Four New Unusual Pentacyclic Triterpenoids from the Roots of Jasminum sambac (L.) Ait
1
Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
2
Xiamen Institute of Rare-Earth Materials, Chinese Academy of Sciences, Xiamen 361021, China
3
University of Chinese Academy of Sciences, Beijing 100049, China
*
Authors to whom correspondence should be addressed.
Molecules 2023, 28(13), 5097; https://doi.org/10.3390/molecules28135097
Submission received: 17 May 2023
/
Revised: 9 June 2023
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Accepted: 10 June 2023
/
Published: 29 June 2023
(This article belongs to the Section Medicinal Chemistry)
Abstract
:Four new unusual pentacyclic triterpenoids (1–4) were isolated from the roots of Jasminum sambac (L.) Ait. Their structures were elucidated by 1D and 2D NMR analysis, single-crystal X-ray diffraction and HRESIMS.
1. Introduction and Structural Elucidation
Jasminum (Oleaceae) is a genus with over 200 species, which are native to Asia, Australia, Africa, and the southern Pacific Islands [1]. Phytochemical investigations on some of the Jasminum species have revealed the presence of secoiridoids, lignans, triterpenoids, flavonoids, and sesquiterpenoids [2,3,4,5,6,7,8,9]. The roots of Jasminum sambac (L.) Ait., which have anesthetic and analgesic effects, are used in traditional Chinese medicine for the treatment of insomnia, headaches, decayed teeth, and injuries from falls. It was recorded that the roots are thought to be one important ingredient of “Ma-Fei-San”, which was created by Tuo Hua and used for surgeries due to its significant anesthetic and analgesic effects. Consequently, it is essential to study the ingredients of the roots of Jasminum sambac (L.) Ait. in depth.
In our previous work, we isolated and confirmed some compounds (triterpenoid, sesquiterpenoids, lignans and glycoside) from the roots of Jasminum sambac (L.) Ait. [10,11]. Here, we report the isolation and elucidation of another four new unusual pentacyclic triterpenoids (1–4) (Their structures are shown in Figure 1) from the roots of Jasminum sambac (L.) Ait.
Compound 1, Golden yellow solid, M.p 61–62 °C, HPLC purity: 96.596%, retention time: 17.067 min. Crystal data: orthorhombic, space group P212121 (no. 19), a = 7.8148(3)Å, b = 13.1614(6)Å, c = 25.3786(11)Å, V = 2610.28(19)Å3, Z = 4, T = 272.00 K, μ(Mo Kα) = 0.091 mm−1, Dcalc = 1.284 g/cm3, 22,104 reflections measured (5.454° ≤ 2θ ≤ 54.36°), and 5766 unique (Rint = 0.0704, Rsigma = 0.0650) which were used in all calculations. The final R1 was 0.0536 (I > 2σ(I)) and wR2 was 0.1512.
The molecular formula was confirmed as “C30H32O7” through HRESIMS (m/z: found: 527.2040 [M + Na]+, calcd.: 527.2040). The 1H NMR spectrum showed six methyl groups at [δH: 1.26 (d, J = 4.4 Hz, H-12′), 1.32 (d, J = 4.4 Hz, H-17), 1.45 (s, H-16), 1.72 (s, H-18), 2.24 (s, H-15), and 2.31 (s, H-11′)] ppm; two aromatic protons at [δH: 6.84 (s, H-6) and 6.93 (s, H-6′)] ppm; five hydroxyl protons at [δH: 5.35 (s, 4-OH), 8.99 (s, 4′-OH), 9.10 (s, 8-OH), 11.78 (s, 7-OH), and 12.53 (s, 5′-OH)] ppm. The 13C NMR together with the DEPT spectra revealed thirty signals, including: six methyls (C-15, C-16, C-17, C-18, C-11′, and C-12′); two methylenes (C-2 and C-3); two methines (C-10 and C-8′); three olefinic methines (C-6, C-2′, and C-6′), and seventeen quaternary carbons (C-1, C-4, C-5, C-7, C-8, C-9, C-11, C-12, C-13, C-14, C-1′, C-3′, C-4′, C-5′, C-7, C-9′ and C-10). The HMBC correlations (Figure 2): from 4-OH (δH 5.35) to C-16 (δC 28.9), C-3 (δC 34.8), and C-4 (δC 71.1); from 8-OH (δH 9.10) to C-6 (δC 124.0) and C-8 (δC 148.3); from 7-OH (δH 11.78) to C-13 (δC 116.1), C-7 (δC 143.4), and C-8 (δC 148.3); from 4′-OH (δH 8.99) to C-6′ (δC 123.9) and C-4′ (δC 148.4); and from 5′-OH (δH 12.53) to C-10′ (δC 114.8), C-5′ (δC 143.6), and C-4′ (δC 148.4) supported the “hydroxyl groups” at C-4, C-7, C-8, C-5′ and C-4′, respectively. 1H-1H COSY correlations (Figure 2): from H-6′/H-12′ and H-8′/H-2′/H-11′ coupled with the guidance of HMBC correlations: from H-2′ (δH 5.69) to C-8′ (δC 35.5) and C-10′ (δC 114.8); from H-6′ (δH 6.93) to C-9′ (δC 137.2), C-5′ (δC 143.5), and C-4′ (δC 148.4); from H-11′ (δH 2.31) to C-10′ (δC 114.8), C-7′ (δC 124.5), C-9′ (δC 137.2), and C-4′ (δC 148.4); and from H-12′ (δH 1.26) to C-8′ (δC 35.5) and C-9′ (δC 137.2) indicated the presence of the methylnaphthalen-1onyl group. Likewise, the correlations from H-10 (δH 4.01) to C-17 (δC 28.1), C-4 (δC 71.1), and C-12 (δC 137.1); from H-15 (δH 2.24) to C-13 (δC 116.1), C-5 (δC 123.8), and C-14 (δC 136.9); from H-17 (δH 1.32) to C-10 (δC 33.1) and C-14 (δC 136.9); from H-16 (δH 1.45) to C-3 (δC 34.8) and C-4 (δC 71.1), accompanied with 1H-1H COSY correlations of H-6/H-17 and H-10/H-15/H-17, revealed the existence of hydroanthracen-9-onyl moiety. The methylnaphthalen-1-onyl and hydroanthracen-9-onyl groups of compound 1 were connected by analyzing the HMBC correlation from H-2′ (δH 5.69) to C-1 (δC 43.9), which was also supported by 1H-1H COSY correlation of H-2′/H-2/H-3. The ROESY correlations (Figure 3) showed that H-10 (δH 4.01) correlates with Me-16 (δH 1.45), Me-11′ (δH 2.31), and H-8′ (δH 4.17) correlates with Me-15 (δH 2.24), Me-18 (δH 1.72) and 4-OH (δH 5.35), which indicated its relative configuration. The detailed 1H and 13C NMR are shown in Table 1. The single-crystal X-ray diffraction analysis confidently confirmed its absolute configuration (CCDC 2259478; the XRD structure is shown in Figure 4).
Compound 2, Yellow solid, M.p 58–59 °C, HPLC purity: 92.29%, retention time: 18.807 min. The molecular formula was confirmed as “C30H34O6” through HRESIMS (m/z: 513.2247 [M + Na]+, calcd.: 513.2248). The 1H and 13C NMR data (Table 1) revealed six methyls at [δH 0.94 (d, J = 4.4 Hz, H-17), δH 0.99 (s, H-15), δH 1.26 (d, J = 4.5 Hz, H-12′), δH 1.51 (s, H-16), δH 1.58 (s, H-18), and δH 2.25 (s, H-11′)] ppm; one aromatic proton at [δH 6.89 (s, H-6′)] ppm; and three hydroxyl protons at [δH 5.40 (s, 4-OH), δH 9.07 (1H, s, 4′-OH) and δH 12.23 (s, 5′-OH)] ppm, which are identical to those of compound 1.
The 1H-1H COSY of H-17/H-5/H-6/H-7, H-15/H-10, H-16/H-15/H-3, H-18/H-11′/H-2, H-12′/H-6′/H-8 of compound 2 (Figure 2), guided by HMBC correlations (Figure 2) from H-17 (δH 0.94) to C-5 (δC 29.6) and C-7 (δC 42.4); from H-15 (δH 0.99) to C-6 (δC 38.3) and C-10 (δC 39.6); from H-12′ (δH 1.26) to C-8′ (δC 31.7) and C-9′ (δC 137.4); from H-16 (δH 1.51) to C-3 (δC 35.0) and C-4 (δC 70.1); from H-18 (δH 1.58) to C-2 (δC 33.1), C-1 (δC 43.8), C-11 (δC 135.5); and from H-11′ (δH 2.25) to C-8′ (δC 31.7), C-7′ (δC 123.6), C-9′ (δC 137.4) are aided in assigning the positions of methyl groups. In addition, the HMBC correlations from 4-OH (δH 5.40) to C-16 (δC 27.8), C-3 (δC 35.0) and C-4 (δC 70.1); from 4′-OH (δH 9.07) to C-6′ (δC 123.9), C-5′ (δC 143.5), and C-4′ (δC 148.7), and from 5′-OH (δH 12.23) to C-10′ (δC 115.8), C-5′ (δC 143.5), and C-4′ (δC 148.7) indicated the positions of the hydroxyl groups. The correlations from H-6′ (δH 6.89) to C-11′ (δC 17.7), C-9′ (δC 137.4), C-5′ (δC 143.5), and C-4′ (δC 148.7) revealed the position of aromatic proton. Its relative configuration of H-8′/H-5/4-OH and H-10/Me-16/Me-17/Me-11′ is supported by ROSY correlations (Figure 3).
Compound 3, Yellow solid, M.p 73–74 °C, HPLC purity: 96.67%, retention time: 12.407 min. The molecular formula was confirmed as “C30H34O6” through HRESIMS (m/z: 513.2247 [M + Na]+, calcd.: 513.2248). The 1H and 13C NMR data are closely similar to those of compound 2, except that the positions of the olefinic bond between C-13 and C-14 of compound 2 shifted to C-6 and C-14 of compound 3, which revealed the appearance of two peaks at δC 126.4 and δC 158.1 ppm for C-6 and C-14, respectively. This was also supported on the basis of HMBC correlations from H-5 (δH 6.47) to C-10 (δC 39.6), C-14 (δC 158.1), and C-9 (δC 187.8). The position of Me-17 in compound 3 was assigned with the guidance of HMBC correlation from H-17 (δH 0.84) to C-13 (δC 39.6) and C-7 (δC 41.7) (Figure 2). The relative configuration of compound 3 was similar to compound 2, which was determined by ROESY (Figure 3). The detailed 1H and 13C NMR are shown in Table 1.
Compound 4, Yellow solid, M.p 96–98 °C, HPLC purity: 98.83%, retention time: 21.400 min. The molecular formula was confirmed as “C30H40O5” through HRESIMS (m/z: 503.2771 [M + Na]+, calcd.: 503.2768). The 1H NMR data showed four tertiary methyls at [δH 0.86 (s, H-17), δH 1.49 (s, H-16), δH 1.44 (s, H-18) and δH 0.93 (s, H-12′)] ppm and two secondary methyls at [δH 0.97 (d, J = 4.6 Hz, H-15) and δH 0.99 (d, J = 2.9 Hz, H-11′)] ppm. The 13C NMR together with DEPT revealed 30 carbon signals, including: six methyls (C-15, C-16, C-17, C-18, C-11′, and C-12′); six methylenes (C-2, C-3, C-5, C-6, C-6′, and C-7′); two oxygenated methines (C-9 and C-3′); three olefinic methines (C-8, C-2′, and C-4′); five sp2 quaternary carbons (C-11, C-12, C-13, C-1′, and C-10′); and six sp3 quaternary carbons (C-1, C-4, C-14, C-9′, C-7 and C-5′). The 1H and 13C NMR data (Table 1) resembled those of (1S*,5S*,10aR*)-1-[(8′,8a′-dimethyl-4′-oxo-1′,4′,6′,7′,8′,8a′-hexahydronaphthalene-2′-yl]-4-hydroxy-1,4,5,10atetramethyl-1,2,3,4,5,6,7,9,10,10a-decahydroanthracen-9-one [4] (which was isolated from the J. sambac roots), except that the two carbonyl groups of (1S*,5S*,10aR*)-1-[(8′,8a′-dimethyl-4′-oxo-1′,4′,6′,7′,8′,8a′-hexahydronaphthalene-2′-yl]-4-hydroxy-1,4,5,10a tetramethyl-1,2,3,4,5,6,7,9,10,10a-decahydroanthracen-9-one were replaced with hydroxyl groups of compound 4. The hydroxyl groups of compound 4 were assigned according to HMBC correlations (Figure 2): from H-9 (δH 4.17) to C-17 (δC 18.1), C-1 (δC 41.9), C-4 (δC 68.8), C-13 (δC 139.1); and from H-3′ (δH 4.51) to C-12′ (δC 18.4), C-8′ (δC 30.6), C-9′ (δC 41.6), C-10′ (δC 136.6), and C-4′ (δC 139.2), which are accompanied by 1H-1H COSY correlations of H-9/H-15/H-8 and H-3′/H-2′/H-11′/H-4′. In addition, the 13C and DEPT spectra indicated the presence of two carbonyl groups, unlike those of (1S*,5S*,10aR*)-1-[(8′,8a′-dimethyl-4′-oxo-1′,4′,6′,7′,8′,8a′-hexahydronaphthalene-2′-yl]-4-hydroxy-1,4,5,10a tetramethyl-1,2,3,4,5,6,7,9,10,10a-decahydroanthracen-9-one. The positions of methyl groups at C-10 and C-8′ were established by HMBC correlations from Me-15 (δH 0.97) to C-5 (δC 25.6), C-10 (δC 30.7), and C-14 (δC 42.8) and Me-11′ (δH 0.99) to C-7′ (δC 25.4), C-8′ (δC 30.6) and C-9′ (δC 41.6). The ROESY correlations of H-3′/Me-11′/Me-12′/Me-16/H-10 and H-9/Me-17/Me-18/H-8′ (Figure 3) established its relative configuration.
2. Conclusions
In conclusion, we have isolated and confirmed four new unusual pentacyclic triterpenoids from the roots of Jasminum sambac (L.) Ait (The detailed NMR, HRESIMS, and HPLC data were shown in Supplementary Materials). This work has discovered new compounds from the roots of Jasminum sambac (L.) Ait. and has also enriched understanding of the types of triterpenoids.
Supplementary Materials
The following supporting information can be downloaded at https://www.mdpi.com/article/10.3390/molecules28135097/s1, including the detailed isolation processes; 1H- and 13C-NMR spectral data; HR-ESIMS, and XRD.
Author Contributions
O.Z.O. isolated the compounds, finished the NMR analysis and prepared the original manuscript. J.Y. elucidated the NMR, HMBC, 1H-1H COSY, and ROESY and completed the manuscript revision and editing. C.L. provided supervision and the work plan, revised the HMBC, 1H-1H COSY, and ROESY and revised the final manuscript. All authors have read and agreed to the published version of the manuscript.
Funding
The National Natural Science Foundation of China (21875252), and Science and Technology Planning Program of Xiamen (No. 2022CXY0702).
Institutional Review Board Statement
Not applicable.
Informed Consent Statement
Not applicable.
Data Availability Statement
Not applicable.
Conflicts of Interest
The authors declare no conflict of interest.
Sample Availability
Not applicable.
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Figure 1.
Structures of compounds (1–4).
Figure 2.
Structures with key 1H-1H COSY and HMBC correlations of the compounds 1 to 4.
Figure 3.
Key ROESY correlations of compounds 1 to 4.
Figure 4.
X-ray crystal structure for compound 1.
Table 1.
1H(400 MHz) and 13C(100 MHz) NMR data for compounds 1 and 2 in DMSO-d6. and compounds 3 and 4 in CD3OD (δ in ppm and J in Hz).
Table 1.
1H(400 MHz) and 13C(100 MHz) NMR data for compounds 1 and 2 in DMSO-d6. and compounds 3 and 4 in CD3OD (δ in ppm and J in Hz).
| No. | Compound 1 | Compound 2 | Compound 3 | Compound 4 | ||||
|---|---|---|---|---|---|---|---|---|
| 1H | 13C | 1H | 13C | 1H | 13C | 1H | 13C | |
| 1 | 43.9 C | 43.8 | 44.4 C | 41.9 C | ||||
| 2α | 1.98, m | 39.2 CH2 | 1.90, m | 33.1 CH2 | 1.85, dt(3.4, 2.5) | 34.0 CH2 | 1.24, m | 29.4 CH2 |
| 2β | 2.12, m | 1.53, m | 2.18, m | |||||
| 3α | 1.80, m | 34.8 CH2 | 1.61, m | 35.0 CH2 | 2.02, m | 35.5 CH2 | 1.76, m | 33.7 CH2 |
| 3β | 2.15, m | |||||||
| 4 | 71.1 C | 70.1 C | 71.3 C | 68.8 C | ||||
| 5 | 123.8 C | 1.22, m | 29.2 CH2 | 6.47, s | 126.4 CH | 2.30, m | 25.6 CH2 | |
| 6α | 6.84 | 123.9 CH | 2.56, m | 38.3 CH2 | 2.58, d(11.8) | 38.5 CH2 | 1.60, m | 26.0 CH2 |
| 6β | 2.46 | |||||||
| 7α | 143.4 C | 2.43, d(1.8) | 42.4 CH2 | 2.39, d(2.1) | 41.7 CH2 | 188.7 C | ||
| 7β | 2.21, m | 2.27, m | ||||||
| 8 | 148.3 C | 199.6 C | 200.4 C | 7.01, s | 139.9 CH | |||
| 9 | 191.9 C | 191.9 C | 187.8 C | 4.17, s | 67.9 CH | |||
| 10 | 4.01, q(4.4) | 33.1 CH | 3.26, m | 39.6 CH | 3.76, m | 39.9 CH | 2.24 | 30.7 CH |
| 11 | 137.1 C | 135.5 C | 136.7 C | |||||
| 12 | 148.34 | 148.8 C | 142.9 C | |||||
| 13 | 116.1 C | 135.6 C | 39.6 C | 139.1 C | ||||
| 14 | 136.9 C | 157.7 C | 158.1 C | 42.8 C | ||||
| 15 | 2.24, s | 17.7 CH3 | 0.99, s | 17.6 CH3 | 1.04, s | 16.8 CH3 | 0.97, s | 14.0 CH3 |
| 16 | 1.45, s | 28.9 CH3 | 1.51, s | 27.8 CH3 | 1.45, s | 27.2 CH3 | 1.49, s | 26.3 CH3 |
| 17 | 1.32, d(4.4) | 28.1 CH3 | 0.94, d(4.4) | 15.3 CH3 | 0.84, d(4.8) | 13.7 CH3 | 0.86, s | 18.1 CH3 |
| 18 | 1.72, s | 23.2 CH3 | 1.58, s | 25.6 CH3 | 1.73, s | 23.4 CH3 | 1.44, s | 23.1 CH3 |
| 1′ | 168.9 C | 167.5 C | 168.8 C | 138.5 C | ||||
| 2′ | 5.69, s | 121.9 CH | 6.27, d(0.7) | 126.8 CH | 6.89, s | 122.9 CH | 5.79, s | 125.7 CH |
| 3′ | 191.8 C | 186.9 C | 191.2 C | 4.51, s | 66.2 CH | |||
| 4′ | 148.4 C | 148.7 C | 147.9 C | 6.96, s | 139.2 CH | |||
| 5′ | 143.6 C | 143.5 C | 142.9 C | 187.2 C | ||||
| 6′ | 6.93, s | 124.0 CH | 6.89, s | 123.9 CH | 6.90, s | 122.4 CH | 2.28, m | 25.9 CH2 |
| 7′ | 124.5 C | 123.6 C | 123.7 C | 1.58, m | 25.4 CH2 | |||
| 8′ | 4.17, q(4.8) | 35.5 CH | 4.29, q(4.5) | 31.7 CH | 4.09, q(4.4) | 33.1 CH | 2.30 | 30.6 CH |
| 9′ | 137.2 C | 137.4 C | 136.8 C | 41.6 C | ||||
| 10′ | 114.8 C | 115.8 C | 115.2 C | 136.6 C | ||||
| 11′ | 2.31, s | 18.1 CH3 | 2.25, s | 17.7 CH3 | 2.32, s | 16.3 CH3 | 0.99, d(2.9) | 13.9 CH3 |
| 12′ | 1.26, d(4.4) | 24.4 CH3 | 1.26, d(4.5) | 27.9 CH3 | 1.42, d(4.4) | 26.7 CH3 | 0.93, s | 18.4 CH3 |
| 4-OH | 5.35, s | 5.40, s | ||||||
| 7-OH | 11.78, | |||||||
| 8-OH | 9.10, s | |||||||
| 4′-OH | 8.99, s | 9.07, s | ||||||
| 5′-OH | 12.53, s | 12.23, s | ||||||
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MDPI and ACS Style
Olatunde, O.Z.; Yong, J.; Lu, C. Four New Unusual Pentacyclic Triterpenoids from the Roots of Jasminum sambac (L.) Ait. Molecules 2023, 28, 5097. https://doi.org/10.3390/molecules28135097
AMA Style
Olatunde OZ, Yong J, Lu C. Four New Unusual Pentacyclic Triterpenoids from the Roots of Jasminum sambac (L.) Ait. Molecules. 2023; 28(13):5097. https://doi.org/10.3390/molecules28135097
Chicago/Turabian StyleOlatunde, Olagoke Zacchaeus, Jianping Yong, and Canzhong Lu. 2023. "Four New Unusual Pentacyclic Triterpenoids from the Roots of Jasminum sambac (L.) Ait" Molecules 28, no. 13: 5097. https://doi.org/10.3390/molecules28135097
