Table 1 Identification and mass spectral data (m/z-fragments) of the constituents of the Werdenfels resin nodule

Dicyclic terpanes

Trimethyl-decalin

C₁₃H₂₄

180

1

165 (100), 109 (78), 81 (50), 95 (47), 180 (36), 55 (27), 137 (27), 67 (23), 110 (20), 123 (14)

Tetramethyl-decalins (4 possible isomers, only two shown in Fig 6)

C₁₄H₂₆

194

2a

179 (100), 109 (51), 95 (40), 123 (37), 81 (35), 194 (35), 82 (33), 83 (32), 55 (23), 110 (21)

2b

109 (100), 194 (39), 95 (32), 123 (26), 110 (26), 81 (25), 82 (22), 55 (17), 124 (17), 69 (15)

Dicyclic terpenes

Tetramethyl-tetralins (2 isomers)

C₁₄H₂₀

188

3a

132 (100), 188 (41), 117 (36), 159 (27), 173 (17), 131 (16), 133 (14) 174 (11), 129 (11), 115 (10)

3b

173 (100),188 (22), 133 (14), 174 (13), 158 (9), 145 (7), 128 (6), 129 (6), 143 (6), 131 (5)

Trimethyl-tetralins (3 possible isomers, only one shown in Fig. 6)

C₁₃H₁₈

174

4a

159 (100), 174 (32), 160 (14), 131 (13), 144 (10), 129 (10), 128 (9), 146 (7), 115 (6), 173 (6)

1,2,5-Trimethyl-naphthalene (agathalene)

C₁₃H₁₄

170

5

155 (100), 170 (99), 153 (27), 152 (20), 115 (12), 154 (11), 171 (11), 169 (11), 128 (11), 156 (11)

Tricyclic terpanes/terpenes

Trimethyl-perhydrophenanthrene

C₁₇H₃₀

234

6

109 (100), 163 (97), 95 (71), 81 (55), 110 (47), 219 (45), 164 (43), 67 (42), 234 (38), 55 (37)

Octahydro-trimethyl-phenanthrene (2 isomers)

C₁₇H₂₄

228

7a

213 (100), 131 (75), 228 (35), 157 (29), 214 (19), 185 (16), 143 (12), 132 (10), 128 (7), 141 (7)

7b

131 (100), 213 (80), 157 (35), 228 (31), 214 (14), 143 (13), 132 (11), 128 (10), 142 (9), 185 (9)

Tetramethyl-perhydrophenanthrenes (3 isomers)

C₁₈H₃₂

248

8a

109 (100), 177 (71), 95 (62), 81 (60), 233 (44), 69 (38), 55 (35), 248 (35), 67 (34), 110 (31)

8b

177 (100), 109 (60), 95 (39), 81 (38), 110 (37), 248 (31), 178 (23), 55 (20), 67 (20), 69 (18)

8c

109 (100), 248 (70), 81 (52), 95 (49), 110 (42), 55 (30), 67 (26), 124 (26), 82 (25), 233 (23)

Octahydro-tetramethyl-phenanthrene

C₁₈H₂₆

242

9

227 (100), 157 (53), 143 (48), 131 (47), 171 (44), 242 (32), 145 (28), 158 (27), 228 (20), 128 (19)

Pentamethyl-perhydro-phenanthrenes (2 isomers)

C₁₉H₃₄

262

10a

233 (100), 109 (24), 123 (23), 137 (22), 95 (21), 262 (20), 97 (20), 81 (19), 234 (18), 232 (16)

10b

233 (100), 123 (45), 109 (34), 81 (28), 227 (28), 95 (27), 137 (24), 55 (21), 145 (20), 262 (15)

Tetracyclic steranes

‘Androstane’ (2 isomers)

C₁₉H₃₂

260

11a

245 (100), 109 (93), 131 (90), 241 (87), 81 (69), 95 (66), 260 (62), 163 (53), 108 (52), 231 (49)

11b

245 (100), 227 (64), 209 (48), 242 (41), 260 (40), 163 (33), 172 (28), 81 (24), 95 (23), 109 (23)

Allopregnane

C₂₁H₃₆

288

14

288 (100), 273 (81), 217 (63), 109 (44), 81 (44), 95 (34), 67 (31), 289 (25), 55 (24), 218 (22)

Methyl-allopregnane

C₂₂H₃₈

302

15

189 (100), 217 (50), 95 (48), 81 (45), 67 (43), 123 (41), 69 (35), 302 (34), 109 (33), 55 (28)

Not identified

Not identified

–

256

12

131 (100), 241 (82), 157 (38), 233 (23), 256 (22), 171 (20), 143 (17), 242 (17), 145 (16), 132 (14)

Not identified

–

274

13

227 (100), 145 (78), 242 (44), 171 (32), 274 (24), 228 (16), 209 (15), 143 (15), 128 (13), 146 (13)

Not identified

–

316

16

282 (100), 129 (38), 109 (28), 163 (28), 283 (26), 104 (23), 95 (21), 164 (20), 130 (18), 316 (11)

Not identified

–

324

17

309 (100), 132 (51), 105 (46), 119 (39), 310 (30), 81 (29), 324 (28), 145 (26), 173 (25), 199 (22)