Katherine Yasmin M. Garcia

University of Santo Tomas

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Allan Patrick G. Macabeo

University of Santo Tomas

Mark Tristan J. Quimque

Mindanao State University – Iligan Institute of Technology

Marc Stadler

Helmholtz Centre for Infection Research

Chayanard Phukhamsakda

Mae Fah Luang University

Andreas Ratzenböck

University of Regensburg

Kevin D. Hyde

Mae Fah Luang University

Allaine Jean C. Cruz

University of Santo Tomas

Gian Primahana

National Research and Innovation Agency

Frank Surup

Helmholtz Centre for Infection Research

Luis Agustin E. Pilapil

University of the Philippines Diliman

Cooperative Institutions

University of Santo Tomas

Helmholtz Centre for Infection Research

German Center for Infection Research

Technische Universität Braunschweig

Mae Fah Luang University

Scripps Institution of Oceanography

University of Tabriz

Mae Fah Luang University Hospital

Zhongkai University of Agriculture and Engineering

Ministry of Agriculture and Rural Affairs

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Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation

Journal of Fungi (2022)

Katherine Yasmin M. Garcia Mark Tristan J. Quimque Christopher Lambert Katharina Schmidt Gian Primahana

Laying the groundwork on preliminary structure–activity relationship study relating to the disruptive activity of cytochalasan derivatives on mammalian cell actin cytoskeleton, we furthered our study on the cytochalasans of the Dothideomycetes fungus, Sparticola triseptata. A new cytochalasan analog triseptatin (1), along with the previously described cytochalasans deoxaphomin B (2) and cytochalasin B (3), and polyketide derivatives cis-4-hydroxy-6-deoxyscytalone (4) and 6-hydroxymellein (5) were isolated from the rice culture of S. triseptata. The structure of 1 was elucidated through NMR spectroscopic analysis and high-resolution mass spectrometry (HR-ESI-MS). The relative and absolute configurations were established through analysis of NOESY spectroscopic data and later correlated with experimental electronic circular dichroism and time-dependent density functional theory (ECD–TDDFT) computational analysis. Compounds 1 and 2 showed cytotoxic activities against seven mammalian cell lines (L929, KB3.1, MCF-7, A549, PC-3, SKOV-3, and A431) and antiproliferative effects against the myeloid leukemia K-562 cancer cell line. Both 1 and 2 were shown to possess properties inhibiting the F-actin network, prompting further hypotheses that should to be tested in the future to enable a well-resolved concept of the structural implications determining the bioactivity of the cytochalasin backbone against F-actin.

Cytochalasin D

Cytochalasin

10.3390/jof8060560

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Citations (12)

Alpha-Glucosidase- and Lipase-Inhibitory Phenalenones from a New Species of Pseudolophiostoma Originating from Thailand

Molecules (2020)

Allan Patrick G. Macabeo Luis Agustin E. Pilapil Katherine Yasmin M. Garcia Mark Tristan J. Quimque Chayanard Phukhamsakda

The alpha-glucosidase- and lipase-inhibitory activities of three phenalenones (1-3) and one phenylpropanoid (4) from the ethyl acetate extracts of a Pseudolophiosptoma sp. are described. They represent the first secondary metabolites reported from the genus Pseudolophiostoma. Scleroderolide (1) and sclerodione (2) exhibited potent α-glucosidase- and porcine-lipase-inhibitory activity during primary screening, with better IC50 values compared to the positive controls, N-deoxynojirimycin and orlistat. In silico techniques were employed to validate the probable biological targets and elucidate the mechanism of actions of phenalenones 1 and 2. Both compounds exhibited strong binding affinities to both alpha-glucosidase and porcine lipase through H-bonding and π-π interactions. Interestingly, favorable in silico ADME (absorption, distribution, metabolism, and excretion) properties such as gastrointestinal absorption were also predicted using software.

ADME

Alpha-glucosidase

IC50

Orlistat

10.3390/molecules25040965

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Citations (28)

Catechol-Bearing Polyketide Derivatives from Sparticola junci

Journal of Natural Products (2021)

Katherine Yasmin M. Garcia Chayanard Phukhamsakda Mark Tristan J. Quimque Kevin D. Hyde Marc Stadler

Sparticols A (1) and B (2), two catechol-bearing naphthalenedioxy derivatives, were isolated from the submerged culture of the Spanish broom inhabiting Dothideomycetes fungus, Sparticola junci. The structures of 1 and 2 were established by NMR spectroscopic analysis and high-resolution mass spectrometry. The 8S absolute configuration of their β-hydroxy functionalities was determined by ECD-TDDFT. Both compounds exhibited inhibitory activity against Staphylococcus aureus with an MIC value of 66.6 μg/mL. Polyketides 1 and/or 2 may be associated with pathways cascading to seco-spirodioxynapthalene derivatives.

Catechol

Absolute Configuration

10.1021/acs.jnatprod.1c00415

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COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci

International Journal of Molecular Sciences (2021)

Katherine Yasmin M. Garcia Mark Tristan J. Quimque Gian Primahana Andreas Ratzenböck Mark Joseph B. Cano

Axenic fermentation on solid rice of the saprobic fungus Sparticola junci afforded two new highly oxidized naphthalenoid polyketide derivatives, sparticatechol A (1) and sparticolin H (2) along with sparticolin A (3). The structures of 1 and 2 were elucidated on the basis of their NMR and HR-ESIMS spectroscopic data. Assignment of absolute configurations was performed using electronic circular dichroism (ECD) experiments and Time-Dependent Density Functional Theory (TDDFT) calculations. Compounds 1-3 were evaluated for COX inhibitory, antiproliferative, cytotoxic and antimicrobial activities. Compounds 1 and 2 exhibited strong inhibitory activities against COX-1 and COX-2. Molecular docking analysis of 1 conferred favorable binding against COX-2. Sparticolin H (2) and A (3) showed a moderate antiproliferative effect against myelogenous leukemia K-562 cells and weak cytotoxicity against HeLa and mouse fibroblast cells.

HeLa

Axenic

MTT assay

10.3390/ijms222212379

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Citations (10)

Effects of lipid removal and preservatives on carbon and nitrogen stable isotope ratios of squid tissues: Implications for ecological studies

Journal of Experimental Marine Biology and Ecology (2011)

RI Ruiz-Cooley Katherine Yasmin M. Garcia Elizabeth D. Hetherington

δ15N

Isotopes of nitrogen

10.1016/j.jembe.2011.07.002

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An α-Glucosidase and Pancreatic Lipase Inhibitory Cytochalasan Derivative from the Dothideomycetes fungus, Sparticola triseptata

Acta Manilana (2023)

Katherine Yasmin M. Garcia Joe Anthony Manzano Allan Patrick G. Macabeo

The previously known cytotoxic cytochalasan, cytochalasin B (1), was isolated and purified from the ethyl acetate extract of the rice fermentation culture of the Alpine asphodel-associated Dothideomycetes fungus, Sparticola triseptata after iterative chromatographic purifications.The structure of 1 was established through extensive 1D and 2D-NMR spectroscopic experiments along with high-resolution electrospray ionization mass spectrometry (HRESIMS) and by comparison of its spectroscopic data with the literature.The potential of cytochalasin B (1) as antidiabetic and anti-obesity compound was screened using microplate, colorimetric enzyme inhibitory assays.Thus, 1 displayed significant in vitro α-glucosidase and porcine pancreatic lipase inhibitory activities with IC 50 values of 5.46 µM and 8.43 µM, respectively when compared to the positive drug controls, acarbose and Orlistat ® .Molecular simulation experiments using molecular docking showed moderately strong affinity of 1 onto the active sites of α-glucosidase and porcine pancreatic lipase with binding energies (BE) of -8.6 kcal/mol and -7.5 kcal/mol, respectively.

Dothideomycetes

Filamentous fungus

10.53603/actamanil.71.2023.adzs2369

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Polyoxygenated Cyclohexenes from Uvaria grandiflora with Multi-Enzyme Targeting Properties Relevant in Type 2 Diabetes and Obesity

ACS Omega (2022)

Mark Tristan J. Quimque Ryan Joseph Y. Magsipoc Lloyd Christian J. Llames Angeli Izza G. Flores Katherine Yasmin M. Garcia

Shikimic acid-derived polyoxygenated cyclohexene natural products commonly occurring in several species of the Uvaria represent natural products with promising biological activities. While a number of derivatives have been reported from Uvaria grandiflora (U. grandiflora), further studies are needed to discover additional bioactive congeners, particularly derivatives with multi-protein target inhibitory properties implicated in diseases such as diabetes and obesity. In this paper, isolation and identification of a new highly oxygenated cyclohexene, uvagrandol (1), along with the known compound (-)-zeylenone (2) from the DCM sub-extract of U. grandiflora following in vitro and in silico assessment of their enzyme inhibitory properties against α-glucosidase, dipeptidyl peptidase IV, porcine lipase, and human recombinant monoacylglycerol lipase are reported. The structure of 1 was elucidated using 1D and 2D NMR data analysis. The absolute configuration of 1 was established by quantum chemical calculations via the Gauge-Independent Atomic Orbital (GIAO) NMR method followed by TDDFT-Electronic Circular Dichroism (ECD) calculations. The structures of the eight possible stereoisomers were optimized by means of DFT calculations (B3LYP/6-31+G[d,p] in vacuum), and then their isotropic shielding tensors were obtained using the GIAO method at mPW1PW91/6-31G(d,p) in chloroform. Through DP4+, the isomer of configuration (1S,2S,3R,6R) for 1 was predicted with 96.3% probability. Compounds 1 and 2 significantly inhibited the four target enzymes in vitro. Binding studies through molecular docking simulations showed strong binding affinities for (-)-zeylenone (2), thus validating the in vitro results. Our findings suggest the potential of polyoxygenated cyclohexenes, in particular (-)-zeylenone (2), in anti-diabetic and anti-obesity drug discovery.

Docking (animal)

10.1021/acsomega.2c05544

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Citations (6)

Tetrasubstituted α-pyrone derivatives from the endophytic fungus, Neurospora udagawae

Phytochemistry Letters (2019)

Allan Patrick G. Macabeo Allaine Jean C. Cruz Abolfazl Narmani Mahdi Arzanlou Asadollah Babai‐Ahari

Pyrone

Benzoic acid

Endophyte

Neurospora

10.1016/j.phytol.2019.11.010

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Citations (21)