Abietane Diterpenes of the Genus Plectranthus sensu lato

. 2021 Dec 28 ; 27 (1) : . [epub] 20211228

Jazyk angličtina Země Švýcarsko Médium electronic

Typ dokumentu časopisecké články, metaanalýza, přehledy

Perzistentní odkaz   https://www.medvik.cz/link/pmid35011401

Grantová podpora
MUNI/1688/2020 Masarykova Univerzita

Plectranthus (Lamiaceae), which-according to the latest systematic revision-includes three separate genera (Coleus, Plectranthus sensu stricto, and Equilabium), is a genus widely used in traditional medicine-mainly in the treatment of various ailments of the digestive tract, respiratory tract, and skin. Many species of Plectranthus s.l. have been shown to produce phenolic compounds and terpenes. Diterpenes, especially those of the abietane class, are the most studied group of secondary metabolites found in Plectranthus s.l., which is characterized by a significant structural diversity arising from the oxygenation and further rearrangement of the basic tricyclic abietane skeleton to a complete aromatization of the ring system. This review summarizes the known information on abietane diterpenes, showing their structures, sources, and biosynthesis. A classification of these compounds into nine groups, according to the arrangement of their ring C, is used. Royleanones, spirocoleons, and hydroquinones are the largest classes of abietane diterpenes, covering more than 70% of all the compounds reviewed.

Zobrazit více v PubMed

Süntar I. Importance of ethnopharmacological studies in drug discovery: Role of medicinal plants. Phytochem. Rev. 2020;19:1199–1209. doi: 10.1007/s11101-019-09629-9. DOI

Paton A., Mwanyambo M., Culham A. Phylogenetic study of Plectranthus, Coleus and allies (Lamiaceae): Taxonomy, distribution and medicinal use. Bot. J. Linn. Soc. 2018;188:355–376. doi: 10.1093/botlinnean/boy064. DOI

Paton A.J., Mwanyambo M., Govaerts R.H.A., Smitha K., Suddee S., Phillipson P.B., Wilson T.C., Forster P.I., Culham A. Nomenclatural changes in Coleus and Plectranthus (Lamiaceae): A tale of more than two genera. PhytoKeys. 2019;129:1–158. doi: 10.3897/phytokeys.129.34988. PubMed DOI PMC

Van Jaarsveld E., Thomas V. The Southern African Plectranthus: And the Art of Turning Shade to Glade. Fernwood Press; Pretoria, South Africa: 2006.

Lukhoba C.W., Simmonds M.S.J., Paton A.J. Plectranthus: A review of ethnobotanical uses. J. Ethnopharmacol. 2006;103:1–24. doi: 10.1016/j.jep.2005.09.011. PubMed DOI

Rice L.J., Brits G.J., Potgieter C.J., van Staden J. Plectranthus: A plant for the future? S. Afr. J. Bot. 2011;77:947–959. doi: 10.1016/j.sajb.2011.07.001. DOI

Grayer R.J., Eckert M.R., Lever A., Veitch N.C., Kite G.C., Paton A.J. Distribution of exudate flavonoids in the genus Plectranthus. Biochem. Syst. Ecol. 2010;38:335–341. doi: 10.1016/j.bse.2010.01.014. DOI

Abdel-Mogib M., Albar H.A., Batterjee S.M. Chemistry of the genus Plectranthus. Molecules. 2002;7:271–301. doi: 10.3390/70200271. DOI

Waldia S., Joshi B.C., Pathak U., Joshi M.C. The Genus Plectranthus in India and Its Chemistry. Chem. Biodivers. 2011;8:244–252. doi: 10.1002/cbdv.201000048. PubMed DOI

Rijo P., Faustino C., Simões M.F. Antimicrobial natural products from Plectranthus plants. In: Méndez-Vilas A., editor. Microbial Pathogens and Strategies for Combating Them: Science, Technology and Education. Formatex; Badajoz, Spain: 2013. pp. 922–931.

Grayer R.J., Paton A.J., Simmonds M.S., Howes M.J.R. Differences in diterpenoid diversity reveal new evidence for separating the genus Coleus from Plectranthus. Nat. Prod. Rep. 2021;38:1720–1728. doi: 10.1039/D0NP00081G. PubMed DOI

Cretton S., Saraux N., Monteillier A., Righi D., Marcourt L., Genta-Jouve G., Wolfender J.L., Cuendet M., Christen P. Anti-inflammatory and antiproliferative diterpenoids from Plectranthus scutellarioides. Phytochemistry. 2018;154:39–46. doi: 10.1016/j.phytochem.2018.06.012. PubMed DOI

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. doi: 10.1016/S0040-4020(01)88671-3. DOI

Katti S.B., Rüedi P., Eugster C.H. Diterpenoide Chinomethane, vinyloge Chinone und ein Phyllocladan-Derivat aus Plectranthus purpuratus HARV. (Labiatae) Helv. Chim. Acta. 1982;65:2189–2197. doi: 10.1002/hlca.19820650724. DOI

Ladeiras D., Monteiro C.M., Pereira F., Reis C.P., Afonso C.A.M., Rijo P. Reactivity of Diterpenoid Quinones: Royleanones. Curr. Pharm. Des. 2016;22:1682–1714. doi: 10.2174/1381612822666151211094521. PubMed DOI

van Zyl R.L., Khan F., Edwards T.J., Drewes S.E. Antiplasmodial activities of some abietane diterpenes from the leaves of five Plectranthus species. S. Afr. J. Sc. 2008;104:62–64.

Bao H., Zhang Q., Ye Y., Lin L. Naturally occurring furanoditerpenoids: Distribution, chemistry and their pharmacological activities. Phytochem. Rev. 2017;16:235–270. doi: 10.1007/s11101-016-9472-2. DOI

García P.A., de Oliveira A.B., Batista R. Occurrence, biological activities and synthesis of kaurane diterpenes and their glycosides. Molecules. 2007;12:455–483. doi: 10.3390/12030455. PubMed DOI PMC

González M.A. Aromatic abietane diterpenoids: Their biological activity and synthesis. Nat. Prod. Rep. 2015;32:684–704. doi: 10.1039/C4NP00110A. PubMed DOI

Otto A., Wilde V. Sesqui-, Di-, and Triterpenoids as Chemosystematic Markers in Extant Conifers—A Review. Bot. Rev. 2001;67:141–238. doi: 10.1007/BF02858076. DOI

Talapatra S.K., Talapatra B. Chemistry of Plant Natural Products. Springer; Berlin, Germany: 2015. Diterpenoids (C20) pp. 469–510.

Lin L.G., Ung C.O.L., Feng Z.L., Huang L., Hu H. Naturally Occurring Diterpenoid Dimers: Source, Biosynthesis, Chemistry and Bioactivities. Planta Med. 2016;82:1309–1328. doi: 10.1055/s-0042-114573. PubMed DOI

Schmid J.M., Rüedi P., Eugster C.H. Diterpenoide Drüsenfarbstoffe aus Labiaten: 22 neue Coleone und Royleanone aus Plectranthus lanuginosus. Helv. Chim. Acta. 1982;65:2136–2163. doi: 10.1002/hlca.19820650721. DOI

Arihara S., Rüedi P., Eugster C.H. Neue spiro-cyclopropyl-cyclohexendion-diterpene: Coleone M, N, P, Q, R sowie barbatusin aus Plectranthus caninus Roth und coleon O aus Coleus somaliensis S. Moore. Helv. Chim. Acta. 1975;58:343–356. doi: 10.1002/hlca.19750580203. DOI

Grob K., Rüedi P., Eugster C.H. Drüsenfarbstoffe aus Labiaten: Strukturen von 16 Diterpenen (Coleone und Royleanone) aus Coleus coerulescens GÜRKE. Helv. Chim. Acta. 1978;61:871–884. doi: 10.1002/hlca.19780610235. DOI

Künzle J.M., Rüedi P., Eugster C.H. Isolierung und Strukturaufklärung von 36 Diterpenoiden aus Trichomen von Plectranthus edulis (VATKE) T.T. AYE. Helv. Chim. Acta. 1987;70:1911–1929. doi: 10.1002/hlca.19870700726. DOI

Eugster C.H. Terpenoide, insbesondere diterpenoide Farbstoffe. Ber. Deutsch. Bot. Ges. 1975;88:141–161.

Matloubi-Moghadam F., Rüedi P., Eugster C.H. Drüsefarbstoffe aus Labiaten: Identifizierung von 17 abietanoiden aus Plectranthus sanguineus BRITTEN. Helv. Chim. Acta. 1987;70:975–983. doi: 10.1002/hlca.19870700407. DOI

Alder A.C., Rüedi P., Prewo R., Bieri J.H., Eugster C.H. Neue Diterpenoide aus Blattdrüsen einer Plectranthus sp. aus Rwanda. Helv. Chim. Acta. 1986;69:1395–1417. doi: 10.1002/hlca.19860690613. DOI

Kelecom A., Dos Santos T.C., Medeiros W.L.B. Secoabietane diterpenes from Coleus barbatus. Phytochemistry. 1987;26:2337–2340. doi: 10.1016/S0031-9422(00)84714-7. DOI

Edwards O.E., Feniak G., Los M. Diterpenoid quinones of Inula royleana DC. Can. J. Chem. 1962;40:1540–1546. doi: 10.1139/v62-232. DOI

Brieskorn C.H., Buchberger L. Diterpenchinone aus Labiatenwurzeln1. Planta Med. 1973;24:190–195. doi: 10.1055/s-0028-1099487. PubMed DOI

Hensch M., Rüedi P., Eugster C.H. Horminon, Taxochinon und weitere Royleanone aus 2 abessinischen Plectranthus-Spezies (Labiatae) Helv. Chim. Acta. 1975;58:1921–1934. doi: 10.1002/hlca.19750580707. DOI

Rüedi P. 8α, 9α-Epoxy-7-oxoroyleanon, ein Diterpen-Epoxychinon aus einer abessinischen Plectranthus-Art (Labiatae) Helv. Chim. Acta. 1984;67:1116–1120. doi: 10.1002/hlca.19840670425. DOI

Yoshizaki F., Rüedi P., Eugster C.H. Diterpenoide Drüsenfarbstoffe aus Labiaten: 11 Coleone und Royleanone aus Coleus carnosus HASSK. Helv. Chim. Acta. 1979;62:2754–2762. doi: 10.1002/hlca.19790620826. DOI

Syamasundar K.V., Vinodh G., Srinivas K.V.N.S., Srinivasulu B. A New Abietane Diterpenoid from Plectranthus bishopianus Benth. Helv. Chim. Acta. 2012;95:643–646. doi: 10.1002/hlca.201100425. DOI

Vinodh G., Naveen P., Venkatesan C.S., Rajitha G., Shree A.J. Pharmacological Evaluation of Abietane Diterpenoids from Plectranthus bishopianus as Potent Antibacterial, Antioxidant and Their Cytotoxic Agents. Nat. Prod. J. 2019;9:229–237. doi: 10.2174/2210315508666181120105219. DOI

Kubínová R., Švajdlenka E., Schneiderová K., Hanáková Z., Dall’Acqua S., Farsa O. Polyphenols and diterpenoids from Plectranthus forsteri ‘Marginatus’. Biochem. Syst. Ecol. 2013;49:39–42. doi: 10.1016/j.bse.2013.03.029. DOI

Teixeira A.P., Batista O., Simões M.F., Nascimento J., Duarte A., de la Torrre M.C., Rodríguez B. Abietane diterpenoids from Plectranthus grandidentatus. Phytochemistry. 1997;44:325–327. doi: 10.1016/S0031-9422(96)00467-0. DOI

Gaspar-Marques C., Rijo P., Simões M.F., Duarte M.A., Rodriguez B. Abietanes from Plectranthus grandidentatus and P. hereroensis against methicillin-and vancomycin-resistant bacteria. Phytomedicine. 2006;13:267–271. doi: 10.1016/j.phymed.2005.06.002. PubMed DOI

Abdissa N., Frese M., Sewald N. Antimicrobial Abietane-Type Diterpenoids from Plectranthus punctatus. Molecules. 2017;22:1919. doi: 10.3390/molecules22111919. PubMed DOI PMC

Sitarek P., Toma M., Ntungwe E., Kowalczyk T., Skała E., Wieczfinska J., Śliwiński T., Rijo P. Insight the Biological Activities of Selected Abietane Diterpenes Isolated from Plectranthus spp. Biomolecules. 2020;10:194. doi: 10.3390/biom10020194. PubMed DOI PMC

Śliwiński T., Sitarek P., Skała E., Isca V.M.S., Synowiec E., Kowalczyk T., Bijak M., Rijo P. Diterpenoids from Plectranthus spp. as Potential Chemotherapeutic Agents via Apoptosis. Pharmaceuticals. 2020;13:123. doi: 10.3390/ph13060123. PubMed DOI PMC

Batista O., Duarte A., Nascimento J., Simões M.F., de la Torre M.C., Rodríguez B. Structure and antimicrobial activity of diterpenes from the roots of Plectranthus hereroensis. J. Nat. Prod. 1994;57:858–861. doi: 10.1021/np50108a031. PubMed DOI

Batista O., Simões M.F., Nascimento J., Riberio S., Duarte A., Rodríguez B., de la Torre M.C. A rearranged abietane diterpenoid from Plectranthus hereroensis. Phytochemistry. 1996;41:571–573. doi: 10.1016/0031-9422(95)00646-X. PubMed DOI

Ndjoubi K.O., Sharma R., Badmus J.A., Jacobs A., Jordaan A., Marnewick J., Warner D.F., Hussein A.A. Antimycobacterial, Cytotoxic, and Antioxidant Activities of Abietane Diterpenoids Isolated from Plectranthus madagascariensis. Plants. 2021;10:175. doi: 10.3390/plants10010175. PubMed DOI PMC

Alder A.C., Rüedi P., Eugster C.H. Drüsenfarbstoffe aus Labiaten: Die polaren Diterpenoide aus Plectranthus argentatus ST BLAKE. Helv. Chim. Acta. 1984;67:1523–1530. doi: 10.1002/hlca.19840670616. DOI

Gaspar-Marques C., Pedro M., Simões M.F.A., Nascimento M.S.J., Pinto M.M.M., Rodríguez B. Effect of Abietane Diterpenes from Plectranthus grandidentatus on the Growth of Human Cancer Cell Lines. Planta Med. 2002;68:839–840. doi: 10.1055/s-2002-34407. PubMed DOI

Cerqueira F., Cordeiro-Da-Silva A., Gaspar-Marques C., Simoes F., Pinto M.M.M., Nascimento M.S.J. Effect of abietane diterpenes from Plectranthus grandidentatus on T-and B-lymphocyte proliferation. Bioorg. Med. Chem. 2004;12:217–223. doi: 10.1016/j.bmc.2003.10.006. PubMed DOI

Miyase T., Rüedi P., Eugster C.H. Diterpenoide Drüsenfarbstoffe aus Labiaten: Coleone U, V, W und 14-O-Formyl-coleon-V sowie 2 Royleanone aus Plectranthus myrianthus BRIQ.; cis-und trans-A/B-6, 7-Dioxoroyleanon. Helv. Chim. Acta. 1977;60:2770–2779. doi: 10.1002/hlca.19770600830. DOI

Gaspar-Marques C., Simões M.F., Rodríguez B. A trihomoabietane Diterpenoid from Plectranthus grandidentatus and an Unusual Addition of Acetone to the ortho-Quinone System of Cryptotanshinone. J. Nat. Prod. 2005;68:1408–1411. doi: 10.1021/np0580457. PubMed DOI

Mehrotra R., Vishwakarma R.A., Thakur R.S. Abietane diterpenoids from Coleus zeylanicus. Phytochemistry. 1989;28:3135–3137. doi: 10.1016/0031-9422(89)80293-6. DOI

Matias D., Nicolai M., Saraiva L., Pinheiro R., Faustino C., Diaz Lanza A., Pinto Reis C., Stankovic T., Dinic J., Pesic M., et al. Cytotoxic Activity of Royleanone Diterpenes from Plectranthus madagascariensis Benth. ACS Omega. 2019;4:8094–8103. doi: 10.1021/acsomega.9b00512. PubMed DOI PMC

Kubínova R., Pořízková R., Navrátilová A., Farsa O., Hanáková Z., Bačinská A., Čížek A., Valentová M. Antimicrobial and enzyme inhibitory activities of the constituents of Plectranthus madagascariensis (Pers.) Benth. J. Enzym. Inhib. Med. Chem. 2014;29:749–752. doi: 10.3109/14756366.2013.848204. PubMed DOI

Mei S.X., Jiang B., Niu X.M., Li M.L., Yang H., Na Z., Lin Z.W., Li C.M., Sun H.D. Abietane Diterpenoids from Coleus xanthanthus. J. Nat. Prod. 2002;65:633–637. doi: 10.1021/np0102049. PubMed DOI

Wellsow J., Grayer R.J., Veitch N.C., Kokubun T., Lelli R., Kite G.C., Simmonds M.S.J. Insect-antifeedant and antibacterial activity of diterpenoids from species of Plectranthus. Phytochemistry. 2006;67:1818–1825. doi: 10.1016/j.phytochem.2006.02.018. PubMed DOI

Batista O., Simões M.F., Duarte A., Valdeira M.L., de la Torre M.C., Rodríguez B. An antimicrobial abietane from the root of Plectranthus hereroensis. Phytochemistry. 1995;38:167–169. doi: 10.1016/0031-9422(94)00586-I. PubMed DOI

Nzogong R.T., Nganou B.K., Tedonkeu A.T., Awouafack M.D., Tene M., Ito T., Tane P., Morita H. Three New Abietane-Type Diterpenoids from Plectranthus africanus and Their Antibacterial Activities. Planta Med. 2018;84:59–64. doi: 10.1055/s-0043-114426. PubMed DOI

Jurkaninová S., Kubínová R., Nejezchlebová M., Gazdová M., Hanáková Z., Dall’Acqua S. Anti-MRSA activity of abietane diterpenes from Coleus blumei Benth. Nat. Prod. Res. 2021;35:3033–3039. doi: 10.1080/14786419.2019.1686371. PubMed DOI

Matloubi-Moghadam F., Rüedi P., Eugster C.H. Neue Coleone und Royleanone aus Coleus somaliensis S. MOORE. Helv. Chim. Acta. 1984;67:201–208. doi: 10.1002/hlca.19840670125. DOI

Rüedi P. Neue Diterpene aus Blattdrüsen von Plectranthus barbatus (Labiatae). Die absolute Konfiguration der 2-Hydroxypropyl-Seitenkette in Coleon, E. Helv. Chim. Acta. 1986;69:972–984. doi: 10.1002/hlca.19860690504. DOI

Zhu Z.Y., Nayeshiro H., Prewo R., Rüedi P., Eugster C.H. Fredericone, neue hochfunktionalisierte Abietanoide aus Blattdrüsen von Coleus fredericii G. TAYL. Helv. Chim. Acta. 1988;71:577–587. doi: 10.1002/hlca.19880710310. DOI

Baxter R.L., Blake A.J., Gould R.O. The absolute configuration of coleon A: A seco-diterpenoid pigment from Coleus spp. Phytochemistry. 1995;38:195–197. doi: 10.1016/0031-9422(94)00588-K. DOI

Eugster C.H., Küng H.P., Kühnis H., Karrer P. Isolierung und Charakterisierung zweier neuer Blattfarbstoffe: Coleon A und Coleon, B. Chinontrennungen an Polyamidpulver. Helv. Chim. Acta. 1963;46:530–543. doi: 10.1002/hlca.19630460214. DOI

Karanatsios D., Eugster C.H. Struktur von Coleon A. Helv. Chim. Acta. 1965;48:471–508. doi: 10.1002/hlca.19650480307. DOI

Musayeib N.M.A., Amina M., Al-Hamoud G.A., Mohamed G.A., Ibrahim S.R., Shabana S. Plectrabarbene, a New Abietane Diterpene from Plectranthus barbatus Aerial Parts. Molecules. 2020;25:2365. doi: 10.3390/molecules25102365. PubMed DOI PMC

Rüedi P., Eugster C.H. Struktur von Coleon E, einem neuen diterpenoiden Methylenchinon aus der Coleus barbatus-Gruppe (Labiatae) Helv. Chim. Acta. 1972;55:1994–2014. doi: 10.1002/hlca.19720550619. DOI

Wang A.H., 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. doi: 10.1021/ja00809a043. PubMed DOI

Moir M., Rüedi P., Eugster C.H. Diterpenoids from Coleus somaliensis (S. Moore): Coleons, G., and J. Helv. Chim. Acta. 1973;56:2539–2548. doi: 10.1002/hlca.19730560738. DOI

Rüedi P., Schmid J.M., Prewo R., Bieri J.H., Eugster C.H. Spirocoleone: Synthese und Charakterisierung von vier diastereomeren Spiro(methylcyclopropan)-Substrukturen; Revision der Konfiguration an C (12) und C (15) von Coleon P und Derivaten sowie von Coleon-Z-Derivaten; Röntgenstrukturanalysen von Lanugon J und weiteren Spirocoleonen. Helv. Chim. Acta. 1983;66:429–449.

Lekphrom R., Kanokmedhakul S., Kanokmedhakul K. Bioactive Diterpenes from the Aerial Parts of Anisochilus harmandii. Planta Med. 2010;76:726–728. doi: 10.1055/s-0029-1240656. PubMed DOI

Miyase T., Yoshizaki F., Kabengele N.T., Rüedi P., Eugster C.H. Strukturen von 13 Diterpenen (Coleonen) aus Blattdrüsen von Solenostemon sylvaticus und Coleus garckeanus (Labiatae) Helv. Chim. Acta. 1979;62:2374–2383. doi: 10.1002/hlca.19790620734. DOI

Ávila F.N., Pinto F.C., Sousa T.S., Torres M.C.M., Costa-Lotufo L.V., Rocha D.D., de Vasconcelos M.A., Cardoso-Sá N., Teixeira E.H., Albuquerque M.R.J.R., et al. Miscellaneous Diterpenes from the Aerial Parts of Plectranthus ornatus Codd. J. Braz. Chem. Soc. 2017;28:1014–1022. doi: 10.21577/0103-5053.20160255. DOI

Simões M.F., Rijo P., Duarte A., Barbosa D., Matias D., Delgado J., Cirilo N., Rodríguez B. Two new diterpenoids from Plectranthus species. Phytochem. Lett. 2010;3:221–225. doi: 10.1016/j.phytol.2010.08.002. DOI

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. doi: 10.1016/0040-4020(77)88005-8. DOI

de Araújo Rodrigues P., de Morais S.M., de Souza C.M., Araújo Silva A.R., de Andrade G.M., Vasconcelos Silva M.G., Albuquerque R.L., Rao V.S., Santos F.A. Gastroprotective effect of barbatusin and 3-beta-hydroxy-3-deoxibarbatusin, quinonoid diterpenes isolated from Plectranthus grandis, in ethanol-induced gastric lesions in mice. J. Ethnopharmacol. 2010;127:725–730. doi: 10.1016/j.jep.2009.11.031. PubMed DOI

Mesquita L.S.F., Matos T.S., do Nascimento Ávila F., da Silva Batista A., Moura A.F., de Moraes M.O., da Silva M.C.M., Ferreira T.L.A., Nascimento N.R.F., Monteiro N.K.V., et al. Diterpenoids from Leaves of Cultivated Plectranthus ornatus. Planta Med. 2021;87:124–135. doi: 10.1055/a-1209-3252. PubMed DOI

Albuquerque R.L.D., Kentopff M.R., Machado M.I.L., Silva M.G.V., Matos F.J.D.A., Morais S.M., Braz-Filho R. Diterpenos tipo abietano isolados de Plectranthus barbatus Andrews. Quím. Nova. 2007;30:1882–1886. doi: 10.1590/S0100-40422007000800016. DOI

Kubo I., Matsumoto T., Tori M., Asakawa Y. Structure of plectrin, an aphid antifeedant diterpene from Plectranthus barbatus. Chem. Lett. 1984;13:1513–1516. doi: 10.1246/cl.1984.1513. DOI

Devriese E.G., Buffel K., Geuns J.M. Stimulation of adventitious root formation on mung bean cuttings by coleon O. Phytochemistry. 1988;27:293–294. doi: 10.1016/0031-9422(88)80639-3. DOI

Miyase T., Rüedi P., Eugster C.H. Unusual Rearranged Abietanoic Diterpenoids from Solenostemon Species. J. Chem. Soc. Chem. Commun. 1977:859–860. doi: 10.1039/C39770000859. DOI

Kubínová R., Gazdová M., Hanáková Z., Jurkaninová S., Dall’Acqua S., Cvačka J., Humpa O. New diterpenoid glucoside and flavonoids from Plectranthus scutellarioides (L.) R. Br. S. Afr. J. Bot. 2019;120:286–290. doi: 10.1016/j.sajb.2018.08.023. DOI

Ito T., Rakainsa S.K., Nisa K., Morita H. Three new abietane-type diterpenoids from the leaves of Indonesian Plectranthus scutellarioides. Fitoterapia. 2018;127:146–150. doi: 10.1016/j.fitote.2018.02.013. PubMed DOI

Miyase T., Rüedi P., Eugster C.H. Struktur von sechs Coleonen (Diterpenen) aus Solenostemon monostachys (P. BEAUV.) BRIQ. (Labiatae) Helv. Chim. Acta. 1980;63:95–101. doi: 10.1002/hlca.19800630110. DOI

Zhou Q. Natural diterpene and triterpene quinone methides: Structures, synthesis and biological potentials. In: Rokita S.E., editor. Quinone Methides. John Wiley & Sons; Hoboken, NJ, USA: 2009. pp. 269–295.

Dellar J.E., Cole M.D., Waterman P.G. Antimicrobial abietane diterpenoids from Plectranthus elegans. Phytochemistry. 1996;41:735–738. doi: 10.1016/0031-9422(95)00694-X. PubMed DOI

Mothana R.A., Al-Said M.S., Al-Musayeib N.M., Gamal A.A.E., Al-Massarani S.M., Al-Rehaily A.J., Abdulkader M., Maes L. In Vitro Antiprotozoal Activity of Abietane Diterpenoids Isolated from Plectranthus barbatus Andr. Int. J. Mol. Sci. 2014;15:8360–8371. doi: 10.3390/ijms15058360. PubMed DOI PMC

Rüedi P., Eugster C.H. Diterpenoide Drüsenfarbstoffe aus Labiaten: 6 neue p-Chinomethane aus Plectranthus parviflorus WILLD. Helv. Chim. Acta. 1978;61:709–715. doi: 10.1002/hlca.19780610219. DOI

Alder A.C., Rüedi P., Eugster C.H. Drüsenfarbstoffe aus tropischen Labiaten: Parviflorone aus Plectranthus strigosus BENTH. Helv. Chim. Acta. 1984;67:1531–1534. doi: 10.1002/hlca.19840670617. DOI

Narukawa Y., Shimizu N., Shimotohno K., Takeda T. Two new diterpenoids from Plectranthus nummularius Briq. Chem. Pharm. Bull. 2001;49:1182–1184. doi: 10.1248/cpb.49.1182. PubMed DOI

Nyila M.A., Leonard C.M., Hussein A.A., Lall N. Bioactivities of Plectranthus ecklonii Constituents. Nat. Prod. Commun. 2009;4:1934578X0900400903. doi: 10.1177/1934578X0900400903. PubMed DOI

Burmistrova O., Perdomo J., Simões M.F., Rijo P., Quintana J., Estevez F. The abietane diterpenoid parvifloron D from Plectranthus ecklonii is a potent apoptotic inducer in human leukemia cells. Phytomedicine. 2015;22:1009–1016. doi: 10.1016/j.phymed.2015.06.013. PubMed DOI

Gaspar-Marques C., Fátima Simões M., Luísa Valdeira M., Rodriguez B. Terpenoids and phenolics from Plectranthus strigosus, bioactivity screening. Nat. Product Res. 2008;22:167–177. doi: 10.1080/14786410701654560. PubMed DOI

Fuson R.C. The principle of Vinylogy. Chem. Rev. 1935;16:1–27. doi: 10.1021/cr60053a001. DOI

Uchida M., Miyase T., Yoshizaki F., Bieri J.H., Rüedi P., Eugster C.H. 14-Hydroxytaxodion als Hauptditerpen in Plectranthus grandidentatus GÜRKE.; Isolierung von sieben neuen dimeren Diterpenen aus P. grandidentatus, P. myrianthus BRIQ. und Coleus carnosus HASSK.: Strukturen der Grandidone A, 7-Epi-A, B, 7-Epi-B, C, D und 7-Epi-D. Helv. Chim. Acta. 1981;64:2227–2250.

Falé P.L., Borges C., Madeira P.J.A., Ascensão L., Araújo M.E.M., Florêncio M.H., Serralheiro M.L.M. Rosmarinic acid, scutellarein 4′-methyl ether 7-O-glucuronide and (16S)-coleon E are the main compounds responsible for the antiacetylcholinesterase and antioxidant activity in herbal tea of Plectranthus barbatus (“falso boldo”) Food Chem. 2009;114:798–805. doi: 10.1016/j.foodchem.2008.10.015. DOI

Rüedi P., Eugster C.H. Struktur von Coleon, F. Helv. Chim. Acta. 1973;56:1129–1132. doi: 10.1002/hlca.19730560336. DOI

Alder A.C., Rüedi P., Eugster C.H. Plectranthone, C und, D. Diterpenoide Phenanthren-1,4-dione aus Blattdrüsen einer Plectranthus sp. (Labiatae) Helv. Chim. Acta. 1984;67:1003–1011. doi: 10.1002/hlca.19840670412. DOI

Schultz C., Bossolani M.P., Torres L.M., 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. doi: 10.1016/j.jep.2006.09.046. PubMed DOI

Ribi M., Sin-Ren A.C., Küng H.P., Eugster C.H. Struktur und Reaktionen von Coleon B. 2. Mitteilung über Coleon B. Helv. Chim. Acta. 1969;52:1685–1728. doi: 10.1002/hlca.19690520626. DOI

Arihara S., Rüedi P., Eugster C.H. Diterpenoide Drüsenfarbstoffe: Coleone S und T aus Plectranthus caninus Roth (Labiatae), ein neues Diosphenol/trans-A/B-6,7-Diketon-Paar aus der Abietanreihe. Helv. Chim. Acta. 1977;60:1443–1447. doi: 10.1002/hlca.19770600436. DOI

Rijo P., Gaspar-Marques C., Simões M.F., Jimeno M.L., Rodríguez B. Further diterpenoids from Plectranthus ornatus and P. grandidentatus. Biochem. Syst. Ecol. 2007;35:215–221. doi: 10.1016/j.bse.2006.10.011. DOI

Rüedi P., Eugster C.H. Coleone C, D, I, I′ aus einer madegassischen Plectranthus sp. nov. Interkonversion von cis-und trans-A/B-6, 7-Diketoditerpenen. Helv. Chim. Acta. 1975;58:1899–1912. doi: 10.1002/hlca.19750580705. DOI

Rüedi P., Eugster C.H. Struktur von Coleon C, einem neuen Blattfarbstoff aus Coleus aquaticus Gürcke. Helv. Chim. Acta. 1971;54:1606–1621. doi: 10.1002/hlca.19710540612. DOI

Moir M., Rüedi P., Eugster C.H. Diterpenoid Hydroquinones from Coleus somaliensis (S. Moore): Coleons H., I., and K. Helv. Chim. Acta. 1973;56:2534–2539. doi: 10.1002/hlca.19730560737. DOI

Rüedi P., Eugster C.H. Diterpenoide Drüsenfarbstoffe: Coleon L, ein neues Diosphenol aus Coleus somaliensis S. MOORE; Revision der Strukturen von Coleon H., I., I′ und K. Helv. Chim. Acta. 1977;60:1233–1238. doi: 10.1002/hlca.19770600412. DOI

Ragasa C.Y., Templora V.F., Rideout J.A. Diastereomeric Diterpenes from Coleus blumei. Chem. Pharm. Bull. 2001;49:927–929. doi: 10.1248/cpb.49.927. PubMed DOI

Rüedi P., Eugster C.H. Coleon D, ein Diterpen aus Coleus aquaticus Guercke mit trans-A/B-6, 7-Dioxostruktur. Helv. Chim. Acta. 1972;55:1736–1745. doi: 10.1002/hlca.19720550532. DOI

Buchbauer G., Rüedi P., Eugster C.H. Edulon A, ein 2H-1-Oxapyrenderivat aus Plectranthus edulis (Labiatae) Helv. Chim. Acta. 1978;61:1969–1974. doi: 10.1002/hlca.19780610604. DOI

Künzle J.M., Rüedi P., Prewo R., Eugster C.H. Struktur von Edulon A. Helv. Chim. Acta. 1986;69:1513–1520. doi: 10.1002/hlca.19860690623. DOI

Kelecom A., Dos Santos T.C. Cariocal, a new seco-abietane diterpene from the Labiate Coleus barbatus. Tetrahedron Lett. 1985;26:3659–3662. doi: 10.1016/S0040-4039(00)89216-3. DOI

Mothana R.A., Khaled J.M., El-Gamal A.A., Noman O.M., Kumar A., Alajmi M.F., Al-Rehaily A.J., Al-Said M.S. Comparative evaluation of cytotoxic, antimicrobial and antioxidant activities of the crude extracts of three Plectranthus species grown in Saudi Arabia. Saudi Pharm. J. 2019;27:162–170. doi: 10.1016/j.jsps.2018.09.010. PubMed DOI PMC

Kelecom A. An abietane diterpene from the Labiate Coleus barbatus. Phytochemistry. 1984;23:1677–1679. doi: 10.1016/S0031-9422(00)83467-6. DOI

Amina M., Al-Musayeib N.M., Alam P., Aleanizy F.S., Alqahtni F.Y., Al-Said M.S., Al-Rashidi N.S., Shakeel F. Cytotoxic evaluation and concurrent analysis of two diterpenes in the chloroform extract of Plectranthus barbatus using a validated HPTLC-UV method. Bull. Chem. Soc. Ethiop. 2018;32:407–419. doi: 10.4314/bcse.v32i3.1. DOI

Horvath T., Linden A., Yoshizaki F., Eugster C.H., Rüedi P. Abietanes and a Novel 20-Norabietanoid from Plectranthus cyaneus (Lamiaceae) Helv. Chim. Acta. 2004;87:2346–2353. doi: 10.1002/hlca.200490210. DOI

Garcia C., Teodósio C., Oliveira C., Oliveira C., Díaz-Lanza A., Reis C., Duarte N., Rijo P. Naturally occurring Plectranthus-derived diterpenes with antitumoral activities. Curr. Pharm. Des. 2018;24:4207–4236. doi: 10.2174/1381612825666190115144241. PubMed DOI

Slameňová D., Mašterová I., Lábaj J., Horváthová E., Kubala P., Jakubíková J., Wsólová L. Cytotoxic and DNA-damaging effects of diterpenoid quinones from the roots of Salvia officinalis L. on colonic and hepatic human cells cultured in vitro. Basic Clin. Pharmacol. Toxicol. 2004;94:282–290. doi: 10.1111/j.1742-7843.2004.pto940605.x. PubMed DOI

Fronza M., Murillo R., Ślusarczyk S., Adams M., Hamburger M., Heinzmann B., Laufer S., Merfort I. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica. Bioorg. Med. Chem. 2011;19:4876–4881. doi: 10.1016/j.bmc.2011.06.067. PubMed DOI

Garcia C., Silva C.O., Monteiro C.M., Nicolai M., Viana A., Andrade J.M., Barasoain I., Stankovic T., Quintana J., Hernandéz I., et al. Anticancer properties of the abietane diterpene 6, 7-dehydroroyleanone obtained by optimized extraction. Future Med. Chem. 2018;10:1177–1189. doi: 10.4155/fmc-2017-0239. PubMed DOI

Xing X., Wu H., Wang X., Huang Y., Li Q., Li C., Yang Y., Liu Y., Liu J. Inhibition of tumor cell proliferation by coleon C. J. Chemother. 2008;20:238–245. doi: 10.1179/joc.2008.20.2.238. PubMed DOI

Alegre-Gómez S., Sainz P., Simões M.F., Rijo P., Moiteiro C., González-Coloma A., Martínez-Díaz R.A. Antiparasitic activity of diterpenoids against Trypanosoma cruzi. Planta Med. 2017;83:306–311. doi: 10.1055/s-0042-115646. PubMed DOI

Zadali R., Ebrahimi S.N., Tofighi Z., Es-Haghi A., Hamburger M., Kaiser M., D’ Ambola M., De Tommasi N., Hadjiakhoondi A. Antiprotozoal activity of diterpenoids isolated from Zhumeria majdae- absolute configuration by circular dichroism. DARU J. Pharm. Sci. 2020;28:455–462. doi: 10.1007/s40199-020-00345-w. PubMed DOI PMC

Areche C., Schmeda-Hirschmann G., Theoduloz C., Rodríguez J.A. Gastroprotective effect and cytotoxicity of abietane diterpenes from the Chilean Lamiaceae Sphacele chamaedryoides (Balbis) Briq. J. Pharm. Pharmacol. 2009;61:1689–1697. doi: 10.1211/jpp/61.12.0015. PubMed DOI

Murakami S., Muramatsu M., Tomisawa K. Inhibition of gastric H+, K+-ATPase by flavonoids: A structure-activity study. J. Enzyme Inhib. 1999;14:151–166. doi: 10.3109/14756369909036551. PubMed DOI

Najít záznam

Citační ukazatele

Nahrávání dat ...

Možnosti archivace

Nahrávání dat ...