A caryophyllane-type sesquiterpene, caryophyllenol A from Valeriana amurensis

Wu, Jinshan; Wang, Guang-Shu; Du, Xiaomei; Song, Ning; Zou, Zhong‐Mei; Chen, Jiashuai; Zhang, Yu; Ting-li, LI; Wang, Xijun; Kuang, Hai‐Xue

doi:10.1016/j.fitote.2014.03.025

Cited by 13 publications

(10 citation statements)

References 31 publications

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“…Caryophyllane sesquiterpenes are natural phytochemicals widely occurring in terrestrial plants and plant-associated fungal species [32][33][34][35][36][37], and are present in marine environments as secondary metabolites from the resident living organisms and microbes [38][39][40][41].…”

Section: Discussionmentioning

confidence: 99%

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Sotto

Irannejad

Eufemi

et al. 2020

IJMS

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Doxorubicin represents a valuable choice for different cancers, although the severe side effects occurring at the high effective dose limits its clinical use. In the present study, potential strategies to potentiate low-dose doxorubicin efficacy, including a metronomic schedule, characterized by a short and repeated exposure to the anticancer drug, and the combination with the natural chemosensitizing sesquiterpenes β-caryophyllene and β-caryophyllene oxide, were assessed in human hepatoma HepG2 cells. The involvement of P-glycoprotein (P-gp) in the HepG2-chemosensitization to doxorubicin was evaluated. Also, the direct interaction of caryophyllene sesquiterpenes with P-gp was characterized by molecular docking and dynamic simulation studies. A metronomic schedule allowed us to enhance the low-dose doxorubicin cytotoxicity and the combination with caryophyllane sesquiterpenes further potentiated this effect. Also, an increased intracellular accumulation of doxorubicin and rhodamine 123 induced by caryophyllane sesquiterpenes was found, thus suggesting their interference with P-gp function. A lowered expression of P-gp induced by the combinations, with respect to doxorubicin alone, was observed too. Docking studies found that the binding site of caryophyllane sesquiterpene was next to the ATP binding domain of P-gp and that β-caryophyllene possessed the stronger binding affinity and higher inhibition potential calculated by MM-PBSA. Present findings strengthen our hypothesis about the potential chemosensitizing power of caryophyllane sesquiterpenes and suggest that combining a chemosensitizer and a metronomic schedule can represent a suitable strategy to overcome drawbacks of doxorubicin chemotherapy while exploiting its powerful activity.Int. J. Mol. Sci. 2020, 21, 633 2 of 28 Int. J. Mol. Sci. 2020, 21, 633 5 of 28 oxide were selected for the combination experiments. Under our experimental conditions, both the sesquiterpenes were able to potentiate the effect of doxorubicin in different experimental conditions, although with different profiles. Particularly, after 24 h exposure, the lower chemosensitizing concentration (50 µM) of β-caryophyllene significantly enhanced the doxorubicin-cytotoxicity starting from the concentration of 10 µM, achieving almost the maximum potentiation of about 32% at concentration of 20 µM (Figure 2a).

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Section: Discussionmentioning

confidence: 99%

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Sotto

Irannejad

Eufemi

et al. 2020

IJMS

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“…С позиций доказательной медицины, интересными представляются результаты фундаменталь-ных исследований влияния фитотерапии на сон, прове-денные китайскими учеными в Хэйлунцзянском универ-ситете китайской традиционной медицины (Харбин, КНР) [51][52][53][54][55]. Ряд двойных слепых плацебоконтролируемых рандомизированных исследований показали высокую эффективность применения при нарушениях сна ком-плексных растительных препаратов, созданных на осно-ве традиционных китайских рецептов.…”

Section: мелатонин и нарушения сна у детейunclassified

“…Представители семейства валериановых, которое включает около 200 видов, произрастающих в Северной Америке, Азии и Европе, традиционно активно исполь-зуются в фитотерапии различных заболеваний нерв-ной системы у детей и взрослых [55]. Исследователями установлено, что валериана, наиболее часто применяе-мая в качестве седативного средства, содержит более 150 активных компонентов, которые определяют широкий спектр ее действия, и обеспечивают анксиолитический, противосудорожный и антиоксидантный эффекты [55].…”

Section: мелатонин и нарушения сна у детейunclassified

“…Исследователями установлено, что валериана, наиболее часто применяе-мая в качестве седативного средства, содержит более 150 активных компонентов, которые определяют широкий спектр ее действия, и обеспечивают анксиолитический, противосудорожный и антиоксидантный эффекты [55]. Исследование, проведенное в Хэйлунцзянском универ-ситете китайской традиционной медицины, посвященное выделению и изучению активных компонентов Valerianae amurensis (валерианы амурской), которая наиболее часто встречается в провинции Хэйлунцзян (Китай), показало, что седативный эффект валерианы, а также ее положи-тельное влияние на продолжительность и структуру сна обеспечивается соединениями, принадлежащими к груп-пе сесквитерпенов (в том числе и производные валериа-новой кислоты), при этом было выявлено 11 уже извест-ных сесквитерпенов, и выделены новые их представители (производные кариофиллена), обладающие высокой био-логической и фармакологической активностью [55].…”

Section: мелатонин и нарушения сна у детейunclassified

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Integrated Diagnostics and Correction of Sleep Disorders in Children

Nemkova¹,

Заваденко²,

Li³

et al. 2015

PPh

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“…This herb has also been used to treat dementia in Mongolian preparations for a long time [12]. From the roots and rhizomes of V. amurensis, iridoid glycosides, monoterpeneglucosides, phenylpropanoids glycosides, sesquiterpenoids, triterpenoids, lignans and phenolic acids have been isolated [9][10][11][12][13][14]. The chemical composition of the essential oils derived from V. amurensis has also been determined [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Gas Chromatography-Mass Spectrometric Analysis of Nematicidal Essential Oil ofValeriana amurensis P Smirn ex Kom (Valerianaceae) Roots and its Activity against Heterodera avenae

Li¹,

Ji²,

Li³

2015

Trop. J. Pharm Res

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Purpose: To investigate the chemical composition and nematicidal activity of the essential oil of Valeriana amurensis roots against cereal cyst nematodes (Heterodera avenae).Methods: The essential oil of V. amurensis roots was obtained by hydrodistillation and analyzed by gas chromatography (GC) and gas chromaotography-mass spectrometry (GC-MS). The nematicidal activity of the essential oil and its major constituents was determined against second stage juveniles of H. avenae.Results: A total of 33 components of the essential oil were identified. The major constituents were bornyl acetate (12.5 %), patchoulol (11.6 %), caryophyllene (8.2 %), 3-methylvaleric acid (7.3 %) and isovaleric acid (6.5 %). The essential oil exhibited nematicidal activity against H. avenae with a medium lethal concentration (LC50) value of 311.6 μg/mL. The major constituents, isovaleric acid and 3- methylvaleric acid, exhibited nematicidal activity against H. avenae with LC50 of 218.2 and 683.8 μg/mL, respectively.Conclusion: The study indicates that the essential oil of V. amurensis roots and its two major constituents, isovaleric acid and 3-methylvaleric acid, have a potential to be developed to natural nematicides for the control of cereal cyst nematodes.Keywords: Valeriana amurensis, Heterodera avenae, Nematicidal activity, Isovaleric acid, 3- Methylvaleric acid, Essential oil, Cereal cyst nematodes

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A caryophyllane-type sesquiterpene, caryophyllenol A from Valeriana amurensis

Cited by 13 publications

References 31 publications

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Potentiation of Low-Dose Doxorubicin Cytotoxicity by Affecting P-Glycoprotein through Caryophyllane Sesquiterpenes in HepG2 Cells: an in Vitro and in Silico Study

Integrated Diagnostics and Correction of Sleep Disorders in Children

Gas Chromatography-Mass Spectrometric Analysis of Nematicidal Essential Oil ofValeriana amurensis P Smirn ex Kom (Valerianaceae) Roots and its Activity against Heterodera avenae

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