Loliolide (BioDeep_00000227318)

 

Secondary id: BioDeep_00000404892, BioDeep_00000405173

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

化学式: C11H16O3 (196.1099)
中文名称: 地芰普内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 85.64%

分子结构信息

SMILES: CC1(C)CC(O)CC2(C)OC(=O)C=C12
InChI: InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1

描述信息

Loliolide, also known as (3s5r)-loliolide, is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Loliolide is soluble (in water) and an extremely weak acidic compound (based on its pKa). Loliolide can be found in sunflower, tea, and wakame, which makes loliolide a potential biomarker for the consumption of these food products.

同义名列表

11 个代谢物同义名

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one; (6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one; 1,3-Dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone; (6S,7alphaR)-Loliolide; (3S5R)-Loliolide; Digiprolactone; (-)-Loliolide; loliolide; Caulilide; Calendin; Loliolid



数据库引用编号

11 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)

545 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。

亚细胞结构定位 关联基因列表


文献列表

  • Lei-Lei Li, Zheng Li, Yonggen Lou, Scott J Meiners, Chui-Hua Kong. (-)-Loliolide is a general signal of plant stress that activates jasmonate-related responses. The New phytologist. 2023 06; 238(5):2099-2112. doi: 10.1111/nph.18644. [PMID: 36444519]
  • Feng-Li Li, Xin Chen, Hui-Min Luo, Scott J Meiners, Chui-Hua Kong. Root-secreted (-)-loliolide modulates both belowground defense and aboveground flowering in Arabidopsis and tobacco. Journal of experimental botany. 2023 02; 74(3):964-975. doi: 10.1093/jxb/erac439. [PMID: 36342376]
  • Lei Wang, Hyun-Soo Kim, Jun-Geon Je, Xiaoting Fu, Caoxing Huang, Ginnae Ahn, Jae-Young Oh, K K Asanka Sanjeewa, Jiachao Xu, Xin Gao, In-Kyu Yeo, You-Jin Jeon. In Vitro and In Vivo Photoprotective Effects of (-)-Loliode Isolated from the Brown Seaweed, Sargassum horneri. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26226898. [PMID: 34833989]
  • Hao Chi, Xia Qi, Xiaohui Wang, Ying Wang, Xihong Han, Jiao Wang, Hongwei Wang. Preparative separation and purification of loliolide and epiloliolide from Ascophyllum nodosum using amine-based microporous organic polymer for solid phase extraction coupled with macroporous resin and prep-HPLC. Analytical methods : advancing methods and applications. 2021 Apr; 13(16):1939-1944. doi: 10.1039/d1ay00186h. [PMID: 33913944]
  • Jun Gu Kim, Jin Woo Lee, Thi Phuong Linh Le, Jae Sang Han, Yong Beom Cho, Haeun Kwon, Dongho Lee, Mi Kyeong Lee, Bang Yeon Hwang. Sesquiterpenoids from Chrysanthemum indicum with Inhibitory Effects on NO Production. Journal of natural products. 2021 03; 84(3):562-569. doi: 10.1021/acs.jnatprod.0c01121. [PMID: 33667099]
  • Hyo-Geun Lee, Hyun-Soo Kim, Jun-Geon Je, Jin Hwang, K K Asanka Sanjeewa, Dae-Sung Lee, Kyung-Mo Song, Yun-Sang Choi, Min-Cheol Kang, You-Jin Jeon. Lipid Inhibitory Effect of (-)-loliolide Isolated from Sargassum horneri in 3T3-L1 Adipocytes: Inhibitory Mechanism of Adipose-Specific Proteins. Marine drugs. 2021 Feb; 19(2):. doi: 10.3390/md19020096. [PMID: 33567534]
  • Abdul Rahim, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, Masuo Goto, Chin-Ho Chen, Gemini Alam, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto. Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata. Journal of natural products. 2020 10; 83(10):2931-2939. doi: 10.1021/acs.jnatprod.0c00454. [PMID: 32946697]
  • Lei-Lei Li, Huan-Huan Zhao, Chui-Hua Kong. (-)-Loliolide, the most ubiquitous lactone, is involved in barnyardgrass-induced rice allelopathy. Journal of experimental botany. 2020 02; 71(4):1540-1550. doi: 10.1093/jxb/erz497. [PMID: 31677347]
  • Sun Young Kim, Joo Young Lee, Changho Jhin, Ji Min Shin, Myungsuk Kim, Hong Ruyl Ahn, Gyhye Yoo, Yang-Ju Son, Sang Hoon Jung, Chu Won Nho. Reduction of Hepatic Lipogenesis by Loliolide and Pinoresinol from Lysimachia vulgaris via Degrading Liver X Receptors. Journal of agricultural and food chemistry. 2019 Nov; 67(45):12419-12427. doi: 10.1021/acs.jafc.9b01488. [PMID: 31610126]
  • Mika Murata, Yusuke Nakai, Kei Kawazu, Masumi Ishizaka, Hideyuki Kajiwara, Hiroshi Abe, Kasumi Takeuchi, Yuki Ichinose, Ichiro Mitsuhara, Atsushi Mochizuki, Shigemi Seo. Loliolide, a Carotenoid Metabolite, Is a Potential Endogenous Inducer of Herbivore Resistance. Plant physiology. 2019 04; 179(4):1822-1833. doi: 10.1104/pp.18.00837. [PMID: 30700538]
  • 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]
  • Janggyoo Choi, Kee Dong Yoon, Jinwoong Kim. Chemical constituents from Taraxacum officinale and their α-glucosidase inhibitory activities. Bioorganic & medicinal chemistry letters. 2018 02; 28(3):476-481. doi: 10.1016/j.bmcl.2017.12.014. [PMID: 29254644]
  • Chueh-Yao Chung, Ching-Hsuan Liu, Thierry Burnouf, Guey-Horng Wang, Shun-Pang Chang, Alagie Jassey, Chen-Jei Tai, Cheng-Jeng Tai, Ching-Jang Huang, Christopher D Richardson, Ming-Hong Yen, Chun-Ching Lin, Liang-Tzung Lin. Activity-based and fraction-guided analysis of Phyllanthus urinaria identifies loliolide as a potent inhibitor of hepatitis C virus entry. Antiviral research. 2016 06; 130(?):58-68. doi: 10.1016/j.antiviral.2016.03.012. [PMID: 27012176]
  • Lin Ni, Xing Zhou, Jie Ma, Xiao-Mei Zhang, Chuang-Jun Li, Li Li, Da-Jian Yang, Yang-Yang Shao, Si-Bai Zhou, Tian-Tai Zhang, Dong-Ming Zhang. Wilfordonols A-D: four new norsesquiterpenes from the leaves of Tripterygium wilfordii. Journal of Asian natural products research. 2015; 17(6):615-24. doi: 10.1080/10286020.2015.1054380. [PMID: 26096035]
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  • Nina Corlay, Leen Delang, Emmanuelle Girard-Valenciennes, Johan Neyts, Patricia Clerc, Jacqueline Smadja, Françoise Guéritte, Pieter Leyssen, Marc Litaudon. Tigliane diterpenes from Croton mauritianus as inhibitors of chikungunya virus replication. Fitoterapia. 2014 Sep; 97(?):87-91. doi: 10.1016/j.fitote.2014.05.015. [PMID: 24879904]
  • Bin Zhou, Chui-Hua Kong, Yong-Hua Li, Peng Wang, Xiao-Hua Xu. Crabgrass (Digitaria sanguinalis) allelochemicals that interfere with crop growth and the soil microbial community. Journal of agricultural and food chemistry. 2013 Jun; 61(22):5310-7. doi: 10.1021/jf401605g. [PMID: 23678893]
  • Attila Hunyadi, Katalin Veres, Balazs Danko, Zoltan Kele, Edit Weber, Anasztazia Hetenyi, Istvan Zupko, Tusty-Jiuan Hsieh. In vitro anti-diabetic activity and chemical characterization of an apolar fraction of Morus alba leaf water extract. Phytotherapy research : PTR. 2013 Jun; 27(6):847-51. doi: 10.1002/ptr.4803. [PMID: 22899346]
  • Catherine Argyropoulou, Anastasia Karioti, Helen Skaltsa. Minor labdane diterpenes from Marrubium thessalum. Chemistry & biodiversity. 2011 Oct; 8(10):1880-90. doi: 10.1002/cbdv.201000215. [PMID: 22006716]
  • Consolacion Y Ragasa, Roderick D De Luna, Joy G Hofilena. Antimicrobial terpenoids from Pterocarpus indicus. Natural product research. 2005 Jun; 19(4):305-9. doi: 10.1080/14786410410001704822. [PMID: 15938134]
  • M Takasaki, H Tokuda, H Nishino, T Konoshima. Cancer chemopreventive agents (antitumor-promoters) from Ajuga decumbens. Journal of natural products. 1999 Jul; 62(7):972-5. doi: 10.1021/np990033w. [PMID: 10425119]