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Natural Products from Plant: From Determination to Application

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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 August 2024) | Viewed by 16282

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Dr. Guoxu Ma

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Guest Editor

Institute of Medicinal Plant Development, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100193, China
Interests: active components; structure elucidation; structure analysis; bioactive natural products; analysis of active ingredients;efficacy of natural products; development and application of natural products

Special Issue Information

Dear Colleagues,

The determination and application of natural products from plants have always been concerned and attracted by scholars, especially in the discovery of active natural products, using interdisciplinary methods such as activity tracking and gene mining, which can promote the rapid development of natural products.

It is undeniable that there are a large number of natural products in plants. Although the content of many components is low, their activity is significant. Therefore, the detection and analysis of active natural products are very important. In addition, the screening and analysis of some active components can speed up the discovery of natural products. We still have a lot work to do on the determination and application of natural products.

The Special Issue “Natural Products from Plant: From Determination to Application” aims to present the most recent achievements in natural products, especially in discovery, analysis and application of natural products. Manuscripts, together with review papers, will summarize the important advances of natural products found in the plants.

Dr. Guoxu Ma
Guest Editor

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Keywords

active components
structure elucidation
structure analysis
bioactive natural products
analysis of active ingredients
efficacy of natural products
development and application of natural products

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Published Papers (9 papers)

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Research

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21 pages, 4104 KiB

Open AccessArticle

Optimization of Ultrasonic-Assisted Extraction, Characterization and Antioxidant and Immunoregulatory Activities of Arthrospira platensis Polysaccharides

by Na Wang, Jingyi Qin, Zishuo Chen, Jiayi Wu and Wenzhou Xiang

Molecules 2024, 29(19), 4645; https://doi.org/10.3390/molecules29194645 - 30 Sep 2024

Viewed by 1063

Abstract

This study aimed to enhance the ultrasonic-assisted extraction (UAE) yield of seawater Arthrospira platensis polysaccharides (APPs) and investigate its structural characteristics and bioactivities. The optimization of UAE achieved a maximum crude polysaccharides yield of 14.78%. The optimal extraction conditions were a liquid–solid ratio of 30.00 mL/g, extraction temperature of 81 °C, ultrasonic power at 92 W and extraction time at 30 min. After purification through cellulose DEAE-52 and Sephadex G-100 columns, two polysaccharide elutions (APP-1 and APP-2) were obtained. APP-2 had stronger antioxidant and immunoregulatory activities than APP-1, thus the characterization of APP-2 was conducted. APP-2 was an acidic polysaccharide consisting of rhamnose, glucose, mannose and glucuronic acid at a ratio of 1.00:24.21:7.63:1.53. It possessed a molecular weight of 72.48 kDa. Additionally, APP-2 had linear and irregular spherical particles and amorphous structures, which contained pyranoid polysaccharides with alpha/beta glycosidic bonds. These findings offered the foundation for APP-2 as an antioxidant and immunomodulator applied in the food, pharmaceutical and cosmetic industries. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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13 pages, 1427 KiB

Open AccessArticle

Free Radical Scavenging Effect and Immunomodulatory Activity of Total Saponins Extract of Ginseng Fibrous Roots

by Peng Zhang, Dongyan Zhang, Chuanjie Ma, Ruxia Wang and Weili Wang

Molecules 2024, 29(12), 2770; https://doi.org/10.3390/molecules29122770 - 11 Jun 2024

Cited by 1 | Viewed by 1052

Abstract

Ginseng (Panax ginseng C.A. Mey) is known for its rich saponin compounds and tonic effects. To better utilize the medicinal value of ginseng, this study investigated the extraction process, components, free radical scavenging ability, and immunomodulatory activity of total saponins of ginseng fibrous roots. The response surface methodology was employed to optimize the extraction process of total saponins, and Q-Orbitrap high-resolution liquid chromatography–mass spectrometry (LC-MS) was used to identify the chemical constituents in the total saponins extract of ginseng fibrous roots (GRS). The results showed that the optimal extraction process was achieved with an ethanol concentration of 68%, a material–solvent ratio of 1:25 mL/g, and an extraction time of 20 min, yielding a total saponin content of 6.34% under these conditions. The extract contained four terpenoid compounds and four polyphenolic compounds. GRS exhibited considerable scavenging activity against DPPH and ABTS radicals, with IC₅₀ values of 0.893 and 0.210 mg/mL, respectively. Moreover, GRS restored immune suppression in mice by increasing white blood cell, red blood cell, and neutrophil counts, and improving the lymphocyte. It also promoted immune system recovery, as evidenced by elevated serum levels of IL-2, IFN-γ, TNF-α, and IL-1β in mice. GRS is a natural compound with promising potential for developing antioxidants and immunomodulatory foods. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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34 pages, 11472 KiB

Open AccessArticle

Unveiling the Chemical Composition of Sulfur-Fumigated Herbs: A Triple Synthesis Approach Using UHPLC-LTQ-Orbitrap MS—A Case Study on Steroidal Saponins in Ophiopogonis Radix

by Yanan Li, Pingping Dong, Zhanpeng Shang, Long Dai, Shaoping Wang and Jiayu Zhang

Molecules 2024, 29(3), 702; https://doi.org/10.3390/molecules29030702 - 2 Feb 2024

Viewed by 1324

Abstract

Ophiopogonis Radix (OR) is a traditional Chinese medicine. In recent years, in order to achieve the purpose of drying, bleaching, sterilizing and being antiseptic, improving appearance, and easy storage, people often use sulfur fumigation for its processing. However, changes in the chemical composition of medicinal herbs caused by sulfur fumigation can lead to the transformation and loss of potent substances. Therefore, the development of methods to rapidly reveal the chemical transformation of medicinal herbs induced by sulfur fumigation can guarantee the safe clinical use of medicines. In this study, a combined full scan-parent ions list-dynamic exclusion acquisition-diagnostic product ions analysis strategy based on UHPLC-LTQ-Orbitrap MS was proposed for the analysis of steroidal saponins and their transformed components in sulfur-fumigated Ophiopogonis Radix (SF-OR). Based on precise mass measurements, chromatographic behavior, neutral loss ions, and diagnostic product ions, 286 constituents were screened and identified from SF-OR, including 191 steroidal saponins and 95 sulfur-containing derivatives (sulfates or sulfites). The results indicated that the established strategy was a valuable and effective analytical tool for comprehensively characterizing the material basis of SF-OR, and also provided a basis for potential chemical changes in other sulfur-fumigated herbs. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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8 pages, 1590 KiB

Open AccessArticle

Skeleton Synthesis of a Plant-Derived Radioprotective Alkaloid Born to Produce a Novel Fused Heterocycle

by Sifan Liu, Huiling Gu, Kai Liang, Zhenzhen Wei, Bin Li, Ying Tian, Ruihong Li, Guangjie Zhang and Shuchen Liu

Molecules 2023, 28(9), 3829; https://doi.org/10.3390/molecules28093829 - 30 Apr 2023

Viewed by 1475

Abstract

Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of Orychophragmus violaceus was identified as bearing a novel skeleton and proved to have an excellent radioprotective effect. Different from the common alkaloid structure, the main block of orychophragine D is constructed of an oxotriazine and an oxopiperazine, which are connected in parallel by a C-N bond. In this paper, a preparation method for the novel heterocycle skeleton of orychophragine D is proposed for the first time. N-Boc-L-serine was utilized as the original material to complete the preparation with 11 steps in a 13% overall yield. A hydroxyl group was established on the side chain of the skeleton as the reaction site for researchers to conduct further structural modification or derivatization. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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21 pages, 2397 KiB

Open AccessArticle

Stabilization of Sunflower Oil with Biologically Active Compounds from Berries

by Aliona Ghendov-Mosanu, Violina Popovici, Cristina Gabriela Constantinescu (Pop), Olga Deseatnicova, Rodica Siminiuc, Iurie Subotin, Raisa Druta, Adela Pintea, Carmen Socaciu and Rodica Sturza

Molecules 2023, 28(8), 3596; https://doi.org/10.3390/molecules28083596 - 20 Apr 2023

Cited by 4 | Viewed by 1789

Abstract

Sunflower oil (Helianthus annuus) contains a rich concentration of polyunsaturated fatty acids, which are susceptible to rapid oxidative processes. The aim of this study was to evaluate the stabilizing effect of lipophilic extracts from two types of berries, sea buckthorn and rose hips, on sunflower oil. This research included the analysis of sunflower oil oxidation products and mechanisms, including the determination of chemical changes occurring in the lipid oxidation process via LC-MS/MS using electrospray ionization in negative and positive mode. Pentanal, hexanal, heptanal, octanal, and nonanal were identified as key compounds formed during oxidation. The individual profiles of the carotenoids from sea buckthorn berries were determined using RP-HPLC. The influence of the carotenoid extraction parameters ascertained from the berries on the oxidative stability of sunflower oil was analyzed. The dynamics of the accumulation of the primary and secondary products of lipid oxidation and the variation of the carotenoid pigment content in the lipophilic extracts of sea buckthorn and rose hips during storage demonstrated good stability at 4 °C in the absence of light for 12 months. The experimental results were applied to mathematical modeling using fuzzy sets and mutual information analysis, which allowed for the prediction of the oxidation of sunflower oil. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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16 pages, 3608 KiB

Open AccessArticle

Medicarpin and Homopterocarpin Isolated from Canavalia lineata as Potent and Competitive Reversible Inhibitors of Human Monoamine Oxidase-B

by Jong Min Oh, Hyun-Jae Jang, Myung-Gyun Kang, Seul-Ki Mun, Daeui Park, Su-Jin Hong, Min Ha Kim, Soo-Young Kim, Sung-Tae Yee and Hoon Kim

Molecules 2023, 28(1), 258; https://doi.org/10.3390/molecules28010258 - 28 Dec 2022

Cited by 7 | Viewed by 1723

Abstract

Thirteen compounds were isolated from the Canavalia lineata pods and their inhibitory activities against human monoamine oxidase-A (hMAO-A) and -B (hMAO-B) were evaluated. Among them, compounds 8 (medicarpin) and 13 (homopterocarpin) showed potent inhibitory activity against hMAO-B (IC₅₀ = 0.45 and 0.72 µM, respectively) with selectivity index (SI) values of 44.2 and 2.07, respectively. Most of the compounds weakly inhibited MAO-A, except 9 (prunetin) and 13. Compounds 8 and 13 were reversible competitive inhibitors against hMAO-B (K_i = 0.27 and 0.21 µM, respectively). Structurally, the 3-OH group at A-ring of 8 showed higher hMAO-B inhibitory activity than 3-OCH3 group at the A-ring of 13. However, the 9-OCH3 group at B-ring of 13 showed higher hMAO-B inhibitory activity than 8,9-methylenedioxygroup at the B-ring of 12 (pterocarpin). In cytotoxicity study, 8 and 13 showed non-toxicity to the normal (MDCK) and cancer (HL-60) cells and moderate toxicity to neuroblastoma (SH-SY5Y) cell. Molecular docking simulation revealed that the binding affinities of 8 and 13 for hMAO-B (−8.7 and −7.7 kcal/mol, respectively) were higher than those for hMAO-A (−3.4 and −7.1 kcal/mol, respectively). These findings suggest that compounds 8 and 13 be considered potent reversible hMAO-B inhibitors to be used for the treatment of neurological disorders. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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22 pages, 4264 KiB

Open AccessArticle

Response Surface Modeling and Optimization of the Extraction of Phenolic Antioxidants from Olive Mill Pomace

by Filipa Paulo, Loleny Tavares and Lúcia Santos

Molecules 2022, 27(23), 8620; https://doi.org/10.3390/molecules27238620 - 6 Dec 2022

Cited by 8 | Viewed by 1792

Abstract

Bioactive compounds from olive mill pomace (OMP) were extracted through a two-step solid-liquid extraction procedure considering four factors at five levels of a central composite rotatable response surface design. The influence of the process variables time of the primary extraction (2.0–4.0 h), solvent-to-sample ratio during the primary extraction (5.0–10.0 mL/g), time of the secondary extraction (1.0–2.0 h), and the solvent-to-sample ratio during the secondary extraction (3.0–5.0 mL/g) were examined. The content of bioactive compounds was determined spectrophotometrically, and the individual phenolic compounds were evaluated by reserved-phase high-performance liquid chromatography (RP-HPLC). The Derringer’s function was used to optimize the extraction process, and the best conditions were found to be 3.2 h for the primary extraction, 10.0 mL/g for the solvent-to-sample ratio and 1.3 h for the secondary extraction associated with a solvent-to-sample ratio of 3.0 mL/g, obtaining a total phenolic content of 50.0 (expressed as mg gallic acid equivalents (GAE)/g dry weight (dw). The response surface methodology proved to be a great alternative for reducing the number of tests, allowing the optimization of the extraction of phenolic antioxidants from OMP with a reduced number of experiments, promoting reductions in cost and analysis time. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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Review

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29 pages, 6191 KiB

Open AccessReview

Seagrass Meadows: Prospective Candidates for Bioactive Molecules

by Hazeena M. Ameen, Ayona Jayadev, Geena Prasad and Deepa Indira Nair

Molecules 2024, 29(19), 4596; https://doi.org/10.3390/molecules29194596 - 27 Sep 2024

Viewed by 1460

Abstract

Seagrass meadows consist of angiosperms that thrive fully submerged in marine environments and form distinct ecosystems. They provide essential support for many organisms, acting as nursery grounds for species of economic importance. Beyond their ecological roles, seagrasses and their associated microbiomes are rich sources of bioactive compounds with the potential to address numerous human healthcare challenges. Seagrasses produce bioactive molecules responding to physical, chemical, and biological environmental changes. These activities can treat microbe-borne diseases, skin diseases, diabetes, muscle pain, helminthic diseases, and wounds. Seagrasses also offer potential secondary metabolites that can be used for societal benefits. Despite numerous results on their presence and bioactive derivatives, only a few studies have explored the functional and therapeutic properties of secondary metabolites from seagrass. With the increasing spread of epidemics and pandemics worldwide, the demand for alternative drug sources and drug discovery has become an indispensable area of research. Seagrasses present a reliable natural source, making this an opportune moment for further exploration of their pharmacological activities with minimal side effects. This review provides a comprehensive overview of the biochemical, phytochemical, and biomedical applications of seagrasses globally over the last two decades, highlighting the prospective areas of future research for identifying biomedical applications. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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38 pages, 7966 KiB

Open AccessReview

Electrochemical Characterization of the Antioxidant Properties of Medicinal Plants and Products: A Review

by Guzel Ziyatdinova and Alena Kalmykova

Molecules 2023, 28(5), 2308; https://doi.org/10.3390/molecules28052308 - 2 Mar 2023

Cited by 11 | Viewed by 3485

Abstract

Medicinal plants are an important source of bioactive compounds with a wide spectrum of practically useful properties. Various types of antioxidants synthesized in plants are the reasons for their application in medicine, phytotherapy, and aromatherapy. Therefore, reliable, simple, cost-effective, eco-friendly, and rapid methods for the evaluation of antioxidant properties of medicinal plants and products on their basis are required. Electrochemical methods based on electron transfer reactions are promising tools to solve this problem. Total antioxidant parameters and individual antioxidant quantification can be achieved using suitable electrochemical techniques. The analytical capabilities of constant-current coulometry, potentiometry, various types of voltammetry, and chrono methods in the evaluation of total antioxidant parameters of medicinal plants and plant-derived products are presented. The advantages and limitations of methods in comparison to each other and traditional spectroscopic methods are discussed. The possibility to use electrochemical detection of the antioxidants via reactions with oxidants or radicals (N- and O-centered) in solution, with stable radicals immobilized on the electrode surface, via oxidation of antioxidants on a suitable electrode, allows the study of various mechanisms of antioxidant actions occurring in living systems. Attention is also paid to the individual or simultaneous electrochemical determination of antioxidants in medicinal plants using chemically modified electrodes. Full article

(This article belongs to the Special Issue Natural Products from Plant: From Determination to Application)

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