. 2015 Mar 6;7(3):1672–1687. doi: 10.3390/nu7031672

Table 3.

NMR data of the identified black rice bran sterols and triterpenoids

Compound	Selected ¹H-NMR Data δ (Multiplicity/Hz)	Selected ¹³C-NMR Data δ
Sterols
24-Methylene-ergosta-5-en-3β-ol	0.68 (s, H₁₈), 0.95 (d, 6.6, H₂₁), 1.00 (s, H₁₉), 1.02, 1.03 (d, 6.8, H₂₆, H₂₇), 3.52 (m, H₃), 4.65 (s, H₂₈), 4.71 (s, H₂₈), 5.35 (d, 4.9, H₆)	11.86 (C₁₈), 18.71 (C₂₁), 19.40 (C₁₉), 21.87, 22.00 (C₂₆, C₂₇), 71.82 (C₃), 105.93 (C₂₈), 121.72 (C₆), 140.77 (C₅)
24-Methylene-ergosta-7-en-3β-ol	0.54 (s, H₁₈), 0.80 (s, H₁₉), 0.94 (d, 6.6, H₂₁), 1.02, 1.03 (d, 6.8, H₂₆, H₂₇), 3.62 (m, H₃), 4.65 (s, H₂₈), 4.71 (s, H₂₈), 5.15 (d, 2.3, H₇)	11.86 (C₁₈), 13.04 (C₁₉), 18.84 (C₂₁), 21.87, 22.00 (C₂₆, C₂₇), 71.08 (C₃), 105.93 (C₂₈), 120.00 (C₇), 139.57 (C₈)
Fucosterol	0.68 (s, H₁₈), 0.98 (d, 6.4, H₂₁), 1.01, 1.02 (d, 6.8, H₂₆, H₂₇), 1.00 (s, H₁₉), 1.57(d, 7.2, H₂₉), 3.53 (m, H₃), 5.18 (q, 6.7, H₂₈), 5.35 (d, 5.2, H₆).	11.85 (C₁₈), 13.05 (C₂₉), 18.81 (C₂₁), 19.40 (C₁₉), 21.87 (C₂₇), 22.01 (C₂₆), 71.82 (C₃), 116.46 (C₂₈), 121.72 (C₆), 140.77 (C₅), 146.80 (C₂₄).
Gramisterol	0.54 (s, H₁₈), 0.79 (s, H₁₉), 0.89 (d, 6.5, H₂₁), 0.95 (d, 6.4, H₂₉), 1.01, 1.02 (d, 6.8, H₂₆, H₂₇), 3.11 (dt, 4.3, 10.9, H₃), 4.65 (s, H₂₈), 4.71 (s, H₂₈), 5.12 (d, 3.9, H₇).	11.85 (C₁₈), 14.14 (C₁₉), 15.15 (C₂₉), 18.84 (C₂₁), 21.37 (C₁₁), 21.87 (C₂₇), 22.01 (C₂₆), 76.23 (C₃), 105.95 (C₂₈), 117.51 (C₇), 139.10 (C₈), 156.87 (C₂₄).
Campesterol	0.67 (s, H₁₈), 0.77 (d, 6.6, H₂₈), 0.79 (d, 6.8, H₂₇), 0.84 (d, 6.8, H₂₆), 0.90 (d, 6.6, H₂₁), 1.00 (s, H₁₉), 3.51 (m, H₃), 5.33 (d, 5.2, H₆).	11.87 (C₁₈), 15.38 (C₂₈), 18.26 (C₂₇), 18.71 (C₂₁), 19.40 (C₁₉), 20.21 (C₂₆), 71.81 (C₃), 121.72 (C₆), 140.77 (C₅).
Stigmasterol	0.69 (s, H₁₈), 0.76 (d, 7.8, H₂₉), 0.80 (d, 6.8, H₂₇), 0.85 (d, 6.8, H₂₆), 1.00 (s, H₁₉), 1.01 (d, 6.6, H₂₁), 3.51 (m, H₃), 5.00, 5.15 (dd, 8.6, 5.2, H₂₂, H₂₃), 5.33 (d, 5.2, H₆).	12.05 (C₁₈), 12.25 (C₂₇), 15.15 (C₂₉), 18.90 (C₂₁), 19.40 (C₁₉), 20.52(C₂₆), 71.81 (C₃), 121.72 (C₆), 129.29, 138.32 (C₂₂, C₂₃), 140.77 (C₅).
β-Sitosterol	0.67 (s, H₁₈), 0.80, 0.82 (d, 6.8, H₂₆, H₂₇), 0.84 (d, 7.8, H₂₉), 0.92 (d, 6.6, H₂₁), 1.00 (s, H₁₉), 3.52 (m, H₃), 5.35 (d, 5.2, H₆).	11.87 (C₁₈), 11.99 (C₂₉), 18.79 (C₂₁), 19.05, 19.83 (C₂₆, C₂₇), 19.41 (C₁₉), 70.79 (C₃), 121.72 (C₆), 140.77 (C₅).
Triterpenoids
Cycloeucalenol	0.15 (d, H₁₉), 0.38 (d, H₁₉), 3.20 (m, H₃), 4.64 (s, H₂₈), 4.73 (s, H₂₈).	ND (minor compound)
Lupenone	4.57 (m, H₂₉), 4.68 (d, 2.2, H₂₉)	ND (minor compound)
Lupeol	3.20 (m, H₃), 4.57 (m, H₂₉), 4.68 (d, 2.2, H₂₉)	ND (minor compound)
24-Methylenecycloartanol	0.33 (d, 4.2, H₁₉), 0.55 (d, 4.2, H₁₉), 0.81 (s, H₁₈), 0.89 (d, 4.3, H₂₁), 0.90 (s, H₂₉), 0.97 (s, H₃₀, H₃₁), 1.02 (d, 2.2, H₂₆), 1.04 (d, 2.2, H₂₇), 3.28 (dd, 4.3, 11.1, H₃), 4.66 (s, H₂₈), 4.71 (s, H₂₈).	14.15, 18.04, 18.32, 19.33, 21.88, 22.01, 25.24 (7Me), 29.72 (C₁₉), 78.85 (C₃), 105.94 (C₂₈), 156.92 (C₂₄).