Marrubiin.
Popoola OK, Elbagory AM, Ameer F, Hussein AA.
Molecules. 2013 Jul 29;18(8):9049-60. doi: 10.3390/molecules18089049.

Functional characterization of the cytochrome P450 monooxygenase CYP71AU87 indicates a role in marrubiin biosynthesis in the medicinal plant Marrubium vulgare.
Karunanithi PS, Dhanota P, Addison JB, Tong S, Fiehn O, Zerbe P.
BMC Plant Biol. 2019 Mar 25;19(1):114. doi: 10.1186/s12870-019-1702-5.

Marrubiin-loaded solid lipid nanoparticles' impact on TNF-α treated umbilical vein endothelial cells: A study for cardioprotective effect.
Nakhlband A, Eskandani M, Saeedi N, Ghafari S, Omidi Y, Barar J, Garjani A.
Colloids Surf B Biointerfaces. 2018 Apr 1;164:299-307. doi: 10.1016/j.colsurfb.2018.01.046. Epub 2018 Feb 3.

Protective effects of marrubiin improve endometriosis through suppression of the expression of RANTES.
Sun XH.
Mol Med Rep. 2017 Sep;16(3):3339-3344. doi: 10.3892/mmr.2017.6969. Epub 2017 Jul 14.

Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms.
Mnonopi N, Levendal RA, Mzilikazi N, Frost CL.
Phytomedicine. 2012 Apr 15;19(6):488-93. doi: 10.1016/j.phymed.2011.12.008. Epub 2012 Feb 10.

The cardioprotective effects of marrubiin, a diterpenoid found in Leonotis leonurus extracts.
Mnonopi N, Levendal RA, Davies-Coleman MT, Frost CL.
J Ethnopharmacol. 2011 Oct 31;138(1):67-75. doi: 10.1016/j.jep.2011.08.041. Epub 2011 Aug 25.

Gastroprotective activity of methanol extract and marrubiin obtained from leaves of Marrubium vulgare L. (Lamiaceae).
Paula de Oliveira A, Santin JR, Lemos M, Klein Júnior LC, Couto AG, Meyre da Silva Bittencourt C, Filho VC, Faloni de Andrade S.
J Pharm Pharmacol. 2011 Sep;63(9):1230-7. doi: 10.1111/j.2042-7158.2011.01321.x. Epub 2011 Jul 7

Antioedematogenic effect of marrubiin obtained from Marrubium vulgare.
Stulzer HK, Tagliari MP, Zampirolo JA, Cechinel-Filho V, Schlemper V.
J Ethnopharmacol. 2006 Dec 6;108(3):379-84. Epub 2006 Jun 2.
Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare.
De Jesus RA, Cechinel-Filho V, Oliveira AE, Schlemper V.

The role of general metabolites in the biosynthesis of natural products. I. The terpene marrubiin.
Breccia A, Badiello R.
Z Naturforsch B. 1967 Jan;22(1):44-9.

Marrubiin, a diterprene, was identified in 1984 as the first diterpene isolated from the leaves of the Horehound (Marrubium vulgare L.).

It gives the bitter taste to the Horehound and to many other plants of the Laminaceae family.

Marrubiin and the organic extract suppressed coagulation, platelet aggregation and inflammatory markers. For the coagulation markers it was found that the organic extract and marrubiin significantly prolonged activated partial thromboplastin time (APTT). Fibrin and D-dimer formation were drastically decreased. These findings were observed in an ex vivo model and an obese rat model. Chemokines enhance leukocyte recruitment to inflammatory sites. TNF-α and RANTES secretion were significantly reduced by the extract and marrubiin when determined in the obese rat model relative to the controls. Calcium mobilization and TXB(2) synthesis were suppressed by the extract and marrubiin. An in vitro model was used to elucidate the antiplatelet mechanism and it was found that the extract and marrubiin inhibited platelet aggregation by inhibiting the binding of fibrinogen to glycoprotein (GP) IIb/IIIa receptor in a concentration dependent manner (1).

Marrubiin studies

Molecular Formula : C₂₀H₂₈O₄

Molecular Weight : 332.44

CAS : 465-92-9

Bibliografia_____________

(1)  The cardioprotective effects of marrubiin, a diterpenoid found in Leonotis leonurus extracts.

Mnonopi N, Levendal RA, Davies-Coleman MT, Frost CL.J Ethnopharmacol. 2011;138(1):67–75. doi: 10.1016/j.jep.2011.08.041