Wood Science and Technology

Electronic Supplementary Material for

Bioactivity and characterization of exudates from Cryptomeria japonica bark

Sen Sung Cheng．Shang Tzen Chang

S. S. Cheng

Experimental Forest, National Taiwan University, No. 12, Section 1, Chien-Shan Road, Chu-Shan, Nantou Hsien 55750, Taiwan

S. T. Chang ()

School of Forestry and Resource Conservation, National Taiwan University, No. 1, Section 4, Roosevelt Road, Taipei 10617, Taiwan. Tel.: +886-2-33664626; fax: +886-2- 23654520.

e-mail: (S.T. Chang)


Ferruginol (1). Yellow oil; EI-MS for C20H30O found 286; IR νmax : 3370, 1612, 1501, 1440 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.89 (3H, s, H-18), 0.92 (3H, s, H-19), 1.15 (3H, s, H-20),1.20 (3H, d, J = 7.0 Hz, H-16), 1.23 (3H, d, J = 7.0 Hz, H-17), 2.77 (1H, ddd, J = 17.0, 10.5, 7.0 Hz, H-7α), 2.81(1H, ddd, J = 2.0, 6.5, 17.0 Hz, H-7β), 3.09 (sept, J = 7.0 Hz, H-15), 6.61 (1H, s, H-11), 6.81 (1H, s, H-14); 13C NMR : δ(ppm) 19.21 (C-6), 19.30 (C-2), 21.61 (C-19), 22.54 (C-16), 22.73 (C-17), 24.78 (C-20), 26.79 (C-15), 29.74 (C-7), 33.30 (C-18), 33.42 (C-4), 37.49 (C-10), 38.85 (C-1), 41.67 (C-3), 50.33 (C-5), 110.95 (C-11), 126.60 (C-14), 127.283 (C-8), 131.35 (C-13), 148.66 (C-9), 150.64 (C-12).

Cryptojaponol (2). Solid; EI-MS for C21H30O3 found 330; IR νmax : 3432, 2963, 1735, 1417, 1362, 1225 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.92 (3H, s, H-18), 0.96 (3H, s, H-19), 1.21(3H, d, J = 7.0 Hz, H-16), 1.23 (3H, d, J = 7.0 Hz, H-17), 1.37 (3H, s, H-20), 1.85 (1H, dd, J = 14.0, 3.1 Hz, H-5), 2.53 (1H, dd, J = 17.0, 14.0 Hz, H-6β), 2.61 (1H, dd, J = 17.0, 3.1 Hz, H-6α), 3.19 (sept, J = 7.0 Hz, H-15), 3.21 (1H, br d, J = 12.0 Hz, H-1β), 3.79 (3H, s, OMe), 7.59 (1H, s, H-14); 13C NMR : δ(ppm) 18.04 (C-2), 19.00 (C-20), 21.50 (C-19), 23.47 (C-16), 23.55 (C-17), 26.70 (C-15), 33.14 (C-18), 33.47 (C-4), 35.66 (C-6), 36.29 (C-1), 40.22 (C-10), 41.26 (C-3), 50.32 (C-5), 61.84 (OMe), 117.34 (C-14), 128.87 (C-8), 138.10 (C-11), 139.07 (C-13), 146.47 (C-9), 149.11 (C-12), 199.14 (C-7).

Isopimaric acid (3). Solid; EI-MS for C20H30O2 found 302; IR νmax : 3500-2500, 1697 (-COOH), 908, 833 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.84 (3H, s, H-20), 0.89 (3H, s, H-17), 1.25 (3H, s, H-19), 4.86 (1H, dd, J = 10.8, 1.2 Hz, H-16), 4.90 (1H, dd, J = 17.5, 1.2 Hz, H-16), 5.30 (1H, br d, J = 4.9 Hz, H-7), 5.77 (1H, dd, J = 17.5, 10.8 Hz, H-15), 13C NMR : δ(ppm) 15.27 (C-20), 17.09 (C-19), 17.91 (C-2), 19.99 (C-11), 21.46 (C-17), 25.14 (C-6), 34.97 (C-10), 36.04 (C-12), 36.79 (C-13), 36.97 (C-3), 38.77 (C-1), 44.96 (C-5), 46.04 (C-14), 46.30 (C-4), 51.97 (C-9), 109.25 (C-16), 120.94 (C-7), 135.62 (C-8), 150.27 (C-15), 185.59 (C-18).

7β-Hydroxydeoxocryptojaponol (4). Solid; EI-MS for C21H32O3 found 332; IR νmax : 3240, 3050, 1600, 1500, 1240, 1040 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.92 (3H, s, H-18), 0.93 (3H, s, H-19), 1.21 (3H, d, J = 7.0 Hz, H-16), 1.23 (3H, d, J = 7.0 Hz, H-17), 1.35 (1H, s, H-20), 2.16 (1H, dd, J = 14.0, 3.1 Hz, H-5), 3.10 (2H, br d, J = 13.2 Hz, Hβ-6), 3.18 (sept, J = 7.0 Hz, H-15), 3.74 (3H, s, OMe), 4.68 (1H, dd, J = 11.2, 6.8 Hz, H-7), 6.00 (1H, s, OH), 7.00 (1H, s, H-14); 13C NMR : δ(ppm) 19.14 (C-2), 19.63 (C-20), 21.97 (C-19), 23.70 (C-16), 23.72 (C-17), 26.59 (C-15), 30.16 (C-6), 33.36 (C-4), 33.59 (C-18), 36.24 (C-1), 40.06 (C-10), 41.29 (C-3), 50.11 (C-5), 61.77 (OMe), 71.99 (C-7), 115.62 (C-14), 132.94 (C-8), 136.62 (C-13), 138.463 (C-9), 143.66 (C-11), 146.26 (C-12).

Isopimarol (5). Solid; EI-MS for C20H32O found 288; IR νmax : 3369, 2935, 2870, 1470, 1043, 900 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.84 (3H, s, H-19), 0.87 (3H, s, H-20), 0.89 (3H, s, H-17), 3.14 (1H, d, J = 10.8 Hz, H-18), 3.37 (1H, dd, J = 10.8 Hz, H-18), 4.85 (1H, dd, J = 10.8, 1.3 Hz, H-16), 4.92 (1H, dd, J = 17.5, 1.2 Hz, H-16), 5.32 (1H, br s, H-7), 5.78 (1H, dd, J = 17.5, 10.8 Hz, H-15), 13C NMR : δ(ppm) 15.59 (C-20), 18.11 (C-2), 18.35 (C-19), 20.20 (C-11), 21.47 (C-17), 23.31 (C-6), 35.19 (C-10), 35.58 (C-3), 36.17 (C-12), 36.86 (C-13), 39.40 (C-1), 43.72 (C-5), 46.14 (C-14), 51.81 (C-9), 72.30 (C-18), 109.17 (C-16), 121.21 (C-7), 135.65 (C-8), 150.42 (C-15).

Sandaracopimarinol (6). Gum; EI-MS for C20H32O found 288; IR νmax : 3379, 1640, 1446, 910 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.79 (3H, s, H-19), 0.82 (3H, s, H-20), 1.02 (3H, s, H-17), 3.13 (1H, d, J = 10.7 Hz, H-18), 3.40 (1H, d, J = 10.7 Hz, H-18), 4.85 (1H, dd, J = 10.8, 1.3 Hz, H-16), 4.91 (1H, dd, J = 17.5, 1.3 Hz, H-16), 5.19 (1H, s, H-7), 5.76 (1H, dd, J = 17.5, 10.8 Hz, H-15), 13C NMR : δ(ppm) 15.59 (C-20), 17.93 (C-19), 18.35 (C-2), 18.82 (C-11), 22.43 (C-6), 25.98 (C-17), 34.60 (C-12), 35.50 (C-7), 35.75 (C-3), 37.39 (C-4), 37.80 (C-13), 38.17 (C-10), 38.93 (C-1), 47.98 (C-5), 50.58 (C-9), 72.30 (C-18), 110.00 (C-16), 128.73 (C-14), 136.99 (C-8), 149.12 (C-15).

Phyllocladan-16α-ol (7). Solid; EI-MS for C20H34O found 290; IR νmax : 3343, 2850, 1470, 1378 cm-1; 1H NMR (in CDCl3) : δ(ppm) 0.78 (3H, s, H-19), 0.83 (3H, s, H-18), 0.85 (3H, s, H-20), 1.31 (3H, s, H-17), 2.01 (2H, m, H-14 ), 2.10 (1H, dd, J = 14.7, 1.8 Hz, H-13), 13C NMR : δ(ppm) 14.83 (C-20), 18.36 (C-2), 18.99 (C-11), 20.31 (C-19), 21.96 (C-6), 23.92 (C-17), 27.50 (C-15), 33.11 (C-4), 33.72 (C-18), 37.81 (C-10), 39.41 (C-1), 41.64 (C-7), 44.01 (C-3), 44.52 (C-8), 47.61 (C-13), 49.04 (C-14), 49.76 (C-12), 56.32 (C-5), 57.00 (C-9), 82.20 (C-16).

S1