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Article

Phytoecdysteroids from the Roots of Achyranthes bidentata Blume

by
Mei Zhang
1,2,
Zhong-Yu Zhou
1,
Jing Wang
1,2,
Yong Cao
3,
Xue-Xiang Chen
3,
Wei-Min Zhang
4,
Li-Dong Lin
1 and
Jian-Wen Tan
1,*
1
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China
2
Graduate School of the Chinese Academy of Sciences, Beijing 100039, China
3
College of Food Science, South China Agricultural University, Guangzhou 510642, China
4
Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Institute of Microbiology, Guangzhou 510070, China
*
Author to whom correspondence should be addressed.
Molecules 2012, 17(3), 3324-3332; https://doi.org/10.3390/molecules17033324
Submission received: 23 February 2012 / Revised: 8 March 2012 / Accepted: 12 March 2012 / Published: 14 March 2012
Browse Figures
Versions Notes

Abstract

:
Two new phytoecdysteroids, (25S)-20,22-O-(R-ethylidene)inokosterone (1) and 20,22-O-(R-3-methoxycarbonyl)propylidene-20-hydroxyecdysone (2), together with six known phytoecdysteroids 3–8 were isolated from the roots of Achyranthes bidentata Blume. The new structures were established on the basis of spectroscopic studies and chemical evidences. The absolute configuration at C-25 in the structure of known compound 3 was determined by chemical and spectroscopic means.

1. Introduction

Achyranthes bidentata Blume (Amaranthaceae) is widely distributed in Asian countries like India, Korea, Japan, and China. The root of A. bidentata has been prescribed in the Chinese Pharmacopeia as an important herbal medicine and its multiple pharmacological effects, such as anti-osteoporosis [1,2], antitumor [3,4,5], anti-senility [3,6,7,8], anti-inflammatory [9], immunomodulatory [3,10,11,12,13] activities are well documented. Previous phytochemical investigations of A. bidentata have reported the isolation of phytoecdysteroids [14,15,16], saccharides [17,18] and saponins [19,20], and some of them displayed diverse bioactivities. In the course of our search for potentially new and bioactive compounds from medicinal plants in China, we investigated the roots of A. bidentata and isolated eight phytoecdysteroids, including two new ones, (25S)-20,22-O-(R-ethylidene)inokosterone (1) and 20,22-O-(R-3-methoxycarbonyl)propylidene-20-hydroxyecdysone (2), and six known phytoecdysteroids 3–8 (Figure 1). In this paper, we report the isolation and structural elucidation of these phytoecdysteroids.
Molecules 17 03324 g001 550
Figure 1. Chemical structures of compounds 1–8.
Figure 1. Chemical structures of compounds 1–8.
Molecules 17 03324 g001

2. Results and Discussion

Compound 1 was obtained as a white amorphous powder with a molecular formula of C29H46O7 as established on the basis of a combined analysis of its HRESIMS and NMR spectroscopic data. The spectroscopic data (IR, UV, and NMR: see Section 3.3. and Table 1 and Table 2) supported the fact that 1 was an ecdysteroid closely related to inokosterone-20,22-acetonide, a reported [21,22] ecdysteroid compound which was also obtained as compound 3 in the present study. Careful analysis of the 1H- and 13C-NMR spectra pointed out as major differences that the resonances for the acetone ketal group in 3 were replaced by the signals for a C2 acetal group [δH 5.05 (1H, q, H-1'), 1.29 (3H, d, H3-2'); δC 102.3 (C-1'), 22.0 (C-2')]. These data led us to preliminarily establish the whole structure of 1 as 20,22-ethylideneinokosterone, of which the stereochemistry at C-25 and C-1' still needed to be determined. In the 1H-1H COSY spectrum, signals correlated to the connections of C-22 to C-27 were exhibited. In the NOESY spectrum, a significant correlation signal of H-1' (δH 5.05) with H-22 (δH 3.65) was observed, which indicated that the stereochemistry at C-1' in 1 should be R configuration (Figure 2). In order to clarify the absolute configuration at C-25 in the molecule, an acid hydrolysis of 1 was carried out, and the centre ecdysteroid unit that released from 1 was confirmed to be the same as the known compound (25S)-inokosterone (8), as evidenced by a co-TLC elution test and comparison of the NMR spectroscopic data with literature precedents [23]. This result indicated that the absolute configuration at C-25 of 1 should be S. Thus, the complete structure of 1 was elucidated as (25S)-20,22-O-(R-ethylidene)inokosterone.
Table
Table 1. The 1H-NMR (400 MHz) spectral data [δ (ppm), J in Hz] of 1–4 and 8.
Table 1. The 1H-NMR (400 MHz) spectral data [δ (ppm), J in Hz] of 1–4 and 8.
No.δH (1) aδH (2) aδH (3) aδH (4) aδH (8) b
11.77 (m), 1.41(m)1.78 (m)1.78 (m)1.79(m)2.15 (m), 1.93 (m)
23.82 (m)3.82 (m)3.82 (m)3.82 (m)4.19 (m)
33.94 (m)3.94 (m)3.94 (m)3.94 (m)4.23 (m)
41.73 (m), 1.69 (m)1.71 (m)1.73 (m), 1.69 (m)1.72 (m)2.04 (m), 1.82 (m)
52.38 (m)2.36 (m)2.37 (m)2.35 (m)3.01 (dd, 13.2, 3.2)
75.80 (d, 2.0)5.81 (s)5.80 brs5.80 (d, 2.0)6.26 (d, 1.6)
93.13 (m)3.13 (m)3.13 (m)3.13 (m)3.60 (m)
111.79 (m), 1.67 (m)1.79 (m), 1.68 (m)1.79 (m), 1.67 (m)1.78 (m), 1.68 (m)1.88 (m), 1.73(m)
122.09 (m), 1.82 (m)2.09 (m), 1.83 (m)2.09 (m), 1.82 (m)2.09 (m), 1.83 (m)2.17 (m), 1.92 (m)
151.94 (m), 1.60 (m)1.91 (m), 1.61 (m)1.94 (m), 1.60 (m)1.91 (m), 1.61 (m)2.60 (m), 2.04 (m)
161.92 (m), 1.87 (m)1.92 (m)1.92 (m), 1.87 (m)1.93 (m)2.46 (m), 2.08 (m)
172.32 (m)2.34 (m)2.28 (m)2.32 (m)2.95 (t, 9.2)
180.85 (s)0.84 (s)0.81 (s)0.85 (s)1.22 (s)
190.95 (s)0.95 (s)0.95 (s)0.96 (s)1.07 (s)
211.13 (s)1.15 (s)1.15 (s)1.15 (s)1.59 (s)
223.65 (dd, 8.8, 3.6)3.64 (m)3.68 (dd, 9.6, 2.8)3.63 (m)3.86 (d, 10.4)
231.49 (m)1.54 (m)1.47 (m)1.52 (m)1.94 (m), 1.63 (m)
241.50 (m), 1.15 (m)1.72 (m), 1.45 (m)1.68 (m), 1.15 (m)1.71 (m)2.17 (m), 1.41 (m)
251.61 (m) 1.63 (m) 1.81 (m)
263.34 (dd, 10.4, 6.4)1.19 (s)3.34 (dd, 10.4, 6.4)1.19 (s)3.64 (dd, 10.0, 6.4)
3.42 (dd, 10.4, 5.6) 3.42 (dd, 10.4, 5.6) 3.76 (dd, 10.0, 5.2)
270.93 (d, 6.8)1.20 (s)0.93 (d, 6.4)1.20 (s)1.03 (d, 6.4)
1'5.05 (q, 4.8)4.97 (t, 4.0) 5.05 (q, 4.8)
2'1.29 (d, 4.8)1.90 (m)1.30 (s)1.29 (d, 4.8)
3' 2.41 (t, 7.2)1.37 (s)
4'-OCH3 3.65 (s)
a Data were measured in CD3OD; b Data were measured in C5D5N.
Table
Table 2. The 13C-NMR (100 MHz) spectral data [δ (ppm)] of compounds 1–4 and 8.
Table 2. The 13C-NMR (100 MHz) spectral data [δ (ppm)] of compounds 1–4 and 8.
PositionδC (1) aδC (2) aδC (3) aδC (4) aδC (8) b
137.3 (t)37.3 (t)37.3 (t)37.3 (t)38.0 (t)
268.7 (d)68.7 (d)68.7 (d)68.7 (d)68.1
368.5 (d)68.5 (d)68.5 (d)68.5 (d)68.1
432.9 (t)32.8 (t)32.8 (t)32.9 (t)32.5 (t)
551.8 (d)51.8 (d)51.8 (d)51.8 (d)51.4 (d)
6206.4 (s)206.5 (s)206.4 (s)206.4 (s)203.5 (s)
7122.2 (d)122.2 (d)122.2 (d)122.1 (d)121.7 (d)
8167.5 (s)167.6 (s)167.6 (s)167.6 (s)166.1 (s)
935.1 (d)35.1 (d)35.1 (d)35.1 (d)34.5 (d)
1039.2 (s)39.2 (s)39.2 (s)39.2 (s)38.7 (s)
1121.5 (t)21.5 (t)21.5 (t)21.5 (t)21.1 (t)
1232.2 (t)32.2 (t)32.3 (t)32.1 (t)31.8 (t)
1349.0 (s) *49.0 (s) *49.0 (s) *49.0 (s) *48.1 (s)
1485.2 (s)85.2 (s)85.3 (s)85.2 (s)84.2 (s)
1531.7 (t)31.7 (t)31.7 (t)31.7 (t)32.1 (t)
1622.6 (t)22.6 (t)22.4 (t)22.6 (t)21.7 (t)
1751.3 (d)51.4 (d)50.5 (d)51.3 (d)50.1 (d)
1817.6 (q)17.6 (q)17.6 (q)17.6 (q)17.9 (q)
1924.4 (q)24.4 (q)24.4 (q)24.4 (q)24.5 (q)
2085.3 (s)85.3 (s)85.7 (s)85.3 (s)77.3 (s)
2123.6 (q)23.4 (q)22.5 (q)23.7 (q)21.5 (q)
2285.5 (d)85.6 (d)83.1 (d)85.6 (d)76.8 (d)
2327.3 (t)24.6 (t)27.4 (t)24.6 (t)30.3 (t)
2432.0 (t)42.2 (t)32.0 (t)42.2 (t)32.0 (t)
2537.0 (d)71.1 (s)37.0 (d)71.1 (s)36.8 (d)
2668.2 (t)29.5 (q)68.2 (t)29.5 (q)67.4 (t)
2717.0 (q)28.9 (q)17.0 (q)28.9 (q)17.8 (q)
1'102.3 (d)103.9 (d)108.0 (s)102.3 (d)
2'22.0 (q)31.0 (t)29.3 (q)22.0 (q)
3' 29.2 (t)27.2 (q)
4' 175.6 (s)
4'-OCH3 52.1 (q)
a Data recorded in CD3OD; b Data recorded in C5D5N; * The signal is overlapped by solvent.
Molecules 17 03324 g002 550
Figure 2. Key NOE ( Molecules 17 03324 i001) correlations of 1 and 2.
Figure 2. Key NOE ( Molecules 17 03324 i001) correlations of 1 and 2.
Molecules 17 03324 g002
Compound 2 was also obtained as a white amorphous powder. HR-EIMS showed a [M]+ ion at m/z 578.3450, corresponding to the molecular formula C32H50O9 (calcd for C32H50O9, 578.3449). The spectroscopic data (IR, UV, and NMR: See Section 3.3. and Table 1 and Table 2) suggested 2 was an ecdysteroid closely related to 20,22-O-(R-ethylidene)-20-hydroxyecdysone, a reported [24,25] ecdysteroid which was also obtained in the present study (compound 4). Further comparison of the 1H- and 13C-NMR spectra showed that the signals for the C2 acetal group in 4 were absent in 2. Instead, additional signals for one acetalated 3-methoxycarbonyl-propylal group [δH 4.97 (1H, t, H-1'), 3.65 (3H, s, 4'-OCH3), 2.41 (3H, H3-3'), 1.90 (3H, H3-2'); δC 175.6 (C-4'), 103.9 (C-1'), 52.1 (4'-OCH3), 31.0 (C-3'), 29.2 (C-2')] were exhibited in the spectra. 1H-1H COSY and HSQC spectra permitted establishment of the spin system from C-1' through C-3'. The HMBC correlations from 4'-OCH3 (δH 3.65), H2-3' (δH 2.41) and H2-2' (δH 1.91) to C-4' (δC 175.6), and from H2-2', H2-3' to C-1' (δC 103.9) indicated the linkage from C-1' to 4'-OCH3. The R configuration at C-1' was determined by the important NOE correlation between H-1' and H-22 (Figure 2). These findings led to the establishment of the whole structure of 2 as shown in Figure 1, and this structure was further well supported by other important 1H-1H COSY, HMBC and NOESY correlations. Therefore, 2 was determined as 20,22-O-(R-3-methoxycarbonyl)propylidene-20-hydroxyecdysone.
Compound 3, showing the molecular formula C28H44O7, was deduced to be the same ecdysteroid compound inokosterone-20,22-acetonide from the roots of Leuzea carthamoides recently reported in the literature [22], by comparison of its spectroscopic data (Table 1 and Table 2) with reported values. However, at that time the authors had yet not clarified the absolute configuration at C-25 in the structure. In order to determine the stereochemistry at C-25 in the structure of 3, a similar acid hydrolysis like that performed for 1 was conducted, and the free ecdysteroid that was released from 3 was confirmed to be (25S)-inokosterone (8) on the basis of a co-TLC elution test and NMR analyses, suggesting that the absolute configuration at C-25 in 3 should also be S configuration. Therefore, the complete structure of 3 was determined as (25S)-inokosterone-20,22-acetonide.
The other five known compounds were identified as 20,22-O-(R-ethylidene)-20-hydroxyecdysone (4) [24,25], 20-hydroxyecdysone-20,22-monoacetonide (5) [25,26], 20-hydroxyecdysone (6) [27], (25R)-inokosterone (7) [23,28] and (25S)-inokosterone (8) [23,28], by interpretation of their spectroscopic data, as well as by comparison with literature values.
Among the eight isolated compounds, 1 and 2 are two new phytoecdysteroids, each characterized by having an acetal group in the molecule. In particular, 2 is so far the first example of phytoecdysteroid acetalated at the side chain with a 4-oxobutanoic acid unit. Compounds 3–5 were found in Achyranthes bidentata roots for the first time.

3. Experimental

3.1. General

Optical rotations were measured on a Perkin-Elmer 341 polarimeter with MeOH as solvent. UV spectra were recorded in MeOH on a Perkin-Elmer Lambda 35 UV-Vis spectrophotometer. IR spectra (KBr) were taken on a Bruker Tensor 27 spectrophotometer in cm−1. NMR spectra were recorded in C5D5N and CD3OD on a Bruker DRX-400 instrument using the residual solvent peak as reference. ESIMS were collected on an MDS SCIEX API 2000 LC/MS/MS instrument. HRESIMS data were obtained on a Water Q-TOF Premier mass spectrometer and HREIMS data were obtained on a Finigan MAT 95XP mass spectrometer. Preparative HPLC was conducted using a CXTH P3000 HPLC pump and a UV3000 UV-Vis Detector with a Fuji-C18 column (10 µm–100 A). For column chromatography (CC), silica gel (200–300 mesh, Qingdao Marine Chemical Inc., Qingdao, China), YMC ODS-A (50 μm, YMC Co. Ltd., Kyoto, Japan) and Sephadex LH-20 (Pharmacia Fine Chemical Co. Ltd., Uppsala, Sweden) were used. Fractions were monitored by TLC, and spots were visualized by heating the silica gel plates sprayed with 10% H2SO4 in ethanol.

3.2. Plant Materials

Roots of A. bidentata Blume were purchased from Anguo Professional Market for Chinese Materia Medica, in April 2010, and were collected in Anguo County, Hebei Province, China. Plants were authenticated by Fu-Wu Xing (South China Botanical Garden, Chinese Academy of Sciences), and a voucher specimen (No. 20100408A) was deposited in the Laboratory of Phytochemistry of South China Botanical Garden, Chinese Academy of Sciences.

3.3. Extraction and Isolation

Powder of the dry roots of A. bidentata (5.10 kg) was extracted with EtOH-H2O (95:5, 10 L × 3) at room temperature three times (24 h each). The EtOH extracts were combined and concentrated in vacuo. Then, the resulting residue was suspended in H2O (1.5 L) and sequentially extracted with petroleum ether (5 L × 3), EtOAc (5 L × 3) and n-BuOH (5 L × 3). The EtOAc layer was evaporated in vacuo to yield EtOAc-soluble fraction (17.5 g).
The EtOAc-soluble fraction was subjected to silica gel CC using a gradient of CHCl3-MeOH (95:5–60:40, v/v) to give ten fractions (E1–E10). Fraction E8 (3.90 g), obtained by elution with CHCl3-MeOH (85:15, v/v), was further subjected to silica gel CC and successively eluted with CHCl3-MeOH (20:1–10:1, v/v) to yield six sub-fractions (E6–1–E6–6). Sub-fraction E6–4 (0.370 g) was separated by an ODS column using MeOH-H2O (60:40–100:0, v/v), followed by HPLC preparation with MeOH-H2O (70:30, v/v) at a flow rate of 10 mL/min to afford compounds 2 (5.9 mg, tR = 41 min), 4 (6.8 mg, tR = 49 min), 3 (6.0 mg, tR = 61 min), 1 (5.0 mg, tR = 65 min), and 5 (9.3 mg, tR = 67 min). Sub-fraction E6–5 (0.200 g ) was purified by Sephadex LH-20 CC using MeOH as eluent, followed by preparative HPLC using MeOH-H2O (40:60, v/v) at a flow rate of 8 mL/min to afford compounds 6 (tR = 96 min, 20.0 mg), 7 (tR = 114 min, 29.0 mg) and 8 (tR = 127 min, 38.0 mg).
(25S)-20,22-O-(R-Ethylidene)inokosterone (1). White amorphous powder; [α] Molecules 17 03324 i002 + 26.8 (c = 0.35, MeOH); IR (KBr) νmax 3419, 2934, 1654 ,1450, 1139, 1156 cm−1; UV (MeOH) λmax (log ε) nm: 242 (4.14); ESIMS (+) m/z 529 [M+Na]+, 507 [M+H]+; ESIMS (−) m/z 505 [M–H]–; HRESIMS (−) m/z 505.3173 [M−H]– (calcd. for C29H45O7, 505.3160); 1H-NMR (CD3OD, 400 MHz) and 13C-NMR (CD3OD, 100 MHz) data are shown in Table 1 and Table 2.
20,22-O-(R-3-Methoxycarbonyl)propylidene-20-hydroxyecdysone (2). White amorphous powder; [α] Molecules 17 03324 i003 + 34.0 (c = 0.20, MeOH); IR (KBr) νmax 3423, 2964, 1737, 1654, 1382, 1139, 1058 cm−1; UV (MeOH) λmax (log ε) nm: 242 (3.75); ESIMS (+) m/z 601 [M+Na]+, 579 [M+H]+; ESIMS (−) m/z 577 [M−H]−; HREIMS m/z 578.3450 [M]+ (calcd. for C32H50O9, 578.3449); 1H-NMR (CD3OD, 400 MHz) and 13C-NMR (CD3OD, 100 MHz) data are shown in Table 1 and Table 2.
(25S)-Inokosterone-20,22-acetonide (3). White amorphous powder; ESIMS (+) m/z 520 [M+Na]+; ESIMS (−) m/z 555 [M+Cl]−, 519 [M−H]−; 1H-NMR (CD3OD, 400 MHz) and 13C-NMR (CD3OD, 100 MHz) data are shown in Table 1 and Table 2.
20,22-O-(R-Ethylidene)-20-hydroxyecdysone (4). White amorphous powder; ESIMS (+) m/z 545 [M+K]+, 529 [M+Na]+; ESIMS (−) m/z 541 [M+Cl]−, 505 [M−H]−; 1H-NMR (CD3OD, 400 MHz) and 13C-NMR (CD3OD, 100 MHz) data are shown in Table 1 and Table 2.
(25S)-Inokosterone (8). White amorphous powder; ESIMS (+) m/z 519 [M+K]+, 503 [M+Na]+; ESIMS (−) m/z 515 [M+Cl]−; 1H-NMR (C5D5N, 400 MHz) and 13C-NMR (C5D5N, 100 MHz) data are shown in Table 1 and Table 2.

3.4. Acidic Hydrolysis of Compounds 1 and 3

Individual solutions of 1 (2.5 mg) and 3 (3.0 mg) in 1 M H2SO4 (0.5 mL) were allowed to stand at room temperature for 12 h with continuous oscillation. Each reaction mixture was subsequently extracted with CHCl3 (1 mL) and EtOAc (1 mL × 3), and the EtOAc-soluble fraction was concentrated to dryness to give a free ecdysteroid (1.5 mg from 1 and 1.8 mg from 3). Both hydrolysates were identified as the known compound (25S)-inokosterone (8).

4. Conclusions

Two new phytoecdysteroids, (25S)-20,22-O-(R-ethylidene)inokosterone (1) and 20,22-O-(R-3-methoxycarbonyl)propylidene-20-hydroxyecdysone (2), were isolated from the roots of Achyranthes bidentata Blume, along with six known ones. Three out of the six known compounds 3–5 were found in this plant species for the first time. Compound 2 is so far the first example of phytoecdysteroid acetalated at the side chain with a 4-oxobutanoic acid unit. The absolute configuration at C-25 in the structure of known compound 3 was further established in this study.

Supplementary Materials

Supplementary materials can be accessed at: https://www.mdpi.com/1420-3049/17/3/3324/s1.

Acknowledgments

We wish to acknowledge the National Natural Science Foundation of China (No.30870248) and the Knowledge Innovation Program of the Chinese Academy of Sciences (KSCX2-YW-N-0804).

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  • Sample Availability: Samples of the compounds are available from the authors.

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MDPI and ACS Style

Zhang, M.; Zhou, Z.-Y.; Wang, J.; Cao, Y.; Chen, X.-X.; Zhang, W.-M.; Lin, L.-D.; Tan, J.-W. Phytoecdysteroids from the Roots of Achyranthes bidentata Blume. Molecules 2012, 17, 3324-3332. https://doi.org/10.3390/molecules17033324

AMA Style

Zhang M, Zhou Z-Y, Wang J, Cao Y, Chen X-X, Zhang W-M, Lin L-D, Tan J-W. Phytoecdysteroids from the Roots of Achyranthes bidentata Blume. Molecules. 2012; 17(3):3324-3332. https://doi.org/10.3390/molecules17033324

Chicago/Turabian Style

Zhang, Mei, Zhong-Yu Zhou, Jing Wang, Yong Cao, Xue-Xiang Chen, Wei-Min Zhang, Li-Dong Lin, and Jian-Wen Tan. 2012. "Phytoecdysteroids from the Roots of Achyranthes bidentata Blume" Molecules 17, no. 3: 3324-3332. https://doi.org/10.3390/molecules17033324

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