Annonaceae acetogenins from

Cave, A., Figadere, B., Laurens, A., and Cortes, D. Acetogenins from Annonaceae, In Progress in Chemistry of Organic Natural Products, Hertz, W., Kirby, G.W., Moore, R.E., Steglich, W., and Tamm, C., Eds., Springer, New York, 81-288, 1997. 

Espositi, M.D., Ghelli, A., Batta, M., Cortes, D., and Estornell, E. Natural substances (acetogenins) from the family Annonaceae are potent inhibitors of mitochondrial NADH dehydrogenase (complex I). Biochem.., 301, 161, 1994. 

In the total syntheses of squamocin A and squamocin D, acetogenins from Annonaceae, a double cyciization has been demonstrated to be feasible for the assembly of bis-tetrahydrofuran motifs (Equation 71) <2000EJ01889>. Intramolecular dehydration to afford tetrahydrofurans can efficiently be carried out by the Mitsunobu reaction <2003JOC4422> and a cationic platinum-catalyzed dehydration <2005SL152>. 

Rupprecht, j. K., C. Chang, J. M. Cassady, J. L. McLaughlin, K. L. Mikolajczak, and D. Weisleder, Asimicin, a new cytotoxic and pesticidal acetogenin from the pawpaw, Asimina triloba (Annonaceae), Heterocycles, 24, 1197-1201 (1986). 

Lu Z, Yan Z, McLaughlin JL. Gigantransenins A, B, and C, novel mono-THF acetogenins bearing trans-double bonds, from Goniothalamus giganteus (Annonaceae). Tetrahedron Lett 1996 37 5449-5452. 

Solanaceae), acts as competitive inhibitor for ubiquinone in Complex I. Methyl capsaicin is more potent than capsaicin, indicating that the phenolic OH is not essential for the activity [297]. Other natural inhibitors of Complex I are annonaceous acetogenins. These compounds belong to a wide group of natural products isolated from several species of the Annonaceae family, which include more than 250 molecules with diverse chemical structures. Among the various classes, it seems that monotetrahydrofuranic derivatives are less potent than other acetogenins [296, 299]. 

The Annonaceous acetogenins are an important new group of long-chain fatty acid derivatives found exclusively in the plant family, Annonaceae. Nearly 400 compounds from this... 

A wide variety of natural products has been isolated from the Annonaceae. However, the report in 1982 of the isolation of the acetogenin uvaricin (1) from Uvaria accuminate was the first example of what is now a large and growing series of acetogenins found in these sources. More than one-hundred examples have been reported in the intervening decade.3- That these compounds often exhibit remarkably potent cytotoxic and other biological activity has fueled interest in this class. 

Annonaceous acetogenins are a bio-potent class of natural compounds isolated from Annonaceae plants. Since the first bioactive Annonaceous acetogenin, uvaricin, was found from the roots of Uvaria accuminata (Annonaceae) by Jolad et al. in 1982 (Fig. 1) [66], more than 350 Annonaceous acetogenins have been isolated in the last two decades. Generally, it has been reported that Annonaceous acetogenins possess a broad spectrum of bioactivities, such as anticancer, antiparasitic, insecticide, and immunosuppressive effects. 

Annonaceous acetogenins, potent bioactive secondary metabolites from several species of Annonaceae, usually contain 35 or 37 carbon atoms, one or two tetrahydrofiiran rings, and a 7-lactone with five to eight carbinol asymmetric centers. Corossolone (890), a naturally... 

The known chemistry of the Annonaceae is mainly based on the work of Cave and Leboeuf on the benzyhsoquinoline alkaloids. After this work, several papers were published which evidenced the presence of alkaloids derivatives of isoquinolines. Approximately 800 alkaloids of the types isoquinolines, protoberberine, aporphine, and others were isolated from different genera of the Aimonaceae. Previous chemical and pharmacological investigations have indicated that bisbenzylisoquinolines are important bioactive components existing in plants of the Annonaceae family. Other terpenes, flavonoids, Hgnans, acetogenins, and some aromatic compounds are also found in the family but the alkaloids are the major chemical constituents. 

Rieser MJ, Kozlowski JF, Wood KV, McLaughlin JL. Muri-catacin a simple biologically active acetogenin derivative from the seeds annora muricata (annonaceae). Tetrahedron Lett. 1991 32(9) 1137-1140. 

---