Dataset Information

Selective cytotoxic eremophilane-type sesquiterpenes from Penicillium citreonigrum.

ABSTRACT: One new eremophilane-type sesquiterpene (1, citreopenin) was isolated from Penicillium citreonigrum (HQ738282), and the structure was elucidated by a combination of spectroscopic data interpretation and single-crystal X-ray diffraction analysis using Cu K? radiation (CCDC 1030588). Compound 1 showed weak activity against KB-VIN (IC50 = 11.0 ± 0.156 ?M), while the known compound 3 exhibited selective cytotoxicity against MDA-MB-231 triple-negative breast cancer (TNBC) (IC50 = 5.42 ± 0.167 ?M).

SUBMITTER: Yuan WH

PROVIDER: S-EPMC4878012 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Selective cytotoxic eremophilane-type sesquiterpenes from Penicillium citreonigrum.

Yuan Wei-Hua WH Goto Masuo M Hsieh Kan-Yen KY Yuan Bo B Zhao Yu Y Morris-Natschke Susan L SL Lee Kuo-Hsiung KH

Journal of Asian natural products research 20151214 12

One new eremophilane-type sesquiterpene (1, citreopenin) was isolated from Penicillium citreonigrum (HQ738282), and the structure was elucidated by a combination of spectroscopic data interpretation and single-crystal X-ray diffraction analysis using Cu Kα radiation (CCDC 1030588). Compound 1 showed weak activity against KB-VIN (IC50 = 11.0 ± 0.156 μM), while the known compound 3 exhibited selective cytotoxicity against MDA-MB-231 triple-negative breast cancer (TNBC) (IC50 = 5.42 ± 0.167 μM). ...[more]

PMID: 26666171

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Project description:Dendritic cell (DC) activation induces expression of co-stimulatory surface molecules, as well as migration into secondary lymphoid organs, where they activate naïve T-cells. A family of plant derivatives, eremophilane-type petasite sesquiterpenes, can regulate the immune system through DC targeting due to their anti-inflammatory effects. Peroxisome proliferator-activated receptor gamma (PPAR?) is involved in inhibition of inflammatory responses and induction of DCs to acquire a mucosal phenotype. Since mucosal DCs are central in innate immune responses, we hypothesized that eremophilane-type petasite sesquiterpenes exerted their anti-inflammatory effects by inhibiting DC maturation and activation through PPAR?. This study assessed the bicyclic eremophilane-type petasite sesquiterpene compounds Fukinone and 10?H-8?,12-Epidioxyeremophil-7(11)-en-8?-ol (ZYFDC21 and ZYFDC22) in the maturation and activation of mouse DC. We measured surface expression of co-stimulatory molecules by flow cytometry and cell-free supernatant cytokine production upon lipopolysaccharide stimulation by enzyme-linked immunosorbent assays (ELISAs) in the presence or absence of PPAR? agonists. DCs were generated from C57BL/6 mice bone marrow cells and harvested. Cells were exposed to bicyclic eremophilane-type petasite sesquiterpenes ZYFDC21 or ZYFDC22 in the presence or absence of synthetic PPAR? agonists (GW1929 and TGZ) or the natural PPAR? ligand 15d-PGJ2, followed by overnight activation with LPS. We observed differences in the upregulation of surface expression of CD86, along with TNF, IL-6, and IL-12p70 released by DCs stimulated with LPS, when using combinations of bicyclic eremophilane-type petasite sesquiterpenes ZYFDC21 or ZYFDC22, and PPAR? agonists, in particular the PPAR? ligand 15d-PGJ2. Our results indicate that bicyclic eremophilane-type petasite sesquiterpenes ZYFDC21 or ZYFDC22 inhibit maturation and activation of DC, and this activity is augmented upon PPAR? activation.

Dataset Information

Selective cytotoxic eremophilane-type sesquiterpenes from Penicillium citreonigrum.

Publications

Selective cytotoxic eremophilane-type sesquiterpenes from Penicillium citreonigrum.

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