Three Novel Chemical Compounds of Annonaceous Acetogenins from the Seeds of Annona squamosa

Seven compounds (A1--A7) were isolated from the seeds of Annona squamosa L. Three of them, A2, A3, and A5, are new compounds of annonaeeous aeetogenins, and they were name neo-desacetyluvaricin (A2), neo-annonin B (A3) and neo-reticulatacin A (A5), respectively.     

Annonaceous acetogenins: Precursors from the seeds of Annona squamosa

From the less polar fractions of an Annona squamosa (Annonaceae) seeds extract, four new annonaceous acetogenins, dieposabadelin (1), squamocenin (2), lepirenin (3) and dotistenin (4), were isolated, along with sixteen known acetogenins: corepoxylone, diepomuricanins A and B, dieporeticenine, tripoxyrollin, bullatencin, glabrencin B, reticulatains-1, -2, uvariamicins I, II, III, erythrosolamin, annotemoyin-1 and -2, and solamin. Fourteen are reported for the first time in this species.     

Novel cytotoxic monotetrahydrofuranic Annonaceous acetogenins from Annona montana

Four new monotetrahydrofuranic Annonaceous acetogenins, montalicins G (1) and H (2) and monlicins A (3) and B (4), and two new linear acetogenins, (+)-monhexocin (5) and (-)-monhexocin (6), as well as three known compounds, murisolin (7), 4-deoxyannomontacin (8), and muricatacin (9), were isolated from the seeds of Annona montana by high performance liquid chromatographic (HPLC) method. The absolute stereochemical structures of new isolates were elucidated and characterized by spectral and chemical methods. Interestingly, these compounds show special cytotoxicity against human hepatoma cells, Hep G2.     

番荔枝化学成分研究(7)

从番荔枝（Ａｎｎｏｎａ ｓｑｕａｍｏｓａ Ｌ．）种子中得到化合物１、２和４,化合物２和４分别为已知化合物ｍｏｔｒｉｌｉｎ（莫垂林,２）和ｂｕｌｌａｔａｎｏｃｉｎ（布拉他诺辛,４）。化合物１的化学结构经ＩＲ、ＭＳ、＾１Ｈ ＮＭＲ及＾１３Ｃ ＮＭＲ谱分析及其乙酰化物（１ａ）的ＭＳ、＾１Ｈ ＮＭＲ谱分析推定如（１）式并命名为２２－表－莫维查灵（２２－ｅｐｉ－ｍｏｌｖｉｚａｒｉｎ）。     

Monotetrahydrofuran annonaceous acetogenins from the seeds of Annona squamosa

Three new monotetrahydrofuran annonaceous acetogenins, Annosquamins A–C (1–3) were isolated from the 95% EtOH extract of Annona squamosa seeds, in addition to the known compounds, solamin, annotemoyin-1, uvariamicin-II, uvariamicin-III. Their structures were elucidated by spectroscopic analysis and the relative configurations of bearing tetrahydrofuran rings were established by comparing NMR data with model compounds.     

番荔枝化学成分研究(6)

自番荔枝（ ＡｎｎｏｎａｓｑｕａｍｏｓａＬ．） 种子中得到化合物１ 和２ , 化合物２ 是已知的ｂｕｌｌａｔａｃｉｎｏｎｅ （２ , ４－ 顺式和反式－ ｂｕｌｌａｔａｃｉｎｏｎｅ 的混晶） , １ 是新化合物, 命名为番荔枝塔亭丁（ｓｑｕａｍｏｓｔａｔｉｎ Ｄ） , 其结构经ＩＲ、ＭＳ、１Ｈ－ ＮＭＲ和１３ＣＮＭＲ谱解析推定如（１） 式。     

Studies on the Chemical Constituents of Annona squamosa(5)

From the seeds of Annona squamosa L.,three compounds were obtained,in which compounds i and 2 are known compounds,i.e. bullatacin and annonin I,respectively.Compounds 3 is a new non -adjacent bis -tetrahydrofuranyl annonaceous acetogenin,named squamostatin C.Based on the analysis of IR MS,1H NMR and 13 C NMR spectra,the structure of compound 3 was elucidated as (3).     

Annonaceous acetogenins from the leaves of Annona montana

A novel Annonaceous acetogenin, montanacin F, with a new type of terminal lactone unit, was isolated from the leaves of Annona montana. Its structure was determined on the basis of spectral evidences and chemical methods, and a possible biosynthetic pathway was discussed. In addition, the cytotoxicity of montanacin F was evaluated in vitro against Lewis lung carcinoma (LLC) tumor cell lines. Furthermore, the previously isolated cytotoxic acetogenin annonacin against LLC was examined for in vivo antitumor activity with LLC tumor cells.     

Three new anti-proliferative Annonaceous acetogenins with mono-tetrahydrofuran ring from graviola fruit (Annona muricata)

Bioassay-guided fractionation of the fruit powder of graviola (Annona muricata) yielded three novel compounds: muricins J, K, and L. The compounds are all C35 Annonaceous acetogenins with a mono-tetrahydrofuran ring and four hydroxyls. Their structures were elucidated by spectral methods and chemical modification after isolation via chromatographic techniques and HPLC purification. These three acetogenins demonstrated an antiproliferative against human prostate cancer PC-3 cells.     

Squamocin-O(1) and squamocin-O(2), new adjacent bis-tetrahydrofuran acetogenins from the seeds of Annona squamosa

Two bis-tetrahydrofuran acetogenins, squamocin-O(1) (1) and squamocin-O(2) (2), were isolated from a MeOH extract of seeds of Annona squamosa L. Their structures were determined by spectral means including precursor-ion scanning mass spectral analysis for their aminal derivatives. The configurations at the oxymethine chiral centers were assigned as 12R,15R,16R,19R,20R,23R,24S,28S,36S for 1 and 12S,15R,16R,19R,20R,23R,24S, 28S,36S for 2, based on 1H NMR analysis of their Mosher's ester derivatives and CD data.     

Design, synthesis of symmetrical bivalent mimetics of annonaceous acetogenins and their cytotoxicities

A new series of linear dimeric compounds mimicking naturally occurring annonaceous acetogenins have been synthesized by bivalent analogue design, and their cytotoxicities have been evaluated against the growth of cancer cells by MTT method. Most of these compounds show selective action favored to human cancer cell lines over normal cell lines, and compound 9 with bis-terminal benzoquinone functionality exhibits an IC₅₀ = 0.40 μM against MCF7 cell lines. This work mentions that appropriate conformational constraints might be a useful optimizing tool for this unique class of anticancer compounds.     

Identification of novel bivalent mimetics of annonaceous acetogenins via a scaffold-hopping strategy

A series of novel bivalent mimetics of annonaceous acetogenins have been designed, synthesized, and evaluated. Among these, compound 7 bearing a homopiperazine ring in the middle region exhibited more potent growth inhibitory activity and higher selectivity against cancer cells over normal cells by comparison with AA005. This work indicates that modification of the middle piperazine ring is a useful optimizing tool for the simplified acetogenin mimetics.     

Rollinicin and isorollinicin,cytotoxic acetogenins from Rollinia papilionella

Rollinicin and isorollinicin, two new linear acetogenins bearing bistetrahydrofuran moieties and an α,β-unsaturated-γ-lactone, were isolated from roots of Rollinia papilionella. The structure elucidation of rollinicin and isorollinicin was achieved through interpretation of the ¹H NMR, ¹³C NMR and high resolution mass spectra.     

Lipoxygenase inhibition by novel fatty acid ester from Annona squamosa seeds

Studies on the seeds of Annona squamosa yielded a novel lipoxygenase inhibitor fatty acid ester, (+) - annonlipoxy (1). Compound 1 was screened for its enzyme inhibitory activity against lipoxygenase (E.C.1.14.18.1), exhibiting activity with IC₅₀ 69.05 ± 5.06 μm. Baicalein (IC₅₀ 22.6 ± 0.5 μm) was used as a positive control. Crude extracts of Annona squamosa fruit pulp and seeds were screened for its enzyme inhibitory activity against lipoxygenase and acetylcholinesterase. The crude ethanolic extract of fruit pulp and seeds of Annona squamosa also exhibited lipoxygenase activity with 22.2 and 26.7% inhibition, while the pet.ether extract of seeds of A. squamosa exhibited 52.7% inhibition at a concentration of 40 μg/200 ml. The crude ethanolic extract of seeds of Annona squamosa was also bioassayed for acetylcholinesterase inhibition and it was found inactive.     

Lipoxygenase inhibition by novel fatty acid ester from Annona squamosa seeds

Studies on the seeds of Annona squamosa yielded a novel lipoxygenase inhibitor fatty acid ester, (+) - annonlipoxy (1). Compound 1 was screened for its enzyme inhibitory activity against lipoxygenase (E.C.1.14.18.1), exhibiting activity with IC(50) 69.05 +/- 5.06 microm. Baicalein (IC(50) 22.6 +/- 0.5 microm) was used as a positive control. Crude extracts of Annona squamosa fruit pulp and seeds were screened for its enzyme inhibitory activity against lipoxygenase and acetylcholinesterase. The crude ethanolic extract of fruit pulp and seeds of Annona squamosa also exhibited lipoxygenase activity with 22.2 and 26.7% inhibition, while the pet.ether extract of seeds of A. squamosa exhibited 52.7% inhibition at a concentration of 40 microg/200 ml. The crude ethanolic extract of seeds of Annona squamosa was also bioassayed for acetylcholinesterase inhibition and it was found inactive.     

Ontogenic synchronization of Bephratelloides cubensis,Annona macroprophyllata seeds and acetogenins from Annonaceae

Journal of Plant Research - The seeds of Annona macroprophyllata Donn. Sm. contain idioblasts with toxic acetogenins, including laherradurin and rolliniastatin-2, in relatively high proportions....     

Bullatencin, 4-deoxyasimicin, and the uvariamicins: additional bioactive Annonaceous acetogenins from Annona bullata Rich. (Annonaceae).

Additional bioactive Annonaceous acetogenins have been isolated from the EtOH extract of the bark of Annona bullata Rich. by bioactivity-directed fractionation using lethality to brine shrimp. These acetogenins include bullatencin, a new single tetrahydrofuran acetogenin having a double bond in the hydrocarbon chain; 4-deoxyasimicin, a new adjacent bis-tetrahydrofuran acetogenin; and the uvariamicins, an isomeric mixture of four single tetrahydrofuran acetogenins showed selective cytotoxicities for certain human solid tumor cell lines comparable to or better than adriamycin.     

番荔枝内生真菌Hypoxylon sp.B38的代谢产物研究

从番荔枝内生真菌Hypoxylon sp.B38的固体平板发酵提取物中分离到5个化合物,通过NMR和MS等方法把它们分别被鉴定为Lachnellin D(1)、D ienetriol 9(2)、Lachnellin C(3)、Lachnellin B(4)和Benzo[d][1,3]d ioxol-5-ylm ethanol(5)。