Cytotoxic Diarylheptanoids from the Pericarps of Walnuts (Juglans regia)

Abstract

Two new diarylheptanoids, juglanin A (1) and B (2), together with 15 known compounds, were isolated from the extract of the seed husks of walnuts (Juglans regia L.). The structures of 1 and 2 were elucidated by various spectroscopic methods including intensive 2D-NMR techniques, HR-ESI-MS, and X-ray single-crystal diffraction analysis, and the cytotoxic activities of 1, 2, and 10 against human hepatoma (Hep G2) cells was reported.

Key words

Juglans regia L. - Juglandaceae - diarylheptanoids - cytotoxic activity

References

• 1 Lee S W, Lee K S, Son J K. New naphthalenyl glycosides from the roots of Juglans mandshurica.  Planta Med. 2000;  66 184-6
• 2 Lee K S, Li G, Kim S H, Lee C S, Woo M H, Lee S H. Cytotoxic diarylheptanoids from the roots of Juglans mandshurica.  J Nat Prod. 2002;  65 1707-8
• 3 Li G, Xu M L, Choi H G, Lee S H, Jahng Y D, Lee C S. Four new diarylheptanoids from the roots of Juglans mandshurica.  Chem Pharm Bull. 2003;  51 262-4
• 4 Kim S H, Lee K S, Son J K, Je G H, Lee J S, Lee C H. Cytotoxic compounds from the roots of Juglans mandshurica.  J Nat Prod. 1998;  61 643-5
• 5 Talapapatra S K, Karmacharya B, De S C, Talapatra B. (-)-Regiolone, an α-tetralonoe from Juglans regia: structure, stereochemistry and conformation.  Phytochemistry. 1988;  27 3929-32
• 6 Machida K, Matsuoka E, Kasahara T, Kikuchi M. Studies on the constituents of Juglans species. I. structural determination of (4S)- and (4 R)-4-hydroxy-α-trtralone derivative from the fruit of Juglans mandshurica Maxim. var. sieboldiana Makino.  Chem Pharm Bull. 2005;  53 934-7
• 7 Li H R, Yang Z G, Wang J, Kitanaka S. Naphthoquinones from twigs of walnut (Juglans regia) and their inhibition on nitric oxide synthesis.  Nat Prod Res Dev. 2006;  18 363-5
• 8 Binder R G, Benson M E, Flath R A. Eight 1,4-naphthoquinones from Juglans.  Phytochemistry. 1989;  28 2799-801
• 9 Buttery R G, Light D M, Nam Y, Nam Y, Merrill G B, Roitman J N. Volatile compounds of green walnut husks.  J Agric Food Chem. 2000;  48 2858-61
• 10 Sheldrick G M. SHELX-97, Program for crystal structure refinement. Göttingen; University of Gottingen 1997
• 11 Thabrewa M I, Mitryb R R, Morsyb M A, Hughes R D. Cytotoxic effects of a decoction of Nigella sativa, Hemidesmus indicus and Smilax glabra on human hepatoma HepG2 cells.  Life Sci. 2005;  77 1319-30
• 12 Morihara M, Sakurai N, Inoue T, Kawai K I, Nagai M. Two novel diarylheptanoid glucosides from Myrica gale var. tomentosa and absolute structure of plane-chiral galleon.  Chem Pharm Bull. 1997;  45 820-3
• 13 Okuda T, Yoshida T, Hatano T, Koga T, Toh N, Kuriyama K. Circular dichroism of hydrolysable tannins-I ellagitannins and gallotannins.  Tetrahedron Lett. 1982;  23 3937-40
• 14 Jiang Z H, Tanaka T, Inutsuka C, Kouno I. Alkaloids, diarylhepyanoid and naphthalene carboxylic acid ester from Rhoiptelea chiliantha.  Chem Pharm Bull. 2001;  49 737-40
• 15 Tene M, Wabo H K, Kamnaing P, Tsopmp A, Tane P. Diarylheptanoids from Myrica arborea.  Phytochemistry. 2000;  54 975-8
• 16 Takeda Y, Fujita T, Shingu T, Ogimi C. Studies on the bacterial gall of Myrica rubra: isolation of anew [7.0]-Metacyclophan from the gall and dl-β-phenyllactic acid from the culture of gall-forming bacteria.  Chem Pharm Bull. 1987;  35 2569-73
• 17 Joshi B S, Pelletier W. Extensive 1D, 2 D NMR spectra of some [7.0] metacyclophanes and X-ray analysis of (±)-myricanol.  J Nat Prod. 1996;  59 759-64
• 18 Begley M J, Campbell R VM, Crombie L. Constitution and absolute configuration of meta,meta-bridged, strained biphenyls from Myrica nagi; X-ray analysis of 16-bromomyricanol. J Chem Soc C 1971: 3634-42
• 19 Reynoids W F, Mclean S, Poplawski J, Enriquez R G. Total assignment of ¹³C and ¹H spectra of three isomeric triterpenol derivatives by 2 D NMR: an investigation of the potential utility of ¹H chemical shifts in structural investigations of complex natural products.  Tetrahedron. 1986;  42 3419-28
• 20 Reiko T, Miyako T, Shunyo M. Triterpenes from the stem bark of Phyllanthus flexuosus.  Phytochemistry. 1988;  27 3563-7
• 21 Zhu W M, Shen Y M, Hong X, Zuo G Y, Yang X S, Hao X J. Triterpenoids from the Dai medicinal plant Winchia calophylla.  Acta Bot Sin. 2002;  44 354-6
• 22 Li J, Bi Z M, Xiao Y J, Li P. Studies on triterpenoid saponins from Achyranthese bidentata BI.  Chin Pharm J. 2007;  42 178-80
• 23 Morota T, Yang C X, Sasaki H, Qin W Z. Triterpenes from Tripterigium wilfordii.  Phytochemistry. 1995;  39 1153-7
• 24 Lien J C, Huang L, Teng C M, Wang J P, Kuo S C. Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents.  Chem Pharm Bull. 2002;  50 672-4
• 25 Liu J X, Di D L, Li C, Huang X Y. Regiolone from the pericarps of Juglans regia L.  Acta Cryst (E). 2007;  63 O2713-4
• 26 Liu L J, Li W, Koike K, Zhang S J, Nikaido T. New α-tetralonyl glucosides from the fruit of Juglans mandshurica.  Chem Pharm Bull. 2004;  52 566-9
• 27 Arima S, Yamada Y, Takeda K, Takayanagl H, Harigaya Y. Synthesis of cis- and trans-5,8-dihydroxy-5,6,7,8-tetrahydro- 1,4-naphthoquinone.  Chem Pharm Bull. 2001;  49 340-2
• 28 Cong Y, Wang J H, Guo H R, Li X. Isolation and identification of the chemical constituents of Leonurus japonicus Houtt.  Chin J Med Chem. 2003;  56 349-52
• 29 Luo Y M, Liu A H, Yu B W, Kang L J, Huang L Q. Studies on chemical constituents of Sarcandra glabra.  Chin Pharm J. 2005;  40 1296-8
• 30 Takagi S, Shiono R, Rosenstein R D. The crystal and molecular structure of 1,2 : 4,5-di-O-isopropylidene-β-D-fructopyranose.  Acta Cryst (B). 1973;  29 1177-86
• 31 Kang J, Lim G J, Yoon S K, Kim M Y. Asymmetric cyclopropanation using new chiral auxiliaries derived from D-fructose.  J Org Chem. 1995;  60 564-77