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Isolation, Elucidation and Synthesis of Bioactive Natural Products

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A special issue of Separations (ISSN 2297-8739). This special issue belongs to the section "Analysis of Natural Products and Pharmaceuticals".

Deadline for manuscript submissions: closed (31 August 2023) | Viewed by 18330

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Prof. Dr. Norizan Ahmat

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Centre of Foundation Studies, Universiti Teknologi MARA, Cawangan Selangor, Kampus Dengkil, Dengkil 43800, Selangor, Malaysia
Interests: natural products; bioactive plants; isolation; chromatography and related techniques; structural elucidation; plants under use; bioassays

Dr. Juriyati Jalil

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Centre for Drug and Herbal Development, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz, Kuala Lumpur 50300, Malaysia
Interests: phytochemistry; natural products; anti-inflammatory

Special Issue Information

Dear Colleagues,

Natural products are plants, endophytes, marine organisms that are rich sources of novel therapeutics and are used by old folk of several ethnicities as traditional medicines to alleviate and treat various diseases. Natural products contain unique chemical structures which can be isolated through conventional and advanced chromatographic methods. The structural elucidation of isolated compounds using various spectroscopic techniques should be employed to determine the correct structure which can be further subjected to bioassays.

The bioactive compounds obtained from isolation are usually in small amounts. Hence, compounds could be produced on a large scale via synthetic methods.

Therefore, it is our pleasure to invite researchers from related fields to share your findings and reviews in this Special Issue on “Isolation, Elucidation and Synthesis of Bioactive Natural Products”.

Prof. Dr. Norizan Ahmat
Dr. Juriyati Jalil
Guest Editors

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Keywords

bioactive compounds
natural products
chromatography methods
spectroscopy techniques
structural elucidation
synthesis
bioassay

Published Papers (10 papers)

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Research

10 pages, 1312 KiB

Open AccessArticle

Separation and Isolation of a New Hydroxylated Resveratrol Trimer Together with Other Stilbenoid Compounds from the Lianas of Gnetum microcarpum Blume and Their Inhibitory Effects of Prostaglandin E₂

by Nik Fatini Nik Azmin, Norizan Ahmat, Juriyati Jalil, Carla Wulandari Sabandar, Nik Khairunissa’ Nik Abdullah Zawawi, Siti Norafiqah Mohd Sazali, Mohd Izwan Mohamad Yusof, Aisyah Salihah Kamarozaman and Mulyadi Tanjung

Separations 2023, 10(9), 496; https://doi.org/10.3390/separations10090496 - 12 Sep 2023

Cited by 1 | Viewed by 956

Abstract

A new oligostilbene trimer, malaysianol F (1), together with ten known stilbenes (2–11), were successfully separated and purified from the acetone extract of the lianas of Gnetum microcarpum. Malaysianol D (2) was isolated for the first time in Gnetum plants. The tanninless crude extract (52.5 g) was fractionated using a vacuum liquid chromatography (VLC) technique to give five major fractions. Fraction 2 (4.68 g), 3 (4.79 g) and 4 (9.29 g) were all subjected to further isolation and purification using VLC, column chromatography (CC) and repetitive radial chromatography (RC) techniques with the best solvent system to yield malaysianol F (1) (6.2 mg), malaysianol D (2) (62.5 mg), malaysianol E (3) (2.4 mg), ε-viniferin (4) (10 mg), resveratrol (5) (6.5 mg), gnetol (6) (3.5 mg), gnetucleistol C (7) (12.2 mg), isorhapontigenin (8) (8 mg), cuspidan B (9) (3.2 mg), parvifolol D (10) (4.8 mg) and gnetifolin M (11) (2.5 mg). Their structures were determined on the basis of the analysis of spectral evidence by extensive NMR data analyses and comparison with the related published data. Several compounds were tested for anti-inflammatory activity. Their inhibitory effect on Prostaglandin E₂ (PGE₂) was tested using radioimmunoassay techniques. Compound 6 exhibited significant concentration-dependent inhibitory effects on PGE₂ production with IC₅₀ values of 1.84 µM comparable with the positive control, indomethacin (IC₅₀ 1.29 µM). Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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14 pages, 2350 KiB

Open AccessArticle

New Processes to Extract and Purify Phosvitin by Using Aqueous Salt Solutions, Precipitation and Ultrafiltration Techniques

by Ismael Marcet, Florencia Ridella, Mario Díaz and Manuel Rendueles

Separations 2023, 10(7), 407; https://doi.org/10.3390/separations10070407 - 14 Jul 2023

Viewed by 936

Abstract

Phosvitin is the most phosphorylated naturally occurring protein and it is concentrated in the granular fraction of egg yolk. It has interesting antioxidant and cation chelating properties that can be used to preserve food and cosmetics, but its industrial application is limited as its separation relies on the use of organic solvents and chromatographic techniques, which are expensive and difficult to assimilate in a continuous procedure. In this study, we propose a new phosvitin separation process using substances legally accepted for use in the food industry (NaCl and HCl), employing egg yolk granules as raw material. In this case, the NaCl concentration and the pH of the solution of granules were screened in order to obtain a phosvitin-rich supernatant after centrifugation. Additionally, two new processes were proposed to purify this phosvitin-rich solution. The first was the precipitation of impurities during the desalting stage at optimized pH values. The second was ultrafiltration under selected pH value conditions. A low nitrogen/phosphorous (N/P) atomic ratio is considered a quality parameter, with 3.6 ± 0.2 being the value of the phosvitin-rich supernatant. The two purification processes provided highly purified phosvitin with a similar N/P value of 2.5 ± 0.1. The high level of purification of the phosvitin was confirmed using electrophoresis and ion-exchange chromatography. In particular, the purified phosvitin obtained via ultrafiltration is already desalted and membrane technology is more easily scalable than that based on chromatography, thus facilitating the industrial separation and commercialization of the phosvitin. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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17 pages, 1837 KiB

Open AccessEditor’s ChoiceArticle

Comprehensive Metabolite Fingerprinting of Australian Black and Green Olives and Their Antioxidant and Pharmacokinetics Properties

by Akhtar Ali, Farhad Ahmadi, Jeremy J. Cottrell and Frank R. Dunshea

Separations 2023, 10(6), 354; https://doi.org/10.3390/separations10060354 - 13 Jun 2023

Cited by 4 | Viewed by 1604

Abstract

Polyphenols, especially flavonoids, are well-known for their bioactive antioxidant properties. Therefore, this study aimed to analyze Australian black (ripe) and green olives (unripe) for phenolic and non-phenolic metabolites, antioxidant activities, and pharmacokinetic properties. Liquid chromatography–mass spectrometry coupled with quadrupole–time of flight (LC–ESI–QTOF–MS/MS) was applied to elucidate the composition, identification, and characterization of bioactive metabolites from Australian olives. This study identified 110 metabolites, including phenolic acids, flavonoids, stilbenes, lignans, and other compounds (phenolic terpenes, tyrosols, fatty acids, and terpenoids). Luteolin (flavonoid) and verbascoside (hydroxycinnamic acid) are identified with higher concentrations in black olives. Black (ripe) olives were measured at a higher TPC (10.94 ± 0.42 mg GAE/g) and total antioxidant potential than green olives. The pharmacokinetic properties (absorption, distribution, metabolism, excretion, toxicity) of phenolic compounds for human health were evaluated to predict the potential of the most abundant metabolites in olives. Gastrointestinal absorption and Caco-2 cell permeability of metabolites in olives were also predicted. This study will develop into further research to identify the Australian olives’ therapeutic, nutraceutical, and phytopharmaceutical potential. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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14 pages, 2363 KiB

Open AccessArticle

Antiperspirant and Antibacterial Activities of Curcuma xanthorrhiza Extract as a Potential Alternative Treatment for Hyperhidrosis

by Nurliyana A. M. Sidek, Khairana Husain, Fhataheya Buang and Mazlina Mohd Said

Separations 2023, 10(6), 324; https://doi.org/10.3390/separations10060324 - 25 May 2023

Viewed by 2446

Abstract

Hyperhidrosis is a condition characterized by excessive sweating that affects at least 5% of the world’s population. It is normally associated with unpleasant body odour which requires continuous maintenance throughout life. Antiperspirants and deodorants are the first-line treatments for hyperhidrosis. However, association of this class of product with the risk of other diseases has increased the search for an effective antiperspirant from natural sources. This study aimed to investigate the antibacterial and antiperspirant activities of Curcuma xanthorrhiza Roxb. Using an in vitro microbial assay against specific bacteria responsible for body odour and rat foot pad analysis. Quality control of the fractionated extract was conducted using reversed-phase HPLC based on two active markers: xanthorrhiza and curcumin. Toxicity tests were conducted based on the OECD guidelines (50–2000 mg/kg). Inhibition zone, MIC, and MBC values of the hexane fraction of C. xanthorrhiza showed equivalent antibacterial activity to positive control (p > 0.05). No swelling, redness, or rashes were observed at the injection area throughout the study. Treatment with 40, 80, and 160 mg/kg of the extract significantly decreased the sweat excretion up to 79.34% (p < 0.05) after 15 min compared to negative control. Histopathology analysis showed the reduced size of the secretory units in plantar sweat glands post treatment compared to negative control. In conclusion, the hexane fraction of C. xanthorrhiza is able to reduce sweat excretion in a rat model and inhibit the growth of bacteria causing body odour. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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21 pages, 1253 KiB

Open AccessArticle

Separation, Characterization and Mammal Pancreatic Lipase Inhibitory Potential of Cucumber Flower Flavonoids

by Daniil N. Olennikov

Separations 2023, 10(4), 255; https://doi.org/10.3390/separations10040255 - 16 Apr 2023

Cited by 6 | Viewed by 1507

Abstract

Edible flowers are a new “old” trend in modern gastronomy and healthy nutrition aimed at increasing food attractiveness and improving the consumption of beneficial phytocompounds that have valuable properties. Cucumber (Cucumis sativus L., Cucurbitaceae family) is a well-known agricultural product; it is an important crop that is commonly used across the globe. Despite sufficient knowledge of nutrients and secondary metabolites in cucumber fruits, the use of cucumber flowers for food purposes is still understudied. In this study, the total flavonoid fraction of cucumber flowers was isolated and purified after liquid–liquid and solid-phase extraction and polyamide and Amberlite XAD-2 separation followed by high-performance liquid chromatography with photodiode array detection and electrospray ionization triple quadrupole mass spectrometric detection (HPLC–PDA–ESI–tQ–MS/MS), resulting in the detection of 47 compounds. Identified flavonoids included luteolin, apigenin, and chrysoeriol-based flavones such as C-, O-, and C,O-glycosides, most of which were detected for the first time in C. sativus. Flower extracts from ten cucumber cultivars were quantified, and isoorientin, isoorientin-4′-O-glucoside, and cucumerins B and D were predominant. The use of in vitro assay potential to inhibit mammalian pancreatic lipases was demonstrated for the C. sativus extracts. The dominant compounds were studied separately, and luteolin derivatives were determined to be responsible for the bioactivity. To the best of our knowledge, this is the first study on cucumber flowers that has shown their wide potential for use as a beneficial dietary supplement. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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13 pages, 949 KiB

Open AccessArticle

A Preliminary Cytotoxicity Study of Fagonia arabica against Breast (MCF-7), Oral (KB-3-1), and Lung Cancer (A-549) Cell Lines: A Study Supported by Molecular Marker Analysis Using Dual Staining Dyes

by Ismail A. Walbi, Ali Mohamed Alshabi, Saad Ahmed Alkahtani, Ibrahim Ahmed Shaikh, Basel A. Abdel-Wahab, Masood Medleri Khateeb, Mohammed Shafiuddin Habeeb, Mohamed A. A. Orabi, Arun K. Shettar and Joy H. Hoskeri

Separations 2023, 10(2), 110; https://doi.org/10.3390/separations10020110 - 3 Feb 2023

Cited by 2 | Viewed by 2863

Abstract

Aim: The objective of this research is to present a phytochemical profile of Fagonia arabica and to investigate the cytotoxic potential of its extracts against breast, oral, and lung cancer cell lines using MTT assay and dual staining-based mechanistic analysis. Methods: The progressive extraction of F. arabica was carried out using the Soxhlet extraction technique. The total phenolic and flavonoid content was calculated as part of the phytochemical profiling performed using GCMS and LCMS methods. The MTT assay was utilized to assess the cytotoxicity against normal L929 cells, as well as malignant A549, MCF-7, and KB-3-1cell lines. Results: The phenolic compounds and flavonoids were the two main elements of the F. arabica methanolic extract, with 1323 µg GAE/g of dry weight and 523.07 µg QE/g of dry weight, respectively. The presence of the functional phytochemicals was verified by GCMS and LCMS analyses. Toxicity testing on the L929 cell line found that the F. arabica methanol extract was the least harmful, with the highest IC₅₀ (296.11 µg/mL). The MTT assay for cell viability against MCF-7 and KB-3-1 yielded significant results, with IC₅₀ values of 135.02 µg/mL and 195.21 µg/mL, respectively. The aqueous extract exhibited significant cytotoxicity against the A549 cell lines (IC₅₀ 116.06 µg/mL). The molecular marker analyses using dual staining revealed that the methanolic extract successfully triggered apoptosis in the different cancer cells tested. Conclusion: The present data suggest that the methanol extract of F. arabica has substantial cytotoxic action against lung, breast, and oral cancer cell lines. Thus, F. Arabica would be a promising source of anticancer medicines, warranting more research to identify the lead molecules with anticancer properties. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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15 pages, 2219 KiB

Open AccessArticle

Isolation and Characterization of Compounds from Ochreinauclea maingayi (Hook. f.) Ridsd. (Rubiaceae) with the Aid of LCMS/MS Molecular Networking

by Norfaizah Osman, Azeana Zahari, Hazrina Hazni, Wan Nurul Nazneem Wan Othman, Nurulfazlina Edayah Rasol, Nor Hadiani Ismail, Pierre Champy, Mehdi A. Beniddir, Marc Litaudon and Khalijah Awang

Separations 2023, 10(2), 74; https://doi.org/10.3390/separations10020074 - 21 Jan 2023

Viewed by 1634

Abstract

Phytochemical investigation of the dichloromethane crude extract from the bark of Ochreinauclea maingayi with the aid of LCMS/MS-based molecular networking guided the isolation and accelerated the elucidation of known and new indole alkaloids. The molecular networking analysis produces two main clusters, along with 41 non-prioritized clusters and self-loop nodes. Each cluster has several nodes which depict the fractions contained within those nodes. An implementation of a fraction mapping for each node represents the molecular weight and key fragment data of each compound. From the analysis of each cluster and node, we can deduce the indole alkaloids are the scaffold of interest. Indole scaffold can be found between F5 and F10 that contain several types of indole alkaloids. In total, we have successfully purified nine indole alkaloids, including 9H-β-carboline-4-carboxylate 2, norharmane 3, harmane 4, naucledine 10, neonaucline 15, 1,2,3,4-tetranorharmane-1-one 16, naulafine 19, cadambine 9, and a new monoterpene indole alkaloid dihyrodeglycocadambine 7 from F5 to F10 using a chromatographic technique. Their structures were confirmed by 1D-NMR, 2D-NMR, UV, IR, LCMS, and MS2LDA. Several clusters and nodes contain ions that could not be annotated, suggesting that they may possess novel compounds that are yet to be discovered. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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21 pages, 3086 KiB

Open AccessArticle

Apoptotic Cell Death via Activation of DNA Degradation, Caspase-3 Activity, and Suppression of Bcl-2 Activity: An Evidence-Based Citrullus colocynthis Cytotoxicity Mechanism toward MCF-7 and A549 Cancer Cell Lines

by Ibrahim Ahmed Shaikh, Ali Mohamed Alshabi, Saad Ahmed Alkahtani, Mohamed A. A. Orabi, Basel A. Abdel-Wahab, Ismail A. Walbi, Mohammed Shafiuddin Habeeb, Masood Medleri Khateeb, Arun K. Shettar and Joy H. Hoskeri

Separations 2022, 9(12), 411; https://doi.org/10.3390/separations9120411 - 5 Dec 2022

Cited by 4 | Viewed by 1645

Abstract

The objectives of this study are to investigate the cytotoxic effect of different Citrullus colocynthis extracts on breast and lung cancer cell lines using flow cytometry to gain mechanistic insights. C. colocynthis was extracted sequentially using the Soxhlet method. We first tested the plant extracts’ cytotoxicity on non-malignant L929 cells and cancerous breast (MCF-7) and lung (A549) cell lines. We observed that the IC₅₀ of the methanol extract on the viability of MCF-7 and A549 cell lines was 81.08 µg/mL and 17.84 µg/mL, respectively, using the MTT assay. The aqueous and methanol extracts were less toxic when tested against the non-cancerous L929 cell line, with IC₅₀ values of 235.48 µg/mL and 222.29 µg/mL, respectively. Then, using flow cytometry, we investigated the underlying molecular pathways with Annexin-V, Anti-Bcl-2, Caspase-3, and DNA fragmentation (TUNEL) assays. Flow cytometric and molecular marker analyses revealed that the methanol extract activated caspase-3 and inhibited Bcl-2 protein, causing early and late apoptosis, as well as cell death via DNA damage in breast and lung cancer cells. These findings indicate that the methanol extract of C. colocynthis is cytotoxic to breast and lung cancer cell lines. The total phenolic and flavonoid content analysis results showed the methanolic extract of C. colocynthis has a concentration of 326.25 μg GAE/g dwt and 274.61 μg QE/g dwt, respectively. GC-MS analysis of the methanol extract revealed phytochemicals relevant to its cytotoxicity. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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18 pages, 1646 KiB

Open AccessArticle

Tribulus terrestris Cytotoxicity against Breast Cancer MCF-7 and Lung Cancer A549 Cell Lines Is Mediated via Activation of Apoptosis, Caspase-3, DNA Degradation, and Suppressing Bcl-2 Activity

by Ali Mohamed Alshabi, Saad Ahmed Alkahtani, Ibrahim Ahmed Shaikh, Mohamed A. A. Orabi, Basel A. Abdel-Wahab, Ismail A. Walbi, Mohammed Shafiuddin Habeeb, Masood Medleri Khateeb, Arun K. Shettar and Joy H. Hoskeri

Separations 2022, 9(11), 383; https://doi.org/10.3390/separations9110383 - 21 Nov 2022

Viewed by 2059

Abstract

The primary objective of this research was to use flow cytometry to gain mechanistic insights into the cytotoxic effects of Tribulus terrestris extracts on breast cancer (MCF7) and lung cancer (A549) cell lines. T. terrestris was extracted using a Soxhlet apparatus in a progressive process. GC–MS was used to establish the phytochemical constituents. The amounts of phenolic compounds and flavonoids in the plant extracts were calculated using spectrophotometric analysis. The cytotoxicity of plant extracts was initially evaluated in non-malignant L929 cells, then in carcinogenic MCF-7 and A549 cell lines. Then, we performed an Annexin V assay, an anti-Bcl-2 assay, a Caspase-3 assay, and a DNA fragmentation (TUNEL) assay, using flow cytometry to investigate the underlying molecular processes. Based on the data, the methanolic extract of T. terrestris contained the highest amounts of phenolic compounds and flavonoids, with values of 169.87 µg GAE/g dwt and 160.12 µg QE/g dwt, respectively. Analysis by GC–MS revealed the presence of bioactive phytochemicals with proven cytotoxicity. Based on the MTT experiment, we determined that the IC₅₀ values for the methanol extract’s effect on the viability of the MCF-7 and A549 cell lines were 218.19 and 179.62 µg/mL, respectively. The aqueous and methanol extracts were less cytotoxic when tested against the cancer-free L929 cell line (IC₅₀ = 224.35 µg/mL). In both breast and lung cancer cells, the methanolic extract was found to activate caspase-3 and inhibit the Bcl-2 protein, resulting in early and late apoptosis and cell death via DNA damage. These findings point to cytotoxic effects of T. terrestris methanol extract against breast and lung cancer cell lines. Due to its potential as a source of anti-cancer chemotherapeutic medicines, T. terrestris warrants further investigation. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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16 pages, 2199 KiB

Open AccessArticle

Anti-Allergic and Antioxidant Potential of Polyphenol-Enriched Fractions from Cyclopia subternata (Honeybush) Produced by a Scalable Process

by Carla Dippenaar, Hitoshi Shimbo, Kazunobu Okon, Neil Miller, Elizabeth Joubert, Tadashi Yoshida and Dalene de Beer

Separations 2022, 9(10), 278; https://doi.org/10.3390/separations9100278 - 1 Oct 2022

Cited by 3 | Viewed by 1796

Abstract

Anti-allergic activity was previously demonstrated for extracts of Cyclopia subternata Vogel plant material, containing substantial amounts of xanthones, benzophenones, dihydrochalcones, flavanones and flavones. Fractionation of a hot water extract on macroporous resin was performed aiming to increase its potency. Operating conditions for scaled-up fractionation of the extract were determined, using small-scale static and dynamic sorption/desorption experiments. The anti-allergic potential of the fractions was assessed based on inhibition of β-hexosaminidase release from IgE-sensitized RBL-2H3 cells. Given the role of oxidative stress in allergic reactions, the extract and fractions were also tested for their ability to scavenge the superoxide anion radical and inhibit xanthine oxidase (XO), an enzyme involved in its generation. The routine DPPH and ORAC assays were used for determination of the antioxidant capacity of the fractions. 3-β-D-Glucopyranosyl-4-O-β-D-glucopyranosyliriflophenone (IDG) had the lowest affinity for the resin, dictating selection of the optimal separation conditions. The extract was separated into four fractions on XAD1180N, using step-wise gradient elution with EtOH-water solutions. The major phenolic compounds present in the fractions were IDG and 3-β-D-glucopyranosyliriflophenone (fraction 1), mangiferin, isomangiferin, 3′,5′-di-β-D-glucopyranosyl-3-hydroxyphloretin and vicenin-2 (fraction 2), 3′,5′-di-β-D-glucopyranosylphloretin, eriocitrin and scolymoside (fraction 3) and hesperidin and p-coumaric acid (fraction 4). Fractionation was only partially effective in increasing activity compared to the extract, i.e., fractions 2, 3 and 4 in the DPPH^• and XO assays, fractions 1 and 2 in the ORAC assay and fraction 1 in the β-hexosaminidase release assay. In vivo testing will be required to determine whether the increased activity of fractions is worth the effort and expense of fractionation. Full article

(This article belongs to the Special Issue Isolation, Elucidation and Synthesis of Bioactive Natural Products)

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