A simple method for distinguishing <i>Dendrobium devonianum</i> and <i>Dendrobium officinale</i> by ultra performance liquid chromatography-photo diode array detector

LIN, Tao; CHEN, Xing-Lian; WU, Guang-Wei; SHA, Ling-Jie; WANG, Jing; HU, Zheng-Xu; LIU, Hong-Cheng

doi:10.1590/fst.110122

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Original Article • Food Sci. Technol 43 • 2023 • https://doi.org/10.1590/fst.110122 copy

A simple method for distinguishing Dendrobium devonianum and Dendrobium officinale by ultra performance liquid chromatography-photo diode array detector

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Using UPLC and PDA detector, the fingerprints of Dendrobium devonianum and Dendrobium officinale produced in the Longling area of Yunnan Province, China were obtained quickly and efficiently, and 26 common peaks in Dendrobium devonianum and Dendrobium officinale samples were obtained by automatic peak matching through the “Chinese Medicine Chromatographic Fingerprint Similarity Evaluation System”. The relative peak areas of the common peaks were analyzed by PCA using R, and the results showed that Dendrobium devonianum and Dendrobium officinale could be well distinguished by PCA, which was consistent with the analysis results of OPLS-DA. The results fully demonstrate that Dendrobium devonianum and Dendrobium officinale grown in the same area can be effectively distinguished by using the method of common peaks combined with stoichiometry. The VIP value of the 13 common peaks is greater than 1.0, which has a significant contribution to the difference and it was differential marker in Dendrobium devonianum and Dendrobium officinale. At the same time, normal-phase silica gel column chromatography was used to separate and purify the compounds that are related to the common peaks, and a total of 7 compounds were identified, among which eupatolide and isoschaftoside belong to differential markers and characteristic compounds in Dendrobium devonianum and Dendrobium officinale, which have good biological health care activity. The successful identification of Dendrobium devonianum and Dendrobium officinale in Longling area of Yunnan Province and the discovery of related differential markers play an important role in the further research and development of Dendrobium devonianum as a new food raw material and its products.

Keywords:
distinguishing; Dendrobium devonianum; Dendrobium officinale; ultra performance liquid chromatography; PCA; OPLS-DA

Ranking of VIP Value	Common peaks	Retention time (min)
1	S18	28.812
2	S4	9.877
3	S5	10.149
4	S20	30.408
5	S25	32.440
6	S21	30.773
7	S22	30.938
8	S17	28.320
9	S23	31.673
10	S7	10.576
11	S8	11.350
12	S14	15.790
13	S6	10.400
14	S3	9.636
15	S11	14.233
16	S9	11.955
17	S19	29.820
18	S1	8.898
19	S16	21.664
20	S15	16.256
21	S13	15.532
22	S24	31.842
23	S2	9.100
24	S26	32.766
25	S12	14.996
26	S10	13.408

Compound and Structure	NMR	VIP Value	Peak number (retention time/min)	References
Eupatolide	¹H-NMR (CDCl₃, 500 MHz) δ: 1.55 (3H, br s, H-15a), 1.57 (3H, br s, H-4), 2.07 (1H, m, H-2b), 2.05 (1H, m, H-3a), 2.18 (1H, br d, 12.6, H-8b), 2.25 (1H, m, H-3b), 2.27 (1H, m, H-2a), 2.48 (1H, dd, 12.5, 4.0, H-9a), 2.85 (1H, dd, 7.8, 4.0, H-7), 4.47 (1H, m, H-8), 4.74 (1H, dd, 11.0, 1.7, H-1a), 4.76 (1H, d, 9.5, H-5a), 5.11 (1H, dd, 7.8, 4.0, H-6), 6.13 (1H, d, 3.0, H-13a), 5.62 (H, d, 3.0, H-13b). ¹³C-NMR (CDCl₃, 125 MHz) δ: 136.0 (C-1), 25.6 (C-2), 38.7 (C-3), 140.4 (C-4), 128.0 (C-5), 74.8 (C-6), 52.7 (C-7), 70.3 (C-8), 47.1 (C-9), 127.7 (C-10), 138.8 (C-11), 169.9 (C-12), 120.1 (C-13), 16.8 (C-14), 19.5 (C-15)	1.0 VIP Value < 1.5	S7 (10.576)	Lee et al. (1972)Lee, K.-H., Furukawa, H., Huang, H.-C., & Huang, E.-S. (1972). Antitumor agents II: eupatolide, a new cytotoxic principle from Eupatorium formosanum HAY. Journal of Pharmaceutical Sciences, 61(4), 629-631. http://dx.doi.org/10.1002/jps.2600610432. PMid:4335375. http://dx.doi.org/10.1002/jps.2600610432... , Zhou et al. (1994)Zhou, B.-N., Bai, N.-S., Lin, L.-Z., & Cordell, G. A. (1994). Sesquiterpene lactones from Inula salsoloides. Phytochemistry, 36(3), 721-724. http://dx.doi.org/10.1016/S0031-9422(00)89804-0. http://dx.doi.org/10.1016/S0031-9422(00)...
Isoschaftoside	¹H-NMR (DMSO-d₆, 500 MHz) δ: 6.69 (1H, br s, H-3), 6.72 (2H, d, J=8.7 Hz, H-3’, 5’), 7.99 (2H, d, J=8.4 Hz, H-2’, 6’), 13.67 (1H, br s, OH-5); 6-C-α-Ara: 3.44 (1H, m, H-3”), 3.78 (1H, m, H-4”), 3.81, 3.59 (2H, m, 5”-CH₂), 4.04 (1H, br m, H-2”), 4.64 (1H, d, J=9.4 Hz, H-1”); 8-C-β-Glc: 3.28 (1H, m, H-5”’), 3.32 (1H, m, H-3”’), 3.37 (1H, m, H-4”’), 3.75, 3.56 (2H, m, 6”’-CH₂), 3.92 (1H, m, H-2”’), 4.83 (1H, d, J=9.9 Hz, H-1”’). ¹³C-NMR (DMSO-d₆, 125 MHz) δ: 128.8 (C-2’, 6’), 115.9 (C-3’, 5’), 102.2 (C-3); 6-C-α-Ara: 74.1 (C-1”), 69.2 (C-2”), 74.1 (C-3”), 68.6 (C-4”), 69.9 (C-5”); 8-C-β-Glc: 73.9 (C-1”’), 71.2 (C-2”’), 78.9 (C-3”’), 70.5 (C-4”’), 81.7 (C-5”’), 61.2 (C-6”’)	1.0 VIP Value < 1.5	S8 (11.350)	Fernando et al. (2019)Fernando, W. I. T., Attanayake, A. M. K. C., Perera, H. K. I., Sivakanesan, R., Jayasinghe, L., Araya, H., & Fujimoto, Y. (2019). Isolation, identification and characterization of pancreatic lipase inhibitors from Trigonella foenum-graecum seeds. South African Journal of Botany, 121, 418-421. http://dx.doi.org/10.1016/j.sajb.2018.10.023. http://dx.doi.org/10.1016/j.sajb.2018.10... , Xie et al. (2003)Xie, C., Veitch, N. C., Houghton, P. J., & Simmonds, M. S. J. (2003). Flavone C-glycosides from Viola yedoensis MAKINO. Chemical & Pharmaceutical Bulletin, 51(10), 1204-1207. http://dx.doi.org/10.1248/cpb.51.1204. PMid:14519932. http://dx.doi.org/10.1248/cpb.51.1204...
(+)-Syringaresinol	¹H-NMR (CDCl₃, 500 MHz) δ: 3.05 (2H, br s, H-8, 8'), 3.87 (2H, m, H-9, 9'), 3.88 (12H, s, OMe), 4.27 (2H, m, H-9, 9”), 4.70 (2H, s, H-7, 7'), 5.49 (2H, s, OH), 6.55 (4H, s, H-2, 6, 2', 6'). ¹³C-NMR (CDCl₃, 125 MHz) δ: 147.6 (C-3, 5, 3', 5'), 134.6 (C-4, 4'), 132.6 (C-1, 1'), 103.2 (C-2, 6, 2', 6'), 86.7 (C-7, 7'), 72.3 (C-9, 9'), 56.8 (OMe), 54.8 (C-8, 8')	0.5 < VIP Value < 1.0	S11 (14.233)	Park et al. (2003)Park, J. A., Kim, H. J., Jin, C., Lee, K.-T., & Lee, Y. S. (2003). A new pterocarpan,(-)-maackiain sulfate, from the roots of Sophora subprostrata'. Archives of Pharmacal Research, 26(12), 1009-1013. http://dx.doi.org/10.1007/BF02994750. PMid:14723332. http://dx.doi.org/10.1007/BF02994750... , El-Hassan et al. (2003)El-Hassan, A., El-Sayed, M., Hamed, A. I., Rhee, I. K., Ahmed, A. A., Zeller, K. P., & Verpoorte, R. (2003). Bioactive constituents of Leptadenia arborea. Fitoterapia, 74(1-2), 184-187. http://dx.doi.org/10.1016/S0367-326X(02)00314-3. PMid:12628421. http://dx.doi.org/10.1016/S0367-326X(02)...
Rutin	¹H-NMR (MeOH-d₄, 500 MHz) δ: 1.15 (3H, d, J = 6.1 Hz, rha-H-6), 4.54 (1H, d, J = 1.5 Hz, rha-H-1), 5.13 (1H, d, J = 7.7 Hz, glc-H-1), 6.22 (1H, d, J = 2.2 Hz, H-6), 6.43 (1H, d, J = 2.2 Hz, H-8), 6.88 (H, d, J = 8.3 Hz, H- 5’), 7.64 (1H, dd, J = 8.6, 2.2 Hz, H-6’), 7.68 (1H, d, J = 2.5 Hz, H-2’). ¹³C-NMR (MeOH-d₄, 125 MHz) δ: 159.6 (C-2), 135.7 (s, C-3), 179.6 (s, C-4), 163.2 (s, C-5), 100.1 (d, C-6), 166.3 (s, C-7), 95.1 (d, C-8), 158.7 (s, C-9), 105.9 (s, C-10), 123.4 (s, C-1’), 116.3 (d, C-2’), 146.1 (s, C-3’), 150.2 (s, C-4’), 117.8 (d, C-5’), 123.8 (d, C-6’), 104.9 (d, glc-C-1), 76.0 (d, glc-C-2), 78.3 (d, glc-C-3), 71.6 (d, glc-C-4), 77.5 (d, glc-C-5), 68.9 (t, glc-C-6), 102.5 (d, rha-C-1), 72.4 (d, rha-C-2), 72.2 (d, rha-C-3), 74.2 (d, rha-C-4), 69.9 (d, rha-C-5), 18.1 (q, rha-C-6).	0.5 < VIP Value < 1.0	S9 (11.955)	Li et al. (2008)Li, Y.-L., Li, J., Wang, N.-L., & Yao, X.-S. (2008). Flavonoids and a new polyacetylene from Bidens parviflora Willd. Molecules, 13(8), 1931-1941. http://dx.doi.org/10.3390/molecules13081931. PMid:18794794. http://dx.doi.org/10.3390/molecules13081... , Meng et al. (2009)Meng, L., Liu, R., Sun, A., Wu, S., & Liu, N. (2009). Separation and purification of rutin and acaciin from the Chinese medicinal herb Herba cirsii by combination of macroporous absorption resin and high-speed counter-current chromatography. Journal of Chromatographic Science, 47(5), 329-332. http://dx.doi.org/10.1093/chromsci/47.5.329. PMid:19476696. http://dx.doi.org/10.1093/chromsci/47.5....
Naringenin	¹H-NMR (DMSO-d₆, 500 MHz) δ: 2.71 (1H, dd, J=2.5, 16.0 Hz, H-3a), 3.15 (1H, dd, J=13.3, 16.0 Hz, H-3b), 5.43 (1H, dd, J=2.5, 13.3 Hz, H-2), 5.98 (2H, s, H-6, 8), 6.88 (2H, d, J=8.0 Hz, H-3’, 5’), 7.37 (2H, d, J=8.0 Hz, H-2’, 6’), 12.18 (1H, s, OH-5). ¹³C-NMR (DMSO-d₆, 125 MHz) δ: 41.84 (C-3), 78.35 (C-2), 94.30 (C-8), 95.25 (C-6), 101.64 (C-10), 114.65 (C-3’, C-5’), 127.50 (C-2’, C-6’), 129.24 (C-1’), 157.18 (C-4’), 162.90 (C-9), 163.82 (C-5), 165.83 (C-7), 195.82 (C-4)	0.5 < VIP Value < 1.0	S13 (10.400)	Jeon et al. (2008)Jeon, S. H., Chun, W., Choi, Y. J., & Kwon, Y. S. (2008). Cytotoxic constituents from the bark of Salix hulteni. Archives of Pharmacal Research, 31(8), 978-982. http://dx.doi.org/10.1007/s12272-001-1255-9. PMid:18787784. http://dx.doi.org/10.1007/s12272-001-125... , Singh et al. (2018)Singh, A. K., Raj, V., Keshari, A. K., Rai, A., Kumar, P., Rawat, A., Maity, B., Kumar, D., Prakash, A., De, A., Samanta, A., Bhattacharya, B., & Saha, S. (2018). Isolated mangiferin and naringenin exert antidiabetic effect via PPARγ/GLUT4 dual agonistic action with strong metabolic regulation. Chemico-Biological Interactions, 280, 33-44. http://dx.doi.org/10.1016/j.cbi.2017.12.007. PMid:29223569. http://dx.doi.org/10.1016/j.cbi.2017.12....
Vicenin II	¹H-NMR (DMSO-d₆, 500 MHz) δ: 6.43 (1H, s, H-3), 6.86 (2H, d, J=8.8 Hz, H-3’, 5’), 7.92 (2H, d, J=8.8 Hz, H-2’, 6’), 13.69 (1H, s, OH-5); 6-C-β-Glc: 3.17 (1H, m, H-5”), 3.22 (2H, m, H-3”, 4”), 3.64, 3.49 (2H, m, 6”-CH₂), 4.07 (1H, m, H-2”), 4.63 (1H, d, J=9.8 Hz, H-1”); 8-C-β-Glc: 3.29 (1H, m, H-3”’), 3.34 (1H, m, H-4”’), 3.26 (1H, m, H-5”’), 3.74, 3.53 (2H, m, 6”’-CH₂), 3.86 (1H, m, H-2”’), 4.83 (1H, d, J=9.8 Hz, H-1”’). ¹³C-NMR (DMSO-d₆, 125 MHz) δ: 127.8 (C-2’, 6’), 115.3 (C-3’, 5’), 101.0 (C-3); 6-C-β-Glc: 74.2 (C-1”), 70.6 (C-2”), 78.6 (C-3”’), 70.3 (C-4”’), 80.4 (C-5”), 60.9 (C-6”); 8-C-β-Glc: 74.3 (C-1”’), 71.6 (C-2”’), 78.9 (C-3”’), 70.6 (C-4”’), 81.2 (C-5”’), 61.2 (C-6”’)	0.5 < VIP Value < 1.0	S2 (9.100)	Xie et al. (2003)Xie, C., Veitch, N. C., Houghton, P. J., & Simmonds, M. S. J. (2003). Flavone C-glycosides from Viola yedoensis MAKINO. Chemical & Pharmaceutical Bulletin, 51(10), 1204-1207. http://dx.doi.org/10.1248/cpb.51.1204. PMid:14519932. http://dx.doi.org/10.1248/cpb.51.1204... , Siciliano et al. (2004)Siciliano, T., Tommasi, N., Morelli, I., & Braca, A. (2004). Study of flavonoids of Sechium edule (Jacq) Swartz (Cucurbitaceae) different edible organs by liquid chromatography photodiode array mass spectrometry. Journal of Agricultural and Food Chemistry, 52(21), 6510-6515. http://dx.doi.org/10.1021/jf040214q. PMid:15479015. http://dx.doi.org/10.1021/jf040214q...
Dendrophenol	¹H-NMR (CDCl₃, 500 MHz) δ: 2.73 (2H, m, H-7’), 2.77 (2H, m, H-7), 3.69 (3H, s, 3′-OCH₃), 3.77 (3H, s, 5-OCH₃), 6.18 (1H, t, J=2.2 Hz, H-4), 6.20 (1H, t, J=2.0 Hz, H-2), 6.22 (1H, t, J=1.6 Hz, H-6), 6.59 (1H, dd, J=8.0, 1.9 Hz, H-6’), 6.65 (1H, d, J=1.9 Hz, H-2’), 6.68 d (1H, d, J=8.0 Hz, H-5’). ¹³C-NMR (CDCl₃, 125 MHz) δ: 38.5 (C-7′), 121.9 (C-6′), 116.0 (C-5′), 145.6 (C-4′), 56.3 (3′-OCH₃), 148.7 (C-3′), 113.4 (C-2′), 134.8 (C-1′), 39.6 (C-7), 106.7 (C-6), 55.6 (5-OCH₃), 162.2 (C-5), 99.9 (C-4), 159.4 (C-3), 109.2 (C-2), 145.6 (C-1)	VIP Value < 0.5	S26 (32.766)	Leong et al. (1997)Leong, Y.-W., Kang, C.-C., Harrison, L. J., & Powell, A. D. (1997). Phenanthrenes, dihydrophenanthrenes and bibenzyls from the orchid bulbophyllum vaginatum. Phytochemistry, 44(1), 157-165. http://dx.doi.org/10.1016/S0031-9422(96)00387-1. http://dx.doi.org/10.1016/S0031-9422(96)... , Shimizu et al. (1988)Shimizu, M., Shogawa, H., Hayashi, T., Arisawa, M., Suzuki, S., Yoshizaki, M., Morita, N., Ferro, E., Basualdo, I., & Berganza, L. H. (1988). Anti-inflammatory constituents of topically applied crude drugs. III. Constituents and anti-inflammatory effect of Paraguayan crude drug “Tamandá cuná”(Catasetum barbatum LINDLE). Chemical & Pharmaceutical Bulletin, 36(11), 4447-4452. http://dx.doi.org/10.1248/cpb.36.4447. PMid:3246013. http://dx.doi.org/10.1248/cpb.36.4447...

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[1] *Corresponding author: lhc@yaas.org.cn