Two Flavonoid Compounds as Antiproliferative Activity Against SP-C1 Cancer Tongue Cells from the Leaves of Rasamala  (Altingia excelsa Nornha)

Two flavonoid compounds, kaempferol (1) and quercetin (2) have been isolated from the leaves of Rasamala (Altingia excelsa Nornha). The chemical structure of compounds 1 and 2 were identified by spectroscopic evidences including, UV, IR, 1D-NMR, 2D-NMR and MS as well as by comparing with previously reported spectral data.These compounds were isolated from this plant for the first time. Compounds 1 and 2 were evaluated for their antiproliferative activity against SP-C1 cancer tongue cells and showed IC50 values of 2.50 and 2.31 mM, respectively.

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Dammarane-Type Triterpenoids from The Stembark of Aglaia argentea (Meliaceae)

Jurnal Kimia VALENSI ◽

10.15408/jkv.v4i1.7065 ◽

2018 ◽

Vol 4 (1) ◽

pp. 7-13

Author(s):

Ace Tatang Hidayat ◽

Kindi Farabi ◽

Ida Nur Farida ◽

Kansy Haikal ◽

Nurlelasari Nurlelasari ◽

...

Keyword(s):

Cytotoxic Activity ◽

Spectral Data ◽

Chemical Structure ◽

2D Nmr ◽

Leukemia Cells ◽

Ic50 Values ◽

First Time ◽

Murine Leukemia

Two dammarane-type triterpenoids, 20S,24S-epoxy-3α,25-dihydroxydammarane (1) and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (2), have been isolated from the stembark of Aglaia argentea. The chemical structure of compounds (1 and 2) were identified by spectroscopic evidences including UV, IR, 1D-NMR, 2D-NMR and MS as well as by comparing with previously reported spectral data. Those compounds were isolated from this plant for first time. Compounds (1 and 2) showed cytotoxic activity against P-388 murine leukemia cells with IC50 values of 23.96 and 8.14 mM, respectively.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7065

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tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion

Molecules ◽

10.3390/molecules23081951 ◽

2018 ◽

Vol 23 (8) ◽

pp. 1951 ◽

Cited By ~ 2

Author(s):

Thi-Bach-Le Nguyen ◽

Olivier Delalande ◽

Isabelle Rouaud ◽

Solenn Ferron ◽

Laura Chaillot ◽

...

Keyword(s):

Bacterial Strain ◽

2D Nmr ◽

One Dimensional ◽

Spectroscopic Analyses ◽

Human Keratinocyte ◽

Rhizocarpon Geographicum ◽

Ionisation Mass Spectrometry ◽

Keratinocyte Cell ◽

Ic50 Values ◽

First Time

Two compounds (1) and (2) containing tert-butylphenol groups were, for the first time, produced during the culture of Paenibacillus odorifer, a bacterial strain associated with the crustose lichen, Rhizocarpon geographicum. Their entire structures were identified by one-dimensional (1D) and two-dimensional (2D) NMR and high-resolution electrospray ionisation mass spectrometry (HRESIMS) spectroscopic analyses. Among them, Compound 1 exhibited significant cytotoxicity against B16 murine melanoma and HaCaT human keratinocyte cell lines with micromolar half maximal inhibitory concentration (IC50) values. Furthermore, after supplementation studies, a putative biosynthesis pathway was proposed for Compound 1 throughout a bioconversion by this bacterial strain of butylated hydroxyanisole (BHA), an antioxidant polymer additive.

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Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

Molecules ◽

10.3390/molecules24081561 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1561 ◽

Cited By ~ 1

Author(s):

Qiao ◽

Khutsishvili ◽

Alizade ◽

Atha ◽

Borris

Keyword(s):

Cell Lines ◽

Human Tumor ◽

2D Nmr ◽

Human Tumor Cell Lines ◽

Abietane Diterpenoids ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Values ◽

First Time ◽

Mcf 7

A phytochemical investigation of the whole plant of Juniperus oblonga led to the isolationof one previously undescribed labdane diterpenoid, (4R,5S,9S,10R)‐13‐des‐ethyl‐13‐oxolabda‐8(17),11E‐dien‐19‐oic acid (1), together with nine known diterpenoids (2–3, 6–12), two lignans (4, 5),and a coumarin (13). The structures of all the compounds were elucidated on the basis ofspectrometric data, primarily one‐dimensional (1D)‐ and two‐dimensional (2D)‐NMR and massspectrometry. Electronic circular dichroism (ECD) calculations determined the absoluteconfiguration of 1. In addition, the isolated compounds were evaluated for their cytotoxic activityagainst three human tumor cell lines (HepG2, MCF‐7, and HeLa). 6,12‐Dihydroxyabieta‐5,8,11,13‐tetraen‐7‐one (6) showed moderate cytotoxicity against all three cell lines with IC50 values rangingfrom 24.41 μM to 58.39 μM and trilobinone (10) showed weaker activity with IC50 values rangingfrom 56.93 μM to 79.98 μM. None of the isolated diterpenoids have been previously reported fromJuniperus oblonga, and five compounds are here reported from the genus Juniperus for the first time.

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Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera

Marine Drugs ◽

10.3390/md18120608 ◽

2020 ◽

Vol 18 (12) ◽

pp. 608

Author(s):

Elena V. Girich ◽

Anton N. Yurchenko ◽

Olga F. Smetanina ◽

Phan Thi Hoai Trinh ◽

Ngo Thi Duy Ngoc ◽

...

Keyword(s):

Molecular Weight ◽

Secondary Metabolites ◽

Cell Viability ◽

Chemical Structure ◽

Aspergillus Terreus ◽

Marine Fungi ◽

2D Nmr ◽

Natural Source ◽

Low Molecular Weight ◽

First Time

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds were determined by 1D and 2D NMR and HR-ESI-MS techniques. Stereochemistry of some compounds was established based on ECD data. A chemical structure of asterriquinone F (6) was thoroughly described for the first time. Anthraquinone (13) was firstly obtained from a natural source. Neuroprotective influences of the isolated compounds against 6-OHDA, paraquat and rotenone toxicity were investigated. 4-Hydroxyscytalone (1), 4-hydroxy-6-dehydroxyscytalone (2) and demethylcitreoviranol (3) have shown significant increasing of paraquat- and rotenone-treated Neuro-2a cell viability and anti-ROS activity.

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Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽

10.3390/molecules25173927 ◽

2020 ◽

Vol 25 (17) ◽

pp. 3927

Author(s):

Jing-Shuai Wu ◽

Xiao-Hui Shi ◽

Ya-Hui Zhang ◽

Chang-Lun Shao ◽

Xiu-Mei Fu ◽

...

Keyword(s):

Aspergillus Terreus ◽

Epigenetic Modification ◽

2D Nmr ◽

Etoac Extract ◽

One Dimensional ◽

X Ray ◽

Deacetylase Inhibitor ◽

Ic50 Values ◽

First Time ◽

Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

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Four Flavan-3-ol Compounds From The Stembark of Chisocheton balansae C.DC. (MELIACEAE)

Molekul ◽

10.20884/1.jm.2021.16.1.642 ◽

2021 ◽

Vol 16 (1) ◽

pp. 9

Author(s):

Unang Supratman ◽

Mohamad Fajar ◽

Supriatno Salam ◽

Rani Maharani ◽

Desi Harneti ◽

...

Keyword(s):

Ethyl Acetate ◽

13C Nmr ◽

Chemical Structure ◽

Ethyl Acetate Extract ◽

2D Nmr ◽

Stem Bark ◽

Spectroscopic Methods ◽

Endemic Plants ◽

North Sulawesi ◽

First Time

Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1), epicatechin (2), epigallocatechin-3-O-gallate (3), and epicatechin-3-O-gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods (1H-NMR, 13C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.

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Melicope moluccana Antimalarial Activity of Furoquinoline Alkaloids from the Leaves of Melicope moluccana

Journal Of Tropical Pharmacy And Chemistry ◽

10.25026/jtpc.v5i2.260 ◽

2020 ◽

Vol 5 (2) ◽

pp. 138-142

Author(s):

Ryan Ayub Wahjoedi ◽

Ratih Dewi Saputri ◽

Tjitjik Srie Tjahjandarie ◽

Mulyadi Tandjung

Keyword(s):

Plasmodium Falciparum ◽

Spectral Data ◽

Spectroscopic Data ◽

Chemical Structure ◽

Antimalarial Activity ◽

2D Nmr ◽

Esi Ms ◽

Ic50 Values

Two furoquinoline alkaloids, leptanoine C (1) and haplopine-3,3´-dimethylallyl ether (2) were isolated from the leaves of Melicope moluccana. The chemical structure of both compounds was determined based on spectroscopic data, including UV, IR, HR-ESI-MS, 1D, and 2D NMR spectral data. The antimalarial activity of compounds 1-2 against Plasmodium falciparum 3D7 showing their IC50 values are 0.18 ppm and 2.28 µg/mL, respectively.

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Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Molecules ◽

10.3390/molecules26216626 ◽

2021 ◽

Vol 26 (21) ◽

pp. 6626

Author(s):

Edwin R. Sukandar ◽

Sutin Kaennakam ◽

Pia Raab ◽

Xuehong Nöst ◽

Kitiya Rassamee ◽

...

Keyword(s):

2D Nmr ◽

Stem Bark ◽

No Production ◽

Hep G2 ◽

Pharmacological Studies ◽

Ic50 Values ◽

Hela S3 ◽

Anti Inflammatory ◽

First Time ◽

Mcf 7

Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

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Active constituents of Zanthoxylum nitidum from Yunnan Province against leukemia

10.21203/rs.2.22293/v2 ◽

2020 ◽

Author(s):

Ying Deng ◽

Tongtong Ding ◽

Lulu Deng ◽

Xiaojiang Hao ◽

Shu Zhen Mu

Keyword(s):

Cell Apoptosis ◽

Yunnan Province ◽

2D Nmr ◽

Phase Arrest ◽

Hel Cells ◽

Ic50 Values ◽

Uv Visible ◽

Zanthoxylum Nitidum ◽

First Time ◽

Potential Use

Abstract Zanthoxylum nitidium (Roxb.) DC (Rutaceae) is well known for inhibiting the proliferation of human gastric, liver, kidney and lung cancer cells, whereas research on its potential use in treating leukaemia is relatively rare. 26 compounds were isolated from the chloroform and petroleum ether extracts of the roots and leaves of Z. nitidium. The structures of four compounds (4-6 and 16) were confirmed and attributed firstly by UV-visible spectroscopy, 1D and 2D NMR and HR-ESI-MS. Compounds 1-2 and11 were isolated from Z. nitidium for the first time. Of the assayed compounds, compounds 14 and24 showed inhibitory activities against leukaemia HEL cells with IC50 values of 3.59 and 15.95 µM. In addition, to further investigate the possible mechanism, the cell cycle and apoptosis assays were investigated, which indicated that compound14 caused obvious S phase arrest in HEL cells and induced cell apoptosis, but compound 24 induced only cell apoptosis of HEL cells. These results suggested that compounds 14 and 24 were the potential candidates for anti-leukaemia drug for the first time.

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Flavonoids from the Roots of Amomum compactum Soland Ex Maton (Zingiberaceae)

Jurnal Kimia VALENSI ◽

10.15408/jkv.v7i2.21599 ◽

2021 ◽

Vol 7 (2) ◽

pp. 142-149

Author(s):

Deden Indra Dinata ◽

Rani Maharani ◽

Fauzan Zein Muttaqien ◽

Unang Supratman ◽

Mohamad Nurul Azmi ◽

...

Keyword(s):

Chemical Structure ◽

2D Nmr ◽

Scavenging Activity ◽

Endemic Plants ◽

Spectroscopy Data ◽

Chemical Structures ◽

Dpph Scavenging Activity ◽

Amomum Compactum ◽

Dpph Scavenging ◽

First Time

Amomum compactum Soland Ex Maton is one of the Zingiberaceae family plants which is the endemic plants from West Java, Indonesia. This study was aimed to determine the chemical structure of flavonoid compounds from n-hexane extract of A.compactum Sol. Ex Maton roots. Dried powder of the roots was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Three flavonoids, 5-hydroxy-3,7,4`-trimethoxy kaempferol (1), 5-hydroxy-3,7,3',4'-tetra methoxy kaempferol (2) and 4'-hydroxy-3,5,7-trimethoxy kaempferol (3), have been isolated from the roots of A. compactum Sol. Ex Maton. The chemical structures of compounds 1-3 were identified by spectroscopy data including infrared 1D-NMR, 2D-NMR and HRTOF-MS as well as by comparison with previously reported spectral data. Compounds 1-3 were isolated from this plant for the first time and showed free radical DPPH scavenging activity.

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