Secondary Metabolites of Phlomis viscosa and Their Biological Activities
Further phytochemical studies on the aerial parts of Phlomis viscosa (Lamiaceae) led to the isolation of 24 compounds: 3 iridoid glycosides, 10 phenylethanoid glycosides, a megastigmane glycoside and a hydroquinone glycoside, as well as 2 lignan glucosides and 7 neolignan glucosides, 1 of which is new (17b). Compound 17b was obtained as a minor component of an inseparable mixture (2:1) of 2 neolignan glucosides (17a/b), and characterized as 3',4-O-dimethylcedrusin 9-O-b -glucopyranoside. Full NMR data of the known 8-O-4' neolignan glucoside, erythro-1-(4-O-b-glucopyranosyl-3-methoxyphenyl)- 2-{2-methoxyl-4-[1-(E)-propene-3-ol]-phenoxyl}-propane-1,3-diol (18) are also reported. All isolated compounds were screened for cell growth inhibition versus 3 tumor cell lines (MCF7, NCI-H460, and SF-268) and several phenylethanoid glycosides were found to possess weak antitumoral activity. The phenylethanoid glycosides were also evaluated for their free radical (DPPH) scavenging, antibacterial and antifungal activities. The free radical (DPPH) scavenging activities of verbascoside (4), isoacteoside (5), forsythoside B (10), myricoside (13) and samioside (14) were found to be comparable to that of dl-a -tocopherol. Compounds 4, 5, 10 and 14 (MIC: 500 m g/mL) as well as Leucosceptoside A (8) and 13 (MIC:1000 m g/mL) showed very weak activity against Gram (+) bacteria.
Secondary Metabolites of Phlomis viscosa and Their Biological Activities
Further phytochemical studies on the aerial parts of Phlomis viscosa (Lamiaceae) led to the isolation of 24 compounds: 3 iridoid glycosides, 10 phenylethanoid glycosides, a megastigmane glycoside and a hydroquinone glycoside, as well as 2 lignan glucosides and 7 neolignan glucosides, 1 of which is new (17b). Compound 17b was obtained as a minor component of an inseparable mixture (2:1) of 2 neolignan glucosides (17a/b), and characterized as 3',4-O-dimethylcedrusin 9-O-b -glucopyranoside. Full NMR data of the known 8-O-4' neolignan glucoside, erythro-1-(4-O-b-glucopyranosyl-3-methoxyphenyl)- 2-{2-methoxyl-4-[1-(E)-propene-3-ol]-phenoxyl}-propane-1,3-diol (18) are also reported. All isolated compounds were screened for cell growth inhibition versus 3 tumor cell lines (MCF7, NCI-H460, and SF-268) and several phenylethanoid glycosides were found to possess weak antitumoral activity. The phenylethanoid glycosides were also evaluated for their free radical (DPPH) scavenging, antibacterial and antifungal activities. The free radical (DPPH) scavenging activities of verbascoside (4), isoacteoside (5), forsythoside B (10), myricoside (13) and samioside (14) were found to be comparable to that of dl-a -tocopherol. Compounds 4, 5, 10 and 14 (MIC: 500 m g/mL) as well as Leucosceptoside A (8) and 13 (MIC:1000 m g/mL) showed very weak activity against Gram (+) bacteria.
___
- ˙I. C¸ alı¸s, H. Kırmızıbekmez, D. Ta¸sdemir and P. R¨uedi, Helv. Chim. Acta, 87, 611-619 (2004).
- G.D. Gray and E. Wickstrom, Biotechniques, 21, 780-782 (1996).
- A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. Vaigro-Wolff, M. Gray-Goodrich, H. Campbell and M.R. Boyd, J. Natl. Cancer Inst., 83, 757-766 (1991).
- ˙I. Saracoglu, ¨U.S¸. Harput, M. Inoue and Y. Ogihara, Chem. Pharm. Bull., 50, 665-668 (2002).
- P.A. Villanova, ”National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard”, M7-A4, (1997).
- T. Ers¨oz, ˙I. Saraco˘glu, D. Ta¸sdemir, H. Kırmızıbekmez, A.A. D¨onmez, C.M. Ireland and ˙I. C¸ alı¸s, Z. Natur- forsch. 57c, 221-225 (2002).
- M.D. Greca, A. Molinaro, P. Monaco and L. Previtera, Phytochemistry, 35, 777-779 (1994).
- N. Matsuda and M. Kikuchi, Chem. Pharm. Bull., 44, 1676-1679 (1996).
- A. Bianco, P. Caciola, M. Guiso, C. Iavarone and C. Trogolo. Gazz. Chim. Ital., 111, 201-206 (1981).
- A. Bianco, C. Bonini, M. Guiso, C. Iavarone and C. Trogolo, Gazz. Chim. Ital., 107, 67-69 (1977).
- O. Sticher and M.F. Lahloub, Planta Med., 46, 145-148 (1982).
- J.F. Burger, E.V. Brandt and D. Ferreira, Phytochemistry, 26, 1453-1457 (1987).
- H. Sasaki, H. Taguchi, T. Endo, I. Yosioka, K. Higashiyama and H. Otomasu, Chem. Pharm. Bull., 26, 2121 (1978).
- T. Miyase, A. Koizumi, A. Ueno, T. Noro, M. Kuroyanagi, S. Fukushima, Y. Akiyama and T. Takemoto, Chem. Pharm. Bull., 30, 2732-2737 (1982).
- S. Kitagawa, H. Tsukamoto, S. Hisada and S. Nishibe, Chem. Pharm. Bull., 32, 1209-1213 (1984).
- K. Endo, K. Takahashi, T. Abe and H. Hikino, Heterocycles, 19, 261-264 (1982).
- ˙I. C¸ alı¸s, M. Hosny, T. Khalifa and P. R¨uedi, Phytochemistry, 31, 3624-3626 (1992).
- R. Cooper, P.H. Solomon, I. Kubo, K. Nakanishi, J.N. Shoolery and J.L. Occolowitz, J. Am. Chem. Soc., , 7953-7955 (1980).
- M.S. Kamel, K.M. Mohamed, H.A Hassanean, K. Ohtani, R. Kasai and K. Yamasaki, Phytochemistry, 55, 357 (2000).
- X.-N. Zhong, H. Otsuka, T. Ide, E. Hirata and Y. Takeda, Phytochemistry, 52, 923-927 (1999).
- F. Yoshizawa, T. Deyama, N. Takizawa, K. Usmanghani and M. Ahmad, Chem. Pharm. Bull., 38, 1927-1930 (1990).
- N. Matsuda, H. Sato, Y. Yaoita and M. Kikuchi, Chem. Pharm. Bull., 44, 1122-1123 (1996).
- M. Sugiyama and M. Kikuchi, Heterocycles, 36, 117-21 (1993).
- C.Z. Wang and D.Q. Yu, Phytochemistry, 48, 711-717 (1998).
- F.N. Yal¸cın, T. Ers¨oz, P. Akbay, ˙I. C¸ alı¸s, A.A. D¨onmez and O. Sticher, Turk. J. Chem., 27, 295-306 (2003).