Isolation and identification of a new neo-clerodane diterpenoid from Teucrium chamaedrys L.
Teucrium chamaedrys L. is an aromatic and medicinal plant used as traditional medicine. Aerial parts of the plant material were dried and extracted with hexane-dichloromethane (extract 1), ethyl acetate-dichloromethane (extract 2) and methanol-dichloromethane (extract 3) in a ratio of 1:1 at rt successively. The solvents were evaporated to give crude extracts. Extract 1 was suspended in water at 60°C then partitioned successively with hexane and ethyl acetate to give hexane and ethyl acetate portions. After the column chromatography (silica gel) of ethyl acetate extract, one new and four known compounds were isolated. The new compound was named as 1(12S,18R)-15,16-epoxy-2β,6β-dihydroxy-neo-cleroda-13(16),14-dien-20,l2-olide-l8,l9-hemiacetal (teuchamaedryn D) (4). The known compounds were teucrin A (1), dihydroteugin (2), teucroxide (3), syspirensin A (5). The chromatographic methods were also applied for extract 3 to isolate verbascoside (6) and teucrioside (7). The structure of isolated compounds was elucidated by spectroscopic methods including LC-TOF/MS, 1D NMR and 2D NMR.
a Plant Research Laboratory-A, Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University , 60240 Tokat , Turkey.
Mahfuz
M
Elmastas
a Plant Research Laboratory-A, Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University , 60240 Tokat , Turkey.
Ramazan
R
Erenler
a Plant Research Laboratory-A, Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University , 60240 Tokat , Turkey.
Besir
B
Isnac
a Plant Research Laboratory-A, Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University , 60240 Tokat , Turkey.
Huseyin
H
Aksit
a Plant Research Laboratory-A, Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University , 60240 Tokat , Turkey.
Ozkan
O
Sen
a Plant Research Laboratory-A, Department of Chemistry, Faculty of Art and Science, Gaziosmanpasa University , 60240 Tokat , Turkey.
Nusret
N
Genc
b Plant Research Laboratory-B, Department of Chemistry, Faculty of Natural Sciences, Cankiri Karatekin University , 18100 Cankiri , Turkey.
Ibrahim
I
Demirtas
D002240:Carbohydrate Sequence; D045785:Diterpenes, Clerodane / Q000737:chemistry* / Q000302:isolation & purification; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D031367:Teucrium / Q000737:chemistry*
D045785:Diterpenes, Clerodane; D010936:Plant Extracts; C000609295:teuchamaedryn D
Teucrium chamaedrys L; neo-clerodane diterpenoid; teuchamaedryn D