Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Li, Yan; Li, Chengwei; Cui, Cheng‐Bin; Liu, Xingzhong; Che, Yongsheng

doi:10.1007/s13659-012-0018-z

Cited by 26 publications

(21 citation statements)

References 35 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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“…was isolated from a soil sample that was collected at Linzhi, Tibet, China. Our initial investigation of this fungus that was fermented in rice medium at 25°C led to the isolation of three antimicrobial caryophyllene-derived meroterpenoids [ 14 , 15 ] and three cytotoxic caryophyllene sesquiterpenoids [ 16 ]. In the current work, the fungus was refermented in the same solid culture medium at 15°C, and the HPLC chromatogram of the crude extract revealed the presence of additional components.…”

Section: Introductionmentioning

confidence: 99%

Punctaporonins N–S, New Caryophyllene Sesquiterpenoids from Cytospora sp.

Wang²,

Liu

et al. 2017

BioMed Research International

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Six new caryophyllene sesquiterpenoids, punctaporonins N–S (1–6), and three known ones, 6-hydroxypunctaporonins B (7), A (8), and E (9), have been isolated from solid cultures of Cytospora sp. The structures of 1–6 were elucidated primarily by NMR spectroscopy. The absolute configuration of 1 was assigned by X-ray crystallographic analysis of its S-MTPA ester. Compounds 2, 5, and 6 showed modest cytotoxicity against HeLa cells.

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“…(Deyrup et al, 2006;Pulici et al, 1996), fuscoatrol A from Humicola fuscoatra (Smetanina et al, 2004), Sch 725432, Sch 601253, Sch 601254, and Sch 725434 from Chrysosporium pilosum (Yang et al, 2009), cytosporinols from Cytospora sp. (Li et al, 2012), and punctaporonins H -M from Hansfordia sinuosae (Wu et al, 2014). Despite the unique and diverse chemistry associated with these compounds, their biological properties have been of limited interest to date, though some pestalotiopsins show immunosuppressive and cytotoxic activities and punctaporonin K reduces triglycerides and total cholesterol levels in cells (Pulici et al, 1996;Wu et al, 2014;Takao et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

New punctaporonins from two fungicolous isolates of Pestalotiopsis sp.

Hwang

Wicklow

Gloer

2016

Phytochemistry Letters

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Seven new caryophyllene sesquiterpenoids (5-11) were isolated during investigation of two fungicolous isolates of Pestalotiopsis sp. and identified as punctaporonin analogues. The structures of these compounds were mainly assigned by analysis of NMR and HRMS data. Compounds 5, 6, and 7 are 13-hydroxy analogues of 6-hydroxypunctaporonins A, B, and E, respectively, and compound 8 is a 6-hydroxy analogue of punctaporonin D. Compounds 9 and 11 are ketone-containing analogues of 6-hydroxypunctaporonin A and fuscoatrol A, respectively, and compound 10 is a 9-methoxy derivative of 8. The names punctaporonins N, O, and P are proposed for compounds 9, 10, and 11, respectively. Antibacterial activity associated with the extract was attributed to the presence of known punctaporonins as major metabolites.

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Cytosporinols A-C, new caryophyllene sesquiterpenoids from Cytospora sp.

Cited by 26 publications

References 35 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

Punctaporonins N–S, New Caryophyllene Sesquiterpenoids from Cytospora sp.

New punctaporonins from two fungicolous isolates of Pestalotiopsis sp.

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