Monotropein (BioDeep_00001867519)

Main id: BioDeep_00000000524

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(1S,4aS,7R,7aS)-7-Hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

化学式: C16H22O11 (390.1162)
中文名称: 水晶兰甙, 单糖原
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)(CO)O
InChI: InChI=1S/C16H22O11/c17-3-8-10(19)11(20)12(21)15(26-8)27-14-9-6(1-2-16(9,24)5-18)7(4-25-14)13(22)23/h1-2,4,6,8-12,14-15,17-21,24H,3,5H2,(H,22,23)/t6-,8-,9-,10-,11+,12-,14+,15+,16+/m1/s1

描述信息

Monotropein is an iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a beta-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and hydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer). It has a role as a metabolite and an anti-inflammatory agent. It is a cyclopentapyran, a monocarboxylic acid, an iridoid monoterpenoid, a beta-D-glucoside and a monosaccharide derivative.
Monotropein is a natural product found in Vaccinium, Vaccinium macrocarpon, and other organisms with data available.
See also: Galium aparine whole (part of).
An iridoid monoterpenoid that is 1,4a,7,7a-tetrahydrocyclopenta[c]pyran substituted by a beta-D-glucopyranosyloxy group at position 1, a carboxylic acid group at position 4, and at position 7 by a hydroxy and hydroxymethyl groups respectively (the 1S,4aS,7R,7aS diastereomer).
Monotropein is an iridoid glycoside isolated Morinda officinalis. Monotropein inhibits the expression of inflammatory mediators in dextran sulfate sodium (DSS)-induced colitis mouse model[1].
Monotropein is an iridoid glycoside isolated Morinda officinalis. Monotropein inhibits the expression of inflammatory mediators in dextran sulfate sodium (DSS)-induced colitis mouse model[1].

同义名列表

15 个代谢物同义名

(1S,4aS,7R,7aS)-7-Hydroxy-7-(hydroxymethyl)-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid; CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, (1S-(1.ALPHA.,4A.ALPHA.,7.BETA.,7A.ALPHA.))-; (1S,2S,6S,9R)-9-hydroxy-9-(hydroxymethyl)-2-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,7-diene-5-carboxylic acid; Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, (1S-(1alpha,4aalpha,7beta,7aalpha))-; CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, (1S,4AS,7R,7AS)-; CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(beta-D-GLUCOPYRANOSYLOXY)-1,4A,7,7A-TETRAHYDRO-7-HYDROXY-7-(HYDROXYMETHYL)-, (1S,4AS,7R,7AS)-; (1S,4aS,7R,7aS)-1-(beta-D-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid; (1S,4aS,7R,7aS)-1-(beta-D-glucopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta(c)pyran-4-carboxylic acid; Monotropein, >=98\\% (HPLC); MONOTROPEIN [MI]; UNII-0Y61M84O2T; Monotropeine; Monotropein; 0Y61M84O2T; Monotropein



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

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PharmGKB(0)

85 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
Cytoplasm 14 AKT2, BCL2, CAT, CDK4, CDK6, EGFR, JAK1, KEAP1, MTOR, PINK1, RUNX2, SRARP, TNFSF11, VDR
Peripheral membrane protein 2 GORASP1, MTOR
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 4 BCL2, EGFR, HMOX1, MTOR
Nucleus 14 AKT2, BCL2, CDK4, CDK6, EGFR, GABPA, HMOX1, JAK1, KEAP1, MTOR, PINK1, RUNX2, SRARP, VDR
cytosol 12 AKT2, BCL2, CAT, CDK4, CDK6, HMOX1, JAK1, KEAP1, MTOR, PINK1, RUNX2, VDR
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
centrosome 1 CDK6
nucleoplasm 9 AKT2, CDK4, CDK6, GABPA, HMOX1, KEAP1, MTOR, RUNX2, VDR
RNA polymerase II transcription regulator complex 1 VDR
Cell membrane 2 EGFR, TNFSF11
Cytoplasmic side 3 GORASP1, HMOX1, MTOR
ruffle membrane 2 AKT2, EGFR
Early endosome membrane 1 EGFR
Golgi apparatus membrane 2 GORASP1, MTOR
cell cortex 1 AKT2
cell junction 1 EGFR
cell surface 1 EGFR
glutamatergic synapse 1 EGFR
Golgi apparatus 1 GORASP1
Golgi membrane 3 EGFR, GORASP1, MTOR
growth cone 1 PINK1
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 PINK1
Cytoplasm, cytosol 1 PINK1
Lysosome 1 MTOR
endosome 2 EGFR, JAK1
plasma membrane 4 AKT2, EGFR, JAK1, TNFSF11
Membrane 8 BCL2, CAT, EGFR, HMOX1, JAK1, MTOR, PINK1, TNFSF11
apical plasma membrane 1 EGFR
axon 2 CCK, PINK1
basolateral plasma membrane 1 EGFR
extracellular exosome 2 BMP3, CAT
Lysosome membrane 1 MTOR
endoplasmic reticulum 4 BCL2, HMOX1, KEAP1, PINK1
extracellular space 6 BMP3, CCK, EGFR, HMOX1, IL6, TNFSF11
perinuclear region of cytoplasm 3 EGFR, HMOX1, PINK1
bicellular tight junction 1 CDK4
mitochondrion 3 BCL2, CAT, PINK1
protein-containing complex 3 BCL2, CAT, EGFR
intracellular membrane-bounded organelle 2 AKT2, CAT
Microsome membrane 1 MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 EGFR
Secreted 4 BMP3, CCK, IL6, TNFSF11
extracellular region 5 BMP3, CAT, CCK, IL6, TNFSF11
cytoplasmic side of plasma membrane 1 JAK1
Mitochondrion outer membrane 3 BCL2, MTOR, PINK1
Single-pass membrane protein 2 BCL2, PINK1
mitochondrial outer membrane 4 BCL2, HMOX1, MTOR, PINK1
mitochondrial matrix 1 CAT
transcription regulator complex 2 CDK4, RUNX2
centriolar satellite 1 KEAP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK6
Nucleus membrane 2 BCL2, CDK4
Bcl-2 family protein complex 1 BCL2
nuclear membrane 3 BCL2, CDK4, EGFR
nucleolus 1 CDK4
midbody 1 KEAP1
Early endosome 1 AKT2
Single-pass type II membrane protein 1 TNFSF11
Mitochondrion inner membrane 1 PINK1
Membrane raft 1 EGFR
pore complex 1 BCL2
focal adhesion 3 CAT, EGFR, JAK1
cis-Golgi network 1 GORASP1
Peroxisome 1 CAT
intracellular vesicle 1 EGFR
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
mitochondrial intermembrane space 1 PINK1
ruffle 1 CDK6
receptor complex 2 EGFR, VDR
chromatin 5 CDK4, GABPA, PINK1, RUNX2, VDR
cytoskeleton 2 JAK1, PINK1
actin filament 1 KEAP1
Cul3-RING ubiquitin ligase complex 1 KEAP1
nuclear envelope 1 MTOR
Endomembrane system 2 JAK1, MTOR
cell body 1 PINK1
myelin sheath 1 BCL2
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 1 IL6
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
Single-pass type IV membrane protein 1 HMOX1
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
clathrin-coated endocytic vesicle membrane 1 EGFR
extrinsic component of cytoplasmic side of plasma membrane 1 JAK1
Lewy body 1 PINK1
Cytoplasmic vesicle, phagosome 1 MTOR
cyclin-dependent protein kinase holoenzyme complex 2 CDK4, CDK6
astrocyte projection 1 PINK1
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
catalase complex 1 CAT
inclusion body 1 KEAP1
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
cyclin D1-CDK4 complex 1 CDK4
cyclin D2-CDK4 complex 1 CDK4
cyclin D3-CDK4 complex 1 CDK4
cyclin D1-CDK6 complex 1 CDK6
cyclin D3-CDK6 complex 1 CDK6
cyclin D2-CDK6 complex 1 CDK6


文献列表

  • Quan Gao, Lin Li, Qi-Man Zhang, Qin-Song Sheng, Ji-Liang Zhang, Li-Jun Jin, Rui-Yan Shang. Monotropein Induced Apoptosis and Suppressed Cell Cycle Progression in Colorectal Cancer Cells. Chinese journal of integrative medicine. 2023 Sep; ?(?):. doi: 10.1007/s11655-023-3710-4. [PMID: 37750986]
  • Shitian Zhao, Liqiang Guo, Wei Cui, Yongjian Zhao, Jing Wang, Kanghui Sun, Hong Zhang, Yueli Sun, Dongfeng Zhao, Xiaohui Hu, Ziyu Huang, Sheng Lu, Yongjun Wang, Xinhua Liu, Weian Zhang, Bing Shu. Monotropein Protects Mesenchymal Stem Cells from Lipopolysaccharide-Induced Impairments and Promotes Fracture Healing in an Ovariectomized Mouse Model. Calcified tissue international. 2023 Sep; ?(?):. doi: 10.1007/s00223-023-01130-y. [PMID: 37747519]
  • Qi Zhang, Sijing Hu, Yuqiong He, Zile Song, Yi Shen, Zihui Zhao, Quanlong Zhang, Luping Qin, Qiaoyan Zhang. Monotropein Protects against Inflammatory Bone Loss and Suppresses Osteoclast Formation and Bone Resorption by Inhibiting NFATc1 via NF-κB and Akt/GSK-3β Pathway. Nutrients. 2022 Sep; 14(19):. doi: 10.3390/nu14193978. [PMID: 36235631]
  • Yuping Zhang, Yonger Chen, Baixue Li, Ping Ding, Daxiang Jin, Shaozhen Hou, Xiaochun Cai, Xiujie Sheng. The effect of monotropein on alleviating cisplatin-induced acute kidney injury by inhibiting oxidative damage, inflammation and apoptosis. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Sep; 129(?):110408. doi: 10.1016/j.biopha.2020.110408. [PMID: 32574971]
  • Yao Shi, Xiao-Yan Liu, Yi-Ping Jiang, Jia-Bao Zhang, Qiao-Yan Zhang, Na-Ni Wang, Hai-Liang Xin. Monotropein attenuates oxidative stress via Akt/mTOR-mediated autophagy in osteoblast cells. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2020 Jan; 121(?):109566. doi: 10.1016/j.biopha.2019.109566. [PMID: 31698268]
  • Keshab Kumar Karna, Bo Ram Choi, Jae Hyung You, Yu Seob Shin, Wan Shou Cui, Sung Won Lee, Ji Hoon Kim, Chul Young Kim, Hye Kyung Kim, Jong Kwan Park. The ameliorative effect of monotropein, astragalin, and spiraeoside on oxidative stress, endoplasmic reticulum stress, and mitochondrial signaling pathway in varicocelized rats. BMC complementary and alternative medicine. 2019 Nov; 19(1):333. doi: 10.1186/s12906-019-2736-9. [PMID: 31771569]
  • Yi Shen, Qi Zhang, Yan-Bin Wu, Yu-Qiong He, Ting Han, Jian-Hua Zhang, Liang Zhao, Hsien-Yeh Hsu, Hong-Tao Song, Bing Lin, Hai-Liang Xin, Yun-Peng Qi, Qiao-Yan Zhang. Pharmacokinetics and tissue distribution of monotropein and deacetyl asperulosidic acid after oral administration of extracts from Morinda officinalis root in rats. BMC complementary and alternative medicine. 2018 Oct; 18(1):288. doi: 10.1186/s12906-018-2351-1. [PMID: 30355303]
  • Yu-Qiong He, Hua Yang, Yi Shen, Jian-Hua Zhang, Zhi-Guo Zhang, Lin-Lin Liu, Hong-Tao Song, Bin Lin, Hsien-Yeh Hsu, Lu-Ping Qin, Ting Han, Hai-Liang Xin, Qiao-Yan Zhang. Monotropein attenuates ovariectomy and LPS-induced bone loss in mice and decreases inflammatory impairment on osteoblast through blocking activation of NF-κB pathway. Chemico-biological interactions. 2018 Aug; 291(?):128-136. doi: 10.1016/j.cbi.2018.06.015. [PMID: 29908987]
  • Chenggui Wang, Cong Mao, Yiting Lou, Jianxiang Xu, Qingqing Wang, Zengjie Zhang, Qian Tang, Xiaolei Zhang, Huazi Xu, Yongzeng Feng. Monotropein promotes angiogenesis and inhibits oxidative stress-induced autophagy in endothelial progenitor cells to accelerate wound healing. Journal of cellular and molecular medicine. 2018 03; 22(3):1583-1600. doi: 10.1111/jcmm.13434. [PMID: 29278309]
  • Xiliang Yang, Qingyun Peng, Qian Liu, Jie Hu, Zhipeng Tang, Lianjie Cui, Zonghao Lin, Bing Xu, Kuojian Lu, Fang Yang, Zhizheng Sheng, Qiong Yuan, Song Liu, Jiuliang Zhang, Xuefeng Zhou. Antioxidant activity against H2O2-induced cytotoxicity of the ethanol extract and compounds from Pyrola decorate leaves. Pharmaceutical biology. 2017 Dec; 55(1):1843-1848. doi: 10.1080/13880209.2017.1333126. [PMID: 28571528]
  • Courtney P Leisner, Mohamed O Kamileen, Megan E Conway, Sarah E O'Connor, C Robin Buell. Differential iridoid production as revealed by a diversity panel of 84 cultivated and wild blueberry species. PloS one. 2017; 12(6):e0179417. doi: 10.1371/journal.pone.0179417. [PMID: 28609455]
  • Fang-Bing Zhu, Jian-Yue Wang, Ying-Liang Zhang, Yun-Gen Hu, Zhen-Shuang Yue, Lin-Ru Zeng, Wen-Jie Zheng, Qiao Hou, Shi-Gui Yan, Ren-Fu Quan. Mechanisms underlying the antiapoptotic and anti-inflammatory effects of monotropein in hydrogen peroxide-treated osteoblasts. Molecular medicine reports. 2016 Dec; 14(6):5377-5384. doi: 10.3892/mmr.2016.5908. [PMID: 27840925]
  • Zhiguo Zhang, Qiaoyan Zhang, Hua Yang, Wei Liu, Naidan Zhang, Luping Qin, Hailiang Xin. Monotropein isolated from the roots of Morinda officinalis increases osteoblastic bone formation and prevents bone loss in ovariectomized mice. Fitoterapia. 2016 Apr; 110(?):166-72. doi: 10.1016/j.fitote.2016.03.013. [PMID: 26996879]
  • Feng Wang, Longhuo Wu, Linfu Li, Siyi Chen. Monotropein exerts protective effects against IL-1β-induced apoptosis and catabolic responses on osteoarthritis chondrocytes. International immunopharmacology. 2014 Dec; 23(2):575-80. doi: 10.1016/j.intimp.2014.10.007. [PMID: 25466264]
  • Ji-Sun Shin, Kyung-Jin Yun, Kyung-Sook Chung, Kyeong-Hwa Seo, Hee-Juhn Park, Young-Wuk Cho, Nam-In Baek, Daesik Jang, Kyung-Tae Lee. Monotropein isolated from the roots of Morinda officinalis ameliorates proinflammatory mediators in RAW 264.7 macrophages and dextran sulfate sodium (DSS)-induced colitis via NF-κB inactivation. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Mar; 53(?):263-71. doi: 10.1016/j.fct.2012.12.013. [PMID: 23261679]
  • Olga Tzakou, Philippos Mylonas, Constantinos Vagias, Panos V Petrakis. Iridoid glucosides with insecticidal activity from Galium melanantherum. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2007 Jul; 62(7-8):597-602. doi: 10.1515/znc-2007-7-823. [PMID: 17913079]
  • Ji-yin Xu, Ying-jiao Liang, Ping Ding. [Determination of monotropein in Radix Morindae from different processed products by HPLC]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Jan; 30(1):20-2. doi: . [PMID: 17539297]
  • Jongwon Choi, Kyung-Tae Lee, Moo-Young Choi, Jung-Hwan Nam, Hyun-Ju Jung, Sun-Kyu Park, Hee-Juhn Park. Antinociceptive anti-inflammatory effect of Monotropein isolated from the root of Morinda officinalis. Biological & pharmaceutical bulletin. 2005 Oct; 28(10):1915-8. doi: 10.1248/bpb.28.1915. [PMID: 16204945]
  • Ju Sun Kim, Sang Hee Shim, Yong Nan Xu, Sam Sik Kang, Kun Ho Son, Hyeun Wook Chang, Hyun Pyo Kim, KiHwan Bae. Phenolic glycosides from Pyrola japonica. Chemical & pharmaceutical bulletin. 2004 Jun; 52(6):714-7. doi: 10.1248/cpb.52.714. [PMID: 15187393]
  • Sui-Kiong Ling, Akiko Komorita, Takashi Tanaka, Toshihiro Fujioka, Kunihide Mihashi, Isao Kouno. Sulfur-containing bis-iridoid glucosides and iridoid glucosides from Saprosmas cortechinii. Journal of natural products. 2002 May; 65(5):656-60. doi: 10.1021/np010479o. [PMID: 12027736]