Bakuchiol – a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches

Krishna, T. P. Adarsh; Baldev, E.; Athalathil, Sunil

doi:10.1039/d1ra08771a

Cited by 25 publications

(11 citation statements)

References 153 publications

(117 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Additionally, the compound of retention time at 19.7 min might be bakuchiol. Bakuchiol is the major component of essential oil from PF ( Adarsh Krishna et al, 2022 ). Although liposoluble components including bakuchiol were removed by in PFPE preparation, the content of bakuchiol was considerable high in PFPE.…”

Section: Discussionmentioning

confidence: 99%

Isobavachalcone From Cullen corylifolium Presents Significant Antibacterial Activity Against Clostridium difficile Through Disruption of the Cell Membrane

et al. 2022

View full text Add to dashboard Cite

Background:Clostridium difficile infection (CDI) has been widely reported in human and animals around the world over the past few decades. The high relapse rate and increasing drug resistance of CDI make the discovery of new agents against C. difficile fairly urgent. This study aims to investigate the antibacterial activity against C. difficile from traditional Chinese herb medicine Cullen corylifolium and confirm its active components.Methods: Phenolic extract from the seeds of C. corylifolium was prepared routinely and the contents of relative flavonoids were determined by High Performance Liquid Chromatography (HPLC). In vitro antibacterial activities of the phenolic extract and its major components were tested. The influence of the major components on cell membrane was investigated with membrane integrity by SEM and propidium iodid uptake assay. Cytotoxicity of the extract and its active compounds on Caco-2 cell line was assessed by CCK-8 kit. The in vivo therapeutic efficacy of IBCL was evaluated on the mice model.Results: Phenolic extract was found to be active against C. difficile with minimum inhibitory concentrations (MIC) of 8 μg/mL. As the major component of the extract, IBCL was the most active compound against C. difficile. The MIC of IBCL and 4MBCL were 4 μg/ml and 4 μg/ml, respectively. Meanwhile, PFPE, IBCL, and 4MBCL showed rapid bactericidal effect against C. difficile in 1 h, which was significant compared to antibiotic vancomycin. Mechanism studies revealed that IBCL can disrupt the integrity of the cell membrane, which may lead to the death of bacteria. PFPE was low cytotoxic against Caco-2 cells, and the cytotoxicity of IBCL and 4MBCL were moderate. Symptoms of CDI were effectively alleviated by IBCL on the mice model and weight loss was reduced. From death rates, IBCL showed better efficacy compared to vancomycin at 50 mg/kg dosage.Conclusion: As the major component of phenolic extract of C. corylifolium seeds, IBCL showed significant antibacterial activity against C. difficile in vitro and rapidly killed the bacteria by disrupting the integrity of the cell membrane. IBCL can significantly prevent weight loss and reduce death caused by CDI on the mice model. Therefore, IBCL may be a promising lead compound or drug candidate for CDI.

show abstract

Section: Discussionmentioning

confidence: 99%

Isobavachalcone From Cullen corylifolium Presents Significant Antibacterial Activity Against Clostridium difficile Through Disruption of the Cell Membrane

et al. 2022

View full text Add to dashboard Cite

show abstract

“…97–100 So this approach is an efficient way to quickly generate new chemical entities on a lead molecule without resorting to de novo synthesis. There are several late-stage diversification approaches in many natural products, such as estrone, 101 resveratrol, 102 artemisinin, 103 juglone, 104 bakuchiol, 105 vitamin K 3 , 106 and curcumin, 107 were reported in the literature.…”

Section: Structural Modification and Improved Activitiesmentioning

confidence: 99%

Guggulsterone – a potent bioactive phytosteroid: synthesis, structural modification, and its improved bioactivities

Adarsh Krishna,

Ajeesh Krishna,

Edachery

et al. 2024

RSC Med. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…While psoralens may be beneficial when used for conditions such as vitiligo or psoriasis when used in conjunction with phototherapy, when used for facial care, the presence of psoralens can have unintended effects by causing psoralen‐based photosensitivity. For this reason, the use of an isolated and purified compound such as bakuchiol may eliminate this risk 5 . Furthermore, the leaf, root, and stems of P .…”

Section: Finding the Right Bakuchiol: Choose Wiselymentioning

confidence: 99%

Finding the right Bakuchiol: Choose wisely

Afzal

Sivamani

2023

J of Cosmetic Dermatology

View full text Add to dashboard Cite

Bakuchiol – a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches

Abstract: The isolation methods, various chemical routes and late-stage functionalization approaches and structure–activity relationships of bakuchiol – a meroterpene class of natural product has been discussed in detail.

Cited by 25 publications

References 153 publications

Isobavachalcone From Cullen corylifolium Presents Significant Antibacterial Activity Against Clostridium difficile Through Disruption of the Cell Membrane

Isobavachalcone From Cullen corylifolium Presents Significant Antibacterial Activity Against Clostridium difficile Through Disruption of the Cell Membrane

Guggulsterone – a potent bioactive phytosteroid: synthesis, structural modification, and its improved bioactivities

Finding the right Bakuchiol: Choose wisely

Contact Info

Product

Resources

About