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

Table 2

NMR spectroscopic data for punctaporonins O–Q (2–4) in acetone-d₆.

Position	2		3		4
	, mult.	(J in Hz)	, mult.	(J in Hz)	, mult.	(J in Hz)
1	55.3, qC		55.6, qC		53.6, qC
2	47.1, CH	2.54, dd (13.0, 8.0)	47.2, CH	2.32, dd (12.8, 7.8)	45.6, CH	2.35, dd (12.5, 7.9)
3a	35.5, CH2	2.02, dd (13.0, 8.0)	35.5, CH2	2.08, dd (12.8, 8.9)	36.3, CH2	2.13, dd (12.5, 9.2)
3b		1.46, t (8.0)		1.52, dd (8.9, 7.8)		1.46, dd (9.2, 7.9)
4	42.8, qC		42.9, qC		42.7, qC
5	80.6, qC		80.4, qC		81.7, qC
6	68.9, CH	4.09, dd (10.0, 5.6)	68.7, CH	4.06, ddd (10.3, 7.9, 5.6)	68.9, CH	4.17, dd (10.0, 5.9)
7a	41.5, CH2	1.86, dd (13.5, 5.6)	41.2, CH2	1.77, dd (14.0, 5.6)	40.3, CH2	1.90, dd (13.5, 5.9)
7b		1.56, dd (13.5, 10.0)		1.62, dd (14.0, 10.3)		1.64, dd (13.5, 10.0)
8	51.0, qC		50.0, qC		50.9, qC
9	97.3, CH	3.60, d (2.0)	89.4, CH	5.11, d (2.5)	86.5, CH	4.07, d (2.5)
10	127.9, CH	5.90, dd (6.0, 2.0)	126.6, CH	5.67, dd (5.9, 2.5)	130.6, CH	5.68, dd (6.0, 2.5)
11	143.4, CH	5.74, d (6.0)	145.3, CH	5.88, d (5.9)	141.2, CH	5.92, d (6.0)
12a	62.2, CH2	3.68, d (11.4)	62.0, CH2	3.73, d (11.2)	65.6, CH2	4.57, d (11.6)
12b		3.40, d (11.4)		3.48, dd (11.2, 8.0)		4.37, d (11.6)
13	23.4, CH3	1.11, s	23.4, CH3	1.19, s	23.3, CH3	1.10, s
14	24.1, CH3	1.08, s	24.0, CH3	1.12, s	23.7, CH3	1.05, s
15	24.6, CH3	1.05, s	24.3, CH3	1.10, s	26.2, CH3	0.84, s
16	57.5, CH3	3.33, s
OH-5		4.82, br s		4.88, s
OH-6		5.39, br s		5.37, d (7.9)
OH-9						3.29, s
OH-12		3.25, br s		3.44, d (8.0)
Ac-9			21.3, CH3	2.03, s
			170.4, qC
Ac-12					21.0, CH3	1.93, s
					171.0, qC

at 100 MHz. at 500 MHz.