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Differentiation of Ficus deltoidea varieties and chemical marker determination by UHPLC-TOFMS metabolomics for establishing quality control criteria of this popular Malaysian medicinal herb

Afzan A, Kasim N, Ismail NH, Azmi N, Ali AM, Mat N, et al.

Metabolomics, 2019 Mar 04;15(3):35.
PMID: 30830457 DOI: 10.1007/s11306-019-1489-2

BACKGROUND: Ficus deltoidea Jack (Moraceae) is a plant used in Malaysia for various diseases including as a supplement in diabetes management. Morphology distinction of the 7 main varieties (var. angustifolia, var. bilobata, var. deltoidea, var. intermedia, var. kunstleri, var. motleyana and var. trengganuensis) is challenging due to the extreme leaf heterophylly and unclear varietal boundaries, making it difficult for quality control of F. deltoidea products.
OBJECTIVE: We aimed to compare the phytochemical composition of 7 varieties growing in different conditions at various geographical locations. We also aimed to establish the quality control markers for the authentication of these varieties.
METHODS: We applied untargeted UHPLC-TOFMS metabolomics to discriminate 100 leaf samples of F. deltoidea collected from 6 locations in Malaysia. A genetic analysis on 21 leaf samples was also performed to validate the chemotaxonomy differentiation.
RESULTS: The PCA and HCA analysis revealed the existence of 3 chemotypes based on the differentiation in the flavonoid content. The PLS-DA analysis identified 15 glycosylated flavone markers together with 1 furanocoumarin. These markers were always consistent for the respective varieties, regardless of the geographical locations and growing conditions. The chemotaxonomy differentiation was in agreement with the DNA sequencing. In particular, var. bilobata accession which showed divergent morphology was also differentiated by the chemical fingerprints and genotype.
CONCLUSION: Chemotype differentiation based on the flavonoid fingerprints along with the proposed markers provide a powerful identification tool to complement morphology and genetic analyses for the quality control of raw materials and products from F. deltoidea.
Fulltext In Vitro Pro-apoptotic and Anti-migratory Effects of Ficus deltoidea L. Plant Extracts on the Human Prostate Cancer Cell Lines PC3

Hanafi MMM, Afzan A, Yaakob H, Aziz R, Sarmidi MR, Wolfender JL, et al.

Front Pharmacol, 2017;8:895.
PMID: 29326585 DOI: 10.3389/fphar.2017.00895

This study aims to evaluate the in vitro cytotoxic and anti-migratory effects of Ficus deltoidea L. on prostate cancer cells, identify the active compound/s and characterize their mechanism of actions. Two farmed varieties were studied, var. angustifolia (FD1) and var. deltoidea (FD2). Their crude methanolic extracts were partitioned into n-hexane (FD1h, FD2h) chloroform (FD1c, FD2c) and aqueous extracts (FD1a, FD2a). Antiproliferative fractions (IC50 < 30 μg/mL, SRB staining of PC3 cells) were further fractionated. Active compound/s were dereplicated using spectroscopic methods. In vitro mechanistic studies on PC3 and/or LNCaP cells included: annexin V-FITC staining, MMP depolarization measurements, activity of caspases 3 and 7, nuclear DNA fragmentation and cell cycle analysis, modulation of Bax, Bcl-2, Smac/Diablo, and Alox-5 mRNA gene expression by RT-PCR. Effects of cytotoxic fractions on 2D migration and 3D invasion were tested by exclusion assays and modified Boyden chamber, respectively. Their mechanisms of action on these tests were further studied by measuring the expression VEGF-A, CXCR4, and CXCL12 in PC3 cells by RT-PCR. FD1c and FD2c extracts induced cell death (P < 0.05) via apoptosis as evidenced by nuclear DNA fragmentation. This was accompanied by an increase in MMP depolarization (P < 0.05), activation of caspases 3 and 7 (P < 0.05) in both PC3 and LNCaP cell lines. All active plant extracts up-regulated Bax and Smac/DIABLO, down-regulated Bcl-2 (P < 0.05). Both FD1c and FD2c were not cytotoxic against normal human fibroblast cells (HDFa) at the tested concentrations. Both plant extracts inhibited both migration and invasion of PC3 cells (P < 0.05). These effects were accompanied by down-regulation of both VEGF-A and CXCL-12 gene expressions (P < 0.001). LC-MS dereplication using taxonomy filters and molecular networking databases identified isovitexin in FD1c; and oleanolic acid, moretenol, betulin, lupenone, and lupeol in FD2c. In conclusion, FD1c and FD2c were able to overcome three main hallmarks of cancer in PC3 cells: (1) apoptosis by activating of the intrinsic pathway, (2) inhibition of both migration and invasion by modulating the CXCL12-CXCR4 axis, and (3) inhibiting angiogenesis by modulating VEGF-A expression. Moreover, isovitexin is here reported for the first time as an antiproliferative principle (IC50 = 43 μg/mL, SRB staining of PC3 cells).
Correlation of chemical profiles obtained from 1 H-NMR and LC-MS metabolomics with α-glucosidase inhibition activity for varietal selections of Ficus deltoidea

Kasim N, Afzan A, Mediani A, Low KH, Ali AM, Mat N, et al.

Phytochem Anal, 2022 Dec;33(8):1235-1245.
PMID: 36192845 DOI: 10.1002/pca.3175

INTRODUCTION: Ficus deltoidea Jack (Moraceae) is a plant used in Malaysia to treat various ailments, including diabetes. The presence of several varieties raises essential questions regarding which is the potential bioactive variety and what are the bioactive metabolites.
OBJECTIVES: Here, we explored the phytochemical diversity of the seven varieties from Peninsular Malaysia using Nuclear Magnetic Resonance (NMR) and Liquid Chromatography-Mass Spectrometry (LC-MS) analyses and correlated it with the α-glucosidase inhibitory activity.
METHODOLOGY: The Nuclear Overhauser Effect Spectroscopy (NOESY) One-Dimensional (1D)-NMR and LC-MS data were processed, annotated, and correlated with in vitro α-glucosidase inhibitory using multivariate data analysis.
RESULTS: The α-glucosidase results demonstrated that different varieties have varying inhibitory effects, with the highest inhibition rate being F. deltoidea var. trengganuensis and var. kunstleri. Furthermore, diverse habitats and plant ages could also influence the inhibitory rate. The heat map from NMR and LC-MS profiles showed unique patterns according to varying levels of α-glucosidase inhibition rate. The Partial Least Squares (PLS) model constructed from both NMR and LC-MS further confirmed the correlation between the α-glucosidase inhibition rate of F. deltoidea varieties and its metabolite profiles. The Variable Influence on Projection (VIP) and correlation coefficient (p(corr)) values values were used to determine the highly relevant metabolites for explaining the anticipated inhibitory action.
CONCLUSION: NMR and LC-MS annotations allow the identification of flavan-3-ols and proanthocyanidins as the key bioactive factors. Our current results demonstrated the value of multivariate data analysis to predict the quality of herbal materials from both biological and chemical aspects.
Fulltext Chemical characterizations dataset of flavonoid glycoside isomers and other constituents from Ficus deltoidea Jack

Afzan A, Marcourt L, Abd Karim HA, Kasim N, Queiroz EF, Osman CP, et al.

Data Brief, 2024 Jun;54:110414.
PMID: 38690315 DOI: 10.1016/j.dib.2024.110414

Phytochemical data for Ficus deltoidea Jack, a plant widely studied for its anti-hyperglycemic effect, are scarce. In the pursuit of characterizing the chemical constituents of this species, extraction and purifications were conducted using multiple chromatographic procedures on selected varieties (var. deltoidea, var. kunstleri and var. trengganuensis). Twenty-two constituents were unambiguously identified through NMR, MS and UV data. These included gallocatechin (S1), afzelechin-4-8″-gallocatechin (S2), catechin (S3), afzelechin-4-8″-catechin (S4), afzelechin (S5), epicatechin (S6), hovetrichoside C (S7), 6,8-di-C-glucopyranosylapigenin (vicenin-2) (S8), afzelechin-4-8″-epiafzelechin (S9), epiafzelechin (S10), 6-C-xylopyranosyl-8-C-glucopyranosylapigenin (vicenin-1) (S11), orientin (S13), schaftoside (S14), 6-C-glucopyranosyl-8-C-xylopyranosylapigenin (vicenin-3) (S16), vitexin (S17), vitexin 2″-O-rhamnoside (S19), isovitexin 2″-O-rhamnoside (S20), 6,8-di-C-arabinopyranosylapigenin (S21), 6,8-di-C-xylopyranosylapigenin (S22), 6-C-arabinopyranosyl-8-C-xylopyranosylapigenin (S23), rhoifolin (S24) and cerberic acid A (S26). The presented phytochemical data can assist ethnobotanists, chemists, and natural product researchers in investigating the medicinal properties of F. deltoidea by facilitating the dereplication of its constituents.