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Α-Tetralonyl Glucosides from the Green Walnut Husks of Juglans Mandshurica and Their Antiproliferative Effects

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Α-Tetralonyl Glucosides from the Green Walnut Husks of Juglans Mandshurica and Their Antiproliferative Effects Published online: 2019-01-28 Rapid Communications α-Tetralonyl Glucosides from the Green Walnut Husks of Juglans mandshurica and Their Antiproliferative Effects Authors An-dong Wang1, 3,Chao-jieXie1,3, Yun-qiang Zhang 1, 3,Mei-chenLi1, 3, Xia Wang 1, 3,Jian-yuLiu2, 3, Yong-nan Xu2, 3 Affiliations Correspondence 1 School of Traditional Chinese Medicine, Shenyang Prof. Yong-nan Xu ʼ Pharmaceutical University, Shenyang, People s Republic School of Pharmaceutical Engineering, Shenyang Pharma- of China ceutical University 2 School of Pharmaceutical Engineering, Shenyang Pharma- Wenhua Road 103, Shenyang, Liaoning 110016, ʼ ceutical University, Shenyang, People s Republic of China Peopleʼs Republic of China 3 Key Laboratory of Structure-Based Drug Design & Phone:+8613342452898 Discovery, Ministry of Education, Shenyang Pharmaceuti- [email protected] cal University, Shenyang, Peopleʼs Republic of China Supporting information available online at Key words http://www.thieme-connect.de/products Juglans mandshurica, Juglandaceae, in vitro, α‑tetralonyl glucosides, antiproliferative ABSTRACT received September 13, 2018 Two new α-tetralonyl glucosides, (4S)-4,5,8-trihydroxy-α-tet- revised January 1, 2019 ralone-5-O-β-D-glucopyranosyl(1 → 6)-β-D-glucopyranoside accepted January 5, 2019 (1)and(4S)-4,8-dihydroxy-α-tetralone-4-O-β-D-glucopyrano- syl(1 → 6)-β-D-glucopyranoside (2), together with eight Bibliography known compounds (3–10) were isolated from the green wal- DOI https://doi.org/10.1055/a-0832-2328 nut husks of Juglans mandshurica. The structural characteriza- Published online January 28, 2019 | Planta Med 2019; 85: tion of all compounds was performed by spectroscopic analy- – 335 339 © Georg Thieme Verlag KG Stuttgart · New York | ses, including 1D and 2D NMR and HR‑ESI‑MS experiments. ‑ ISSN 0032 0943 The isolated compounds were assayed for their cytotoxicity against two human cancer cell lines, A549 and HeLa. Four Correspondence compounds (7–10) exhibited inhibitory effects against two Dr. Jian-yu Liu human cancer cell lines with GI values between 1.3 and School of Pharmaceutical Engineering, Shenyang Pharma- 50 5.8 µM. ceutical University Wenhua Road 103, Shenyang, Liaoning 110016, Peopleʼs Republic of China Phone:+8615998827142 [email protected] This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. Introduction In the course of our studies on the genus Juglans,including J. mandshurica, we have analyzed the chemical content of the Juglans, a genus of the family Juglandaceae, comprises about 20 green walnut husks of J. mandshurica. In particular, our attention species mainly distributed in the temperate and subtropical re- has been focused towards the n-butanol-soluble fraction of the gions of the northern hemisphere, extending into South America 70% ethanol extract containing naphthoquinone and diaryl- [1]. Juglans mandshurica Maxim. grows in the north of China in the heptanoid components. This study led us isolate ten compounds Heilongjiang, Jilin, Liaoning, Hebei, and Shanxi Provinces [2]. Pre- including two new α-tetralonyl glucosides, (4S)-4,5,8-trihydroxy- vious phytochemical studies of J. mandshurica led to the identifica- α-tetralone-5-O-β-D-glucopyranosyl(1 → 6)-β-D-glucopyranosie tion of naphthoquinones, diarylheptanoids, and flavonoids (as (1)and(4S)-4,8-dihydroxy-α-tetralone-4-O-β-D-glucopyranosyl well as their glycosides) [3–5]. The biological screening of these (1 → 6)-β-D-glucopyranoside (2), and a series of known com- compounds showed promising bioactivity, including cytotoxic pounds (3–10), some of which have not been reported before and antimicrobial activities [5–9]. from J. mandshurica (▶ Fig. 1). These compounds were screened Wang A et al. α-Tetralonyl Glucosides from … Planta Med 2019; 85: 335–339 335 Rapid Communications for antiproliferative activity against two human cancer cell lines, A549 and HeLa. Herein, details of the isolation, structural elucida- tion, and antiproliferative activities of these compounds are de- scribed. Results and Discussion The 70% ethanol extract of the dried the green walnut husks of J. mandshurica was subjected to multiple chromatographic steps over silica gel, Sephadex LH-20, and recycling preparative HPLC. Ten compounds were obtained, including two new compounds, (4S)-4,5,8-trihydroxy-α-tetralone-5-O-β-D-glucopyranosyl (1 → 6)-β-D-glucopyranoside (1)(4S)-4,8-dihydroxy-α-tetralone- 4-O-β-D-glucopyranosyl(1 → 6)-β-D-glucopyranoside (2), and eight known compounds comprising of four naphthoquinones ▶ Fig. 1 Chemical structures of compounds 1–10 from the green (3–6) and four diarylheptanoids (7–10). The structures of 1–10 walnut husks of J. mandshurica. were identified by physical data analyses, including 1D and 2D NMR and HR‑ESI‑MS. The sugar residues were identified by GC analyses after hydrolysis. Constituents 1 and 2 are new α-tetralonyl glucosides never de- scribed before in the literature. The full assignments of 1HNMR and 13C NMR spectroscopic data of the new isolated compounds (1 and 2) are listed. Their key 1H-1H COSY and HMBC correlations are presented in ▶ Fig. 2. The respective NMR and HR‑ESI‑MS spectra are provided in the Supporting Information. Compound 1 was obtained as a white amorphous powder. The molecular formula of C22H30O14 was determined on the basis of the HR‑ESI‑MS (m/z 541.1524, [M + Na]+). Acidic hydrolysis of 1 gave D-glucose as the mono sugar residue. The 1HNMRand13C ▶ Fig. 2 The key 1H‑1H COSY and HMBC of compounds 1–2. NMR data of 1 exhibited signals arising from a CO group at δC 206.5, a benzene ring at δH 7.60 (1H, d, J = 9.0 Hz, H-6), 6.93 (1H, d, J = 9.0 Hz, H-7), two β-glucopyranosyl moieties [anomeric gave D-glucose as the mono sugar residue. The 1HNMRand13C H-atom at δH 4.83 (1H, d, J =7.7Hz,H-1′), 4.40 (1H, d, J =7.7Hz, NMR data of 2 exhibited the signals arising from a CO group at H-1″) and C-atom signals at δC 104.8 (C-1″), 104.2 (C-1′), 78.0 (C- δC 206.6, a benzene ring at δH 7.53 (1H, t, J =8.4Hz,H-6),7.21 3″), 77.9 (C-3′), 77.8 (C-5″), 77.4 (C-5′), 75.2 (C-2′), 75.1 (C-2″), (1H, d, J = 7.4 Hz, H-5), 6.92 (1H, dd, J = 8.4, 1.0 Hz, H-7), two β- 71.6 (C-4″), 71.3 (C-4′), 70.0 (C-6′), and 62.7 (C-6″)]. These NMR glucopyranosyl moieties [anomeric H-atom at δH 4.47 (1H, d, characteristics resembled those observed for 3 [10]. However, in- J =7.8Hz,H-1″), 4.39 (1H, d, J =7.7Hz,H-1′)] and C-atom signals stead of a β-glucopyranosyl moiety in 3, compound 1 had two β- at δC 105.1 (C-1″), 102.7 (C-1′), 78.1 (C-5″), 78.0 (C-3′), 78.0 (C- glucopyranosyl moieties in view of the anomeric H-atom at δH 3″), 77.1 (C-5′), 75.2 (C-2′), 75.1 (C-2″), 71.7 (C-4″), 71.6 (C-4′), 4.83 (1H, d, J =7.7Hz,H-1′), 4.40 (1H, d, J =7.7Hz,H-1″). The 70.1 (C-6′), and 62.8 (C-6″). These NMR characteristics resembled linkage of the second sugar moiety at OH‑C(6′) of the first sugar those observed for 4 [12].However,insteadofaβ-glucopyranosyl moiety was established from the HMBC correlations between δH moiety in 4, compound 2 had two β-glucopyranosyl moieties in 4.40 (1H, d, J =7.7Hz,H-1″)andδC 70.0 (C-6′). The absolute con- view of the anomeric H-atom at δH 4.47 (1H, d, J =7.8Hz,H-1″), This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. figuration of the saccharides was determined to be D-glucose by 4.39 (1H, d, J =7.7Hz,H-1′). The linkage of the second sugar moi- GC analysis of chiral derivatives in the hydrolysate of this com- ety at OH‑C(6′) of the first sugar moiety was established from the pound. As for the absolute configuration of the chiral carbon, HMBC correlations between δH 4.47 (1H, d, J =7.8Hz,H-1″)and (4S)-1 was determined on the basis of a negative Cotton effect at δC 70.1 (C-6′). The absolute configuration of the saccharides was ca. 220–240 nm in the CD spectrum of 1 (Fig. 2S, Supporting In- determined to be D-glucose by GC analysis of the chiral deriva- 20 formation) and comparison of its optical rotation ([α]D : − 45 in tives in the hydrolysate of this compound. As for the absolute con- MeOH) with that of literature [11]. figuration of the chiral carbon, (4S)-2 was determined on the basis After further comprehensive analysis of its NMR spectra of a negative Cotton effect at ca. 210–230 nm in the CD spectrum (Figs. 3S–8S, Supporting Information), compound 1 was identi- of 2 (Fig. 10S, Supporting Information) and comparison of its op- 20 fied as (4S)-4,5,8-trihydroxy-α-tetralone-5-O-β-D-glucopyranosyl tical rotation ([α]D : − 51 in MeOH) with that of the literature [11]. (1 → 6)- β-D-glucopyranoside. After further comprehensive analysis of its NMR spectra Compound 2 was obtained as a white amorphous powder. The (Figs. 11S–16S, Supporting Information), compound 2 was identi- molecular formula of C22H30O13 was determined on the basis of fied as (4S)-4,8-dihydroxy-α-tetralone-4-O-β-D-glucopyranosyl the HR‑ESI‑MS (m/z 525.1563, [M + Na]+). Acidic hydrolysis of 2 (1 → 6)- β-D-glucopyranoside.
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