Publications by authors named "Sanit Thongnest"

14 Publications

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Diterpenoids with Aromatase Inhibitory Activity from the Rhizomes of .

J Nat Prod 2021 Jun 10. Epub 2021 Jun 10.

Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.

Investigation of bioactive compounds from the rhizomes of led to the isolation and characterization of ten new diterpenoids, namely, five 12,13--diterpenoids named elegansins A-E (-) and five new abietanes, elegansols A-E (-), together with seven known diterpenoids (-). The structure elucidation of the new compounds was achieved by HRESIMS, NMR, and ECD spectroscopic analysis. Compounds (-) are the first examples of 12,13--diterpenoid-type compounds representing a decalin fused dihydropyran skeleton. Plausible biosynthetic pathways for compounds - are proposed. Aromatase inhibitory activities of all compounds were evaluated, and abieta-8,11,13-trien-11-ol () was found to be the most potent aromatase inhibitor with an IC value of 3.7 μM.
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http://dx.doi.org/10.1021/acs.jnatprod.0c01292DOI Listing
June 2021

Uvarmicranones A and B, two new benzoquinones and cytotoxic constituents from the stems of (A. DC.) Hook. f. & Thomson.

Nat Prod Res 2020 Sep 22:1-10. Epub 2020 Sep 22.

Laboratory of Natural Products, Chulabhorn Research Institute, Bangkok, Thailand.

Two novel benzoquinones, uvarmicranones A () and B (), along with 15 known compounds (-) were isolated from the stems of (Annonaceae). Their structures were elucidated by analyses of NMR and high-resolution mass data. A plausible biosynthetic pathway of uvarmicranone A () Diels-Alder cycloaddition reaction was also proposed. Some isolated compounds were evaluated for their cytotoxic activities. Compounds , , and showed moderate cytotoxic effects against -cell acute lymphoblastic cells (MOLT-3), with IC values of 7.83 ± 0.83, 6.53 ± 1.01, and 4.20 ± 0.29 μM, respectively. Additionally, compound exhibited moderate cytotoxicity against cervical carcinoma cells (HeLa) with an IC value of 7.00 ± 3.15 μM.
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http://dx.doi.org/10.1080/14786419.2020.1824221DOI Listing
September 2020

An anticonvulsive drug, valproic acid (valproate), has effects on the biosynthesis of fatty acids and polyketides in microorganisms.

Sci Rep 2020 06 9;10(1):9300. Epub 2020 Jun 9.

Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Laksi, Bangkok, 10210, Thailand.

Valproic acid or valproate (VPA) is an anticonvulsive drug used for treatments of epilepsy, bipolar disorder, and migraine headaches. VPA is also an epigenetic modulator, inhibiting histone deacetylase, and it has been subjected to clinical study for cancer treatment. During the investigation of VPA on a metabolite profile in a fungus, we found that VPA has significant effects on the production of some fatty acids. Further exploration of VPA on fatty acid profiles of microorganisms, fungi, yeast, and bacteria, as well as representative gut microbiome, revealed that VPA could enhance or reduce the production of some fatty acids. VPA was found to induce the production of trans-9-elaidic acid, a fatty acid that was previously reported to have cellular effects in human macrophages. VPA could also inhibit the production of some polyketides produced by a model fungus. The present work suggests that the induction or inhibition of fatty acid biosynthesis by VPA (100 µM) in gut microbiome could give effects to patients treated with VPA because high doses of VPA oral administration (up to 600 mg to 900 mg) are used by patients; the concentration of VPA in the human gut may reach a concentration of 100 µM, which may give effects to gut microorganisms.
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http://dx.doi.org/10.1038/s41598-020-66251-yDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7283484PMC
June 2020

Vernodalidimer L, a sesquiterpene lactone dimer from Vernonia extensa and anti-tumor effects of vernodalin, vernolepin, and vernolide on HepG2 liver cancer cells.

Bioorg Chem 2019 11 16;92:103197. Epub 2019 Aug 16.

Laboratory of Natural Products, Chulabhorn Research Institute, Bangkok 10210, Thailand; Program of Chemical Biology, Chulabhorn Graduate Institute, Chulabhorn Royal Academy, Bangkok 10210, Thailand; The Center of Excellence on Environmental Health and Toxicology, Commission on Higher Education, Ministry of Education, Bangkok 10400, Thailand.

Vernonia extensa, known as "Phim Phai Lin" in Thai, is distributed in most regions of Thailand. The plant has been used in Ayurveda and traditionally used to treat malaria and cancer, and possesses several sesquiterpene lactones. This study aimed to investigate and identify the active constituents by bioactivity-based analysis, as well as to evaluate the cytotoxic activity of V. extensa by MTT or XTT assays in ten cancer cell lines (Liver HepG2 and S102; Bile duct HuCCA-1; Leukemia HL-60 and MOLT-3; Lung A549 and H69AR; Breast MDA-MB-231 and T47D; Cervical HeLa). Bioactivity-guided fractionation and semi-preparative HPLC purification were used to separate the bioactive constituents. Apoptosis-inducing activity and cell cycle inhibitory effect of selected active compounds were determined on HepG2 cells by flow cytometric analysis. Bioactivity-guided fractionation of the CHCl extract and chemical investigation of the cytotoxic fractions led to the isolation of a new sesquiterpenoid pseudo-dimer named vernodalidimer L, together with eight known sesquiterpenoids from the aerial part of V. extensa. The structures of the isolates were elucidated based on spectroscopic analysis, including 1D and 2D NMR and HRMS. Vernolide has potent broad-spectrum cytotoxicity with IC values in the range of 0.91-13.84 μM, against all ten cancer cell lines. The annexin-V flow cytometric analysis showed that vernodalin, vernolepin, and vernolide induced apoptosis on HepG2 cells in a dose dependent manner and these effects correlated with G2/M phase cell cycle arrest. Our results indicated that vernodalin, vernolepin, and vernolide have potential to be used as lead compounds in the development of a therapeutic natural product for treatment of liver cancer.
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http://dx.doi.org/10.1016/j.bioorg.2019.103197DOI Listing
November 2019

A new 22,26- physalin steroid from .

Nat Prod Res 2020 Apr 8;34(8):1097-1104. Epub 2019 Jan 8.

Laboratory of Natural Products, Chulabhorn Research Institute, Bangkok, Thailand.

A new 22,26- physalin, physalin XI () together with 5 known compounds, were isolated from the dichloromethane extract of L. The structure of isolated compounds was elucidated by spectroscopic analysis. The effects of isolated compounds on cytotoxicity were investigated. Compound was assessed for its cytotoxicity against cancer cell lines (HepG2, HeLa, HuCCA-1, T47-D and A-549) and a normal cell line (MRC-5), and the result showed that it has no activity. Compounds and are highly toxic to H69AR and MDA-MB-23 cell lines. This property appears to be related to the presence of their conjugated double bond or epoxy groups and is a more reliable indication of toxicity than substitution on C(5)-C(6).
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http://dx.doi.org/10.1080/14786419.2018.1550766DOI Listing
April 2020

Cytotoxic Cardiac Glycoside Constituents of Vallaris glabra Leaves.

J Nat Prod 2017 11 26;80(11):2987-2996. Epub 2017 Oct 26.

Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University , Hua Mark, Bangkapi, Bangkok 10240, Thailand.

Thirteen cardenolide glycosides (1-13) were isolated from the CHCl and MeOH extracts of Vallaris glabra leaves. The structures of the new compounds (2-13) were identified by spectroscopic methods, with the absolute configurations of the sugar moieties determined by acid hydrolysis. All compounds were evaluated for their cytotoxic activity against human cervix adenocarcinoma, lung carcinoma, and colorectal adenocarcinoma cell lines. The two most potent compounds [2'-O-acetylacoschimperoside P (1) and oleandrigenin-3-O-α-l-2'-O-acetylvallaropyranoside (2)] exhibited IC values in the range of 0.03-0.07 μM.
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http://dx.doi.org/10.1021/acs.jnatprod.7b00554DOI Listing
November 2017

Roscotanes and roscoranes: Oxygenated abietane and pimarane diterpenoids from Kaempferia roscoeana.

Phytochemistry 2017 Nov 28;143:36-44. Epub 2017 Jul 28.

Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand. Electronic address:

Eight previously undescribed ditepenoids, including four oxygenated abietanes (roscotanes A-D) and four oxygenated pimaranes (roscoranes A-D), along with twelve known diterpenoids were isolated from the whole plants of Kaempferia roscoeana. Their structures were elucidated by extensive spectroscopic analysis, and the structure of roscotane A was further confirmed by single crystal X-ray diffraction analysis. Most isolated compounds were evaluated for their antimicrobial and antimalarial activities.
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http://dx.doi.org/10.1016/j.phytochem.2017.07.008DOI Listing
November 2017

Superbanone, A New 2-Aryl-3-benzofuranone and Other Bioactive Constituents from the Tube Roots of Butea superba.

Chem Biodivers 2017 Jul 29;14(7). Epub 2017 May 29.

Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok, 10210, Thailand.

Phytochemical investigation from the tube roots of Butea superba, led to the isolation and identification of a new 2-aryl-3-benzofuranone named superbanone (1), one benzoin, 2-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (2), eight pterocarpans (3 - 10), and eleven isoflavonoids (11 - 21). Compound 2 was identified for the first time as a natural product. The structure of the isolated compounds was elucidated using spectroscopic methods, mainly 1D- and 2D-NMR. The isolated compounds and their derivatives were evaluated for α-glucosidase inhibitory and antimalarial activities. Compounds 3, 7, 8, and 11 showed promising α-glucosidase inhibitory activity (IC  = 13.71 ± 0.54, 23.54 ± 0.75, 28.83 ± 1.02, and 12.35 ± 0.36 μm, respectively). Compounds 3 and 11 were twofold less active than the standard drug acarbose (IC  = 6.54 ± 0.04 μm). None of the tested compounds was found to be active against Plasmodium falciparum strain 94. On the basis of biological activity results, structure-activity relationships are discussed.
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http://dx.doi.org/10.1002/cbdv.201700044DOI Listing
July 2017

Ailanthusins A-G and nor-lupane triterpenoids from Ailanthus triphysa.

Phytochemistry 2017 Feb 25;134:98-105. Epub 2016 Nov 25.

Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand; Chulabhorn Graduate Institute and Center for Environmental Health and Toxicology (EHT), Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.

Bioactivity-guided chemical investigation of the CHCl and CHClMeOH extracts of the stem and stem bark material of Ailanthus tryphysa (Simaroubaceae) led to the isolation of five cycloapotirucallanes, ailanthusins A-E, two malabaricanes, ailanthusins F-G, and one nor-lupane triterpenoid, 29-nor-lup-1-ene-3,20-dione along with twenty known compounds. Their structures were elucidated through the application of extensive spectroscopic methods, and the structure of ailanthusin A was further confirmed by single crystal X-ray analysis. Several malabaricane derivatives were prepared from malabaricol and, together with some of the isolates, were evaluated for their cytotoxic activities against human cancer and normal cell lines.
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http://dx.doi.org/10.1016/j.phytochem.2016.11.007DOI Listing
February 2017

Polyoxygenated ursane and oleanane triterpenes from Siphonodon celastrineus.

Phytochemistry 2016 Sep 25;129:58-67. Epub 2016 Jul 25.

Chulabhorn Research Institute, Kamphaeng Phet 6 Road, Bangkok 10210, Thailand; Chulabhorn Graduate Institute and Center for Environmental Health and Toxicology (EHT), Kamphaeng Phet 6 Road, Bangkok 10210, Thailand.

Twenty polyoxygenated triterpenes, including nineteen ursanes and one oleanane, were characterized from the stem material of Siphonodon celastrineus (Celastraceae) through the application of spectroscopic techniques and chemical transformation. Three of the ursane-type triterpenoids possessed the rare 13,27-cyclopropane ring skeleton.
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http://dx.doi.org/10.1016/j.phytochem.2016.07.006DOI Listing
September 2016

Eriosema chinense: a rich source of antimicrobial and antioxidant flavonoids.

Phytochemistry 2013 Dec 15;96:353-9. Epub 2013 Oct 15.

Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Hua Mark, Bangkapi, Bangkok 10240, Thailand.

Six prenylated flavonoids, (2R,3S)-3,5,4'-trihydroxy-6″-6″dimethylpyrano(2″,3″:7,6)-8-(3″', 3″'-dimethylallyl)flavanone, (2R,3S)-3,5,2'-trihydroxy-4'-methoxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″',3″'-dimethylallyl)flavanone, (2R,3R)-3,5,2',4'-tetrahydroxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″',3″'-dimethylallyl)flavanone, 3,5,2',4'-tetrahydroxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″',3″'-dimethylallyl)flavone, (2R,3R,2″'R)-3,5,2″'-trihydroxy-4'-methoxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(3″'-methylbut-3″'-enyl)flavanone, (2R,3R)-3,5-dihydroxy-4'-methoxy-6″,6″-dimethylpyrano(2″,3″:7,6)-8-(2″',3″'-epoxy-3″'-methyl butyl)flavanone, an isoflavone, 6,7-dimethoxy-5,2',4'-trihydroxyisoflavone, and octaeicosanyl-trans-p-coumarate together with 12 known compounds, were isolated from roots of Eriosema chinense. This structural elucidation was determined by spectroscopic methods. Several isolates and derivatives were evaluated for their antimicrobial and antioxidant activities. Results obtained provide additional evidence showing that the presence of both the free phenolic OH and the lipophilic prenyl groups are crucial for potent antimicrobial activity against yeast, gram positive and gram negative bacteria, whereas the presence of free phenolic OH group is required for strong radical scavenging property.
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http://dx.doi.org/10.1016/j.phytochem.2013.06.004DOI Listing
December 2013

Oxygenated pimarane diterpenes from Kaempferia marginata.

J Nat Prod 2005 Nov;68(11):1632-6

Chulabhorn Research Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand.

Six new diterpenes, (1R,2S,5S,7S,9R,10S,13R)-1,2,7-trihydroxypimara-8(14),15-diene (1), (1R,2S,5S,9S,10S,11R,13R)-1,2,11-trihydroxypimara-8(14),15-diene (2), (1S,5S,7R,9R,10S,11R,13R)-1,7,11-trihydroxypimara-8(14),15-diene (3), (1S,5S,9S,10S,11R,13R)-1,11-dihydroxypimara-8(14),15-diene (4), (5S, 6R,9S,10S,13R)-6-hydroxypimara-8(14),15-diene-1-one (5), and (1R,2S,5S,7S,9R,10S,13R)-1,2-dihydroxypimara-8(14),15-diene-7-one (6), along with four known diterpenes, have been isolated from the dichloromethane extract of whole plants of Kaempferia marginata. The structures were assigned by spectroscopic methods. The absolute configuration of 1 was established by the Mosher ester method. Substances obtained were evaluated against a panel of bioassays including antimalarial, antituberculous, and antifungal activity.
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http://dx.doi.org/10.1021/np050186lDOI Listing
November 2005

Determination and variation of three active diterpenoids in Andrographis paniculata (Burm.f.) Nees.

Phytochem Anal 2004 Nov-Dec;15(6):365-71

Laboratory of Pharmacology, Chulabhorn Research Institute, Vibhavadee-Rangsit Highway, Laksi, Bangkok 10210, Thailand.

Simple and rapid methods have been developed for the extraction and simultaneous determination of the three active diterpenoids, andrographolide (AP1), 14-deoxy-11,12-didehydroandrographolide (AP3) and neoandrographolide (AP4), from various samples of Andrographis paniculata (Burm.f.) Nees. Methanol extracts from the dried leaves, stems and crude products were analysed by isocratic HPLC using a methanol and water mobile phase with monitoring at 220 nm. There was a large variation of the three active diterpenoids in different A. paniculata products obtained from Thai markets. The results indicated that the amounts of these active compounds consumed, based on the recommended daily doses, from materials obtained from the different suppliers will be different. In addition, the stability of these three active compounds was also examined in dry herbs stored at room temperature. The results showed that andrographolide was more stable than the others. In contrast, the content of 14-deoxy-11,12-didehydroandrographolide increased and the neoandrographolide content fluctuated during storage time. The combination of different levels of these compounds in the source materials and the changes during storage could have a significant effect on the efficacy of this traditional herbal medicine in clinical treatment.
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http://dx.doi.org/10.1002/pca.789DOI Listing
January 2005

Anti-metastatic effects of aqueous extract of Helixanthera parasitica.

J Ethnopharmacol 2003 Jun;86(2-3):253-6

Laboratory of Biochemistry, Chulabhorn Research Institute, Bangkok 10210, Thailand.

Metastasis, the spread of cancer in body, is a major cause of death. We have screened anti-metastatic activity of aqueous and dichloromethane extracts of several not previously studied Thai herbs, using an in vitro invasion test. This involves the in vitro invasion of HCC-S102, a hepatocellular carcinoma cell line derived from a Thai patient, through a reconstituted-basement membrane (Matrigel). The aqueous extract of a plant (Helixanthera parasitica) revealed a significant inhibitory effect on the cancer cell invasion, and showed antioxidant activity. The aqueous extract was partially purified by silica gel column chromatography, and the highest anti-metastatic activity fraction showed 83% inhibition of invasion with low cytotoxic effect. However, anti-metastatic activity was not associated with the antioxidant activity of the aqueous extract.
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http://dx.doi.org/10.1016/s0378-8741(03)00072-2DOI Listing
June 2003