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Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications

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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 (29 February 2024) | Viewed by 19511

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Dr. Maria Inês Moreira Figueiredo Dias

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Instituto Politécnico de Bragança, Centro de Investigação de Montanha (CIMO), Campus Santa Apolonia, Braganca, Portugal
Interests: bioactive compounds; food chemistry; phenolic compounds; chromatography; mass spectrometry
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Dr. José Virgílio Santulhão Pinela

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Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
Interests: food chemistry; bio-based ingredients; antioxidants; extraction methods; process optimization
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Dr. Lillian Barros

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Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253 Bragança, Portugal
Interests: natural bioactive compounds; medicinal chemistry; bioactivity and toxicology; functional applications
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Steroidal and triterpenoid compounds are widely distributed in nature and have been applied in many ways in different sectors. Steroids are solid alcohols with a basic skeleton typically composed of 17 carbons arranged in the form of a perhydrocyclopentanophenanthrene. They have great structural variation and comprise compounds responsible for important biological functions. In turn, triterpenoids display a 30-carbon skeleton with relatively complex cyclic structures, most of which are alcohols, aldehydes, or carboxylic acids. There are also saponins, glycosides of both steroidal and triterpenoid compounds, characterized by their strong foam-forming and surfactant properties in aqueous solution, which can be found in a wide variety of edible and medicinal plants. It is also worth noting the existence of steroidal alkaloids, mainly in Solanaceae plants, brassinosteroids, first isolated in pollen grains of Brassica napus L., and physalins, steroidal constituents of Physalis plants, among many other related bioactive metabolites.

This Special Issue will provide an update on all aspects of the chemistry and bioactivity of steroidal and triterpenoid compounds, bringing together original research and review articles covering the latest findings on natural sources, bioactive and pharmacological properties, and recent applications of these molecules that have been receiving increasing interest in different industrial sectors. Studies focused on extraction, isolation, characterization, and mechanisms of action, among other research subjects, are also welcome.

Dr. Maria Inês Dias
Dr. José Pinela
Dr. Lillian Barros
Guest Editors

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Keywords

Steroids and steroidal compounds
Triterpenoids
Saponins
Biological activities
Medical applications
Food applications
Drug discovery
Vitamin D
Metabolism
Mechanisms of action

Published Papers (6 papers)

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Research

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13 pages, 1896 KiB

Open AccessArticle

Vitamin D Mitigates Hepatic Fat Accumulation and Inflammation and Increases SIRT1/AMPK Expression in AML-12 Hepatocytes

by Eugene Chang

Molecules 2024, 29(6), 1401; https://doi.org/10.3390/molecules29061401 - 21 Mar 2024

Viewed by 736

Abstract

Emerging evidence has demonstrated a strong correlation between vitamin D status and fatty liver disease. Aberrant hepatic fat infiltration contributes to oxidant overproduction, promoting metabolic dysfunction, and inflammatory responses. Vitamin D supplementation might be a good strategy for reducing hepatic lipid accumulation and inflammation in non-alcoholic fatty liver disease and its associated diseases. This study aimed to investigate the role of the most biologically active form of vitamin D, 1,25-dihydroxyvitamin D (1,25(OH)2D), in hepatic fat accumulation and inflammation in palmitic acid (PA)-treated AML-12 hepatocytes. The results indicated that treatment with 1,25(OH)2D significantly decreased triglyceride contents, lipid peroxidation, and cellular damage. In addition, mRNA levels of apoptosis-associated speck-like CARD-domain protein (ASC), thioredoxin-interacting protein (TXNIP), NOD-like receptor family pyrin domain-containing 3 (NLRP3), and interleukin-1β (IL-1β) involved in the NLRP3 inflammasome accompanied by caspase-1 activity and IL-1β expression were significantly suppressed by 1,25(OH)2D in PA-treated hepatocytes. Moreover, upon PA exposure, 1,25(OH)2D-incubated AML-12 hepatocytes showed higher sirtulin 1 (SIRT1) expression and adenosine monophosphate-activated protein kinase (AMPK) phosphorylation. A SIRT1 inhibitor alleviated the beneficial effects of 1,25(OH)2D on PA-induced hepatic fat deposition, IL-1β expression, and caspase-1 activity. These results suggest that the favorable effects of 1,25(OH)2D on hepatic fat accumulation and inflammation may be, at least in part, associated with the SIRT1. Full article

(This article belongs to the Special Issue Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications)

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20 pages, 1506 KiB

Open AccessArticle

Study on Chemical Constituents of Panax notoginseng Leaves

by Xiaojuan Sun, Hongbo Deng, Tengyun Shu, Min Xu, Lihua Su and Haizhou Li

Molecules 2023, 28(5), 2194; https://doi.org/10.3390/molecules28052194 - 27 Feb 2023

Cited by 2 | Viewed by 1796

Abstract

Panax notoginseng (Burk.) F. H. is a genuine medicinal material in Yunnan Province. As accessories, P. notoginseng leaves mainly contain protopanaxadiol saponins. The preliminary findings have indicated that P. notoginseng leaves contribute to its significant pharmacological effects and have been administrated to tranquilize and treat cancer and nerve injury. Saponins from P. notoginseng leaves were isolated and purified by different chromatographic methods, and the structures of 1–22 were elucidated mainly through comprehensive analyses of spectroscopic data. Moreover, the SH-SY5Y cells protection bioactivities of all isolated compounds were tested by establishing L-glutamate models for nerve cell injury. As a result, twenty-two saponins, including eight dammarane saponins, namely notoginsenosides SL₁-SL₈ (1–8), were identified as new compounds, together with fourteen known compounds, namely notoginsenoside NL-A₃ (9), ginsenoside Rc (10), gypenoside IX (11), gypenoside XVII (12), notoginsenoside Fc (13), quinquenoside L₃ (14), notoginsenoside NL-B₁ (15), notoginsenoside NL-C₂ (16), notoginsenoside NL-H₂ (17), notoginsenoside NL-H₁ (18), vina-ginsenoside R₁₃ (19), ginsenoside II (20), majoroside F₄ (21), and notoginsenoside LK₄ (22). Among them, notoginsenoside SL₁ (1), notoginsenoside SL₃ (3), notoginsenoside NL-A₃ (9), and ginsenoside Rc (10) showed slight protective effects against L-glutamate-induced nerve cell injury (30 µM). Full article

(This article belongs to the Special Issue Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications)

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13 pages, 2355 KiB

Open AccessArticle

Decoration of A-Ring of a Lupane-Type Triterpenoid with Different Oxygen and Nitrogen Heterocycles

by Joana L. C. Sousa, Hélio M. T. Albuquerque, Armando J. D. Silvestre and Artur M. S. Silva

Molecules 2022, 27(15), 4904; https://doi.org/10.3390/molecules27154904 - 31 Jul 2022

Viewed by 1490

Abstract

Betulinic acid (BA) was used as starting building block to create a library of novel BA-derived compounds containing O- and N-heterocycles. Firstly, BA was converted into methyl betulonate (BoOMe), which was used as intermediate in the developed methodologies. 1,2-Oxazine-fused BoOMe compounds were obtained in 12–25% global yields through a Michael addition of nitromethane to methyl (E)-2-benzylidenebetulonate derivatives, followed by nitro group reduction and intramolecular cyclization. Remarkably, the triterpene acts as a diastereoselective inducer in the conjugate addition of nitromethane, originating only one diastereomer out of four possible ones. Furthermore, other oxygen and nitrogen-containing heterocycles were installed at the A-ring of BoOMe, affording 2-amino-3-cyano-4H-pyran-fused BoOMe, diarylpyridine-fused BoOMe and 1,2,3-triazole–BoOMe compounds, using simple and straightforward synthetic methodologies. Finally, BA was revealed to be a versatile starting material, allowing the creation of a molecular diversification of compounds containing a triterpenic scaffold and O- and N-heterocycles. Full article

(This article belongs to the Special Issue Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications)

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10 pages, 2077 KiB

Open AccessArticle

Triterpenoid Saponins from the Cultivar “Green Elf” of Pittosporum tenuifolium

by David Pertuit, Anne-Claire Mitaine-Offer, Tomofumi Miyamoto, Chiaki Tanaka, Christine Belloir, Loïc Briand and Marie-Aleth Lacaille-Dubois

Molecules 2021, 26(22), 6805; https://doi.org/10.3390/molecules26226805 - 11 Nov 2021

Viewed by 1724

Abstract

Four oleanane-type glycosides were isolated from a horticultural cultivar “Green Elf” of the endemic Pittosporum tenuifolium (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, 3-O-β-d-galactopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and the known 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C (Eryngioside L). From the roots, the known 3-O-β-d-glucopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyloleanolic acid (Sandrosaponin X) was identified. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR experiments and mass spectrometry (ESI-MS). According to their structural similarities with gymnemic acids, the inhibitory activities on the sweet taste TAS1R2/TAS1R3 receptor of an aqueous ethanolic extract of the leaves and roots, a crude saponin mixture, 3-O-β-d-glucopyranosyl-(1→2)-[α-l-arabinopyranosyl-(1→3)]-β-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and Eryngioside L were evaluated. Full article

(This article belongs to the Special Issue Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications)

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18 pages, 7955 KiB

Open AccessArticle

Variation of Triterpenes in Apples Stored in a Controlled Atmosphere

by Aurita Butkeviciute, Jonas Viskelis, Mindaugas Liaudanskas, Pranas Viskelis, Ceslovas Bobinas and Valdimaras Janulis

Molecules 2021, 26(12), 3639; https://doi.org/10.3390/molecules26123639 - 14 Jun 2021

Cited by 7 | Viewed by 3906

Abstract

Apples are seasonal fruits, and thus after harvesting apples of optimal picking maturity, it is important to prepare them properly for storage and to ensure proper storage conditions in order to minimize changes in the chemical composition and commercial quality of the apples. We studied the quantitative composition of triterpenic compounds in the whole apple, apple peel and apple flesh samples before placing them in the controlled atmosphere (CA) chambers, and at the end of the experiment, 8 months later. HPLC analysis showed that highest total amount of triterpenic compounds (1.99 ± 0.01 mg g⁻¹) was found in the whole apple samples of the ‘Spartan’ cultivar stored under variant VIII (O₂—20%, CO₂—3%, N₂—77%) conditions. Meanwhile, the highest amount of triterpenic compounds (11.66 ± 0.72 mg g⁻¹) was determined in the apple peel samples of the ‘Auksis’ cultivar stored under variant II (O₂—5%, CO₂—1%, N₂—94%) conditions. In the apple peel samples of the ‘Auksis’ cultivar stored under variant I (O₂—21%, CO₂—0.03%, N₂—78.97%) conditions, the amount of individual triterpenic compounds (ursolic, oleanolic, corosolic, and betulinic acids) significantly decreased compared with amount determined before the storage. Therefore, in the apple flesh samples determined triterpenic compounds are less stable during the storage under controlled atmosphere conditions compared with triterpenic compounds determined in the whole apple and apple peel samples. Full article

(This article belongs to the Special Issue Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications)

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16 pages, 14382 KiB

Open AccessReview

Androstenedione (a Natural Steroid and a Drug Supplement): A Comprehensive Review of Its Consumption, Metabolism, Health Effects, and Toxicity with Sex Differences

by Marwa T. Badawy, Mansour Sobeh, Jianbo Xiao and Mohamed A. Farag

Molecules 2021, 26(20), 6210; https://doi.org/10.3390/molecules26206210 - 14 Oct 2021

Cited by 19 | Viewed by 7645

Abstract

Androstenedione is a steroidal hormone produced in male and female gonads, as well as in the adrenal glands, and it is known for its key role in the production of estrogen and testosterone. Androstenedione is also sold as an oral supplement, that is being utilized to increase testosterone levels. Simply known as “andro” by athletes, it is commonly touted as a natural alternative to anabolic steroids. By boosting testosterone levels, it is thought to be an enhancer for athletic performance, build body muscles, reduce fats, increase energy, maintain healthy RBCs, and increase sexual performance. Nevertheless, several of these effects are not yet scientifically proven. Though commonly used as a supplement for body building, it is listed among performance-enhancing drugs (PEDs) which is banned by the World Anti-Doping Agency, as well as the International Olympic Committee. This review focuses on the action mechanism behind androstenedione’s health effects, and further side effects including clinical features, populations at risk, pharmacokinetics, metabolism, and toxicokinetics. A review of androstenedione regulation in drug doping is also presented. Full article

(This article belongs to the Special Issue Steroidal and Triterpenoid Compounds: Natural Sources, Bioactivities and Applications)

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