Bioactive secondary metabolites of rhizosphere fungi <i>Penicillium</i> sp. XYR-9 of <i>Cynanchum bungei</i> Decne

Abstract

Abstract:

ObjectiveTo study a new natural product with good antibacterial activity from the rhizosphere fungiPenicilliumsp. XYR-9 ofCynanchum bungei Decneand provide a theoretical guidance and a material basis for the discovery of novel antibacterial lead compounds with high efficiency and low toxicity.MethodsOn the basis of optimizing the fermentation conditions， rice culture medium was used as the optimal fermentation scheme to enrich the secondary metabolites， further isolated and purified by activity-oriented and the monomer compounds were confirmed by nuclear magnetic resonance and mass spectrometry methods.ResultsFive indole diterpenoids were isolated， identified， and tested for antibacterial activity. The antimicrobial activity of compounds 1， 3 and 5 was tested， and the results showed that the MIC values of compounds 1， 3 and 5 against the standard strains ofS.aureusATCC33591 were 95.70， 106.40 and 118.65 mg·L^-1respectively， and 54.12， 43.54 and 42.74 mg·L^-1against the standard strains ofE.coliATCC25922.ConclusionThe five indole terpenes obtained fromPenicilliumsp. XYR-9 secondary metabolite， antimicrobial activity tests indicate that these compounds have weak antibacterial activity against bacteria.

Key words:Cynanchum bungeiDecne.,rhizosphere soil,Fungi,bacteriostatic activity,indole diterpene

摘要：

目的以泰山白首乌根际真菌Penicilliumsp. XYR‐9为研究对象，寻找具有良好抑菌活性的新型天然产物，为高效、低毒新型抗菌先导化合物的发现提供理论指导和物质基础。方法在优化其发酵条件基础上，确定大米培养基为最优发酵方案，对其次级代谢产物进行富集，以活性为导向，进一步分离、纯化获得单体化合物，通过核磁共振（nuclear magnetic resonance，NMR）和质谱（mass spectrometry，MS）等方法分析化合物的结构。结果分离鉴定得到5个吲哚二萜类化合物并进行了抑菌活性检测，化合物1、3和5对金黄色葡萄球菌标准菌株的最小抑菌浓度（minimum inhibitory concentration，MIC）分别为95.70、106.40和118.65 mg·L^-1，对大肠杆菌标准菌株的MIC值分别为54.12、43.54和42.74 mg·L^-1。结论通过分离Penicilliumsp. XYR‐9次级代谢产物获得的5个吲哚萜类化合物，抗菌活性测试提示该类化合物对细菌具有弱的抗菌作用。

关键词:泰山白首乌,根际土壤,真菌,抑菌活性,吲哚二萜

Fujin LV, Daqing KONG, Jingzhi QU, Xijin LIU, Xiaoyu LI, Guojun PAN. Bioactive secondary metabolites of rhizosphere fungiPenicilliumsp. XYR-9 ofCynanchum bungeiDecne[J]. Journal of Shandong First Medical Unversity & Shandong Academy of Medical Sciences, 2023, 44(9): 647-651.

吕甫晋, 孔大庆, 屈敬之, 刘熙瑾, 李晓玉, 潘国军. 泰山白首乌根际真菌Penicilliumsp. XYR-9活性次级代谢产物研究[J]. betway必威登陆网址（betway.com ）学报, 2023, 44(9): 647-651.

Figures/Tables7

样品编号	指示菌株
XYR-9	+++	+++
XYR-8	++	++
ZXR-3	++	++
ZXR-4	++	+++
环丙沙星	++++	++++

样品编号	指示菌株
XYR-9	+++	+++
XYR-8	++	++
ZXR-3	++	++
ZXR-4	++	+++
环丙沙星	++++	++++

位置	化合物1	化合物2	化合物3	化合物4	化合物5
1	150.86，C	151.90，C	166.71，C	170.62，C	197.75，C
2	139.98，C	139.18，C	149.69，C	160.00，C	169.87，C
3	130.25，C	129.75，C	139.17，C	156.25，C	129.55，C
4	127.92，CH	129.39，CH	131.77，CH	151.42，CH	129.29，CH
5	125.00，CH	129.32，CH	130.45，CH	139.32，CH	125.19，CH
6	120.42，CH	129.00，CH	124.93，CH	132.06，CH	120.90，CH
7	119.54，CH	125.09，CH	124.76，CH	116.83，CH	119.60，CH
8	118.39，CH	125.02，CH	121.31，CH	115.50，CH	118.48，CH
9	111.45，CH	121.58，CH	120.44，CH	112.63，CH	117.76，CH
10	85.72，CH	87.75，CH	95.57，CH	87.82，CH	82.50，CH
11	84.68，CH	78.04，CH	76.78，CH	78.12，CH	75.98，CH
12	71.99，C	76.46，C	72.02，C	76.52，C	75.01，C
13	53.01，CH	51.07，CH	50.22，CH	51.55，CH	50.32，CH
14	48.76，CH	39.45，CH	48.43，CH	39.59，CH	42.47，CH
15	46.41，C	32.46，C	42.43，C	35.63，C	42.12，C
16	40.01，CH₂	30.91，CH₂	41.87，CH₂	34.05，CH₂	31.47，CH₂
17	37.65，CH₂	29.19，CH₂	35.68，CH₂	32.54，CH₂	29.88，CH₂
18	36.55，CH₂	28.68，CH₂	34.09，CH₂	29.46，CH₂	26.75，CH₂
19	33.89，CH₂	28.02，CH₂	30.45，CH₂	29.40，CH₂	25.45，CH₂
20	27.52，CH	27.83，CH	26.70，CH	28.68，CH	24.93，CH
21	26.08，C	26.25，C	25.33，C	28.59，C	23.94，C
22	25.28，CH₃	24.55，CH₃	25.16，CH₃	27.91，CH₃	23.88，CH₃
23	24.62，CH₂	24.46，CH₂	24.57，CH₂	27.17，CH₂	20.91，CH₂
24	23.68，CH₂	22.43，CH₂	23.93，CH₂	26.36，CH₂	16.91，CH₂
25	21.97，CH₃	20.91，CH₃	23.84，CH₃	22.49，CH₃	16.58，CH₃
26	21.94，CH₃	16.91，CH₃		22.09，CH₃	15.19，CH₃
27	1.99，CH₃	16.58，CH₃	14.26，CH₃	21.07，CH₃	14.90，CH₃
28		15.19，CH₂
29		170.99，CH
30		188.04，C
31		14.60，CH₃
32				72.01，CH₂
33				15.30，CH₃
34				77.04，C

位置	化合物1	化合物2	化合物3	化合物4	化合物5
1	150.86，C	151.90，C	166.71，C	170.62，C	197.75，C
2	139.98，C	139.18，C	149.69，C	160.00，C	169.87，C
3	130.25，C	129.75，C	139.17，C	156.25，C	129.55，C
4	127.92，CH	129.39，CH	131.77，CH	151.42，CH	129.29，CH
5	125.00，CH	129.32，CH	130.45，CH	139.32，CH	125.19，CH
6	120.42，CH	129.00，CH	124.93，CH	132.06，CH	120.90，CH
7	119.54，CH	125.09，CH	124.76，CH	116.83，CH	119.60，CH
8	118.39，CH	125.02，CH	121.31，CH	115.50，CH	118.48，CH
9	111.45，CH	121.58，CH	120.44，CH	112.63，CH	117.76，CH
10	85.72，CH	87.75，CH	95.57，CH	87.82，CH	82.50，CH
11	84.68，CH	78.04，CH	76.78，CH	78.12，CH	75.98，CH
12	71.99，C	76.46，C	72.02，C	76.52，C	75.01，C
13	53.01，CH	51.07，CH	50.22，CH	51.55，CH	50.32，CH
14	48.76，CH	39.45，CH	48.43，CH	39.59，CH	42.47，CH
15	46.41，C	32.46，C	42.43，C	35.63，C	42.12，C
16	40.01，CH₂	30.91，CH₂	41.87，CH₂	34.05，CH₂	31.47，CH₂
17	37.65，CH₂	29.19，CH₂	35.68，CH₂	32.54，CH₂	29.88，CH₂
18	36.55，CH₂	28.68，CH₂	34.09，CH₂	29.46，CH₂	26.75，CH₂
19	33.89，CH₂	28.02，CH₂	30.45，CH₂	29.40，CH₂	25.45，CH₂
20	27.52，CH	27.83，CH	26.70，CH	28.68，CH	24.93，CH
21	26.08，C	26.25，C	25.33，C	28.59，C	23.94，C
22	25.28，CH₃	24.55，CH₃	25.16，CH₃	27.91，CH₃	23.88，CH₃
23	24.62，CH₂	24.46，CH₂	24.57，CH₂	27.17，CH₂	20.91，CH₂
24	23.68，CH₂	22.43，CH₂	23.93，CH₂	26.36，CH₂	16.91，CH₂
25	21.97，CH₃	20.91，CH₃	23.84，CH₃	22.49，CH₃	16.58，CH₃
26	21.94，CH₃	16.91，CH₃		22.09，CH₃	15.19，CH₃
27	1.99，CH₃	16.58，CH₃	14.26，CH₃	21.07，CH₃	14.90，CH₃
28		15.19，CH₂
29		170.99，CH
30		188.04，C
31		14.60，CH₃
32				72.01，CH₂
33				15.30，CH₃
34				77.04，C

化合物编号	指示菌株MIC值/（mg·L^-1）
化合物1	95.70	54.12
化合物2
化合物3	106.40	43.54
化合物4
化合物5	118.65	42.74
环丙沙星	16.83	4.21

化合物编号	指示菌株MIC值/（mg·L^-1）
化合物1	95.70	54.12
化合物2
化合物3	106.40	43.54
化合物4
化合物5	118.65	42.74
环丙沙星	16.83	4.21

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Bioactive secondary metabolites of rhizosphere fungiPenicilliumsp. XYR-9 ofCynanchum bungeiDecne

泰山白首乌根际真菌Penicilliumsp. XYR-9活性次级代谢产物研究

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样品编号	指示菌株
样品编号	E.coliATCC25922	S.aureusATCC33591
XYR-9	+++	+++
XYR-8	++	++
ZXR-3	++	++
ZXR-4	++	+++
环丙沙星	++++	++++