Planta Med 2019; 85(04): 335-339
DOI: 10.1055/a-0832-2328
Biological and Pharmacological Activity
Rapid Communications
Georg Thieme Verlag KG Stuttgart · New York

α-Tetralonyl Glucosides from the Green Walnut Husks of Juglans mandshurica and Their Antiproliferative Effects

An-dong Wang
1   School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Chao-jie Xie
1   School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Yun-qiang Zhang
1   School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Mei-chen Li
1   School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Xia Wang
1   School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Jian-yu Liu
2   School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
,
Yong-nan Xu
2   School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
3   Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 13 September 2018
revised 01 January 2019

accepted 05 January 2019

Publication Date:
28 January 2019 (online)

Abstract

Two new α-tetralonyl glucosides, (4S)-4,5,8-trihydroxy-α-tetralone-5-O-β-D-glucopyranosyl(1 → 6)-β-D-glucopyranoside (1) and (4S)-4,8-dihydroxy-α-tetralone-4-O-β-D-glucopyranosyl(1 → 6)-β-D-glucopyranoside (2), together with eight known compounds (3 – 10) were isolated from the green walnut husks of Juglans mandshurica. The structural characterization of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR and HR-ESI-MS experiments. The isolated compounds were assayed for their cytotoxicity against two human cancer cell lines, A549 and HeLa. Four compounds (7 – 10) exhibited inhibitory effects against two human cancer cell lines with GI50 values between 1.3 and 5.8 µM.

Supporting Information

 
  • References

  • 1 Lin H, Zhang YW, Bao YL, Wu Y, Sun LG, Yu CL, Huang YX, Wang EB, Li YX. Secondary metabolites from the stem bark of Juglans mandshurica . Biochem Syst Ecol 2013; 51: 184-188
  • 2 Editorial Committee of Flora of China, Chinese Academy of Sciences. Flora of China, Vol. 21. Beijing: Science Press; 1979: 31-33
  • 3 Liu JX, Di DL, Wei XN, Han Y. Cytotoxic diarylheptanoids from the pericarps of walnuts (Juglans regia). Planta Med 2008; 74: 754-759
  • 4 Zhao H, Bai H, Jing Y, Li W, Yin S, Zhou H. A pair of taxifolin-3-O-arabinofuranoside isomers from Juglans regia L. Nat Prod Res 2016; 31: 945-950
  • 5 Yu HY, Zhang XQ, Li X, Zeng FB, Ruan HL. 2-methoxyjuglone induces apoptosis in HepG2 human hepatocellular carcinoma cells and exhibits in vivo antitumor activity in a H22 mouse hepatocellular carcinoma model. J Nat Prod 2013; 76: 889-895
  • 6 Guo LN, Zhang R, Guo XY, Cui T, Dong W, Huo JH, Wang WM. Identification of new naphthalenones from Juglans mandshurica and evalution of their anticancer activities. Chin J Nat Medicines 2015; 13: 707-710
  • 7 Yu HY, Li X, Meng FY, Pi HF, Zhang P, Ruan HL. Naphthoquinones from the root barks of Juglans cathayensis dode. J Asian Nat Prod Res 2011; 13: 581-587
  • 8 Jin M, Sun J, Li R, Diao S, Zhang C, Cui J, Son JK, Zhou W, Li G. Two new quinones from the roots of Juglans mandshurica . Arch Pharm Res 2016; 39: 1237-1241
  • 9 Li J, Xu KP, Zou ZX, Zou H, Long HP, Tan LH, Liu RH, Wang YK, Xu PS, Tan GS. Two new compounds from the green peel of Juglans mandshurica . J Asian Nat Prod Res 2017; 19: 1087-1092
  • 10 Liu L, Li W, Koile K, Zhang S, Nikado T. New α-tetralonyl glucosides from the fruit of Juglans mandshurica . Chem Pharm Bull 2004; 52: 566-569
  • 11 Machida K, Matsuoka E, Kasahara T, Kikuchi M. Studies on the constituents of Juglans species. I. Structural determination of (4S)- and (4R)-4-hydroxy-a-tetralone derivatives from the fruit of Juglans mandshurica MAXIM. var. sieboldiana MAKINO. Chem Pharm Bull 2005; 53: 934-937
  • 12 Fujimoto H, Nagano J, Yamaguchi K, Yamazaki M. Immunosuppressive components from an Ascomycete, Diplogelasinospora grovesii . Chem Pharm Bull 1998; 46: 423-429
  • 13 Talapatra S, Karmacharya B, Talapatra B. (−)-Regilone, an α-tetralone from Juglans Regia: structure, stereochemistry and conformation. Phytochemistry 1988; 27: 3929-3932
  • 14 Jin W, Cai X, Na M, Lee J, Bae K. Triterpenoids and diarylheptanoids from Alnus hirsuta inhibit HIF-1 in AGS cells. Arch Pharm Res 2007; 30: 412-418
  • 15 Yao D, Jin M, Zhang C, Luo J, Li R, Zheng M, Cui J, Li G. A new phenolic glycoside from Juglans mandshurica . Nat Prod Res 2014; 28: 998-1002
  • 16 Lv H, She G. Naturally occurring diarylheptanoids – a supplementary version. Rec Nat Prod 2012; 6: 321-333
  • 17 Alberti A, Riethmuller E, Beni S. Characterization of diarylheptanoids: an emerging class of bioactive natural products. J Pharmaceut Biomed 2018; 147: 13-34
  • 18 Uto T, Tung NH, Appiah OR, Aning A, Morinaga O, Edoh D, Nyarko AK, Shoyama Y. Antiproliferative and pro-apoptotic activity of diarylheptanoids isolated from the bark of Alnus japonica in human leukemia cell lines. Am J Chinese Med 2015; 43: 757-767
  • 19 Tian Z, An N, Zhou B, Xiao P, Kohane IS, Wu E. Cytotoxic diarylheptanoid induces cell cycle arrest and apoptosis via increasing ATF3 and stabilizing p53 in SH-SY5Y cells. Cancer Chemother Pharmacol 2009; 63: 1131-1139
  • 20 Lai YC, Chen CK, Lin WW, Lee SS. A comprehensive investigation of anti-inflammatory diarylheptanoids from the leaves of Alnus formosana . Phytochemistry 2012; 73: 84-94
  • 21 Yang Y, Kinoshita K, Koyama K. Structure-antiemetic-activity of some diarylheptanoids and their analogues. Phytomedicine 2002; 9: 146-152