mucocin and isomurisolenin

mucocin has been researched along with isomurisolenin* in 2 studies

Other Studies

2 other study(ies) available for mucocin and isomurisolenin

Article	Year
Quinone-annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids. Chemistry (Weinheim an der Bergstrasse, Germany), 2001, Mar-02, Volume: 7, Issue:5 The natural product hybrids quinone-mucocin and quinone- squamocin D were synthesized. In these hybrids, the butenolide unit of the annonaceous acetogenins mucocin and squamocin D is exchanged for the quinone moiety of the natural complex I substrate ubiquinone. For both syntheses, a modular, highly convergent approach was applied. Quinone-mucocin was constructed out of a tetrahydropyran (THP) component 1, a tetrahydrofuran (THF) unit 2, and a quinone precursor 3. A stereoselective, organometallic coupling reaction was chosen for the addition of the THP unit to the rest of the molecule. In the final step, the oxidation to the free quinone was achieved by using cerium(IV) ammonium nitrate (CAN) as the oxidizing agent. Quinone-squamocin D was assembled in a similar manner, from the chiral side chain bromide 16, the central bis-THF core 17, and the quinone precursor 18. Inhibition of complex I (isolated from bovine heart mitochondria) by the quinone acetogenins and several smaller building blocks was examined; quinone mucocin and quinone-squamocin D act as strong inhibitors of complex I. These results and the data from the smaller substructures indicate that other substructures of the acetogenins besides the butenolide group, such as the polyether component and the lipophilic left-hand side chain, are necessary for the strong binding of the acetogenins to complex I. Topics: Animals; Benzoquinones; Cattle; Electron Transport Complex I; Enzyme Inhibitors; Furans; Lactones; Mitochondria, Heart; NADH, NADPH Oxidoreductases; Pyrans; Quinones	2001
A convergent total synthesis of (-)-mucocin: an acetogenin from Annonaceae. Chemistry (Weinheim an der Bergstrasse, Germany), 2000, Jul-03, Volume: 6, Issue:13 A total synthesis of the Annonaceous acetogenin mucocin has been accomplished. The synthesis follows a convergent strategy, wherein at a very late stage the left part of the molecule is connected with the right part. The key reaction is the stereocontrolled addition of an organomagnesium compound 2 to the aldehyde 3. The THP ring of mucocin is build by a 6-endo epoxide cyclization of an epoxyacetonide precursor (16 --> 17). The new modular synthetic approach developed herein should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogues. Topics: Antibiotics, Antineoplastic; Furans; Indicators and Reagents; Lactones; Plants, Medicinal; Pyrans	2000

Article

Year

Quinone-annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids.

Chemistry (Weinheim an der Bergstrasse, Germany), 2001, Mar-02, Volume: 7, Issue:5

The natural product hybrids quinone-mucocin and quinone- squamocin D were synthesized. In these hybrids, the butenolide unit of the annonaceous acetogenins mucocin and squamocin D is exchanged for the quinone moiety of the natural complex I substrate ubiquinone. For both syntheses, a modular, highly convergent approach was applied. Quinone-mucocin was constructed out of a tetrahydropyran (THP) component 1, a tetrahydrofuran (THF) unit 2, and a quinone precursor 3. A stereoselective, organometallic coupling reaction was chosen for the addition of the THP unit to the rest of the molecule. In the final step, the oxidation to the free quinone was achieved by using cerium(IV) ammonium nitrate (CAN) as the oxidizing agent. Quinone-squamocin D was assembled in a similar manner, from the chiral side chain bromide 16, the central bis-THF core 17, and the quinone precursor 18. Inhibition of complex I (isolated from bovine heart mitochondria) by the quinone acetogenins and several smaller building blocks was examined; quinone mucocin and quinone-squamocin D act as strong inhibitors of complex I. These results and the data from the smaller substructures indicate that other substructures of the acetogenins besides the butenolide group, such as the polyether component and the lipophilic left-hand side chain, are necessary for the strong binding of the acetogenins to complex I.

Topics: Animals; Benzoquinones; Cattle; Electron Transport Complex I; Enzyme Inhibitors; Furans; Lactones; Mitochondria, Heart; NADH, NADPH Oxidoreductases; Pyrans; Quinones

2001

A convergent total synthesis of (-)-mucocin: an acetogenin from Annonaceae.

Chemistry (Weinheim an der Bergstrasse, Germany), 2000, Jul-03, Volume: 6, Issue:13

A total synthesis of the Annonaceous acetogenin mucocin has been accomplished. The synthesis follows a convergent strategy, wherein at a very late stage the left part of the molecule is connected with the right part. The key reaction is the stereocontrolled addition of an organomagnesium compound 2 to the aldehyde 3. The THP ring of mucocin is build by a 6-endo epoxide cyclization of an epoxyacetonide precursor (16 --> 17). The new modular synthetic approach developed herein should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogues.

Topics: Antibiotics, Antineoplastic; Furans; Indicators and Reagents; Lactones; Plants, Medicinal; Pyrans

2000