Spectral Characteristics of Cyclic Diarylheptanoids

Abstract

Abstract:

Structural and spectral characteristics of the cyclic diarylheptanoids were reviewed. The UV, IR and NMR characteristics of cyclic diarylheptanoids were summarized, as well as the methods used to determine the absolute configuration of these compounds. It was shown that natural cyclic diarylheptanoids have different structural characteristics, particularly the H-6 of cyclic diphenyl ether diarylheptanoids. This work will provide a basic reference for studying the structure of the cyclic diarylheptanoids.

Key words: NMR, spectral characteristics, cyclic diarylheptanoids, review, mosher method

CLC Number:

ZHANG Yi, LIU Yi, MENG Da-Li, LI Xian. Spectral Characteristics of Cyclic Diarylheptanoids[J]. Chinese Journal of Magnetic Resonance, 2010, 27(4): 669-677.

References

[1] Li Ning (李宁)，Zhang Peng(张鹏)，Liang Dong(梁东), et al. NMR characterization of 7-oxo-aporphine alkaloids(7-氧代阿朴菲型生物碱的NMR研究)[J]. Chinese J Magn Reson(波谱学杂志)，2009，26(1): 103-110. 

[2] Li Ning(李宁)，Zhang Peng(张鹏)，Xiao Wan(肖婉), et al. NMR characterization of agrimophol-a phloroglucinol derivative(间苯三酚类化合物-鹤草酚的NMR研究) [J]. Chinese J Magn Reson(波谱学杂志)，2009，26(3): 400-407. 

[3] Liu Z G，Ji S，Zhang Y C，et al. Myricarborin a and n-butyl-α-L-rhamnopyranoside, two novel compounds from the bark of myrica rubra[J]. New Product Communications，2009，4(4): 513-516.

[4] Liu Hong-xing(刘红星), Ma Xiao-hong(马小红)，Huang Chu-sheng(黄初升). Research in naturally occurring biphenyl and diphenyl ethertype diarylheptanoids(天然大环二芳基庚烷类化合物的研究概况)[J]. Nat Prod Res Dev(天然产物研究与开发)，2008，20: 172-179.

[5] Wu Li-jun(吴立军). Organic Chemistry of Natural Products(实用天然产物有机化学)[M]. Beijing(北京)： People's Medicinal Publishing House(人民卫生出版)，2007.

[6] Seiji N, Sumiko I, Masahiro N, et al. Study on the constituents of aceraceae plants. Ⅷ.Diarylheptanoids and other phenolics from acernikoense[J]. Chem Pharm Bull，1996，44(5): 1 086-1 089.

[7] Venkatraman G，Mishra A K，Thombare P S，et al. Diarylheptanoids from garuga pinnata[J]. Phytochem，1993，33(5): 1 221-1 225.

[8] Vanimireddy L N R，Kodelar，Masuni S，et al. Two new macrocyclic diaryl ether heptanoids from boserllia ovalifoliolata[J]. Chem Pharm Bull，2003，51(9): 1 081-1 084.

[9] Wang Su-juan(王素娟)，Pei Yue-hu(裴月湖). Diarylheptanoids from leaves of Betula platyphylla(白桦叶中的二苯基庚烷类化合物)[J]. Chinese Traditional and Herbal Drugs(中草药)，2001，32 (2): 99-101.

[10] Thoshio M，Jing T，Iwao T，et al. Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from japanese folk medicine acer nikoense[J]. J Nat Prod，2003，66: 86-91.

[11] Seiji N，Morihiro K，Takao I，et al. Study on the constituents of aceraceae plants. Ⅺ. Two types of Cyclic Diarylheptanoid from Acer nikoense[J]. Chem Pharm Bull，1993，41(7): 1 255-1 257.

[12] Jun X L，Duo L D，Xin Y H，et al. Two new diarylheptanoids from the pericarps of Juglansregia L[J]. Chinese Chemical Letters，2007，18: 943-946.

[13] Kulsum A，Rahman A M，Choudhury M，et al. Macrocyclic diarylheptanoids from Garuga pinnata[J]. Phytochemistry，2006，67: 2 659-2 662.

[14] Hiroyuki F，Soh K，Tetsuya S，et al. Chemical evaluation of betula species in JapanⅡ. Constituents of betula platyphylla var. japonica
[J]. Chem Pharm Bull，1996，44(5): 1 033-1 038.

[15] Motohiko M，Nobuko S，Takao I，et al. Two novel diarylheptanoid glucosides from myrica gale Var. tomentosa and absolute structure of plane-chiral galeon[J]. Chem Pharm Bull，1997，45(5): 820-823.

[16] Takashi T，Zhi H J，Jiang，et al. Distribution of ellagic acid derivatives and diarylheptanoids in wood of platycarya strobilacea[J]. Phytochemistry，1998，47(5): 851-854.

[17] Fujinorri H，Motoo S，Yoshioki H. Heartwood constituents of betula maximowicziana[J]. Phytochemistry，1997，45(3): 589-595.

[18] Kaneda N，Kinghorn A D，Farnsworth N R，et al. Two diarylheptanoids and a lignan from casuatrina junghuhniana[J]. Phytochemistry， 1990，29(10): 3 366-3 368.

[19] Balawant S J，William S P，Newton M G，et al. Extensive 1D, 2D NMR spectra of some[7.0] metacyclophanes and X-ray analysis of (±)-myricanol[J]. J Nat Prod，1996，59: 759-764.

[20] Jing T，Toshio M，Iwao T，et al. Inhibitors of nitric oxide production from the bark of myrica rubra: structures of new biphenyl type diarylheptanoids glycosides and taraxerane type triterpene[J]. Bioorganic & Medicinal Chemistry，2002，10: 4 005-4 012.

[21] Junfeng W，Shahsa D，Yuehu W，et al. Cyclic diarylheptanoids from myrica nana inhibiting nitric oxide release[J]. Bioorganic & Medicinal Chenistry，2008，16: 8 510-8 515.

[22] Masahiro N，Junko D，Motohiko M，et al. Diarylheptanoids fron myrica galee var.tomentoda and revised structure of porson[J]. Chem Pharm Bull，1995，43(10): 1 674-1 677.

[23] Ioanna K，Constantions V，Jasmin J，et al. Cymodienol and cymodiene:new cytotoxic diarylheptanoids from the sea grass cymodocea nodosa[J]. Tetrahedron Lett，2005，46: 2 845-2 847.

[24] Hiroyuki F，Tetsuya S，Nobutoshi T. Chemical evaluation of betula species in Japan. Ⅲ. Constituents of betula maximowicziana[J]. Chem Pharm Bull，1996，44(9): 1 748-1 753.

[25] Zhi H J，Takashi T，Haruko，et al. Three diarylheptanoids from rhoiptelea chiliantha[J]. Phytochemistry，1996，43(5): 1 049-1 054.

[26] Ji S L，Hyoung J K，Hokoon P，et al. New diarylheptanoids from the stems of carpinus cordata[J]. J Nat Prod，2002，65: 1 367-1 370.

[27] Ishida J, Kozuka M, Wang H K，et al. Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activity and two-stage mouse skin carcinogenesis[J]. Cancer Lett，2000，159(2): 135-140.

[28] Kontiza I，Vagias C，Jakupovic J，et al. Cymodienol and cymodiene: new cytotoxic diarylheptanoids from the sea grass Cymodocea nodosa[J]. Tetr Lett，2005，46(16): 2 845-2 847.

[29] Toshio M，Jing T，Iwao T，et al. Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense[J]. J Nat Prod，2003，66: 86-91.