Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General Experimental Procedures
3.2. Plant Material
3.3. Extraction and Isolation
- Nitidaone A (1): white amorphous solid; −42.1° (c 0.5, MeOH); UV (MeOH) λmax (log ε) 256 (3.60), 272 (3.41) nm; 1H and 13C NMR data, see Table 1; HRESIMS m/z 343.1918 [M + H]+ (calcd. for C21H26O4, 343.1909).
- Nitidaone B (2): white amorphous solid; −53.9° (c 0.1, MeOH); UV (MeOH) λmax (log ε) 208 (3.79), 212 (3.82) nm; CD (MeOH) λmax (Δε) 208 (−0.05), 216 (0.08), 233 (−0.30), 339 (−0.04); 1H and 13C NMR data, see Table 1; HRESIMS m/z 345.2069 [M + H]+ (calcd. for C21H28O4, 345.2066).
- Nitidaol (3): white amorphous solid; −4.94° (c 0.2, MeOH); UV (MeOH) λmax (log ε) 257 (3.63), 281 (3.60) nm; 1H and 13C NMR data, see Table 2; HRESIMS m/z 343.1913 [M + H]+ (calcd. for C21H26O4, 343.1909).
3.4. Interleukin-6 Determination
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Not available. |
Nitidaone A (1) a | Nitidaone B (2) a | |||||
---|---|---|---|---|---|---|
Position | δC | Type | δH | δC | Type | δH (J in Hz) |
1 | 188.6 | C | 202.0 | C | ||
2 | 128.5 | CH | 6.29, dd (10.0, 1.9) | 129.3 | CH | 6.06, d (10.3) |
3 | 158.4 | CH | 7.19, dd (10.0, 3.0) | 159.8 | CH | 7.38, dd (10.3, 1.5) |
4 | 50.5 | C | 44.7 | C | ||
5 | 157.9 | CH | 7.10, dd (10.0, 3.0) | 36.3 | CH | 2.29–2.40, overlap; 2.14–2.24, overlap |
6 | 129.2 | CH | 6.32, dd (10.0,1.9) | 35.6 | CH | 2.29-2.40, overlap; 2.14–2.24, overlap |
7 | 43.2 | CH2 | 2.29, dd (13.9, 2.4); 1.95, dd (13.9, 7.6) | 46.7 | CH2 | 1.94, d (11.7); 1.61–1.67, overlap |
8 | 32.7 | CH | 1.45, m | 31.9 | CH | 1.62–1.68, overlap |
9 | 39.8 | CH | 1.77, m | 40.1 | CH | 1.63–1.69, overlap |
10 | 68.1 | CH2 | 4.03, dd (11.1, 6.9); 3.85, dd (11.1, 6.8) | 68.2 | CH2 | 3.90, dd (11.0, 6.6); 3.78, dd (11.0, 6.7) |
11 | 19.8 | CH3 | 0.93, d (7.0) | 19.2 | CH3 | 0.71, d (6.4) |
12 | 13.9 | CH3 | 0.89, d (7.0) | 13.7 | CH3 | 0.83, d (6.9) |
1′ | 133.4 | C | 137.0 | C | ||
2′, 6′ | 129.0 | CH | 7.28, d (9.0) | 129.3 | CH | 7.29, d (8.9) |
3′, 5′ | 115.5 | CH | 6.89, d (9.0) | 115.1 | CH | 6.90, d (8.9) |
4′ | 160.6 | C | 160.0 | C | ||
4′-OCH3 | 55.9 | CH3 | 3.76, s | 55.8 | CH3 | 3.78, s |
COCH3 | 21.0 | CH3 | 2.00, s | 21.0 | CH3 | 1.98, s |
OCO | 173.1 | C | 173.0 | C |
Nitidaol (3) a | |||
---|---|---|---|
Position | δC | Type | δH (J in Hz) |
1 | 156.4 | C | |
2 | 118.2 | CH | 6.58, d (2.7) |
3 | 144.5 | C | |
4 | 131.1 | C | |
5 | 132.6 | CH | 7.01, d (8.3) |
6 | 114.9 | CH | 6.67, dd (8.3, 2.7) |
7 | 36.8 | CH2 | 2.78 dd (13.6, 4.9) |
2.19, dd (13.6, 9.7) | |||
8 | 37.8 | CH | 1.47, m |
9 | 38.2 | CH | 1.55, m |
10 | 68.7 | CH2 | 3.66, m |
11 | 16.8 | CH3 | 0.65, d (6.9) |
12 | 14.1 | CH3 | 0.74, d (6.9) |
1′ | 136.0 | C | |
2′, 6′ | 131.4 | CH | 7.16, d (8.8) |
3′, 5′ | 114.7 | CH | 6.92, d (8.8) |
4′ | 160.2 | C | |
4′-OCH3 | 55.8 | CH3 | 3.82, s |
COCH3 | 21.0 | CH3 | 1.95, s |
OCO | 173.1 | C |
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Ahn, J.; Pei, Y.; Chae, H.-S.; Kim, S.-H.; Kim, Y.-M.; Choi, Y.H.; Lee, J.; Chang, M.; Song, Y.S.; Rodriguez, R.; et al. Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production. Molecules 2018, 23, 302. https://doi.org/10.3390/molecules23020302
Ahn J, Pei Y, Chae H-S, Kim S-H, Kim Y-M, Choi YH, Lee J, Chang M, Song YS, Rodriguez R, et al. Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production. Molecules. 2018; 23(2):302. https://doi.org/10.3390/molecules23020302
Chicago/Turabian StyleAhn, Jongmin, Yihua Pei, Hee-Sung Chae, Seong-Hwan Kim, Young-Mi Kim, Young Hee Choi, Joongku Lee, Minsun Chang, Yun Seon Song, Roberto Rodriguez, and et al. 2018. "Spiroketones and a Biphenyl Analog from Stems and Leaves of Larrea nitida and Their Inhibitory Activity against IL-6 Production" Molecules 23, no. 2: 302. https://doi.org/10.3390/molecules23020302