Bielschowskysin, a gorgonian-derived biologically active diterpene with an unprecedented carbon skeleton.
نویسندگان
چکیده
Bielschowskysin is a naturally occurring diterpene isolated from the Caribbean gorgonian octocoral Pseudopterogorgia kallos. Its highly oxygenated hexacyclic structure is based on a previously undescribed tricyclo[9.3.0.0(2,10)]tetradecane ring system that was established through spectroscopic analysis and X-ray crystallographic analysis. Bielschowskysin was shown to exhibit antimalarial activity against Plasmodium falciparum as well as strong anticancer activity against two human cancer cell lines.
منابع مشابه
Cytotoxic C(35) terpenoid cryptotrione from the bark of Cryptomeria japonica.
A novel C(35)-terpene, designated as cryptotrione (1), with an unprecedented skeleton possessing an abietane diterpene with a unique bicyclic sesquiterpene, is identified from the bark of Cryptomeria japonica. The carbon skeleton of 1 represents a new structural entity, and this is an intriguing addition to the structurally diverse diterpene-sesquiterpene class. A unique biosynthetic pathway is...
متن کاملA Palladium-Catalyzed Carbo-oxygenation: The Bielschowskysin Case
An asymmetric synthesis of an advanced tetracyclic intermediate toward the synthesis of bielschowskysin (1) is described. A biomimetic [2 + 2]-photocyclization was used to establish the cyclobutane core of bielschowskysin. Macrocyclization under Heck conditions led to an unprecedented carbo-oxygenation of a 1,1-disubstituted double bond.
متن کاملNew Anti-Inflammatory 9,11-Secosterols with a Rare Tricyclo[5,2,1,1]decane Ring from a Formosan Gorgonian Pinnigorgia sp.
Pinnigorgiols D (1) and E (2), two new 9,11-secosterols with a rearranged carbon skeleton, were isolated from a Taiwan gorgonian Pinnigorgia sp. The structures of these two compounds were elucidated on the basis of spectroscopic methods and were proven to possess a tricyclo[5,2,1,1]decane ring. The new secosterols 1 and 2 displayed significant inhibitory effects on the generation of superoxide ...
متن کاملVillagorgin A and B. New Type of Indole Alkaloids with Acetylcholine Antagonist Activity from the Gorgonian Villagorgia
Gorgonians have been shown to contain a fair variety of terpene metabolitesf mainly diterpenes (cembranoids), sesquiterpenes and steroids. Paramuricea chamaeleon represents the only case of a gorgonian rich in indole alkaloids2. In connection with our investigations of biologically active marine metabolites, we focused our attention on the gorgonian Villagorgia rubra, selected for study because...
متن کاملApplying ILP to Diterpene Structure Elucidation from 13C NMR Spectra
We present a novel application of ILP to the problem of diterpene structure elucidation from 13 C NMR spectra. Diterpenes are organic compounds of low molecular weight that are based on a skeleton of 20 carbon atoms. They are of signiicant chemical and commercial interest because of their use as lead compounds in the search for new pharmaceutical eeectors. The structure elucidation of diterpene...
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:
- Organic letters
دوره 6 10 شماره
صفحات -
تاریخ انتشار 2004