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MedKoo Cat#: 464705 | Name: Marrubiin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Marrubiin is a labdane diterpenoid lactone originally isolated from M. vulgare that has diverse biological activities. It inhibits potassium chloride-induced contractions of rat aortic rings (IC50 = 24 µM). Marrubiin (100 mg/kg) inhibits ovalbumin-induced allergic ear edema in mice. It inhibits acetic acid-induced writhing and capsaicin-induced paw licking in mice with ID50 values of 2.2 and 28.8 µmol/kg, respectively.

Chemical Structure

Marrubiin
Marrubiin
CAS#465-92-9

Theoretical Analysis

MedKoo Cat#: 464705

Name: Marrubiin

CAS#: 465-92-9

Chemical Formula: C20H28O4

Exact Mass: 332.1988

Molecular Weight: 332.44

Elemental Analysis: C, 72.26; H, 8.49; O, 19.25

Price and Availability

Size Price Availability Quantity
5mg USD 405.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
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Synonym
Marrubiin; (+)-Marrubiin; (+) Marrubiin; NSC 36693; NSC-36693; NSC36693;
IUPAC/Chemical Name
(2aS,2a1R,5aS,6R,7R,8aR)-6-(2-(furan-3-yl)ethyl)-6-hydroxy-2a,5a,7-trimethyldecahydro-2H-naphtho[1,8-bc]furan-2-one
InChi Key
HQLLRHCTVDVUJB-OBHOOXMTSA-N
InChi Code
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
SMILES Code
C[C@]12[C@]3([C@]([H])(OC([C@@]3(C)CCC2)=O)C[C@@H](C)[C@@]1(CCC4=COC=C4)O)[H]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Marrubiin, isolated from Marrubium vulgare, exhibits vasorelaxant and antioedematogenic activity.
In vitro activity:
The stimulatory index of INS-1 cells cultured under hyperglycemic conditions was significantly increased in cells exposed to the organic extract and marrubiin, relative to the hyperglycaemic conditions. Insulin and glucose transporter-2 gene expressions were significantly increased by the organic extract and marrubiin. Reference: Phytomedicine. 2012 Apr 15;19(6):488-93. https://pubmed.ncbi.nlm.nih.gov/22326550/
In vivo activity:
This paper describes the antioedematogenic profile of marrubiin (1), the main constituent of Marrubium vulgare, a medicinal plant used in folk medicine of several countries to treat different pathologies. Compound (1) was analyzed in a model of microvascular leakage in mice ears. The results show that it exhibits significant and dose-related antioedematogenic effects. In addition, (1) (100 mg/kg) significantly inhibited the OVO-induced allergic edema in actively sensitized animals (maximal inhibition 67.6+/-4%). These results demonstrate that the systemic administration of marrubiin exerts a non-specific inhibitory effect on pro-inflammatory agent-induced microvascular extravasation of Evans blue in mouse ear. Reference: J Ethnopharmacol. 2006 Dec 6;108(3):379-84. https://pubmed.ncbi.nlm.nih.gov/16846706/
Solvent mg/mL mM
Solubility
DMSO 100.0 300.81
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 332.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Mnonopi N, Levendal RA, Mzilikazi N, Frost CL. Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms. Phytomedicine. 2012 Apr 15;19(6):488-93. doi: 10.1016/j.phymed.2011.12.008. Epub 2012 Feb 10. PMID: 22326550. 2. El Bardai S, Morel N, Wibo M, Fabre N, Llabres G, Lyoussi B, Quetin-Leclercq J. The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare. Planta Med. 2003 Jan;69(1):75-7. doi: 10.1055/s-2003-37042. PMID: 12567286. 3. Nidhi, Singh G, Valecha R, Shukla G, Kaushik D, Rahman MA, Gautam RK, Madan K, Mittal V, Singla RK. Neurobehavioral and Biochemical Evidences in Support of Protective Effect of Marrubiin (Furan Labdane Diterpene) from Marrubium vulgare Linn. and Its Extracts after Traumatic Brain Injury in Experimental Mice. Evid Based Complement Alternat Med. 2022 May 24;2022:4457973. doi: 10.1155/2022/4457973. PMID: 35656476; PMCID: PMC9155918. 4. Stulzer HK, Tagliari MP, Zampirolo JA, Cechinel-Filho V, Schlemper V. Antioedematogenic effect of marrubiin obtained from Marrubium vulgare. J Ethnopharmacol. 2006 Dec 6;108(3):379-84. doi: 10.1016/j.jep.2006.05.023. Epub 2006 Jun 2. PMID: 16846706.
In vitro protocol:
1. Mnonopi N, Levendal RA, Mzilikazi N, Frost CL. Marrubiin, a constituent of Leonotis leonurus, alleviates diabetic symptoms. Phytomedicine. 2012 Apr 15;19(6):488-93. doi: 10.1016/j.phymed.2011.12.008. Epub 2012 Feb 10. PMID: 22326550. 2. El Bardai S, Morel N, Wibo M, Fabre N, Llabres G, Lyoussi B, Quetin-Leclercq J. The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare. Planta Med. 2003 Jan;69(1):75-7. doi: 10.1055/s-2003-37042. PMID: 12567286.
In vivo protocol:
1. Nidhi, Singh G, Valecha R, Shukla G, Kaushik D, Rahman MA, Gautam RK, Madan K, Mittal V, Singla RK. Neurobehavioral and Biochemical Evidences in Support of Protective Effect of Marrubiin (Furan Labdane Diterpene) from Marrubium vulgare Linn. and Its Extracts after Traumatic Brain Injury in Experimental Mice. Evid Based Complement Alternat Med. 2022 May 24;2022:4457973. doi: 10.1155/2022/4457973. PMID: 35656476; PMCID: PMC9155918. 2. Stulzer HK, Tagliari MP, Zampirolo JA, Cechinel-Filho V, Schlemper V. Antioedematogenic effect of marrubiin obtained from Marrubium vulgare. J Ethnopharmacol. 2006 Dec 6;108(3):379-84. doi: 10.1016/j.jep.2006.05.023. Epub 2006 Jun 2. PMID: 16846706.
1: Odei-Addo F, Ramlugon S, Levendal RA, Frost CL. Leonotis Leonurus improves the crosstalk between peripheral tissues both in vivo and in vitro. J Ethnopharmacol. 2021 Mar 1;267:113609. doi: 10.1016/j.jep.2020.113609. Epub 2020 Nov 24. PMID: 33242621. 2: Aćimović M, Jeremić K, Salaj N, Gavarić N, Kiprovski B, Sikora V, Zeremski T. Marrubium vulgare L.: A Phytochemical and Pharmacological Overview. Molecules. 2020 Jun 24;25(12):2898. doi: 10.3390/molecules25122898. PMID: 32599693; PMCID: PMC7355696. 3: Sakagami Y, Kondo N, Sawayama Y, Yamakoshi H, Nakamura S. Total Syntheses of Marrubiin and Related Labdane Diterpene Lactones. Molecules. 2020 Apr 1;25(7):1610. doi: 10.3390/molecules25071610. PMID: 32244661; PMCID: PMC7180712. 4: Rezgui M, Majdoub N, Mabrouk B, Baldisserotto A, Bino A, Ben Kaab LB, Manfredini S. Antioxidant and antifungal activities of marrubiin, extracts and essential oil from Marrubium vulgare L. against pathogenic dermatophyte strains. J Mycol Med. 2020 Apr;30(1):100927. doi: 10.1016/j.mycmed.2020.100927. Epub 2020 Jan 11. PMID: 31983544. 5: Karunanithi PS, Dhanota P, Addison JB, Tong S, Fiehn O, Zerbe P. Functional characterization of the cytochrome P450 monooxygenase CYP71AU87 indicates a role in marrubiin biosynthesis in the medicinal plant Marrubium vulgare. BMC Plant Biol. 2019 Mar 25;19(1):114. doi: 10.1186/s12870-019-1702-5. PMID: 30909879; PMCID: PMC6434833. 6: Shimizu E, Koshino H, Noro A, Maruyama M, Shimoda N, Uesugi S, Ohnishi M, Kimura KI. Isolation of a spirolactone norditerpenoid as a yeast Ca2+ signal transduction inhibitor from Kuji amber and evaluation of its effects on PPM1A activity. Fitoterapia. 2019 Apr;134:290-296. doi: 10.1016/j.fitote.2019.02.027. Epub 2019 Mar 2. PMID: 30831200. 7: Martino E, Della Volpe S, Cavalloro V, Amri B, Kaab LBB, Marrubini G, Rossi D, Collina S. 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. Phytochem Anal. 2019 Jul;30(4):377-384. doi: 10.1002/pca.2820. Epub 2019 Jan 27. PMID: 30687967. 8: Nakhlband A, Eskandani M, Saeedi N, Ghafari S, Omidi Y, Barar J, Garjani A. Marrubiin-loaded solid lipid nanoparticles' impact on TNF-α treated umbilical vein endothelial cells: A study for cardioprotective effect. Colloids Surf B Biointerfaces. 2018 Apr 1;164:299-307. doi: 10.1016/j.colsurfb.2018.01.046. Epub 2018 Feb 3. PMID: 29413609. 9: Pellavio G, Rui M, Caliogna L, Martino E, Gastaldi G, Collina S, Laforenza U. Regulation of Aquaporin Functional Properties Mediated by the Antioxidant Effects of Natural Compounds. Int J Mol Sci. 2017 Dec 8;18(12):2665. doi: 10.3390/ijms18122665. PMID: 29292793; PMCID: PMC5751267. 10: Amri B, Martino E, Vitulo F, Corana F, Kaâb LB, Rui M, Rossi D, Mori M, Rossi S, Collina S. Marrubium vulgare L. Leave Extract: Phytochemical Composition, Antioxidant and Wound Healing Properties. Molecules. 2017 Oct 28;22(11):1851. doi: 10.3390/molecules22111851. PMID: 29143793; PMCID: PMC6150401. 11: Jiang L, Tang C, Rao J, Xue Q, Wu H, Wu D, Zhang A, Chen L, Shen Z, Lei L. Systematic identification of the druggable interactions between human protein kinases and naturally occurring compounds in endometriosis. Comput Biol Chem. 2017 Dec;71:136-143. doi: 10.1016/j.compbiolchem.2017.10.006. Epub 2017 Oct 16. PMID: 29096379. 12: Sun XH. Protective effects of marrubiin improve endometriosis through suppression of the expression of RANTES. Mol Med Rep. 2017 Sep;16(3):3339-3344. doi: 10.3892/mmr.2017.6969. Epub 2017 Jul 14. PMID: 28713901. 13: Mittal V, Nanda A. Intensification of marrubiin concentration by optimization of microwave-assisted (low CO2 yielding) extraction process for Marrubium vulgare using central composite design and antioxidant evaluation. Pharm Biol. 2017 Dec;55(1):1337-1347. doi: 10.1080/13880209.2017.1297837. PMID: 28298169; PMCID: PMC7012001. 14: Yamakoshi H, Sawayama Y, Akahori Y, Kato M, Nakamura S. Total Syntheses of (+)-Marrubiin and (-)-Marrulibacetal. Org Lett. 2016 Jul 15;18(14):3430-3. doi: 10.1021/acs.orglett.6b01602. Epub 2016 Jun 24. PMID: 27341320. 15: Yousefi K, Hamedeyazdan S, Torbati M, Fathiazad F. Chromatographic Fingerprint Analysis of Marrubiin in Marrubium vulgare L. via HPTLC Technique. Adv Pharm Bull. 2016 Mar;6(1):131-6. doi: 10.15171/apb.2016.019. Epub 2016 Mar 17. PMID: 27123428; PMCID: PMC4845551. 16: Hammami S, Li Z, Huang M, El Mokni R, Dhaouadi H, Yin S. New bioactive labdane diterpenoids from Marrubium aschersonii. Nat Prod Res. 2016 Oct;30(19):2142-8. doi: 10.1080/14786419.2016.1143828. Epub 2016 Feb 29. PMID: 26927415. 17: Nsuala BN, Enslin G, Viljoen A. "Wild cannabis": A review of the traditional use and phytochemistry of Leonotis leonurus. J Ethnopharmacol. 2015 Nov 4;174:520-39. doi: 10.1016/j.jep.2015.08.013. Epub 2015 Aug 18. PMID: 26292023. 18: Zerbe P, Chiang A, Dullat H, O'Neil-Johnson M, Starks C, Hamberger B, Bohlmann J. Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare. Plant J. 2014 Sep;79(6):914-27. doi: 10.1111/tpj.12589. Epub 2014 Jul 23. PMID: 24990389. 19: Popoola OK, Elbagory AM, Ameer F, Hussein AA. Marrubiin. Molecules. 2013 Jul 29;18(8):9049-60. doi: 10.3390/molecules18089049. PMID: 23899837; PMCID: PMC6269822. 20: Mughal UR, Mehmood R, Malik A, Ali B, Safder M, Tareen RB. Spiraeamide, new sphingolipid from Spiraea brahuica. J Asian Nat Prod Res. 2012;14(6):601-6. doi: 10.1080/10286020.2012.672975. PMID: 22587801.