Periconiastone A, an Antibacterial Ergosterol with a Pentacyclo[8.7.0.01,5.02,14.010,15]heptadecane System from Periconia sp. TJ403-rc01

被引:53
作者
Gao, Weixi [1 ,3 ]
Chai, Chenwei [1 ]
He, Yan [4 ]
Li, Fengli [1 ]
Hao, Xincai [2 ]
Cao, Fei [5 ]
Gu, Lianghu [1 ]
Liu, Junjun [1 ]
Hu, Zhengxi [1 ]
Zhang, Yonghui [1 ]
机构
[1] Huazhong Univ Sci & Technol, Hubei Key Lab Nat Med Chem & Resource Evaluat, Sch Pharm, Tongji Med Coll, Wuhan 430030, Hubei, Peoples R China
[2] Hubei Univ Med, Coll Pharm, Shiyan 442000, Peoples R China
[3] Wuhan Univ, Renmin Hosp, Dept Pharm, Wuhan 430060, Hubei, Peoples R China
[4] Huazhong Univ Sci & Technol, Tongji Med Coll, Tongji Hosp, Wuhan 430030, Hubei, Peoples R China
[5] Hebei Univ, Coll Pharmaceut Sci, Baoding 071002, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1021/acs.orglett.9b03270
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Periconiastone A (1), an ergosterol with an unprecedented pentacyclo [8.7.0.0(1,5)0(2,14).0(10,15)]heptadecane system, was isolated from Periconia sp. TJ403-rc01. Its structure was assigned by extensive spectroscopic analyses and quantum-chemical C-13 NMR and ECD calculations. A vinylogous alpha-ketol rearrangement and an aldol condensation reaction during biosynthesis were proposed as key steps for the formation of 1. Compound 1 showed antibacterial activity against Gram-positive S. aureus and E. faecalis with MIC values of 4 and 32 mu g/mL, respectively.
引用
收藏
页码:8469 / 8472
页数:4
相关论文
共 35 条
[1]   Rearranged ergostane-type natural products: chemistry, biology, and medicinal aspects [J].
Duecker, Fenja L. ;
Reuss, Franziska ;
Heretsch, Philipp .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (07) :1624-1633
[2]   Biosynthetic Hypothesis-Guided Discovery and Total Syntheses of PKS-NRPS Hybrid Metabolites from Endophytic Fungus Periconia Species [J].
Fan, Yijun ;
Zhangp, Dewu ;
Tao, Xiaoyu ;
Wang, Yuanhao ;
Liu, Jimei ;
Li, Li ;
Zhao, Jianyuan ;
Yu, Liyan ;
He, Yu-peng ;
Dai, Jungui ;
Tang, Yefeng .
ORGANIC LETTERS, 2019, 21 (06) :1794-1798
[3]  
FUJIMOTO Y, 1984, CHEM PHARM BULL, V32, P4372
[4]   A Highly Conjugated Dihydroxylated C28 Steroid from a Myxobacterium [J].
Gawas, Dnyaneshwar ;
Garcia, Ronald ;
Huch, Volker ;
Mueller, Rolf .
JOURNAL OF NATURAL PRODUCTS, 2011, 74 (05) :1281-1283
[5]  
Gloer J. B., 2007, P257
[6]   Fusicoccane-Derived Diterpenoids from Alternaria brassicicola: Investigation of the Structure-Stability Relationship and Discovery of an IKKβ Inhibitor [J].
Hu, Zhengxi ;
Sun, Weiguang ;
Li, Fengli ;
Guan, Jiankun ;
Lu, Yuanyuan ;
Liu, Junjun ;
Tang, Ying ;
Du, Guang ;
Xue, Yongbo ;
Luo, Zengwei ;
Wang, Jianping ;
Zhu, Hucheng ;
Zhang, Yonghui .
ORGANIC LETTERS, 2018, 20 (17) :5198-5202
[7]   Spiroaspertrione A, a Bridged Spirocyclic Meroterpenoid, as a Potent Potentiator of Oxacillin against Methicillin-Resistant Staphylococcus aureus from Aspergillus sp TJ23 [J].
Hu, Zhengxi ;
Sun, Weiguang ;
Li, Qin ;
Li, Xiao-Nian ;
Zhu, Hucheng ;
Huang, Jinfeng ;
Liu, Junjun ;
Wang, Jianping ;
Xue, Yongbo ;
Zhang, Yonghui .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06) :3125-3131
[8]   Aplysiasecosterol A: A 9,11-Secosteroid with an Unprecedented Tricyclic γ-Diketone Structure from the Sea Hare Aplysia kurodai [J].
Kawamura, Atsushi ;
Kita, Masaki ;
Kigoshi, Hideo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :7073-7076
[9]   Periconicins, two new fusicoccane diterpenes produced by an endophytic fungus Periconia sp with antibacterial activity [J].
Kim, S ;
Shin, DS ;
Lee, T ;
Oh, KB .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (03) :448-450
[10]   Infections associated with steroid use [J].
Klein, NC ;
Go, CHU ;
Cunha, BA .
INFECTIOUS DISEASE CLINICS OF NORTH AMERICA, 2001, 15 (02) :423-+