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. 2019 Feb 14;24(4):684. doi: 10.3390/molecules24040684

Table 1.

Relative concentrations of the major compounds identified in resin and hydrogenated resin of Azorella compacta.

Structure Number a Compound Composition b MW ID c Resin (n = 7) Hydrogenated Resin (n = 4)
I Spathulenol C15H24O 220 S 1.4
II Spathulanol C15H26O 222 S 3
III 20-Normulina-11,13-diene C19H30 258 T 0.5
IV 20-Norazorell-13-ene C19H30 258 T 1
V 20-Norazorellane, α + β C19H32 260 T 1
VI 20-Normulinane, α + β C19H34 262 T 0.3
VII 13β(H)-Azorell-14-ene C20H32 272 T 9
VIII Azorell-13-ene C20H32 272 I 2
IX 13α(H)-Azorell-14-ene C20H32 272 T 2.5
X 13β(H)-Mulina-11,14-diene C20H32 272 I 16
XI Mulina-11,13-diene C20H32 272 L 7
XII 13α(H)-Mulina-11,14-diene C20H32 272 I 4
XIII 13β(H)-Azorellane C20H34 274 I 26
XIV 13α(H)-Azorellane C20H34 274 I 15
XV 13β(H)-Mulinane C20H36 276 I 11
XVI 13α(H)-Mulinane C20H36 276 I 8
XVII 13-Hydroxyazorellanes C20H34O 290 L 14
XVIII 13α-Hydroxymulinane C20H36O 292 L 22
XIX 13β(H)-Mulina-11,14-dien-20-oic acid C20H30O2 302 S 10
XX Mulina-11,13-dien-20-oic acid C20H30O2 302 S 100
XXI Azorell-13-en-20-oic acid C20H30O2 302 S 17
XXII 13β(H)-Azorellan-20-oic acid C20H32O2 304 S 5
XXIII 13α(H)-Azorellan-20-oic acid C20H32O2 304 S 30
XXIV 13β(H)-Mulinan-20-oic acid C20H34O2 306 S 44
XXV 13α(H)-Mulinan-20-oic acid C20H34O2 306 S 100
XXVI Mulinol C20H34O2 306 L 7
XXVII Dihydromulinol C20H36O2 308 I 6
XXVIII 13α-Hydroxymulin-11-en-20-oic acid C20H32O3 320 S 8
XXIX 13α-Hydroxymulinan-20-oic acid C20H34O3 322 S 25
XXX 20-Acetoxymulina-11,13-diene C22H34O2 330 L 15
XXXI 13α,14β-Dihydroxymulin-11-en-20-oic acid C20H30O4 336 L 11
XXXII 13α,14β-Dihydroxymulinan-20-oic acid C20H34O4 338 I 32
XXXIII Azorellanol C22H36O3 348 L 16 12

a Structures are shown in Appendix A. b Listed as the natural products, polar compounds analyzed as methyl esters and/or trimethylsilyl derivatives. c Identification: I = interpretation and correlation of MS fragmentation pattern and GC retention time as derivative from standard, T = suggested interpretation based on MS and GC retention time only, S = standard, L = literature citation, n = number of analyses.