Punctaporonins N–S, New Caryophyllene Sesquiterpenoids from Cytospora sp.

Table 1

NMR data (400 MHz, Acetone-d₆) for punctaporonin N (1).

Position	, mult.	(J in Hz)	HMBC	NOESY
1	140.0, qC
2	39.8, CH	3.39, dd (11.9, 8.2)	1, 3, 5, 11, 12	13
3a	34.0, CH2	2.15, dd (11.9, 9.8)	1, 2, 4, 13, 14
3b		1.49, dd (9.8, 8.2)	2, 4, 5, 13	13
4	41.0, qC
5	82.7, qC
6	71.4, CH	3.86, br d (4.7)		13, 16
7a	42.5, CH2	2.63, dd (16.3, 4.7)	5, 6, 15
7b		1.64, dt (16.3, 2.0)	6, 8, 9, 15
8	78.4, qC
9	141.9, CH	5.70, dt (13.0, 2.0)	7, 10, 11
10	124.5, CH	5.62, d (13.0)	1, 9
11	125.9, CH	5.88, s	1, 2, 9, 12	12b
12a	64.8, CH2	4.19, d (12.0)	1, 11
12b		3.93, d (12.0)	1, 2, 11	11, 13
13	24.6, CH3	1.23, s	3, 4, 5, 14	2, 3b, 6, 12b
14	24.1, CH3	1.07, s	3, 4, 5, 13	OH-5
15	26.0, CH3	1.10, s	7, 8, 9	16
16	48.7, CH3	3.26, s	8	6, 15
OH-5		4.53, br s		14
OH-6		4.67, br s
OH-12		3.14, br s

correlations, optimized for 8 Hz, are from proton(s) stated to the indicated carbon.