Department of General Chemistry 1 and Pharmacognosy 2 Istanbul University, Faculty of Pharmacy, Istanbul, Turkey Diterpenes and norditerpenes from the roots of Dorystoechas hastata A. Ulubelen 1 , A. H. Meric ¸li 2 , F. Meric ¸li 2 Received May 15, 2003, accepted September 15, 2003 Prof. Dr. Ayhan Ulubelen, University of Istanbul, Faculty of Pharmacy, TR-34116 Istanbul, Turkey Pharmazie 59: 301 – 303 (2004) Five compounds, two diterpenoids ferruginol (1), and 6,7-didehydrosempervirol (2) and two norditerpe- noids 17-hydroxycryptotanshinone (3), przewaquinone A (4) along with a new norditerpenoid cryptotanshinone 17b-oic acid (5) have been isolated from the roots of Dorystoechas hastata Boiss. et Heldr. ex Bentham (Lamiaceae ¼ Labiatae) growing wild in Southwestern Turkey (Antalya). 1. Introduction Dorystoechas hastata Boiss. et Heldr. ex Bentham (La- miaceae) is a monotypic ‘‘single genus/single species” en- demic plant growing only in the southwestern province of Turkey(Antalya). The plant is a woody shrub possessing an inflorescence which is an erect cylindrical spike with many flowered verticillasters (Davis 1971; Hedge 1971; Davis 1982). Its local name is ‘‘C ¸ alpa” and it is used as an aromatic tea (Baytop 1984). The aerial parts of D. has- tata have been studied for its essential oils (Meric ¸li and Meric ¸li 1986). In another study of the aerial parts two diterpenes, carnosol and rosmanol, and flavonoids, luteolin, luteolin 7-glucoside, and 6-methoxyluteolin 7-glucoside as well as caffeic acid and chlorogenic acid were isolated (Venturella et al. 1988). The essential oil composition of the stems and leaves and the flowering stems have been further studied (Bas ¸er and Úztu ¨rk 1992). The present study was carried out with the roots of D. has- tata and five compounds, one being new, were isolated. Two of the compounds were diterpenoids, ferruginol (1) (Cambie et al. 1971), and 6,7-didehydrosempervirol (2) (Gonzales et al. 1992), while the other three including the new compound were tanshinone type norditerpenes, 17-hydroxycryptotanshinone (3) (de la Torre et al. 1992), przewaquinone A (4) (Lee et al. 1991) and the new com- pound cryptotanshinone 17-oic acid (5). Tanshinones have been isolated mostly from Salvia miltiorrhiza Bunge (Tanshen). The plant has been known in China as a ‘‘Supergrade” medicinal herb since ancient times. Its extracts and isolated compounds have been tested for biological activities, and anti-spasmolytic, anti-arthritic, tonic, sedative and astringent activities have been estab- lished. The plant extract is also highly recommended in cases of hemorrhage, menstrual disorders and against miscarriages. In recent studies Tanshen exhibited signifi- cant improvement in vitro of the blood flow in the cor- onary circulatory system and reduction in myocardial in- farctions (Lee et al. 1987). Tanshen also exhibited cytotoxicity against five human tumor cell-lines (Ryu et al. 1997). Due to these activities the compounds ob- tained from D. hastata should have biological impor- tance, and after this first report their activities will be investigated. 2. Investigations, results and discussion The dried and powdered roots (1 kg) of the plant were extracted with acetone until extinction in a Soxhlet appa- ratus: 83 g of residue was obtained. Half of this residue was fractioned on a silica gel column eluting with petro- leum ether, followed by a CH 2 Cl 2 gradient (increasing 1% increments). The collected fractions were controlled on TLC plates and similar fractions were combined. Frac- tions 1–56 were discarded as having only oily material, while fractions 56–77 yielded ferruginol (1) and 6,7-dide- hydrosempervirol (2). Fractions 78–98 contained a num- ber of compounds in small amounts in a complex mixture, not even separable on a chromatotron plate, and therefore set aside. Fractions 99–111 yielded przewaquinone A (4) and the new compound cryptotanshinone 17b-oic acid (5) and fractions 112–121 yielded 17-hydroxycryptotanshi- none (3). Other fractions were polar mixtures and con- tained no diterpenoids. They were set aside for possible future studies. The new compound cryptotanshinone 17b-oic acid (5) was a dark orange colored amorphous compound with an optical rotation [a] 27 D ¼25  (c ¼ 0.5, CHCl 3 ). The mo- ORIGINAL ARTICLES Pharmazie 59 (2004) 4 301 R= COOH R= C H 2 OH R OH O 5 4 3 O O CH 2 OH O O 2 1 OH O