Ufuk Sönmez

Chemical and biological evaluation of genus teucrium

Abstract The genus Teucrium is represented by about 300 species in the world and 27 species in Turkey, 8 of them being endemic. Teucrium species are rich source of neo-clerodane diterpenoids. Although several furanoid diterpenes with the neo-clerodane skeleton have been isolated from many plants, the genus Teucrium is the most abundant natural source of these compounds, therefore Teucrium species are accepted as chemotaxonomic markers for neo-clerodanes. Chemical investigations on this genus showed that some of the species also contain rearranged neo-clerodane or abietane diterpenes, sesquiterpenes, triterpenes and steroids. Flavonoids and aromatic compounds, although not as abundant as in the genus Salvia from the same family, are also found in the genus Teucrium. In this review, general chemical properties of neo-clerodanes isolated from Teucrium species are given with their stereochemical studies. Teucrium species have been used for more than 2000 years as medicinal plants. They showed diuretic, diaphoretic, antiseptic and antipyretic activities. Antifeedant activities of some species previously studied against Spodeptera littoralis were presented herein. Teucrium species are used as hypoglycemic agents in North Africa and Saudi Arabia. They also possess antispasmolitic activity and used in the treatment of stomach aches. Some of the Teucrium extracts exhibited central nervous system depressant action.

Diterpenoids from the roots of Salvia sclarea

Abstract The roots of Salvia sclarea yieded two triterpenoids, 3-oxo-oleanolic acid, α-amyrin, a steroid sitosterol and 12 diterpenoids, two of which are new. The known diterpenoids are ferruginol, salvipisone, microstegiol, candidissiol, 2,3-dehydrosalvipisone, aethiopinone, 1-oxoaethiopinone, salvinolone, cryptojaponol, Δ 7 -manool, and the new compounds are sclareapinone and acetylsalvipisone. The structures were established by spectral data and also by TLC comparison for the known compounds.

Terpenoids and flavonoids from Salvia cyanescens

Abstract A new diterpenoid 12-isopentenyl-3-oxosalvipisone was isolated from the aerial parts of S. cyanescens along with the known terpenoids and flavonoids.

An abietane diterpene and two phenolics from Salvia forskahlei

From the roots of Salvia forskahlei a new diterpenoid, forskalinone, two new aromatic compounds, the octanol esters of cis- and trans-4-O-methyl-caffeic acid dimers, were isolated together with the known compounds stigmast-3-one, sitosterol and alpha-amyrin. The structures of the new and the known compounds were established by spectral data. The antimicrobial activity of forskalinone and the dimeric cinnamic acid esters was tested against standard bacterial strains and a yeast, namely Bacillus subtilis ATCC 6633, Staphylococcus aureus 6538P, S. epidermidis ATCC 12228, Proteus mirabilis ATCC 14153, Escherichia coli ATCC 8739, Klebsiella pneumonia ATC 4352, Pseudomonus aeruginosa ATCC 9027, Enterococcus faecalis ATCC 29212, beta-haemolytic Streptococcus and Candida albicans ATCC 10231. Forskalinone showed moderate resistance against S. epidermidis (670 micrograms ml-1) and slight activity against E. faecalis (168 micrograms ml-1). trans-4-O-Methyl-caffeic acid dimer octanol ester was inactive while the cis isomer showed a slight activity against C. albicans (156 micrograms ml-1).

Abietane diterpenes from Salvia napifolia

Abstract From the acetone extract of the roots of Salvia napifolia , eight known diterpenoids—horminone, 7-acetylhorminone, ferruginol, pachystazone, cryptanol, cryptojaponol, sugiol and microstegiol—and five new diterpenes—6,12,14-trihydroxyabieta-6,8,11,12-tetraen, 7,20-epoxyroyleanone, 1-oxoferruginol, 6-oxoferruginol and 11,12-dioxoabieta-8,13-dien—were obtained. The structures of the new and the known compounds were established by spectral methods.

Diterpenoids and triterpenoids from Salvia multicaulis

Abstract Two new diterpenoids, 3-oxo-12-methoxy-14-hydroxyabieta-8,11,13-triene and 6-oxo-12-per-oxyabieta-8,11,13-triene, a new steroid brassicasterone and a new aromatic ester 4,4′- bis benzoic acid heptyl ester were obtained from the roots of Salvia multicaulis . In addition six known triterpenoids, six diterpenoids and sitosterol were identified.

Norsesterterpenes and diterpenes from the aerial parts of Salvia limbata

From the aerial parts of Salvia limbata, two new diterpenes (limbinal and acetyllimbinol) and two new dinorsesterterpenes (6-dehydroxy-yosgadensonol and 6-dehydroxy-13-epi-yosgadensonol) were isolated in addition to eight known terpenoids and four flavonoids. The structures of the new and the known compounds were established by spectral data.

Terpenoids from Salvia nemorosa

Abstract In addition to known compounds, a new diterpenoid, nemorosin and a new triterpenoid, salvinemorol were isolated from the aerial parts of Salvia nemorosa L. The structures of the known and new compounds were established by spectral data.

Alkaloids and Coumarins From Haplophyllum Thesioides

Abstract The aerial parts of Haplophyllum thesioides yielded a new alkaloid, thenaptosine [4,5-dimethoxy-11-metriylfuro(2,3-c)acridin-6(15H)-on] and a new coumarin, thesiolen (4-methoxyangelicin) in addition to known alkaloids, kokusaginine, skimmianine, pteleine, nkolbisine, heliparvifoline and flindersine as well as known coumarins, seseline, scaporon and angustifolin.

Diterpenoid alkaloids from Delphinium uncinatum

Abstract From the aerial parts of Delphinium uncinatum a new diterpenoid uncinatine and four known norditerpenoid alkaloids have been isolated. By spectral data ( 1 H and 13 C NMR) the known compounds were established as 14-acetylperegrine, 14-acetylvirescenine, condelphine and delbrusine. The structure of the new alkaloid was deduced by 1D and 2D NMR techniques.