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Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 43450

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Prof. Dr. Junho Kim

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Department of Food Science and Biotechnology, Andong National University, 1375 Gyeongdong-ro, Andong 36729, Republic of Korea
Interests: phytochemicals; phytoestrogens; metabolic disorders; glucose homeostasis; inflammation

Special Issue Information

Dear Colleagues,

Naturally occurring bioactive phytochemicals provide unlimited opportunities for the development of novel functional food and drugs. Numerous studies have demonstrated that phytochemicals could become safe and effective alternatives for synthetic medicines. This Special Issue aims to cover the most up-to-date studies on extraction methods, analysis and biological activities of natural compounds or extracts in the research field of plant science, food science, pharmacology and biotechnology. We also welcome review articles that summarize the latest research on this topic.

Possible topics include, but are not limited to:

A novel method to enhance extraction efficiency of bioactive phytochemicals
Analytical data of bioactive compounds in promising medicinal plants
The effects and molecular mechanisms of phytochemicals in inflammation and metabolic disorders
Phytoestrogens and their action mode in the prevention of postmenopausal diseases

Prof. Dr. Junho Kim
Guest Editor

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Keywords

natural products
bioactive compounds
extraction
bioactivities
metabolic disorders
analytical data
phytoestrogens

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Related Special Issue

Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products—Second Edition in Molecules (2 articles)

Published Papers (10 papers)

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Research

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16 pages, 1805 KiB

Open AccessArticle

Bioassay-Guided Assessment of Antioxidative, Anti-Inflammatory and Antimicrobial Activities of Extracts from Medicinal Plants via High-Performance Thin-Layer Chromatography

by Marko D. Jović, Snezana Agatonovic-Kustrin, Petar M. Ristivojević, Jelena Đ. Trifković and David W. Morton

Molecules 2023, 28(21), 7346; https://doi.org/10.3390/molecules28217346 - 30 Oct 2023

Cited by 6 | Viewed by 3133

Abstract

Natural products and their analogues have contributed significantly to treatment options, especially for anti-inflammatory and infectious diseases. Thus, the primary objective of this work was to compare the bioactivity profiles of selected medicinal plants that are historically used in folk medicine to treat inflammation and infections in the body. Chemical HPTLC fingerprinting was used to assess antioxidant, phenolic and flavonoid content, while bioassay-guided HPTLC was used to detect compounds with the highest antibacterial and anti-inflammatory activities. The results of this study showed that green tea leaf, walnut leaf, St. John’s wort herb, wild thyme herb, European goldenrod herb, chamomile flower, and immortelle flower extracts were strong radical scavengers. Green tea and nettle extracts were the most active extracts against E. coli, while calendula flower extract showed significant potency against S. aureus. Furthermore, green tea, greater celandine, and fumitory extracts exhibited pronounced potential in suppressing COX-1 activity. The bioactive compounds from the green tea extract, as the most bioactive, were isolated by preparative thin-layer chromatography and characterized with their FTIR spectra. Although earlier studies have related green tea’s anti-inflammatory properties to the presence of catechins, particularly epigallocatechin-3-gallate, the FTIR spectrum of the compound from the most intense bioactive zone showed the strongest anti-inflammatory activity can be attributed to amino acids and heterocyclic compounds. As expected, antibacterial activity in extracts was related to fatty acids and monoglycerides. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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15 pages, 18642 KiB

Open AccessArticle

In Vitro and In Vivo Anti-Inflammatory Effects of Cannabidiol Isolated from Novel Hemp (Cannabis sativa L.) Cultivar Pink Pepper

by Jong-Hui Kim, Min Hong, Joon-Hee Han, Byeong Ryeol Ryu, Young Seok Lim, Jung Dae Lim, Chang Hyeug Kim, Soo-Ung Lee and Tae-Hyung Kwon

Molecules 2023, 28(18), 6439; https://doi.org/10.3390/molecules28186439 - 5 Sep 2023

Cited by 1 | Viewed by 2468

Abstract

Cannabis sativa L. contains more than 80 cannabinoids, among which cannabidiol (CBD) is the main neuroactive component. We aimed to investigate the anti-inflammatory efficacy of CBD in vitro and in vivo isolated from “Pink pepper”, a novel hemp cultivar, by repeating the method of selecting and cultivating individuals with the highest CBD content. We investigated the effects of CBD on inflammatory markers elevated by lipopolysaccharide (LPS) treatment in RAW 264.7 mouse macrophage cells through Western blot and RT-PCR. In addition, we confirmed these effects through the ELISA of inflamed paw tissue of a λ-carrageenan-induced mouse edema model that received an oral administration of CBD. CBD inhibited the LPS-induced phosphorylation of NF-κB and MAPK in RAW 264.7 and exhibited anti-inflammatory effects by participating in these pathways. In our in vivo study, we confirmed that CBD also inhibited the inflammatory mediators of proteins extracted from edematous mouse paw tissue. These results show that CBD isolated from “Pink pepper” exhibits potent anti-inflammatory effects. These anti-inflammatory effects of CBD have pharmacological and physiological significance, highlighting the industrial value of this novel cultivar. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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13 pages, 1842 KiB

Open AccessArticle

Ex Vivo Antiplatelet and Thrombolytic Activity of Bioactive Fractions from the New-Fangled Stem Buds of Ficus religiosa L. with Simultaneous GC-MS Examination

by Sunil Kumar, Muhammad Arif, Mehnaz Kamal, Talha Jawaid, Mohammed Moizuddin Khan, Beenish Mukhtar, Abdullah Khan, Saif Ahmed, Saud M. AlSanad and Osama A. Al-Khamees

Molecules 2023, 28(9), 3918; https://doi.org/10.3390/molecules28093918 - 5 May 2023

Cited by 5 | Viewed by 1836

Abstract

Different parts of Ficus religiosa are the common components of various traditional formulations for the treatment of several blood disorders. The new-fangled stem buds’ powder was extracted with 80% ethanol and successively fractionated by chloroform and methanol. Chloroform and methanol fractions of Ficus religiosa (CFFR and MFFR) were tested for antiplatelet, antithrombotic, thrombolytic, and antioxidant activity in ex vivo mode. The MFFR was particularly investigated for GC-MS and toxicity. The antiplatelet activity of the CFFR, MFFR, and standard drug aspirin at 50 μg/mL was 54.32%, 86.61%, and 87.57%, and a significant delay in clot formation was noted. CFFR at different concentrations did not show a significant effect on the delay of clot formation, antiplatelet, and free radical scavenging activity. The most possible marker compounds for antiplatelet and antioxidant activity identified by GC-MS in the MFFR are salicylate derivatives aromatic compounds such as benzeneacetaldehyde (7), phenylmalonic acid (13), and Salicylic acid (14), as well as Benzamides derivatives such as carbobenzyloxy-dl-norvaline (17), 3-acetoxy-2(1H)-pyridone (16), and 3-benzylhexahydropyrrolo [1,2-a] pyrazine-1,4-dione (35). A toxicity study of MFFR did not show any physical indications of toxicity and mortality up to 1500 mg/kg body weight and nontoxic up to 1000 mg/kg, which is promising for the treatment of atherothrombotic diseases. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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14 pages, 3043 KiB

Open AccessArticle

Protective Effects of Hemp (Cannabis sativa) Root Extracts against Insulin-Deficient Diabetes Mellitus In Mice

by Yujeong Kim, Wonhee Kim, Soo-Hyun Kim, Kyu-Sang Sim, Ki-Hyun Kim, Kiu-Hyung Cho, Gi-Seok Kwon, Jung-Bok Lee and Jun-Ho Kim

Molecules 2023, 28(9), 3814; https://doi.org/10.3390/molecules28093814 - 29 Apr 2023

Cited by 7 | Viewed by 2794

Abstract

The pharmacological potential of industrial hemp (Cannabis sativa) has been widely studied. However, the majority of studies have focused on cannabidiol, isolated from the inflorescence and leaf of the plant. In the present study, we evaluated the anti-diabetic potential of hemp root water (HWE) and ethanol extracts (HEE) in streptozotocin (STZ)-induced insulin-deficient diabetic mice. The administration of HWE and HEE ameliorated hyperglycemia and improved glucose homeostasis and islet function in STZ-treated mice (p < 0.05). HWE and HEE suppressed β-cell apoptosis and cytokine-induced inflammatory signaling in the pancreas (p < 0.05). Moreover, HWE and HEE normalized insulin-signaling defects in skeletal muscles and apoptotic response in the liver and kidney induced by STZ (p < 0.05). Gas chromatography-mass spectrometry analysis of HWE and HEE showed possible active compounds which might be responsible for the observed anti-diabetic potential. These findings indicate the possible mechanisms by which hemp root extracts protect mice against insulin-deficient diabetes, and support the need for further studies geared towards the application of hemp root as a novel bioactive material. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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11 pages, 2085 KiB

Open AccessFeature PaperArticle

Glochodpurnoid B from Glochidion puberum Induces Endoplasmic Reticulum Stress-Mediated Apoptosis in Colorectal Cancer Cells

by Yang Tian, Runzhu Fan, Zhao Yin, Yongping Huang, Dong Huang, Fangyu Yuan, Aiping Yin, Guihua Tang, Rong Pu and Sheng Yin

Molecules 2023, 28(2), 511; https://doi.org/10.3390/molecules28020511 - 4 Jan 2023

Cited by 1 | Viewed by 1856

Abstract

Glochidpurnoids A and B (1 and 2), two new coumaroyl or feruloyl oleananes, along with 17 known triterpenoids (3–19) were obtained from the stems and twigs of Glochidion puberum. Their structures were elucidated by extensive spectroscopic data analyses, chemical methods, and single crystal X-ray diffraction. All compounds were screened for cytotoxicity against the colorectal cancer cell line HCT-116, and 2, 3, 5, 6, 11, and 17 showed remarkable inhibitory activities (IC₅₀: 0.80–2.99 μM), being more active than the positive control 5-fluorouracil (5-FU). The mechanistic study of 2, the most potent compound, showed that it could induce endoplasmic reticulum (ER) stress-mediated apoptosis and improve the sensitivity of HCT-116 cells to 5-FU. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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11 pages, 1226 KiB

Open AccessArticle

Dammarane-Type Triterpenoid from the Stem Bark of Aglaia elliptica (Meliaceae) and Its Cytotoxic Activities

by Kindi Farabi, Desi Harneti, Darwati, Tri Mayanti, Nurlelasari, Rani Maharani, Aprilia Permata Sari, Tati Herlina, Ace Tatang Hidayat, Unang Supratman, Sofa Fajriah, Mohamad Nurul Azmi and Yoshihito Shiono

Molecules 2022, 27(19), 6757; https://doi.org/10.3390/molecules27196757 - 10 Oct 2022

Cited by 8 | Viewed by 2377

Abstract

Two new dammarane-type triterpenoid fatty acid ester derivatives, 3β-oleate-20S-hydroxydammar-24-en (1) and 3β-oleate-20S,24S-epoxy-25-hydroxydammarane (2) with a known dammarane-type triterpenoid compound, such as 20S-hydroxydammar-24-en-3-on (3), were isolated from the stem bark of Aglaiaelliptica (C.DC.) Blume. The chemical structures were determined by spectroscopic methods, including FTIR, NMR (one and two-dimensional), and HRESITOF-MS analysis, as well as chemical derivatization and comparison with previous literature. Furthermore, the synthetic analog resulting from transesterification of 1 and 2 also obtained 3β,20S-dihydroxy-dammar-24-en (4) and 20S,24S-epoxy-3β,25-dihydroxydammarane (5), respectively. The cytotoxic effect of all isolated and synthetic analog compounds was evaluated using PrestoBlue reagent against MCF-7 breast cancer cell and B16-F10 melanoma cell lines. The 20S-hydroxydammar-24-en-3-on (3) showed the strongest activity against MCF-7 breast cancer and B16-F10 melanoma cell, indicating that the ketone group at C-3 in 3 plays an essential role in the cytotoxicity of dammarane-type triterpenoid. On the other hand, compounds 1 and 2 had very weak cytotoxic activity against the two cell lines, indicating the presence of fatty acid, significantly decreasing cytotoxic activity. This showed the significance of the discovery to investigate the essential structural feature in dammarane-type triterpenoid, specifically for the future development of anticancer drugs. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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11 pages, 2451 KiB

Open AccessArticle

Canavalia gladiata Pod Extract Mitigates Ovalbumin-Induced Asthma Onset in Male BALB/c Mice via Suppression of MAPK

by Wen Yan Huang, Sang Hoon Lee, Seong Ju Oh, Hyeock Yoon, Jeong Hoon Pan, Inhye Jeong, Mi Jeong Kim, Bok Kyung Han, Jae Kyeom Kim, Eui-Cheol Shin and Young Jun Kim

Molecules 2022, 27(19), 6317; https://doi.org/10.3390/molecules27196317 - 25 Sep 2022

Cited by 2 | Viewed by 2124

Abstract

Asthma is one of the most common inflammatory diseases of the lung worldwide. There has been considerable progress in recent studies to treat and prevent allergic asthma, however, various side effects are still observed in clinical practice. Six-week-old male BALB/c mice were orally administered with either sword bean pod extracts (SBP; 100 or 300 mg/kg) or dexamethasone (DEX; 5 mg/kg) once daily over 3 weeks, followed by ovalbumin sensitization (OVA/Alum.; intraperitoneal administration, 50 μg/2 mg/per mouse). Scoring of lung inflammation was performed to observe pathological changes in response to SBP treatment compared to OVA/Alum.-induced lung injury. Additionally, inflammatory cytokines were quantified in serum, bronchoalveolar lavage fluid (BALF), and lung tissue using ELISA and Western blot analyses. SBP treatment significantly reduced the infiltration of inflammatory cells, and release of histamine, immunoglobulin E, and leukotriene in serum and BALF. Moreover, the therapeutic effect of SBP was also assessed to analyze the inflammatory changes in the lung tissues. SBP markedly suppressed the activation of the MAPK signaling pathway and the expression of key inflammatory proteins (e.g., TNF-α) and Th2 type cytokines (IL-5 and IL-13). SBP was effective in ameliorating the allergic inflammation against OVA/Alum.-induced asthma by suppressing pulmonary inflammation. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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Review

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24 pages, 1477 KiB

Open AccessReview

Plant-Derived Compounds and Extracts as Modulators of Plasmin Activity—A Review

by Joanna Kolodziejczyk-Czepas and Jan Czepas

Molecules 2023, 28(4), 1677; https://doi.org/10.3390/molecules28041677 - 9 Feb 2023

Cited by 1 | Viewed by 3157

Abstract

Functionality of the fibrinolytic system is based on activity of its central enzyme, plasmin, responsible for the removal of fibrin clots. Besides the hemostasis, fibrinolytic proteins are also involved in many other physiological and pathological processes, including immune response, extracellular matrix degradation, cell migration, and tissue remodeling. Both the impaired and enhanced activity of fibrinolytic proteins may result in serious physiological consequences: prothrombotic state or excessive bleeding, respectively. However, current medicine offers very few options for treating fibrinolytic disorders, particularly in the case of plasmin inhibition. Although numerous attempts have been undertaken to identify natural or to develop engineered fibrinolytic system modulators, structural similarities within serine proteases of the hemostatic system and pleiotropic activity of fibrinolytic proteins constitute a serious problem in discovering anti- or profibrinolytic agents that could precisely affect the target molecules and reduce the risk of side effects. Therefore, this review aims to present a current knowledge of various classes of natural inhibitors and stimulators of the fibrinolytic system being well-defined low-molecular plant secondary metabolites or constituents of plant extracts as well as plant peptides. This work also discusses obstacles caused by low specificity of most of natural compounds and, hence, outlines recent trends in studies aimed at finding more efficient modulators of plasmin activity, including investigation of modifications of natural pharmacophore templates. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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25 pages, 2379 KiB

Open AccessReview

Current Landscape of Methods to Evaluate Antimicrobial Activity of Natural Extracts

by Rebeca Gonzalez-Pastor, Saskya E. Carrera-Pacheco, Johana Zúñiga-Miranda, Cristina Rodríguez-Pólit, Arianna Mayorga-Ramos, Linda P. Guamán and Carlos Barba-Ostria

Molecules 2023, 28(3), 1068; https://doi.org/10.3390/molecules28031068 - 20 Jan 2023

Cited by 22 | Viewed by 11065

Abstract

Natural extracts have been and continue to be used to treat a wide range of medical conditions, from infectious diseases to cancer, based on their convenience and therapeutic potential. Natural products derived from microbes, plants, and animals offer a broad variety of molecules and chemical compounds. Natural products are not only one of the most important sources for innovative drug development for animal and human health, but they are also an inspiration for synthetic biology and chemistry scientists towards the discovery of new bioactive compounds and pharmaceuticals. This is particularly relevant in the current context, where antimicrobial resistance has risen as a global health problem. Thus, efforts are being directed toward studying natural compounds’ chemical composition and bioactive potential to generate drugs with better efficacy and lower toxicity than existing molecules. Currently, a wide range of methodologies are used to analyze the in vitro activity of natural extracts to determine their suitability as antimicrobial agents. Despite traditional technologies being the most employed, technological advances have contributed to the implementation of methods able to circumvent issues related to analysis capacity, time, sensitivity, and reproducibility. This review produces an updated analysis of the conventional and current methods to evaluate the antimicrobial activity of natural compounds. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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17 pages, 1065 KiB

Open AccessReview

Applications of Essential Oils and Plant Extracts in Different Industries

by Parisa Bolouri, Robab Salami, Shaghayegh Kouhi, Masoumeh Kordi, Behnam Asgari Lajayer, Javad Hadian and Tess Astatkie

Molecules 2022, 27(24), 8999; https://doi.org/10.3390/molecules27248999 - 16 Dec 2022

Cited by 84 | Viewed by 11319

Abstract

Essential oils (EOs) and plant extracts are sources of beneficial chemical compounds that have potential applications in medicine, food, cosmetics, and the agriculture industry. Plant medicines were the only option for preventing and treating mankind’s diseases for centuries. Therefore, plant products are fundamental sources for producing natural drugs. The extraction of the EOs is the first important step in preparing these compounds. Modern extraction methods are effective in the efficient development of these compounds. Moreover, the compounds extracted from plants have natural antimicrobial activity against many spoilage and disease-causing bacteria. Also, the use of plant compounds in cosmetics and hygiene products, in addition to their high marketability, has been helpful for many beauty problems. On the other hand, the agricultural industry has recently shifted more from conventional production systems to authenticated organic production systems, as consumers prefer products without any pesticide and herbicide residues, and certified organic products command higher prices. EOs and plant extracts can be utilized as ingredients in plant antipathogens, biopesticides, and bioherbicides for the agricultural sector. Considering the need and the importance of using EOs and plant extracts in pharmaceutical and other industries, this review paper outlines the different aspects of the applications of these compounds in various sectors. Full article

(This article belongs to the Special Issue Extraction, Analysis and Biological Activity Studies of Compounds from Natural Products)

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