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Higginsianins D and E, Cytotoxic Diterpenoids Produced by Colletotrichum higginsianum.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-19 , DOI: 10.1021/acs.jnatprod.9b01161 Marco Masi , Alessio Cimmino , Flora Salzano , Roberta Di Lecce , Marcin Górecki 1, 2 , Viola Calabrò , Gennaro Pescitelli 1 , Antonio Evidente
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-19 , DOI: 10.1021/acs.jnatprod.9b01161 Marco Masi , Alessio Cimmino , Flora Salzano , Roberta Di Lecce , Marcin Górecki 1, 2 , Viola Calabrò , Gennaro Pescitelli 1 , Antonio Evidente
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Two new diterpenoids with tetrasubstituted 3-oxodihydrofuran substituents, named higginsianins D (1) and E (2), were isolated from the mycelium of the fungus Colletotrichum higginsianum grown in liquid culture. They were characterized as methyl 2-[6-hydroxy-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-decahydronaphthalen-1-ylmethyl]-4,5-dimethyl-3-oxo-2,3-dihydrofuran-2-carboxylate and its 21-epimer by using NMR, HRESIMS, and chemical methods. The relative configurations of higginsianins D and E, which did not afford crystals suitable for X-ray analysis, were determined by NOESY experiments and by comparison with NMR data of higginsianin B. The absolute configuration was established by comparison of experimental and calculated electronic circular dichroism data. The evaluation of 1 and 2 for antiproliferative activity against human A431 cells derived from epidermoid carcinoma and H1299 non-small-cell lung carcinoma cells revealed that 2 exhibited higher cytotoxic activity than 1, with an IC50 value of 1.0 μM against A431 cells. Remarkably, both 1 and 2 were almost ineffective against immortalized keratinocytes, used as a preneoplastic cell line model.
中文翻译：
Higginsianins D和E，由炭疽菌（Colletotrichum higginsianum）生产的细胞毒性二萜类化合物。
从液态培养的真菌炭疽菌菌丝体中分离出两个新的具有四取代的3-氧二氢呋喃取代基的二萜类化合物，分别命名为希金斯菌素D（1）和E（2）。它们被表征为甲基2- [6-羟基-5,8a-二甲基-2-亚甲基-5-（4-甲基戊-3-烯基）-十氢萘-1-基甲基] -4,5-二甲基-3-氧代。 -2,3-二氢呋喃-2-羧酸酯及其21位异构体，采用NMR，HRESIMS和化学方法制备。通过NOESY实验并通过与希金斯宁B的NMR数据比较，确定了没有提供适合X射线分析的晶体的希金斯宁D和E的相对构型。通过比较实验和计算的电子圆二色性，确定了绝对构型数据。评估1和2对源自表皮样癌和H1299非小细胞肺癌细胞的人A431细胞的抗增殖活性，发现2与1相比具有更高的细胞毒活性，对A431细胞的IC50值为1.0μM。值得注意的是，1和2对永生化的角质形成细胞（用作肿瘤前细胞系模型）几乎无效。
更新日期：2020-03-19
中文翻译：
Higginsianins D和E，由炭疽菌（Colletotrichum higginsianum）生产的细胞毒性二萜类化合物。
从液态培养的真菌炭疽菌菌丝体中分离出两个新的具有四取代的3-氧二氢呋喃取代基的二萜类化合物，分别命名为希金斯菌素D（1）和E（2）。它们被表征为甲基2- [6-羟基-5,8a-二甲基-2-亚甲基-5-（4-甲基戊-3-烯基）-十氢萘-1-基甲基] -4,5-二甲基-3-氧代。 -2,3-二氢呋喃-2-羧酸酯及其21位异构体，采用NMR，HRESIMS和化学方法制备。通过NOESY实验并通过与希金斯宁B的NMR数据比较，确定了没有提供适合X射线分析的晶体的希金斯宁D和E的相对构型。通过比较实验和计算的电子圆二色性，确定了绝对构型数据。评估1和2对源自表皮样癌和H1299非小细胞肺癌细胞的人A431细胞的抗增殖活性，发现2与1相比具有更高的细胞毒活性，对A431细胞的IC50值为1.0μM。值得注意的是，1和2对永生化的角质形成细胞（用作肿瘤前细胞系模型）几乎无效。
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