. 2021 Dec 27;20(1):31. doi: 10.3390/md20010031

Table 1.

¹H (500 MHz), ¹³C (125 MHz), and ¹⁵N 50 MHz) NMR data of compounds 1–4 in DMSO-d₆:H₂O (4:1) at 50 °C.

Unit/ Position	Theonellamide J (1)		5-cis-Apoa-Theo-palauamide (2)		Theonellamide K (3)		Theopalauamide (4)
Unit/ Position	δ_C/N	δ_H	δ_C/N	δ_H	δ_C/N	δ_H	δ_C/N	δ_H
Apcoa/Apoa-1	171.8, C		172.6, C		172.2, C		172.6, C
2a	40.4, CH₂	2.33, t	37.6, CH₂	2.36, t	37.4, CH₂	2.37, t	37.6, CH₂	2.37, m
2b		1.93, dd		2.15, dd		2.13, dd		2.10, brd
3	48.3, CH	4.22, m	53.2, CH	4.10, m	52.8, CH	4.11, m	53.0, CH	4.11, m
3-NH	122.3, NH	7.82, d	118.0, NH	7.69, d	118.4, NH	7.70, d	117.76, NH	7.72, d
4	62.1, CH	1.71, ddd	67.7, CH	4.51, m	68.5, CH	4.25, m	68.7, CH	4.25, m
5	78.9, CH	3.98, m	130.9, CH	5.05, brd	132.9, CH	5.18, d	132.7, CH	5.14, d
6	142.3, C		135.3, C		135.9, C		136.3, C
6-Me	14.1, CH₃	1.61, brs	21.1, CH₃	1.82, brs	13.4 CH₃	1.65, s	13.5, CH₃	1.64, s
7	129.1, CH	5.02, brs	126.5, CH	7.09, d	133.8, CH	6.62, d	134.0, CH	6.58, d
8	50.6, CH	2.76, m	130.8, CH	6.60, d	128.2, CH	6.50, d	128.6, CH	6.49, d
9	145.6, C		138.1, C		137.8, C		138.0, C
10,10’	128.3, CH	7.14, d	127.6, CH	7.43, d	126.9, CH	7.41, d	127.1, CH	7.38, d
11,11’	129.0 CH	7.20, t	129.7, CH	7.27, dd	129.5, CH	7.31, t	129.7, CH	7.29, t
12	127.0, CH	7.13, m	129.2, CH	7.17, t	128.3, CH	7.19, t	128.9, CH	7.17, m
Ser1-1	172.3, C		172.8, C		172.3, C		172.8, C
2	56.6, CH	3.71, m	56.8, CH	3.74, m	56.6, CH	3.78, m	56.8, CH	3.76, m
2-NH	119.2, NH	7.69, brs	114.7, NH	7.77, m	119.4, NH	7.77, s	114.9, NH	7.80, brs
3	61.9, CH₂	3.62, m	61.2, CH₂	3.62, m	61.0, CH₂	3.64, m	61.1, CH₂	3.64, m
sAla-1	169.6, C		169.8, C		169.6, C		169.9, C
2	51.1, CH	5.04, m	51.4, CH	5.06, m	51.1, CH	5.06, m	51.4, CH	5.07, m
2-NH	107.7, NH	8.23, d	108.5, NH	8.26, d	108.1, NH	8.27, d	108.3, NH	8.28, d
3a	50.5, CH₂	4.88, d	50.6, CH₂	4.89, brd	50.5, CH₂	4.89, d	50.6, CH₂	4.90, brd
3b		4.22, m		4.20, m		4.22, dd		4.21, m
Asn-1	171.5, C		171.4, C		171.2, C		171.6, C
2	51.9, CH	4.48, brm	52.2, CH	4.49, m	51.9, CH	4.52, m	52.2, CH	4.50, m
2-NH	114.6, NH	7.73, d	119.2, NH	7.78, s	114.7, NH	7.78, brs	119.2, NH	7.77, d
3a	37.1, CH₂	2.45, m	37.4, CH₂	2.55, dd	37.1, CH₂	2.56, dd	37.2, CH₂	2.58, dd
3b		2.24, m		2.30, dd		2.32, dd		2.35, dd
4	172.2, C		172.5, C		172.1, C		172.5, C
4-NH₂	102.7, NH₂	7.31, brs	103.9, NH₂	7.31, brs	103.5, NH₂	7.32, brs	103.8, NH₂	7.37, brs
		6.62, s		6.73, brs		6.76, brs		6.76, brs
Han-1	171.5, C		171.3, C		170.9, C		171.4, C
2	54.4, CH	5.39, m	54.7, CH	5.37, t	54.5, CH	5.36, dd	54.7, CH	5.39, t
2-NH	108.7, NH	8.33, d	108.8, NH	8.30, d	108.9, NH	8.32, d	108.7, NH	8.35, d
3	71.9, CH	3.95, m	72.4, CH	3.96, m	72.2, CH	3.97, brd	72.4, CH	3.98 m
3-OH		4.87, m		5.18, d		5.12, brs		5.19, brd
4	174.2, C		174.5, C		174.1, C		174.5, C
4-NH₂	102.2, NH₂	7.14, brs	102.0, NH₂	7.04, m	102.3, NH₂	7.25, s	102.1, NH₂	7.28, m
		7.19, brs		7.25, m		7.07, s		7.05, m
BrMePhe/MePhe-1	171.1, C		172.0, C		171.7, C		172.0, C
2	59.1, CH	4.58, m	59.2, CH	4.52, m	59.3, CH	4.51, dd	59.3, CH	4.54, m
2-NH	111.5, NH	7.86, d	113.1, NH	8.17, d	114.0, NH	8.23, d	113.1, NH	8.19, d
3	38.9, CH	3.49, m	39.6, CH	3.35, m	40.1, CH	3.31, dq	39.5, CH	3.35, qd
3-Me	17.9, CH₃	1.10, d	18.0, CH₃	1.04, d	18.1, CH₃	1.08, d	18.0, CH₃	1.05, d
4	141.2, C		141.8, C		142.4, C		141.8, C
5,5’	131.1, CH	6.99, d	131.1, CH	6.98, d	128.6, CH	7.07, d	131.1, CH	6.99, d
6,6’	131.5, CH	7.28, d	131.7, CH	7.25, d	128.7, CH	7.12, m	131.7, CH	7.26 d
7	120.5, C		120.6, C		127.1, CH	7.11, t	120.6, C
iSer-1	172.2, C		171.6, C		171.2, C		171.4, C
2	69.7, CH	4.13, m	69.9, CH	4.08, m	69.7, CH	4.05, brs	69.8, CH	4.09, m
2-OH		5.42, brs		5.03 m				5.03, m
3a	43.9, CH₂	3.81, m	44.1, CH₂	3.73, m	44.0, CH₂	3.69, m	44.0, CH₂	3.74, m
3b		2.98, brd		3.00, brd		3.00, dd		3.01, brd
3-NH	100.3, NH	7.24, m	101.0, NH	7.20, m	100.2, NH	7.19, m	101.2, NH	7.22, m
Ada-1	173.9, C		175.9, C		175.4, C		176.0, C
2	52.2, CH	4.08, m	54.7, CH	3.88, m	54.6, CH	3.87, m	54.7, CH	3.91, m
2-NH	110.6, NH	7.49, d	116.7, NH	7.58, d	116.5, NH	7.58, d	116.5, NH	7.59, d
3a	31.2, CH₂	1.66, m	32.4, CH₂	1.65, m	32.4, CH₂	1.66, m	32.4, CH₂	1.65, m
3b		1.51, m		1.43, m		1.43, m		1.44, m
4a	21.7, CH₂	1.22, m	22.2, CH₂	1.11, m	22.2, CH₂	1.19, m	22.2, CH₂	1.12, m
4b		0.88, m
5a	35.0, CH₂	2.08, m	35.9, CH₂	2.05, dt	35.8, CH₂	2.05, dt	35.9, CH₂	2.06, m
5b		1.80, m		1.70, m		1.72, m		1.70, m
6	173.4, C		174.3, C		174.1, C		174.3, C
sHis-1	170.6, C		171.0, C		170.7, C		171.0, C
2	54.4, CH	4.73, m	54.5, CH	4.74, ddd	54.3, CH	4.77, m	54.6, CH	4.75, dt
2-NH	119.6, NH	8.36, d	119.6, NH	8.32, d	119.9, NH	8.37, d	119.7, NH	8.33, m
3a	26.4, CH₂	3.28, brt	26.4, CH₂	3.26, t	26.2, CH₂	3.28, t	26.4, CH₂	3.27, t
3b		2.94, brd		2.96, m		2.96, dd		2.98, m
4	131.9, C		132.0, C		131.8, C		132.0, C
5-N	181.0, N		181.2, N		181.4, N		180.9, N
6	137.3, CH	8.89, s	137.4, CH	8.85, s	137.2, CH	8.87, s	137.4, CH	8.86, s
7-N	167.4, N		167.4, N		167.8, N		167.9, N
8	124.0, CH	7.19, s	124.3, CH	7.21, brs	124.1, CH	7.25, s	124.3, CH	7.22, brs
Thr-1	172.5, C		172.7, C		172.5, C		172.7, C
2	58.7, CH	4.29, m	58.9, CH	4.23, m	58.7, CH	4.22, m	58.9, CH	4.23, m
2-NH	113.5, NH	7.60, d	114.1, NH	7.67, d	114.1, NH	7.71, d	114.3, NH	7.69, d
3	68.8, CH	3.63, m	68.9, CH	3.59, m	68.7, CH	3.61, m	69.0, CH	3.60, m
3-OH		5.40, brs		5.35, d		5.20, d		4.90, m
4	21.6, CH₃	1.04, d	21.5, CH₃	0.97, d	21.5, CH₃	0.97, d	21.6, CH₃	0.98, d
Ser2-1	169.8, C		169.9, C		169.7, C		169.9, C
2	56.5, CH	4.46, m	56.8, CH	4.41, m	56.4, CH	4.44, dt	56.6, CH	4.45, m
2-NH	116.7, NH	8.52, d	116.6, NH	8.47, d	116.7, NH	8.48, d	117.0, NH	8.48, d
3	62.0, CH₂	3.68, m	62.1, CH₂	3.57, m	61.9, CH₂	3.64, m	62.1, CH₂	3.64, m
				3.64, m
Phe-1	171.5, C		171.8, C		171.4, C		171.6, C
2	55.2, CH	4.56, m	55.1, CH	4.47, m	54.9, CH	4.55, ddd	55.0, CH	4.56, m
2-NH	115.8, NH	7.97, d	115.3, NH	7.91, d	115.7, NH	7.94, d	115.9, NH	7.96, d
3a	39.2, CH₂	2.77, m	39.2, CH₂	2.70, dd	39.2, CH₂	2.81, dd	39.4, CH₂	2.81, dd
3b		2.72, m		2.61, dd		2.65, dd		2.65, dd
4	136.9, C		137.3, C		137.3, C		137.3, C
5,5’	129.6, CH	7.10, m	129.9, CH	7.01, d	129.8, CH	7.14, m	130.0, CH	7.13, d
6,6’	128.9, CH	7.14, m	129.1, CH	7.16, t	129.0, CH	7.22, d	129.2, CH	7.21, m
7	127.3, CH	7.13, m	127.5, CH	7.10, t	127.3, CH	7.18, m	127.7, CH	7.14, m
Gal-1	88.9, CH	5.03, d	89.0, CH	5.02, d	88.9, CH	5.02, d	89.0, CH	5.03, d
2	69.5, CH	3.61, m	69.8, CH	3.62, m	69.7, CH	3.63, m	69.9, CH	3.63, m
3	73.7, CH	3.41, brd	73.8, CH	3.41, m	73.7, CH	3.40, brd	73.9, CH	3.43, brd
4	69.7, CH	3.83, m	69.6, CH	3.81, m	69.5, CH	3.81, m	69.6, CH	3.83, m
5	78.9, CH	3.66, m	79.0, CH	3.64, m	78.8, CH	3.64, m	79.0, CH	3.64, m
6a	61.9, CH₂	3.65, m	62.1, CH₂	3.75, m	61.9, CH₂	3.75, m	62.0, CH₂	3.75, m
6b		3.58, m		3.54, m		3.64, m		3.64, m