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Clinical Phytoscience

International Journal of Phytomedicine and Phytotherapy

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Diosgenin and galactomannans, natural products in the pharmaceutical sciences

Clinical Phytoscience volume 7, Article number: 50 (2021) Cite this article

Abstract

Background

Diosgenin is an isospirostane derivative, which is a steroidal sapogenin and the product of acids or enzymes hydrolysis process of dioscin and protodioscin. Galactomannans are heteropolysaccharides composed of D-mannose and D-galactose, which are major sources of locust bean, guar, tara and fenugreek.

Methods

Literature survey was accomplished using multiple databases including PubMed, Science Direct, ISI web of knowledge and Google Scholar.

Results

Four major sources of seed galactomannans are locust bean (Ceratonia siliqua), guar (Cyamopsis tetragonoloba), tara (Caesalpinia spinosa Kuntze), and fenugreek (T.foenum-graecum). Diosgenin has effect on immune system, lipid system, inflammatory and reproductive systems, caner, metabolic process, blood system, blood glucose and calcium regulation. The most important pharmacological benefits of galactomannan are antidiabetic, antioxidant, anticancer, anticholinesterase, antiviral activities, and appropriate for dengue virus and gastric diseases.

Conclusions

Considering the importance of diosgenin and galactomannans, the obtained findings suggest potential of diosgenin and galactomannans as natural products in pharmaceutical industries.

Introduction

Natural products from herbal medicines, particularly traditional Iranian and Chinese medicines have found to be effective for many diseases [1,2,3,4]. Medicinal plants and traditional herbal remedies have been gaining considerable attention in these years because of accessibility, affordability, their safety, promising efficacy and being eco-friendly [5,6,7,8,9]. Galactomannans are heterogeneous polysaccharides comprising a β-(1 → 4) d-mannose backbone branched with α-(1 → 6) linked d-galactose monomeric units. Galactomannans,s nature defined by the parameters, such as intrinsic viscosity, M/G ratio, fine structure and average molecular weight, and it is considered as the natural polysaccharides which are used as the stabilizer, emulsifier and thickener in the food industries. Galactomannans belongs to a family of seed gums and present polymers of galactose and mannose. Diosgenin, a triterpenoid having two pentacyclic rings especially found in fenugreek (Trigonellafoenum-graecum L. - Leguminosae) and roots of wild yam (Dioscoreavillosa L. - Dioscoreaceae), and considered as an antihyperglycemic, antidiabetes, antihypertriacylglycerolemia, and antihypercholesterolemic agent, especially in traditional Chinese medicine. It is biosynthesized from cholesterol via the isoprenoid pathway which involves several steps but starts with acetyl CoA. Galactomannans and Diosgenins are main bioactive components of medicinal plants such as fenugreek. The goal of this manuscript is survey on the most important health benefits and pharmaceutical advantages of galactomannan and diosgenin with considering traditional knowledge of natural products.

Galactomannans

Galactomannans are naturally occurring biocompatible and biodegradable nonionic polysaccharides consisted of mannose and galactose residues, which are commercially isolated from the seeds of guar, carob, fenugreek and tara plants [10,11,12,13,14,15]. Galactomannans are under investigation for the design of various drug delivery carriers such as matrix tablets, microparticles, nanoparticles, polymeric micelles, hydrogels and different pharmaceutical excipients [16, 17], like galactomannan extracted from Trigonella persica (Boiss.) E. Small (Leguminosae) endosperm which is useful in the medicine and pharmaceutical industry [18]. In green and immature seed of Gleditsia sinensis Lam. (Leguminosae) tree, galactomannan was substituted to a great extent with a mannose to galactose (M/G) ration of 2.4 from crude polysaccharides [19]. The seed galactomannan of Bauhinia monandra Kurz (Leguminosae), Bauhinia vahlii Wight & Arn. (Leguminosae), Citrullus colocynthis (L.) Schrad. (Cucurbitaceae), Delonix elata Gamble (Leguminosae), Leucaena leucocephala (Lam.) de Wit (Leguminosae), and Peltophorum pterocarpum (DC.) K. Heyne (Leguminosae) could be explored as an effective alternative to commercial galactomannans for industrial purposes [20,21,22,23,24]. Galactomannans from Prosopis affinis Spreng (Leguminosae), seeds has shown molecular weight distribution and intrinsic viscosity similar to those of commercial gums [25]. Galactomannan from fenugreek attributes depicted a very food candidacy for industrial application [26, 27]. Liu et al. [28] reported that degradation of galactose was slightly easier than that of mannose. Galactomannans of G.sinensis, fenugreek and guar galactomannans, showed a rod-like and fibrous filament network structure [29]. Galactomannans fraction from Gleditsia triacanthos L. (Leguminosae) seeds could become a suitable alternative to be used as a food texture modifier for starch-based products [30]. Coelho et al. [31] showed that galactomannan films have a large potential application into the engineering area and food science, like G. triacanthos extract which has shown to have excellent filmogenic properties [32, 33]. Galactomannan from Sesbania cannabina (Retz.) Pers. (Leguminosae) was applied for fabricate high-strength film [34]. Retama raetam (Forssk.) Webb & Berthel (Fabaceae) galactomannan can reduce the glycemic index of starchy foods [35]. Galactomannan pretreatment constitutes a novel and promising therapy to decrease local and remote damage triggered by intestinal ischemia-reperfusion injury [36]. Chemical structure of galactomannan has shown in Fig. 1. The major pharmacological effects of galactomanna have been shown in Table 1.

Fig. 1
figure 1

Chemical structure of galactomannan

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Table 1 The most important pharmacological effects of galactomannan
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Diosgenin

Diosgenin (25R-spirost-5-en-3β-ol) (Fig. 2) is an important steroid-based compound obtained from the secondary metabolic products of plant species [45, 46], which has been proven as an important bioactive drug component due to its anti-cancer activity, anti-cardioprotective activity, anti-diabetic effects, anti-microbial effects, anti-thrombotic effects, anti-inflammatory and osteoarthritis protective activities [47,48,49,50,51,52]. Diosgenin mainly exists in plant cells in the form of the ligand of saponin, with its C3 and C26 linked to sugar chains via saponin bonds [53]. Diosgenin naturally exists in tubers of many Dioscorea or Costus genus plants and seeds of T.foenum-graecum [54], but Discoreanipponica Makino (Dioscoreaceae), a tuberous herbaceous perennial liana, is widely used as materials for diosgenin production in industries [55]. It is also found in Smilax china L. (Smilacaceae), Heterosmilax japonica Kunth (Smilacaceae), Solanumincanum L. (Solanaceae), Solanum virginianum L. (Solanaceae), Cheilocostusspeciosus (J.Koenig) C.D.Specht (Costaceae) and T. foenum graecum. On the basis in vitro and in vivo studies, diosgenin and its analogs have roles in modulating important molecular targets and signaling pathways such as Phosphoinositide 3-kinase/Protein Kinase B/Mechanistic Target of Rapamycin (PI3K/AKT/mTOR), Janus Kinases/Signal Transducer and Activator of Transcription Proteins (JAK/STAT), Factor Nuclear Kappa B (NF-κB), and Mitogen-Activated Protein Kinase (MAPK), e.g., which have vital role in the development of various diseases [56]. It is a natural phytochemical which can mitigate diabetes induced oxidative stress and dyslipidemia which is important in cardio-metabolic risks by modulating the Peroxisome proliferator-activated receptor (PPARs) [57]. Diosgenin induces apoptosis inInsulin-like Growth Factor-1(IGF-1)-treated thyrocytes through two caspase pathways, namely inhibits FLICE inhibitory proteins (FLIP), and activates Caspase-8 in FAS related-pathway and increases Reactive Oxygen Species (ROS), regulates the ration of BCL2 Associated X/B-cell lymphoma 2 (BAX/BCL-2) in mitochondrial pathway [58]. Diosgenin ameliorated endothelial dysfunction through IκB kinase β/IR substrate 1-dependent manner (IKKβ/IRS-1), and improved endothelial insulin signaling under inflammatory conditions which shows its potential application in the treatment for atherosclerosis [59]. Diosgenin has the potential to show high glucose-induced renal proximal tubular fibrosis party by modulating Epithelial-to-Mesenchymal Transition (EMT) pathway [60]. Treatment by diosgenin may provide significant improvement toward preserving hemodynamic changes and alleviating oxidative stress, inflammatory and apoptotic markers induced by monocrotaline in rats and it also prevent monocrotaline-induced changes in nitric oxide production, endothelial and inducible nitric oxide synthase protein expression and histological analysis which shows its importance in pulmonary hypertension [61]. Diosgenin restored moderately decreased sperm motility in D-galactose-treated wistar males and it can be a choice for treatment of mild age-related reproductive dysfunctions [62]. It also shows antinociceptive potential in diabetic rats through lowering oxidative stress and inflammation and improving antioxidant defense system [63]. Zolfaghari et al. [64] reported that the induction of hairy roots considerably increased the production of diosgenin as compared with the plant itself, and they have found that by converting dioscin to diosgenin, the non-specific beta-glucosidase activity of bacterial genes may lead to higher accumulation of diosgenin in hairy roots of T. foenum-graecum. Diosgenin may inhibit melanogenesis through the activation of the Phosphatidylinositol-3-kinase (PI3K) pathway, and it may be considered as an effective inhibitor of hyperpigmentation [65]. Chemical structure of diosgenin has shown in Fig. 2. The most important pharmacological effects of diosgenin are shown in Table 2.

Fig. 2
figure 2

Chemical structure of diosgenin [44] (Jesus et al. 2016)

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Table 2 The most important pharmacological effects of diosgenin
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Conclusion

Traditional herbal medicines have been considered as a source of curative remedy due to health promote and prevent diseases, and plants are invaluable sources of new drugs. Galactomannans represent one of the most versatile classes of available materials for applications in many sectors specially pharmaceuticals. It is a group of storage polysaccharides from various plants which reserve energy for germination in the endosperm. They are with rigid hydrophilic backbone (polymannose, or mannan), and grafted galactose units. They are often used in various forms for human consumption. Four major sources of seed galactomannans are locust bean (Ceratonia siliqua), guar (Cyamopsis tetragonoloba), tara (Caesalpinia spinosa Kuntze), and fenugreek (T.foenum-graecum). The most important pharmacological benefits of galactomannan are antidiabetic, antioxidant, anticancer, anticholinesterase, antiviral activities, and appropriate for dengue virus and gastric diseases. A steroidal sapogenin, occurs in plants such as Dioscoreaalata, Smilax china, and T. foenum-graecum is diosgenin. Diosgenin, a triterpenoid having two pentacyclic rings. The most important health benefits of diosgenin are anti-diabetic, anti-inflammatory, anti-obesity, antioxidant, anti-proliferative, anti-psoriasis, anti-cancer, anti-tumour, and hepatoprotective effects; it can also improve female reproduction, multiple sclerosis, and appropriate for skin aging and wound healing.

Availability of data and materials

Not applicable.

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  1. Biotechnology Research Institute, Chinese Academy of Agricultural Sciences, Beijing, 100081, China

    Mohamad Hesam Shahrajabian, Wenli Sun & Qi Cheng

  2. PostgraduatePorgram in Biotechnology, University of Taquari Valley- Univates, Lajeado, RS, Brazil

    Diorge Jonatas Marmitt

  3. College of Life Sciences, Hebei Agricultural University, Baoding, 071000, Hebei, China

    Qi Cheng

  4. Global Alliance of HeBAU-CLS&HeQiS for BioAl-Manufacturing, Baoding, 071000, Hebei, China

    Qi Cheng

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Shahrajabian, M.H., Sun, W., Marmitt, D.J. et al. Diosgenin and galactomannans, natural products in the pharmaceutical sciences. Clin Phytosci 7, 50 (2021). https://doi.org/10.1186/s40816-021-00288-y

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