Cubebin (BioDeep_00000395958)

Main id: BioDeep_00000008150

 

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


(2S,3R,4R)-3,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)-tetrahydrofuran-2-ol

化学式: C20H20O6 (356.125982)
中文名称: 荜澄茄素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C(C(C(O1)O)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
InChI: InChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2/t14-,15+,20-/m0/s1

描述信息

(-)-cubebin is a lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities. It has a role as an antimicrobial agent, a trypanocidal drug, an anti-inflammatory agent, an analgesic, a histamine antagonist and a plant metabolite. It is a lignan, a member of benzodioxoles, a secondary alcohol, a cyclic acetal and a lactol.
Cubebin is a natural product found in Piper nigrum, Aristolochia elegans, and other organisms with data available.

同义名列表

27 个代谢物同义名

(2S,3R,4R)-3,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)-tetrahydrofuran-2-ol; 2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-, (2S,3R,4R)-; (2S,3R,4R)-3,4-bis(benzo[d][1,3]dioxol-5-ylmethyl)tetrahydrofuran-2-ol; (2s,3r,4r)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol; (2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol; 3,4-Bis[(1,3-benzodioxole-5-yl)methyl]tetrahydrofuran-2-ol; (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol; 2-Furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-; 9-Hydroxy-3,4:3,4-bis(methylenedioxy)-9,9-epoxylignan; 3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol; 2-Furanol, tetrahydro-3,4-dipiperonyl-; Tetrahydro-3,4-dipiperonylfuran-2-ol; (8R,8R,9S)-cubebin; (-)-beta-Cubebin; .beta.-Cubebin; beta-cubebin; CUBEBIN [MI]; (-)-Cubebin; AI3-62265; Cubebine; Cubebin; (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)-2-tetrahydrofuranol; EINECS 242-300-6; AIDS-002469; 18423-69-3; AIDS002469; C10549



数据库引用编号

14 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)

24 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。



文献列表

  • Neetu Agrawal, Deepika Goyal, Ahsas Goyal. A review on multi-therapeutic potential of (-)-cubebin: experimental evidences. Natural product research. 2023 Nov; 37(24):4290-4301. doi: 10.1080/14786419.2023.2177849. [PMID: 36775642]
  • Motohiko Ukiya, Daisuke Sato, Hirokazu Kimura, Mamoru Koketsu, Nyunt Phay, Atsuyoshi Nishina. (-)-O-Methylcubebin from Vitex trifolia Enhanced Adipogenesis in 3T3-L1 Cells via the Inhibition of ERK1/2 and p38MAPK Phosphorylation. Molecules (Basel, Switzerland). 2019 Dec; 25(1):. doi: 10.3390/molecules25010073. [PMID: 31878261]
  • Matheus Souza de Paula Carlis, Aline Féboli, Antonio Carlos de Laurentiz, Rosemeire da Silva Filardi, Anna Helena Prizantelli de Oliveira, Márcio Luis Andrade E Silva, Luciano Alves Dos Anjos, Lizandra Guidi Magalhães, Rosangela da Silva de Laurentiz. In vitro anthelmintic activity of the crude hydroalcoholic extract of Piper cubeba fruits and isolated natural products against gastrointestinal nematodes in sheep. Veterinary parasitology. 2019 Nov; 275(?):108932. doi: 10.1016/j.vetpar.2019.108932. [PMID: 31600614]
  • Morina Adfa, Rizki Rahmad, Masayuki Ninomiya, Salprima Yudha S, Kaori Tanaka, Mamoru Koketsu. Antileukemic activity of lignans and phenylpropanoids of Cinnamomum parthenoxylon. Bioorganic & medicinal chemistry letters. 2016 Feb; 26(3):761-764. doi: 10.1016/j.bmcl.2015.12.096. [PMID: 26774581]
  • Julie Marie V Timple, Lizandra Guidi Magalhães, Karen Cristina Souza Rezende, Ana Carolina Pereira, Wilson Roberto Cunha, Márcio Luis Andrade e Silva, Ole Valente Mortensen, Andréia C K Fontana. The lignan (-)-hinokinin displays modulatory effects on human monoamine and GABA transporter activities. Journal of natural products. 2013 Oct; 76(10):1889-95. doi: 10.1021/np400452n. [PMID: 24112084]
  • A A A de Rezende, M L A e Silva, D C Tavares, W R Cunha, K C S Rezende, J K Bastos, M Lehmann, H H R de Andrade, Z R Guterres, L P Silva, M A Spanó. The effect of the dibenzylbutyrolactolic lignan (-)-cubebin on doxorubicin mutagenicity and recombinogenicity in wing somatic cells of Drosophila melanogaster. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Jun; 49(6):1235-41. doi: 10.1016/j.fct.2011.03.001. [PMID: 21385598]
  • Edson Luis Maistro, André Vinicius Marcondes Natel, Gustavo Henrique Bianco de Souza, Fábio Ferreira Perazzo. Genotoxic effects of (-)-cubebin in somatic cells of mice. Journal of applied toxicology : JAT. 2011 Mar; 31(2):185-9. doi: 10.1002/jat.1616. [PMID: 21351285]
  • Noriko Hirata, Shunsuke Naruto, Kazunori Inaba, Kimihisa Itoh, Masashi Tokunaga, Munekazu Iinuma, Hideaki Matsuda. Histamine release inhibitory activity of Piper nigrum leaf. Biological & pharmaceutical bulletin. 2008 Oct; 31(10):1973-6. doi: 10.1248/bpb.31.1973. [PMID: 18827366]
  • Gang Zhang, Satoko Shimokawa, Matsuri Mochizuki, Takuya Kumamoto, Waka Nakanishi, Toshiko Watanabe, Tsutomu Ishikawa, Kenjiro Matsumoto, Kimihito Tashima, Syunji Horie, Yoshihiro Higuchi, Oswaldo Pesantes Dominguez. Chemical constituents of Aristolochia constricta: antispasmodic effects of its constituents in guinea-pig ileum and isolation of a diterpeno-lignan hybrid. Journal of natural products. 2008 Jul; 71(7):1167-72. doi: 10.1021/np800041t. [PMID: 18570470]
  • Jianying Yam, Matthias Kreuter, Juergen Drewe. Piper cubeba targets multiple aspects of the androgen-signalling pathway. A potential phytotherapy against prostate cancer growth?. Planta medica. 2008 Jan; 74(1):33-8. doi: 10.1055/s-2007-993758. [PMID: 18080233]
  • M L A Silva, H S Coímbra, A C Pereira, V A Almeida, T C Lima, E S Costa, A H C Vinhólis, V A Royo, R Silva, A A S Filho, W R Cunha, N A J C Furtado, Carlos H G Martins, T C Carvalho, J K Bastos. Evaluation of piper cubeba extract, (-)-cubebin and its semi-synthetic derivatives against oral pathogens. Phytotherapy research : PTR. 2007 May; 21(5):420-2. doi: 10.1002/ptr.2088. [PMID: 17236178]
  • Inara C de Pascoli, Isabele R Nascimento, Lucia M X Lopes. Configurational analysis of cubebins and bicubebin from Aristolochia lagesiana and Aristolochia pubescens. Phytochemistry. 2006 Apr; 67(7):735-42. doi: 10.1016/j.phytochem.2006.01.019. [PMID: 16500688]
  • Hideaki Matsuda, Yoshiko Kawaguchi, Miho Yamazaki, Noriko Hirata, Shunsuke Naruto, Yusuke Asanuma, Takayuki Kaihatsu, Michinori Kubo. Melanogenesis stimulation in murine B16 melanoma cells by Piper nigrum leaf extract and its lignan constituents. Biological & pharmaceutical bulletin. 2004 Oct; 27(10):1611-6. doi: 10.1248/bpb.27.1611. [PMID: 15467205]
  • Isabele R Nascimento, Afonso T Murata, Sergio A Bortoli, Lucia M X Lopes. Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae. Pest management science. 2004 Apr; 60(4):413-6. doi: 10.1002/ps.805. [PMID: 15119605]
  • J K Bastos, J C Carvalho, G H de Souza, A H Pedrazzi, S J Sarti. Anti-inflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo Griseb. Journal of ethnopharmacology. 2001 May; 75(2-3):279-82. doi: 10.1016/s0378-8741(01)00171-4. [PMID: 11297863]