Naturally Occurring Diarylheptanoids -A Supplementary Version

Records of Natural Products

Volumn 6, Issue 4, 2012, Pages 321-333

  Lv, Haining ^a   She, Gaimei ^a  

^a BEIJING UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

13C NMR spectral data; Diarylheptanoid; Natural products; Physiological activity

Indexed keywords

1,7 BIS(3,4 DIHYDROXYPHENYL)HEPTA DIEN 3 ONE; 1,76 BIS(4 HYDROXYPHENYL)HEPTA DIEN 3 ONE; 2,3,7 TRIHYDROXY 5 (3,4 DIHYDROXY STYRYL) 6,7,8,9 TETRAHYDRO 5H BENZOCYCLOHEPTENE; ALPHA TOCOPHEROL; BETULAPTOSIDE IA; CASSUMUNIN A; CASSUMUNIN B; CASSUMUNIN C; CURCUMIN; CYCLIC DIARYLHEPATANOID; DIARYLHEPATANOID; DIOSPONGIN B; DIOSPONGIN C; EPIHIRSUTANONOL; KATSUMAIN A; KATSUMAIN B; MISTLETONONE; MYRICANONE 17 O BETA DEXTRO (6 O GALLOYL) GLUCOPYRANOSIDE; MYRICANONE 5 O ALPHA LEVO ARABINOFURANOSYL (1-6) BETA DEXTRO GLUCOPYRANOSIDE; NANAONE; NATURAL PRODUCT; NITIDONE A; NITIDONE B; OREGONOSIDE; OREGONOSIDE A; OREGONOSIDE B; PTEROCARINE; RUBANOL; SILIBININ; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALDER; ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOSTEOPOROTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; CANCER CELL CULTURE; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG RESEARCH; DRUG STRUCTURE; HELICOBACTER PYLORI; HUMAN; HUMAN CELL; IC 50; LIVER PROTECTION; MELANOGENESIS INHIBITORY ACTIVITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PLANT GENE; RAT; REVIEW;

EID: 84865353838     PISSN: None     EISSN: 13076167     Source Type: Journal    
DOI: None     Document Type: Review

References (72)

1. S. S. Joo, S. G. Kim, S. E. Choi, Y. B. Kim, H. Y. Park, S. J. Seo, Y. W. Choi, M. W. Lee and D. Lee (2009). Suppression of T cell activation by hirsutenone, isolated from the bark of Alnus japonica, and its therapeutic advantages for atopic dermatitis, Eur. J. Pharmacol. 614, 98-105.
2. C. S. Lee, E. Jang, Y. J. Kim, M. S. Lee, S. J. Seo and M. W. Lee (2010). Hirsutenone inhibits lipopolysaccharide-activated NF-kB-induced inflammatory mediator production by suppressing Toll-like receptor 4 and ERK activation, Int. Immunopharm. 10, 520-525.
3. Y. Masuda, H. Kikuzaki, M. Hisamoto and N. Nakatani (2004). Antioxidant properties of gingerol related compounds from ginger, BioFactors. 21, 293-296.
4. S. Çikrikçi, E. Mozioǧlu and H. Yilmaz (2008). Biological activity of curcuminoids isolated from Curcuma longa, Rec. Nat. Prod. 2, 19-24.
5. K. Yasukawa, Y. Sun, S. Kitanaka, N. Tomizawa, M. Miura and S. Motohashi (2008). Inhibitory effect of the rhizomes of Alpinia officinarum on TPA-induced inflammation and tumor promotion in two-stage carcinogenesis in mouse skin, J. Nat. Med. 62, 374-378.
6. J. M. Han, W. S. Lee, J. R. Kim, J. Son, K. H. Nam, S. C. Choi, J. S. Lim and T. S. Jeong (2007). Effects of diarylheptanoids on the tumor necrosis factor-α-induced expression of adhesion molecules in human umbilical vein endothelial cells, J. Agric. Food Chem. 55, 9457-9464.
7. J. Ishida, M. Kozuka, H. Tokuda, H. Nishino, S. Nagumo, K. H. Lee and M. Nagai (2002). Chemopreventive potential of cyclic diarylheptanoids, Bioor. Med. Chem. 10, 3361-3365.
8. J. Ishida, M. Kozuka, H. K. Wang, T. Konoshima, H. Tokuda, M. Okuda, M. X. Yang, H. Nishino, N. Sakurai, K. H. Lee and M. Nagai (2000). Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis, Cancer Lett. 159, 135-140.
9. C. S. Lee, H. H. Ko, S. J. Seo, Y. W. Choi, M. W. Lee, S. C. Myung and H. Bang (2009). Diarylheptanoid hirsutenone prevents tumor necrosis factor-α-stimulated production of inflammatory mediators in human keratinocytes through NF-kB inhibition, Int. Immunopharmacol. 9, 1097-1104.
10. H. Ohtsu, H. Itokawa, Z. Xiao, C. Y. Su, C. C. Y. Shih, T. Chiang, E. Chang, Y. F. Lee, S. Y. Chiu, C. Chang and K. H. Lee (2003). Antitumor agents 222. Synthesis and anti-androgen activity of new diarylheptanoids, Bioor. Med. Chem. 11, 5083-5090.
11. S. Intapad, A. Suksamrarn and P. Piyachaturawat (2009). Enhancement of vascular relaxation in rat aorta by phytoestrogens from Curcuma comosa Roxb. Vascul. Pharmacol. 51, 284-290.
12. W. Winuthayanon, K. Suksen, C. Boonchird, A. Chuncharunee, M. Ponglikitmongkol, A. Suksamrarn and P. Piyachaturawat (2009). Estrogenic activity of diarylheptanoids from Curcuma comosa Roxb. Requires metabolic activation, J. Agric. Food Chem. 57, 840-845.
13. M. Takahashi, H. Fuchino, S. Sekita and M. Satake (2004). In vitro Leishmanicidal activity of some scarce natural products, Phytother. Res. 18, 573-578.
14. L. V. Alves, M. M. do Canto-Cavalheiro, L. Cysne-Finkelstein and L. Leon (2003). In vitro antiproliferative effects of several diaryl derivatives on Leishmania spp, Biol. Pharm. Bull. 26, 453-456.
15. L. V. Alves, L. Cysne-Finkelstein, R. M. Temporal, M. S. Genestra and L. L. Leon (2004). An effective diaryl derivative against Leishmania amazonensis and its infl{ligature}uence on the parasite X macrophage interaction, J. Enzym. Inhib. Med. Chem. 19, 437-439.
16. H. Akazawa, T. Akihisa, Y. Taguchi, N. Banno, R. Yoneima and K. Yasukawa (2006). Melanogenesis inhibitory and free radical scavenging activities of diarylheptanoids and other phenolic compounds from the bark of Acer nikoense, Biol. Pharm. Bull. 29, 1970-1972.
17. S. M. Cho, Y. M. Kwon, J. H. Lee, K. H. Yon and M. W. Lee (2002). Melanogenesis inhibitory activities of diarylheptanoids from Alnus hirsuta Turcz in B16 mouse melanoma cell, Arch. Pharm. Res. 25, 885-888.
18. H. Matsuda, S. Nakashima, Y. Oda, S. Nakamura, M. Yoshikawa (2009). Melanogenesis inhibitors from the rhizomes of Alpinia offi{ligature}cinarum in B16 melanoma cells, Bioor. Med. Chem. 17, 6048-6053.
19. S. D. Park, J. H. Jung, H. W. Lee, Y. M. Kwon, K. H. Chung, M. G. Kim and C. H. Kim (2005). Zedoariae rhizoma and curcumin inhibits platelet-derived growth factor-induced proliferation of human hepatic myofibroblasts, Int. Immunopharmacol. 5, 555-569.
20. 1) Potent protective effects of sesquiterpenes and curcumin from zedoariae rhizoma on liver injury induced by Dgalactosamine/lipopolysaccharide or tumor necrosis factor-α, Biol. Pharm. Bull. 25, 627-631.
21. M. A. Lee, H. K. Lee, S. H. Kim, Y. C. Kim and S. H. Sung (2010). Chemical constituents of Alnus firma and their inhibitory activity on lipopolysaccharide-induced nitric oxide production in BV2 microglia, Planta Med. 76, 1007-1010.
22. P. Claeson, P. Tuchinda and V. Reutrakul (1994). Naturally occurring 1,7-diarylheptanoids, J. Indian Chem. Soc. 71, 509-521.
23. G. M. Keserü and M. Nógrádi (1995). The chemistry of natural diarylheptanoids, Stud. Nat. Prod. Chem. 17, 357-394.
24. P. Claeson, U. P. Claeson, P. Tuchinda and V. Reutrakul (2002). Occurrence, structure and bioactivity of 1,7-diarylheptanoids, Stud. Nat. Prod. Chem. 26, 881-908.
25. H. Lv and G. She (2010). Naturally occurring diarylheptanoids, Nat. Prod. Commun. 5, 1687-1708.
26. A. Aragao-Craveiro, A. Dacosta-Prado, O. R. Gottlieb and P. C. Welerson-Albuquerque (1970). Diarylheptanoids of Centrolobium species, Phytochemistry 9, 1869-1875.
27. J. Yin, K. Kouda, Y. Tezuka, Q. L. Tran, T. Miyahara, Y. J. Chen and S. Kadota (2004). New diarylheptanoids from the rhizomes of Dioscorea spongiosa and their antiosteoporotic activity, Planta Med. 70, 54-58.
28. L. V. Alegrio, R. Braz-Filho and O. R. Gottlieb (1989). Diarylheptanoids and isoflavonoids from Centrolobium species, Phytochemistry. 28, 2359-2362.
29. H. Matsuda, A. Ishikado, N. Nishida, K. Ninomiya, H. Fujiwara, Y. Kobayashi and M. Yoshikawal (1998). Hepatoprotective, superoxide scavenging, and antioxidative activities of aromatic constituents from the bark of Betula platyphylla var. japonica, Bioorg. Med. Chem. Lett. 8, 2939-2944.
30. J. Li, F. Zhao, M. Z. Li, L. X. Chen and F. Qiu (2010). Diarylheptanoids from the rhizomes of Curcuma kwangsiensis, J. Nat. Prod. 73, 1667-1671.
31. H. Jiang, B. N. Timmermann and D. R. Gang (2007). Characterization and identifi{ligature}cation of diarylheptanoids in ginger (Zingiber offi{ligature}cinale Rosc.) using high-performance liquid chromatography/electrospray ionization mass spectrometry, Rapid Commun. Mass Spectrom. 21, 509-518.
32. G. Li, J. M. Cui, Y. Kwon, C. S. Seo, C. S. Lee, M. H. Woo, E. S. Lee, Y. Jahng, H. W. Chang, S. H. Lee and J. K. Son (2005). Two new diarylheptanoids from Juglans mandshurica, Bull. Korean Chem. Soc. 26, 1878-1880.
33. K. Machida, A. Suzuki, Y. Yogiashi and M. Kikuchi (2008). Studies on the constituents of Juglans species. II. New diarylheptanoids from the bark of Juglans mandshurica Maxim. var. siebolidiana Makino, J. Tohoku Pharm. University 55, 41-46.
34. K. Akiyama, H. Kikuzaki, T. Aoki, A. Okuda, N. H. Lajis and N. Nakatani (2006). Terpenoids and a diarylheptanoid from Zingiber ottensii, J. Nat. Prod. 69, 1637-1640.
35. H. Wohlmuth, M. A. Deseo, D. J. Brushett, D. R. Thompson, G. MacFarlane, L. M. Stevenson and D. N. Leach (2010). Diarylheptanoid from Pleuranthodium racemigerum with in vitro prostaglandin E2 inhibitory and cytotoxic activity, J. Nat. Prod. 73, 743-746.
36. Q. F. Tao, Y. Xu, R. Y. Y. Lam, B. Schneider, H. Dou, P. S. Leung, S. Y. Shi, C. X. Zhou, L. X. Yang, R. P. Zhang, Y. C. Xiao, X. Wu, J. Stöckigt, S. Zeng, C. H. K. Cheng and Y. Zhao (2008). Diarylheptanoids and a monoterpenoid from the rhizomes of Zingiber offi{ligature}cinale: Antioxidant and cytoprotective properties, J. Nat. Prod. 71, 12-17.
37. Y. C. Zeng F. Qiu, Y. Liu, G. X. Qu and X. S. Yao (2007). Isolation and identification of phase 1 metabolites of demethoxycurcumin in rats, Drug Metab. Dispos. 35, 1564-1573.
38. N. H. Tung, J. C. Ra, D. H. Sohn and Y. H. Kim (2010). A new diarylheptanoid from the bark of Alnus japonica, J. Asian Nat. Prod. Res. 12, 921-924.
39. R. F. Gonzalez-Laredo, R. F. Helm, J. Chen and J. J. Karchesy (1998). Two acylated diarylheptanoid glycosides from red alder bark, J. Nat. Prod. 61, 1292-1294.
40. S. S. Lee, S. C. Chen, C. K. Chen, C. H. Chen and C. M. Kuo (2006). Chemical constituents from Alnus formosana Burk. II. Polar constituents from the leaves, Nat. Prod. Commun. 1, 461-464.
41. L. Zhao, W. Qu, J. Q. Fu and J. Y. Liang (2010). A new diarylheptanoid from the rhizomes of Alpinia officinarum. Chin. J. Nat. Med. 8, 241-243.
42. H. Jiang, B. N. Timmermann and D. R. Gang (2006). Use of liquid chromatography-electrospray ionization tandem mass spectrometry to identify diarylheptanoids in turmeric (Curcuma longa L.) rhizome, J. Chromatogr. A 1111, 21-31.
43. Y. Sun, K. Tabata, H. Matsubara, S. Kitanaka, T. Suzuki and K. Yasukawa (2008). New cytotoxic diarylheptanoids from the rhizomes of Alpinia officinarum, Planta Med. 74, 427-431.
44. N. H. Tung, S. K. Kim, J. C. Ra, Y. Z. Zhao, D. H. Sohn and Y. H. Kim (2010). Antioxidative and hepatoprotective diarylheptanoids from the bark of Alnus japonica, Planta Med. 76, 626-629.
45. B. B. Zhang, Y. Dai, Z. X. Liao and L. S. Ding (2010). Three new antibacterial active diarylheptanoids from Alpinia offi{ligature}cinarum, Fitoterapia 81, 948-952.
46. I. N. Siddiqui, V. U. Ahmad, A. Zahoor, A. Ahmed, S. S. Khan, A. Khan and Z. Hassan (2010). Two new diarylheptanoids from Alnus nitida, Nat. Prod. Commun. 5, 1787-1788.
47. H. Kikuzaki, Y. Kawai and N. Nakatani (2001). 1,1-Diphenyl-2-picrylhydrazyl radical-scavenging active compounds from greater cardamom (Amomum subulatum Roxb.), J. Nutr. Sci. Vitaminol. 47, 167-171.
48. S. Y. Park and D. S. H. L. Kim (2002). Discovery of natural products from Curcuma longa that protect cells from Beta-Amyloid insult: A drug discovery effort against Alzheimer's disease, J. Nat. Prod. 65, 1227-1231.
49. H. Mohamad, N. H. Lajis, F. Abas, A. M. Ali, M. A. Sukari, H. Kikuzaki and N. Nakatani (2005). Antioxidative constituents of Etlingera elatior, J. Nat. Prod. 68, 285-288.
50. S. Athamaprasangsa, U. Buntrarongroj, P. Dampawan, N. Ongkavoranan, V. Rukachaisirikul, S. Sethijinda, M. Sornnarintra, P. Sriwub and W. C. Taylor (1994). A 1,7-diarylheptanoid from Alpinia conchigera, Phytochemistry. 37, 871-873.
51. P. Kamnaing, A. Tsopmo, E. A. Tanifum, M. H. K. Tchuendem, P. Tane, J. F. Ayafor, O. Sterner, D. Rattendi, M. M. Iwu, B. Schuster and C. Bacchi (2003). Trypanocidal diarylheptanoids from Aframomum letestuianum, J. Nat. Prod. 66, 364-367.
52. W. Li, S. Wang, J. Feng, Y. Xiao, X. Xue, H. Zhang, Y. Wang and X. Liang (2009). Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa, Magn. Reson. Chem. 47, 902-908.
53. N. An, L. Z. Xu, Z. M. Zou and S. L. Yang (2006). Diarylheptanoids from Alpinia officinarum, J. Asian Nat. Prod. Res. 8, 637-641.
54. T. Masuda, J. Isobe, A. Jitoe and N. Nakatani (1992). Antioxidative curcuminoids from rhizomes of Curcuma xanthorrhiza, Phytochemistry. 31, 3645-3647.
55. T. Masuda, A. Jitoe and N. Nakatani (1993). Structures of cassumunin A, B, and C, new potent antioxidants from Zingiber cassumunar, Chem. Lett., 189-192.
56. A. Jitoe, T. Masuda and T. J. Mabry (1994). Novel antioxidants, cassumunarin A, B, and C, from Zingiber cussumuntzr, Tetrahedron Lett. 35, 981-984.
57. H. Yao, G. X. Zhou, Q. Wu, G. Q. Lei, D. F. Chen, J. K. Chen and T. S. Zhou (2007). Mistletonone, a novel antioxidative diarylheptanoid from the branches and leaves of Viscum coloratum, Molecules. 12, 312-317.
58. W. S. He, X. Y. Wei, L. Li, Y. Li, S. Y. Guo and B. J. Guo (2001). A new antioxidant cyclic diarylheptanoid from the rhizomes of Zingiber officinale, Acta Bot. Sin. 43, 757-759.
59. K. Yamada, S. K. Nabeta, M. Yamasaki, K. Katakura and H. Matsuura (2009). Isolations of antibabesial compounds from Brucea javanica, Curcuma xanthorrhiza, and Excoecaria cochinchinensis, Biosci. Biotechnol. Biochem. 73, 776-780.
60. M. Sekiguchi, H. Shigemori, A. Ohsaki and J. Kobayashi (2002). Renealtins A and B, new diarylheptanoids with a tetrahydrofuran ring from the seeds of Renealmia exaltata, J. Nat. Prod. 65, 375-376.
61. Y. Y. Li, G. X. Chou and Z. T. Wang (2010). New diarylheptanoids and kavalactone from Alpinia katsumadai Hayata, Helv. Chim. Acta. 93, 382-388.
62. M. W. Lee, T. Takashi, N. Gen-Ichiro and N. Itsuo (1992). Hirsunin, an ellagitannin with a diarylheptanoid moiety, from Alnus hirsuta var. Microphylla, Phytochemistry. 31, 967-970.
63. D. S. Jang, E. J. Park, M. E. Hawthorne, J. S. Vigo, J. G. Graham, F. Cabieses, B. D. Santarsiero, A. D. Mesecar, H. H. S Fong, R. G. Mehta, J. M. Pezzuto and A. D. Kinghorn (2002). Constituents of Musa × paradisiaca Cultivar with the potential to induce the phase II enzyme, quinone reductase, J. Agric. Food Chem. 50, 6330-6334.
64. T. Sasaya (1985). Diarylheptanoids of Alnus hirsuta Turcz. (Betulaceae), Research Bulletins of the College Experiment Forests. 42, 191-205.
65. H. Akazawa, Y. Fujita, N. Banno, K. Watanabe, Y. Kimura, A. Manosroi, J. Manosroi and T. Akihisa (2010). Three new cyclic diarylheptanoids and other phenolic compounds from the bark of Myrica rubra and their melanogenesis inhibitory and radical scavenging activities, J. Oleo Sci. 59, 213-221.
66. H. B. Liu, C. B. Cui, B. Cai, Q. Q. Gu, D. Y. Zhang, Q. C. Zhao and H. S. Guan (2005). Pterocarine, a new diarylheptanoid from Pterocarya tonkinesis, its cell cycle inhibition at G0/G1 phase and induction of apoptosis in HCT-15 and K562 cells, Chin. Chem. Lett. 16, 215-218.
67. N. Sakurai, Y. Yaguchi, T. Hirakawa, M. Nagai and T. Inoue (1991). Two myricanol glycosides from Myrica rubra and revision of the structure of isomyricanone, Phytochemistry. 30, 3077-3079.
68. N. Watanabe, T. Sasaya and Y. Sano (1994). Extractives of the genus Corylus. III. Novel diarylheptanoids from the wood of Corylus sieboldiana Blume (2), Mokuzai Gakkaishi. 40, 1219-1225.
69. Y. Sawa, T. Sasaya and S. Ozawa (1988). Extractives of the genus Carpinus. I. Diarylheptanoids of sawashiba Carpinus cordata Blume wood, Mokuzai Gakkaishi. 34, 162-168.
70. N. Watanabe and T. Sasaya (1994). Extractives of the genus Corylus. II. Novel diarylheptanoids from the wood of Corylus sieboldiana Blume (1), Mokuzai Gakkaishi. 40, 199-203.
71. D. Y. Wang and E. G. Liu (2008). A new diaryheptanoid from the bark of Myrica rubra, Nat. Prod. Res. 22, 292-295.
72. L. J. Zeng, L. H. Chen and L. S. Liu (2009). A new diarylheptanoid from the bark of Myrica nana, J. Chem. Res. 40, 337-338.