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New Mono- and Dimeric Members of the Secalonic Acid Family: Blennolides ACG Isolated from the Fungus Blennoria sp.

机译:二十碳五烯酸家族的新的单体和二聚体成员:从真菌Blennoria sp。分离的Blennolides ACG。

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摘要

Blennolides ACG (2C8), seven unusual chromanones, were isolated together with secalonic acid B (1) from Blennoria sp., an endophytic fungus from Carpobrotus edulis. This is the first reported isolation of the blennolides 2 and 3 (hemisecalonic acids B and E), the existence of which as the monomeric units of the dimeric secalonic acids had long been postulated. A compound of the proposed structure 4 (b-diversonolic ester) will need to be revised, as its reported data do not fit those of the established structure of blennolide C (4). Other monomers, the blennolides DCF (5C7) seem to be derived from blennolides A (2) and B (3) by rearrangement of the hydroaromatic ring. The heterodimer 8, composed of the monomeric blennolide A (2) and the rearranged 11-dehydroxy derivative of blennolide E (6), extends the ergochrome family with an ergoxanthin type of skeleton. The structures of the new compounds were elucidated by detailed spectroscopic analysis and further confirmed by an X-ray diffraction study of a single crystal of 2. The absolute configurations were determined by TDDFT calculations of CD spectra, including the solid-state CD/TDDFT approach. Preliminary studies showed strong antifungal and antibacterial activities of these compounds against Microbotryum violaceum and Bacillus megaterium, respectively. They were also active against the alga Chlorella fusca and the bacterium Escherichia coli.
机译:分离了七个不寻常的苯并二氢苯酚内酯类ACG(2C8)以及可食的Carbobrotus内生真菌Blennoria sp。的乙二醛酸B(1)。这是首次报道分离出亚油酸内酯2和3(半水杨酸B和E),长期以来人们一直认为存在作为二聚缩醛酸的单体单元。拟议结构4的化合物(β-二磺酸酯)将需要进行修订,因为其报告的数据与已确立的布伦诺利德C结构的数据不符(4)。其他单体,Blennolides DCF(5C7)似乎是通过水芳族环的重排衍生自Blennolides A(2)和B(3)。异二聚体8由单体布列诺尼德A(2)和布列诺尼德E(6)的重排11-脱羟基衍生物组成,扩展了具有麦角黄质类型骨架的麦角色素家族。通过详细的光谱分析阐明了新化合物的结构,并通过对2个单晶的X射线衍射研究进一步证实。通过CD光谱的TDDFT计算,包括固态CD / TDDFT方法,可以确定绝对构型。 。初步研究表明,这些化合物分别对紫胶菌和巨大芽孢杆菌具有较强的抗真菌和抗菌活性。它们还对海藻小球藻和细菌大肠杆菌具有活性。

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