An easy and stereoselective rearrangement of an abietane diterpenoid into a bioactive microstegiol derivative

Phytochemistry Letters

Volumn 3, Issue 4, 2010, Pages 234-237

  Simões, María Fátima ^a   Rijo, Patricia ^a   Duarte, Aida ^a   Matias, Diogo ^a   Rodríguez, Benjamín ^b  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Abietanes; Acid washed molecular sieves as catalyst; Labiatae; Microstegiol derivative; Plectranthus ecklonii; Rearranged abietanes

Indexed keywords

2BETA (4 HYDROXY)BENZOYLOXY 11BETA HYDROXY 4(5-11),20(10-5)DIABEO 5(10),6,8,13 ABIETATETRAEN 12 ONE; ABIETANE DERIVATIVE; DITERPENOID; MICROSTEGIOL; OLEANOLIC ACID; PARVIFLORON D; SITOSTEROL; STIGMASTEROL; SUGIOL; UNCLASSIFIED DRUG; URSOLIC ACID;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; ENTEROCOCCUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS; STEREOCHEMISTRY;

ENTEROCOCCUS; LAMIACEAE; PLECTRANTHUS; STAPHYLOCOCCUS;

EID: 78649517992     PISSN: 18743900     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytol.2010.09.001     Document Type: Article

References (25)

1. M. Abdel-Mogib, H.A. Albar, and S.M. Batterjee Chemistry of the genus Plectranthus Molecules 7 2002 271 301
2. A.U. Acuña, F. Amat-Guerri, P. Morcillo, M. Liras, and B. Rodriguez Structure and formation of the fluorescent compound of Lignum nephriticum Org. Lett. 11 2009 3020 3023
3. C.-F. Chyu, H.-C. Lin, and Y.-H. Kuo New abietane and seco-abietane diterpenes from the roots of Taiwania cryptomerioides Chem. Pharm. Bull. 53 2005 11 14
4. C. Gaspar-Marques, P. Rijo, M.F. Simões, M.A. Duarte, and B. Rodríguez Abietanes from Plectranthus grandidentatus and P. hereroensis against methicillin- and vancomycin-resistant bacteria Phytomedicine 13 2006 267 271
5. C. Gaspar-Marques, M.F. Simões, M.L. Valdeira, and B. Rodríguez Terpenoids and phenolics from Plectranthus strigosus, bioactivity screening Nat. Prod. Res. 22 2008 167 177
6. A. Kabouche, N. Boutaghane, Z. Kabouche, E. Seguin, F. Tillequin, and K. Benlabed Components and antibacterial activity of the roots of Salvia jaminiana Fitoterapia 76 2005 450 452
7. D. Karanatsios, J.S. Scarpa, and C.H. Eugster Struktur von Fuerstion Helv. Chim. Acta 49 1966 1151 1172
8. G. Kökdil, G. Topcu, A. Gören, and W. Voelter Steroids and terpenoids from Ajuga relicta Z. Naturforsch. 57b 2002 957 960
9. S.M. Kupchan, A. Karim, and C. Marcks Tumor inhibitors. XLVIII. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum J. Org. Chem. 34 1969 3912 3918
10. M. Li, J.-S. Zhang, Y.-M. Ye, and J.-N. Fang Constituents of the roots of Salvia prionitis J. Nat. Prod. 63 2000 139 141
11. T. Matsumoto, Y. Takeda, K. Soh, M. Sakamoto, and S. Imai Skeletal rearrangement of the dehydroabietic acid derivatives Bull. Chem. Soc. Jpn. 68 1995 2349 2353
12. Y. Narukawa, N. Shimizu, K. Shimotohno, and T. Takeda Two new diterpenoids from Plectranthus nummularius Briq Chem. Pharm. Bull. 49 2001 1182 1184
13. M.A. Nyila, C.M. Leonard, A.A. Hussein, and N. Lall Bioactivities of Plectranthus ecklonii constituents Nat. Prod. Commun. 4 2009 1177 1180
14. M. Politi, A. Braca, N. Tommasi, I. Morelli, A. Manunta, L. Battinelli, and G. Mazzanti Antimicrobial diterpenes from the seeds of Cephalotaxus harringtonia var. drupacea Planta Med. 69 2003 468 470
15. 13C NMR spectral assignments of some natural abietane diterpenoids Magn. Reson. Chem. 41 2003 741 746
16. P. Rüedi, and C.H. Eugster Leaf-gland pigments: 6 novel p-quinomethanes of the abietane series from Plectranthus parviflorus Willd Helv. Chim. Acta 61 1978 709 715
17. M.J. Sexmero-Cuadrado, M.C. de la Torre, L.-Z. Lin, G.A. Cordell, B. Rodríguez, and A. Perales Cyclization reactions of the o-naphthoquinone diterpene aethiopinone. A revision of the structure of prionitin J. Org. Chem. 57 1992 4722 4728
18. F. Simões, A. Michavila, B. Rodríguez, M.C. García-Álvarez, and M. Hasan A quinone methide diterpenoid from the root of Salvia moorcraftiana Phytochemistry 25 1986 755 756
19. R.A. Taj, A. Abhayawardhana, and J.R. Green Cyclohepta[de]naphthalenes and the rearranged abietane framework of microstegiol via Nicholas reaction chemistry Synlett 2009 292 296
20. G. Topcu, and A. Ulubelen Abietane and rearranged abietane diterpenes from Salvia montbretii J. Nat. Prod. 59 1996 734 737 (Pubitemid 26299157)
21. G. Topcu, E.N. Altiner, S. Gozcu, B. Halfon, Z. Aydogmus, J.M. Pezzuto, B.-N. Zhou, and D.G.I. Kingston Studies on di- and triterpenoids from Salvia staminea with cytotoxic activity Planta Med. 69 2003 464 467
22. A. Ulubelen, G. Topcu, N. Tan, L.-J. Lin, and G.A. Cordell Microstegiol, a rearranged diterpene from Salvia microstegia Phytochemistry 31 1992 2419 2421
23. A. Ulubelen, U. Sönmez, and G. Topcu Diterpenoids from the root of Salvia sclarea Phytochemistry 44 1997 1297 1299
24. A. Ulubelen, S. Öksüz, U. Kolak, C. Bozok-Johansson, C. elik, and W. Voelter Antibacterial diterpenes from the roots of Salvia viridis Planta Med. 66 2000 458 462
25. R.L. Van Zyl, F. Khan, T.J. Edwards, and S.E. Drewes Antiplasmodial activities of some abietane diterpenes from the leaves of five Plectranthus species S. Afr. J. Sci. 104 2008 62 64