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Saponin-Rich Plant Extracts: Properties and Application
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Saponin-Rich Plant Extracts: Properties and Application

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

Deadline for manuscript submissions: closed (31 January 2022) | Viewed by 22813

Special Issue Editor

Prof. Dr. Kamil Wojciechowski

E-Mail Website
Guest Editor
1. Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
2. R&D Director at SaponLabs Ltd, Poland
Interests: surface activity of biomolecules, especially saponins and proteins; extraction of biosurfactants from plant material; interaction of biomolecules with model biological membranes; cosmetic applications of biosurfactants

Special Issue Information

Dear Colleagues,

Saponins are secondary metabolites produced mostly by plants. A characteristic structural feature of all saponins is the presence of either a triterpene or a steroid aglycon part, decorated with 1–3 oligosugar groups (glycon) linked via ether or ester bonds. The monocotyledon plants mainly produce steroidal–aglycone saponins, while dicotyledons produce triterpenoid ones. As the glycon and aglycon parts have a plethora of chemical structures, the number of possible saponin structures is almost unlimited, constantly challenging analytical chemists, who struggle with the lack of analytical standards for saponins. Each glycon–aglycon combination provides the molecule with a different lipophilic–hydrophilic balance and, consequently, brings about unique surface, self-aggregation, and biological activity. The latter seems to be related to the defense of the host plant against pathogens. The amphiphilic nature helps to penetrate biological membranes of pathogens and to render them permeable to accompanying toxins, e.g., saporins, often co-existing with saponins in plants as part of their defense system. The membrane-penetrating ability seems to be lipid- and cholesterol-dependent. Consequently, some saponins show membranolytic activity towards cholesterol-rich erythrocytes (hemolysis). In opposition to the hypotheses assuming an active role in plant defense mechanisms, some researchers suggest that saponins are only intermediate products that provide secure means of storing the biologically active aglycons and/or sugars in biologically inert forms.

Our understanding of the chemical, physicochemical, and biological activity of saponins has recently improved, mainly due to the recent progress in the development of analytical tools but also due to the increasing interest in natural products. After two centuries of fascination and intense development of synthetic chemistry, we realize that Nature is still more efficient at producing certain complex molecules. With our current rate of exploiting the Earth’s non-renewable resources, humankind will soon face coal, oil, and gas shortages. Saponins extracted from plants offer several advantages over many currently dominant synthetic surfactants, foaming and emulsifying agents, and pharmaceutical and food ingredients. At this point, it is worth mentioning that saponins have been part of our everyday diet since the dawn of humankind. Some common dietary sources of saponins include soybeans, quinoa, beans, lentils, peas, spinach, oats, asparagus, fenugreek, garlic, sugar beets, potatoes, green peppers, tomatoes, onions, and tea.

In parallel to characterizing and finding new applications for both the already-known and the newly identified saponins, our efforts should also focus on improved and sustainable methods for their extraction. For this Special Issue, we welcome studies that present research outcomes on all aspects of saponin-rich plant extracts, including but not limited to the topics mentioned above.

Prof. Dr. Kamil Wojciechowski
Guest Editor

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Keywords

  • saponin
  • chromatographic analysis
  • biological membranes
  • self-aggregation
  • surface activity
  • biological activity
  • self-aggregation
  • extraction
  • sapogenin
  • foams
  • emulsions

Published Papers (8 papers)

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Research

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17 pages, 8424 KiB  
Article
Structure and Undulations of Escin Adsorption Layer at Water Surface Studied by Molecular Dynamics
by Sonya Tsibranska, Anela Ivanova, Slavka Tcholakova and Nikolai Denkov
Molecules 2021, 26(22), 6856; https://doi.org/10.3390/molecules26226856 - 13 Nov 2021
Cited by 4 | Viewed by 1658
Abstract
The saponin escin, extracted from horse chestnut seeds, forms adsorption layers with high viscoelasticity and low gas permeability. Upon deformation, escin adsorption layers often feature surface wrinkles with characteristic wavelength. In previous studies, we investigated the origin of this behavior and found that [...] Read more.
The saponin escin, extracted from horse chestnut seeds, forms adsorption layers with high viscoelasticity and low gas permeability. Upon deformation, escin adsorption layers often feature surface wrinkles with characteristic wavelength. In previous studies, we investigated the origin of this behavior and found that the substantial surface elasticity of escin layers may be related to a specific combination of short-, medium-, and long-range attractive forces, leading to tight molecular packing in the layers. In the current study, we performed atomistic molecular dynamics simulations of 441 escin molecules in a dense adsorption layer with an area per molecule of 0.49 nm2. We found that the surfactant molecules are less submerged in water and adopt a more upright position when compared to the characteristics determined in our previous simulations with much smaller molecular models. The number of neighbouring molecules and their local orientation, however, remain similar in the different-size models. To maintain their preferred mutual orientation, the escin molecules segregate into well-ordered domains and spontaneously form wrinkled layers. The same specific interactions (H-bonds, dipole–dipole attraction, and intermediate strong attraction) define the complex internal structure and the undulations of the layers. The analysis of the layer properties reveals a characteristic wrinkle wavelength related to the surface lateral dimensions, in qualitative agreement with the phenomenological description of thin elastic sheets. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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14 pages, 987 KiB  
Article
Spirostanol Saponins from Flowers of Allium Porrum and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
by Juraj Harmatha, Miloš Buděšínský, Zdeněk Zídek and Eva Kmoníčková
Molecules 2021, 26(21), 6533; https://doi.org/10.3390/molecules26216533 - 29 Oct 2021
Cited by 4 | Viewed by 1950
Abstract
Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of Allium porrum L. (garden leek). Two of them were identical [...] Read more.
Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of Allium porrum L. (garden leek). Two of them were identical with the already known leek plant constituents: aginoside (1) and 6-deoxyaginoside (2). The third one was identified as new component of A. porrum; however, it was found identical with yayoisaponin A (3) obtained earlier from a mutant of elephant garlic Allium ampeloprasun L. It is a derivative of the aginoside (1) with additional glucose in its glycosidic chain, identified by MS and NMR analysis as (2α, 3β, 6β, 25R)-2,6-dihydroxyspirostan-3-yl β-D-glucopyranosyl-(1 → 3)-β-D-glucopranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl]-(1 → 4)-β-D-galactopyranoside, previously reported also under the name alliporin. The leek native saponins were tested together with other known and structurally related saponins (tomatonin and digitonin) and with their related aglycones (agigenin and diosgenin) for in vitro cytotoxicity and for effects on NO production in mouse peritoneal cells. The highest inhibitory effects were exhibited by 6-deoxyaginoside. The obtained toxicity data, however, closely correlated with the suppression of NO production. Therefore, an unambiguous linking of obtained bioactivities of saponins with their expected immunobiological properties remained uncertain. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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15 pages, 1972 KiB  
Article
Soapwort (Saponaria officinalis L.) Extract vs. Synthetic Surfactants—Effect on Skin-Mimetic Models
by Ilona Jurek, Aleksandra Szuplewska, Michał Chudy and Kamil Wojciechowski
Molecules 2021, 26(18), 5628; https://doi.org/10.3390/molecules26185628 - 16 Sep 2021
Cited by 4 | Viewed by 3521
Abstract
Our skin is continuously exposed to different amphiphilic substances capable of interaction with its lipids and proteins. We describe the effect of a saponin-rich soapwort extract and of four commonly employed synthetic surfactants: sodium lauryl sulfate (SLS), sodium laureth sulfate (SLES), ammonium lauryl [...] Read more.
Our skin is continuously exposed to different amphiphilic substances capable of interaction with its lipids and proteins. We describe the effect of a saponin-rich soapwort extract and of four commonly employed synthetic surfactants: sodium lauryl sulfate (SLS), sodium laureth sulfate (SLES), ammonium lauryl sulfate (ALS), cocamidopropyl betaine (CAPB) on different human skin models. Two human skin cell lines were employed: normal keratinocytes (HaCaT) and human melanoma cells (A375). The liposomes consisting of a dipalmitoylphosphatidylcholine/cholesterol mixture in a molar ratio of 7:3, mimicking the cell membrane of keratinocytes and melanoma cells were employed as the second model. Using dynamic light scattering (DLS), the particle size distribution of liposomes was analyzed before and after contact with the tested (bio)surfactants. The results, supplemented by the protein solubilization tests (albumin denaturation test, zein test) and oil emulsification capacity (using olive oil and engine oil), showed that the soapwort extract affects the skin models to a clearly different extent than any of the tested synthetic surfactants. Its protein and lipid solubilizing potential are much smaller than for the three anionic surfactants (SLS, ALS, SLES). In terms of protein solubilization potential, the soapwort extract is comparable to CAPB, which, however, is much harsher to lipids. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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11 pages, 2635 KiB  
Article
Evaluation of the Saponin Content in Panax vietnamensis Acclimatized to Lam Dong Province by HPLC–UV/CAD
by Huy Truong Nguyen, Kim Long Vu-Huynh, Hien Minh Nguyen, Huong Thuy Le, Thi Hong Van Le, Jeong Hill Park and Minh Duc Nguyen
Molecules 2021, 26(17), 5373; https://doi.org/10.3390/molecules26175373 - 03 Sep 2021
Cited by 5 | Viewed by 3047
Abstract
Panax vietnamensis, or Vietnamese ginseng (VG), an endemic Panax species in Vietnam, possesses a unique saponin profile and interesting biological activities. This plant is presently in danger of extinction due to over-exploitation, resulting in many preservation efforts towards the geographical acclimatization of [...] Read more.
Panax vietnamensis, or Vietnamese ginseng (VG), an endemic Panax species in Vietnam, possesses a unique saponin profile and interesting biological activities. This plant is presently in danger of extinction due to over-exploitation, resulting in many preservation efforts towards the geographical acclimatization of VG. Yet, no information on the saponin content of the acclimatized VG, an important quality indicator, is available. Here, we analyzed the saponin content in the underground parts of two- to five-year-old VG plants acclimatized to Lam Dong province. Nine characteristic saponins, including notoginsenoside-R1, ginsenoside-Rg1, -Rb1, -Rd, majonoside-R1, -R2 vina-ginsenoside-R2, -R11, and pseudoginsenoside-RT4, were simultaneously determined by HPLC coupled with UV and with a charged aerosol detector (CAD). Analyzing the results illustrated that the detection of characteristic ocotillol-type saponins in VG by CAD presented a superior capacity compared with that of UV, thus implying a preferential choice of CAD for the analysis of VG. The quantitative results indicating the saponin content in the underground parts of VG showed an increasing tendency from two to five years old, with the root and the rhizome exhibiting different saponin accumulation patterns. This is the first study that reveals the preliminary success of VG acclimatization and thereby encourages the continuing efforts to develop this valuable saponin-rich plant. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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17 pages, 8231 KiB  
Article
Stable DOPG/Glycyrrhizin Vesicles with a Wide Range of Mixing Ratios: Structure and Stability as Seen by Scattering Experiments and Cryo-TEM
by Carina Dargel, Friederike Gräbitz-Bräuer, Ramsia Geisler, Pascal Fandrich, Yvonne Hannappel, Lionel Porcar and Thomas Hellweg
Molecules 2021, 26(16), 4959; https://doi.org/10.3390/molecules26164959 - 16 Aug 2021
Cited by 5 | Viewed by 2369
Abstract
Phosphatidylglycerols represent a large share of the lipids in the plasmamembrane of procaryotes. Therefore, this study investigates the role of charged lipids in the plasma membrane with respect to the interaction of the antiviral saponin glycyrrhizin with such membranes. Glycyrrhizin is a natural [...] Read more.
Phosphatidylglycerols represent a large share of the lipids in the plasmamembrane of procaryotes. Therefore, this study investigates the role of charged lipids in the plasma membrane with respect to the interaction of the antiviral saponin glycyrrhizin with such membranes. Glycyrrhizin is a natural triterpenic-based surfactant found in licorice. Vesicles made of 1,2-dioleoyl-sn-glycero-3-phospho-rac-(1’-glycerol) (DOPG)/glycyrrhizin are characterized by small-angle scattering with neutrons and X-rays (SANS and SAXS). Small-angle scattering data are first evaluated by the model-independent modified Kratky–Porod method and afterwards fitted by a model describing the shape of small unilamellar vesicles (SUV) with an internal head-tail contrast. Complete miscibility of DOPG and glycyrrhizin was revealed even at a ratio of lipid:saponin of 1:1. Additional information about the chain-chain correlation distance of the lipid/saponin mixtures in the SUV structures is obtained from wide-angle X-ray scattering (WAXS). Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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20 pages, 3459 KiB  
Article
Theasaponin E1 Inhibits Platinum-Resistant Ovarian Cancer Cells through Activating Apoptosis and Suppressing Angiogenesis
by Bo Li, Tuantuan Tong, Ning Ren, Gary O. Rankin, Yon Rojanasakul, Youying Tu and Yi Charlie Chen
Molecules 2021, 26(6), 1681; https://doi.org/10.3390/molecules26061681 - 17 Mar 2021
Cited by 15 | Viewed by 2995
Abstract
Novel therapeutic strategies for ovarian cancer treatment are in critical need due to the chemoresistance and adverse side effects of platinum-based chemotherapy. Theasaponin E1 (TSE1) is an oleanane-type saponin from Camellia sinensis seeds. Its apoptosis-inducing, cell cycle arresting and antiangiogenesis activities against [...] Read more.
Novel therapeutic strategies for ovarian cancer treatment are in critical need due to the chemoresistance and adverse side effects of platinum-based chemotherapy. Theasaponin E1 (TSE1) is an oleanane-type saponin from Camellia sinensis seeds. Its apoptosis-inducing, cell cycle arresting and antiangiogenesis activities against platinum-resistant ovarian cancer cells were elucidated in vitro and using the chicken chorioallantoic membrane (CAM) assay. The results showed that TSE1 had more potent cell growth inhibitory effects on ovarian cancer OVCAR-3 and A2780/CP70 cells than cisplatin and was lower in cytotoxicity to normal ovarian IOSE-364 cells. TSE1 significantly induced OVCAR-3 cell apoptosis via the intrinsic and extrinsic apoptotic pathways, slightly arresting cell cycle at the G2/M phase, and obviously inhibited OVCAR-3 cell migration and angiogenesis with reducing the protein secretion and expression of vascular endothelial growth factor (VEGF). Western bolt assay showed that Serine/threonine Kinase (Akt) signaling related proteins including Ataxia telangiectasia mutated kinase (ATM), Phosphatase and tensin homolog (PTEN), Akt, Mammalian target of rapamycin (mTOR), Ribosome S6 protein kinase (p70S6K) and e IF4E-binding protein 1(4E-BP1) were regulated, and Hypoxia inducible factor-1α (HIF-1α) protein expression was decreased by TSE1 in OVCAR-3 cells. Moreover, TSE1 treatment potently downregulated protein expression of the Notch ligands including Delta-like protein 4 (Dll4) and Jagged1, and reduced the protein level of the intracellular domain (NICD) of Notch1. Combination treatment of TSE1 with the Notch1 signaling inhibitor tert-butyl (2S)-2-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoyl]amino]-2-phenylacetate (DAPT), or the Akt signaling inhibitor wortmannin, showed a stronger inhibition toward HIF-1α activation compared with single compound treatment. Taken together, TSE1 might be a potential candidate compound for improving platinum-resistant ovarian cancer treatment via Dll4/Jagged1-Notch1-Akt-HIF-1α axis. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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10 pages, 2350 KiB  
Article
Laboratory and Field Evaluation of the Phytotoxic Activity of Sapindus mukorossi Gaertn Pulp Extract and Identification of a Phytotoxic Substance
by Ziyang Dai, Jin Wang, Xiaojiang Ma, Jia Sun and Feng Tang
Molecules 2021, 26(5), 1318; https://doi.org/10.3390/molecules26051318 - 02 Mar 2021
Cited by 6 | Viewed by 1819
Abstract
Interest in finding plant-based herbicides to supplement synthesized herbicides is increasing. Although the extract of Sapindus mukorossi Gaertn has been reported to have herbicidal activity, little is known about phytotoxic substances and their efficacy of weed control in the field. To identify phytotoxic [...] Read more.
Interest in finding plant-based herbicides to supplement synthesized herbicides is increasing. Although the extract of Sapindus mukorossi Gaertn has been reported to have herbicidal activity, little is known about phytotoxic substances and their efficacy of weed control in the field. To identify phytotoxic substances, the bioassay-guided fractionation by column chromatography and high-speed counter-current chromatography (HSCCC) was carried out. The phytotoxic activity assay, performed by the agar medium method, showed that the 70% ethanol fraction exhibited strong root growth inhibition against Trifolium pratense with an 50% inhibitory concentration (IC50) value of 35.13 mg/L. An active compound was isolated from the 70% ethanol fraction and identified as hederagenin 3-o-β-D-xylopyranosyl-(1→3)-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (Compound A). Compound A had an IC50 value of 16.64 mg/L. Finally, a new formulation was prepared based on the 70% ethanol fraction, which exhibited good efficacy against broadleaf weeds in a carrot field. The fresh weight control efficacy was 78.7% by 45 days after treatment at the dose of 1500 g a. i./ha. Hence, the extract of S. mukorossi pulp could be a promising supplement to the synthesized herbicides. Furthermore, compound A from S. mukorossi may be responsible for its phytotoxic activity. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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Review

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20 pages, 2981 KiB  
Review
Recent Advances and Applications of Plant-Based Bioactive Saponins in Colloidal Multiphase Food Systems
by Mengyue Xu, Zhili Wan and Xiaoquan Yang
Molecules 2021, 26(19), 6075; https://doi.org/10.3390/molecules26196075 - 08 Oct 2021
Cited by 12 | Viewed by 3084
Abstract
The naturally occurring saponins exhibit remarkable interfacial activity and also possess many biological activities linking to human health benefits, which make them particularly attractive as bifunctional building blocks for formulation of colloidal multiphase food systems. This review focuses on two commonly used food-grade [...] Read more.
The naturally occurring saponins exhibit remarkable interfacial activity and also possess many biological activities linking to human health benefits, which make them particularly attractive as bifunctional building blocks for formulation of colloidal multiphase food systems. This review focuses on two commonly used food-grade saponins, Quillaja saponins (QS) and glycyrrhizic acid (GA), with the aim of clarifying the relationship between the structural features of saponin molecules and their subsequent self-assembly and interfacial properties. The recent applications of these two saponins in various colloidal multiphase systems, including liquid emulsions, gel emulsions, aqueous foams and complex emulsion foams, are then discussed. A particular emphasis is on the unique use of GA and GA nanofibrils as sole stabilizers for fabricating various multiphase food systems with many advanced qualities including simplicity, ultrastability, stimulability, structural viscoelasticity and processability. These natural saponin and saponin-based colloids are expected to be used as sustainable, plant-based ingredients for designing future foods, cosmetics and pharmaceuticals. Full article
(This article belongs to the Special Issue Saponin-Rich Plant Extracts: Properties and Application)
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