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Cytochalasins
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2014 · IF 3.107

Characterization of Cytochalasins from the Endophytic Xylaria sp. and Their Biological Functions

Qiang Zhang,Jian Xiao,Qing-Qing Sun,Jian-Chun Qin,Gennaro Pescitelli,Jin-Ming Gao

Bioassay-guided fractionation of the fermentation extract of Xylaria sp. XC-16, an endophyte from Toona sinensis led to the isolation of two new cytochalasans cytochalasin Z27, 1, and cytochalasin Z28, 2, along with three known compounds seco-cytochalasin E, 3, and cytochalasin Z18, 4, and cytochalasin E, 5. The structures of 1 and 2 were elucidated by spectroscopic and electronic circular dichroism methods. Compound 5 was shown to be potently cytotoxic against brine shrimp (LC50 = 2.79 μM), comparable to that of the positive agent toosendanin (LC50 = 4.03 μM), and also exhibited potential phytotoxic effects on Lactuca sativa and Raphanus sativus L. seedlings, which are higher than that of the positive control glyphosate. Additionally, the fungicidal effect of 2 against the phytopathogen Gibberella saubinetti was better than that of hymexazol. This is the first report of the three types of cytochalasins present in genus Xylaria. A structure–phytotoxicity activity relationship is also discussed.

CAS / MDL: 10004-44-1 10605-21-7
研究领域: 真菌学 · 天然产物化学 · 植物病理学
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BIOORGANIC CHEMISTRY · 2020 · IF 4.831

Cytochalasins from an endophytic fungus Phoma multirostrata XJ-2-1 with cell cycle arrest and TRAIL-resistance-overcoming activities

Xiaogang Peng,Yangzhou He,Ying Gao,Fangfang Duan,Juan Chen,Hanli Ruan

Nine new ( 1 – 9 ) and four known ( 10 – 13 ) [13]cytochalasins, along with three known 24-oxa[14]cytochalasins ( 14 – 16 ), were isolated from the culture of Phoma multirostrata XJ-2-1, an endophytic fungus obtained from the fibrous root of Parasenecio albus . Their structures were elucidated by interpretation of the nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS). The absolute configurations were assigned by single-crystal X-ray crystallography, modified Mosher′s method, and by analysis of their experimental electronic circular dichroism (ECD) spectra. Compound 6 could induce cell cycle arrest at G2-phase in CT26 and A549 cells, and displayed moderate cytotoxicity against CT26 and A549 cell lines with IC 50 values of 6.03 and 5.04 μM, respectively. Co-treatment of 7 – 9 , 13 and 16 with tumor necrosis factor related apoptosis inducing ligand (TRAIL) could significantly decrease the cell viability of A549, which revealed that cytochalasins could possibly be a new group of TRAIL sensitizers in lung cancer therapy.

研究领域: 药理学 · 生物化学 · 肿瘤学
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PLANTA MEDICA · 2022 ·Vol. 88 ·期 14 ·1299-1310 · IF 3.007

TRAIL-sensitizing Cytochalasins from the Endophytic Fungus Phoma multirostrata

Xiaogang Peng,Qianxi Ouyang,Jiao Pei,Jinling Chang,Chunlun Qin,Hanli Ruan

Seven undescribed cytochalasins, multirostratins K – Q (2–8), together with one known analogue, cytochalasin Z3 (1), were isolated from the culture of Phoma multirostrata XJ-2-1, an endophytic fungus obtained from the root of Parasenecio albus. Their structures with absolute configurations were determined by 1D and 2D NMR, high-resolution electrospray ionization mass spectrometry (HRESIMS), electronic circular dichroism (ECD), single-crystal X-ray crystallography, and chemical methods. The structure of ascochalasin was revised from Δ13 to Δ21 by detailed analysis of the NMR data and by comparison with the data for 7. In a TRAIL (tumor necrosis factor related apoptosis inducing ligand)-resistance-overcoming experiment, co-treatment of 2 or 6 with TRAIL reduced the cell viability of A549 cells by 30.3% and 27.5% at 10 µM, respectively.

研究领域: 药理学 · 有机化学 · 肿瘤学
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CHEMISTRY & BIODIVERSITY · 2025 · IF 2.5

Cytochalasinols A and B, Two New Cytochalasins From the Fungus Xylaria necrophora SZSS1-2-2

Qian Luo,Chen Sun,Xue Zhao,Er-Wei Li,Yu-Qing Yi,Yang Zhang,Shuai-Ming Zhu,Yu Yang,Rui Xu,Li-Xia Chen,You-Zhi Zhang,Chang-Wei Li

Two new cytochalasins ( 1 and 2 ) were isolated from the fermentation products of the fungus Xylaria necrophora SZSS1-2-2, along with nine known compounds: compound 3 , arbuschalasin B ( 4 ), cytochalasin C ( 5 ), cytochalasin D ( 6 ), 19,20-epoxycytochalasin C ( 7 ), 19,20-epoxycytochalasin D ( 8 ), cytochalasin R ( 9 ), cytochalasin D 13,14-epoxide ( 10 ), and arbuschalasin A ( 11 ). The structures and absolute configurations of these compounds were elucidated by spectroscopic analyses, electronic circular dichroism, and GIAO 13 C NMR computational methods. All isolated compounds were evaluated for their biological activities, and the results indicated that compounds 5 – 10 exhibited notable cytotoxic effects against the tested cell lines. However, none of the compounds showed antibacterial activity. Graphical

CAS / MDL: 51-21-8
研究领域: 天然产物化学 · 植物化学 · 微生物化学 · 药物化学 · 真菌学
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