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            "text": "504",
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            "text": "J. Nat. Prod. 1999, 62 504–540",
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            "text": "Invited Review",
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            "text": "Annonaceous Acetogenins: Recent Progress",
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            "text": "Feras Q. Alali, Xiao-Xi Liu, and Jerry L. McLaughlin [p1.5.1]",
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            "text": "Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907"
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            "text": "Received September 18, 1998"
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            "text": "The Annonaceous acetogenins are promising new antitumor and pesticidal agents that are found only in the plant family Annonaceae. Chemically, they are derivatives of long-chain fatty acids. Biologically, they exhibit their potent bioactivities through depletion of ATP levels via inhibiting complex I of mitochondria and inhibiting the NADH oxidase of plasma membranes of tumor cells. Thus, they thwart ATP-driven resistance mechanisms. This review presents the progress made in the chemistry, biology, and development of these compounds since December 1995.",
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            "text": "The Annonaceae (custard-apple family), considering its large size (130 genera and 2300 species), is chemically one of the least known of the tropical plant families.[p1.9.1] Phytochemical studies and, to a lesser extent, pharmacological studies on Annonaceous species have intensified in the last 15 years; this is largely due to the discovery of the Annonaceous acetogenins, a class of natural compounds with a wide variety of biological activities.[p1.9.2] Before 1982, most investigations centered upon the many isoquinoline alkaloids in this family. About 320 secondary natural products from 150 species belonging to 41 genera were summarized from 288 publications in 1982 by the group of Professor André Cavé in France.[p1.9.3] The discovery of uvaricin in 1982,[p1.9.4] the first of the Annonaceous acetogenins, as an in vivo active antileukemic (P-388) agent, invigorated wide interest in this family. The Annonaceous acetogenins are now one of the most rapidly growing classes of new natural products and offer exciting anthelmintic, in vivo and cytotoxic antitumor, antimalarial, antimicrobial, antiprotozoal, and pesticidal activities and special promise of becoming new chemotypes for antitumor and pesticidal agents.",
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            "text": "Structurally, the Annonaceous acetogenins are a series of C-35/C-37 natural products derived from C-32/C-34 fatty acids that are combined with a 2-propanol unit. They are usually characterized by a long aliphatic chain bearing a terminal methyl-substituted [p1.10.1]-unsaturated [p1.10.2]-lactone ring (sometimes rearranged to a ketolactone), with one, two, or three tetrahydrofuran (THF) rings located along the hydrocarbon chain and a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides) and/or double bonds being present. To a lesser extent, tetrahydropyran (THP) ring compounds and acyclic compounds are also found.[p1.10.3] The Annonaceous acetogenins are the most powerful of the known inhibitors of complex I (NADH: ubiquinone oxidoreductase) in mammalian and insect mitochondrial electron transport systems;[p1.10.4] in addition, they are potent inhibitors of NADH oxidase of the plasma membranes of cancer cells;[p1.10.5] these actions decrease oxidative, as well as, cytosolic ATP production. The consequence of such ATP deprivation is apoptosis (programmed cell death).[p1.10.6] Recently, we have shown that the acetogenins also inhibit cancer cells that are multidrug resistant (MDR),[p1.10.7] and in addition, they combat pesticide-resistant German cockroaches effectively.[p1.10.8] Thus, they thwart biological resistance.",
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            "text": "of such ATP deprivation is apoptosis (programmed cell death). [p1.11.1]Recently, we have shown that the acetogenins also inhibit cancer cells that are multidrug resistant (MDR), [p1.11.2]and in addition, they combat pesticide-resistant German cockroaches effectively.[p1.11.3] Thus, they thwart biological resistance.",
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            "text": "Since publishing our last four reviews,[p1.12.1] which summarized research on the Annonaceous acetogenins through December 1995, 10 new species of Annonaceae have been reported to contain acetogenins; they are *Annona glabra*,[p1.12.2] A. jahnii,[p1.12.3] A. spinescens,[p1.12.4] A. nutans,[p1.12.5] A. crassiflora,[p1.12.6] Goniothalamus donnaiensis,[p1.12.7] G. gardneri,[p1.12.8] Uvaria microcarpa,[p1.12.9] U. pauci-ovulata,[p1.12.10] and *Disepalum anomalum*.⁶ In our last review, we reported the isolation of mucocin,[p1.12.11] the first acetogenin containing a tetrahyropyran (THP) ring nonadjacent to a THF ring. The isolations of four more THP-bearing acetogenins have now been reported; these are muconin,[p1.12.12] which contains a nonhydroxylated THP ring adjacent to another THF ring, pyranicin and pyragonicin,[p1.12.13] the first mono-THP ring acetogenins with no THF rings at all, and jimenezin,[p1.12.14] containing a hydroxylated THP ring adjacent to a THF ring. Also newly discovered are the first hydroxylated-THF ring compounds mucoxin,[p1.12.15] goniotriocin,[p1.12.16] and donnaienin. [p1.12.17]",
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            "text": "Coriaheptocins A and B, the first heptahydroxylated acetogenins, were isolated from the roots of Annona coria-cea by the group of Cavé;[p1.13.1] we have found a nonring octahydroxylated acetogenin (unpublished), as confirmed by [p1.13.2]C NMR, CIMS, and acetylation, but we have had difficulty in locating the positions of these hydroxyls along the aliphatic chains. Recently, Cavé's group has also found several important biogenetic precursors containing two to three double bonds each separated by two carbon units.[p1.13.3] This evidence strongly suggests that the acetogenins are actually lacceroic (C-32) and ghedoic acid (C-34) derivatives. [p1.13.4]",
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            "text": "* To whom correspondence should be addressed. Tel: (765) 494-1455. Fax: (765) 494-1414. E-mail: jac@pharmacy.purdue.edu.",
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