Brevianthrones, bianthrones from a Chinese isolate of the endophytic fungus Colletotrichum brevisporum Author Lin, Min * & School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin, 300092, People’s Republic of China Author Adpressa, Donovon A. Author Feng, Meiyu Author Lu, Ya Author Clark, Benjamin R. text Phytochemistry 2021 112792 2021-08-31 188 1 8 http://dx.doi.org/10.1016/j.phytochem.2021.112792 journal article 10.1016/j.phytochem.2021.112792 1873-3700 8259135

Table 2 1 H and 13 C NMR Data for brevianthrones B1–B4 (4–7) a.

position	brevianthrone B1 (4)		brevianthrone B2/3		brevianthrone B4
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a Spectra were recorded at 400 MHz for 1 H NMR and 100 MHz for 13 C NMR in CDCl 3.
			(5/6)		(7)
	δ C,	δ H, (J in	δ C, type	δ H, (J in	δ C,	δ H, (J in
	type	Hz)		Hz)	type	Hz)
1	162.3,		162.4/		164.1,
	C		162.7, C		C
1-OCH 3	56.2,	3.84, s	56.4/	3.85/	55.7,	3.98, s
	CH 3		56.4,	3.88, s	CH 3
			CH3
2	98.3,	6.40,	98.7/	6.37/	97.8,	6.50,
	CH	d (1.6)	98.8,	6.41,	CH	d (2.2)
			CH	d (2.1)
3	164.1,		163.4/		161.8,
	C		163.5, C		C
3-OCH 3	55.6,	3.79, s	55.3/	3.71/	55.8,	3.94, s
	CH 3		55.4,	3.75, s	CH 3
			CH3
4	105.5,	6.15,	105.7/	5.65/	105.0,	6.57,
	CH	d (1.6)	105.8,	5.82,	CH	d (2.2)
			CH	d (2.1)
4a	138.8,		140.2/		137.4,
	C		140.8, C		C
5	120.1,	5.95, s	119.6/	6.34/	120.6,	5.67, s
	CH		119.7,	6.59, s	CH
			CH
6	145.4,		146.0/		145.5,
	C		146.3, C		C
7	117.3,	6.60, s	117.1/	6.74/	117.4,	6.66, s
	CH		117.1,	6.76, s	CH
			CH
8	161.5,		161.5/		161.0,
	C		161.6, C		C
8-OH		12.25, s		12.66/		11.96, s
				12.66, s
8a	117.2,		117.2/		117.2,
	C		117.2, C		C
9	187.3,		186.7/		187.1,
	C		187.0, C		C
9a	115.9,		114.3/		116.4,
	C		114.7, C		C
10	57.6,	4.33,	57.2/	4.38/	57.6,	4.41, s
	CH	d (2.6)	57.3,	4.38,	CH
			CH	d (3.8)
10a	140.2,		144.3/		144.7,
	C		144.5, C		C
11	45.8,	2.57, m	45.5/	2.73/	45.8,	2.44, dd
	CH 2	2.54, m	45.8,	2.79, m	CH 2	(9.3,
			CH 2			13.4)
						2.58, dd
						(3.9,
						13.4)
12	67.2,	3.94, m	68.3/	4.10, m	67.3,	3.76, m
	CH		68.6,		CH
			CH
12-OH		3.57		3.49		3.49
13	23.2,	1.16,	23.4/	1.27, ov	23.7,	1.29,
	CH 3	d (6.1)	23.5,		CH 3	d (6.1)
			CH 3
1 ′	164.5,		164.4/		164.5,
	C		164.5, C		C
1 ′ -OH		11.99, s		12.07/		11.95, s
				12.14
2 ′	100.1,	6.33,	99.9/	6.41/	99.8,	6.45,
	CH	d (1.6)	100.1,	6.37,	CH	d (2.2)
			CH	d (2.1)
3 ′	165.5,		165.4/		165.6,
	C		165.6, C		C
3 ′ -	55.7,	3.79, s	55.7/	3.84/	55.9,	3.93, s
OCH 3	CH 3		55.7,	3.89, s	CH 3
			CH3
4 ′	107.9,	6.11,	107.7/	6.14/	107.7,	6.54
	CH	d (2.2)	108.1,	6.34,	CH	d (2.2)
			CH	d (2.1)
4a ′	144.0,		139.6/		138.3,
	C		139.9, C		C
			(5/6)		(7)
	δ C,	δ H, (J in	δ C, type	δ H, (J in	δ C,	δ H, (J in
	type	Hz)		Hz)	type	Hz)
5′	121.5,	6.08, s	121.0/	5.84/	121.3,	5.74, s
	CH		121.1,	6.06, s	CH
			CH
6′	148.1,		147.3/		147.6,
	C		147.5, C		C
7′	117.4,	6.63, s	117.5/	6.69/	119.2,	6.71, s
	CH		117.9,	6.69, s	CH
			CH
8′	162.1,		161.8, C		161.8,
	C				C
8′-OH		11.70, s		11.73/		11.62, s
				11.73, s
8a ′	114.9,		115.1/		114.5,
	C		115.5, C		C
9′	190.3,		190.3/		190.2,
	C		190.4, C		C
9a ′	111.1,		111.1/		111.6,
	C		111.2, C		C
10′	56.0,	4.35,	56.1/	4.37/	56.0,	4.41, s
	CH	d (2.6)	56.2,	4.37,	CH
			CH	d (3.2)
10a ′	145.4,		143.7/		146.3,
	C		144.0, C		C
11′	46.5,	2.41,dd	45.9/	2.48/	46.6,	2.44, dd
	CH2	(8.4, 13.5)	45.9,	2.63, m	CH2	(9.3,
		2.59, dd	CH2			13.4)
		(3.5,13.5)				2.52, dd
						(3.1,
						13.4)
12′	68.4,	4.01, m	67.9/	4.01/	68.3,	3.88, m
	CH		68.0,	4.01, m	CH
			CH
12′-OH		3.42, br s		3.49, br		3.32, br
				s		s
13′	23.9,	1.21,	23.3/	1.27, ovl	23.1,	1.24,
	CH3	d (6.09)	23.4,		CH3	d (5.9)
			CH3