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来自中国南海海绵叶状卡特海绵的细胞毒性半日花烷型倍半萜

Cytotoxic scalarane sesterterpenoids from the South China Sea sponge Carteriospongia foliascens.

作者信息

Cao Fei, Wu Ze-Hong, Shao Chang-Lun, Pang Sen, Liang Xiao-Yan, de Voogd Nicole J, Wang Chang-Yun

机构信息

Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.

出版信息

Org Biomol Chem. 2015 Apr 7;13(13):4016-24. doi: 10.1039/c4ob02532f.

Abstract

Eleven new scalarane sesterterpenoids, including three 20,24-bishomo-25-norscalaranes, carteriofenones A–C (1–3), and eight 20,24-bishomoscalaranes, carteriofenones D–K (4–11), along with two known analogues (12 and 13), were obtained from the marine sponge Carteriospongia foliascens collected from the South China Sea. Their planar structures and relative configurations were elucidated by extensive NMR spectroscopic data. The absolute configuration of 3 was determined using the modified Mosher's method on its hydrolysis product. Scalarane sesterterpenoids with 4-methylpentanate or pentanoate substituents at the 12-position (1–8) were reported for the first time. Carteriofenones E–H (5–8) represented rare naturally occurring scalarane sesterterpenoids with a cyclobutane ring. Compound 4 showed cytotoxicity against the mouse lymphocytic leukemia cell line (P388) with an IC50 value of 0.96 μM.

摘要

从中国南海采集的叶状卡特海绵(Carteriospongia foliascens)中获得了11种新的四环三萜倍半萜类化合物,包括3种20,24-双高-25-降四环三萜类化合物,卡特芬酮A - C(1 - 3),以及8种20,24-双高四环三萜类化合物,卡特芬酮D - K(4 - 11),还有两种已知类似物(12和13)。通过广泛的核磁共振光谱数据阐明了它们的平面结构和相对构型。利用改良的莫舍尔方法对3的水解产物确定了其绝对构型。首次报道了在12位具有4-甲基戊酸酯或戊酸酯取代基的四环三萜倍半萜类化合物(1 - 8)。卡特芬酮E - H(5 - 8)代表了罕见的具有环丁烷环的天然四环三萜倍半萜类化合物。化合物4对小鼠淋巴细胞白血病细胞系(P388)显示出细胞毒性,IC50值为0.96μM。

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