Recent advances in annonaceous acetogenins

Lu, Zhou; Ye, Qing; Oberlies, Nicholas H.; Shi, Guoen; Gu, Zhe‐Ming; He, Kan; McLaughlin, Jerry L.

doi:10.1039/np9961300275

Cited by 355 publications

(325 citation statements)

References 110 publications

Supporting

Mentioning

320

Contrasting

Unclassified

Order By: Relevance

“…A mixture of 18 (10 mg, 16 µmol) and 10% Pd/C (5 mg) in ethanol (2 mL) was stirred under a H 2 atmosphere at room temperature for 8 h. The crude product was purified by silica gel column chromatography (hexane-EtOAc, 4:1) to afford 3 (10 mg, 98%) as a colorless oil. 1 The synthetic procedures of these compounds are described taking compound 7 as an example (Scheme 1D). To a solution of 4-(4-n-butylphenoxy)-1-butyne (133 mg, 0.67 mmol), which was prepared by the method outlined in Scheme 1C, in dry THF (3 mL) at -78°C was added a solution of n-BuLi (1.6 M in hexane, 0.4 mL, 0.64 mmol).…”

Section: Synthetic Procedures (A) Compoundmentioning

confidence: 99%

“…The residue was purified by silica gel column chromatography (hexane-EtOAc, 7:3) to give 6 (34 mg, 85%). 1 (E) Compound 14. The synthetic procedures of compound 14 are outlined in Scheme 1F.…”

Section: Synthetic Procedures (A) Compoundmentioning

confidence: 99%

“…The reaction mixture was filtered over Celite, solvents were removed under vacuum, and the crude product was purified by silica gel column chromatography (EtOAc, 100%) to afford 14 (25 mg, 66%). 1 Measurement of Complex I ActiVity. Bovine heart submitochondrial particles (SMP) were prepared by the method of Matsuno-Yagi and Hatefi (14) using a sonication medium containing 0.25 M sucrose, 1 mM succinate, 1.5 mM ATP, 10 mM MgCl 2 , 10 mM MnCl 2 , and 10 mM Tris-HCl (pH 7.4) and stored in a buffer containing 0.25 M sucrose and 10 mM Tris-HCl (pH 7.4) at -84°C.…”

Section: Synthetic Procedures (A) Compoundmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and Inhibition Mechanism of Δlac-Acetogenins, a Novel Type of Inhibitor of Bovine Heart Mitochondrial Complex I

et al. 2004

View full text Add to dashboard Cite

We have synthesized ∆lac-acetogenins that are new acetogenin mimics possessing two n-alkyl tails without an R, -unsaturated γ-lactone ring and suggested that their inhibition mechanism may be different from that of common acetogenins [Hamada et al. (2004) Biochemistry 43, 3651-3658]. To elucidate the inhibition mechanism of ∆lac-acetogenins in more detail, we carried out wide structural modifications of original ∆lac-acetogenins and characterized the inhibitory action with bovine heart mitochondrial complex I. In contrast to common acetogenins, both the presence of adjacent bis-THF rings and the stereochemistry around the hydroxylated bis-THF rings are important structural factors required for potent inhibition. The inhibitory potency of a derivative possessing an n-butylphenyl ether structure (compound 7) appeared to be superior to that of the original ∆lac-acetogenins and equivalent to that of bullatacin, one of the most potent natural acetogenins. Double-inhibitor titration of steady-state complex I activity showed that the extent of inhibition of compound 7 and bullatacin is not additive, suggesting that the binding sites of the two inhibitors are not identical. Competition tests using a fluorescent ligand indicated that the binding site of compound 7 does not overlap with that of other complex I inhibitors. The effects of compound 7 on superoxide production from complex I are also different from those of other complex I inhibitors. Our results clearly demonstrate that ∆lac-acetogenins are a novel type of inhibitor acting at the terminal electron-transfer step of bovine complex I.

show abstract

Section: Synthetic Procedures (A) Compoundmentioning

confidence: 99%

Section: Synthetic Procedures (A) Compoundmentioning

confidence: 99%

Section: Synthetic Procedures (A) Compoundmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Inhibition Mechanism of Δlac-Acetogenins, a Novel Type of Inhibitor of Bovine Heart Mitochondrial Complex I

et al. 2004

View full text Add to dashboard Cite

show abstract

“…These acetogenins are non-toxic to normal cells, but are highly toxic to cancer cells (Oberlies et al, 1995). Acetogenins from the soursop plant are usually extracted using ethanol as the organic solvent (Zeng et al, 1996). These compounds, collectively, have shown antitumor, parasiticidal, pesticidal, and antimicrobial activities (McLaughlin, 2008).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial and Phytochemical Analysis of Methanolic and Aqueous Extract of Annona muricata (Leaf and Fruit)

Vinothini¹,

Growther²

2016

Int.J.Curr.Microbiol.App.Sci

View full text Add to dashboard Cite

“…Extensive studies on AGEs have indicated that these naturally occurring compounds possess a broad spectrum of bioactivity, including anticancer, antiparasitic, insecticidal and immunosuppressive effects. In 27 years, more than 500 AGEs were isolated from various parts of the plants of this family [7][8][9][10]. These bioactive AGEs became more important, particularly in pharmaceutical research [11,12].…”

mentioning

confidence: 99%

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

Liaw¹,

Wu²,

Chang³

et al. 2010

Planta Med

113

View full text Add to dashboard Cite

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

show abstract

Recent advances in annonaceous acetogenins

Cited by 355 publications

References 110 publications

Synthesis and Inhibition Mechanism of Δlac-Acetogenins, a Novel Type of Inhibitor of Bovine Heart Mitochondrial Complex I

Synthesis and Inhibition Mechanism of Δlac-Acetogenins, a Novel Type of Inhibitor of Bovine Heart Mitochondrial Complex I

Antimicrobial and Phytochemical Analysis of Methanolic and Aqueous Extract of Annona muricata (Leaf and Fruit)

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

Contact Info

Product

Resources

About