Investigation of Inclusion Complex of Patchouli Alcohol with β-Cyclodextrin

Xu, Fangfang; Yang, Qiuxia; Wu, Li-Lan; Qi, Rui; Wu, Yunshan; Li, Yucui; Tang, Lin; Guo, De‐An; Liu, Bo

doi:10.1371/journal.pone.0169578

Cited by 10 publications

(10 citation statements)

References 18 publications

(17 reference statements)

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“…The characteristic peaks of EV in the inclusion complex were completely vanished, indicating that the EV molecule was entirely inserted into the β-CD cavity (Figure 5E). 32−34 The FTIR spectrum of interaction of the FGF7:β-CD:EV complex shows the characteristic peak 1334 cm –1 of β-CD along with the characteristic peak 1532 cm –1 (strong N–O stretching) of FGF7 (Figure 5F).…”

Section: Resultsmentioning

confidence: 99%

“…FTIR studies indicate that a new structure was formed, and the EV molecule was entirely embedded into the β-CD cavity (Figure 5E) as the characteristic peaks of EV were completely vanished. 32−34 Furthermore, the interaction of FGF7 with the β-CD:EV inclusion complex was determined also. There was a shifting of the broad classic band of β-CD from 3295.22 to 3287 cm –1 , indicating a possibility of H-bonding between FGF7 and the inclusion complex as suggested by the molecular modeling scores (Figure 4).…”

Section: Discussionmentioning

confidence: 99%

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Molecular Modeling-_Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

et al. 2019

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Several studies have shown that the mammalian target of rapamycin (mTOR) inhibitor; everolimus (EV) improves patient survival in several types of cancer. However, the meaningful efficacy of EV as a single agent for the treatment of colorectal cancer (CRC) has failed to be proven in multiple clinical trials. Combination therapy is one of the options that could increase the efficacy and decrease the toxicity of the anticancer therapy. This study revealed that the β-cyclodextrin (β-CD):FGF7 complex has the potential to improve the antiproliferative effect of EV by preventing FGF receptor activation and by enhancing EV cellular uptake and intracellular retention. Molecular docking techniques were used to investigate the possible interaction between EV, β-CD, and FGF7. Molecular docking insights revealed that β-CD and EV are capable to form a stable inclusion complex with FGF at the molecular level. The aqueous solubility of the inclusion complex was increased (3.1 ± 0.23 μM) when compared to the aqueous solubility of pure EV (1.7 ± 0.16 μM). In addition, the in vitro cytotoxic activity of a FGF7:β-CD:EV complex on Caco-2 cell line was investigated using real-time xCELLigence technology. The FGF7:β-CD:EV complex has induced apoptosis of Caco-2 cells and shown higher cytotoxic activity than the parent drug EV. With the multitargets effect of β-CD:FGF7 and EV, the antiproliferative effect of EV was remarkably improved as the IC 50 value of EV was reduced from 9.65 ± 1.42 to 1.87 ± 0.33 μM when compared to FGF7:β-CD:EV complex activity. In conclusion, the findings advance the understanding of the biological combinational effects of the β-CD:FGF7 complex and EV as an effective treatment to combat CRC.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Molecular Modeling-_Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

et al. 2019

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“…PA will be transformed into β-patchoulene (β-PAE) in acid which suggested more powerful anti-inflammatory activity than PA (Junren et al, 2021). Studies have reported the use of β-cyclodextrin to encapsulate PA, improving its stability in vivo (Xu et al, 2017a), and lactoferrin has been used to deliver PA to inflammatory colonic macrophages that express LRP1, the receptor of lactoferrin (Zhao et al, 2020). Therefore, the application of these materials is expected to provide a mechanism to deliver PA to OCs.…”

Section: Discussionmentioning

confidence: 99%

Patchouli Alcohol Modulates the Pregnancy X Receptor/Toll-like Receptor 4/Nuclear Factor Kappa B Axis to Suppress Osteoclastogenesis

et al. 2021

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The incidence of osteoporosis, which is primarily characterized by plethoric osteoclast (OC) formation and severe bone loss, has increased in recent years. Millions of people worldwide, especially postmenopausal women, suffer from osteoporosis. The drugs commonly used to treat osteoporosis still exist many disadvantages, but natural extracts provide options for the treatment of osteoporosis. Therefore, the identification of cost-effective natural compounds is important. Patchouli alcohol (PA), a natural compound extracted from Pogostemon cablin that exerts anti-inflammatory effects, is used as a treatment for gastroenteritis. However, no research on the use of Patchouli alcohol in osteoporosis has been reported. We found that PA dose-dependently inhibited the receptor activator of nuclear factor kappa-B ligand (RANKL)-induced formation and function of OCs without cytotoxicity. Furthermore, these inhibitory effects were reflected in the significant effect of PA on the NF-κB signaling pathway, as PA suppressed the transcription factors NFATc1 and c-Fos. We also determined that PA activated expression of the nuclear receptor pregnane X receptor (PXR) and promoted the PXR/Toll-like receptor 4 (TLR4) axis to inhibit the nuclear import of NF-κB (p50 and p65). Additionally, PA exerted therapeutic effects against osteoporosis in ovariectomized (OVX) mice, supporting the use of PA as a treatment for osteoporosis in the future.

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“…Liao et al [40] verified the possibility using poloxamers (188 and 407) as solubility and dissolution rate enhancing agents of PA and suggested that the process of PA-SD pellets preparation was simple, rapid, cost effective, uncomplicated, and potentially scalable. Moreover, there was a communication on improving stability and dissolution rates of PA by complexing with β -cyclodextrin, which was confirmed by differential scanning calorimetry (DSC), Fourier transformation-infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD), and scanning electron microscope (SEM), respectively [41]. These efforts unambiguously could be an extremely inspiration of PA in pharmaceutical industry and medical practices.…”

Section: Pharmaceuticsmentioning

confidence: 91%

Availability, Pharmaceutics, Security, Pharmacokinetics, and Pharmacological Activities of Patchouli Alcohol

Hu¹,

Peng²,

Xie³

et al. 2017

Evidence-Based Complementary and Alternative Medicine

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Patchouli alcohol (PA), a tricyclic sesquiterpene, is one of the critical bioactive ingredients and is mainly isolated from aerial part of Pogostemon cablin (known as guanghuoxiang in China) belonging to Labiatae. So far, PA has been widely applied in perfume industries. This review was written with the use of reliable information published between 1974 and 2016 from libraries and electronic researches including NCKI, PubMed, Reaxys, ACS, ScienceDirect, Springer, and Wiley-Blackwell, aiming at presenting comprehensive outline of security, pharmacokinetics, and bioactivities of PA and at further providing a potential guide in exploring the PA and its use in various medical fields. We found that PA maybe was a low toxic drug that was acquired numerously through vegetable oil isolation and chemical synthesis and its stability and low water dissolution were improved in pharmaceutics. It also possessed specific pharmacokinetic characteristics, such as two-compartment open model, first-order kinetic elimination, and certain biometabolism and biotransformation process, and was shown to have multiple biological activities, that is, immunomodulatory, anti-inflammatory, antioxidative, antitumor, antimicrobial, insecticidal, antiatherogenic, antiemetic, whitening, and sedative activity. However, the systematic evaluations of preparation, pharmaceutics, toxicology, pharmacokinetics, and bioactivities underlying molecular mechanisms of action also required further investigation prior to practices of PA in clinic.

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Investigation of Inclusion Complex of Patchouli Alcohol with β-Cyclodextrin

Cited by 10 publications

References 18 publications

Molecular Modeling-_Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

Molecular Modeling-_Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

Patchouli Alcohol Modulates the Pregnancy X Receptor/Toll-like Receptor 4/Nuclear Factor Kappa B Axis to Suppress Osteoclastogenesis

Availability, Pharmaceutics, Security, Pharmacokinetics, and Pharmacological Activities of Patchouli Alcohol

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Investigation of Inclusion Complex of Patchouli Alcohol with β-Cyclodextrin

Cited by 10 publications

References 18 publications

Molecular Modeling-Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

Molecular Modeling-Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

Patchouli Alcohol Modulates the Pregnancy X Receptor/Toll-like Receptor 4/Nuclear Factor Kappa B Axis to Suppress Osteoclastogenesis

Availability, Pharmaceutics, Security, Pharmacokinetics, and Pharmacological Activities of Patchouli Alcohol

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Molecular Modeling-_Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells

Molecular Modeling-_Based Delivery System Enhances Everolimus-Induced Apoptosis in Caco-2 Cells