Diterpenoid lead stevioside and its hydrolysis products steviol and isosteviol: Biological activity and structural modification

Wang, Mingying; Li, He; Xu, Fanxing; Gao, Xiang; Li, Jia; Xu, Shengtao; Zhang, Dayong; Wu, Xiaoming; Xu, Jinyi; Hua, Hui‐Ming; Li, Dahong

doi:10.1016/j.ejmech.2018.07.052

Cited by 54 publications

(47 citation statements)

References 173 publications

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“…As reported by Amin [10] and Habbu et al [11], U. lactuca contains secondary metabolites in the form of alkaloids, triterpenoids, steroids, saponins, phenolic compounds, and flavonoids, which are useful as antimicrobial agents (Table -2) [13,[37][38][39][40][41][42]. The benefits of U. lactuca can be seen in Table -3 [42][43][44][45][46][47], including antioxidant, antimicrobial, antiviral, antihyperlipidemic, antitumor, anti-inflammatory, antibiofilm, and anticoagulant activities [13,[43][44][45][46][47][48].…”

Section: Benefits Of Green Algae (U Lactuca)mentioning

confidence: 97%

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Potential antimicrobial properties of the Ulva lactuca extract against methicillin-resistant Staphylococcus aureus-infected wounds: A review

et al. 2021

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Methicillin-resistant Staphylococcus aureus (MRSA), currently a major problem in hospitals worldwide, is one of the most common causes of nosocomial disease through surgical wound infection. MRSA-infected wounds have very low recovery rates and have become more problematic as some antibiotics are not effective against MRSA. Several antimicrobial and anti-inflammatory agents of green algae (Ulva lactuca) in the form of alkaloids, triterpenoids, steroids, saponins, and flavonoids have the potential to accelerate the wound healing process following MRSA wound infection. Various active compounds contained in the U. lactuca extract are thought to have multiple antibacterial and anti-inflammatory properties that can overcome the MRSA antimicrobial resistance and accelerate tissue growth in the wound healing process. This review aims to describe the potential of Ulva lactuca extract against MRSA-infected wound healing.

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Section: Benefits Of Green Algae (U Lactuca)mentioning

confidence: 97%

“…These marine algae compounds may affect multiple targets in the immune and inflammatory systems that influence disease progression [43]. U. lactuca contains active compounds such as saponins, terpenoids, and flavonoids that function as anti-inflammatory agents [38][39][40]64].…”

Section: Potential Of U Lactuca As An Antiinflammatory Agent In Wound Healingmentioning

confidence: 99%

Potential antimicrobial properties of the Ulva lactuca extract against methicillin-resistant Staphylococcus aureus-infected wounds: A review

et al. 2021

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“…Some steviol derivatives that have substituted the carboxylic function with an amino group at the C-4 position possess inhibitory effects against Hepatitis B virus (Figure 1, IV) [31]. In recent years, several reviews have disclosed thorough discussions about the syntheses of steviol-based polyols [28,32], or even more complex structures [25,33,34]. It is important to note that, in most cases, acid sensitivity and the rapid rearrangement of the ent-kaurane ring system were mentioned as the limitation of transformations.…”

Section: Int J Mol Sci 2020 20 X For Peer Review 2 Of 20mentioning

confidence: 99%

Stereoselective Synthesis and Antiproliferative Activity of Steviol-Based Diterpen Aminodiols

Nagy

Zupkó

Szakonyi

2019

IJMS

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A library of steviol-based trifunctional chiral ligands was developed from commercially available natural stevisoide and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The key intermediate steviol methyl ester was prepared according to literature procedure. Depending on the epoxidation process, both cis- and trans-epoxyalcohols were obtained. Subsequent oxirane ring opening with primary and secondary amines afforded 3-amino-1,2-diols. The ring opening with sodium azide followed by a “click” reaction with alkynes resulted in dihydroxytriazoles. The regioselective ring closure of N-substituted aminodiols with formaldehyde was also investigated. The resulting steviol-type aminodiols were tested against a panel of human adherent cancer cell lines (A2780, SiHa, HeLa, and MDA-MB-231). It was consistently found that the N-benzyl substituent is an essential part within the molecule and the ring closure towards N-benzyl substituted oxazolidine ring system increased the antiproliferative activity to a level comparable with that of cisplatine. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol systems.

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“…The highly purified preparations of stevioside (≥95%) meet the U.S. Food and Drug Administration standard for being classified “Generally Recognized as Safe” (Urban et al., 2015). Stevioside is a natural diterpenoid steviol glycoside containing a hydrophobic part with a diterpenoid or steviol backbone, and a hydrophilic part with glucosyl and sophorosyl residues (Wang et al., 2018). The structures of stevioside molecules are similar to those of triterpenoid saponins and can enhance the solubility of several pharmaceutically and medically important compounds with poor water solubility (Nguyen et al., 2017).…”

Section: Introductionmentioning

confidence: 99%

Preparation, optimization, characterization, and in vitro bioaccessibility of a lutein microparticle using spray drying with β‐cyclodextrin and stevioside

Dai

et al. 2020

J Food Process Preserv

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In this study, the powder of a lutein microparticle was prepared by spray drying with amphiphilic stevioside and β‐cyclodextrin as coating materials was developed to improve the solubility and bioaccessibility of lutein. Response surface methodology was used to optimize the preparation process with the drug loading capacity as index, indicating the optimal spray drying conditions were obtained as follows: feed rate of 500 ml h−1, inlet air temperature of 180°C, lutein amount of 649.4 mg, stevioside amount of 596.4 mg, and β‐cyclodextrin of 2,591.1 mg. The highest lutein loading capacity obtained was 325.7 mg g−1, resulting in high in vitro bioaccessibility of lutein (increased by twofold), which attributed to the increased solubilization capacity. The optimized lutein microparticle powders appeared spherical agglomerated structure under SEM, DSC analysis showed that the partial structure of lutein interacted with stevioside and was encapsulated by β‐cyclodextrin, FT‐IR result showed that noncovalent interactions mainly occurred between lutein and the carriers. The results suggested that the above lutein microencapsules could exhibit good potential for the bioavailability of lutein. Practical applications Lutein has widely gained considerable popularity as a food additive. To improve the solubility and bioaccessibility of lutein, lutein microparticle was successfully encapsulated with stevioside and β‐cyclodextrin by spray drying. A method for optimizing encapsulation conditions of high loading lutein microparticle powder using Box–Behnken design was studied. The result of this study can be useful for process optimization and has a significant effect on developing higher bioaccessibility for the product of lutein.

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Diterpenoid lead stevioside and its hydrolysis products steviol and isosteviol: Biological activity and structural modification

Cited by 54 publications

References 173 publications

Potential antimicrobial properties of the Ulva lactuca extract against methicillin-resistant Staphylococcus aureus-infected wounds: A review

Potential antimicrobial properties of the Ulva lactuca extract against methicillin-resistant Staphylococcus aureus-infected wounds: A review

Stereoselective Synthesis and Antiproliferative Activity of Steviol-Based Diterpen Aminodiols

Preparation, optimization, characterization, and in vitro bioaccessibility of a lutein microparticle using spray drying with β‐cyclodextrin and stevioside

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