Kangaroo Island propolis types originating from two Lepidosperma species and Dodonaea humilis Author King, Douglas I. * & Sydney Pharmacy School, Faculty of Medicine and Health, The University of Sydney, New South Wales, Australia Author Hamid, Kaiser Author Tran, Van H. Author Duke, Rujee K. Author Duke, Colin C. text Phytochemistry 2021 112800 2021-08-31 188 1 11 http://dx.doi.org/10.1016/j.phytochem.2021.112800 journal article 264233 10.1016/j.phytochem.2021.112800 b9848b60-9ad9-4c79-9ecc-1e607bc5271c 1873-3700 8259223

Table 1 1 H NMR spectroscopic data for compounds 1, 2, 3, 4, and 5 (400 MHz, δ in ppm and J values (Hz) in parentheses).

H	Comp. 1 a	Comp. 2 a	Comp. 3b	Comp. 4b	Comp. 5b
a Measured in CDCl relative to TMS. 3 b Measured in CD OD relative to TMS.
1	–	–	–	–	–
2	5.37 dd (8.3, 4.8)	7.32 m	7.31 d (2.0)	7.04 d (8.6)	7.04 d (8.6)
3	3.25 dd (14.3, 4.8), 3.19 dd (14.3, 8.3)	–	–	6.69 d (8.6)	6.69 d (8.6)
4	–	–	–	–	–
5	–	6.82 d (8.8)	6.77 d (8.2)	6.69 d (8.6)	6.69 d (8.6)
6	–	7.32 m	7.27 dd (8.2,2.0)	7.04 d (8.6)	7.04 d (8.6)
1′	–	–	–	–	–
2′	7.25–7.33 m	6.29 d (15.9)	6.24 d (16.0)	–	–
3′	7.25–7.33 m	7.71 d (15.9)	7.57 d (16.0)	6.25 s	6.43 s
4′	7.25–7.33 m	–	–	–	–
5′	7.25–7.33 m	–	–	–	–
6′	7.25–7.33 m	–	–	7.47 s	7.51 s
1′′	–	3.37 bd (7.2)	3.32 bd (6.9)	3.25 bd (7.2)	3.26 bd (7.3)
2′′	6.46 d (16.0)	5.31 bt (7.7)	5.40 bt (6.9)	5.56 bt (7.4)	5.51 bt (7.4)
3′′	7.69 d (16.0)	–	–	–	–
4′′	–	2.06 m	2.10 m, 2.32 m	3.96 s	3.95 s
5′′	–	1.42 m	1.41 m, 1.79 m	1.74 s	1.73 s
6′′	–	1.41 m, 1.64 m	3.27 dd (10.6, 1.6)	–	–
7′′	–	2.46 m	–	–	–
8′′	–	–	1.16 s	–	–
9′′	–	1.15 d (7.1)	1.13 s	–	–
10′′	–	1.75 bs	1.74 bs	–	–
1′′′	–	–	–	–	–
2′′′	7.51 m	–	–	–	–
3′′′	7.39 m	–	–	–	–
4′′′	7.39 m	–	–	–	–
5′′′	7.39 m	–	–	–	–
6′′′	7.51 m	–	–	–	–
α	–	–	–	3.13 t (7.6)	3.17 t (7.5)
β	–	–	–	2.89 t (7.7)	2.90 t (7.6)
C=O	–	–	–	–	–
1-OMe	3.74 s	–	–	–	–
4′-OMe	–	–	–	–	3.86 s
8′′-OMe	–	3.68 s	–	–	–