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

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© 2019 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Mass spectra of the oxygenated diterpenoids in A. compacta resins, including KI values shown in parentheses: (a) 13β-hydroxyazorellane (XVII), (b) 13α-hydroxyazorellane (XVII), (c) 13α-hydroxymulinane (XVIII), (d) 13β(H)-mulina-11,14-dien-20-oic acid (XIX, standard), (e) mulina-11,13-dien-20-oic acid (XX, standard), (f) azorell-13-en-20-oic acid (XXI, standard), (g) 13β(H)-azorellan-20-oic acid (XXII, standard), (h) 13α(H)-azorellan-20-oic acid (XXIII, standard), (i) 13β(H)-mulinan-20-oic acid (XXIV, standard), (j) 13α(H)-mulinan-20-oic acid (XXV, standard), (k) methyl mulina-11,13-dien-20-oate (XX, standard), (l) methyl 13β(H)-mulina-11,14-dien-20-oate (XIX, standard), (m) methyl 13β(H)-mulinan-20-oate (XXIV, standard), (n) methyl 13α(H)-mulinan-20-oate (XXV, standard), (o) methyl azorell-13-en-20-oate (XXI, standard), (p) 20-acetoxymulina-11,13-diene (XXX), (q) 13α,14β-dihydroxymulinan-20-oic acid (XXXII), (r) azorellanol (XXXIII, standard), (s) mulinol-diTMS (XXVI), (t) dihydomulinol-diTMS (XXVII), (u) 13α-hydroxymulin-11-en-20-oic acid-diTMS (XXVIII, mulinolic acid-diTMS, standard), (v) 13α-hydroxymulinan-20-oic acid-diTMS (XXIX, standard), (w) 13α,14β-dihydroxymulin-11-en-20-oic acid-triTMS (XXXI), and (x) 13α,14β-dihydroxymulinan-20-oic acid-triTMS (XXXII).

Mass spectra of the oxygenated diterpenoids in A. compacta resins, including KI values shown in parentheses: (a) 13β-hydroxyazorellane (XVII), (b) 13α-hydroxyazorellane (XVII), (c) 13α-hydroxymulinane (XVIII), (d) 13β(H)-mulina-11,14-dien-20-oic acid (XIX, standard), (e) mulina-11,13-dien-20-oic acid (XX, standard), (f) azorell-13-en-20-oic acid (XXI, standard), (g) 13β(H)-azorellan-20-oic acid (XXII, standard), (h) 13α(H)-azorellan-20-oic acid (XXIII, standard), (i) 13β(H)-mulinan-20-oic acid (XXIV, standard), (j) 13α(H)-mulinan-20-oic acid (XXV, standard), (k) methyl mulina-11,13-dien-20-oate (XX, standard), (l) methyl 13β(H)-mulina-11,14-dien-20-oate (XIX, standard), (m) methyl 13β(H)-mulinan-20-oate (XXIV, standard), (n) methyl 13α(H)-mulinan-20-oate (XXV, standard), (o) methyl azorell-13-en-20-oate (XXI, standard), (p) 20-acetoxymulina-11,13-diene (XXX), (q) 13α,14β-dihydroxymulinan-20-oic acid (XXXII), (r) azorellanol (XXXIII, standard), (s) mulinol-diTMS (XXVI), (t) dihydomulinol-diTMS (XXVII), (u) 13α-hydroxymulin-11-en-20-oic acid-diTMS (XXVIII, mulinolic acid-diTMS, standard), (v) 13α-hydroxymulinan-20-oic acid-diTMS (XXIX, standard), (w) 13α,14β-dihydroxymulin-11-en-20-oic acid-triTMS (XXXI), and (x) 13α,14β-dihydroxymulinan-20-oic acid-triTMS (XXXII).