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生物测定指导下的水果中细胞毒性化合物的分离与鉴定

Bioassay-Guided Isolation and Identification of Cytotoxic Compounds from Fruits.

作者信息

Raksat Achara, Atanu Md Samiul Huq, Mendez Sheyanne, Zerda Rafael de la, Sun Rui, Cheenpracha Sarot, Wall Marisa, Simmons Charles J, Williams Philip G, Tan Ghee T, Wongwiwatthananukit Supakit, Chang Leng Chee

机构信息

Department of Pharmaceutical Sciences, The Daniel K. Inouye College of Pharmacy, University of Hawai'i at Hilo, Hilo, Hawaii 96720, United States.

X-ray Diffraction Laboratory, Department of Chemistry, University of Hawai'i at Hilo, 200 West Kawili Street, Hilo, Hawai'i 96720, United States.

出版信息

ACS Omega. 2024 Apr 11;9(16):18516-18525. doi: 10.1021/acsomega.4c00769. eCollection 2024 Apr 23.

DOI:10.1021/acsomega.4c00769
PMID:38680310
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11044245/
Abstract

The fruit extract of yielded a total of 19 compounds, including two novel spiro-biflavonoid enantiomers ( and ) and a chalcone derivative (). Their structures were determined through spectroscopic analysis. The enantiomers of the racemic mixture of compound were successfully resolved into (+)- and (-)- using chiral-phase HPLC. Single-crystal X-ray diffraction analysis was also used to confirm the structure of . The enantiomeric configurations of and were determined through a comparison of the calculated and experimental electronic circular dichroism spectra. Compounds (melanervin), (methyl betulinate), (3--acetylbetulinic acid), and (pyracrenic acid) were found to be highly cytotoxic, with compound showing superior growth inhibition of nonsmall cell lung cancer cells (A549 cells) (IC 2.8 ± 0.1 μM) compared to cisplatin (IC 3.3 ± 0.0 μM), a positive control chemotherapeutic drug. Both compound and cisplatin were significantly more cytotoxic toward A549 lung cancer cells compared to nontumorigenic Vero E6 cells.

摘要

[某种植物]的果实提取物共得到19种化合物，包括两种新型螺二黄酮对映体（[化合物名称1]和[化合物名称2]）以及一种查尔酮衍生物（[化合物名称3]）。通过光谱分析确定了它们的结构。化合物[外消旋混合物名称]的对映体通过手性相高效液相色谱成功拆分为(+)-和(-)-[对映体名称]。单晶X射线衍射分析也用于确认[化合物名称3]的结构。通过比较计算和实验电子圆二色光谱确定了[化合物名称1]和[化合物名称2]的对映体构型。发现化合物[化合物名称4]（黑脉菌素）、[化合物名称5]（桦木酸甲酯）、[化合物名称6]（3-[取代基] - 乙酰桦木酸）和[化合物名称7]（焦曲霉酸）具有高度细胞毒性，与阳性对照化疗药物顺铂（IC 3.3 ± 0.0 μM）相比，化合物[化合物名称4]对非小细胞肺癌细胞（A549细胞）表现出更强的生长抑制作用（IC 2.8 ± 0.1 μM）。与非致瘤性Vero E6细胞相比，化合物[化合物名称4]和顺铂对A549肺癌细胞的细胞毒性均显著更高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/fb91529cefca/ao4c00769_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/f52adbb0632e/ao4c00769_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/bc0db8ff7ce2/ao4c00769_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/08ad49cb3085/ao4c00769_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/53abdbc04f6e/ao4c00769_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/c4504de8e892/ao4c00769_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/1f6d7d66884b/ao4c00769_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/fb91529cefca/ao4c00769_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/f52adbb0632e/ao4c00769_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/bc0db8ff7ce2/ao4c00769_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/08ad49cb3085/ao4c00769_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/53abdbc04f6e/ao4c00769_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/c4504de8e892/ao4c00769_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/1f6d7d66884b/ao4c00769_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5fea/11044245/fb91529cefca/ao4c00769_0007.jpg

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