Absolute Configuration Determination of Two Drimane Sesquiterpenoids from the Endophytic Fungi Talaromyces Purpureogenus of Panax notoginseng†

doi:10.7503/cjcu20170006

Abstract

Abstract:

Two drimane sesquiterpenoids(1, 2) were isolated from cultures of the fungus Talaromyces purpureogenus. The planar structures were well established by NMR and mass spectrometry, and the absolute configurations(AC) were determined by comparing experimental electronic circular dichroism(ECD) and optical rotation(OR) of compounds 1 and 2 with the calculated ECD and OR data using quantum methods. Compounds 1 and 2 were evaluated for antibacterial activities against four spices of pathogenic bacteria, and the results showed that compound 1 had weak antibacterial activities against Escherichia coli(MIC=25 μmol/L).

Key words: Talaromyces purpureogenus, Electroic circalar dichroism(ECD), Absolute configuration, Antibacterial activity

CLC Number:

O629.9

TrendMD:

ZHANG Bingyang, MA Yangyang, GUO Hua, ZHU Huajie, LI Wan. Absolute Configuration Determination of Two Drimane Sesquiterpenoids from the Endophytic Fungi Talaromyces Purpureogenus of Panax notoginseng^†[J]. Chem. J. Chinese Universities, 2017, 38(6): 1046.

Figures/Tables 4

References 36

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Atom	Compound 1		Atom	Compound 2
Atom	¹H NMR (400 MHz, DMSO), δ		¹³C NMR (100 MHz, DMSO), δ	¹H NMR (600 MHz,CDCl₃), δ	¹³C NMR (150 MHz, CDCl₃), δ
1	3.67,(s, 1H)	69.3, CH	1	5.00,(brs, 1H)	76.2, CH
2	1.46,(m, 1H), 1.89,(m, 1H)	25.2, CH₂	2	1.94,(t, J=13.8 Hz, 1H) 1.77,(brs, 1H)	23.6, CH₂
3	1.13,(m, 1H) 1.71,(m, 1H)	34.3, CH₂	3	1.61,(dt, J=3.0, 13.8 Hz, 1H) 1.35,(td, J=3.0, 13.8 Hz, 1H)	34.9, CH₂
4		32.1, C	4		32.6, C
5	2.08,(dd, J=4.8, 10.0 Hz, 1H)	37.4, CH	5	2.51,(dd, J=6.0, 10.2 Hz, 1H)	37.9, CH
6	1.67,(m, 2H)	28.3, CH₂	6	2.57,(dt, J=6.0, 20.4 Hz, 1H) 2.24,(m, 1H)	25.6, CH₂
7	4.21,(brs, 1H)	58.4, CH	7	6.99,(t, J=3.0 Hz, 1H)	139.9, CH
8		125.0, C	8		130.5, C
Atom	Compound 1		Atom	Compound 2
Atom	¹H NMR (400 MHz, DMSO), δ		¹³C NMR (100 MHz, DMSO), δ	¹H NMR (600 MHz,CDCl₃), δ	¹³C NMR (150 MHz, CDCl₃), δ
9		173.2, C	9		78.0, C
10		42.1, C	10		41.1, C
11	4.91,(d, J=5.2Hz, 1H) 4.94,(d, J=5.2 Hz, 1H)	68.1, CH₂	11	4.39,(d, J=10.2 Hz, 1H) 4.25,(d, J=10.2 Hz, 1H)	74.1, CH₂
12		174.1, C	12		168.7, C
13	0.88,(s, 3H)	32.7, CH₃	13	1.03,(s, 3H)	33.0, CH₃
14	0.84,(s, 3H)	21.4, CH₃	14	1.02,(s, 3H)	21.7, CH₃
15	1.01,(s, 3H)	19.2, CH₃	15	0.91,(s, 3H)	18.6, CH₃
1'			1'		170.9, C
2'			2'	4.34,(t, J=6.6 Hz, 1H)	59.0, CH
3'			3'	2.20,(m, 1H)	30.0, CH
4'			4'	1.01,(d, J=6.6 Hz, 3H)	19.3, CH₃
5'			5'	0.98,(d, J=6.6 Hz, 3H)	18.0, CH₃
Ac			Ac		170.0, C
Ac CH₃			Ac CH₃	2.05,(s, 3H)	23.1, CH₃
NH			NH	6.12,(brd, J=6.6 Hz, 1H)

Atom	Compound 1		Atom	Compound 2
Atom	¹H NMR (400 MHz, DMSO), δ		¹³C NMR (100 MHz, DMSO), δ	¹H NMR (600 MHz,CDCl₃), δ	¹³C NMR (150 MHz, CDCl₃), δ
1	3.67,(s, 1H)	69.3, CH	1	5.00,(brs, 1H)	76.2, CH
2	1.46,(m, 1H), 1.89,(m, 1H)	25.2, CH₂	2	1.94,(t, J=13.8 Hz, 1H) 1.77,(brs, 1H)	23.6, CH₂
3	1.13,(m, 1H) 1.71,(m, 1H)	34.3, CH₂	3	1.61,(dt, J=3.0, 13.8 Hz, 1H) 1.35,(td, J=3.0, 13.8 Hz, 1H)	34.9, CH₂
4		32.1, C	4		32.6, C
5	2.08,(dd, J=4.8, 10.0 Hz, 1H)	37.4, CH	5	2.51,(dd, J=6.0, 10.2 Hz, 1H)	37.9, CH
6	1.67,(m, 2H)	28.3, CH₂	6	2.57,(dt, J=6.0, 20.4 Hz, 1H) 2.24,(m, 1H)	25.6, CH₂
7	4.21,(brs, 1H)	58.4, CH	7	6.99,(t, J=3.0 Hz, 1H)	139.9, CH
8		125.0, C	8		130.5, C
Atom	Compound 1		Atom	Compound 2
Atom	¹H NMR (400 MHz, DMSO), δ		¹³C NMR (100 MHz, DMSO), δ	¹H NMR (600 MHz,CDCl₃), δ	¹³C NMR (150 MHz, CDCl₃), δ
9		173.2, C	9		78.0, C
10		42.1, C	10		41.1, C
11	4.91,(d, J=5.2Hz, 1H) 4.94,(d, J=5.2 Hz, 1H)	68.1, CH₂	11	4.39,(d, J=10.2 Hz, 1H) 4.25,(d, J=10.2 Hz, 1H)	74.1, CH₂
12		174.1, C	12		168.7, C
13	0.88,(s, 3H)	32.7, CH₃	13	1.03,(s, 3H)	33.0, CH₃
14	0.84,(s, 3H)	21.4, CH₃	14	1.02,(s, 3H)	21.7, CH₃
15	1.01,(s, 3H)	19.2, CH₃	15	0.91,(s, 3H)	18.6, CH₃
1'			1'		170.9, C
2'			2'	4.34,(t, J=6.6 Hz, 1H)	59.0, CH
3'			3'	2.20,(m, 1H)	30.0, CH
4'			4'	1.01,(d, J=6.6 Hz, 3H)	19.3, CH₃
5'			5'	0.98,(d, J=6.6 Hz, 3H)	18.0, CH₃
Ac			Ac		170.0, C
Ac CH₃			Ac CH₃	2.05,(s, 3H)	23.1, CH₃
NH			NH	6.12,(brd, J=6.6 Hz, 1H)