay Saw, Qing Wu, Zheng-Yuan Su, Hu Wang, Yinhua Yang, Xiaoting Xu, Ying Huang, Tin Oo Khor, Ah-Ng Tony Kong. Effects of natural phytochemicals in Angelica sinensis (Danggui) on Nrf2-mediated gene expression of phase II drug metabolizing enzymes and anti-inflammation. Biopharmaceutics & drug disposition. 2013 Sep; 34(6):303-11. doi: 10.1002/bdd.1846. [PMID: 23640758]
  • Christina E Turi, Susan J Murch. Targeted and untargeted phytochemistry of Ligusticum canbyi: indoleamines, phthalides, antioxidant potential, and use of metabolomics as a hypothesis-generating technique for compound discovery. Planta medica. 2013 Sep; 79(14):1370-9. doi: 10.1055/s-0033-1350618. [PMID: 23877920]
  • Rachel Mata, Sol Cristians, Sonia Escandón-Rivera, Krutzkaya Juárez-Reyes, Isabel Rivero-Cruz. Mexican antidiabetic herbs: valuable sources of inhibitors of α-glucosidases. Journal of natural products. 2013 Mar; 76(3):468-83. doi: 10.1021/np300869g. [PMID: 23398496]
  • Ri-Na Sa, Ya-Li Wang, Shu-Qiang Zhu, Xin-Bo Pan, Ying-Wen Yang, Yu-Jing Sun. [Study on the dynamic variations of Z-ligustilide and n-butylidenephthalide content in essential oil of radix angelicae sinensis from different growth period]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2012 Nov; 35(11):1738-42. doi: . [PMID: 23627080]
  • Jie Yang, Song Yang, Ying-Jin Yuan. Integrated investigation of lipidome and related signaling pathways uncovers molecular mechanisms of tetramethylpyrazine and butylidenephthalide protecting endothelial cells under oxidative stress. Molecular bioSystems. 2012 Jun; 8(6):1789-97. doi: 10.1039/c2mb05510d. [PMID: 22506278]
  • Ru Yan, Nga Ling Ko, Bin Ma, Yun Kau Tam, Ge Lin. Metabolic conversion from co-existing ingredient leading to significant systemic exposure of Z-butylidenephthalide, a minor ingredient in Chuanxiong Rhizoma in rats. Current drug metabolism. 2012 Jun; 13(5):524-34. doi: 10.2174/1389200211209050524. [PMID: 22554277]
  • Ju-Ching Yeh, Ian J Garrard, Chin-Wen Chantal Cho, S W Annie Bligh, Guang-hua Lu, Tai-Ping Fan, Derek Fisher. Bioactivity-guided fractionation of the volatile oil of Angelica sinensis radix designed to preserve the synergistic effects of the mixture followed by identification of the active principles. Journal of chromatography. A. 2012 May; 1236(?):132-8. doi: 10.1016/j.chroma.2012.03.013. [PMID: 22458966]
  • Wei-Shin Liu, Po-Cheng Lin, Li-Fu Chang, Horng-Jyh Harn, David Shiuan, Tzyy-Wen Chiou, Jing-Ren Jeng. Inhibitory effect of n-butylidenephthalide on neointimal hyperplasia in balloon injured rat carotid artery. Phytotherapy research : PTR. 2011 Oct; 25(10):1494-502. doi: 10.1002/ptr.3377. [PMID: 21365711]
  • Song-Hwa Chae, Soon-Il Kim, Seong-Hum Yeon, Si-Woo Lee, Young-Joon Ahn. Adulticidal activity of phthalides identified in Cnidium officinale rhizome to B- and Q-biotypes of Bemisia tabaci. Journal of agricultural and food chemistry. 2011 Aug; 59(15):8193-8. doi: 10.1021/jf201927t. [PMID: 21728333]
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  • Andreas Schinkovitz, Samuel M Pro, Matthew Main, Shao-Nong Chen, Birgit U Jaki, David C Lankin, Guido F Pauli. Dynamic nature of the ligustilide complex. Journal of natural products. 2008 Sep; 71(9):1604-11. doi: 10.1021/np800137n. [PMID: 18781813]
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