Mitregenin, a new Annonaceous acetogenin from Mitrephora maingayi

From Mitrephora maingayi, a new C21-type Annonaceous acetogenin (1) has been isolated, along with a biogenetically related known compound, oropheic acid (2). Their structures were elucidated on the basis of extensive spectroscopic analysis. The insecticidal activity of 1 was also assessed.     

Calamistrin E, the First Annonaceous Acetogenin with Double Bond in Aliphatic Chain from Genus Uvaria

Annonaceous acetogenins are considered as the main components with cytotoxicity inthe plants of Annonaceae family. The genus Uvaria is one of the main plants containingAnnonaceous acetogenins, and more than fifty acetogenins have been isolated from eightspecies of the title genus"', however, acetogenins with double bond in the aliphatic chainhas not yet been reported. In this paper we report the structure elucidation of calamistrinE (l), a new acetogenin bearing one double bond besides a tetr…     

An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogue

[reaction: see text] A synthesis of the Annonaceous acetogenin asimicin and a side-chain analogue has been achieved by a highly convergent route in which Grubbs cross-metathesis plays a key role.     

Convergent total synthesis of squamostolide

A convergent total synthesis of the Annonaceous acetogenin squamostolide, in a longest linear sequence of nine steps from d-mannitol, is reported. Central to the efficiency of the synthesis is a highly selective tandem ring-closing/cross metathesis step in which lactone formation and fragment coupling are accomplished.     

Muricatenol, a Linear Acetogenin from Annona muricata (Annonaceae)

Annonaceous acetogenins (polyketides) are a group of extensively investigated naturalcompounds possessing antitumor, antiparasitic and pesticidal activities. Over 350acetogenins have been isolated and most of them have one to three tetrahydrofuran (THF)cores, several hydroxyls and a terminal y-lactone ring. As part of our investigation ofthe title species, we have reported four new C,, acetogeninst muricatalin',muricatalicin=, annonacin-B' and murihexol 2' and four known acetogenins4 annonac…     

Total synthesis of 34-hydroxyasimicin and its photoactive derivative for affinity labeling of the mitochondrial complex I

The asymmetric total synthesis of the 34-hydroxyasimicin and its 3-(4-benzoylphenyl)propionate ester was achieved by means of a convergent synthetic strategy. This ester, which contains eight asymmetric centers, represents the first photoaffinity-labeling agent that is derived from an Annonaceous acetogenin. The key transformations in the synthesis include the Sharpless asymmetric dihydroxylation reaction, the Wittig olefination reaction, an oxidative cyclization reaction with rhenium(vii) oxide, the Williamson etherification reaction, and a palladium-catalyzed cross-coupling reaction. Use of the target molecule for photoaffinity-labeling studies of bovine mitochondrial NADH-ubiquinone oxidoreductase (Complex I) may shed light on the structure/function of this intricate enzyme and on the origin of the high antitumor activity exhibited by the Annonaceous acetogenins.     

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

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.     

3 + 2]-annulation reactions of chiral allylsilanes and chiral aldehydes. studies on the synthesis of bis-tetrahydrofuran substructures of annonaceous acetogenins

[Structure: See text] Double asymmetric [3 + 2]-annulation reactions of chiral beta-silyloxyallylsilanes with chiral 2-tetrahydrofuranyl carboxaldehydes have been studied, leading to the stereocontrolled synthesis of six diastereomeric bis-tetrahydrofuran structures corresponding to the core subunits of members of the Annonaceous acetogenin family of natural products. Transition-state models are proposed to account for the stereoselectivity of the double-stereodifferentiating [3 + 2]-annulation reactions.     

New Acetogenins from the Seeds of Annona coriacea

From the hexane and MeOH extracts of Annona coriacea Mart . (Annonaceae) seeds, two novel acetogenins, coriapentocins A and B ( 1 and 2 , resp.) were isolated. The known acetogenin bullacin ( 3 ) was also isolated from the hexane extract. The structures of compounds 1 – 3 were elucidated by NMR and MS analysis, and relative configurations were established by comparison with literature data.     

阿蒂莫耶根番荔枝内酯的研究

从阿蒂莫耶(AnnonaatemoyaHort)根中分离到一个新的含有四个羟基的邻双四氢呋喃环型番荔枝内酯(Annonaceousacetogenin)-阿蒂莫耶素C(AtemoyacinC),同时分离到五个已知番荔枝内酯isocherimolin-1、bullatacin、rollinicin、almunequin和atemoyacinB。     

Muricatin A和Muricatin B刺果番荔枝中的两个新番荔枝内酯

从刺果番荔枝(Annonamuricata)的种子分离得到两个新成分,此两成分及其衍生化物经光谱分析,鉴定为两个新番荔枝肉酯,命名为MuricatinA和MuricatinB。它们属无THF环番荔枝内酯。     

阿蒂莫耶素D的分离与结构

从阿蒂莫耶(Annonaatemoya(I)Hort)种子中分离到一个新的邻双四氢呋喃环型番荔枝内酯(Annonaceousacetogenin)-阿蒂莫耶素D(AtemoyacinD),同时分离到四个已知番荔枝内酯neo-annoninB、neodesacetyluvaricin、parviflorin和annonacin。     

Chemical Biology Studies on Molecular Diversity of Annonaceous Acetogenins

Annonaceous acetogenins, isolated from the Annonaceae plants, have been attracting worldwide attention in recent years due to their biological activities, especially as growth inhibitors of certain tumor ceils [ 1 ]. They have been shown to function by blocking complex I in mitochondria [2] as well as ubiquinone-linked NADPH oxidase in the cells of specific tumor cell lines, including some multidrug-resistant ones [3]. These features make these acetogenins excellent leads for the new antitumor agents. In our previous work, the compounds 1a to 1d (Figure 1), which relies on structure simplification while maintaining all essential functionalities of the acetogenins, was in vitro tested against several human solid tumor cell lines and showed interesting cell selectivity [4]. All four analogues show remarkable activity against the HCT-8 and HT-29 cell lines, while compound 1c was found the best [4bi. In order to further investigate the effects of key structural features, a convergent parallel fragments assembly strategy was developed [4e]. In addition, the biological relevancies of typical annonaceous acetogenin mimetics were also studied [4f].     

An Overview of the Chemical Characteristics,Bioactivity and Achievements Regarding the Therapeutic Usage of Acetogenins from Annona cherimola Mill.

Annona cherimola Mill., or the custard apple, is one of the species belonging to the Annonaceae family, is widely used in traditional medicine, and has been reported to be a valuable source of bioactive compounds. A unique class of secondary metabolites derived from this family are Annonaceous acetogenins, lipophilic polyketides considered to be amongst the most potent antitumor compounds. This review provides an overview of the chemical diversity, isolation procedures, bioactivity, modes of application and synthetic derivatives of acetogenins from A. cherimola Mill.     

紫玉盘素B的分离与鉴定

从紫玉盘(Uvaria microcarpa)种子中首次分离得到二个白色蜡状固体, 经光谱分析鉴定: 一个为新的番荔枝内酯-紫玉盘素B(Microcarpacin B), 一个为已知的番荔枝内酯-Rollinicin。     

Atemoyacin A: A new bis-tetrahydrofuranyl annonaceous acetogenin from Annona atemoya H.

Atemoyacin A, a new annonaceous acetogenin was isolated from the alcoholic extract of the seeds of Annona atemoya Hort (Annonaceae). Its structure and relative configuration were elucidated on the basis of the spectral analysis.     

Polyporolide, a new acetogenin from the mycelial culture of a Polyporus fungus

A new acetogenin, polyporolide (1), was isolated from the mycelial solid cultures of a Polyporus basidiomycete. Its structure was elucidated as 4-hydroxy-5-(1-hydroxyhexyl)-dihydrofuran-2-one by spectroscopic methods. Its toxicity to brine shrimps was assessed.     

Enantioselective total synthesis of the potent antitumor agent (-)-mucocin using a temporary silicon-tethered ring-closing metathesis cross-coupling reaction

The enantioselective total synthesis of the annonaceous acetogenin (-)-mucocin (1) was accomplished using a triply convergent 12-step sequence (longest linear sequence) in 13.6% overall yield. This represents the first application of the temporary silicon-tethered (TST) ring-closing metathesis (RCM) cross-coupling reaction and the enantioselective alkyne/aldehyde addition to the synthesis of a complex annonaceous acetogenin. Moreover, all three fragments required for the coupling reactions are conveniently prepared in 5-6 steps from two readily available enantiomerically enriched epoxides. Finally, this synthesis stimulated the development of a new approach for the construction of 3-hydroxy-2,6-disubstituted tetrahydropyrans, using the bismuth tribromide-mediated reductive etherification reaction, which represents a motif that is prevalent in a wide range of pharmacologically significant natural products.     

Total synthesis of (+)-muconin

(+)-Muconin (1), isolated from the leaves of Rollinia mucosa (Jacq.) Baill. (Annonaceae), is a sequential THF/THP-possessing acetogenin that exhibits potent and selective in vitro cytotoxicity toward pancreatic and breast tumor cell lines. In this study, a new route was established for obtaining (+)-muconin (1) starting with (-)-muricatacin (2), a compound recently synthesized via the novel alpha-C-H hydroxyalkylation and alpha'-C-H oxidation of tetrahydrofuran.     

Mimicry of annonaceous acetogenins: enantioselective synthesis of a (4R)-hydroxy analogue having potent antitumor activity

The (4R)-hydroxylated analogues of annonaceous acetogenin mimicking compound 2 were designed and synthesized structurally on the basis of the naturally occurring annonaceous acetogenin bullatacin, which was discovered as a typical member of the novel family of polyketides with potent cytotoxicity, antitumoral, and other biological activities. The preliminary screenings show that the IC(50) values of 2 were 1.6 x 10(-3) and 8 x 10(-2) microg/mL against HT-29 and HCT-8, respectively. A remarkable enhancement effect was observed by the activity comparison of 1c and its (4R)-hydroxylated analogue 2.