Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana.
نویسندگان
چکیده
Malacitanolide (2), a new eudesmanolide isolated from the aerial parts of Centaurea malacitana, was characterized spectroscopically. The synthesis of 2 from cnicin (1), via the epoxide 3, confirmed the structure and stereochemistry of malacitanolide, as well as its biogenetic relationship with 1. Cytotoxic activity values for 2 are significantly higher than for 1.
منابع مشابه
Secondary metabolites from Centaurea deusta with antimicrobial activity.
The aerial parts of Centaurea deusta Ten. afforded in addition to several known compounds, mainly sesquiterpene lactones, one new eudesmanolide and one new elemane derivative. Structures of the new compounds were elucidated by spectroscopic methods. The in vitro antifungal and antibacterial activities of the isolated compounds was tested, using the microdilution method. All compounds tested sho...
متن کاملPlant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus).
The Formosan subterranean termite, Coptotermes formosanus Shiraki, is among the most devastating termite pests. Natural products derived from plant extracts were tested in a discovery programme for effective, environmentally friendly termite control agents. Among the natural products tested, vulgarone B (isolated from Artemisia douglasiana Besser), apiol (isolated from Ligusticum hultenii (Fern...
متن کاملCytotoxic Effect and Antioxidant Capacity of Different Extracts of Centaurea virgate Lam.
Background and purpose: Centaurea virgate Lam. (Gole-Gandome-Booteii or Gole-Gandome-Tarkeii in Persian) from Asteraceae, is one of the medicinal plants which is used in numerous regions, including western regions of Iran. This study aimed at investigating the cytotoxic activity and antioxidant capacity of C.virgata extracts. Materials and methods: Petroleum ether, dichloromethane, ethyl aceta...
متن کاملNew sources and antifungal activity of sesquiterpene lactones.
In the search for new sources of sesquiterpene lactones, six Centaurea species have been analyzed. The activity against the fungus Cunninghamella echinulata of (+)-cnicin (1) and (+)-salonitenolide (2), isolated from the Centaurea plants, as well as that of (+)-costunolide (3), (-)-dehydrocostuslactone (4), (-)-lychnopholide (5) and (-)-eremantholide C (6), has been evaluated. Compounds 3 and 4...
متن کاملBiomimetic total synthesis of (±)-yezo'otogirin A.
The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. Th...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Journal of natural products
دوره 60 10 شماره
صفحات -
تاریخ انتشار 1997