Lasianosides F–I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr.
Abstract
:1. Introduction
2. Results
2.1. Isolation and Spectroscopic Analyses of the Compounds
2.1.1. Chemical Structure of Compound 1
2.1.2. Chemical Structure of Compound 2
2.1.3. Chemical Structure of Compound 3
2.1.4. Chemical Structure of Compound 4
3. Materials and Methods
3.1. General Methods
3.2. Plant Material
3.3. Extraction and Isolation
3.4. Spectroscopic Data of Compounds 1–4
3.5. Acid Hydrolysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–8 are available from the authors. |
Position | δc | δH Multi (J in Hz) |
---|---|---|
1 | 93.3 | 5.98 d (1.0) |
3 | 150.4 | 7.32 d (2.0) |
4 | 106.2 | - |
5 | 37.5 | 3.70 t-like (6.8) |
6 | 86.4 | 5.59 br dt (6.5, 1.7) |
7 | 129.1 | 5.75 br t (1.8) |
8 | 144.4 | - |
9 | 45.4 | 3.31 m |
10 | 61.7 | 4.69 dd (14.4, 1.0) 4.81 dd (14.4, 1.0) |
11 | 172.6 | - |
1’ | 100.0 | 4.70 d (7.9) |
2’ | 74.7 | 3.22 dd (9.1, 7.9) |
3’ | 77.9 | 3.40 br t (8.9) |
4’ | 71.6 | 3.30 m |
5’ | 78.4 | 3.37 ddd (9.3, 6.0,2.1) |
6’ | 62.8 | 3.70 dd (11.8, 6.0) 3.94 dd (11.8, 2.1) |
1’’ | 174.2 | - |
2’’ | 44.0 | 2.28, 2H, d (7.2) |
3’’ | 26.8 | 2.09 nonet-like (6.8) |
4’’/5’’ | 22.8 | 0.98, 6H, d (6.6) |
Position | 2 | 3 | ||
---|---|---|---|---|
Unit A δH Multi (J in Hz) | Unit B δH Multi (J in Hz) | Unit A δH Multi (J in Hz) | Unit B δH Multi (J in Hz) | |
1 | 5.86 d (1.4) | 5.05 d (9.1) | 5.99 br s | 5.07 d (9.2) |
3 | 7.15 d (1.9) | 7.70 d (1.1) | 7.33 br d (1.7) | 7.77 br d (1.3) |
4 | - | - | - | - |
5 | 3.43 m | 2.86 ddd (7.1, 5.7, 1.1) | 3.69 m | 3.12 br t (6.8) |
6 | 5.51 br dt (6.6, 1.6) | 4.80 m | 5.59 br t (6.2) | 4.89 m |
7 | 5.69 br t (1.6) | 6.00 br d (1.7) | 5.76 br s | 6.05 br d (1.9) |
8 | - | - | - | - |
9 | 3.27 m | 2.73 t-like (8.5) | 3.36 m | 2.72 t-like (8.1) |
10 | 4.62 dd (14.6, 0.9) 4.74 m | 4.82 m 4.95 dd (14.8, 0.6) | 4.69 br d (14.4) 4.80 m | 4.82 m 4.97 br d (15.8) |
11 | - | - | - | - |
10-COCH3 | - | - | - | - |
10-COCH3 | 2.05 s | 2.09 s | 2.10 s | 2.10 s |
1’ | 4.92 d (8.2) | 4.70 d (7.8) | 4.84 m | 4.75 d (7.9) |
2’ | 4.80 m | 3.27 m | 3.44 dd (9.6, 8.1) | 3.27 t-like (8.3) |
3’ | 3.67 t-like (9.2) | 3.38 m | 5.08 t-like (8.6) | 3.30 m |
4’ | 3.38 m | 3.29 m | 3.59 t-like (9.4) | 3.28 m |
5’ | 3.45 m | 3.29 m | 3.51 ddd (9.8, 5.6, 1.9) | 3.40 br d (8.8) |
6’ | 3.69 dd (11.9, 6.7) 3.94 dd (11.9, 1.8) | 3.61 dd (12.0, 5.6) 3.83 dd (12.0, 1.4) | 3.74 m 3.95 dd (11.9, 1.9) | 3.63 dd (11.9, 5.8) 3.87 dd (11.9, 1.7) |
Position | 2 | 3 * | ||
---|---|---|---|---|
Unit A | Unit B | Unit A | Unit B | |
1 | 94.1 | 101.8 | 93.4 | 101.4 |
3 | 150.1 | 156.3 | 150.3 | 156.2 |
4 | 106.3 | 107.7 | 106.2 | 108.0 |
5 | 37.6 | 42.9 | 37.5 | 42.5 |
6 | 86.1 | 75.2 | 86.4 | 75.8 |
7 | 129.1 | 131.6 | 129.0 | 131.5 |
8 | 143.9 | 146.5 | 144.3 | 146.2 |
9 | 45.1 | 45.9 | 45.3 | 46.4 |
10 | 61.9 | 63.8 | 62.0 | 63.8 |
11 | 172.2 | 167.6 | 172.6 | 168.6 |
10-COCH3 | 172.7 | 172.2 | 172.4 | 172.6 |
10-COCH3 | 20.6 | 20.8 | 20.7 | 20.8 |
1’ | 98.7 | 100.9 | 100.0 | 100.6 |
2’ | 74.5 | 74.9 | 73.0 | 74.9 |
3’ | 75.6 | 77.8 | 78.7 | 77.9 |
4’ | 71.6 | 71.7 | 70.0 | 71.6 |
5’ | 78.5 | 78.6 | 78.6 | 78.6 |
6’ | 62.7 | 63.0 | 62.4 | 63.0 |
Position | Unit A | Unit B | ||
---|---|---|---|---|
δc | δH multi (J in Hz) | δc | δH multi (J in Hz) | |
1 | 93.5 | 5.91 d (1.1) | 97.0 | 5.14 d (6.0) |
3 | 150.3 | 7.33 d (1.9) | 97.4 | 5.27 d (3.6) |
4 | 106.3 | - | 44.4 | 3.36 m |
5 | 37.5 | 3.69 td-like (6.8, 1.8) | 37.5 | 3.47 m |
6 | 86.4 | 5.59 dt (6.6, 1.4) | 87.9 | 5.41 br d (6.5) |
7 | 128.9 | 5.75 br s | 125.9 | 6.01 br s |
8 | 144.3 | - | 152.5 | - |
9 | 45.5 | 3.37 m | 46.3 | 3.05 m |
10 | 61.9 | 4.68 br dd (14.3, 1.0) 4.79 dd (14.6, 1.2) | 62.8 | 4.68 dd-like (14.3, 1.0) 5.00 br d (15.9) |
11 | 172.6 | - | 176.9 | - |
10-COCH3 | 172.2 | - | 172.6 | - |
10-COCH3 | 20.8 | 2.13 s | 20.8 | 2.09 s |
1’ | 100.2 | 4.75 d (8.1) | 99.6 | 4.73 d (8.1) |
2’ | 74.5 | 3.24 dd (8.9, 8.1) | 75.0 | 3.24 dd (8.9, 8.1) |
3’ | 77.8 | 3.42 m | 77.9 | 3.43 m |
4’ | 71.2 | 3.42 m | 71.6 | 3.30 m |
5’ | 76.6 | 3.57 br dd (9.4, 3.6) | 78.4 | 3.32 m |
6’ | 68.1 | 3.95 dd (11.7, 1.4) 4.18 dd (11.7, 5.0) | 62.8 | 3.67 dd (11.7, 3.6) 3.88 br d (11.7) |
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Al-Hamoud, G.A.; Orfali, R.S.; Takeda, Y.; Sugimoto, S.; Yamano, Y.; Al Musayeib, N.M.; Fantoukh, O.I.; Amina, M.; Otsuka, H.; Matsunami, K. Lasianosides F–I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. Molecules 2020, 25, 2798. https://doi.org/10.3390/molecules25122798
Al-Hamoud GA, Orfali RS, Takeda Y, Sugimoto S, Yamano Y, Al Musayeib NM, Fantoukh OI, Amina M, Otsuka H, Matsunami K. Lasianosides F–I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. Molecules. 2020; 25(12):2798. https://doi.org/10.3390/molecules25122798
Chicago/Turabian StyleAl-Hamoud, Gadah Abdulaziz, Raha Saud Orfali, Yoshio Takeda, Sachiko Sugimoto, Yoshi Yamano, Nawal M. Al Musayeib, Omer Ibrahim Fantoukh, Musarat Amina, Hideaki Otsuka, and Katsuyoshi Matsunami. 2020. "Lasianosides F–I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr." Molecules 25, no. 12: 2798. https://doi.org/10.3390/molecules25122798
APA StyleAl-Hamoud, G. A., Orfali, R. S., Takeda, Y., Sugimoto, S., Yamano, Y., Al Musayeib, N. M., Fantoukh, O. I., Amina, M., Otsuka, H., & Matsunami, K. (2020). Lasianosides F–I: A New Iridoid and Three New Bis-Iridoid Glycosides from the Leaves of Lasianthus verticillatus (Lour.) Merr. Molecules, 25(12), 2798. https://doi.org/10.3390/molecules25122798