Marrubiin (BioDeep_00000000985)

   

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


2H-Naphtho(1,8-bc)furan-2-one, 6-(2-(3-furanyl)ethyl)decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS-(2aalpha,5abeta,6alpha,7alpha,8aalpha,8balpha))-

化学式: C20H28O4 (332.19874880000003)
中文名称: 夏至草素
谱图信息: 最多检出来源 Viridiplantae(plant) 38.1%

分子结构信息

SMILES: CC1CC2C3C(CCCC3(C1(CCC4=COC=C4)O)C)(C(=O)O2)C
InChI: InChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1

描述信息

Marrubiin is a gamma-lactone.
Marrubiin is a natural product found in Marrubium globosum, Marrubium anisodon, and other organisms with data available.
Marrubiin, isolated from Marrubium vulgare, exhibits vasorelaxant and antioedematogenic activity. Marrubiin alleviates diabetic symptoms in animals[1][2][3].

同义名列表

11 个代谢物同义名

2H-Naphtho(1,8-bc)furan-2-one, 6-(2-(3-furanyl)ethyl)decahydro-6-hydroxy-2a,5a,7-trimethyl-, (2aS-(2aalpha,5abeta,6alpha,7alpha,8aalpha,8balpha))-; 2H-Naphtho[1, 6-[2-(3-furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-, [2aS-(2a.alpha.,5a.beta.,6.alpha.,7.alpha.,8a.alpha.,8b.alpha.)]-; 2H-Naphtho[1,8-bc]furan-2-one,6-[2-(3-furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-,(2aS,5aS,6R,7R,8aR,8bR)-; (2AS,5AS,6R,7R,8AR,8BR)-6-(2-(3-FURANYL)ETHYL)DECAHYDRO-6-HYDROXY-2A,5A,7-TRIMETHYL-2H-NAPHTHO(1,8-BC)FURAN-2-ONE; (1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-3-one; 8.beta.H-Labda-13(16), 15,16-epoxy-6.beta.,9-dihydroxy-, .gamma.-lactone; Marrubium bitter; MARRUBIIN [MI]; Marrubiin; MARRUBIN; Marrubiin



数据库引用编号

19 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)

8 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

  • Tugce Demiroz Akbulut, Fadime Aydin Kose, Betul Demirci, Sura Baykan. Chemical Profile and Cytotoxicity Evaluation of Aerial Parts of Marrubium vulgare L. From Different Locations in Turkey. Chemistry & biodiversity. 2023 Mar; ?(?):e202201188. doi: 10.1002/cbdv.202201188. [PMID: 36929733]
  • M Rezgui, N Majdoub, B Mabrouk, A Baldisserotto, A Bino, L B Ben Kaab, S Manfredini. Antioxidant and antifungal activities of marrubiin, extracts and essential oil from Marrubium vulgare L. against pathogenic dermatophyte strains. Journal de mycologie medicale. 2020 Apr; 30(1):100927. doi: 10.1016/j.mycmed.2020.100927. [PMID: 31983544]
  • Emanuela Martino, Serena Della Volpe, Valeria Cavalloro, Bedis Amri, Leila Bettaeib Been Kaab, Giorgio Marrubini, Daniela Rossi, Simona Collina. The use of a microwave-assisted solvent extraction coupled with HPLC-UV/PAD to assess the quality of Marrubium vulgare L. (white horehound) herbal raw material. Phytochemical analysis : PCA. 2019 Jul; 30(4):377-384. doi: 10.1002/pca.2820. [PMID: 30687967]
  • Prema S Karunanithi, Puja Dhanota, J Bennett Addison, Shen Tong, Oliver Fiehn, Philipp Zerbe. Functional characterization of the cytochrome P450 monooxygenase CYP71AU87 indicates a role in marrubiin biosynthesis in the medicinal plant Marrubium vulgare. BMC plant biology. 2019 Mar; 19(1):114. doi: 10.1186/s12870-019-1702-5. [PMID: 30909879]
  • Ailar Nakhlband, Morteza Eskandani, Nazli Saeedi, Samad Ghafari, Yadollah Omidi, Jaleh Barar, Alireza Garjani. Marrubiin-loaded solid lipid nanoparticles' impact on TNF-α treated umbilical vein endothelial cells: A study for cardioprotective effect. Colloids and surfaces. B, Biointerfaces. 2018 Apr; 164(?):299-307. doi: 10.1016/j.colsurfb.2018.01.046. [PMID: 29413609]
  • Vineet Mittal, Arun Nanda. Intensification of marrubiin concentration by optimization of microwave-assisted (low CO2 yielding) extraction process for Marrubium vulgare using central composite design and antioxidant evaluation. Pharmaceutical biology. 2017 Dec; 55(1):1337-1347. doi: 10.1080/13880209.2017.1297837. [PMID: 28298169]
  • Bédis Amri, Emanuela Martino, Francesca Vitulo, Federica Corana, Leila Bettaieb-Ben Kaâb, Marta Rui, Daniela Rossi, Michela Mori, Silvia Rossi, Simona Collina. Marrubium vulgare L. Leave Extract: Phytochemical Composition, Antioxidant and Wound Healing Properties. Molecules (Basel, Switzerland). 2017 Oct; 22(11):. doi: 10.3390/molecules22111851. [PMID: 29143793]
  • Saoussen Hammami, Zhenzhen Li, Mingjie Huang, Ridha El Mokni, Hatem Dhaouadi, Sheng Yin. New bioactive labdane diterpenoids from Marrubium aschersonii. Natural product research. 2016 Oct; 30(19):2142-8. doi: 10.1080/14786419.2016.1143828. [PMID: 26927415]
  • Philipp Zerbe, Angela Chiang, Harpreet Dullat, Mark O'Neil-Johnson, Courtney Starks, Björn Hamberger, Jörg Bohlmann. Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare. The Plant journal : for cell and molecular biology. 2014 Sep; 79(6):914-27. doi: 10.1111/tpj.12589. [PMID: 24990389]
  • N Mnonopi, R-A Levendal, N Mzilikazi, C L Frost. Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2012 Apr; 19(6):488-93. doi: 10.1016/j.phymed.2011.12.008. [PMID: 22326550]
  • Nabila Zaabat, Anne-Emmanuelle Hay, Serge Michalet, Nicole Darbour, Christine Bayet, Inès Skandrani, Leila Chekir-Ghedira, Salah Akkal, Marie-Geneviève Dijoux-Franca. Antioxidant and antigenotoxic properties of compounds isolated from Marrubium deserti de Noé. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2011 Dec; 49(12):3328-35. doi: 10.1016/j.fct.2011.08.026. [PMID: 21924316]
  • Nandipha Mnonopi, Ruby-Ann Levendal, Michael T Davies-Coleman, Carminita L Frost. The cardioprotective effects of marrubiin, a diterpenoid found in Leonotis leonurus extracts. Journal of ethnopharmacology. 2011 Oct; 138(1):67-75. doi: 10.1016/j.jep.2011.08.041. [PMID: 21893184]
  • Ana Paula de Oliveira, José Roberto Santin, Marivane Lemos, Luiz Carlos Klein Júnior, Angélica Garcia Couto, Christiane Meyre da Silva Bittencourt, Valdir Cechinel Filho, Sérgio Faloni de Andrade. Gastroprotective activity of methanol extract and marrubiin obtained from leaves of Marrubium vulgare L. (Lamiaceae). The Journal of pharmacy and pharmacology. 2011 Sep; 63(9):1230-7. doi: 10.1111/j.2042-7158.2011.01321.x. [PMID: 21827496]
  • Song Zhang, Shou-Lang Geshang, Zuo-Ma Dawa, Yan Zhou, Shu-Lin Peng. [Studies on chemical constituents of Eriophyton wallichii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2007 May; 32(9):824-6. doi: . [PMID: 17639985]
  • Hellen K Stulzer, Monika P Tagliari, Julio A Zampirolo, Valdir Cechinel-Filho, Valfredo Schlemper. Antioedematogenic effect of marrubiin obtained from Marrubium vulgare. Journal of ethnopharmacology. 2006 Dec; 108(3):379-84. doi: 10.1016/j.jep.2006.05.023. [PMID: 16846706]
  • C Meyre-Silva, R A Yunes, V Schlemper, F Campos-Buzzi, V Cechinel-Filho. Analgesic potential of marrubiin derivatives, a bioactive diterpene present in Marrubium vulgare (Lamiaceae). Farmaco (Societa chimica italiana : 1989). 2005 Apr; 60(4):321-6. doi: 10.1016/j.farmac.2005.01.003. [PMID: 15848207]
  • R A De Jesus, V Cechinel-Filho, A E Oliveira, V Schlemper. Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2000 Apr; 7(2):111-5. doi: 10.1016/s0944-7113(00)80082-3. [PMID: 10839213]
  • W Knöss, B Reuter, J Zapp. Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway. The Biochemical journal. 1997 Sep; 326 ( Pt 2)(?):449-54. doi: 10.1042/bj3260449. [PMID: 9291117]
  • E Telek, L Tõth, L Botz, I Máthé. [Chemical tests with Marrubium species. Official data on Marubii herba in Pharmacopoeia Hungarica VII]. Acta pharmaceutica Hungarica. 1997 Jan; 67(1):31-7. doi: . [PMID: 9163258]
  • L Giuliani, G Carmignani, E Belgrano, P Puppo. Transcatheter arterial embolization in urological tumors: the use of isobutyl-2-cyanoacrylate. The Journal of urology. 1979 May; 121(5):630-4. doi: 10.1016/s0022-5347(17)56913-x. [PMID: 439260]