Chemical examination of the wax from needles of black spruce (Picea mariana) and balsam fir (Abies balsamea)

Abstract

A waxlike substance extracted from the needles of black spruce by means of petroleum ether gives, upon saponification, capric, lauric, myristic, pentadecanoic, palmitic, stearic, oleic, linoleic, linolenic, arachidic, behenic, lignoceric acids, and one acid not identified. Acids of the C-20 to C-24 series constitute approximately 38 % of the total acids. The unsaturated acids present are mostly of the C-18 series. The acids were identified by the gas-liquid chromatography (g.1.c.) of their methyl esters.The constituent acids of the waxlike substance from balsam fir needles are capric, lauric, myristic, pentadecanoic, palmitic, palmitoleic, heptadecanoic, stearic, oleic, linoleic, linolenic, arachidic, behenic, lignoceric, and about 7 more, not identified. The acids of the C-20 to C-24 series are presenl to the extent of ca. 20%. About 55 % of the acids are of the C-18 series, which is mostly unsaturated. There are present certain unsaturated acids, ca. 5 %, of the C-20 to C-22 series.10-Nonacosanol has been isolated from the unsaponifiable matter remaining after saponification of the waxlike substances from black spruce and balsam fir foliage. Its identity has been established by infrared, nuclear magnetic resonance, and mass spectrometry.

Variability of n‐Alkanes and Nonacosan‐10‐ol in Natural Populations of Picea omorika

“…The CPI total of the P. omorika populations (average of populations I -III) ranged from 3.3 to 11.5 (mean of 5.9), which are similar or slightly lower values than those reported for P. breweriana (4.7 -6.7) and P. abies (5.9), but higher than that reported for P. sitchensis (2.8) [40]. The maximum CPI values of the long-chain nalkanes were 7.4 (CPI [25][26][27][28][29][30][31][32][33] ) and 6.7 (CPI [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] ), while those of the short-chain n-alkanes (CPI [15][16][17][18][19][20][21] ) ranged from 0.0 to 2.7 (0.6 in average; Table 3) and exhibited even/odd predominance (EOP; because a CPI < 1 indicates EOP, and a CPI > 1 denotes OEP) [53].…”

“…The average chain length (ACL) of the total odd-numbered and even-numbered LNAs (ACL total ) was calculated by using the equation of Poynter and Eglington [52]. To compare the obtained results with those from literature sources, CPI [25][26][27][28][29][30][31][32][33] , CPI [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] , CPI [15][16][17][18][19][20][21] , and CPI [25][26][27][28][29][30][31] were calculated by using the equation of Bray and Evans [51] and ACL [23][24][25][26][27][28][29]…”

Labdane-type diterpenoids from Juniperus communis needles

“…Abies balsamea -needles 10-n-C 29 -ol Beri and Lemon, 1970 Abies balsamea -leaves 10-n-C 29 -ol Adenophora tetraphlla -roots 10-n-C 29 -ol Yao et al, 2007 Agathis australis -leaves 10-n-C 27 -ol; 10-n-C 29 -ol; 10-n-C 31 -ol Aquilegia alpinum -leaves n -C 29 -ol Arabidopsis thaliana -stems 14-n-C 29 -ol; 15-n-C 29 -ol Hannoufa et al, 1993 Arabidopsis thaliana -leaves and stems 13-n-C 27 -ol; 14-n-C 27 -ol; 14-n-C 29 -ol; 15-n-C 29 -ol; 15-n-C 31 -ol; 16-n-C 31 -ol Rashotte et al, 2001 Brassica oleracea 14-n-C 29 -ol; 15-n-C 29 -ol Netting and Macey, 1971 Brassica oleracea -leaves 13-n-C 27 -ol; 13-n-C 28 -ol; 13-n-C 29 -ol; 13-n-C 30 -ol; 13-n-C 31 -ol; 14-n-C 29 -ol; 15-n-C 29 -ol Chamaecyparis lawsoniana 9-n-C 27 -ol; 9-n-C 28 -ol; 9-n-C 29 -ol; 9-n-C 31 -ol; 10-n-C 29 -ol; 11-n-C 29 -ol Chelidonium majus -leaves 10-n-C 27 -ol; 10-n-C 28 -ol; 10-n-C 29 -ol; 10-n-C 30 -ol; 10-n-C 31 -ol Cirsium arvense -not reported 10-n-C 29 -ol Tulloch and Hoffman, 1982 Clarkia elegans -leaves 10-n-C 27 -ol; 10-n-C 28 -ol; 10-n-C 29 -ol; 10-n-C 31 -ol Cocculus hirsutus -not reported 10-n-C 29 -ol Ahmad et al, 1987 Crataegus sp. -fruits and leaves 14-n-C 29 -ol Wollrab, 1969 Encephalartos spp.…”

“…13-n-C 33 -ol; 14-n-C 33 -ol Baker and Hunt, 1979 Ginkgo biloba -leaves 10-n-C 27 -ol; 10-n-C 28 -ol; 10-n-C 29 -ol; 10-n-C 30 -ol; 10-n-C 31 -ol Ginkgo biloba -leaves 10-n-C 27 -ol; 10-n-C 28 -ol; 10-n-C 29 -ol; 13-n-C 29 -ol Casal and Moyna, 1979 Juniperus macropoda -berries 10-n-C 29 -ol Juniperus pinchotti 10-n-C 29 -ol Juniperus scopulorum -leaves 10-n-C 29 -ol Lonicera hypoleuca -leaves 10-n-C 29 -ol Khan and Shoeb, 1985 Malus domestica -cuticle fruit 10-n-C 29 -ol Veraverbeke et al, 2001 Papaver bracteatum -leaves 10-n-C 29 -ol Theuns et al, 1985 Papaver somniferum -leaves 13-n-C 27 -ol; 13-n-C 29 -ol; 13-n-C 30 -ol; 14-n-C 29 -ol; 15-n-C 29 -ol Picea abies -needles 10-n-C 29 -ol, 6-n-C 29 -ol, 10-n-C 31 -ol Picea glauca -leaves 10-n-C 29 -ol Picea mariana -needles 10-n-C 29 -ol Beri and Lemon, 1970 Picea pungens -leaves n -C 29 -ol Picea sitchensis -leaves 8-n-C 27 -ol; 9-n-C 27 -ol; 9-n-C 28 -ol; 9-n-C 29 -ol; 9-n-C 30 -ol; 9-n-C 31 -ol; 10-n-C 27 -ol; 10-n-C 29 -ol; 11-n-C 29 -ol Pinus canariensis -needles 10-n-C 29 -ol Pinus halepensis -needles 10-n-C 29 -ol Pinus sylvestris -pollen 10-n-C 29 -ol Caldicott and Eglinton , 1975 Piper atenuatum -leaves 8-n-C 31 -ol Sumathykutty and Rao, 1991 Pisum sativum -leaves 16-n-C 31 -ol; 15-n-C 31 -ol Macey and Barber, 1970 Pisum sativum -leaves 13-n-C 29 -ol; 14-n-C 29 -ol; 15-n-C 29 -ol; 13-n-C 30 -ol; 14-n-C 30 -ol; 15-n-C 30 -ol; 12-n-C 31 -ol;…”

Chemodiversity of Nonacosan‐10‐ol and n‐Alkanes in the Needle Wax of Pinus heldreichii

“…This compound is also often present in vegetative and generative organs of a number of herbs and deciduous flowering plants [8] [9] [14]. In addition to chemical investigations of the surfaces of leaves [15] [16], flowers [17], and fruits [18], nonacosan-10-ol was often investigated in comparative studies between the chemical composition and the morphology of leaf cuticles [19 -23] as well as in wax biosynthesis studies [24] [25], detection of subspecies or hybrids [26], and in environmental studies [27] [28], etc.…”