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Table 1 in Bisabolane-type sesquiterpenoids: Structural diversity and biological activity
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- 1. ** & * & State Key Laboratory of Southwestern Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, China & ** & * & School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, China & ** & * & Institute of Innovative Medicine Ingredients of Southwest Specialty Medicinal Materials, Chengdu University of Traditional Chinese Medicine, Chengdu, 611137, China
Description
Table 1 Bisabolane-type sesquiterpenoids (compounds 1–108) from plants in the family Compositae. No. Name Molecular Weight Analytical methods Sources Reference (continued on next page)
| No. | Name | Molecular Weight | Analytical methods | Sources | Reference |
|---|---|---|---|---|---|
| 37 | Pararubin E | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 565.2617 | |||||
| 38 | Pararubin F | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 565.2619 | |||||
| 39 | Pararubin G | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 565.2618 | |||||
| 40 | Pararubin H | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 565.2617 | |||||
| 41 | Pararubin I | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 579.2761 | |||||
| 42 | Pararubin J | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 523.2514 | |||||
| 43 | Pararubin K | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 523.2499 | |||||
| 44 | Pararubin L | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 523.2514 | |||||
| 45 | Pararubin M | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 601.2983 | |||||
| 46 | Pararubin N | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 521.2356 | |||||
| 47 | Pararubin O | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 521.2353 | |||||
| 48 | Pararubin P | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 643.3090 | |||||
| 49 | Pararubin Q | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 629.2935 | |||||
| 65 | Pararubin R | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 643.3070 | |||||
| 51 | Pararubin S | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 589.2619 | |||||
| 52 | Pararubin T | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 589.2622 | |||||
| 53 | Pararubin U | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 507.2201 | |||||
| 54 | Pararubin V | [M + Na] + | NMR, IR, OR, UV, HRESIMS | P. rubescens | Jin et al. (2015) |
| 489.2094 | |||||
| 55 | 3,6-Epidioxy-1,10-bisaboladiene | [M + H] + | NMR, HRESIMS | P. delphiniifolius | Imamura et al. (2014), |
| 237.1850 | Kimura et al. (2012), | ||||
| Nishikawa et al. (2008) | |||||
| Tussilago | |||||
| 56 | Tussfararin A | [M] + 448.2096 | NMR, IR, OR, UV, HREIMS | T. farfara | Qin et al. (2014) |
| 57 | 1 α -(3-Ethyl- cis -crotonoyloxy)-8-angeloyloxy-3 β,4 β - | T. farfara | Qin et al. (2014) | ||
| epoxybisabola-7(14),10-dien-2-one | |||||
| 58 | 1 α,8-Bisangeloyloxy-3 β,4 β -epoxybisabola-7(14),10-dien-2-one | T. farfara | Qin et al. (2014) | ||
| 59 | (1 R,3 R,4 R,5 S,6 S)-1-Acetoxy-8-angeloyloxy-3,4-epoxy-5- | [M] + 406.1964 | NMR, IR, OR, UV, CD, HRMS | T. farfara | Jang et al. (2016), |
| hydroxybisabola-7(14),10-dien-2-one | Qin et al. (2014), | ||||
| Yaoita et al. (2001) | |||||
| 60 | (1 R,3 R,4 R,5 S,6 S)-1,5-Diacetoxy-8-angeloyloxy-3,4- | T. farfara | Jang et al. (2016), | ||
| epoxybisabola-7(14),10-dien-2-one | Qin et al. (2014) | ||||
| 61 | (3 R,4 R,6 S)-3,4-Epoxybisabola-7(14),10-dien-2-one | [M] + 234.1646 | NMR, IR, OR, UV, CD, HRMS | T. farfara | Yaoita et al. (2001) |
| 62 | 8-Angeloylxy-3,4-epoxy-bisabola-7(14),10-dien-2-one | [M + Na] + | NMR, OR, HRFABMS | T. farfara | Park et al. (2008) |
| 332.4346 | |||||
| 63 | Tussfararin B | [M] + 446.2308 | NMR, IR, OR, UV, HREIMS | T. farfara | Qin et al. (2014) |
| 64 | Tussfararin C | [M] + 446.2307 | NMR, IR, OR, UV, HREIMS | T. farfara | Qin et al. (2014) |
| 65 | Tussfararin D | [M] + 466.2119 | NMR, IR, OR, UV, HREIMS | T. farfara | Qin et al. (2014) |
| 66 | Tussfararin E | [M] + 444.2523 | NMR, IR, OR, UV, CD, HREIMS | T. farfara | Qin et al. (2014) |
| 67 | Tussfararin F | [M] + 430.2361 | NMR, IR, OR, UV, CD, HREIMS | T. farfara | Qin et al. (2014) |
| 68 | (4 R,6 E)-2-Acetoxy-8-angeloyloxy-4-hydroxybisabola-2,6,10- | T. farfara | Qin et al. (2014) | ||
| trien-1-one | |||||
| 69 | ()-Cryptomerion | T. farfara | Qin et al. (2014), | ||
| Yaoita et al. (2001) | |||||
| Carthamus | |||||
| 70 | O -3 ʹ -Senecioyl α -bisabolol β -D- fucopyranoside | [M + Na] + | NMR, OR, HRESIMS | C. glaucus | Taglialatela-Scafati et al. |
| 473.2872 | (2012) | ||||
| 71 | O -3 ʹ -(2,3-Dehydro- β -methyl)valeroyl- α -bisabolol β -D- | [M + Na] + | NMR, OR, HRESIMS | C. glaucus | Taglialatela-Scafati et al. |
| fucopyranoside | 487.3031 | (2012) | |||
| 72 | O -3 ʹ -Isovaleroyl α -bisabolol β -D- fucopyranoside | [M + Na] + | NMR, OR, HRESIMS | C. glaucus | Taglialatela-Scafati et al. |
| 475.3040 | (2012) | ||||
| 73 | O -3 ʹ -(β -Methyl)valeroyl- α -bisabolol β -D- fucopyranoside | [M + Na] + | NMR, OR, HRESIMS | C. glaucus | Taglialatela-Scafati et al. |
| 489.3201 | (2012) | ||||
| 74 | α -Bisabolol β -D- fucopyranoside | C. glaucus | Taglialatela-Scafati et al. | ||
| C. lanatus | (2012), | ||||
| Mikhova et al. (2004) | |||||
| 75 | α -Bisabolol | C. glaucus | Taglialatela-Scafati et al. | ||
| (2012) | |||||
| 76 | 10-Hydroperoxy-bisabola-2,11-diene 7- O -β - D- fucopyranoside | C. lanatus | Mikhova et al. (2004) | ||
Notes
Published as part of Shu, Hong-Zhen, Peng, Cheng, Bu, Lan, Guo, Li, Liu, Fei & Xiong, Liang, 2021, Bisabolane-type sesquiterpenoids: Structural diversity and biological activity, pp. 5 in Phytochemistry (112927) 192 on page 5, DOI: 10.1016/j.phytochem.2021.112927, http://zenodo.org/record/8258228
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References
- Jin, A., Wu, W. M., Yu, H. Y., Zhou, M., Liu, Y., Tian, T., Ruan, H. L., 2015. Bisabolane-Type sesquiterpenoids from the whole plant of Parasenecio rubescens. J. Nat. Prod. 78 (8), 2057 - 2066. https: // doi. org / 10.1021 / acs. jnatprod. 5 b 00380.
- Imamura, Y., Yukawa, M., Ueno, M., Kimura, K., Tsuchiya, E., 2014. 3,6 - Epidioxy- 1,10 - bisaboladiene inhibits G 1 - specific transcription through Swi 4 / Swi 6 and Mbp 1 / Swi 6 via the Hog 1 stress pathway in yeast. FEBS J. 281 (20), 4612 - 4621. https: // doi. org / 10.1111 / febs. 12965.
- Kimura, K., Sakamoto, Y., Fujisawa, N., Uesugi, S., Aburai, N., Kawada, M., Ohba, S., Yamori, T., Tsuchiya, E., Koshino, H., 2012. Cleavage mechanism and anti-tumor activity of 3,6 - epidioxy- 1,10 - bisaboladiene isolated from edible wild plants. Bioorg. Med. Chem. 20 (12), 3887 - 3897. https: // doi. org / 10.1016 / j. bmc. 2012.04.025.
- Nishikawa, K., Aburai, N., Yamada, K., Koshino, H., Tsuchiya, E., Kimura, K., 2008. The bisabolane sesquiterpenoid endoperoxide, 3,6 - epidioxy- 1,10 - bisaboladiene, isolated from Cacalia delphiniifolia inhibits the growth of human cancer cells and induces apoptosis. Biosci. Biotechnol. Biochem. 72 (9), 2463 - 2466. https: // doi. org / 10.1271 / bbb. 80266.
- Qin, Z. B., Zhang, J., Wu, X. D., He, J., Ding, L. F., Peng, L. Y., Li, X. Y., Li, Y., Deng, L., Guo, Y. D., Zhao, Q. S., 2014. Sesquiterpenoids from Tussilago farfara and their inhibitory effects on nitric oxide production. Planta Med. 80 (8 - 9), 703 - 709. https: // doi. org / 10.1055 / s- 0034 - 1368567.
- Jang, H., Lee, J. W., Lee, C., Jin, Q., Choi, J. Y., Lee, D., Han, S. B., Kim, Y., Hong, J. T., Lee, M. K., Hwang, B. Y., 2016. Sesquiterpenoids from Tussilago farfara inhibit LPSinduced nitric oxide production in macrophage RAW 264.7 cells. Arch Pharm. Res. (Seoul) 39 (1), 127 - 132. https: // doi. org / 10.1007 / s 12272 - 015 - 0667 - 7.
- Yaoita, Y., Suzuki, N., Kikuchi, M., 2001. Structures of new sesquiterpenoids from Farfarae flos. Chem. Pharm. Bull. (Tokyo) 49 (5), 645 - 648. https: // doi. org / 10.1248 / cpb. 49.645.
- Park, H. R., Yoo, M. Y., Seo, J. H., Kim, I. S., Kim, N. Y., Kang, J. Y., Cui, L., Lee, C. S., Lee, C. H., Lee, H. S., 2008. Sesquiterpenoids isolated from the flower buds of Tussilago farfara L. inhibit diacylglycerol acyltransferase. J. Agric. Food Chem. 56 (22), 10493 - 10497. https: // doi. org / 10.1021 / jf 801978 r.
- Mikhova, B., Duddeck, H., Taskova, R., Mitova, M., Alipieva, K., 2004. Oxygenated bisabolane fucosides from Carthamus lanatus L. Z. Naturforsch. C. J. Biosci. 59 (3 - 4), 244 - 248. https: // doi. org / 10.1515 / znc- 2004 - 3 - 422.
- Taglialatela-Scafati, O., Pollastro, F., Cicione, L., Chianese, G., Bellido, M. L., Munoz, E., Ozen ¨, H. C., Toker, Z., Appendino, G., 2012. STAT- 3 inhibitory bisabolanes from Carthamus glaucus. J. Nat. Prod. 75 (3), 453 - 458. https: // doi. org / 10.1021 / np 2008973.