Abstract：
The genus Penicillium has provided us with the household antibiotic penicillin and the well-known lipid-lowering agent mevastatin. The strain Penicillium sp. SZ-1 was found to grow vigorously in an intact Pinus koraiensis seed, it is inferred that the strain may develop unique mechanisms associated with the biosynthesis of rare metabolites. Further fermentation of the strain on solid rice medium yielded thirteen undescribed compounds, including three andrastin-type meroterpenoids (1-3), two α-pyrone polyketides (4 and 5), and eight sesquicarane derivatives (6-13), along with seven known compounds (14-20). Their structures were determined by detailed analysis of the spectroscopic and spectrometric data (NMR and HRESIMS), in addition to comparisons of the experimental and calculated ECD data for absolute configurational assignments. The hemiacetal moiety in compounds 1 and 2 and the 3α-hydroxy group in compound 3 were rarely found in the andrastin-type meroterpenoid family. The sesquicaranes belong to a small group of sesquiterpenoid that are rarely reported. Bioassay study showed that compound 1 exhibited inhibitory effects against Staphylococcus aureus ATCC 29213 and Escherichia coli ATCC 25922 with MIC values of 64 and 32 μg/mL, respectively. In addition, compounds 1 and 3 displayed weak DPPH radical scavenging activities. The andrastins and sesquicaranes in this study enriched the structural diversity of these classes of terpenoids. Of note, this study is the first report on the metabolites of a fungus isolated from P. koraiensis seed.
摘要：
青霉属为我们提供了家用抗生素青霉素和众所周知的降脂药美伐他汀。菌株青霉属。发现SZ-1在完整的红松种子中生长旺盛，据推测，该菌株可能发展出与稀有代谢物生物合成相关的独特机制。该菌株在固体水稻培养基上进一步发酵，产生了13种未描述的化合物，包括三种安拉斯汀型黄硫萜类化合物（1-3），两个α-吡喃酮聚酮化合物(4和5)，和八种倍半碳烷衍生物（6-13），连同七个已知化合物(14-20)。通过对光谱和光谱数据（NMR和HRESIMS）的详细分析来确定它们的结构，除了对绝对构型分配的实验和计算的ECD数据进行比较之外。化合物1和2中的半缩醛部分以及化合物3中的3α-羟基在andrastin型黄硫萜类家族中很少发现。倍半烷属于很少报道的一小群倍半萜。生物测定研究表明，化合物1对金黄色葡萄球菌ATCC29213和大肠杆菌ATCC25922具有抑制作用，MIC值为64和32μg/mL，分别。此外,化合物1和3表现出弱的DPPH自由基清除活性。本研究中的安拉斯汀和倍半烷丰富了这些萜类化合物的结构多样性。值得注意的是，这项研究是关于从红松种子中分离出的真菌代谢产物的首次报道。
