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Two New Ache Inhibitors Isolated from Li Folk Herb Heilaohu “Kadsura Coccinea” Stems

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Two New Ache Inhibitors Isolated from Li Folk Herb Heilaohu “Kadsura Coccinea” Stems molecules Article Two New AChE Inhibitors Isolated from Li Folk Herb Heilaohu “Kadsura coccinea” Stems 1, 2, 1 1, 1, Sheng Zhuo Huang y, Lin Ping Duan y, Hao Wang , Wen Li Mei * and Hao Fu Dai * 1 Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agriculture Sciences, Haikou 571101, China; [email protected] (S.Z.H.); [email protected] (H.W.) 2 College of Food Science and technology, Nanjing Agricultural University, Nanjing 210095, China; [email protected] * Correspondence: [email protected] (W.L.M.); [email protected] (H.F.D.); Tel./Fax: +86-0898-66968036 (H.F.D.) These people were contributed equally. y Received: 11 September 2019; Accepted: 7 October 2019; Published: 8 October 2019 Abstract: Two new triterpenoids, named kadsuricoccins A and B, together with three known ones, were isolated from the Li folk herb Heilaohu, the stems of Kadsura coccinea (Lem.) A. C. Smith, which was used for food and as a healthy supplement. Their structures were elucidated by comprehensive analyses of mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data. To search healthy components, an acetylcholinesterase (AChE) inhibitory activity test by Ellman’s Method was conducted, kadsuricoccins A and B showed activity with the AChE inhibit index (AII) up to 68.96% 0.19% and 57.8% 0.11% at 94 nM (compared with positive ± ± control tacrine AII 79.80% 0.20%, 9.4 nM), respectively. ± Keywords: Kadsura coccinea; Schisandraceae; AChE inhibitor; triterpenoid 1. Introduction With global exchange increase and dietary habit diversification, ethnic characteristic foods are becoming more and more popular. One of the unique ingredients of ethnic characteristic foods is their flavor agent, which could stimulate appetite, protect foods from spoilage and keep people healthy [1]. Living in the dangerous rainforest, the Li folk ancestors in Hainan Island had tested and screened out various herbs to treat disease and to improve their quality of life [2]. Among them, the Heilaohu [Kadsura coccinea (Lem.) A. C. Smith, Schisandraceae] fruit is a new taste, and its stems with their full aroma and sedative effect is used for pork and beef stew by the Li folk people [3]. The chemical constituents studied of this plant showed unique features in previous studies, and series of lignans [4], triterpenoids [5] and nor-terpenoids [6], with biological activities, were isolated [4,7]. To reveal the mechanism of action and explore new agents for health care, we studied K. coccinea stems (collected from the Li folk area) and found two new compounds, named kadsuricoccins A and B, and three known compounds: (22Z,24E)-3-oxoprotosta-27 12,22,24-trien-26-oic acid (3)[8], cycloartenone (4)[9] and 24-methyl-8-lanoten-3-one (5)[10] (Figure1). We then tested their AChE inhibit activities to search for natural material in preventing Alzheimer’s Disease (AD). The isolation process, new compounds’ structural elucidation details and the AChE inhibit assay, were described in this paper. Molecules 2019, 24, 3628; doi:10.3390/molecules24193628 www.mdpi.com/journal/molecules Molecules 2019, 24, 3628 2 of 7 Figure 1. The structures of compounds 1–5. 2. Results and Discussion Kadsuricoccins A (1) was isolated as colorless, amorphous powder. Its molecular formula of + C23H34O3 was determined by the positive HRESIMS ion at m/z 381.2508 [M + Na] (calcd. for C23H34O5Na, 381.2508), indicative of seven degrees of unsaturation. The IR spectrum revealed the 1 1 presence of carbonyl (1,712 and 1,691 cm− ) and double bonds (1,623 and 1,344 cm− ) absorptions. 1 The H-NMR spectra (Table1) of compound 1 exhibited signals of one methoxyl [δH 3.69 (3H, s, -OMe)], four methyls [δH 1.18 (3H, s, H-18), 0.90 (3H, s, H-19), 1.82 (3H, s, H-21) and 0.94(3H, s, H-22)], and three olefinic protons (δH 4.96 (1H, s, Ha-20), 4.84 (1H, s, Hb-20) and 6.65 (1H, dd, J = 3.4, 3.6 Hz, H-12). The 13C-NMR and DEPT spectroscopic data (Table1) showed 23 carbon resonances, including five methyls (one methoxyl), eight methylenes (one olefinic), three methines (one olefinic) and seven quaternary carbons (two carbonyl and two olefinic). By comparing the NMR, compound 1 was similar to those of 16-oxo-mansumbin-3(28),13(17)-dien-3-oic-acid methyl ester [11], a rare octanordammarane (a kind of octanary nor-triterpenoid) except for the markedly different shifts at δC 131.4 (d, C-12), 144.1 (s, C-13), 36.1 (t, C-16) and 207.1 (s, C-17), instead of δC 27.3 (t, C-12), 187.0 (s, C-13), 209.0 (s, C-16) and 126.5 (s, C-17) in 16-oxo-mansumbin-3(28),13(17)-dien-3-oic-acid methyl ester, indicating that compound 1 was generated from 16-oxo-mansumbin-3(28),13(17)-dien-3-oic-acid methyl ester for the α,β- unsaturated lactone moved from C-13-C-17-C(=O)-16 to C-12-C-13-C(=O)-17. Furthermore, 1 1 the determined molecular formula C15H22O4 and the key H- H COSY correlations with H-11 [δH 2.21 (2H, m)]/H-12, H-15[δH 1.99 (1H, m) and 1.54 (1.54)]/H-16 [δH 2.46 (1H, m) and 2.28 (1H, m)], and the HMBC correlations from H-12 to C-17 (δC 27.3 t) and C-10 (δC 37.7 s), and from H-15 and H-16 to C-17 verified this hypothesis. The other 1H-1HCOSY and HMBC correlations (Figure2) also confirmed this atom connectivity. The relative configuration of compound 1 was determined to be likely to the 16-oxo-mansumbin-3(28),13(17)-dien-3-oic-acid methyl ester (Figure2) with β-oriented of C-19, H-10 [11], and C-22, and α-oriented of H-5 and C-18 by ROESY cross-peaks H-2 [δH 2.29 (1H, m)]/H-5 [δH 2.18 (1H, m)], H-19/H-9 [δH 2.25 (1H, m)], H-9/H-22, H-22/H-7β [δH 2.08 (1H, m)], and H-7α [δH 1.17 (1H, m)]/H-18. Thus, the structure of compound 1 was assigned as shown, and named kadsuricoccins A (1). Molecules 2019, 24, 3628 3 of 7 Figure 2. Key 1H-1H COSY ( ), HMBC (H C), and ROESY ( ) correlations of 1–2. ! $ Table 1. 1H (500 MHz) and 13C nuclear magnetic resonance (NMR) (125 MHz) Data of Compounds 1–2. Compound 1 (in CDCl3) 2 (in CDCl3) No. δH mult. (J in Hz) δC δH mult. (J in Hz) δC 2.01 m 1.71 m 1 30.2 t 32.1 t 1.87 m 2.21 m 2.87 ddd, (7.2, 12.0, 2 2.29 m 30.3 t 14.8) 33.2 t 2.21 m 3 - 174.8 s - 221.6 s 4 - 147.0 s - 47.0 s 5 2.18 m 47.0 d 2.41 s 46.3 d 1.95 m 1.53 dd, (7.6, 12.9) 6 22.1 t 19.0 t 1.49 m 1.34 m 2.08 m 1.97 m 7 27.3 t 31.2 t 1.17 m 1.29 d, (6.3) 8 - 37.4 s - 37.5 s 9 2.25 m 41.2 d 2.40 m 46.9 d 10 37.7 s 35.6 s 11 2.21 m 24.7 t 6.27 dd, (2.9, 10.2) 121.5 d 12 6.65 dd, (3.4, 3.6) 131.4 d 5.59 d, (10.2) 126.6 d 13 - 144.1 s - 140.3 s 14 - 48.6 s - 55.1 s 1.99 m 15 26.8 t 2.43 m 27.8 t 1.54 m 2.46 m 16 36.1 t 1.38 m 28.6 t 2.28 m 17 - 207.1 s - 138.8 s 18 1.18 s 23.4 q 1.02 s 22.0 q 19 0.91 s 17.7 q 0.89 s 23.9 q 4.96 s 20 113.4 t 2.66 m 31.7 d 4.84 s 21 1.82 s 26.9 q 1.01 d, (7.6) 19.2 q 22 0.94 s 25.1 q 1.44 m 34.9 t 23/OMe 3.69 s 51.7 q 2.32 dd, (8.8, 16.5) 28.1 t 24 5.86 t, (7.2) 139.3 d 25 128.7 s 26 171.5 s 27 1.87 s 19.7 q 28 1.11 s 28.2 q 29 1.03 s 18.3 q 30 0.95 s 19.0 q Molecules 2019, 24, 3628 4 of 7 Kadsuricoccins B (2)’s molecular formula of C30H44O3 was determined by the positive HRESIMS + ion at m/z 475.3183 [M + Na] (calcd. for C23H34O5Na, 381.2508) with nine degrees of unsaturation. 1 1 The IR spectrum showed the presence of carbonyl (1705 cm− ) and double bonds (1457 and 1380 cm− ) absorptions. The 13C-NMR and DEPT spectroscopic data (Table1) revealed 30 carbon resonances, including seven methyls, eight methylenes, six methines (three olefinic), and nine quaternary carbons (one ketone, one acidic, and three olefinic). By comparing the NMR, compound 2 was similar to those of kadindutic acid [12], except for the markedly different shifts at δC 37.5 (s, C-8), 46.9 (d, C-9), 121.5 (d, C-11), 126.6 (d, C-12), 140.3 (s, C-13), 138.8 (s, C-17) and 19.0 (q, C-30), instead of δC 135.7 (d, C-8), 134.2 (s, C-8), 33.3 (t, C-11), 29.3 (d, C-12), 143.8 (s, C-13), 134.6 (s, C-17) and 21.5 (q, C-30) in kadindutic acid, indicating compound 2 was generated from kadindutic acid for the double bond moved from C-8-C-9 to C-11-C-12, and the methyl group 30-Me moved from C-12 to C-8.
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