Biological and Chemical Activity of Metabolites of Medicinal Plants, Volume II

A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 10789

Special Issue Editors


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Guest Editor
Centro de Investigación Biomédica del Sur, Instituto Mexicano del Seguro Social, Argentina No. 1, Col. Centro, Xochitepec 62790, Morelos, Mexico
Interests: natural products; phytochemistry; structural elucidation; pharmacology; secondary metabolites
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Centro de Investigación Biomédica del Sur, Instituto Mexicano del Seguro Social, Argentina No. 1, Col. Centro, Xochitepec 62790, Morelos, Mexico
Interests: natural products; phytochemistry; structural elucidation; pharmacology; secondary metabolites
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Plants have been a very important resource since prehistory, having been used for, among others, the treatment of frequent medical problems, such as infectious, gastrointestinal, pulmonary, metabolic, cardiovascular diseases, etc. Plant metabolism is incredibly important and occurs through enzymatic chemical reactions, which generate products called primary and secondary metabolites. Thus, research on plants used in ethnomedicine is imperative due to their richness as a source of a wide variety of compounds, which can be isolated, characterized, and chemically modified to enhance their biological activities. This Special Issue aims to publish articles on secondary metabolites isolated from plants, as well as their biological effects, and more specifically studies that include extraction processes and the isolation and chemical characterization of active compounds, as well as biological models.

Dr. Manasés González-Cortazar
Dr. Alejandro Zamilpa Alvarez
Guest Editors

Manuscript Submission Information

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Keywords

  • natural product
  • phytochemistry
  • structural elucidation
  • pharmacology
  • secondary metabolites
  • plants
  • extract

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Published Papers (7 papers)

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18 pages, 3364 KiB  
Article
Content and Yield of L-DOPA and Bioactive Compounds of Broad Bean Plants: Antioxidant and Anti-Inflammatory Activity In Vitro
by Paula Beatriz Fuentes-Herrera, Braulio Edgar Herrera-Cabrera, Alma Leticia Martínez-Ayala, Alejandro Zamilpa and Adriana Delgado-Alvarado
Plants 2023, 12(23), 3918; https://doi.org/10.3390/plants12233918 - 21 Nov 2023
Viewed by 1713
Abstract
The broad bean plant contains L-DOPA, a compound that is essential for patients with Parkinson’s disease. However, little has been reported on other broad bean compounds that have beneficial effects on health. The objective was to evaluate plants of four Mexican broad bean [...] Read more.
The broad bean plant contains L-DOPA, a compound that is essential for patients with Parkinson’s disease. However, little has been reported on other broad bean compounds that have beneficial effects on health. The objective was to evaluate plants of four Mexican broad bean varieties to determine the content and yield of total phenolic compounds (TPC), total flavonoids (TF), and L-DOPA, as well as to analyze the flavonoid profile and antioxidant (AA) and anti-inflammatory (AANTI) activity in vitro. Broad bean seeds were sown in the field and plants were harvested 20 days after emergence. The analyses were performed with visible UV spectrophotometry and HPLC. The variety José María produced the highest yield of TPC (9.30 g m−2), TF (8.08 g m−2), and L-DOPA (5.64 g m−2) per unit of area. The highest yields per plant were obtained with the Rojita variety: TPC (0.25 g plant−1), TF (0.21 g plant−1), and L-DOPA (0.17 g plant−1). This variety also had the highest antioxidant (IC50 = 87.68 µg mL−1) and anti-inflammatory (IC50 = 74.40 mg mL−1) activity, which was attributed to the L-DOPA compounds and to rutin and isoorientins, respectively. The flavonoid profile revealed the presence of rutin and isoorientins, which had not been previously detected in the broad bean plant. Full article
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15 pages, 5883 KiB  
Article
Pharmacological and Chemical Analysis of Bauhinia divaricata L. Using an In Vitro Antiadipogenic Model
by Ana Laura Islas-Garduño, Ofelia Romero-Cerecero, Antonio Ruperto Jiménez-Aparicio, Jaime Tortoriello, Rosa Mariana Montiel-Ruiz, Manases González-Cortazar and Alejandro Zamilpa
Plants 2023, 12(22), 3799; https://doi.org/10.3390/plants12223799 - 8 Nov 2023
Viewed by 868
Abstract
Obesity is characterized by an excessive and abnormal accumulation of fat. According to the 2022 National Health and Nutrition Survey, in Mexico, the prevalence of overweight and obesity—diagnosed if one’s body mass index (BMI) was ≥25 kg/m2—in adults was 75.2%. A [...] Read more.
Obesity is characterized by an excessive and abnormal accumulation of fat. According to the 2022 National Health and Nutrition Survey, in Mexico, the prevalence of overweight and obesity—diagnosed if one’s body mass index (BMI) was ≥25 kg/m2—in adults was 75.2%. A strong association between the amount of visceral fat and diseases such as diabetes mellitus type II has been recognized. Species of the Bauhinia genus have lipid-lowering and antidiabetic properties. The aim of this work was to evaluate the lipolytic and antiadipogenic activity of Bauhinia divaricata L. in 3T3-L1 cells and to identify the major compounds in the bioactive treatments. The extraction of aerial parts allowed us to obtain hexanic (BdHex), ethyl acetate (BdEAc), and hydroalcoholic (BdHA) extracts. Lipid levels were measured in 3T3-L1 cells differentiated into adipocytes. Our evaluation of cell viability identified an IC50 > 1000 μg/mL in all the extracts, and our evaluation of the antiadipogenic activity indicated that there was a significant reduction (p < 0.001) in the accumulation of lipids with hydroalcoholic (60%) and ethyl acetate (75%) extracts of B. divaricate compared with metformin at 30 mM (65%). The major compounds identified in these extracts were as follows: triacetin (1), 2,3-dihydroxypropyl acetate (2), (3E)-2-methyl-4-(1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl)-3-buten-2-ol (3), 2,5-dihydroxyphenylacetic acid (4), (3R)-3-hydroxydodecanoic acid (5), kaempferol-3-O-rhamnoside (6), and quercetin 3-O-rhamnoside (7). Some of these naturally occurring compounds have been related to the anti-obesity effects of other medicinal plants; therefore, these compounds isolated from B. divaricata could be responsible for inhibiting the differentiation process from preadipocytes to mature adipocytes. Full article
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18 pages, 8503 KiB  
Article
Cyclic Hexapeptide from Bouvardia ternifolia (Cav.) Schltdl. and Neuroprotective Effects of Root Extracts
by Yury Maritza Zapata Lopera, Gabriela Trejo-Tapia, Manasés González-Cortazar, Maribel Herrera-Ruiz, Alejandro Zamilpa and Enrique Jiménez-Ferrer
Plants 2023, 12(14), 2600; https://doi.org/10.3390/plants12142600 - 10 Jul 2023
Cited by 1 | Viewed by 1580
Abstract
Bouvardia ternifolia (Cav.) Schltdl. is a shrub that belongs to the Rubiaceae family and is distributed throughout México; it has been used for its antioxidant, neuroprotective, and anti-inflammatory properties. This work aimed to evaluate the protective effects of B. ternifolia root extracts on [...] Read more.
Bouvardia ternifolia (Cav.) Schltdl. is a shrub that belongs to the Rubiaceae family and is distributed throughout México; it has been used for its antioxidant, neuroprotective, and anti-inflammatory properties. This work aimed to evaluate the protective effects of B. ternifolia root extracts on the blood-brain barrier and the positive regulation of cytokines IL-1β, IL-6, and TNF-α, and the characterization of compounds present in the dichloromethane (BtD) and hexane (BtH) extracts. Male ICR mice were orally administered with B. ternifolia extracts for 5 days before a single injection of LPS. Administration of BtH and BtD significantly decreased Evans blue leakage into brain tissue by 70% and 68%, respectively. Meloxicam (MX) decreased the concentration of IL-1β by 39.6%; BtM by 53.9%; BtAq by 48.4%; BtD by 31.9%, and BtH by 37.7%. BtH was the only treatment that significantly decreased the concentration of IL-6 by 32.2%. The concentration of TNF-α declined with each of the treatments. The chemical composition of BtD and BtH was characterized by GC–MS, and the cyclic hexapeptide was identified by 13C, 1H NMR, and two-dimension techniques. In the BtD extract, seven compounds were found and in BtH 13 compounds were found. The methanolic (BtM) and aqueous (BtAq) extracts were not subjected to chemical analysis, because they did not show a significant difference in the BBB protection activity. Therefore, the results suggested that the extracts BtD and BtH protect the blood-brain barrier, maintaining stable its selective permeability, thereby preventing LPS from entering the brain tissue. Simultaneously, they modulate the production of IL-1β, IL-6, and TNF-α. It is important to note that this research only evaluated the complete extracts. Full article
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16 pages, 4949 KiB  
Article
Chemical Characterization, Antilipidemic Effect and Anti-Obesity Activity of Ludwigia octovalvis in a Murine Model of Metabolic Syndrome
by Dulce Lourdes Morales-Ferra, Miguel Ángel Zavala-Sánchez, Enrique Jiménez-Ferrer, Celeste Trejo-Moreno, Manasés González-Cortazar, Claudia I. Gamboa-Gómez, Fernando Guerrero-Romero and Alejandro Zamilpa
Plants 2023, 12(13), 2578; https://doi.org/10.3390/plants12132578 - 7 Jul 2023
Cited by 1 | Viewed by 981
Abstract
Ludwigia octovalvis (Jacq.) P.H. Raven is widely used in traditional medicine for different illnesses, including diabetes and hypertension. However, its impact on lipotoxicity and metabolic syndrome in vivo has not been addressed. Therefore, the aim of this study was to evaluate the effects [...] Read more.
Ludwigia octovalvis (Jacq.) P.H. Raven is widely used in traditional medicine for different illnesses, including diabetes and hypertension. However, its impact on lipotoxicity and metabolic syndrome in vivo has not been addressed. Therefore, the aim of this study was to evaluate the effects of this plant on the metabolic syndrome parameters in a C57BL6J mouse hypercaloric diet model. L. octovalvis hydroalcoholic extract and its ethyl acetate fraction (25 mg/kg/day) were used for sub-chronic assessment (10 weeks). Additionally, four subfractions (25 mg/kg) were evaluated in the postprandial triglyceridemia test in healthy C57BL6J mice. The hydroalcoholic extract and ethyl acetate fraction significantly decreased body weight gain (−6.9 g and −1.5 g), fasting glycemia (−46.1 and −31.2 mg/dL), systolic (−26.0 and −22.5 mmHg) and diastolic (−8.1 and 16.2 mmHg) blood pressure, free fatty acid concentration (−13.8 and −8.0 μg/mL) and insulin-resistance (measured by TyG index, −0.207 and −0.18), compared to the negative control. A postprandial triglyceridemia test showed that the effects in the sub-chronic model are due, at least in part, to improvement in this parameter. L. octovalvis treatments, particularly the hydroalcoholic extract, improve MS alterations and decrease free fatty acid concentration. These effects are possibly due to high contents of corilagin and ellagic acid. Full article
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13 pages, 2481 KiB  
Article
Intra- and Interspecies Differences of Two Cecropia Species from Tabasco, Mexico, Determined through the Metabolic Analysis and 1H-NMR-Based Fingerprinting of Hydroalcoholic Extracts
by Eric Jaziel Medrano-Sánchez, Gloria Ivonne Hernández-Bolio, Carlos Ernesto Lobato-García, Manasés González-Cortazar, Mayra Antunez-Mojica, Ammy Joana Gallegos-García, Cristian Octavio Barredo-Hernández, Ricardo López-Rodríguez, Nelly Cristina Aguilar-Sánchez and Abraham Gómez-Rivera
Plants 2023, 12(13), 2440; https://doi.org/10.3390/plants12132440 - 25 Jun 2023
Cited by 1 | Viewed by 1329
Abstract
The genus Cecropia is used in the traditional medicine of Tabasco, Mexico, in diabetes and hypertension treatments, mainly without distinction of the species. This contribution aimed to carry out the metabolic analysis and Proton Nuclear Magnetic Resonance (1H-NMR) spectroscopy-based fingerprinting of [...] Read more.
The genus Cecropia is used in the traditional medicine of Tabasco, Mexico, in diabetes and hypertension treatments, mainly without distinction of the species. This contribution aimed to carry out the metabolic analysis and Proton Nuclear Magnetic Resonance (1H-NMR) spectroscopy-based fingerprinting of the hydroalcoholic leaf extracts of Cecropia peltata (Cp) and Cecropia obtusifolia (Co) collected in five sub-regions of the State of Tabasco (Cp1, “Centro”; Cp2, “Chontalpa”; Cp3, “Pantanos”; Cp4, “Ríos” and Co5, “Sierra”). Firstly, the extracts were evaluated for their Total Phenol Content (TPC) and Total Flavonoid Content (TFC) by spectrophotometric methods. In addition, metabolic analysis was performed using High-Performance Liquid Chromatography with Diode-Array Detection HPLC–DAD, which allowed the quantification of the chemical markers: chlorogenic acid, isoorientin, and orientin, as well as a vitexin analog. Finally, metabolomic analysis was carried out based on the 1H-NMR spectra. The Cp4 extract (C. peltata from the “Ríos” sub-region) presented the highest values of TPC (155 ± 9.1 mg GAE/g E) and TFC (724 ± 22.2 mg RE/g E). The metabolic analysis was similar among the five samples; the highest concentrations of the four chemical markers were found in Cp3 (C. peltata from the “Pantanos” sub-region) for chlorogenic acid (39.8 ± 2.3 mg/g) and isoorientin (51.5 ± 2.9 mg/g), in Cp4 for orientin (49.9 ± 0.6 mg/g), and in Cp2 (C. peltata from the “Chontalpa” sub-region) for the vitexin analog (6.2 ± 0.2 mg/g). The metabolic analysis and the 1H-NMR fingerprint analysis showed intraspecies differences among the C. peltata samples and interspecies between C. peltata and C. obtusifolia, which were attributed to variations in the metabolite groups as well as in the proportion of sugars such as glucose and xylose. Full article
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15 pages, 6024 KiB  
Article
Alternative Rooting Methods for Medicinal Cannabis Cultivation in Denmark—Preliminary Results
by Bruno Trevenzoli Favero, Jacob Kromann Salomonsen and Henrik Lütken
Plants 2023, 12(11), 2216; https://doi.org/10.3390/plants12112216 - 3 Jun 2023
Viewed by 2669
Abstract
Cannabis sativa L. is typically propagated through micropropagation or vegetative cuttings, but the use of root-inducing hormones, such as indole-3-butyric acid (IBA), is not allowed for growing medicinal cannabis in Denmark. This study examined alternative rooting treatments, including Rhizobium rhizogenes inoculation, water-only as [...] Read more.
Cannabis sativa L. is typically propagated through micropropagation or vegetative cuttings, but the use of root-inducing hormones, such as indole-3-butyric acid (IBA), is not allowed for growing medicinal cannabis in Denmark. This study examined alternative rooting treatments, including Rhizobium rhizogenes inoculation, water-only as well as IBA treatments, in eight cannabis cultivars. PCR on root tissue suggested that 19% of R. rhizogenes-inoculated cuttings were transformed. These were derived from “Herijuana”, “Wild Thailand”, “Motherlode Kush”, and “Bruce Banner”, indicating a variation in cultivar susceptibility toward R. rhizogenes. A 100% rooting success was achieved regardless of cultivar and treatment, suggesting that alternative rooting agents are not required for efficient vegetative propagation. However, rooted cuttings differed in shoot morphology with improved shoot growth in cuttings treated with R. rhizogenes (195 ± 7 mm) or water (185 ± 7 mm) while inhibited shoot growth under IBA treatment (123 ± 6 mm). This could have advantageous economic implications should cuttings not treated with hormone reach maturity faster than those exposed to the hormone, thereby contributing to completing a full growing cycle more effectively. IBA exposure increased root length, root dry weight, and root/shoot dry weight ratio compared to cuttings treated with R. rhizogenes or water but simultaneously inhibited shoot growth compared to these. Full article
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13 pages, 1934 KiB  
Brief Report
Flavonoid Composition and Antioxidant Activity of Tragia volubilis L. Methanolic Extract
by Juan Carlos Romero-Benavides, Nora Cecilia Atiencie-Valarezo and Rodrigo Duarte-Casar
Plants 2023, 12(17), 3139; https://doi.org/10.3390/plants12173139 - 31 Aug 2023
Cited by 1 | Viewed by 1215
Abstract
Several species from the genus Tragia L. in the family Euphorbiaceae are part of the ethnomedicine of traditional cultures, and have a variety of uses. Tragia volubilis L. is a species spread through tropical America and Africa with several ethnomedical uses, particularly for [...] Read more.
Several species from the genus Tragia L. in the family Euphorbiaceae are part of the ethnomedicine of traditional cultures, and have a variety of uses. Tragia volubilis L. is a species spread through tropical America and Africa with several ethnomedical uses, particularly for wound healing and reproductive issues. In this study, we assess the phytochemical composition and antioxidant activity of the methanolic extract of the aerial parts of T. volubilis collected in southern Ecuador. The phytochemical screening of the extract shows the preliminary presence of carbohydrates, alkaloids, flavonoids, and tannins. The extract shows an Antioxidant Activity Index of 1.14, interpreted as strong antioxidant activity. Four flavonoid compounds were isolated through chromatographic procedures and identified through NMR spectroscopy: avicularin, quercitrin, afzelin, and amentoflavone. The biological activity of these compounds matches the ethnopharmacological uses of the species. This is the first phytochemical study of T. volubilis and supports its traditional medicinal uses. Full article
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