Planta Med 2010; 76(7): 653-661
DOI: 10.1055/s-0029-1240898
Reviews
© Georg Thieme Verlag KG Stuttgart · New York

Plectranthus barbatus: A Review of Phytochemistry, Ethnobotanical Uses and Pharmacology – Part 1

Rawiya H. Alasbahi1 , Matthias F. Melzig2
  • 1Faculty of Pharmacy, Department of Pharmacognosy, University of Aden, Crater-Aden, Yemen
  • 2Institute of Pharmacy, Free University Berlin, Berlin, Germany
Weitere Informationen

Publikationsverlauf

received May 19, 2009 revised Dec. 7, 2009

accepted January 25, 2010

Publikationsdatum:
22. Februar 2010 (online)

Abstract

Plectranthus barbatus Andr. is one of the most important species of the genus Plectranthus L′ Herit. (Lamiaceae), with a wide variety of traditional medicinal uses in Hindu and Ayurvedic traditional medicine as well as in the folk medicine of Brazil, tropical Africa and China. The plant has therefore been an attractive target for intensive chemical and pharmacological studies up to now. This review presents data about the phytochemistry, ethnobotanical uses and pharmacology of Plectranthus barbatus as well as the pharmacology of its constituents. In addition to essential oil, abietane diterpenoids and 8,13-epoxy-labd-14-en-11-one diterpenoids are the main constituents found in Plectranthus barbatus. The major ethnobotanical uses are for intestinal disturbance and liver fatigue, respiratory disorders, heart diseases and certain nervous system disorders. Forskolin as one of the major constituents with its unique adenylyl cyclase activation that underlies the wide range of pharmacological properties could explain the different traditional uses of Plectranthus barbatus. Forskolin is involved in a number of patented pharmaceutical preparations used as over-the-counter drugs for the treatment of several ailments. However, the water-insoluble nature of forskolin limits its clinical usefulness. Forskolin thus served as a prototype for the development of 6-(3-dimethylaminopropionyl)forskolin hydrochloride (NKH477) as a potent water-soluble forskolin derivative that finds use in the therapy for a number of diseases especially of the cardiovascular system.

References

  • 1 Lukhoba C W, Simmonds M S J, Paton A J. Plectranthus: a review of ethnobotanical uses.  J Ethnopharmacol. 2006;  103 1-24
  • 2 Hara H. On the Asiatic species of the genus Rabdosia (Labiatae).  J Jpn Bot. 1972;  47 193-203
  • 3 Schultz C, Bossolani M P, Torres L M B, Lima-Landman M T R, Lapa A J, Souccar C. Inhibition of the gastric H+,K+-ATPase by plectrinone A, a diterpenoid isolated from Plectranthus barbatus Andrews.  J Ethnopharmacol. 2007;  111 1-7
  • 4 Jin Q D, He B H. Minor constituents from Coleus forskohlii.  Acta Bot Yunn. 1998;  20 469-473
  • 5 de Souza N J, Dohadwalla A N, Reden J. Forskolin: a labdane diterpenoid with antihypertensive, positive inotropic, platelet aggregation inhibitory, and adenylate cyclase activating properties.  Med Res Rev. 1983;  3 201-219
  • 6 Dubey M P, Srimal R C, Nityanand S, Dhawan B N. Pharmacological studies on coleonol, a hypotensive diterpene from Coleus forskohlii.  J Ethnopharmacol. 1981;  3 1-13
  • 7 Zelnik R, Lavie D, Levy E C, Wang A H J, Paul I C. Barbatusin and cyclobutatusin, two novel diterpenoids from Coleus barbatus Bentham.  Tetrahedron. 1977;  33 1457-1467
  • 8 Dubey M P, Srimal R C, Patnaik G K, Dhawan B N. Hypotensive and spasmolytic activities of coleonol, active principle of Coleus forskohlii Briq.  Indian J Pharmacol. 1974;  6 15
  • 9 Tandon J S, Dhar M M, Ramakumar S, Venkatesan K. Structure of coleonol, a biologically active diterpene from Coleus forskohlii.  Indian J Chem Sect B Org Chem Incl Med Chem. 1977;  15 B 880-883
  • 10 Bhat S V, Bajwa B S, Dornauer H, de Souza N J, Fehlhaber H W. Structures and stereochemistry of new labdane diterpenoids from Coleus forskohlii Briq.  Tetrahedron Lett. 1977;  19 1669-1672
  • 11 Ramakumar S, Venkatesan K, Tandon J S, Dhar M M. Molecular and crystal structure of coleonol, C22H34O7.  Z Kristallogr. 1985;  173 81-86
  • 12 Viswanathan N, Gawad D H. Identity of forskolin with coleonol.  Indian J Chem Sect B Org Chem Incl Med Chem. 1985;  24 B 583
  • 13 Saksena A K, Green M J, Shue H J, Wong J K, McPhail A T. Identity of coleonol with forskolin: structure revision of a base-catalysed rearrangement product.  Tetrahedron Lett. 1985;  26 551-554
  • 14 Ammon H P, Müller A B. Forskolin: from an ayurvedic remedy to a modern agent.  Planta Med. 1985;  51 473-477
  • 15 Ruedi P. Novel diterpenoids from leaf glands of Plectranthus barbatus (Labiatae). The absolute configuration of the 2-hydroxypropyl group in coleon E.  Helv Chim Acta. 1986;  69 972-984
  • 16 Yao C S, Shen Y H, Xu Y L. The chemical constituents of Coleus forskohlii.  Nat Prod Res Dev. 2002;  14 1-6
  • 17 Yao C S, Xu Y L. The diterpenoid quinones from Coleus forskohlii.  Chin Chem Lett. 2001;  12 339-342
  • 18 Kubo I, Matsumoto T, Tori M, Asakawa Y. Structure of plectrin, an aphid antifeedant diterpene from Plectranthus barbatus.  Chem Lett. 1984;  9 1513-1516
  • 19 de Albuquerque R L, Kentopff M R, Machado M I L, Silva M G V, Matos F J de A, Morais S M, Braz-Filho R. Abietane diterpenoids isolated from Plectranthus barbatus Andrews.  Quim Nova. 2007;  30 1882-1886
  • 20 Wang A H J, Paul I C, Zelnik R, Mizuta K, Lavie D. Structure and absolute stereochemistry of the diterpenoid barbatusin.  J Am Chem Soc. 1973;  95 598-600
  • 21 Wang A H J, Paul I C, Zelnik R, Lavie D, Levy E C. Structure and stereochemistry of cyclobutatusin, a diterpenoid containing a four-membered ring.  J Am Chem Soc. 1974;  96 580-581
  • 22 Ruedi P, Eugster C H. Structure of coleon E, a new diterpenoid methylenequinone from Coleus barbatus species (Labiatae).  Helv Chim Acta. 1972;  55 1994-2014
  • 23 Ruedi P, Eugster C H. Structure of coleon F.  Helv Chim Acta. 1973;  56 1129-1132
  • 24 Xu L L, Lu J, Li W J, Kong L Y. Studies on the chemical constituents in root of Coleus forskohlii.  Zhongguo Zhong Yao Za Zhi. 2005;  30 1753-1755
  • 25 Liu Y, Wu H, Wang X M, Liu J, Xing X. Use of coleon C extracted from Coleus as inhibitor for tumor growth and tumor cell proliferation. Chinese Patent CN 1899273 A; 2007. 
  • 26 Kelecom A, Dos Santos T C, Medeiros W L B. Secoabietane diterpenes from Coleus barbatus.  Phytochemistry. 1987;  26 2337-2340
  • 27 Kelecom A, Dos Santos T C. Cariocal, a new seco-abietane diterpene from the labiate Coleus barbatus.  Tetrahedron Lett. 1985;  26 3659-3662
  • 28 Mathela D K, Kharkwal H B, Mathela C S. Terpenoids of roots of Coleus forskohlii.  Fitoterapia. 1986;  57 299-301
  • 29 Kelecom A. Isolation, structure determination, and absolute configuration of barbatusol, a new bioactive diterpene with a rearranged abietane skeleton from the labiate Coleus barbatus.  Tetrahedron. 1983;  39 3603-3608
  • 30 Li S, Yang Q R, Wang X M, Zou G A, Liu Y W. Chemical constituents of Coleus forskohlii replanted to Tongcheng.  Zhongcaoyao. 2006;  37 824-826
  • 31 Kelecom A, Dos Santos T C, Medeiros W L B. On the structure and absolute configuration of (−)-20-deoxocarnosol.  An Acad Bras Cienc. 1986;  58 53-59
  • 32 Kelecom A. An abietane diterpene from the labiate Coleus barbatus.  Phytochemistry. 1984;  23 1677-1679
  • 33 Kelecom A. 6-β-Hydroxycarnosol, a new minor diterpene from the false boldo Coleus barbatus Bentham (Labiatae).  Quim Nova. 1983;  6 117-118
  • 34 Shah V, Bhat S V, Bajwa B S, Dornauer H, de Souza N J. The occurrence of forskolin in the Labiatae.  Planta Med. 1980;  39 183-185
  • 35 Gabetta B, Zini G, Danieli B. Minor diterpenoids of Coleus forskohlii.  Phytochemistry. 1989;  28 859-862
  • 36 Liu C, Yao W, Meng K, Liu Y, Zhang S, Zeng S, Lu S, Li H. Isolation and purification of forskolin and identification of its chemical structure and biological activity.  Shengwu Huaxue Yu Shengwu Wuli Jinzhan. 1992;  19 74-76
  • 37 Zhang X H, Zhang W, Jin Q D, Xu Y L. Spectral characteristics of forskolins (1).  Nat Prod Res Dev. 2005;  17 163-165
  • 38 Bhat S V, Dohadwalla A N, Bajwa B S, Dadkar N K, Dornauer H, de Souza N J. The antihypertensive and positive inotropic diterpene forskolin: effects of structural modifications on its activity.  J Med Chem. 1983;  26 486-492
  • 39 Xu L L, Kong L Y. Labdane diterpenoids from Coleus forskohlii (Willd.) Briq.  J Integr Plant Biol. 2006;  48 478-481
  • 40 Wu M, Lai G F, Jin Q D, Xu Y L. Spectral characteristic property of forskolins (2).  Nat Prod Res Dev. 2005;  17 (Suppl.) 17-19 22
  • 41 Jin Q D, Xie X H, Mu Q Z. Study on the chemical constituents from Coleus forskohlii Briq.  Nat Prod Res Dev. 1990;  2 6-9
  • 42 Carpy A, Leger J M, Tandon J S, Saxena A K. Molecular and crystal structure of coleonol-B, C22H34O7.  Z Kristallogr. 1991;  194 229-233
  • 43 Prakash O, Roy R, Tandon J S, Dhar M M. Carbon-13 and proton two-dimensional NMR study of diterpenoids of Coleus forskohlii.  Magn Reson Chem. 1988;  26 117-119
  • 44 Xu L L, Kong L Y. Isolation and identification of labdane diterpenoids from the roots of Coleus forskohlii.  Chin J Nat Med. 2004;  2 344-347
  • 45 Yang Q R, Wu H Z, Wang X M, Zou G A, Liu Y W. Three new diterpenoids from Coleus forskohlii Briq.  J Asian Nat Prod Res. 2006;  8 355-360
  • 46 Roy R, Mishra A, Varma N, Tandon J S, Saux M, Carpy A. Minor diterpenes from Coleus forskohlii.  Phytochemistry. 1993;  34 1577-1580
  • 47 Xu Y L, Jin Q D, Liu J. Spectral characteristics of forskolins (3).  Nat Prod Res Dev. 2006;  18 (Suppl.) 79-81 97
  • 48 Khandelwal Y, Jotwani P K, Inamdar P K, de Souza N J, Rupp R H. Isolation, structure elucidation, and synthesis of 1-deoxyforskolin.  Tetrahedron. 1989;  45 763-766
  • 49 Shen Y H, Yao C S, Xu Y L. New diterpenoids from Coleus forskohlii.  Chin Chem Lett. 2002;  13 740-743
  • 50 Shan Y P, Wang X B, Kong L Y. Forskolin G.  Acta Crystallogr Sect E Struct Rep Online. 2006;  E62 o2408-o2410 http://journals.iucr.org/e/issues/2006/06/00/hk2036/index.html
  • 51 Shen Y H, Xu Y L. Two new diterpenoids from Coleus forskohlii.  J Asian Nat Prod Res. 2005;  7 811-815
  • 52 Yang W M, Jin Q D, Xu Y L. Spectral characteristics of forskolins (4).  Nat Prod Res Dev. 2007;  19 991-994
  • 53 Jauhari P K, Katti S B, Tandon J S, Dhar M M. Coleosol – a new diterpene from Coleus forskohlii.  Indian J Chem Sect B Org Chem Incl Med Chem. 1978;  16 B 1055-1057
  • 54 Singh S, Painuly P, Tandon J S. Diterpenes from Coleus forskohlii: stereochemistry of the carbonyl chromophore.  Indian J Chem Sect B Org Chem Incl Med Chem. 1984;  23 B 952-955
  • 55 Katti S B, Jauhari P K, Tandon J S. New diterpenes from Coleus forskohlii: structures of the diterpenes, coleonol-D, coleol and coleonone.  Indian J Chem Sect B Org Chem Incl Med Chem. 1979;  17 B 321-323
  • 56 Painuly P, Katti S B, Tandon J S. Diterpenes from Coleus forskohlii: structures of coleonol-E and coleonol-F.  Indian J Chem Sect B Org Chem Incl Med Chem. 1979;  18 B 214-216
  • 57 Tandon J S, Jauhari P K, Singh R S, Dhar M M. Structures of three new diterpenes, coleonol B, coleonol C and deoxycoleonol isolated from Coleus forskohlii.  Indian J Chem Sect B Org Chem Incl Med Chem. 1978;  16 B 341-345
  • 58 Shan Y P, Kong L Y. Isolation and identification of terpenes from Coleus forskohlii.  Chin J Nat Med. 2006;  4 271-274
  • 59 Tandon J S, Roy R, Balachandran S, Vishwakarma R A. Epi-deoxycoleonol, a new antihypertensive labdane diterpenoid from Coleus forskohlii.  Bioorg Med Chem Lett. 1992;  2 249-254
  • 60 Sashidhara K V, Rosaiah J N, Kumar A, Bid H K, Konwar R, Chattopadhyay N. Cell growth inhibitory action of an unusual labdane diterpene, 13-epi-sclareol in breast and uterine cancers in vitro.  Phytother Res. 2007;  21 1105-1108
  • 61 Shan Y, Xu L, Lu Y, Wang X, Zheng Q, Kong L, Niwa M. Diterpenes from Coleus forskohlii (WILLD.) BRIQ. (Labiatae).  Chem Pharm Bull. 2008;  56 52-56
  • 62 Liu Y, Wang X M, Wu H. Main components of Coleus forskohlii extract and relevant extraction method. Chinese Patent CN 1944384 A; 2007. 
  • 63 Shan Y, Wang X, Zhou X, Kong L, Niwa M. Two minor diterpene glycosides and an eudesman sesquiterpene from Coleus forskohlii.  Chem Pharm Bull. 2007;  55 376-381
  • 64 Kerntopf M R, de Albuquerque R L, Machado M I L, Matos F J A, Craveiro A A. Essential oils from leaves, stems and roots of Plectranthus barbatus Andr. (Labiatae) grown in Brazil.  J Essent Oil Res. 2002;  14 101-102
  • 65 Mancini B, Rubino C L, Pozetti G L, Mancini M A D. Chromatographic study of essential oils from plants of Araraquara region. 1. Thin-layer and vapor-phase chromatographic analysis of essential oil from leaves of Coleus barbatus Labiatae.  Rev Fac Farm Odontol Araraquara. 1972;  6 41-46
  • 66 Muhayimana A, Chalchat J C, Garry R P. Chemical composition of essential oils of some medicinal plants from Rwanda.  J Essent Oil Res. 1998;  10 251-259
  • 67 Chalchat J C, Garry R P, Muhayimana A. Aromatic plants of Rwanda. Chemical composition of two Labiaceae, Plectranthus barbatus and Plectranthus sylvestris.  Riv Ital EPPOS. 1996;  7 665-674
  • 68 Ahmed B, Vishwakarma R A. Coleoside, a monoterpene glycoside from Coleus forskohlii.  Phytochemistry. 1988;  27 3309-3310
  • 69 Roy R, Vishwakarma R A, Varma N, Tandon J S. Coleonolic acid, a rearranged ursane triterpenoid from Coleus forskohlii.  Tetrahedron Lett. 1990;  31 3467-3470
  • 70 Tandon J S, Katti S B, Rueedi P, Eugster C H. Crocetin dialdehyde from Coleus forskohlii Briq., Labiatae.  Helv Chim Acta. 1979;  62 2706-2707
  • 71 Shah V C, D'Sa A S, de Souza N J. Chonemorphine, stigmasterol, and ecdysterone: steroids isolated through bioassay-directed plant screening programs.  Steroids. 1989;  53 559-565
  • 72 Ahmed B, Merotra R. Coleoside-B: a new phenolic glycoside from Coleus forskohlii.  Pharmazie. 1991;  46 157-158
  • 73 Mendes B G, Machado M J, Falkenberg M. Screening of glycolipids in medicinal plants.  Rev Bras Farmacognosia. 2006;  16 568-575
  • 74 Matu E N, van Staden J. Antibacterial and anti-inflammatory activities of some plants used for medicinal purposes in Kenya.  J Ethnopharmacol. 2003;  87 35-41
  • 75 Camara C C, Nascimento N R, Macedo-Filho C L, Almeida F B, Fonteles M C. Antispasmodic effect of the essential oil of Plectranthus barbatus and some major constituents on the guinea-pig ileum.  Planta Med. 2003;  69 1080-1085
  • 76 Ding X, Staudinger J L. Induction of drug metabolism by forskolin: the role of the pregnane X receptor and the protein kinase A signal transduction pathway.  J Pharmacol Exp Ther. 2005;  312 849-856
  • 77 Almeida F C, Lemonica I P. The toxic effects of Coleus barbatus B. on the different periods of pregnancy in rats.  J Ethnopharmacol. 2000;  73 53-60
  • 78 Vigneron M, Deparis X, Deharo E, Bourdy G. Antimalarial remedies in French Guiana: a knowledge attitudes and practices study.  J Ethnopharmacol. 2005;  98 351-360
  • 79 Tabuti J R, Lye K A, Dhillion S S. Traditional herbal drugs of Bulamogi, Uganda: plants, use and administration.  J Ethnopharmacol. 2003;  88 19-44

Prof. Dr. Matthias F. Melzig

Institute of Pharmacy
Free University Berlin

Königin-Luise-Str. 2 + 4

14195 Berlin

Germany

Telefon: + 49 30 83 85 14 51

Fax: + 49 30 83 85 14 61

eMail: melzig@zedat.fu-berlin.de

    >