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. 2019 Jul 2;9(14):8201–8213. doi: 10.1002/ece3.5390
Compounds Exp RI Lit RI CAS number Green needles Senescent needles Needle litter Roots
Peak area Percentage Peak area Percentage Peak area Percentage Peak area Percentage
Monoterpenes
α‐Thujene 925 924 2867‐05‐2   Tr. 358,134 0.1 410,338 0.1    
α‐Pinene* 930 932 80‐56‐8 10,346,907 4.6 17,524,595 5.8 19,951,489 3.4 10,054,231 18.0
Sabinene 971 969 3387‐41‐5 1,572,906 0.7 6,618,945 1.8 10,598,025 1.8   Tr.
Myrcene* 990 988 123‐35‐3 36,174,796 16.0 28,934,513 7.0 40,881,515 7.0 465,899 0.8
3‐Carene* 1,006 1,008 13466‐78‐9 9,039,854 4.0 9,172,857 3.0 13,243,330 2.3 305,225 0.5
α‐Terpinene* 1,014 1,014 99‐86‐5 378,716 0.2 881,019 0.3 2,353,116 0.4    
p‐Cymene* 1,023 1,020 99‐87‐6 2,090,340 0.9 4,847,511 1.6 11,897,482 2.0 212,077 0.4
Limonene* 1,027 1,024 138‐86‐3 2,384,835 1.1 5,735,130 1.9 12,187,549 2.1 643,660 1.1
β‐Ocimene, cis‐ 1,039 1,032 3338‐55‐4   Tr.   Tr. 501,366 0.1    
β‐Ocimene, trans‐ 1,049 1,044 3779‐61‐1 1,134,531 0.5 2,726,094 0.9 4,706,409 0.8    
γ‐Terpinene* 1,058 1,054 99‐85‐4 1,433,499 0.6 2,779,971 0.9 6,473,793 1.1    
δ‐Terpinene 1,086 1,086 586‐62‐9 7,751,217 3.4 17,922,640 6.0 39,209,696 6.7 270,637 0.4
p‐Mentha‐1,3,8‐triene 1,106 1,108 18368‐95‐1     884,388 0.3 1,006,077 0.2    
p‐Mentha‐1,5,8‐triene 1,110 1,112 21195‐59‐5   Tr. 327,055 0.1 741,572 0.1    
Oxygenated monoterpenes
Mentha‐2,8‐dien‐1‐ol 1,132 1,133 3886‐78‐0 152,253 0.1 491,005 0.2        
Camphor* 1,140 1,141 76‐22‐2 200,666 0.1 1,385,989 0.5 954,450 0.2   Tr.
3‐Pinanone, trans‐ 1,156 1,158 547‐60‐4 461,983 0.2 523,886 0.2 1,386,736 0.2    
Pinocarvone 1,158 1,160 30460‐92‐5     455,894 0.2   Tr.    
3‐Pinanone, cis‐ 1,168 1,172 15358‐88‐0 625,857 0.3 1,928,458 0.6 2,276,193 0.4    
4‐Terpineol* 1,174 1,174 562‐74‐3 812,368 0.4 3,588,528 1.2 2,901,480 0.5    
p‐Cymen‐8‐ol 1,181 1,179 1197‐01‐9   Tr. 596,384 0.2 422,419 0.1    
α‐Terpineol* 1,190 1,186 98‐55‐5 155,272 0.1 569,885 0.2 594,605 0.1    
Verbenone* 1,203 1,204 80‐57‐9 196,893 0.1 317,261 0.1 320,962 0.1 186,682 0.3
Monoterpene derivates
Carvacrol, methyl ether 1,242 1,241 6379‐73‐3   Tr. 306,988 0.1 360,329 0.1    
Isoborneol, acetate 1,283 1,283 125‐12‐2     500,659 0.2 548,059 0.1   Tr.
Sesquiterpenes
α‐Cubebene 1,348 1,345 31141‐66‐9 308,896 0.1 478,395 0.2 1,622,287 0.3   Tr.
Cyclosativene 1,364 1,369 30541‐92‐5 912,179 0.4 412,837 0.1 1,267,626 0.2 608,193 1.1
Copaene 1,374 1,374 13567‐62‐9 3,866,030 1.7 4,645,349 1.5 10,363,372 1.8 2,976,659 5.3
β‐Bourbonene 1,383 1,387 13828‐08‐5 198,267 0.1 256,843 0.1 987,030 0.2   Tr.
β‐Cubebene 1,388 1,387 23526‐21‐8 237,280 0.1 286,492 0.1 923,549 0.2 107,540 0.2
β‐Elemene 1,392 1,389 33880‐83‐0 223,101 0.1 550,915 0.2 1,287,407 0.2   Tr.
Longifolene* 1,402 1,407 475‐20‐7         426,933 0.1 1,485,812 2.6
Isocaryophyllene 1,408 1,408 61217‐74‐1 1,004,437 0.4 849,294 0.3 2,518,016 0.4   Tr.
β‐Caryophyllene* 1,417 1,417 17627‐40‐6 78,630,885 34.8 108,704,883 36.2 310,965,356 53.3 14,269,696 25.6
β‐Copaene 1,429 1,430 18252‐44‐3 1,062,919 0.5 2,303,947 0.8 5,304,121 0.9 1,505,045 2.7
α‐Guaiene 1,438 1,437 3691‐12‐1   Tr. 423,833 0.1 961,784 0.2    
Guaia‐6,9‐diene 1,443 1,442 37839‐64‐8 333,554 0.1 598,957 0.2 1,878,411 0.3    
α‐Himachalene 1,449 1,449 41702‐31‐2   Tr. 739,854 0.2     154,872 0.3
α‐Caryophyllene* 1,453 1,452 6753‐98‐6 15,738,469 7.0 20,909,453 7.0 663,457 0.1 2,456,448 4.4
Cadina‐1(6), 4‐diene, trans‐ 1,474 1,475 931410‐54‐7   Tr. 484,498 0.2 589,353 0.1    
γ‐Muurolene 1,478 1,478 30021‐74‐0 958,492 0.4 2,379,018 0.8 2,421,011 0.4 876,675 1.6
Germacrene D 1,482 1,484 105453‐16‐5 199,903 0.1 274,159 0.1 888,134 0.2 473,752 0.8
β‐Selinene 1,492 1,489 21488‐94‐8 369,225 0.2 516,694 0.2 2,314,984 0.4    
α‐Muurolene 1,502 1,500 31983‐22‐9 5,890,566 2.6 5,269,095 1.8 5,470,007 0.9 12,505,286 22.3
α‐Farnesene, trans, trans‐ 1,510 1,505 502‐61‐4 245,532 0.1 504,495 0.2 549,898 0.1 168,261 0.2
γ‐Cadinene 1,516 1,513 39029‐41‐9 295,765 0.1 745,112 0.2 484,686 0.1   Tr.
δ‐Cadinene 1,524 1,522 60305‐17‐1 2,273,959 1.0 1,615,905 0.6 3,872,377 0.7 812,058 1.4
Cadina‐1,4‐diene 1,535 1,533 16728‐99‐7 183,093 0.1 242,526 0.1 449,617 0.1    
Oxygenated sesquiterpenes
Caryophyllene oxide* 1,585 1,582 1139‐30‐6 10,874,006 4.8 8,156,453 2.7 10,138,100 1.7 1,643,386 2.9
Humulene oxide II 1,613 1,608 67737‐67‐1 1,610,896 0.7 1,375,880 0.5 1,311,156 0.2 249,478 0.4

Abbreviations: CAS Number, Chemical Abstracts Service Number; Exp RI, Experimental Retention Index calculated with the formula of van Den Dool and Kratz (1963); Lit RI, Literal Retention Index based on Adams (2007); Peak area, peak area of the compound in the chromatogram; Percentage, peak surface percentage in the chromatogram; Tr., Traces (peak surface percentage < 0.1%).

*

Identification confirmed by commercial standard coinjection.