Yamogenintetroside B (BioDeep_00000000601)

 

Secondary id: BioDeep_00000267998, BioDeep_00000618633, BioDeep_00001867530

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


2-[4-(16-{[4-hydroxy-6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

化学式: C52H86O22 (1062.561)
中文名称: 甲基原薯蓣皂苷, 甲基原薯蓣皂甙
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1C2C(CC3C2(CCC4C3CC=C5C4(CCC(C5)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)C)O)O)O)O)OC8C(C(C(C(O8)C)O)O)O)C)C)OC1(CCC(C)COC9C(C(C(C(O9)CO)O)O)O)OC
InChI: InChI=1S/C52H86O22/c1-21(20-66-46-40(61)39(60)36(57)31(18-53)70-46)10-15-52(65-7)22(2)33-30(74-52)17-29-27-9-8-25-16-26(11-13-50(25,5)28(27)12-14-51(29,33)6)69-49-45(73-48-42(63)38(59)35(56)24(4)68-48)43(64)44(32(19-54)71-49)72-47-41(62)37(58)34(55)23(3)67-47/h8,21-24,26-49,53-64H,9-20H2,1-7H3

描述信息

Methylprotodioscin is a steroid saponin.
Methylprotodioscin is a natural product found in Dracaena draco, Smilax menispermoidea, and other organisms with data available.
Methylprotodioscin is found in herbs and spices. Methylprotodioscin is isolated from seeds of Trigonella caerulea (sweet trefoil) and Asparagus officinalis (asparagus).
Methyl protodioscin(NSC-698790) is a furostanol bisglycoside with antitumor properties; shows to reduce proliferation, cause cell cycle arrest. IC50 value: Target: in vitro: MPD showed growth inhibitory effects in A549 cells in a dose- and time-dependent manner. The significant G2/M cell cycle arrest and apoptotic effect were also seen in A549 cells treated with MPD. MPD-induced apoptosis was accompanied by a significant reduction of mitochondrial membrane potential, release of mitochondrial cytochrome c to cytosol, activation of caspase-3, downregulation of Bcl-2, p-Bad, and upregulation of Bax [1]. In THP-1 macrophages, MPD increases levels of ABCA1 mRNA and protein in dose- and time-dependent manners, and apoA-1-mediated cholesterol efflux. MPD also decreases the gene expressions of HMGCR, FAS and ACC for cholesterol and fatty acid synthesis [2].
Methyl protodioscin(NSC-698790) is a furostanol bisglycoside with antitumor properties; shows to reduce proliferation, cause cell cycle arrest. IC50 value: Target: in vitro: MPD showed growth inhibitory effects in A549 cells in a dose- and time-dependent manner. The significant G2/M cell cycle arrest and apoptotic effect were also seen in A549 cells treated with MPD. MPD-induced apoptosis was accompanied by a significant reduction of mitochondrial membrane potential, release of mitochondrial cytochrome c to cytosol, activation of caspase-3, downregulation of Bcl-2, p-Bad, and upregulation of Bax [1]. In THP-1 macrophages, MPD increases levels of ABCA1 mRNA and protein in dose- and time-dependent manners, and apoA-1-mediated cholesterol efflux. MPD also decreases the gene expressions of HMGCR, FAS and ACC for cholesterol and fatty acid synthesis [2].

同义名列表

22 个代谢物同义名

2-[4-(16-{[4-hydroxy-6-(hydroxymethyl)-3,5-bis[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl)-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; .BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-26-(.BETA.-D-GLUCOPYRANOSYLOXY)-22-METHOXYFUROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-; (3.BETA.,22.ALPHA.,25R)-26-(.BETA.-D-GLUCOPYRANOSYLOXY)-22-METHOXYFUROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE; beta-D-Glucopyranoside, (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-methoxyfurost-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-; 3-O-(alpha-l-rhamnopyranosyl-(1-2)-(alpha-L-rhamnopyranosyl-(1-4))-beta-D-glucopyranosyl)-26-O-(beta-D-glucopyranosyl)-22-methoxy-(25R)-furost-5-ene-3beta,26-diol; 3.BETA.,26-DIHYDROXY-22.ALPHA.-METHOXYFUROST-5-ENE 3-O-.BETA.-CHACOTRIOSIDE 26-O-.BETA.-D-GLUCOPYRANOSIDE; 3-O-(Rhaa1-4(Rhaa1-2)Glcb)-26-O-(Glcb)-22-methoxy-(25R)-furost-5-ene-3beta,26-diol; NSC-698790;Smilax saponin B; 22-O-METHYLPROTODIOSCIN; 22-METHOXYLPROTODIOSCIN; Methionine ethyl ester; Yamogenintetroside B; methyl protodioscin; Ethyl DL-methionate; Methylprotodioscin; Ethyl L-methionate; UNII-1VJB6VV6IA; 1VJB6VV6IA; MPD cpd; NSC-698790; Smilax saponin B; Methylprotodioscin



数据库引用编号

27 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)

86 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 16 AKAP12, ANXA5, BCL2, CASP3, CASP9, CCNB1, FASN, FOXO1, MAPK14, MAPK8, MYC, NOS3, NR1H2, PCSK9, SREBF1, SREBF2
Peripheral membrane protein 1 ANXA5
Endoplasmic reticulum membrane 5 ABCA1, BCL2, HMGCR, SREBF1, SREBF2
Nucleus 12 BCL2, CASP3, CASP9, CCNB1, FOXO1, MAPK14, MAPK8, MYC, NOS3, NR1H2, SREBF1, SREBF2
cytosol 14 AKAP12, ANXA5, BCL2, CASP3, CASP9, CCNB1, FASN, FOXO1, MAPK14, MAPK8, NOS3, NR1H2, SREBF1, SREBF2
phagocytic vesicle 1 ABCA1
centrosome 1 CCNB1
nucleoplasm 10 CASP3, CCNB1, FOXO1, MAPK14, MAPK8, MYC, NOS3, NR1H2, SREBF1, SREBF2
RNA polymerase II transcription regulator complex 1 NR1H2
Cell membrane 2 ABCA1, TNF
Lipid-anchor 1 AKAP12
Multi-pass membrane protein 4 ABCA1, HMGCR, SREBF1, SREBF2
Golgi apparatus membrane 2 SREBF1, SREBF2
Synapse 1 MAPK8
cell cortex 1 AKAP12
cell surface 2 PCSK9, TNF
glutamatergic synapse 2 CASP3, MAPK14
Golgi apparatus 4 ABCA1, FASN, NOS3, PCSK9
Golgi membrane 3 NOS3, SREBF1, SREBF2
lysosomal membrane 1 PCSK9
neuronal cell body 3 AKAP12, CASP3, TNF
sarcolemma 1 ANXA5
Lysosome 1 PCSK9
endosome 2 ABCA1, PCSK9
plasma membrane 6 ABCA1, AKAP12, FASN, NOS3, PCSK9, TNF
Membrane 8 ABCA1, AKAP12, ANXA5, BCL2, CCNB1, FASN, HMGCR, MYC
axon 1 MAPK8
basolateral plasma membrane 1 ABCA1
caveola 1 NOS3
extracellular exosome 2 ANXA5, FASN
endoplasmic reticulum 5 BCL2, HMGCR, PCSK9, SREBF1, SREBF2
extracellular space 2 PCSK9, TNF
perinuclear region of cytoplasm 3 ABCA1, NOS3, PCSK9
Schaffer collateral - CA1 synapse 1 AKAP12
mitochondrion 4 BCL2, CASP9, FOXO1, MAPK14
protein-containing complex 4 BCL2, CASP9, MYC, SREBF1
intracellular membrane-bounded organelle 2 ABCA1, SREBF2
postsynaptic density 1 CASP3
Secreted 1 PCSK9
extracellular region 4 ANXA5, MAPK14, PCSK9, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CCNB1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 3 ABCA1, ANXA5, TNF
nucleolus 1 MYC
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Early endosome 1 PCSK9
COPII-coated ER to Golgi transport vesicle 1 PCSK9
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 ABCA1, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 AKAP12
focal adhesion 2 AKAP12, ANXA5
intracellular vesicle 1 ABCA1
peroxisomal membrane 1 HMGCR
collagen-containing extracellular matrix 1 ANXA5
nuclear speck 1 MAPK14
Late endosome 1 PCSK9
Zymogen granule membrane 1 ANXA5
chromatin 5 FOXO1, MYC, NR1H2, SREBF1, SREBF2
phagocytic cup 1 TNF
cytoskeleton 2 AKAP12, NOS3
Nucleus, nucleolus 1 MYC
spindle pole 2 CCNB1, MAPK14
Cytoplasm, cell cortex 1 AKAP12
nuclear envelope 2 MYC, SREBF1
Cytoplasmic vesicle membrane 1 SREBF1
Nucleus, nucleoplasm 1 MYC
Melanosome 1 FASN
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
myelin sheath 1 BCL2
Peroxisome membrane 1 HMGCR
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 1 PCSK9
endocytic vesicle membrane 1 NOS3
endocytic vesicle 1 ABCA1
RNA polymerase II transcription repressor complex 1 MYC
ER to Golgi transport vesicle membrane 2 SREBF1, SREBF2
apoptosome 1 CASP9
outer kinetochore 1 CCNB1
vesicle membrane 1 ANXA5
endolysosome membrane 1 PCSK9
basal dendrite 1 MAPK8
SREBP-SCAP-Insig complex 1 SREBF2
death-inducing signaling complex 1 CASP3
Rough endoplasmic reticulum 1 MYC
extrinsic component of external side of plasma membrane 1 PCSK9
Cytoplasmic vesicle, COPII-coated vesicle membrane 2 SREBF1, SREBF2
Myc-Max complex 1 MYC
PCSK9-LDLR complex 1 PCSK9
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cyclin B1-CDK1 complex 1 CCNB1
PCSK9-AnxA2 complex 1 PCSK9
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
glycogen granule 1 FASN
caspase complex 1 CASP9
[Sterol regulatory element-binding protein 2]: Endoplasmic reticulum membrane 1 SREBF2
[Processed sterol regulatory element-binding protein 2]: Nucleus 1 SREBF2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
nucleoplasmic reticulum 1 MYC


文献列表

  • Min Luo, Zongren Hu, Ziyu Liu, Xiaoying Tian, Jisong Chen, Jichang Yang, Lumei Liu, Chengxiong Lin, Dian Li, Qinghu He. Methyl protodioscin reduces c-Myc to ameliorate diabetes mellitus erectile dysfunction via downregulation of AKAP12. Diabetes research and clinical practice. 2023 Nov; ?(?):111012. doi: 10.1016/j.diabres.2023.111012. [PMID: 37967586]
  • Jie Chen, Puyan Qin, Zhanxia Tao, Weijian Ding, Yunlong Yao, Weifang Xu, Dengke Yin, Song Tan. Anticancer Activity of Methyl Protodioscin against Prostate Cancer by Modulation of Cholesterol-Associated MAPK Signaling Pathway via FOXO1 Induction. Biological & pharmaceutical bulletin. 2023; 46(4):574-585. doi: 10.1248/bpb.b22-00682. [PMID: 37005301]
  • Zhi Dai, Hui Liu, Bei Wang, Dong Yang, Yan-Yan Zhu, Huan Yan, Pei-Feng Zhu, Ya-Ping Liu, Hui-Cheng Chen, Yun-Li Zhao, Li-Xing Zhao, Xu-Dong Zhao, Hai-Yang Liu, Xiao-Dong Luo. Structures/cytotoxicity/selectivity relationship of natural steroidal saponins against GSCs and primary mechanism of tribulosaponin A. European journal of medicinal chemistry. 2021 Jan; 210(?):113068. doi: 10.1016/j.ejmech.2020.113068. [PMID: 33310292]
  • Yanan Gai, Yingshuo Li, Zenglai Xu, Jian Chen. Pseudoprotodioscin inhibits SREBPs and microRNA 33a/b levels and reduces the gene expression regarding the synthesis of cholesterol and triglycerides. Fitoterapia. 2019 Nov; 139(?):104393. doi: 10.1016/j.fitote.2019.104393. [PMID: 31669721]
  • Rajni Sharma, Linda Gatchie, Ibidapo S Williams, Shreyans K Jain, Ram A Vishwakarma, Bhabatosh Chaudhuri, Sandip B Bharate. Glycyrrhiza glabra extract and quercetin reverses cisplatin resistance in triple-negative MDA-MB-468 breast cancer cells via inhibition of cytochrome P450 1B1 enzyme. Bioorganic & medicinal chemistry letters. 2017 12; 27(24):5400-5403. doi: 10.1016/j.bmcl.2017.11.013. [PMID: 29150398]
  • Shun-Cheng Tseng, Tai-Shan Shen, Chia-Chieh Wu, Ing-Lin Chang, Hsin-Yao Chen, Chen-Pu Hsieh, Chun-Hsiang Cheng, Chiu-Liang Chen. Methyl Protodioscin Induces Apoptosis in Human Osteosarcoma Cells by Caspase-Dependent and MAPK Signaling Pathways. Journal of agricultural and food chemistry. 2017 Apr; 65(13):2670-2676. doi: 10.1021/acs.jafc.6b04800. [PMID: 28301149]
  • Yun-Lung Chung, Chun-Hsu Pan, Charles C-N Wang, Kai-Cheng Hsu, Ming-Jyh Sheu, Hai-Feng Chen, Chieh-Hsi Wu. Methyl Protodioscin, a Steroidal Saponin, Inhibits Neointima Formation in Vitro and in Vivo. Journal of natural products. 2016 06; 79(6):1635-44. doi: 10.1021/acs.jnatprod.6b00217. [PMID: 27227546]
  • Hyun Jae Lee, Jin Sung Park, Yong Pill Yoon, Ye Jin Shin, Sang Kook Lee, Yeong Shik Kim, Jang-Hee Hong, Kun Ho Son, Choong Jae Lee. Dioscin and methylprotodioscin isolated from the root of Asparagus cochinchinensis suppressed the gene expression and production of airway MUC5AC mucin induced by phorbol ester and growth factor. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2015 May; 22(5):568-72. doi: 10.1016/j.phymed.2015.03.009. [PMID: 25981923]
  • Weilie Ma, Hang Ding, Xiaohua Gong, Zhen Liu, Yalin Lin, Zhizhen Zhang, Guorong Lin. Methyl protodioscin increases ABCA1 expression and cholesterol efflux while inhibiting gene expressions for synthesis of cholesterol and triglycerides by suppressing SREBP transcription and microRNA 33a/b levels. Atherosclerosis. 2015 Apr; 239(2):566-70. doi: 10.1016/j.atherosclerosis.2015.02.034. [PMID: 25733328]
  • X Cao, Z Yao, M Shao, H Chen, W Ye, X Yao. Pharmacokinetics of methyl protodioscin in rats. Die Pharmazie. 2010 May; 65(5):359-62. doi: . [PMID: 20503929]
  • Zong Ning, Yi-kui Li, Yan Zhou. [Effect and mechanism of methyl protodioscin in protecting cardiomyocytes against anoxia/reoxygenation injury]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2010 Apr; 30(4):407-9. doi: . [PMID: 20669680]
  • Zhi-Hong Yao, Xiu-Zhen Cao, Meng Shao, Yu-Ming Pan, Wen-Cai Ye, Xin-Sheng Yao. [Determination of plasma protein binding rate of methyl protodioscin with ultrafiltration]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Jun; 33(11):1291-4. doi: NULL. [PMID: 18831210]
  • Xiuzhen Cao, Zhihong Yao, Haifeng Chen, Yi Dai, Pinghua Sun, Wencai Ye, Xinsheng Yao. Development and validation of a liquid chromatography/tandem mass spectrometry assay for the quantification of methyl protodioscin in rat plasma: application to a pharmacokinetic study. Biomedical chromatography : BMC. 2008 Apr; 22(4):408-13. doi: 10.1002/bmc.948. [PMID: 18004744]
  • Shuhai Lin, Dongmei Wang, Depo Yang, Junhua Yao, Yao Tong, Jianping Chen. Characterization of steroidal saponins in crude extract from Dioscorea nipponica Makino by liquid chromatography tandem multi-stage mass spectrometry. Analytica chimica acta. 2007 Sep; 599(1):98-106. doi: 10.1016/j.aca.2007.07.070. [PMID: 17765069]
  • Guanghui Wang, Haifeng Chen, Minghui Huang, Naili Wang, Jinchao Zhang, Yaou Zhang, Ganrong Bai, Wang-Fun Fong, Mengsu Yang, Xinsheng Yao. Methyl protodioscin induces G2/M cell cycle arrest and apoptosis in HepG2 liver cancer cells. Cancer letters. 2006 Sep; 241(1):102-9. doi: 10.1016/j.canlet.2005.10.050. [PMID: 16458429]
  • Xiangjiu He, Aimin Qiao, Xinluan Wang, Bo Liu, Miaomiao Jiang, Lina Su, Xinsheng Yao. Structural identification of methyl protodioscin metabolites in rats' urine and their antiproliferative activities against human tumor cell lines. Steroids. 2006 Sep; 71(9):828-33. doi: 10.1016/j.steroids.2006.05.013. [PMID: 16797625]
  • Xiangjiu He, Bo Liu, Guanghui Wang, Xinluan Wang, Lina Su, Gexia Qu, Xinsheng Yao. Microbial metabolism of methyl protodioscin by Aspergillus niger culture--a new androstenedione producing way from steroid. The Journal of steroid biochemistry and molecular biology. 2006 Jul; 100(1-3):87-94. doi: 10.1016/j.jsbmb.2006.03.007. [PMID: 16713252]
  • Wei-Xing Yang, Hong-Yu Huang, Yong-Jiang Wang, Zhi-Yan Jia, Lin-Lin Li. [Study on chemical constituents in total saponin from Trigonella foenum-graecum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2005 Sep; 30(18):1428-30. doi: . [PMID: 16381462]
  • Jun Yin, Yasuhiro Tezuka, Kyoji Kouda, Quan Le Tran, Tatsuro Miyahara, Yingjie Chen, Shigetoshi Kadota. In vivo antiosteoporotic activity of a fraction of Dioscorea spongiosa and its constituent, 22-O-methylprotodioscin. Planta medica. 2004 Mar; 70(3):220-6. doi: 10.1055/s-2004-815538. [PMID: 15114498]
  • Antonio G González, Juan C Hernández, Francisco León, Juan I Padrón, Francisco Estévez, José Quintana, Jaime Bermejo. Steroidal saponins from the bark of Dracaena draco and their cytotoxic activities. Journal of natural products. 2003 Jun; 66(6):793-8. doi: 10.1021/np020517j. [PMID: 12828464]