Spirornatas A-C from brown alga Turbinaria ornata: Anti-hypertensive spiroketals attenuate angiotensin-I converting enzyme Author Chakraborty, Kajal *, Shubhajit Dhara & Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P. B. No. 1603, Cochin, India Author Dhara, Shubhajit text Phytochemistry 2022 113024 2022-03-31 195 1 10 http://dx.doi.org/10.1016/j.phytochem.2021.113024 journal article 58680 10.1016/j.phytochem.2021.113024 05f95d8a-c92f-423f-8517-ffa0fa7af90c 1873-3700 8194471

Table 1 NMR spectroscopic data of spirornatas A-C a

Spirornata A					Spirornata B					Spirornata C
CN: Carbon number in the structures. a NMR spectra recorded using Bruker AVANCE III 500 MHz (AV 500) spectrometer (Bruker, Karlsruhe, Germany) in deuteriated chloroform (CDCl) as aprotic 3 solvent at ambient temperature with tetramethyl silane (TMS) as the internal standard (δ 0 ppm). NMR data was administered using MestReNova-7.1.1–9649. 1 H NMR spectra were recorded at 500 MHz, while the 13 C NMR spectra were recorded at 125 MHz.
C.	13C	δ 1H NMR (mult., J	COSY	HMBC	C.	13C	δ 1H NMR (mult.,	COSY	HMBC	C.	13C	δ 1H NMR (mult.,	COSY	HMBC
N.		in Hz, int)b			N.		J in Hz, int)b			N.		J in Hz, int)b
2	62.1	4.02 (Ha) (1H, d, J	H-2a	C-7	2	61.6	4.05 (Ha) (1H, d,	–	C-2a, 8	2	62.4	4.09 (Ha) (1H, d,	–	C-2a, 8
		= 9.65)					J = 8.65)					J = 7.86)
		3.83 (Hb) (1H, d, J					3.37 (Hb) (1H, d,					3.48 (Hb) (1H, d,
		= 8.85)					J = 8.55)					J = 7.68)
2a	42.6	2.82 (1H, t, J =	–	C-3, 5a	2a	127.9	–	–	–	2a	127.9	–	–	–
		7.99)
3	179.2	–	–	–	3	47.2	2.90 (2H, s)	–	C-2a, 4	3	48.1	2.96 (2H, s)		C-2a, 4
5	70.4	4.38 (Ha) (1H, d, J	H-5a	C-3	4	203.5	–	–	–	4	202.4	–	–	–
		= 8.65)
		4.12 (Hb) (1H, d, J
		= 8.56)
5a	35.2	2.32 (1H, t, J =	H-6	C-5	5	39.7	2.48 (2H, dd, J =	H-6	C-4, 6a	5	40.8	2.46 (2H, dd, J =	H-6	C-4, 6a
		7.99)					10.19, 4.86)					10.34, 4.76)
6	37.7	2.18 (1H, m)	H-8	C-5a, 7	6	22.5	2.27 (2H, dd, J =	–	C-4, 6a	6	25.5	2.24 (2H, dd, J =	–	C-4, 6a
							10.09, 4.66)					10.33, 4.96)
7	101.4	–	–	–	6a	125.7	–	–	–	6a	124.7	–	–	–
8	14.2	1.02 (3H, d, J =	–	C-6	7	72.5	5.53 (1H, s)	–	C-6a, 8,	7	41.1	2.36 (Ha) (1H, d,	–	C-6a, 8
		7.22)							9			J = 4.65)
												2.07 (Hb) (1H, d,
												J = 5.15)
3 ʹ	41.2	2.42 (1H, m)	H-4 ʹ	C-7, 1 a,	8	98.6	–	–	–	8	97.8	–	–	–
				2 a
4 ʹ	27.7	1.67 (1H, m)		C-5 ʹ	9	170.9	–	–	–	3 ʹ	41.7	2.99 (1H, d, J =	H-4 ʹ	C-8, 1 a
												7.46)
5 ʹ	43.1	1.52 (Ha) (1H, dd, J	H-6 ʹ	C-6 ʹ	10	21.2	2.23 (3H, s)	–	C-9	4 ʹ	71.4	5.42 (1H, dt,	H-5 ʹ	C-5 ʹ, 8 ʹ
		= 10.09, 4.96)										5.22, 7.44)
		1.46 (Hb) (1H, dd, J
		= 10.09, 4.66)
6 ʹ	68.5	3.75 (1H, m)	H-7 ʹ	C-7	3 ʹ	35.6	2.37 (1H, m)	H-4 ʹ	C-8, 1 a,	5 ʹ	35.6	1.92 (Ha) (1H, m)	H-6 ʹ	C-6 ʹ
									2 a			1.65 (Hb) (1H, m)
7 ʹ	22.8	1.11 (3H, d, J =	–	C-6 ʹ	4 ʹ	23.4	1.72 (Ha) (1H, m)	H-5 ʹ	C-3 ʹ	6 ʹ	68.2	3.75 (1H, m)	H-7 ʹ	C-8
		5.45)					1.38 (Hb) (1H, m)
8 ʹ	19.3	0.96 (3H, d, J =	–	C-4 ʹ	5 ʹ	29.5	1.51 (Ha) (1H, m)	H-6 ʹ	–	7 ʹ	21.9	1.20 (3H, d, J =	–	C-6 ʹ
		6.79)					1.45 (Hb) (1H, m)					6.64)
1 a	33.4	2.27 (Ha) (1H, d, J	–	C-2 a	6 ʹ	68.0	3.68 (1H, m)	H-7 ʹ	C-8, 5 ʹ	8 ʹ	170.8	–	–	–
		= 5.85)
		2.10 (Hb) (1H, d, J
		= 5.66)
2 a	175.6	–	–	–	7 ʹ	19.1	1.11 (3H, d, J =	–		9 ʹ	21.2	2.21 (3H, s)	–	C-8 ʹ
							7.65)
3 a	64.2	4.17 (2H, t, J =	H-4 a	C-2 a	1 a	36.7	2.30 (Ha) (1H, d,	–	C-2 a	1 a	132.4	–	–	–
		8.76)					J = 6.33)
2.08 (Hb) (1H, d,
							J = 6.15)
4a	30.0	2.24 (2H, q, J =	H-5a	C-5a	2a	174.1	–	–	–	2a	125.1	5.33 (1H, t, J =	H-3a	C-1a,
		6.92)										8.65)		3 a
5 a	120.6	5.20 (1H, t, J =	–	C-3 a, 6 a	3 a	64.5	4.64 (2H, d, J =	H-4 a	C-2 a, 4 a	3 a	28.1	1.99 (2H, m)	–	C-4 a
		7.05)					7.25)
6 a	131.7	–	–	–	4 a	129.5	5.37 (1H, q, J =	–	5 a	4 a	27.4	2.01 (2H, m)	H-5 a	–
							6.75)
7 a	24.8	1.76 (3H, s)	–	6a	5a	135.1	5.28 (1H, q, J =	H-6a	–	5a	123.5	5.23 (1H, t, J =	–	C-4a,
							7.05)					6.82)		6 a
8 a	17.9	1.79 (3H, s)	–	6 a	6 a	25.5	2.01 (2H, m)	H-7 a	5 a	6 a	130.2	–	–	–
					7 a	14.3	1.02 (3H, d, J =	–	6 a	7 a	24.6	1.84 (3H, s)	–	6 a
							8.65)
										8 a	18.6	1.74 (3H, s)	–	6a
										9a	19.0	1.81 (3H, s)	–	1a