Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar

Du, Yongle; Abedi, Alexander K.; Valenciano, Ana Lisa; Fernández‐Murga, Maria L.; Cassera, Maria B.; Rasamison, Vincent E.; Applequist, Wendy L.; Miller, James S.; Kingston, David G. I.

doi:10.1002/cbdv.201700331

Title: Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar

Abstract

An extract of Malleastrum sp. (Meliaceae) collected in Madagascar by the Madagascar International Cooperative Biodiversity Group was found to have antimalarial activity, with an IC ₅₀ value between 2.5 and 5 μg ml ⁻¹ . After purification by liquid‐liquid partition, chromatography on a Diaion open column, C ₁₈ SPE and C ₁₈ reversed phase HPLC , the new butanolide, malleastrumolide A, was isolated. The structure of malleastrumolide A was determined by mass spectrometry, NMR , and ECD . The double bond position was determined by cross‐metathesis and mass spectrometry. The compound has antiproliferative activity against the A2780 ovarian cancer cell line with an IC ₅₀ value of 17.4 μ m and antiplasmodial activity against the drug‐resistant Dd2 strain of Plasmodium falciparum with an IC ₅₀ value of 2.74 μ m .

Authors:

Du, Yongle ^[1]; Abedi, Alexander K. ^[1]; Valenciano, Ana Lisa ^[2]; Fernández‐Murga, Maria L. ^[3]; Cassera, Maria B. ^[4]; Rasamison, Vincent E. ^[5]; Applequist, Wendy L. ^[6]; Miller, James S. ^[6]; Kingston, David G. I. ^[1]

Department of Chemistry and Virginia Tech Center for Drug Discovery, M/C 0212 Virginia Tech Blacksburg VA 24061 USA
Department of Biochemistry and Molecular Biology Center for Tropical and Emerging Global Diseases (CTEGD) University of Georgia Athens GA 30602 USA
Department of Biochemistry and Virginia Tech Center for Drug Discovery, M/C 0308 Virginia Tech Blacksburg VA 24061 USA
Department of Biochemistry and Molecular Biology Center for Tropical and Emerging Global Diseases (CTEGD) University of Georgia Athens GA 30602 USA, Department of Biochemistry and Virginia Tech Center for Drug Discovery, M/C 0308 Virginia Tech Blacksburg VA 24061 USA
Centre National d'Application des Recherches Pharmaceutiques B.P 702 101 Antananarivo Madagascar
Missouri Botanical Garden P.O. Box 299 St. Louis MO 63166‐0299 USA

Publication Date:: Fri Dec 15 00:00:00 EST 2017

Sponsoring Org.:: USDOE

OSTI Identifier:: 1414776

Grant/Contract Number:: U01 TW00313

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Chemistry & Biodiversity

Additional Journal Information:: Journal Name: Chemistry & Biodiversity Journal Volume: 14 Journal Issue: 12; Journal ID: ISSN 1612-1872

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Country unknown/Code not available

Language:: English

Citation Formats


                    Du, Yongle, Abedi, Alexander K., Valenciano, Ana Lisa, Fernández‐Murga, Maria L., Cassera, Maria B., Rasamison, Vincent E., Applequist, Wendy L., Miller, James S., and Kingston, David G. I. Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar.  Country unknown/Code not available: N. p., 2017. 
Web.  doi:10.1002/cbdv.201700331.

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                    Du, Yongle, Abedi, Alexander K., Valenciano, Ana Lisa, Fernández‐Murga, Maria L., Cassera, Maria B., Rasamison, Vincent E., Applequist, Wendy L., Miller, James S., & Kingston, David G. I. Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar.  Country unknown/Code not available.  https://doi.org/10.1002/cbdv.201700331

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                    Du, Yongle, Abedi, Alexander K., Valenciano, Ana Lisa, Fernández‐Murga, Maria L., Cassera, Maria B., Rasamison, Vincent E., Applequist, Wendy L., Miller, James S., and Kingston, David G. I. Fri .  
"Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar".  Country unknown/Code not available.  https://doi.org/10.1002/cbdv.201700331.

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@article{osti_1414776,

  title        = {Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar},

  author       = {Du, Yongle and Abedi, Alexander K. and Valenciano, Ana Lisa and Fernández‐Murga, Maria L. and Cassera, Maria B. and Rasamison, Vincent E. and Applequist, Wendy L. and Miller, James S. and Kingston, David G. I.},

  abstractNote = {An extract of Malleastrum sp. (Meliaceae) collected in Madagascar by the Madagascar International Cooperative Biodiversity Group was found to have antimalarial activity, with an IC 50 value between 2.5 and 5 μg ml −1 . After purification by liquid‐liquid partition, chromatography on a Diaion open column, C 18 SPE and C 18 reversed phase HPLC , the new butanolide, malleastrumolide A, was isolated. The structure of malleastrumolide A was determined by mass spectrometry, NMR , and ECD . The double bond position was determined by cross‐metathesis and mass spectrometry. The compound has antiproliferative activity against the A2780 ovarian cancer cell line with an IC 50 value of 17.4 μ m and antiplasmodial activity against the drug‐resistant Dd2 strain of Plasmodium falciparum with an IC 50 value of 2.74 μ m .},

  doi          = {10.1002/cbdv.201700331},

  journal      = {Chemistry & Biodiversity},

  number       = 12,

  volume       = 14,

  place        = {Country unknown/Code not available},

  year         = {Fri Dec 15 00:00:00 EST 2017},

  month        = {Fri Dec 15 00:00:00 EST 2017}

}

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Works referenced in this record:

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Antiplasmodial Sesquiterpenoid Lactones from Trichospira verticillata : Structure Elucidation by Spectroscopic Methods and Comparison of Experimental and Calculated ECD Data
journal, May 2017

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Title: Isolation of the New Antiplasmodial Butanolide, Malleastrumolide A, from Malleastrum sp. (Meliaceae) from Madagascar

Abstract

Citation Formats

Spread of Artemisinin Resistance in Plasmodium falciparum Malaria journal, July 2014

Artemisinin and its derivatives: an important new class of antimalarial agents journal, May 2001

Novel, Rapid, and Inexpensive Cell-Based Quantification of Antimalarial Drug Efficacy journal, April 2004

Optical activity of lactones and lactams—I journal, January 1983

Four Diphenylpropanes and a Cycloheptadibenzofuran from Bussea sakalava from the Madagascar Dry Forest(1) journal, November 2010

Plant-Derived Antimalarial Agents: New Leads and Efficient Phytomedicines. Part II. Non-Alkaloidal Natural Products journal, August 2009

Simple Determination of Double-Bond Positions in Long-Chain Olefins by Cross-Metathesis journal, June 2011

Cytotoxic sesquiterpenoids from Winteraceae of Caledonian rainforest journal, March 2009

Antiproliferative Limonoids of a Malleastrum sp. from the Madagascar Rainforest † , (1) journal, March 2008

13 C NMR-Based Empirical Rules to Determine the Configuration of Fatty Acid Butanolides. Novel γ-Dilactones from Pterogorgia spp journal, October 2006

Artemisinin, a miracle of traditional Chinese medicine journal, January 2015

Amphiasterins: a new family of cytotoxic metabolites from the marine sponge Plakortis quasiamphiaster journal, January 2001

Antiplasmodial Sesquiterpenoid Lactones from Trichospira verticillata : Structure Elucidation by Spectroscopic Methods and Comparison of Experimental and Calculated ECD Data journal, May 2017

Circular dichroism in lactones journal, January 1968

Antiproliferative Xanthones of Terminalia calcicola from the Madagascar Rain Forest 1 journal, April 2007

Spread of Artemisinin Resistance in Plasmodium falciparum Malaria
journal, July 2014

Artemisinin and its derivatives: an important new class of antimalarial agents
journal, May 2001

Novel, Rapid, and Inexpensive Cell-Based Quantification of Antimalarial Drug Efficacy
journal, April 2004

Optical activity of lactones and lactams—I
journal, January 1983

Four Diphenylpropanes and a Cycloheptadibenzofuran from Bussea sakalava from the Madagascar Dry Forest(1)
journal, November 2010

Plant-Derived Antimalarial Agents: New Leads and Efficient Phytomedicines. Part II. Non-Alkaloidal Natural Products
journal, August 2009

Simple Determination of Double-Bond Positions in Long-Chain Olefins by Cross-Metathesis
journal, June 2011

Cytotoxic sesquiterpenoids from Winteraceae of Caledonian rainforest
journal, March 2009

Antiproliferative Limonoids of a Malleastrum sp. from the Madagascar Rainforest ^† ^, (1)
journal, March 2008

¹³ C NMR-Based Empirical Rules to Determine the Configuration of Fatty Acid Butanolides. Novel γ-Dilactones from Pterogorgia spp
journal, October 2006

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journal, January 2015

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Antiplasmodial Sesquiterpenoid Lactones from Trichospira verticillata : Structure Elucidation by Spectroscopic Methods and Comparison of Experimental and Calculated ECD Data
journal, May 2017

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journal, January 1968

Antiproliferative Xanthones of Terminalia calcicola from the Madagascar Rain Forest ¹
journal, April 2007