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Literature DB >> 23956472

Waol A, trans-dihydrowaol A, and cis-dihydrowaol A: polyketide-derived γ-lactones from a Volutella species.

Tamam El-Elimat¹, Mario Figueroa, Huzefa A Raja, Audrey F Adcock, David J Kroll, Steven M Swanson, Mansukh C Wani, Cedric J Pearce, Nicholas H Oberlies.

Abstract

An organic extract of a filamentous fungus (MSX 58801), identified as a Volutella sp. (Hypocreales, Ascomycota), displayed moderate cytotoxic activity against NCI-H460 human large cell lung carcinoma. Bioactivity-directed fractionation led to the isolation of three γ-lactones having the furo[3,4-b]pyran-5-one bicyclic ring system [waol A (1), trans-dihydrowaol A (2), and cis-dihydrowaol A (3)]. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configuration of 2 was established via a modified Mosher's ester method. Compounds 1 and 2 were evaluated for cytotoxicity against a human cancer cell panel.

Entities: CellLine Chemical Disease Gene Species

Keywords: Cytotoxicty; Filamentous Fungi; Polyketide; Waol A; γ-Lactone

Year: 2013 PMID： 23956472 PMCID： PMC3743556 DOI： 10.1016/j.tetlet.2013.06.008

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

14 in total

1. The fungi: 1, 2, 3 ... 5.1 million species?

Authors: Meredith Blackwell
Journal: Am J Bot Date: 2011-03-02 Impact factor: 3.844

2. A novel bioactive delta lactone FD-211. Taxonomy, isolation and characterization.

Authors: O Nozawa; T Okazaki; N Sakai; T Komurasaki; K Hanada; S Morimoto; Z X Chen; B M He; K Mizoue
Journal: J Antibiot (Tokyo) Date: 1995-02 Impact factor: 2.649

3. Chemical Diversity of Metabolites from Fungi, Cyanobacteria, and Plants Relative to FDA-Approved Anticancer Agents.

Authors: Tamam El-Elimat; Xiaoli Zhang; David Jarjoura; Franklin J Moy; Jimmy Orjala; A Douglas Kinghorn; Cedric J Pearce; Nicholas H Oberlies
Journal: ACS Med Chem Lett Date: 2012-07-12 Impact factor: 4.345

4. Synthesis of (-)-TAN-2483A. Revision of the structures and syntheses of (+/-)-FD-211 (waol A) and (+/-)-FD-212 (waol B).

Authors: Xiaolei Gao; Masakazu Nakadai; Barry B Snider
Journal: Org Lett Date: 2003-02-20 Impact factor: 6.005

5. Obionin B: An o-pyranonaphthoquinone decaketide from an unidentified fungus (MSX 63619) from the Order Pleosporales.

Authors: Sloan Ayers; Tyler N Graf; Audrey F Adcock; David J Kroll; Qi Shen; Steven M Swanson; Mansukh C Wani; Blaise A Darveaux; Cedric J Pearce; Nicholas H Oberlies
Journal: Tetrahedron Lett Date: 2011-10-05 Impact factor: 2.415

6. Peptaibols from two unidentified fungi of the order Hypocreales with cytotoxic, antibiotic, and anthelmintic activities.

Authors: Sloan Ayers; Brandie M Ehrmann; Audrey F Adcock; David J Kroll; Esperanza J Carcache de Blanco; Qi Shen; Steven M Swanson; Joseph O Falkinham; Mansukh C Wani; Sheila M Mitchell; Cedric J Pearce; Nicholas H Oberlies
Journal: J Pept Sci Date: 2012-06-29 Impact factor: 1.905

7. Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

Authors: Thomas R Hoye; Christopher S Jeffrey; Feng Shao
Journal: Nat Protoc Date: 2007 Impact factor: 13.491

8. Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system. Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212).

Authors: Xiaolei Gao; Barry B Snider
Journal: J Org Chem Date: 2004-08-20 Impact factor: 4.354

9. Cytotoxic xanthone-anthraquinone heterodimers from an unidentified fungus of the order Hypocreales (MSX 17022).

Authors: Sloan Ayers; Tyler N Graf; Audrey F Adcock; David J Kroll; Qi Shen; Steven M Swanson; Susan Matthew; Esperanza J Carcache de Blanco; Mansukh C Wani; Blaise A Darveaux; Cedric J Pearce; Nicholas H Oberlies
Journal: J Antibiot (Tokyo) Date: 2011-11-09 Impact factor: 2.649

10. Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships.

Authors: Sloan Ayers; Tyler N Graf; Audrey F Adcock; David J Kroll; Susan Matthew; Esperanza J Carcache de Blanco; Qi Shen; Steven M Swanson; Mansukh C Wani; Cedric J Pearce; Nicholas H Oberlies
Journal: J Nat Prod Date: 2011-04-22 Impact factor: 4.803

11 in total

1. Comparison of the chemistry and diversity of endophytes isolated from wild-harvested and greenhouse-cultivated yerba mansa (Anemopsis californica).

Authors: Robert O Bussey; Amninder Kaur; Daniel A Todd; Joseph M Egan; Tamam El-Elimat; Tyler N Graf; Huzefa A Raja; Nicholas H Oberlies; Nadja B Cech
Journal: Phytochem Lett Date: 2015-03 Impact factor: 1.679

2. New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii.

Authors: Amninder Kaur; Huzefa A Raja; Blaise A Darveaux; Wei-Lun Chen; Steven M Swanson; Cedric J Pearce; Nicholas H Oberlies
Journal: Magn Reson Chem Date: 2015-06-03 Impact factor: 2.447

3. Chemoinformatic expedition of the chemical space of fungal products.

Authors: Mariana González-Medina; Fernando D Prieto-Martínez; J Jesús Naveja; Oscar Méndez-Lucio; Tamam El-Elimat; Cedric J Pearce; Nicholas H Oberlies; Mario Figueroa; José L Medina-Franco
Journal: Future Med Chem Date: 2016-08-03 Impact factor: 3.808

Waol A, trans-dihydrowaol A, and cis-dihydrowaol A: polyketide-derived γ-lactones from a Volutella species.

1. The fungi: 1, 2, 3 ... 5.1 million species?

2. A novel bioactive delta lactone FD-211. Taxonomy, isolation and characterization.

3. Chemical Diversity of Metabolites from Fungi, Cyanobacteria, and Plants Relative to FDA-Approved Anticancer Agents.

4. Synthesis of (-)-TAN-2483A. Revision of the structures and syntheses of (+/-)-FD-211 (waol A) and (+/-)-FD-212 (waol B).

5. Obionin B: An o-pyranonaphthoquinone decaketide from an unidentified fungus (MSX 63619) from the Order Pleosporales.

6. Peptaibols from two unidentified fungi of the order Hypocreales with cytotoxic, antibiotic, and anthelmintic activities.

7. Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

8. Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system. Revision of the structures of and syntheses of (+/-)-Waol A (FD-211) and (+/-)-Waol B (FD-212).

9. Cytotoxic xanthone-anthraquinone heterodimers from an unidentified fungus of the order Hypocreales (MSX 17022).

10. Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships.

1. Comparison of the chemistry and diversity of endophytes isolated from wild-harvested and greenhouse-cultivated yerba mansa (Anemopsis californica).

2. New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii.

3. Chemoinformatic expedition of the chemical space of fungal products.

4. Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris.

5. qNMR for profiling the production of fungal secondary metabolites.

6. Coumarins, dihydroisocoumarins, a dibenzo-α-pyrone, a meroterpenoid, and a merodrimane from Talaromyces amestolkiae.

7. Biosynthesis of Fluorinated Peptaibols Using a Site-Directed Building Block Incorporation Approach.

8. Evaluation of culture media for the production of secondary metabolites in a natural products screening program.

9. Greensporones: resorcylic acid lactones from an aquatic Halenospora sp.

10. Sorbicillinoid analogs with cytotoxic and selective anti-Aspergillus activities from Scytalidium album.