Annonaceous Acetogenins from the Seeds of Annona squamosa. Non-adjacent Bis-tetrahydrofuranic Acetogenins.

Fujimoto, Yoshinori; Murasaki, Chikako; Shimada, Hiroyasu; Nishioka, Seiichi; Kakinuma, Katsumi; Singh, Sanjewon; Singh, Manorama; Gupta, Yogesh; Sahai, Mahendra

doi:10.1248/cpb.42.1175

Cited by 133 publications

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“…The results revealed that the bis-THF ring analogues are much more potent than the mono-THF ring analogues and that the stereochemistry around the bis-THF ring moiety played a significant role in the inhibitory effects on complex I [89]. Compound 25 showed a similar IC 50 value as was observed for bullatacin (14) in the reduction of NADH oxidase activity (0.60-0.65 mmol NADH/min/mg of protein) in submitochondrial particles. Intriguingly, Ichimaru et al demonstrated that the inhibitory site of complex I on which Δlac-AGEs acted might be different from that at which natural AGEs did.…”

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confidence: 70%

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Historic Perspectives on Annonaceous Acetogenins from the Chemical Bench to Preclinical Trials

Liaw¹,

Wu²,

Chang³

et al. 2010

Planta Med

112

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Studies on the Annonaceous acetogenins began after the first cytotoxic acetogenin, uvaricin, was isolated in 1982. This attractive finding made many medicinal and natural product chemists direct their efforts on the isolation and identification of these classes of compounds. As more Annonaceous acetogenins were isolated, more information about them was uncovered. From their structural identification to the total synthesis of natural product analogues and from cell-based screening and molecular-based targeting to animal testing, the mechanisms of action of the Annonaceous acetogenins became clearer. The purpose of this review is to give an account of recent studies on this class of compounds and their analogues, which will aid us not only in clarifying how the Annonaceous acetogenins act but also in establishing principles for the further development of this class of compounds

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confidence: 70%

“…Fujimoto et al designed a series of mono-THF compounds with various conformations and reported their 13 C-NMR resonances, which are useful in determining the conformations of the THF ring moieties [50]. Yu et al made a single crystal of (+)-gigantecin (9) from A. coriacea Mart for an X-ray study to determine its absolute conformation [51].…”

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confidence: 99%

Historic Perspectives on Annonaceous Acetogenins from the Chemical Bench to Preclinical Trials

Liaw¹,

Wu²,

Chang³

et al. 2010

Planta Med

112

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“…Chromatographic processes permitted the separation of 10 known ACG: squamocin (1) [23], molvizarin (2) [24], motrilin (3) [24], rolliniastatin-2 (4) [25], almuñequin (5) [26], cherimolin-1 (6) [4], cherimolin-2 (7) [4], annonacin (8) [27], squamocin D (9) [28] and asiminecin (10) [29] (Figure 1), that were exhaustively purified by reversed phase HPLC to be employed in the bioassays. The ACGs 4, 6, 7 and 10 had not been previously isolated from A. squamosa.Acetogenins represent around 0.07% of the seed weight.…”

Section: Annonaceous Acetogeninsmentioning

confidence: 99%

Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith

Hidalgo¹,

Parellada²,

Blessing³

et al. 2016

JACEN

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Annonaceous acetogenins (ACG), belonging to the family Annonaceae, represent a class of bioactive compounds whose toxic effects have been reported for several species of insects. Given their insecticidal properties, we first carried out the isolation of the ACG from a Brazilian collection of the seeds of Annona squamosa (Annonaceae) and prepared their methoxy methylated (MOM) and acetylated (OAc) derivatives by chemical methods. ACG analogues were semi-synthesized and characterized by spectroscopic techniques ( 1 H and 13 C-NMR). We isolated ten natural acetogenins: squamocin, molvizarin, motrilin, rolliniastatin-2, almuñequin, cherimolin-1, cherimolin-2, annonacin, squamocin D and asiminecin. The main objective of this study is to report the antifeedant, toxic and nutritional effects of three of those natural acetogenins and their acetylated and methoxy methylated derivatives on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). The natural ACGs squamocin and molvizarin killed 100% of S. frugiperda larvae, followed by motrilin (80%). Acetylated derivatives had less toxic and nutritional effects that led to pupal mortality and adult fatal malformations. The addition of MOM derivatives to the larval diet has not toxic effects on larvae, but significantly reduces growth rate and efficiency in conversion of ingested food into biomass, affecting adult survival.

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“…6,7) The purity of the acetogenins was judged by chromatographic, 1 H-and 13 C-NMR and MS spectroscopic criteria. The reagents rotenone and NADH were purchased from Sigma.…”

Section: Materials and Reagentsmentioning

confidence: 99%

Inhibitory Activities of Three Annonaceous Acetogenins on NADH Oxidase of Chicken Liver Mitochondria

Wei

Xie

et al. 2003

Biological & Pharmaceutical Bulletin

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Annonaceous acetogenins (ACG) are natural products isolated from plants of the family Annonaceae and which have potent biological activities. Since Jolad isolated the first acetogenin (uvaricin) from Uvaria acuminata in 1982, 1) almost 400 acetogenins have been discovered, and new structural ACG will be isolated from other plants along as they are studied in depth. The reasons that ACG have drawn so much attention are not only their novel structural features but also their potent and broad activities which are seldom found in other natural compounds.The general structures of ACG are characterized by long alkyl chain compounds of 35-37 carbons containing terminal 2,4-disubstituted-g-lactone, zero to three tetrahydrofuran (THF) rings, and a number of oxygenated moieties (hydroxyls, acetoxyls, ketones, epoxides) or double bonds. According to the number and stereochemistry of THF, ACG have been classified into mono-THF, adjacent bis-THF, non-adjacent bis-THF, tri-THF, non-THF, and non-classical acetogenins. 2)Because of the wide use of ACG in pesticidal, antimalarial, antimicrobial, antiparasitic, antiprotozoal, cytotoxic activities and antitumor effects, studies on the isolation and identification of ACG as well as their action mechanism are a field presently focused on.ACG show potent activities by inhibiting NADHubiquinone oxidoreductase (complex I) in mitochondrial respiratory chain, and complex I is the largest, most complicated and important protein complex of the mitochondrial electron transport systems, which are related to ATP production.2,3) Additionally, ACG are also strong inhibitors of NADH oxidase of the plasma membrane in cancer cells, but not in rat liver plasma membrane. 4) Actually, complex I can be evaluated by NADH-ubiquinone oxidoreductase activity or by NADH oxidase activity in mitochondria, although they are not equivalent. NADH oxidase activity represents an integrated activity in which NADH is oxidized and the electrons are transferred along the respiratory chain to be finally accepted by molecular oxygen. Otherwise, the assay of NADHubiquinone oxidoreductase activity is performed with ubiquinone or its analogue as electron acceptor. As ACG only inhibit complex I, the decrease of NADH oxidase activity is directly attributed to the inhibition of complex I. 5)Most studies suggest that the terminal g-lactone is essential for the potency of ACG as complex I inhibitors, although some reports propose that the alkyl chain plays a more crucial role. However, for the roles of other ring moieties have not been sufficiently emphasized. In the present study, the roles of these structural factors are discussed by three acetogenins inhibiting NADH oxidase of chicken liver mitochondria with different ring moieties in addition to terminal g-lactone, especially the non-THF type compound exhibiting inhibitory activity, and in comparison with rotenone which is the classic inhibitor of complex I. MATERIALS AND METHODS Materials and ReagentsThree acetogenins were isolated and purified from seeds of Annona squamo...

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Annonaceous Acetogenins from the Seeds of Annona squamosa. Non-adjacent Bis-tetrahydrofuranic Acetogenins.

Cited by 133 publications

References 0 publications

Historic Perspectives on Annonaceous Acetogenins from the Chemical Bench to Preclinical Trials

Historic Perspectives on Annonaceous Acetogenins from the Chemical Bench to Preclinical Trials

Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith

Inhibitory Activities of Three Annonaceous Acetogenins on NADH Oxidase of Chicken Liver Mitochondria

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Annonaceous Acetogenins from the Seeds of Annona squamosa. Non-adjacent Bis-tetrahydrofuranic Acetogenins.

Cited by 133 publications

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Historic Perspectives on Annonaceous Acetogenins from the Chemical Bench to Preclinical Trials

Historic Perspectives on Annonaceous Acetogenins from the Chemical Bench to Preclinical Trials

Natural and Derivatized Acetogenins Promising for the Control of &lt;i&gt;Spodoptera frugiperda&lt;/i&gt; Smith

Inhibitory Activities of Three Annonaceous Acetogenins on NADH Oxidase of Chicken Liver Mitochondria

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Natural and Derivatized Acetogenins Promising for the Control of <i>Spodoptera frugiperda</i> Smith