Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22

被引：45

作者：

Lai, Daowan ^{[1
]}

Wang, Ali ^{[1
]}

Cao, Yuheng ^{[1
]}

Zhou, Kaiyi ^{[1
]}

Mao, Ziling ^{[1
]}

Dong, Xuejiao ^{[1
]}

Tian, Jin ^{[1
,2
]}

Xu, Dan ^{[1
]}

Dai, Jungui ^{[3
,4
]}

Peng, Yu ^{[5
]}

Zhou, Ligang ^{[1
]}

Liu, Yang ^{[6
]}

机构：

[1] China Agr Univ, Coll Plant Protect, Dept Plant Pathol, Key Lab Plant Pathol,Minist Agr, Beijing 100193, Peoples R China

[2] Chinese Acad Sci, Inst Genet & Dev Biol, Natl Ctr Plant Gene Res Beijing, Beijing 100101, Peoples R China

[3] Chinese Acad Med Sci, Inst Mat Med, State Key Lab Bioact Subst & Funct Nat Med, Beijing 100050, Peoples R China

[4] Peking Union Med Coll, Beijing 100050, Peoples R China

[5] Hunan Tobacco Ind Co Ltd, Ctr Tech, Changsha 410014, Hunan, Peoples R China

[6] Chinese Acad Agr Sci, Inst Food Sci & Technol, Minist Agr, Key Lab Agroprod Proc, Beijing 100193, Peoples R China

来源：

JOURNAL OF NATURAL PRODUCTS | 2016年 / 79卷 / 08期

关键词：

PHOMA SP TC-1674; TMC-264; ORIGIN; ALTERNARIOL; METABOLITES;

D O I：

10.1021/acs.jnatprod.6b00327

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Six new dibenzo-alpha-pyrones, rhizopycnolides A (1) and B (2) and rhizopycnins A-D (3-6), together with eight known congeners (7-14), were isolated from the endophytic fungus Rhizopycnis vagum Nitaf22 obtained from Nicotiana tabacum. The structures of the new compounds were unambiguously elucidated using NMR, HRESIMS, TDDFT ECD calculation, and X-ray crystallography data. Rhizopycnolides A (1) and B (2) feature an uncommon gamma-butyrolactone-fused dibenzo-alpha-pyrone tetracyclic skeleton (6/6/6/5), while rhizopycnin B (4) was the first amino group containing dibenzo-alpha-pyrone. Rhizopycnolides A (1) and B (2) are proposed to be biosynthesized from polyketide and tricarboxylic acid cycle pathways. The isolated compounds were tested for their antibacterial, antifungal, and cytotoxic activities. Among them, rhizopycnolide A (1), rhizopycnins C (5) and D (6), TMC-264 (8), penicilliumolide D (11), and alternariol (12) were active against the tested pathogenic bacteria Agrobacterium tumefaciens, Bacillus subtilis, Pseudomonas lachrymans, Raistonia solanacearum, Staphylococcus hemolyticus, and Xanthomonas vesicatoria with MIC values in the range 25-100 mu g/mL. Rhizopycnin D (6) and TMC-264 (8) strongly inhibited the spore germination of Magnaporthe oryzae with IC50 values of 9.9 and 12.0 mu g/mL, respectively. TMC-264 (8) showed potent cytotoxicity against five human cancer cell lines (HCT-116, HepG2, BGC-823, NCI-H1650, and A2780) with IC50 values of 3.2-7.8 mu M.

引用

页码：2022 / 2031

页数：10