Further Labdane and Kaurane Diterpenoids and Other Constituents from Plectranthus fruticosus

Journal of Natural Products

Volumn 67, Issue 4, 2004, Pages 614-621

  Gaspar Marques, Cristina ^a   Simões, M Fátima ^a   Rodríguez, Benjamín ^b  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

10(14)AROMADENDRENE 4BETA,15 DIOL; ACETONE; DITERPENOID; ENT 12BETA ACETOXY 15BETA HYDROXYKAUR 16 EN 19 OIC ACID; ENT 12BETA ACETOXY 17 OXOKAUR 15 EN 19 OIC ACID; ENT 12BETA ACETOXY 7BETA HYDROXYKAUR 16 EN 19 OIC ACID; ENT 3BETA ACETOXYLABDA 8(17),12,14 TRIEN 2ALPHA OL; ENT 7BETA HYDROXY 15BETA,16BETA EPOXYKAURAN 19 OIC ACID; ENT 7BETA HYDROXYKAUR 15 EN 19 OIC ACID; ENT LABDA 8(17),12,14 TRIENE 2ALPHA,3BETA DIBENZOATE; ENT LABDA 8(17),12,14 TRIENE 2ALPHA,3BETA DIOL; ESTER DERIVATIVE; HERBACEOUS AGENT; KANAMYCIN; KAURANE DERIVATIVE; LABDANE DERIVATIVE; METHYL ENT 12BETA ACETOXY 15BETA HYDROXYKAUR 16 EN 19 OATE; METHYL ENT 12BETA ACETOXY 15BETA,16BETA EPOXYKAURAN 19 OATE; METHYL ENT 12BETA ACETOXY 17 OXOKAUR 15 EN 19 OATE; METHYL ENT 12BETA ACETOXY 7BETA HYDROXYKAUR 15 EN 19 OATE; METHYL ENT 12BETA HYDROXYKAUR 16 EN 19 OATE; METHYL GROUP; PLANT EXTRACT; PLECTRANTHUS FRUTICOSUS EXTRACT; SESQUITERPENOID; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG TRANSFORMATION; ESCHERICHIA COLI; HERBAL MEDICINE; INFRARED SPECTROSCOPY; MEDICINAL PLANT; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLECTRANTHUS FRUTICOSUS; PROTON NUCLEAR MAGNETIC RESONANCE; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

ANTI-BACTERIAL AGENTS; CANDIDA ALBICANS; DITERPENES; DITERPENES, KAURANE; ESCHERICHIA COLI; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLECTRANTHUS; PORTUGAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM;

CANDIDA; CANDIDA ALBICANS; ESCHERICHIA COLI; PLECTRANTHUS; POSIBACTERIA; PSEUDOMONAS; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS;

EID: 11144355526     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np030490j     Document Type: Article

References (44)

1. Gaspar-Marques, C.; Simões, M. F.; Duarte, A.; Rodríguez, B. J. Nat. Prod. 2003, 66, 491-496.
2. Sutthivaiyakit, S.; Nareeboon, P.; Ruangrangsi, N.; Ruchirawat, S.; Pisutjaroenpong, S.; Mahidol, C. Phytochemistry 2001, 56, 811-814.
3. Beale, M. H.; Bearder, J. R.; MacMillan, J.; Matsuo, A.; Phinney, B. O. Phytochemistry 1983, 22, 875-881.
4. Lewis, N. J.; MacMillan, J. J. Chem. Soc., Perkin Trans. 1 1980, 1270-1278.
5. Bohlmann, F.; Knoll, K.-H.; Robinson, H.; King, R. M. Phytochemistry 1980, 19, 107-110.
6. Bohlmann, F.; Jakupovic, J.; King, R. M.; Robinson, H. Phytochemistry 1980, 19, 863-868.
7. Biftu, T.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1978, 360-363.
8. Star, A. E.; Mabry, T. J. Phytochemistry 1971, 10, 2817-2818.
9. Sakakibara, M.; DiFeo, D.; Nakatani, N.; Timmermann, B.; Mabry, T. J. Phytochemistry 1976, 15, 727-731.
10. Wollenweber, E.; Wassum, M. Tetrahedron Lett. 1972, 9, 797-800.
11. Rodriguez, B.; Martín-Panizo, F. An. Quím. 1979, 75, 431-432.
12. Rao, M. M.; Kingston, D. G. I.; Spittler, T. D. Phytochemistry 1970, 9, 227-228.
13. Kupchan, S. M.; Sigel, C. W.; Hemingway, R. J.; Knox, J. R.; Udayamurthy, M. S. Tetrahedron 1969, 25, 1603-1615.
14. Timmermann, B. N.; Mues, R.; Mabry, T. J.; Powell, A. M. Phytochemistry 1979, 18, 1855-1858.
15. Seebacher, W.; Simic, N.; Weis, R.; Saf, R.; Kunert, O. Magn. Reson. Chem. 2003, 41, 636-638.
16. Krebs, H. C.; Rakotoarimanga, J. V.; Habermehl, G. G. Magn. Reson. Chem. 1990, 28, 124-128.
17. Juell, S. M.-K.; Hansen, R.; Jork, H. Arch. Pharm. (Weinheim, Ger.) 1976, 309, 458-466.
18. Several numbering systems are in use for aromadendranes; the one chosen for this paper is that most commonly used (Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids; Chapman & Hall: London, 1991; Vol. 1, p XXV), and it is indicated on formula 1.
19. Faure, R.; Ramanoelina, A. R. P.; Rakotonirainy, O.; Bianchini, J.-P.; Gaydou, E. M. Magn. Reson. Chem. 1991, 29, 969-971.
20. Ciminiello, P.; Fattorusso, E.; Magno, S.; Mayol, L. Can. J. Chem. 1987, 65, 518-522.
21. Rashid, M. A.; Gray, A. I.; Waterman, P. G.; Armstrong, J. A. J. Nat. Prod. 1995, 58, 618-621.
22. Wessels, M.; König, G. M.; Wright, A, D. J. Nat. Prod. 2001, 64, 370-372.
23. Goldsby, G.; Burke, B. A. Phytochemistry 1987, 26, 1059-1063.
24. Gijsen, H. J. M.; Wijnberg, J. B. P. A.; de Groot, Ae. In Progress in the Chemistry of Organic Natural Products; Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm, Ch., Eds.; Springer-Verlag: Vienna, 1995; Vol. 64, pp 149-193.
25. Abdel-Mogib, M.; Albar, H. A.; Batterjee, S. M. Molecules 2002, 7, 271-301.
26. Fournier, G.; Paris, M.; Dumitresco, S. M.; Pages, N.; Boudene, C. Planta Med. 1986, 52, 486-488.
27. 26 of the essential oil of P. fruticosus on a fused silica capillary column allowed the identification of 10(14)-aromadendrene, but without defining its absolute configuration.
28. 1H NMR spectra of these compounds also refer to this nomenclature throughout the text.
29. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy. Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983; pp 15-17, 55-103.
30. 248 -6.6) which could be associated with interactions between the benzoates and the 12Z,-14-diene chromophore (see ref 29, pp 255-259).
31. Hutchison, M.; Lewer, P.; MacMillan, J. J. Chem. Soc., Perkin Trans. 1 1984, 2363-2366.
32. Liu, G.; Müller, R.; Rüedi, P. Helv. Chim. Acta 2003, 86, 420-438.
33. Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids; Chapman & Hall: London, 1991; Vol. 2, pp 906-946, 948-956.
34. Katti, S. B.; Rüedi, P.; Eugster, C. H. Helv. Chim. Acta 1982, 65, 2189-2197.
35. Liu, G.; Rüedi, P. Phytochemistry 1996, 41, 1563-1568.
36. Fujita, E.; Ochiai, M.; Ichida, I.; Chatterjee, A.; Desmukh, S. K. Phytochemistry 1975, 14, 2249-2251.
37. 1,25 in plants belonging to this genus.
38. Duc, D. K. M.; Fétizon, M.; Lazare, S.; Grant, P. K.; Nicholls, M. J.; Liau, H. T. L.; Francis, M. J.; Poisson, J.; Bernassau, J.-M.; Roque, N. F.; Wovkulich, P. M.; Wenkert, E. Tetrahedron 1981, 37, 2371-2374.
39. Bohlmann, F.; Suding, H.; Cuatrecasas, J.; Robinson, H.; King, R. M. Phytochemistry 1980, 19, 2399-2403.
40. Herz, W.; Kulanthaivel, P.; Watanabe, K. Phytochemistry 1983, 22, 2021-2025.
41. Harrigan, G. G.; Bolzani, V. S.; Gunatilaka, A. A. L.; Kingston, D. G. I. Phytochemistry 1994, 36, 109-113.
42. Anam, E. M. Indian. J. Chem. 1998, 37B, 187-189.
43. Signals marked with an asterisk appeared as overlapped or partially overlapped multiplets, and their assignments were in agreement with the HSQC spectrum.
44. Anonymous. In National Committee for Clinical Laboratory Standards, 5th ed.; NCCLS: Wayne, PA, 2000; approved standard M7-A5.