Cheritamine,A New N-Fatty Acyl Tryptamine and Other Constituents from the Stems of Annona cherimola

A new N-fatty acyl tryptamine, cheritamine ( 30 ), along with thirty-two compounds including nineteen benzenoids, p-hydroxybenzadehyde ( 1 ), p-hydroxybenzoic acid ( 2 ), methylparabene ( 3 ), 3-chlorobenzoic acid ( 4 ), vanillin ( 5 ), isovanillin ( 6 ), vanillic acid ( 7 ), isovanillic acid ( 8 ), methyl vanillate ( 9 ), methyl isovanillate ( 10 ), syringaldehyde ( 11 ), syringic acid ( 12 ), 3,4,5-trimethoxybenzoic acid ( 13 ), trans-methyl p-coumarate ( 14 ), ferulic acid ( 15 ), p-dihydrocoumaric acid ( 16 ), 3-(4-hydroxy-3,5-dimethoxyphenyl)-1,2-propanediol ( 17 ), 3,4,5 -trimethoxyphenyl-β-D-glucopyranoside ( 18 ) and thalictoside ( 19 ); one p-quinone, 2,6-dimethoxy-p-quinone ( 20 ); one purine, uridine ( 21 ); eight alkaloids, nicotinic acid ( 22 ), thalifoline ( 23 ), doryphornine ( 24 ), (–)-norstephalagine ( 25 ), (-)-romucosine ( 26 ), (+)-pronuciferine ( 27 ), (+)-norisocorydine ( 28 ) and oxoasimilobine (29) and three steroids, β-sitosterol-D-glucoside ( 31 ), stigmasterol-D-glucoside ( 32 ) and 6′-(β-sitosteryl-3-O-β-glucopyranosidyl)hexadecanoate ( 33 ), are isolated from the stems of Annona cherimola. These compounds were characterized and identified by physical and spectral evidence.     

Lignans and Kauranes from the Stems of Annona cherimola

Four lignans and six kauranes, (+)-epi-syringaresinol ( 1 ), annocherin A (16β-hydroxy-17,19-diacetoxy-ent-kaurane) ( 2 ), (+)-syringaresinol ( 3 ), (+)-dia-syringaresinol ( 4 ), liriodendrin[(+)-syringaresinol-di-O-β-D-glucopyranoside] ( 5 ), 16α-hydro-17-acetoxy-ent-kauran-19-oic acid ( 6 ), 16β-hydro-17-hydroxy-ent-kauran-19-al ( 7 ), 16α-hydro-17-hydroxy-ent-kauran-19-al ( 8 ), 16β-hydro-17-hydroxy-ent-kauran-19-oic acid ( 9 ) and 16α-hydro-17-hydroxy-ent-kauran-19-oic acid ( 10 ) were isolated from the stems of Annona cherimola. Among them, 1 is obtained for the first time from natural sources and 2 is a new compound. The structures of these compounds were characterized and identified by spectral analyses.     

Chemical Constituents from Annona Glabra

A new kaurane diterpenoid, annoglabasin G (16α‐hydro‐19‐acetoxy‐ent‐kauran‐17‐al) ( 1 ), along with 27 compounds including 18 kaurane diterpenoids, 16β‐hydro‐ent‐kauran‐17‐oic acid ( 2 ), 16α‐hydro‐ent‐kauran‐17‐oic acid ( 3 ), 19‐nor‐ent‐kauran‐4α‐ol‐17‐oic acid ( 4 ), 16α‐hydro‐19‐ol‐ent‐kauran‐17‐oic acid ( 5 ), ent‐kaur‐16‐en‐19‐oic acid ( 6 ), 16α‐hydroxy‐ent‐kauran‐19‐oic acid ( 7 ), 16α,17‐dihydroxy‐ent‐kauran‐19‐oic acid ( 8 ), 16β,17‐dihydroxy‐ent‐kauran‐19‐oic acid ( 9 ), 16α‐hydro‐ent‐kauran‐17,19‐dioic acid ( 10 ), 16β‐hydroxy‐17‐acetoxy‐ent‐kauran‐19‐oic acid ( 11 ), 16β‐hydro‐17‐hydroxy‐ent‐kauran‐19‐al ( 12 ), 16α‐hydro‐17‐hydroxy‐ent‐kauran‐19‐al ( 13 ), 16β,17‐dihydroxy‐ent‐kauran‐19‐al ( 14 ), 16α‐hydro‐19‐al‐ent‐kauran‐17‐oic acid ( 15 ), 16α‐hydro‐17‐acetoxy‐ent‐kauran‐19‐al ( 16 ), 16α‐hydro‐19‐acetoxy‐ent‐kauran‐17‐oic acid ( 17 ), ent‐kaur‐15‐en‐19‐oic acid ( 18 ) and ent‐kaur‐15‐en‐17‐ol‐19‐oic acid ( 19 ); four acetogenins, annomontacin ( 20 ), annonacin ( 21 ), isoannonacinone ( 22 ) and squamocin ( 23 ); four steroids, β‐sitosterol ( 24 ), stigmasterol ( 25 ), β‐sitosteryl‐D‐glucoside ( 26 ) and stigmasteryl‐D‐glucoside ( 27 ) and one oxoaporphine, liriodenine ( 28 ), were isolated from the fresh fruits of Annona glabra. These compounds were characterized and identified by physical and spectral evidence.     

Antihyperglycemic and Antilipidemic Properties of a Tea Infusion of the Leaves from Annona cherimola Miller on Streptozocin-Induced Type 2 Diabetic Mice

The antihyperglycemic and antilipidemic effects of the tea infusion extracts of leaves from Annona cherimola Miller (IELAc-0.5, IELAc-1.5, and IELAc-3.0) were evaluated on normoglycemic (NG) and streptozocin-induced diabetic (STID) mice. In the acute test, IELAc-1.5 at 300 mg/kg bodyweight (bw) exhibited antihyperglycemic activity on STID mice since the first hour of treatment. Then, its antidiabetic potential was analyzed in a subchronic evaluation. IELAc-1.5 was able to reduce the blood glucose level, glycated hemoglobin (HbA1c), cholesterol (CHO), and triglycerides (TG); high-density lipoprotein (HDL) showed an increase at the end of treatment. IELAc-1.5 did not modify the urine profile at the end of the evaluation, and neither toxicity nor macroscopic organ damage were observed in acute and subchronic assays. In addition, a major flavonol glycoside present in the tea infusion extracts was identified using high-performance liquid chromatography with diode array detection (HPLC-DAD). The analysis of the tea infusion extracts by HPLC revealed that rutin was the major component. This study supports the use of tea infusions from Annona cherimola for the treatment of diabetes and suggests that rutin could be responsible, at least in part, for their antidiabetic properties.     

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.     

Cytotoxic Diterpenoids from the Stem Bark of Annona squamosa L.

Three new ent‐kaurane diterpenoids, (4α)‐19‐nor‐ent‐kaurane‐4,16,17‐triol ( 1 ), (4α,16α)‐17‐(acetyloxy)‐19‐nor‐ent‐kaurane‐4,16‐diol ( 2 ), and 17‐hydroxy‐ent‐kaur‐15‐en‐19‐al ( 3 ), together with 11 known compounds, were isolated from the stem bark of Annona squamosa L. The structures of 1 – 3 were identified by analysis of their spectroscopic data. All compounds were evaluated for cytotoxic activity against human lung cancer (95‐D) and ovarian cancer (A2780) cell lines, and compounds 3, 5, 7, 11 – 14 exhibited promising antiproliferative activities with IC₅₀ values ranging from 0.38 to 34.66 μM .     

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…     

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。     

Sequence and solution structure of cherimolacyclopeptides A and B, novel cyclooctapeptides from the seeds of Annona cherimola

Two new cyclooctapeptides, cherimolacyclopeptide A, cyclo(Pro¹-Gln²-Thr³-Gly⁴-Met⁵-Leu⁶-Pro⁷-Ile⁸-) (1) and the related cherimolacyclopeptide B, cyclo(Pro¹-Gln²-Thr³-Gly⁴-Mso⁵-Leu⁶-Pro⁷-Ile⁸-) (2), have been isolated from the methanol extract of the seeds of Annona cherimola Miller. The sequences were elucidated on the basis of the MS/MS fragmentation, using a Q-TOF mass spectrometer equipped with an ESI source, chemical degradation and extensive 2D-heteronuclear NMR. The three-dimensional solution structure of cherimolacyclopeptide A (1) determined by ¹H NMR data and molecular modelling is characterised by the presence of two β turns and a new type of β-bulge.     

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。     

The Constituents of Cananga odorata

Sixteen compounds, (+)-ushinsunine-β-N-oxide ( 1 ), cleistopholine ( 2 ), liriodenine ( 3 ), (-)-anonaine ( 4 ), (+)-nornuciferine ( 5 ), (+)-N-acetylnornuciferine ( 6 ), (-)-ushinsunine ( 7 ), (-)-norushinsunine ( 8 ), (-)-asimilobine ( 9 ), (+)-reticuline ( 10 ), N-trans-feruloyltyramine ( 11 ), β-sitosterol (12) and stigmasterol ( 13 ), lyscamine ( 14 ), (-)-anaxagoreine ( 15 ) and trans-cinnamic acid ( 16 ) were isolated from the methanolic extract of the Cananga odorata. Among them, 1 is a new stereoisomer of ushinsunine-β-N-oxide. The structures of these compounds were established by means of spectral experiments.     

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.     

A New Diterpenoid Dimer from Annona Glabra

A new diterpenoid dimer annonebinide A has been isolated from the stems of Annona glabra.Its structure was determined to be ent-16α-hydroxykauran-17-yl ent-16β-kauran-17-oate on the basis of spectroscopic and chemical evidence.     

Constituents from the Roots of Semiaquilegia adoxoides

In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides （DC） Makino （Chinese name Tiankuizi）, the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1[（3,4-dihydroxyphenyl）methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A （1）, and a new ester, 3-（4＇-hydroxyphenyl）-2-propenoic acid （4＂-carboxyl）-phenyl ester （2）, and four cyano-containing compounds, （Z）-6a-（β-D-glucosyloxy）-4a,5a-dihydroxy-2-cyclohexene-△^1,a-acetonitrile （3）, （L0-6α-（β-D-glucosyloxy）-4α-hydroxy-2-cyclohexene-△^1,α-acetonitrile （4）, lithospermoside （5）, ehretioside B （6）, as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.     

Cyclic peptides from the seeds of Annona glauca and A. cherimola

From the seeds of Annona glauca and A. cherimola, two novel cyclic peptides, glaucacyclopeptide B and cherimolacyclopeptide G, have been isolated, respectively. Their structures were elucidated by chemical and spectral methods.     

A New ent‐Kaurane Diterpene from Stems of Alibertia macrophylla K. Schum. (Rubiaceae)

Phytochemical investigations of the stems of a specimen of Alibertia macrophylla led to the isolation and characterization of the new diterpene ent‐kaurane‐2β,3α,16α‐triol ( 1 ), along with triterpenes 2 – 8 , iridoids 9 – 12 , and phenolic acids 13 – 15 . The structure of 1 was established based on spectroscopic studies (¹H‐ and ¹³C‐NMR, IR, and HR‐ESI‐MS). This is the first report of the isolation of a diterpene from the Alibertia genus in Rubiaceae.     

Alkaloids from the Stems of Glycosmis pentaphylla

A new simple carbazole alkaloid, 4‐(7‐hydroxy‐3‐methoxy‐6‐methyl‐9H‐carbazol‐4‐yl)but‐3‐en‐2‐one ( 1 ), and two new dimeric carbazole alkaloids, bisglybomine B ( 2 ) and biscarbalexine A ( 3 ), together with seven known alkaloids, were isolated from the stems of Glycosmis pentaphylla. Their structures were elucidated by spectroscopic methods, especially 2D‐NMR techniques.     

Annosqualine: a Novel Alkaloid from the Stems of Annona squamosa

Annosqualine (=(10′bR)‐1′,5′,6′,10′b‐tetrahydro‐9′‐hydroxy‐7′,8′‐dimethoxyspiro[cyclohexa‐2,5‐diene‐1,2′‐pyrrolo[2,1‐a]isoquinoline]‐3′,4‐dione; 1 ), a novel alkaloid with an unprecedented skeleton, and a new amide, dihydrosinapoyltyramine (=3‐(4‐hydroxy‐3,5‐dimethoxyphenyl)‐N‐[2‐(4‐hydroxyphenyl)ethyl]propanamide; 2 ), were isolated from the stems of Annona squamosa L., together with six known alkaloids. The structures of all compounds were elucidated spectroscopically by means of optical rotation, ¹H‐, ¹³C‐, and 2D‐NMR, and by EI‐MS, or by comparison with the spectral data of authentic samples. A possible biogenetical pathway towards annosqualine ( 1 ) is proposed.     

Chemical Constituents from the Stems of Mahonia Japonica

A new dihydroberberine alkaloid, 7,8‐dihydro‐8‐methoxyberberine ( 1 ), along with six known compounds including two dihydroberberine alkaloids, 7,8‐dihydro‐8‐hydroxyberberine ( 2 ) and oxyberberine ( 3 ) and four protoberberine alkaloids, berberine ( 4 ), palmatine ( 5 ), jatrorrhizine ( 6 ) and columbamine ( 7 ), were isolated from the stems of Mahonia japonica. These compounds were characterized and identified by physical and spectral evidence.     

Polyphenols from Vitis vinifera Seeds

The chemical composition of polyphenols from grape seeds was studied. It has been found that they contain four catechins and two proanthocyanidins. The probable structure of the proanthocyanidins was proposed on the basis of physicochemical investigations.