A review of the chemical and pharmacological aspects of the genus marrubium

Current Pharmaceutical Design

Volumn 16, Issue 31, 2010, Pages 3503-3518

  Meyre Silva, Christiane ^a   Cechinel Filho, Valdir ^a  

^a UNIVERSIDADE DO VALE DO ITAJAÍ   (Brazil)

Author keywords

Analgesic and anti inflammatory effects; Antimicrobial; Chemical composition; Essential oils; Ethnopharmacology; Labdane terpenes; M. vulgare; Marrubium

Indexed keywords

MARRUBIUM ALTERNIDENS EXTRACT; MARRUBIUM ALYSSON EXTRACT; MARRUBIUM ASTRACANICUM EXTRACT; MARRUBIUM BOURGAEI EXTRACT; MARRUBIUM CORDATUM EXTRACT; MARRUBIUM CYLLENEUM EXTRACT; MARRUBIUM DESERTI EXTRACT; MARRUBIUM GLOBOSUM EXTRACT; MARRUBIUM INCANTUM EXTRACT; MARRUBIUM PEREGRINUM EXTRACT; MARRUBIUM POLYDON EXTRACT; MARRUBIUM RADIATUM EXTRACT; MARRUBIUM VELUTINUM EXTRACT; MARRUBIUM VULGARE EXTRACT; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BRAZIL; CHEMICAL COMPOSITION; DRUG ACTIVITY; DRUG ISOLATION; ETHNOPHARMACOLOGY; MARRUBIUM; MARRUBIUM ALTERNIDENS; MARRUBIUM ALYSSON; MARRUBIUM ASTRACANICUM; MARRUBIUM BOURGAEI; MARRUBIUM CATARIIFOLIUM; MARRUBIUM CORDATUM; MARRUBIUM CUNEATUM; MARRUBIUM CYLLENEUM; MARRUBIUM DESERTI; MARRUBIUM FRIVALDSKYANUM; MARRUBIUM GLOBOSUM; MARRUBIUM INCANTUM; MARRUBIUM LEONUROIDES; MARRUBIUM PARVIFLORUM; MARRUBIUM PEREGRINUM; MARRUBIUM POLYDON; MARRUBIUM PROPINQUUM; MARRUBIUM RADIATUM; MARRUBIUM SERICEUM; MARRUBIUM SUPINUM; MARRUBIUM THESSALUM; MARRUBIUM TRACHYTICUM; MARRUBIUM VELUTINUM; MEDICINAL PLANT; NONHUMAN; PHYTOCHEMISTRY; PRIORITY JOURNAL;

HUMANS; MARRUBIUM; MEDICINE, TRADITIONAL; MOLECULAR STRUCTURE; PLANT PREPARATIONS;

EID: 78649976086     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161210793563392     Document Type: Article

References (90)

1. Harvey AL. Natural products in drug development. Drug Discov Today 2008; 13(19/20): 894-901.
2. Butler MS. Natural products to drugs: natural product-derived compounds in clinical trials. Nat Prod Rep 2008; 25(3): 475-516.
3. Gurib-Fakim A. Medicinal plants: traditions of yesterday and drugs of tomorrow. Mol Aspects Med 2006; 27: 1-93.
4. Malheiros A, Meyre-Silva C, Niero R, Cechinel-Filho V. In: Fár-macos e medicamentos uma abordagem multidisciplinar, Ed. Santos 2010, pp. 10-56.
5. Fátima A, Modolo LV, Sanches ACCS, Porto RR. Wound healing agents: the role of natural and non-natural products in drug development. Mini Rev Med Chem 2008; 8(9): 879-888.
6. Balmé F. Plantas Medicinais. São Paulo: Hemus 1982.
7. Di Vicenzi M, Maialetti F. Marrubiumvulgare L. Fitoterapia 1995; 16(3): 207.
8. Kurbatova NV, Muzychkina RA, Mukhitdinov NM, Parshina GN. Comparative phytochemical investigation of the composition and content of biologically active substances in Marrubium vulgare and M. alternides. Chem Nat Comp 2003; 39(5): 501-502.
9. Piccoli PN, Bottini R. Accumulation of the labdane diterpene marrubiin in glandular trichome cells alog the ontogeny of Marru-bium vulgare plants. Plant Growth Regul 2008; 56: 71-76.
10. Appleton RA, Fulke JWB, Henderson MS, McCrindle R. The stereochemistry of marrubiin. J Chem Soc (C) 1967; 1943-1948.
11. Henderson MS, McCrindle R. Premarrubiin. A diterpenoid from Marrubium vulgare L. J. Chem. Soc. (C) 1969; 2014-2015.
12. Sahpaz S, Garbacki N, Tits M, Bailleul F. Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare. J Ethnopharmacol 2002; 79: 389-392.
13. Krejci I, Zadina R. Choleretic action of marrubiin and marrubic acid. Planta Med 1959; 7: 1-7.
14. Saleh MRI, Sarg TM, Metwally AM, Rakha AA. Chemical constituents from Marrubium alysson. Planta Med 1981; 41(2): 202-203.
15. Savona G, Piozzi F, Aránguez LM, Rodriguéz B. Diterpenes from Marrubium sericeum, Marrubium supinum and Marrubium alys-son. Phytochemistry 1979; 18: 859-860.
16. Çalis I, Hosny M, Khalifa T, Ruedi P. Phenylpropanoid glycosides from Marrubium alysson. Phytochemistry 1992; 31(10): 3624-3626.
17. Havey E, Samia A, Patrick G, et al. Antimicrobial and cytotoxic activity of Marrubium alysson and Retama Raetam grown in Tunisia. Pak. J. Biol. Sci. 2007; 15(10): 1759-1762.
18. Janicsák G, Veres K, Kakasy AZ, Máthé I. Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae. Bio-chem Syst Ecol 2006; 34: 392-396.
19. Zafari SM, Akhani H. Plants of Jahan nama protected area, Goletan Province. N Iran Pak J Bot 2008; 40(4): 1533-1554.
20. Lida A, Tanaka Y, Mihara T, et al. Marrubinones A and B, labdane diterpenoids from Marrubium astracanicum (Labiatae). Chem Pharm Bull 1995; 43(9): 1454-1457.
21. Nik ZB, Mirza M. Composition of the essential oil of Marrubium astracanicum Jacq J. Essential Oil Res 2003; 15: 342-343.
22. Javidnia K, Miri R, Soltani M, Khosravi AR. Constituents of the essential oil of Marrubium astracanicum jacq. from Iran. J Essential Oil Res 2007; 19(6): 559-561.
23. Morteza-Semnani K, Saeedi M. The essential oil of Marrubium astracanicum Jacq. from Iran. J Essential Oil Res 2004; 7(3): 239-242.
24. Teimori M, Khavari-Nejad RA, Yassa N, Nejadsatari T. Analysis of the essential oil of Marrubium crassidens Bioos. and M. astra-canicum Jacq. J Appl Sci 2008; 8(9): 1793-1795.
25. Demirci B, Baser KHC, Kirimer N. Composition of the essential oil of Marrubium bourgaei ssp. caricum P.H. Davis. J Essential Oil Res 2004; 16(2): 133-134.
26. Kurkcuoglu M, Baser KHC, Tosun A, Dogan E, Duman H. Essential oil composition of an endemic species of Tukey: Marrubium bourgaei Boiss. Ssp bourgaei (Labiatae). J Essen Oil Res 2007; 19(1): 34.
27. Popa DP, Salei LA. Diterpenoids of the genus Marrubium (hore-hound). Rastitel'nye Resursy 1973; 9(3): 384-387.
28. Cigremis Y, Kart A, Karaman M, Erdag D. Attenuation of ische-mia-reperfusion injury with Marrubium cordatum treatment in ovarian torsion-detorsion model in rabbits. Fertil Sterill 2010; 93(5): 1455-1463.
29. Nik ZB, Mirza M, Shahmir F. Essential oil of Marrubium cunea-tum Russel and its secretory elements. Flavour Fragran J 2004; 19(3): 233-234.
30. Grassia A, Senatore F, Arnold NA, et al. Chemical composition of the essential oils from aerial parts of two Marrubium sp. (La-miaceae). Polish J Chem 2008; 80(4): 623-628.
31. Karioti A, Heilmann J, Skaltsa H. Labdane diterpenes from Marru-bium velutim and Marrubium cylleneum. Phytochemistry 2005; 66: 1060-1066.
32. Karioti A, Protopappa A, Megoulas N, Skaltsa H. Identification of tyrosinase inhibitors from Marrubium velutim and Marrubium cyllenetum. Bioorg Med Chem 2007; 15: 2708-2714.
33. Rigano D, Grassia A, Bruno M, et al. Labdane diterpenoids from Marrubium globosum SSP. libanoticum. J Nat Prod 2006; 69(5): 836-838.
34. Karioti A, Skopeliti M, Tsitsilonis O, Heilmann J, Skaltsa H. Cytotoxicity and immunomodulating characteristic of labdane diterpenes from Marrubium cylleneum and Marrubium velutinum. Phytochemistry 2007; 68: 1587-1594.
35. Laouer H, Yabrir B, Djeridane A, Yousfi M, Beldovini N, La-mamra M. Composition, antioxidant and antimicrobial activities of the essential of Marrubium desserti De Noé. Nat Product Commun 2009; 4(8): 1133-1138.
36. Markovska YK, Dimitrov DS. The effect of leaf age on gas exchange and malate accumulation in C3-CAM plant Marrubium fri-valdszkyanum. Photosynthetica 2001; 39(2): 191-195.
37. Savona G, Bruno M, Rodriguez B. Preperegrinine, a prefuranic labdane diterpene from Marrubium friwaldskyanum. Phytochemis-try 1984; 23(1): 191-192.
38. Rigano D, Formisano C, Basile A, et al. Antibacterial activity of flavonoids and phenylpropanoids from Marrubium globosum SSP. libanoticum Phytother Res 2007; 21(4): 395-397.
39. Yazici H, Kiliç M, Solak M. Biosorption of copper (II) by Marru-bium globosum sbsp. globosum leaves powder: Effect of chemical pretreatment. J Hazard Mater 2008; 151: 669-675.
40. Takeda Y, Yanagihara K, Masuda T, et al. Labdane diterpenoids from Marrubium globosum ssp. globosum. Chem Pharm Bull 2000; 48(8): 1234-1235.
41. Rigano D, Grassia A, Borrelli F, et al. Phytochemical and Pharmacological Studies on the acetonic extract of Marrubium globosum ssp. libanoticum. Planta Med 2006; 7(6): 575-578.
42. Rigano D, Arnold NA, Bruno M, et al. Phenolic compounds of Marrubium globosum ssp. libanoticum from Lebanon. Biochem Syst Ecol 2006; 34: 256-258.
43. Rigano D, Aviello G, Bruno M, et al. Antispamodic effects and structure-activity relationships of labdane diterpenoids from Mar-rubium globosum SSP. libanoticum. J Nat Prod 2009; 72(8): 1477-1481.
44. Sarikurkcu C, Tepe B, Daferera D, Polissiou M, Harmandar M. Studies on the antioxidant activity of the essential oil and methanol extract of Marrubium globosum subsp. globosum (lamiaceae) by three different chemical assays. Bioresour Technol 2008; 99: 4239-4246.
45. Petrović S, Pavlović M, Maksimovi Z, et al. Composition and antimicrobial activity of Marrubium incanum Desr. (Lamiaceae) essential oil. Nat Prod Commun 2009; 4(3): 431-434.
46. Khanavi M, Ghasemian L, Motlagh L, Elham H, Hadjiakhoondi A, Shafiee A. Chemical composition of the essential oils of Marru-bium parviflorum Fisch. & C. A. and Marrubium vulgare L. from Iran. Flavour Fragrance J 2005; 20(3): 324-326.
47. Bal Y, Kaban S, Kirimer N, Baser KHC. Composition of the essential oil of Marrubium parviflorum Fisch. Et Mey. Subsp. oli-godon. J Essent Oil Res 1999; 11(3): 300-302.
48. Bal Y. Terpenoids and a flavone from Marrubium parviflorum. Marmara Universitesi Eczacilik Dergisi 1989; 5(1): 89-91.
49. Bal Y, Kaban S. GC-MS analysis of Marrubium parviflorum oligodon. Fitoterapia 1995; 66(2): 179-180.
50. Bal Y, Kaban S, Nizami SS. Anatolione: a new diterpene from Marrubium parviflorum Oligodon. Pak J Sci Ind Res 1995; 38(3-4): 144-145.
51. Salei LA, Popa DP, Lazur'evskii GV. Phenolic compounds and diterpenoids from Marrubium peregrinum. Chem Nat Comp 1972; 5: 156.
52. Telek E, Toth L, Botz L, Mathe I. Chemical tests with Marrubium species. Data to Marrubii herba official in Pharmacopeia Hun-garica. Acta Pharma Hung 1997; 67(1): 3137.
53. Salei LA, Popa DP, Lazur'evskii GV. 4',5,6,7-tetramethoxyflavone from Marrubium peregrinum. Him Prir Soedin 1969; 5: 182-183.
54. Nagy M, Gergel D, Grancai D, Novomesky P, Ubik K. Antilipop-eroxidative activity of some phenolic constituents from Marrubium peregrinum L. Farm Obz 1996; 65(12): 283-285.
55. Hennebelle T, Sahpaz S, Skaltsounis AL, Bailleul F. Phenolic compounds and diterpenoids from Marrubium peregrinum. Bio-chem Syst Ecol 2007; 35: 624-626.
56. Salei LA, Popa DP, Lazur'evskii GV. 4',5,6,7-Tetramethoxy-flavone from Marrubium peregrinum. Prirodnykh Soedinenii 1969; 5(3): 182-183.
57. Salei LA, Popa DP, Lazur'evskii GV. Diterpenoids from Marru-bium peregrinum. Khimiya Prirodnykh Soedinenii 1966; 2(4): 249-251.
58. Natic ARH, Porzel A, Seifert K. Polyodonine, a prefuranic labdane diterpene from Marrubium polydon. Phytochemistry 1995; 40(5): 1575-1576.
59. Jawad AM, Jaffer AH, Alnaib A, Naji A. Antimicrobial activity of sesquiterpene lactone and alkaloid from Iraqi plants. Pharm Biol 1988; 26(4): 185-188.
60. Tajbakhsh M, Khalizadeh M, Mohammad A, Rineh A, Balou J. Essential oils of Marrubium anisodon C. Koch and Marrubium propinquum Fish. Et C. A. Mey., growing wild in Iran. J Essent Oil Res 2007; 20(2): 161-162.
61. Loizzo MR, Saabb AM, Tundisa R, et al. In vitro inhibitory activities of plants used in Lebanon traditional medicine against angio-tensin converting enzyme (ACE) and digestive enzymes related diabetes. J Ethnopharmacol 2008; 119: 109-116.
62. El Bardai S, Lyoussi B, Wibo M, Morel N. Comparative study of the antihypertensive activity of Marrubium vulgare and of the di-hydropyridine calcium antagonist amlodipine in spontaneously hypertensive rat. Clin Exp Hypertens 2004; 26(6): 465-474.
63. Argyropoulou C, Karioti A, Skaltsa H. Labdane diterpenes from Marrubium thessalum. Phytochemistry 2009; 70(5): 635-640.
64. Çitoglu GS, Aksit F. Occurrence of marrubiin and ladanein in Marrubium trachyticum Boiss. From Turkey. Biochem Syst Ecol 2002; 30: 885-886.
65. Karioti A, Skaltsa H, Heilmann J, Sticher O. Acylated flavonoid and phenylethanoid glycosides from Marrubium velutim. Phyto-chemistry 2003; 64: 655-660.
66. Lorenzi H, Matos FJA. Plantas medicinais do Brasil: nativas e exóticas. Nova Odessa: Instituto Plantarum, 2002.
67. Knoess W, Zapp J. Accumulation of furam labdane diterpenes in Marrubium vulgare and Leonurus cariíaca. Planta Med 1998; 64(4): 357-361.
68. Rodrigues CA, Savi AOS, V Schlemper, Reynaud F, Cechinel-Filho V. An improved extraction of marrubiin from Marrubium vulgare. Chromatographia 1998; 47(7/8): 449-450.
69. Nawwar MAM, El-Mousallamy AMD, Barakat HH, Buddrus J, Linscheid M. Flavonoid lactates from leaves of Marrubium vul-gare. Phytochemistry 1989; 28(11): 3201-3206.
70. Sahpaz S, Garbacki N, Tits M, Bailleul F. Isolation and pharmacological activity of phenylpropanoid esters from Marrubium vulgare. J Ethnopharmacol 2002; 79: 389-392.
71. Popa DP, Pasechnik GS. Structure of vulgarol - new diterpenoid from Marrubium vulgare. Him Prir Soedin 1975; 11(6): 722-728.
72. Popa DP, Pasechnik GS. Marrubiol, a new diterpenoid from Mar-rubium vulgare. Him Prir Soedin 1968; 4(6): 345-348.
73. Kowalewski Z, Matlawska I. Flavonoid compounds in the herb Marrubium vulgare. Herba Polonica 1978; 24(4): 183-186.
74. Amer MMA. Constituents of the aerial parts of Marrubium vulgare L. J Pharm Sci 1993; 9(1): 92-98.
75. Herrera-Arellano A, Aguila-Santamaria L, Garcia-Hernández B, Nicasio-Torres P, Tortoriello J. Clinical Trial of Cecropia obtusifo-lia and Marrubium vulgare leaf extracts on blood glucose and serum lipids in type 2 diabetics. Phytomedicine 2004; 11: 561-566.
76. Al-Bakri AG, Afifi FG. Evaluation of antimicrobial activity of selected plant extracts by rapid XTT colomimetry and bacterial enumeration. J Microbiol Methods 2007; 68: 19-25.
77. Masoodi MH, Bahar A, Zargar IM, Khan AS, Khan S, Singh P. Antibacterial activities of whole plant extract of Marrubium vul-gare. African J. Biotechnol 2008; 7(2): 86-87.
78. Quave CL, Plano LRW, Pantuso T, Bennett BC. Effects of extracts from Italian medicinal plants on planktonic growth, biofilm formation and adherence of methicilin-resistant Staphylococcus aureus. J Ethnopharmacol 2008; 118: 418-428.
79. Vanderjagt TJ, Ghattas R, Vanderjagt DJ, Crossey M, Glew RH. Comparison of the total antioxidant content of 30 widely used medicinal plants of New Mexico. Life Sci 2002; 70(9): 1035-1040.
80. Berrougui H, Isabelle M, Cherki M, Khali A. Marrubium vulgare extract inhibits human-LFL oxidation and enhances HDL-mediated cholesterol effux in THP-1 macrophage. Life Sci 2006; 80, 105-112.
81. De Souza MM, De Jesus RAP, Cechinel-Filho V, Schlemper V. Analgesic profile of hydroalcoholic extract obtained from Marru-bium vulgare. Phytomedicine 1998; 5(2): 103-107.
82. De Jesus RAP, Cechinel-Filho V, Oliveira AE, Schlemper V. Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare. Phytomedicine 1999; 7(2), 111-115.
83. Meyre-Silva C, Yunes RA, Schlemper V, Campos-Buzzi F, Cechi-nel-Filho V. Analgesic potential of marrubiin derivates, a bioactive diterpene present in Marrubium vulgare (Lamiaceae). Farmaco 2005; 60(4): 321-326.
84. El Bardai S, Wibo M, Hamaide M, Lyoussi B, Quetin-Leclercq J, Morel N. Characterisation of marrubenol, a diterpene extracted from Marrubium vulgare, as an L-type calcium channel blocker. Brit J Pharmacol 2003; 140: 1211-1216.
85. Stulzer HK, Tagliari MP, Zampirolo JA, Cechinel-Filho V, Schlemper V. Antiedematogenic effect of marribiin obtained from Marrubium vulgare. J Ethnopharmacol 2006; 108(3): 379-384.
86. Karryev MO, Bairyev CB, Ataeva AS. Some therapeutic properties and phytochemistry of common horehound. Seriya Biologicheskikh Nauk 1976; (3): 86-88.
87. Asadipour A, Mehrabani M, Nazeri V, Tabarraii M. Composition of the essential oil of Marrubium vulgare L. Ulum-i Daroei 2004; 2: 77-82.
88. Khanavi M, Ghasemian L, Motlagh EH, Hadjiakhoondi A, Shafiee A. Chemical composition of the essential oils of Marrubium parvi-florum Fisch. & C. A. and Marrubium vulgare. Flavour Fragrance J 2005; 20(3): 324-326.
89. Belhattab R, Larous L, Figueiredo AC, et al. Essential oil composition and glandular trichomes of Marrubium vulgare L. growing wild in Algeria. J Essent Oil Res 2006; 18(4): 369-373.
90. Brand HM, Goedbloed AF. Marrubiin and composition for reducing snoring, package and method. Patent WO2007018432, Feb 15, 2007.