Recent progress on the total synthesis of acetogenins from Annonaceae (Q24642026)

Europe PubMed Central

title

Recent progress on the total synthesis of acetogenins from Annonaceae (English)

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Annonaceae

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Nianguang Li

1

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Zhihao Shi

2

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Yuping Tang

3

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Jianwei Chen

4

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Xiang Li

Beilstein Journal of Organic Chemistry

5

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language of work or name

English

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publication date

2008

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published in

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volume

4

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page(s)

48

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copyright license

Creative Commons Attribution 2.0 Generic

start time

5 December 2008

1 reference

April 2022 Public Data File from Crossref

copyright status

copyrighted

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cites work

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27 September 2017

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Total synthesis of (-)-mucocin

27 September 2017

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Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane

27 September 2017

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Total synthesis of murisolins and evaluation of tumor-growth inhibitory activity

27 September 2017

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Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action

27 September 2017

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Total synthesis and preliminary biological evaluation of cis-solamin isomers

27 September 2017

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Fluorous mixture synthesis of stereoisomer libraries: total syntheses of (+)-murisolin and fifteen diastereoisomers

27 September 2017

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

27 September 2017

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Total synthesis and structure confirmation of the annonaceous acetogenins 30(S)-hydroxybullatacin, uvarigrandin a, and 5(R)-uvarigrandin a (narumicin I?).

27 September 2017

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A modular synthesis of annonaceous acetogenins

27 September 2017

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Total Synthesis of the Cytotoxic Threo, Trans, Erythro, Cis, Threo Annonaceous Acetogenin Trilobin

27 September 2017

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Total Synthesis of the Nonadjacent Bis-Tetrahydrofuran Annonaceous Acetogenin Squamostatin-D.

27 September 2017

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Total Synthesis of Uvaricin

27 September 2017

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Toward Chemical Libraries of Annonaceous Acetogenins. Total Synthesis of Trilobacin

27 September 2017

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Formal synthesis of uvaricin via palladium-mediated double cyclization

27 September 2017

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Total synthesis of the cytotoxic threo, trans, threo, trans, threo annonaceous acetogenin asimin and its C-10 epimer: unambiguous confirmation of absolute stereochemistry

27 September 2017

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Annonaceous acetogenins: recent progress

27 September 2017

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https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Syntheses and cytotoxicities of four stereoisomers of muricatacin from D-glucose

27 September 2017

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Isolation of new bioactive annonaceous acetogenins from Rollinia mucosa guided by liquid chromatography/mass spectrometry

27 September 2017

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Novel mono-tetrahydrofuran ring acetogenins, from the bark of Annona squamosa, showing cytotoxic selectivities for the human pancreatic carcinoma cell line, PACA-2.

27 September 2017

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https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteus.

27 September 2017

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Recent advances in Annonaceous acetogenins

27 September 2017

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https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Acetogenins from Annonaceae, inhibitors of mitochondrial complex I.

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Squamotacin: an annonaceous acetogenin with cytotoxic selectivity for the human prostate tumor cell line (PC-3).

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

New bioactive adjacent bis-THF annonaceous acetogenins from Annona bullata

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Mitochondria in chemotherapy-induced apoptosis: a prospective novel target of cancer therapy (review).

27 September 2017

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Longimicins A-D: novel bioactive acetogenins from Asimina longifolia (annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins.

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae).

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Acaterin, a novel inhibitor of acyl-CoA: cholesterol acyltransferase produced by Pseudomonas sp. A92.

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.

30 May 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Divergence en route to nonclassical annonaceous acetogenins. Synthesis of pyranicin and pyragonicin.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Synthesis of the proposed structure of mucoxin via regio- and stereoselective tetrahydrofuran ring-forming strategies

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Enantioselective total synthesis of (+)-gigantecin: exploiting the asymmetric glycolate aldol reaction

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

New strategy for the construction of a monotetrahydrofuran ring in Annonaceous acetogenin based on a ruthenium ring-closing metathesis: application to the synthesis of Solamin

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

First total synthesis of murisolin

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Synthesis of (--)-Muricatacin via alpha- and alpha'-C-H bond functionalization of tetrahydrofuran

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

A novel constituent from Rollinia mucosa, rollicosin, and a new approach to develop annonaceous acetogenins as potential antitumor agents

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Total synthesis of an antitumor agent, mucocin, based on the "chiron approach".

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

The total synthesis of the annonaceous acetogenin, muricatetrocin C.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Isolation of Montecristin, a Key Metabolite in Biogenesis of Acetogenins from Annona muricata and Its Structure Elucidation by Using Tandem Mass Spectrometry

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Total synthesis of asimicin and bullatacin

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

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

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

cis-monotetrahydrofuran acetogenins from the roots of annona muricata1

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

The Annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Asimilobin and cis- and trans-murisolinones, novel bioactive Annonaceous acetogenins from the seeds of Asimina triloba.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes.

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Gigantecin: a novel antimitotic and cytotoxic acetogenin, with nonadjacent tetrahydrofuran rings, from Goniothalamus giganteus (Annonaceae).

28 November 2018

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=2633664

Applying Mosher's method to acetogenins bearing vicinal diols. The absolute configurations of muricatetrocin C and rollidecins A and B, new bioactive acetogenins from Rollinia mucosa

28 November 2018

1 reference

12 December 2020

Synthesis of pyragonicin

1 reference

12 December 2020

Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba

1 reference

12 December 2020

The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins

1 reference

12 December 2020

Total synthesis of the proposed structure for pyragonicin

1 reference

12 December 2020

Brine shrimp: a convenient general bioassay for active plant constituents

1 reference

12 December 2020

Parallel, Stereoselective Syntheses of both Enantiomers of Muricatacin and Their Sulfur and Nitrogen Relatives Using the Silyloxy Diene-Based Methodology

1 reference

12 December 2020

Unexpected stereochemistry in the lithium salt catalyzed ring expansion of nonracemic oxaspiropentanes. formal syntheses of (-)-(4R,5R)-muricatacin and the pheromone (R)-japonilure

1 reference

12 December 2020

Total synthesis of a new cytotoxic acetogenin, jimenezin, and the revised structure

1 reference

12 December 2020

Total synthesis of jimenezin via an intramolecular allylboration

1 reference

12 December 2020

[The Relative Configuration of Acetogenins Isolated from Annona squamosa: Annonin I (Squamocin) and Annonin VI]

1 reference

12 December 2020

Total synthesis of gigantetrocin A

1 reference

12 December 2020

[Annonacins and Annonastatin from Annona squamosa]

1 reference

12 December 2020

Total synthesis of cis-solamin

1 reference

12 December 2020

Stereoselective total synthesis of mucocin, an antitumor agent

1 reference

12 December 2020

Tonkinelin: a novel annonaceous acetogenin from Uvaria tonkinensis

1 reference

12 December 2020

Synthesis ofcis-Solamin Using a Permanganate-Mediated Oxidative Cyclization

1 reference

12 December 2020

Sequencing of three-component olefin metatheses: total synthesis of either (+)-gigantecin or (+)-14-deoxy-9-oxygigantecin

1 reference

12 December 2020

Squamocin, a new cytotoxic bis-tetrahydrofuran containing acetogenin from Annona squamosa

1 reference

12 December 2020

Asymmetric total synthesis of rollicosin

1 reference

12 December 2020

10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I

1 reference

12 December 2020

Longifolicin, longicoricin, and gigantetroneninone, three novel bioactive mono-tetrahydrofuran annonaceous acetogenins from Asimina longifolia (Annonaceae)

1 reference

12 December 2020

Tonkinecin, a novel bioactive annonaceous acetogenin from Uvaria tonkinesis

1 reference

12 December 2020

Synthesis of murisolin, (15R, 16R, 19R, 20S)-murisolin A, and (15R, 16R, 19S, 20S)-16,19-cis-murisolin and their inhibitory action with bovine heart mitochondrial complex I

1 reference

12 December 2020

Total synthesis of (+)-cis-sylvaticin: double oxidative cyclization reactions catalyzed by osmium

1 reference

12 December 2020

Convergent synthesis of pyragonicin

1 reference

12 December 2020

Total synthesis and structural confirmation of (+)-longicin

1 reference

12 December 2020

Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia

1 reference

12 December 2020

First total synthesis of mosin B

1 reference

12 December 2020

Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I

1 reference

12 December 2020

Total synthesis of cis-solamin: exploiting the RuO4-catalyzed oxidative cyclization of dienes

1 reference

12 December 2020

Muconin and Mucoxin: Additional Nonclassical Bioactive Acetogenins from Rollinia mucosa

1 reference

12 December 2020

Total synthesis of (+)-muconin

1 reference

12 December 2020

Total synthesis of pyranicin

1 reference

12 December 2020

Total Synthesis of a Cytotoxic Acetogenin, Pyranicin

1 reference

12 December 2020

Annonacin, a novel, biologically active polyketide from Annona densicoma

1 reference

12 December 2020

Concise total synthesis of (-)-muricatacin by tandem ring-closing/cross metathesis

1 reference

12 December 2020

Synthesis of (4R,12S,15S,16S,19R,20R,34S)-Muricatetrocin and (4R,12R,15S,16S,19R,20R,34S)-Muricatetrocin, Two Potent Inhibitors of Mitochondrial Complex I

1 reference

7 January 2021

Muricatetrocins A and B and Gigantetrocin B: Three New Cytotoxic Monotetrahydrofuran-Ring Acetogenins from Annona muricata

1 reference

7 January 2021

Solamin, a cytotoxic mono-tetrahydrofuranic γ-lactone acetogenin from Annona muricata seeds

1 reference

7 January 2021

The absolute configuration of trilobacin and trilobin, a novel highly potent acetogenin from the stem bark of Asimina triloba (Annonaceae)

1 reference

7 January 2021

16,19-cis-murisolin and murisolin a, two novel bioactive mono-tetrahydrofuran annonaceous acetogenins from Asimina triloba seeds

1 reference

7 January 2021

Natural acetogenins from annonaceae, synthesis and mechanisms of action

1 reference

7 January 2021

Unusual bioactive annonaceous acetogenins from Goniothalamus giganteus

1 reference

7 January 2021

New method for the determination of the absolute stereochemistry in antitumoral annonaceous acetogenins

1 reference

7 January 2021

Goniocin from Goniothalamus giganteus: The first tri-THF annonaceous acetogenin

1 reference

7 January 2021

Muricatacin: A simple biologically active acetogenin derivative from the seeds of annona muricata (annonaceae)

1 reference

7 January 2021

Rollimembrin, a novel acetogenin inhibitor of mammalian mitochondrial complex I

1 reference

7 January 2021

Mucocin: A New Annonaceous Acetogenin Bearing a Tetrahydropyran Ring

1 reference

7 January 2021

Absolute Stereochemistry of (+)-Gigantecin from Annona coriacea (Annonaceae)

1 reference

7 January 2021

Constituents of Eremocarpus setigerus (Euphorbiaceae). A new diterpene, eremone, and hautriwaic acid

1 reference

7 January 2021

Jimenezin, a Novel Annonaceous Acetogenin from the Seeds ofRollinia mucosaContaining Adjacent Tetrahydrofuran−Tetrahydropyran Ring Systems†,1

1 reference

7 January 2021

Isolation and structure of rolliniastatin 1 from the South American tree Rollinia mucosa

1 reference

7 January 2021

Parvifloracin and parviflorin: cytotoxic bistetrahydrofuran acetogenins with 35 carbons from Asimina parviflora (Annonaceae)

1 reference

7 January 2021

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

1 reference

7 January 2021

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

1 reference

7 January 2021

Squamostanal-A, Apparently Derived from Tetrahydrofuranic Acetogenin, fromAnnona squamosa

1 reference

7 January 2021

Murisolin: A New Cytotoxic Mono-tetrahydrofuran-g-lactone from Annona muricata

1 reference

7 January 2021

Gigantetrocin and Gigantriocin: Two Novel Bioactive Annonaceous Acetogenins from Goniothalamus giganteus

1 reference

7 January 2021

Giganenin, a Highly Potent Monotetrahydrofuran Acetogenin and 4-Deoxygigantecin from Goniothalamus giganteus

1 reference

7 January 2021

Bullacin: A New Cytotoxic Annonaceous Acetogenin from Annona bullata

1 reference

7 January 2021

Bullatin and Bullanin: Two Novel, Highly Cytotoxic Acetogenins from Asimina triloba

1 reference

7 January 2021

Goniodenin, a New Bioactive Annonaceous Acetogenin from Goniothalamus giganteus and Its Conversion to Tri-THF Acetogenins

1 reference

7 January 2021

Absolute Stereochemistries of Sylvaticin and 12,15-cis-Sylvaticin, Bioactive C-20,23-cis Non-adjacent Bistetrahydrofuran Annonaceous Acetogenins, from Rollinia mucosa

1 reference

7 January 2021

Asimicin, a New Cytotoxic and Pesticidal Acetogenin from the Pawpaw, Asimina triloba (Annonaceae)

1 reference

7 January 2021

Acaterin, a novel inhibitor of acyl-CoA: Cholesterol acyltransferase produced by Pseudomonas sp. A92.

1 reference

7 January 2021

Identifiers

DOI

10.3762/BJOC.4.48

1 reference

1 reference

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PubMed publication ID

19190742

1 reference