Publications by authors named "Rachada Haritakun"

11 Publications

  • Page 1 of 1

Alkaloids from the root of Indonesian L.

Nat Prod Res 2021 Feb 8;35(3):481-489. Epub 2019 Jul 8.

School of Chemistry & Molecular Bioscience and Molecular Horizons, University of Wollongong, and Illawarra Health & Medical Research Institute, Wollongong, NSW, Australia.

L. has been used traditionally in Indonesia to treat disease. Phytochemical studies on the alkaloid fractions from the root of L. from Malang-Indonesia resulted in the isolation of an unreported benzylisoquinoline alkaloid (+)-xylopine as well as four known alkaloids (-). The crude methanol extract and alkaloid fractions were tested against K1 and against bacteria (, , , , Methicillin-resistant ) with insignificant activities (MIC > 32 µg/mL). Individual alkaloids were tested against a human suspension cancer cell line (HL-60 leukemia cells) and two human fibroblastic cancer cell lines (A549 lung cancer cells and HepG2 liver cancer cells) in which compound as the most toxic alkaloid with IC values ranging from 20 to 80 µM.
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http://dx.doi.org/10.1080/14786419.2019.1638380DOI Listing
February 2021

Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo.

Beilstein J Org Chem 2015 15;11:481-92. Epub 2015 Apr 15.

School of Chemistry, University of Wollongong, Wollongong, NSW, 2522, Australia.

Diversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2'-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the novel bridged heterocycle 7,8-dihydro-6H-6,8a-epoxyazepino[1,2-a:3,4-b']diindol-14(13H)-one was produced when the olefin of the allylic substrate was terminally disubstituted. Further optimisation also produced viable one-pot syntheses of derivatives of the spiro(indoline-2,9'-pyrido[1,2-a]indol)-3-one (65%) and pyrido[1,2,3-s,t]indolo[1,2-a]azepino[3,4-b]indol-17-one (72%) heterocyclic systems. Ring-closing metathesis of the N,O-diallylic spiro structure and subsequent Claisen rearrangement gave rise to the new (1R,8aS,17aS)-rel-1,2-dihydro-1-vinyl-8H,17H,9H-benz[2',3']pyrrolizino[1',7a':2,3]pyrido[1,2-a]indole-8,17-(2H,9H)-dione heterocyclic system.
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http://dx.doi.org/10.3762/bjoc.11.54DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4419534PMC
May 2015

Bioactive glycosides from the African medicinal plant Boerhavia erecta L.

Nat Prod Res 2015 20;29(20):1954-8. Epub 2015 Feb 20.

a School of Chemistry, University of Wollongong , Northfields Avenue, Wollongong , New South Wales 2522 , Australia.

Phytochemical studies of the previously unexplored stem of Boerhavia erecta from Burkina Faso, resulted in the isolation of an unreported glycoside 4, 2,3-dihydroxypropylbenzoate-3-O-β-[4″-methoxy] glucuronide as well as seven known glycosides (1-3, 5-8). The major isolate 5 and 8 indicated a significant inhibition against HIV integrase (IC50 10 and 22 μg/mL, respectively). The extracts and isolates were also tested for anti-malarial activity, but insignificant activity was observed.
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http://dx.doi.org/10.1080/14786419.2015.1013470DOI Listing
December 2015

Torrubiellone E, an antimalarial N-hydroxypyridone alkaloid from the spider pathogenic fungus Torrubiella longissima BCC 2022.

Nat Prod Commun 2014 May;9(5):627-8

Torrubiellone E (1), a new N-hydroxypyridone alkaloid, was isolated from the spider pathogenic fungus Torrubiella longissima BCC 2022, together with the known compounds, torrubiellones A (2) and B (3), and JBIR-130 (4). Compound 1 exhibited antimalarial activity against Plasmodium falciparum K1 with an IC5 value of 3.2 microg/mL, while it also showed weak cytotoxic activities.
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May 2014

Assessing medium constituents for optimal heterologous production of anhydromevalonolactone in recombinant Aspergillus oryzae.

AMB Express 2014 27;4:52. Epub 2014 Jun 27.

Pilot Plant Development and Training Institute, King Mongkut's University of Technology Thonburi, 49 Soi Thianthale 25, Bangkhunthian-Chaithale Rd., Thakham, Bangkok 10150, Bangkhunthian, Thailand ; School of Bioresources and Technology, King Mongkut's University of Technology Thonburi, 49 Soi Thianthale 25, Bangkhunthian-Chaithale Rd., Thakham, Bangkok 10150, Bangkhunthian, Thailand.

Anhydromevalonolactone (AMVL) is a bioactive natural product that arises from a molecular biology technique using Aspergillus oryzae as a heterologous host. AMVL has been used as a precursor for the synthesis of insect pest control reagents and has numerous applications in the biotechnological and medical industries. In this study, the Plackett-Burman Design and the Central Composite Design, which offer efficient and feasible approaches, were complemented to screen significant parameters and identify the optimal values for maximum AMVL production. The results suggested that sucrose, NaNO3, yeast extract and K2HPO4 were the key factors affecting AMVL production in a complex medium, whereas the major components required for a defined medium were NaNO3, K2HPO4, KH2PO4 and trace elements. These factors were subsequently optimized using the response surface methodology. Under optimal conditions, a maximum AMVL production of 250 mg/L in the complex medium and 200 mg/L in the defined medium was achieved, which represents an increase of approximately 3-4-fold compared to the commonly used malt extract medium.
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http://dx.doi.org/10.1186/s13568-014-0052-9DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4077012PMC
July 2014

Rapid cascade synthesis of poly-heterocyclic architectures from indigo.

J Org Chem 2013 Aug 18;78(15):7639-47. Epub 2013 Jul 18.

School of Chemistry, University of Wollongong, Wollongong, NSW, 2522, Australia.

The base-induced propargylation of the dye indigo results in the rapid and unprecedented one-pot synthesis of highly functionalized representatives of the pyrazino[1,2-a:4,3-a']diindole, pyrido[1,2-a:3,4-b']diindole and benzo[b]indolo[1,2-h]naphthyridine heterocyclic systems, with the last two reflecting the core skeleton of the anticancer/antiplasmodial marine natural products fascaplysin and homofascaplysins and a ring B-homologue, respectively. The polycyclic compounds 6-8, whose structures were confirmed through single-crystal X-ray crystallographic analysis, arise from sequential inter/intramolecular substitution-addition reactions, and in some cases, ring rearrangement reactions. Preliminary studies on controlling the reaction path selectivity, and the potential reaction mechanisms, are also described. Initial biological activity studies with these new heterocyclic derivatives indicated promising in vitro antiplasmodial activity as well as good anticancer activity. The chemistry described is new for the indigo moiety and cascade reactions from this readily available and cheap starting material should be more broadly applicable in the synthesis of additional new heterocyclic systems difficult to access by other means.
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http://dx.doi.org/10.1021/jo401210rDOI Listing
August 2013

Functional expression of a foreign gene in Aspergillus oryzae producing new pyrone compounds.

Fungal Genet Biol 2013 Jan 19;50:55-62. Epub 2012 Nov 19.

Bioresource Research Unit, National Center for Genetic Engineering and Biotechnology, Khlong Nueng, Khlong Luang, Pathum Thani, Thailand.

Fungi from the genus Xylaria produce a wide range of polyketides with diverse structures, which provide important sources for pharmaceutical agents. At least seven polyketide synthase (PKS) genes, including pksmt, were found in Xylaria sp. BCC 1067. The multifunctional enzyme pksmt contains the following catalytic motifs: β-ketosynthase (KS), acyltransferase (AT), dehydratase (DH), methyltransferase (MT), enoylreductase (ER), ketoreductase (KR), and acyl carrier region (ACP). The presence of multiple domains indicated that pksmt was an iterative type I highly-reduced-type PKS gene. To identify the gene function, pksmt was fused with a gene encoding green fluorescent protein (GFP) and introduced into a surrogate host, Aspergillus oryzae, and expressed under the control of a constitutive gpdA promoter. In the transformant, the pksmt gene was functionally expressed and translated as detected by a green fluorescence signal. This transformant produced two new 2-pyrone compounds, 4-(hydroxymethyl)-5,6-dihydro-pyran-2-one and 5-hydroxy-4-methyl-5,6-dihydro-pyran-2-one, as well as a previously identified 4-methyl-5,6-dihydro-pyran-2-one. Our results suggested that pksmt from Xylaria sp. BCC 1067 represents a family of fungal PKSs that can synthesize 2-pyrone-containing compounds.
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http://dx.doi.org/10.1016/j.fgb.2012.10.005DOI Listing
January 2013

Butyrolactones from the fungus Aspergillus terreus BCC 4651.

Chem Pharm Bull (Tokyo) 2010 Nov;58(11):1545-8

National Center for Genetic Engineering and Biotechnology, Thailand.

Two new butenolides, butyrolactones VI (1) and VII (2), were isolated together with six known compounds, butyrolactones I (3), II (4), IV (5), and V (6), aspernolide B (7), and bisdethiodi(methylthio)acetylaranotin (8) from the fungus Aspergillus terreus BCC 4651. Compound 8, exhibiting a minimum inhibitory concentration (MIC) value of 1.56 µg/ml against Mycobacterium tuberculosis H37Ra, proved to be the antimycobacterial principle from the culture of this fungus. On the other hand, butyrolactone V (6) showed antiplasmodial activity against Plasmodium falciparum K1 with an IC₅₀ of 7.9 µg/ml.
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http://dx.doi.org/10.1248/cpb.58.1545DOI Listing
November 2010

An antimycobacterial cyclodepsipeptide from the entomopathogenic fungus Ophiocordyceps communis BCC 16475.

J Nat Prod 2010 Jan;73(1):75-8

National Center for Genetic Engineering and Biotechnology (BIOTEC), 113 Thailand Science Park, Phaholyothin Road, Klong Luang, Pathumthani 12120, Thailand.

A novel cyclodepsipeptide, cordycommunin (1), and two dihydroisocoumarins (2 and 3) were isolated from the insect pathogenic fungus Ophiocordyceps communis BCC 16475. The absolute configurations of the amino acid residues of 1 were addressed by application of Marfey's method. Cordycommunin (1) showed growth inhibition of Mycobacterium tuberculosis H37Ra with an MIC value of 15 microM. This compound also exhibited weak cytotoxicity to KB cells with an IC50 of 45 microM, while it was inactive against BC, NCI-H187, and Vero cell lines at a concentration of 88 microM (50 microg/mL).
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http://dx.doi.org/10.1021/np900520bDOI Listing
January 2010

Isariotins A-D, alkaloids from the insect pathogenic fungus Isaria tenuipes BCC 7831.

J Nat Prod 2007 Sep 7;70(9):1478-80. Epub 2007 Sep 7.

National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Klong Luong, Pathumthani, Thailand.

Isariotins A-D (1- 4), alkaloids possessing a unique bicyclo[3.3.1]nonane ring, were isolated from the insect pathogenic fungus Isaria tenuipes BCC 7831. The structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses.
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http://dx.doi.org/10.1021/np070291qDOI Listing
September 2007

Antimycobacterial and antiplasmodial unsaturated carboxylic acid from the twigs of Scleropyrum wallichianum.

Chem Pharm Bull (Tokyo) 2005 Oct;53(10):1327-9

Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, Thailand.

From the twigs of Scleropyrum wallichianum, a new unsaturated carboxylic acid, scleropyric acid (1), two new esters, beta-sitosteryl-3-O-scleropyrate (2) and stigmasteryl-3-O-scleropyrate (3), and two well-known sterols, beta-sitosterol (4) and stigmasterol (5), were isolated and characterized using spectroscopic methods. Compound 1 exhibited antimycobacterial activity with an MIC value of 25 microg/ml and showed antiplasmodial activity with an IC50 value of 7.2 microg/ml. Compounds 2 and 3 were inactive in both assays.
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http://dx.doi.org/10.1248/cpb.53.1327DOI Listing
October 2005
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