Relative content of the identified compounds in different solvent extracts of defatted hemp seeds^a (mean ± SD).

Compounds	Run 1	Run 2	Run 3	Run 4	Run 5	Run 6	Run 7	Run 8	Run 9	Run10	Run11	Run12	Run13
Phenolic acids
Benzoic acid	11.46 ± 0.127	7.05 ± 0.750	2.02 ± 0.080	10.13 ± 0.040	9.27 ± 0.064	10.12 ± 0.150	4.19 ± 0.095	8.71 ± 0.006	4.31 ± 0.019	15.73 ± 0.041	10.12 ± 0.070	5.41 ± 0.015	10.01 ± 0.078
p-Coumaric acid	1.01 ± 0.120	0.95 ± 0.049	2.37 ± 0.370	1.25 ± 0.055	0.53 ± 0.015	0.52 ± 0.012	Nd	0.86 ± 0.009	Tr	1.41 ± 0.085	1.37 ± 0.035	0.016 ± 0.005	0.54 ± 0.011
Ferulic acid	3.12 ± 0.417	2.14 ± 0.068	8.57 ± 1.180	3.84 ± 0.029	Nd	1.90 ± 0.034	Nd	2.75 ± 0.053	Nd	3.87 ± 0.313	3.92 ± 0.180	1.49 ± 0.112	1.45 ± 0.018
Sinapic acid	1.16 ± 0.009	0.49 ± 0.003	Tr	0.68 ± 0.011	0.89 ± 0.011	1.02 ± 0.011	0.67 ± 0.004	0.92 ± 0.003	0.72 ± 0.002	1.19 ± 0.004	0.76 ± 0.002	0.83 ± 0.04	0.96 ± 0.015
Total phenolic acids	16.69	11.08	12.96	15.9	10.69	13.56	4.86	13.24	5.03	22.2	16.17	7.75	12.96
Hydroxycinnamic acid amides b
N-trans-caffeoyltyramine isomer	8.16 ± 0.098	1.11 ± 0.101	Nd	3.24 ± 0.005	4.29 ± 0.361	6.58 ± 0.125	2.29 ± 0.012	5.84 ± 0.220	2.48 ± 0.036	12.23 ± 0.080	5.15 ± 0.152	2.34 ± 0.023	6.93 ± 0.161
N-trans-caffeoyltyramine	8.70 ± 0.277	1.25 ± 0.010	Nd	7.17 ± 0.265	14.07 ± 0.330	7.60 ± 0.283	2.08 ± 0.022	24.95 ± 0.083	2.80 ± 0.081	33.83 ± 0.054	9.16 ± 0.166	8.01 ± 0.039	10.87 ± 0.437
N-trans-coumaroyltyramine	Nd	Nd	Nd	Nd	Nd	Nd	Nd	Nd	Nd	Tr	Nd	Nd	Nd
N-feruloyltyramine	3.21 ± 0.009	1.31 ± 0.003	0.87 ± 0.038	2.63 ± 0.060	4.42 ± 0.086	2.91 ± 0.140	0.96 ± 0.012	5.48 ± 0.021	1.36 ± 0.021	7.65 ± 0.043	3.51 ± 0.026	3.02 ± 0.060	3.74 ± 0.074
Tri-p-coumaroylspermidine	3.39 ± 0.134	Nd	Nd	5.59 ± 0.124	8.63 ± 0.342	3.80 ± 0.061	Nd	10.08 ± 0.083	2.45 ± 0.047	11.02 ± 0.648	6.64 ± 0.030	7.47 ± 0.053	6.49 ± 0.114
Total HCA	23.46	3.66	0.87	18.63	31.41	20.88	5.33	46.36	9.09	64.72	24.46	20.85	28.03
Lignanamides b
Cannabisin A	10.36 ± 0.307	2.41 ± 0.003	Nd	5.63 ± 0.025	10.89 ± 0.531	9.04 ± 0.197	3.94 ± 0.004	14.27 ± 0.045	3.55 ± 0.009	21.65 ± 0.004	9.63 ± 0.021	6.05 ± 0.375	10.92 ± 0.071
Cannabisin B	6.07 ± 0.415	Nd	Nd	2.46 ± 0.030	7.74 ± 0.286	4.69 ± 0.168	2.50 ± 0.023	11.18 ± 0.050	1.96 ± 0.010	18.63 ± 0.052	4.98 ± 0.138	4.25 ± 0.291	5.68 ± 0.017
Cannabisin B isomer 1	0.93 ± 0.026	0.34 ± 0.296	Nd	0.71 ± 0.008	0.96 ± 0.026	0.75 ± 0.049	0.55 ± 0.007	1.26 ± 0.004	0.57 ± 0.005	1.75 ± 0.005	0.94 ± 0.007	0.78 ± 0.019	0.94 ± 0.048
Cannabisin B isomer 2	1.51 ± 0.053	0.73 ± 0.022	Nd	1.25 ± 0.078	1.32 ± 0.052	1.00 ± 0.285	0.61 ± 0.002	1.97 ± 0.006	0.67 ± 0.005	2.62 ± 0.011	1.52 ± 0.001	0.99 ± 0.066	1.38 ± 0.008
Demethylgrossamide	1.35 ± 0.024	Nd	Nd	0.91 ± 0.025	1.01 ± 0.054	1.04 ± 0.017	0.57 ± 0.005	1.57 ± 0.009	0.59 ± 0.003	1.98 ± 0.018	1.16 ± 0.107	0.82 ± 0.066	1.30 ± 0.015
Cannabisin C	5.24 ± 0.032	0.89 ± 0.063	Nd	2.96 ± 0.017	5.02 ± 0.420	3.75 ± 0.335	1.29 ± 0.023	6.23 ± 0.078	1.50 ± 0.017	9.26 ± 0.283	4.81 ± 0.011	2.95 ± 0.105	4.01 ± 0.011
Cannabisin C isomer	1.68 ± 0.082	0.65 ± 0.094	Nd	Nd	0.88 ± 0.009	1.12 ± 0.141	Nd	1.40 ± 0.060	0.59 ± 0.008	1.78 ± 0.259	1.70 ± 0.003	0.93 ± 0.089	0.88 ± 0.011
Cannabisin D	5.43 ± 0.213	1.22 ± 0.042	Nd	4.67 ± 0.201	3.95 ± 0.242	4.11 ± 0.460	0.78 ± 0.006	5.58 ± 0.143	2.13 ± 0.032	6.57 ± 0.702	6.39 ± 0.032	4.56 ± 0.029	3.81 ± 0.557
3,3-Didemethylgrossamide	1.20 ± 0.091	Nd	Nd	Nd	1.72 ± 0.143	1.22 ± 0.295	Nd	1.73 ± 0.100	Nd	3.28 ± 0.694	Nd	Nd	1.47 ± 0.398
Cannabisin E	1.85 ± 0.082	Nd	Nd	1.68 ± 0.027	1.98 ± 0.082	1.28 ± 0.016	0.53 ± 0.004	1.84 ± 0.259	0.69 ± 0.009	2.89 ± 0.115	1.90 ± 0.011	1.53 ± 0.038	1.45 ± 0.038
Grossamide K	Nd	Nd	Nd	Nd	Nd	Nd	0.39 ± 0.001	Nd	Nd	Nd	Nd	Nd	Nd
Cannabisin M	3.38 ± 0.162	0.90 ± 0.018	Nd	2.47 ± 0.133	4.36 ± 0.129	3.23 ± 0.107	1.29 ± 0.012	5.38 ± 0.017	1.71 ± 0.022	8.17 ± 0.007	3.47 ± 0.030	3.18 ± 0.031	4.05 ± 0.033
3,3′-demethyl-heliotropamide	1.30 ± 0.104	0.61 ± 0.026	Nd	0.86 ± 0.124	1.33 ± 0.174	1.30 ± 0.076	0.67 ± 0.009	1.66 ± 0.009	0.68 ± 0.092	2.47 ± 0.007	1.12 ± 0.024	1.01 ± 0.039	1.24 ± 0.227
Unnamed condensed trilignanamide	1.95 ± 0.113	0.62 ± 0.026	Nd	1.09 ± 0.102	2.12 ± 0.046	2.02 ± 0.048	0.77 ± 0.018	2.71 ± 0.004	0.95 ± 0.077	3.61 ± 0.019	1.69 ± 0.022	1.53 ± 0.031	2.03 ± 0.232
Cannabisin Q	1.34 ± 0.010	Nd	Nd	0.86 ± 0.035	1.50 ± 0.045	1.10 ± 0.021	0.70 ± 0.007	1.83 ± 0.096	0.76 ± 0.001	2.68 ± 0.027	1.27 ± 0.012	1.18 ± 0.062	1.34 ± 0.032
Cannabisin F	2.74 ± 0.048	0.89 ± 0.042	Nd	1.28 ± 0.082	1.80 ± 0.101	2.04 ± 0.014	0.96 ± 0.004	2.26 ± 0.301	1.18 ± 0.075	3.42 ± 0.007	2.11 ± 0.010	1.35 ± 0.179	2.08 ± 0.033
Isocannabisin N	1.23 ± 0.015	Nd	Nd	0.71 ± 0.017	1.21 ± 0.032	0.80 ± 0.008	Nd	1.47 ± 0.056	0.57 ± 0.003	1.99 ± 0.117	1.15 ± 0.011	1.00 ± 0.029	0.96 ± 0.006
Grossamide	3.68 ± 0.071	0.87 ± 0.015	Nd	2.21 ± 0.159	4.79 ± 0.089	2.91 ± 0.080	0.96 ± 0.011	6.04 ± 0.021	1.49 ± 0.024	8.94 ± 0.023	3.30 ± 0.024	3.63 ± 0.022	3.98 ± 0.070
Cannabisin O	2.28 ± 0.207	Nd	Nd	0.61 ± 0.060	3.08 ± 0.025	1.12 ± 0.018	Nd	3.67 ± 0.040	0.68 ± 0.005	4.53 ± 0.029	1.84 ± 0.086	2.79 ± 0.038	1.57 ± 0.034
Unnamed lignanamide	3.57 ± 0.227	Nd	Nd	0.99 ± 0.022	3.62 ± 0.014	1.80 ± 0.013	Nd	4.70 ± 0.075	0.92 ± 0.009	5.58 ± 0.011	3.07 ± 0.024	3.33 ± 0.055	2.22 ± 0.038
Total lignanamides	57.09	10.13	—	31.34	59.30	44.31	16.54	76.72	21.18	111.81	52.05	41.87	51.32
Total phenylpropanoids	80.55	13.79	0.87	49.96	90.71	65.19	21.87	123.09	30.27	176.53	76.51	62.72	79.35
Cannabinoids b
Dihydrocannabinol	0.67 ± 0.031	0.51 ± 0.003	Nd	0.62 ± 0.002	0.59 ± 0.001	0.65 ± 0.002	Nd	0.60 ± 0.007	0.52 ± 0.003	0.64 ± 0.002	0.65 ± 0.002	0.57 ± 0.017	0.62 ± 0.006
Cannabidiol (CBD)	0.56 ± 0.005	Nd	Nd	0.50 ± 0.002	0.56 ± 0.002	0.57 ± 0.007	Nd	0.54 ± 0.003	0.53 ± 0.012	0.63 ± 0.040	0.52 ± 0.004	0.53 ± 0.008	0.61 ± 0.006
Cannabielsoic acid	1.67 ± 0.028	0.60 ± 0.002	Nd	1.04 ± 0.016	1.53 ± 0.016	1.86 ± 0.022	0.98 ± 0.020	1.58 ± 0.033	1.16 ± 0.012	1.85 ± 0.055	1.08 ± 0.002	1.37 ± 0.024	1.81 ± 0.024
Cannabidiolic acid (CBDA)	1.12 ± 0.007	Nd	Nd	0.57 ± 0.004	1.04 ± 0.021	1.33 ± 0.037	0.97 ± 0.005	1.05 ± 0.016	0.90 ± 0.009	0.98 ± 0.004	0.61 ± 0.003	0.88 ± 0.024	1.16 ± 0.052
Total cannabinoids	4.03	1.12	—	2.73	3.72	4.40	1.95	3.77	3.10	4.10	2.86	3.34	4.21

^aNd, not detected; Tr, traces.

^bHydroxycinnamic acid amides, lignanamides, and cannabinoids are expressed in mg caffeoyltyramine equivalent per g of extract (CTE per g extract).