Sugiol (BioDeep_00000000827)

 

Secondary id: BioDeep_00000021966

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


9(1H)-Phenanthrenone, 2,3,4,4a,10,10a-hexahydro-6-hydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-, (4aS-trans)-

  化学式: C20H28O2 (300.2089)
中文名称: 柳杉酚
  谱图信息: 最多检出来源 Viridiplantae(plant) 10.79%

分子结构信息

SMILES: CC(C)C1=C(C=C2C(=C1)C(=O)CC3C2(CCCC3(C)C)C)O
InChI: InChI=1S/C20H28O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,18,21H,6-8,11H2,1-5H3


描述信息

Sugiol is an abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group. It has a role as a plant metabolite, an antiviral agent, an antineoplastic agent, an antioxidant and a radical scavenger. It is an abietane diterpenoid, a carbotricyclic compound, a meroterpenoid, a member of phenols and a cyclic terpene ketone. It is functionally related to a ferruginol.
Sugiol is a natural product found in Austrocedrus chilensis, Libocedrus bidwillii, and other organisms with data available.
An abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group.

同义名列表

13 个代谢物同义名

9(1H)-Phenanthrenone, 2,3,4,4a,10,10a-hexahydro-6-hydroxy-1,1,4a-trimethyl-7-(1-methylethyl)-, (4aS-trans)-; (4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one; (4aS,10aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahy dro-2H-phenanthren-9-one; 6-Hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydrophenanthren- 9(1H)-one; Podocarpa-8,11,13-trien-7-one, 12-hydroxy-13-isopropyl-; 12-Hydroxyabieta-8(14),9(11),12-trien-7-one; 12-Hydroxyabieta-8,11,13-trien-7-one; (+)-Sugiol; Sugiol; 6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one; 12-Hydroxy-13-isopropyl-podocarpa-8,11,13-trien-7-one; Isomicropinic acid; 7-Oxoferruginol



数据库引用编号

13 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)

200 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 AIMP2, ANXA5, ATG12, ATG5, BCL2, BECN1, BIRC5, CCND1, CLEC7A, LGALS1, MAPK8, MAPK9, PTPN9, STAT3
Golgi apparatus, trans-Golgi network membrane 1 BECN1
Peripheral membrane protein 6 ACHE, ANXA5, ATG12, ATG5, BECN1, CYP1B1
Endosome membrane 1 BECN1
Endoplasmic reticulum membrane 4 BCL2, BECN1, CYP1B1, TKT
Mitochondrion membrane 1 BECN1
Cytoplasmic vesicle, autophagosome 1 BECN1
Nucleus 10 ACHE, AIMP2, BCL2, BECN1, BIRC5, CCND1, MAPK8, MAPK9, STAT3, TOP1
autophagosome 3 ATG12, ATG5, BECN1
cytosol 13 AIMP2, ANXA5, ATG12, ATG5, BCL2, BECN1, BIRC5, CCND1, LGALS1, MAPK8, MAPK9, STAT3, TKT
dendrite 1 BECN1
mitochondrial membrane 1 BECN1
nuclear body 2 BECN1, TKT
phagocytic vesicle 1 BECN1
phosphatidylinositol 3-kinase complex, class III 1 BECN1
trans-Golgi network 1 BECN1
centrosome 1 CCND1
nucleoplasm 9 ATG12, BIRC5, CCND1, MAPK8, MAPK9, PTPN9, STAT3, TKT, TOP1
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 4 ACHE, CLEC7A, TKT, TNF
Synapse 2 ACHE, MAPK8
cell surface 3 ACHE, CLEC7A, TNF
glutamatergic synapse 1 ATG5
Golgi apparatus 1 ACHE
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
postsynapse 1 ATG5
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 AIMP2
endosome 1 BECN1
plasma membrane 8 ACHE, BCHE, CLEC7A, LGALS1, MAPK9, STAT3, TKT, TNF
Membrane 7 ACHE, AIMP2, ANXA5, ATG5, BCL2, CLEC7A, CYP1B1
apical plasma membrane 1 TKT
axon 2 ATG5, MAPK8
extracellular exosome 3 ANXA5, LGALS1, TKT
endoplasmic reticulum 2 BCL2, BECN1
extracellular space 4 ACHE, BCHE, LGALS1, TNF
perinuclear region of cytoplasm 1 ACHE
Schaffer collateral - CA1 synapse 2 ATG5, MAPK9
bicellular tight junction 1 CCND1
mitochondrion 3 BCL2, CYP1B1, MAPK9
protein-containing complex 4 ATG12, ATG5, BCL2, BIRC5
intracellular membrane-bounded organelle 2 ATG12, CYP1B1
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 TKT
Secreted 3 ACHE, BCHE, LGALS1
extracellular region 5 ACHE, ANXA5, BCHE, LGALS1, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Extracellular side 1 ACHE
transcription regulator complex 1 STAT3
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 2 ANXA5, TNF
Secreted, extracellular space, extracellular matrix 1 LGALS1
actin cytoskeleton 1 TKT
perikaryon 1 TOP1
microtubule cytoskeleton 1 BIRC5
nucleolus 1 TOP1
midbody 1 BIRC5
P-body 1 TOP1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 CLEC7A, TNF
vesicle 1 TKT
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton, spindle 1 BIRC5
focal adhesion 2 ANXA5, TKT
microtubule 1 BIRC5
spindle 1 BIRC5
Peroxisome 1 TKT
basement membrane 1 ACHE
collagen-containing extracellular matrix 2 ANXA5, LGALS1
axoneme 1 ATG5
nuclear speck 1 MAPK9
interphase microtubule organizing center 1 BIRC5
receptor complex 1 TKT
Zymogen granule membrane 1 ANXA5
chromatin 1 STAT3
autophagosome membrane 1 ATG12
phagocytic cup 1 TNF
phagocytic vesicle membrane 2 ATG12, ATG5
Chromosome 2 BIRC5, TOP1
centriole 1 BIRC5
[Isoform 5]: Cytoplasm 1 CLEC7A
Nucleus, nucleolus 1 TOP1
nuclear chromosome 1 BIRC5
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
fibrillar center 1 TOP1
Chromosome, centromere 1 BIRC5
Chromosome, centromere, kinetochore 1 BIRC5
phagophore assembly site 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type I 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type II 1 BECN1
Preautophagosomal structure membrane 2 ATG12, ATG5
Atg12-Atg5-Atg16 complex 2 ATG12, ATG5
mitochondria-associated endoplasmic reticulum membrane contact site 1 ATG5
phagophore assembly site membrane 2 ATG12, ATG5
Nucleus, nucleoplasm 1 TOP1
side of membrane 1 ACHE
myelin sheath 1 BCL2
endoplasmic reticulum lumen 2 BCHE, LGALS1
transcription repressor complex 1 CCND1
male germ cell nucleus 1 TOP1
kinetochore 1 BIRC5
nuclear envelope lumen 1 BCHE
chromosome, centromeric region 1 BIRC5
vesicle membrane 1 ANXA5
chromosome passenger complex 1 BIRC5
cytoplasmic microtubule 1 BIRC5
synaptic cleft 1 ACHE
protein-DNA complex 1 TOP1
spindle microtubule 1 BIRC5
survivin complex 1 BIRC5
basal dendrite 1 MAPK8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
transferase complex 2 ATG12, ATG5
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
[Isoform 7]: Cytoplasm 1 CLEC7A
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
galectin complex 1 LGALS1
neuron projection terminus 1 PTPN9
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
[Isoform 6]: Cytoplasm 1 CLEC7A
cyclin D1-CDK4 complex 1 CCND1
[Isoform H]: Cell membrane 1 ACHE
cyclin D1-CDK6 complex 1 CCND1
cytoplasmic side of mitochondrial outer membrane 1 BECN1
[Beclin-1-C 35 kDa]: Mitochondrion 1 BECN1
[Beclin-1-C 37 kDa]: Mitochondrion 1 BECN1
phagophore 1 ATG5
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Abdukriem Kadir, Guijuan Zheng, Xiaofeng Zheng, Pengfei Jin, Maitinuer Maiwulanjiang, Biao Gao, Haji Akber Aisa, Guangmin Yao. Structurally Diverse Diterpenoids from the Roots of Salvia deserta Based on Nine Different Skeletal Types. Journal of natural products. 2021 05; 84(5):1442-1452. doi: 10.1021/acs.jnatprod.0c01180. [PMID: 33978415]
  • Vivek K Bajpai, Sonam Sonwal, Seung-Kyu Hwang, Shruti Shukla, Imran Khan, Debasish Kumar Dey, Lei Chen, Jesus Simal-Gandara, Jianbo Xiao, Yun Suk Huh, Young-Kyu Han. Sugiol, a diterpenoid: Therapeutic actions and molecular pathways involved. Pharmacological research. 2021 01; 163(?):105313. doi: 10.1016/j.phrs.2020.105313. [PMID: 33246173]
  • Yaping Mao, Ying Ma, Tong Chen, Xiaohui Ma, Yanqin Xu, Junling Bu, Qishuang Li, Baolong Jin, Yanan Wang, Yong Li, Guanghong Cui, Yujun Zhao, Jinfu Tang, Ye Shen, Changjiangsheng Lai, Wen Zeng, Min Chen, Juan Guo, Luqi Huang. Functional Integration of Two CYP450 Genes Involved in Biosynthesis of Tanshinones for Improved Diterpenoid Production by Synthetic Biology. ACS synthetic biology. 2020 07; 9(7):1763-1770. doi: 10.1021/acssynbio.0c00136. [PMID: 32551504]
  • Nawal M Al Musayeib, Musarat Amina, Gadah Abdulaziz Al-Hamoud, Gamal A Mohamed, Sabrin R M Ibrahim, Samah Shabana. Plectrabarbene, a New Abietane Diterpene from Plectranthus barbatus Aerial Parts. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102365. [PMID: 32443693]
  • Débora Botura Scariot, Hélito Volpato, Nilma de Souza Fernandes, Edna Filipa Pais Soares, Tânia Ueda-Nakamura, Benedito Prado Dias-Filho, Zia Ud Din, Edson Rodrigues-Filho, Adley Forti Rubira, Olga Borges, Maria Do Céu Sousa, Celso Vataru Nakamura. Activity and Cell-Death Pathway in Leishmania infantum Induced by Sugiol: Vectorization Using Yeast Cell Wall Particles Obtained From Saccharomyces cerevisiae. Frontiers in cellular and infection microbiology. 2019; 9(?):208. doi: 10.3389/fcimb.2019.00208. [PMID: 31259161]
  • Chengfei Hao, Xibo Zhang, Hongtao Zhang, Haitao Shang, Jianheng Bao, Haibo Wang, Zhonglian Li. Sugiol (127horbar;hydroxyabieta-8,11,13-trien-7-one) targets human pancreatic carcinoma cells (Mia-PaCa2) by inducing apoptosis, G2/M cell cycle arrest, ROS production and inhibition of cancer cell migration. Journal of B.U.ON. : official journal of the Balkan Union of Oncology. 2018 Jan; 23(1):205-210. doi: . [PMID: 29552785]
  • Xiao-Jiao Chen, Ling Ni, Mei-Fen Bao, Li Wang, Xiang-Hai Cai. Abietane diterpenoids from Cephalotaxus lanceolata. Natural product research. 2017 Nov; 31(21):2473-2478. doi: 10.1080/14786419.2017.1314280. [PMID: 28399666]
  • Vivek K Bajpai, Na-Hyung Kim, Kangmin Kim, Sun Chul Kang. Antiviral potential of a diterpenoid compound sugiol from Metasequoia glyptostroboides. Pakistan journal of pharmaceutical sciences. 2016 May; 29(3 Suppl):1077-80. doi: NULL. [PMID: 27383486]
  • Juan Guo, Xiaohui Ma, Yuan Cai, Ying Ma, Zhilai Zhan, Yongjin J Zhou, Wujun Liu, Mengxin Guan, Jian Yang, Guanghong Cui, Liping Kang, Lei Yang, Ye Shen, Jinfu Tang, Huixin Lin, Xiaojing Ma, Baolong Jin, Zhenming Liu, Reuben J Peters, Zongbao K Zhao, Luqi Huang. Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones. The New phytologist. 2016 Apr; 210(2):525-34. doi: 10.1111/nph.13790. [PMID: 26682704]
  • H Saijo, H Kofujita, K Takahashi, T Ashitani. Antioxidant activity and mechanism of the abietane-type diterpene ferruginol. Natural product research. 2015; 29(18):1739-43. doi: 10.1080/14786419.2014.997233. [PMID: 25588148]
  • Vivek K Bajpai, Ajay Sharma, Sun Chul Kang, Kwang-Hyun Baek. Antioxidant, lipid peroxidation inhibition and free radical scavenging efficacy of a diterpenoid compound sugiol isolated from Metasequoia glyptostroboides. Asian Pacific journal of tropical medicine. 2014 Jan; 7(1):9-15. doi: 10.1016/s1995-7645(13)60183-2. [PMID: 24418075]
  • Shiyou Li, Ping Wang, Guangrui Deng, Wei Yuan, Zushang Su. Cytotoxic compounds from invasive giant salvinia (Salvinia molesta) against human tumor cells. Bioorganic & medicinal chemistry letters. 2013 Dec; 23(24):6682-7. doi: 10.1016/j.bmcl.2013.10.040. [PMID: 24210499]
  • Li Zhang, Zu-Jiang Xu, Yu-Jing Feng, Ding-Yong Wang. [Chemical constituents of roots of Celastrus orbiculatus]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2013 Apr; 36(4):569-72. doi: . [PMID: 24134003]
  • Marcio Fronza, Evelyn Lamy, Stefan Günther, Berta Heinzmann, Stefan Laufer, Irmgard Merfort. Abietane diterpenes induce cytotoxic effects in human pancreatic cancer cell line MIA PaCa-2 through different modes of action. Phytochemistry. 2012 Jun; 78(?):107-19. doi: 10.1016/j.phytochem.2012.02.015. [PMID: 22436445]
  • Muhammad Iqbal Choudhary, Amjad Hussain, Zulfiqar Ali, Achyut Adhikari, Samina A Sattar, Syed A Ayatollahi, Abdullah M Al-Majid. Diterpenoids including a novel dimeric conjugate from Salvia leriaefolia. Planta medica. 2012 Feb; 78(3):269-75. doi: 10.1055/s-0031-1280454. [PMID: 22174076]
  • M Fronza, R Murillo, S Ślusarczyk, M Adams, M Hamburger, B Heinzmann, S Laufer, I Merfort. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica. Bioorganic & medicinal chemistry. 2011 Aug; 19(16):4876-81. doi: 10.1016/j.bmc.2011.06.067. [PMID: 21775156]
  • Chi-I Chang, Wen-Ching Chen, Yi-Yuan Shao, Guey-Ru Yeh, Ning-Sun Yang, Wenchang Chiang, Yueh-Hsiung Kuo. A new labdane-type diterpene from the bark of Juniperus chinensis Linn. Natural product research. 2008; 22(13):1158-62. doi: 10.1080/14786410601132444. [PMID: 18855216]
  • Chih-Chun Wen, Yueh-Hsiung Kuo, Jia-Tsrong Jan, Po-Huang Liang, Sheng-Yang Wang, Hong-Gi Liu, Ching-Kuo Lee, Shang-Tzen Chang, Chih-Jung Kuo, Shoei-Sheng Lee, Chia-Chung Hou, Pei-Wen Hsiao, Shih-Chang Chien, Lie-Fen Shyur, Ning-Sun Yang. Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. Journal of medicinal chemistry. 2007 Aug; 50(17):4087-95. doi: 10.1021/jm070295s. [PMID: 17663539]
  • Kwang-Hee Son, Hyun-Mi Oh, Sung-Kyu Choi, Dong Cho Han, Byoung-Mog Kwon. Anti-tumor abietane diterpenes from the cones of Sequoia sempervirens. Bioorganic & medicinal chemistry letters. 2005 Apr; 15(8):2019-21. doi: 10.1016/j.bmcl.2005.02.057. [PMID: 15808460]
  • Kuo-Ping Chao, Kuo-Feng Hua, Hsien-Yeh Hsu, Yu-Chang Su, Shang-Tzen Chang. Anti-inflammatory activity of sugiol, a diterpene isolated from Calocedrus formosana bark. Planta medica. 2005 Apr; 71(4):300-5. doi: 10.1055/s-2005-864094. [PMID: 15856404]