One new glucosidic iridoid, 6-O-veratroylbarlerin, was isolated from the chloroform/methanol extract of Isodon rubescens (Hemsl.) H.Hara, Lamiaceae aerial parts, along with the known compounds apigenin and caffeic acid. The structure of the new compound was elucidated on the basis of 1D and 2D NMR experiments and ESI-MS technique.
Keywords:
Rabdosia; Lamiaceae; Iridoid; NMR
| Position | 1 | |
|---|---|---|
| δ H | δ C | |
| 1 | 5.95 d (2.8) | 95.2 |
| 3 | 7.56 s | 153.4 |
| 4 | 107.0 | |
| 5 | 3.45 m | 39.7 |
| 6 | 5.52 br d (5.0) | 79.0 |
| 7a | 2.26 dd (14.0, 5.0) | 44.5 |
| 7b | 2.50 br d (14.0) | |
| 8 | 89.0 | |
| 9 | 3.11 dd (3.5, 8.5) | 50.2 |
| 10 | 1.62 s | 21.4 |
| 11 | 168.0 | |
| 12 | 3.69 s | 51.6 |
| Glc-1' | 4.71 d (8.0) | 100.1 |
| 2' | 3.23 dd (8.0, 9.0) | 74.2 |
| 3' | 3.37 t (9.0) | 78.0 |
| 4' | 3.30 t (9.0) | 71.3 |
| 5' | 3.39 m | 77.7 |
| 6' | 3.70 o | 62.8 |
| 3.54 dd (12.0, 3.5) | ||
| Vrt-7' | 167.0 | |
| 1" | 7.58 d (1.5) | 123.5 |
| 2" | 113.3 | |
| 3" | 7.09 d (8.3) | 149.9 |
| 4" | 7.70 dd (8.3, 1.5) | 154.6 |
| 5" | 3.93 s | 111.6 |
| 6" | 3.91 s | 124.9 |
| OCH3-3" | 56.2 | |
| OCH3-4" | 1.91 s | 56.0 |
| OCOCH3 | 172.3 | |
| OCOCH3 | 21.2 | |
| Plant species | Caffeic acid | Apigenin | Apigenin glycosides | References |
|---|---|---|---|---|
| I. eriocalyx var. laxiflora | + | Niu et al. (2003)Niu, X., Li, S., Na, Z., Mei, S., Zhao, Q., Sun, H., 2003. Studies on chemical constituents of Isodon eriocalyx var. laxiflora. Zhongcaoyao 34, 300-303. | ||
| I. japonicus | + | Hong et al. (2009)Hong, S.-S., Lee, C., Lee, C.-H., Park, M., Lee, M.-S., Hong, J.-T., Lee, H., Lee, M.-K., Hwang, B.-Y., 2009. A new furofuran lignan from Isodon japonicus. Arch. Pharm. Res. 32, 501-504. | ||
| I. lophanthoides | + | Feng et al. (2013)Feng, H.R., Zhu, D.Q., Huang, S., Lin, J., Lai, X.P., Chen, L.L., Lu, Q.F., 2013. Effects of different harvest times and different processing methods on contents of caffeic acid and rosmarinic acid in Isodon lophanthoides. Zhongguo Shiyan Fangjixue Zazhi 19, 71-73. | ||
| I. lophanthoides var. gerardianus | + | + | Tang et al. (2015)Tang, H.-M., Chen, J.-N., Zhang, Y., Lai, X.-P., Huang, S., 2015. Simultaneous determination of eight water-soluble compositions in Isodon serra from different origins by HPLC. Yaowu Fenxi Zazhi 35, 228-234.; Feng et al. (2016)Feng, C.P., Tang, H.M., Huang, S., Hou, S.Z., Liang, J., Huang, W., Lai, X.P., 2016. Evaluation of the effects of the water-soluble total flavonoids from Isodon lophanthoides var. gerardianus (Benth.) H.Hara on apoptosis in HepG2 cell: investigation of the most relevant mechanisms. J. Ethnopharmacol. 188, 70-79. | |
| I. lophathoides var. graciliflorus | + | + | Zhou et al. (2014)Zhou, W., Xie, H., Xu, X., Liang, Y., Wei, X., 2014. Phenolic constituents from Isodon lophanthoides var. graciliflorus and their antioxidant and antibacterial activities. J. Funct. Foods 6, 492-498.; Tang et al. (2015)Tang, H.-M., Chen, J.-N., Zhang, Y., Lai, X.-P., Huang, S., 2015. Simultaneous determination of eight water-soluble compositions in Isodon serra from different origins by HPLC. Yaowu Fenxi Zazhi 35, 228-234. | |
| I. nervosa | + | Du et al. (2010b)Du, Y., Jin, Y., Liu, P., Zhang, X., Sheng, X., Shi, X., Wang, Q., Zhang, L., 2010. Rapid method for simultaneous determination of 20 components in Isodon nervosa by HPLCaphy-electrospray ionization tandem mass spectrometry. Phytochem. Anal. 21, 416-427. | ||
| I. oresbius | + | Hao et al. (1996)Hao, H., Handong, S., Shouxun, Z., 1996. Flavonoids from Isodon oresbius. Phytochemistry 42, 1247-1248. | ||
| I. rubescens | + | Du et al. (2010a)Du, Y., Liu, P., Yuan, Z., Jin, Y., Zhang, X., Sheng, X., Shi, X., Wang, Q., Zhang, L., 2010. Simultaneous qualitative and quantitative analysis of 28 components in Isodon rubescens by HPLC-ESI-MS/MS. J. Sep. Sci. 33, 545-557. | ||
| I. sculponeata | + | Jiang et al. (2002)Jiang, B., Hou, A.-J., Li, M.-L., Li, S.-H., Han, Q.-B., Wang, S.-J., Lin, Z.-W., Sun, H.-D., 2002. Cytotoxic ent-kaurane diterpenoids from Isodon sculponeata. Planta Med. 68, 921-925. | ||
| I. serra | + | + | Liu et al. (2010)Liu, P., Du, Y., Zhang, X., Sheng, X., Shi, X., Zhao, C., Zhu, H., Wang, N., Wang, Q., Zhang, L., 2010. Rapid analysis of 27 components of Isodon serra by LC-ESI-MS-MS. Chromatographia 72, 265-273.; Tang et al. (2015)Tang, H.-M., Chen, J.-N., Zhang, Y., Lai, X.-P., Huang, S., 2015. Simultaneous determination of eight water-soluble compositions in Isodon serra from different origins by HPLC. Yaowu Fenxi Zazhi 35, 228-234. | |
| I. sorra | + | + | Chen et al. (2013)Chen, X.-D., Zhu, D.-Q., Zhang, G.-D., He, W.-J., Liu, F.-J., Wei, M., 2013. Determination of caffeic acid, vitexin and rosmarinic acid contents in Isodon sorra formula granule by HPLC. Zhongyaocai 36, 1530-1532.; Tang et al. (2015)Tang, H.-M., Chen, J.-N., Zhang, Y., Lai, X.-P., Huang, S., 2015. Simultaneous determination of eight water-soluble compositions in Isodon serra from different origins by HPLC. Yaowu Fenxi Zazhi 35, 228-234. | |
| I. striatus | + | + | Tang et al. (2015)Tang, H.-M., Chen, J.-N., Zhang, Y., Lai, X.-P., Huang, S., 2015. Simultaneous determination of eight water-soluble compositions in Isodon serra from different origins by HPLC. Yaowu Fenxi Zazhi 35, 228-234. | |
| I. ternifolius | + | Na et al. (2002)Na, Z., Xiang, W., Zhao, Q., Mei, S., Li, C., Lin, Z., Sun, H., 2002. New ent-kauranoid from Isodon ternifolius. Yunnan Zhiwu Yanjiu 24, 267-272. | ||
| I. xerophilus | + | Hou et al. (2011)Hou, A.-J., Yang, H., Liu, Y.-Z., Zhao, Q.-S., Lin, Z.-W., Sun, H.-D., 2011. Novel ent-kaurane diterpenoids from Isodon xerophilus. Chin. J. Chem. 19, 365-370. | ||
| R. excisa | + | Tang et al. (2014)Tang, J., Ma, R.-L., Liu, H.-C., Ouyang, Z., Chen, H.S., 2014. Tianran Chanwu Yanjiu Yu Kaifa 26, 215-217. | ||
| R. japonica | + | Shen et al. (2009)Shen, X., Wang, B., Liu, C., Zhang, J., 2009. Chemical composition of Rabdosia japonica. Zhongcaoyao 40, 1883-1885.; Liu et al. (2013)Liu, H.-C., Jin, Y.-S., Chen, H.-S., 2013. Study on triterpenoid and flavonoid contents of Rabdosia japonica. Dier Junyi Daxue Xuebao 34, 1121-1124. | ||
| R. japonica var. glaucocalyx | + | + | + | Zhang et al. (2006)Zhang, J., Wang, B., Zhang, N., 2006. Flavonoid components of Rabdosia japonica var. glaucocalyx (Maxin.) Hara. Zhongcaoyao 37, 1142-1144.; Yao et al. (2013)Yao, S., Xu, N.-Y., Chu, C.-J., Zhang, J., Chen, D.-F., 2013. Chemical constituents of Rabdosia japonica var. glaucocalyx and their anti-complement activity. Zhongguo Zhongyao Zazhi 8, 199-203. |
| R. lophanthoides | + | + | Kuang et al. (2014)Kuang, Y.-H., Lin, Q., Liang, S., Yao, X.-H., Wang, Z.-M., Li, C.-Y., 2014. Water-soluble chemical constituents from Rabsodia lophanthoides. Zhongguo Shiyan Fangjixue Zazhi 20, 110-112.; Lu (2015)Lu, Q., 2015. Study on the content dynamic changes of caffeic acid, vicenin-2 and isoschaftoside in Rabdosia lophanthoides. Zhongguo Yaofang 26, 4271-4273. | |
| R. lophanthoides var gerardiana | + | Lu et al. (2013)Lu, Q.-F., Tang, H.-M., Chen, L.-L., Feng, H.-R., Huang, S., 2013. Identification and determination of caffeic acid and rosmarinic acid in Rabdosia lophanthoides var gerardiana by TLC and HPLC. Zhongguo Shiyan Fangjixue Zazhi 19, 114-116. | ||
| R. rubescens | + | Tang et al. (2011)Tang, J., Zhao, M., Wang, Y., Kang, G., Wu, J., Zheng, M., Peng, S., 2011. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 879, 2783-2793.; Guo et al. (2017)Guo, S., Cui, X., Jiang, M., Bai, L., Tian, X., Guo, T., Liu, Q., Zhang, L., Ho, C.T., Bai, N., 2017. Simultaneous characterization and quantification of 17 main compounds in Rabdosia rubescens by high performance liquid chromatography. J. Food Drug Anal. 25, 417-424. | ||
| R. flexicaulis | + | Li et al. (2015)Li, L.-J., Yu, L.-J., Wu, Z.-Z., Liu, X., 2015. Chemical constituents in ethyl acetate extract from Rabdosia flexicaulis. Zhongcaoyao 46, 339-343. | ||
| R. serra | + | Zhu et al. (2013)Zhu, D.-Q., Huang, S., Chen, J.-N., Tan, Y.-L., Qu, Y.-Y., Zhuang, Y.-J., 2013. Determination of caffeic acid and rosmarinic acid in Rabdosia serra from different species and different habitats. Zhongguo Shiyan Fangjixue Zazhi 19, 114-117. |
