Naturally occurring diarylheptanoids

Natural Product Communications

Volumn 5, Issue 10, 2010, Pages 1687-1708

  Lv, Haining ^a   She, Gaimei ^a  

^a BEIJING UNIVERSITY OF CHINESE MEDICINE   (China)

Author keywords

Diarylheptanoid; Natural products; Physiological activity

Indexed keywords

1 (4 HYDROXYPHENYL) 7 (4 HYDROXY 3 METHOXYPHENYL) 4E EN 3 HEPTANONE; 1 (4 HYDROXYPHENYL) 7 PHENYL 3,5 HEPTANEDIOL; 13 OXOMYRICANOL; 3,5 DIHYDROXY 1 (4 HYDROXY 3 METHOXYPHENYL) 7 PHENYL HEPTANE; 5 HYDROXY 7 (4 HYDROXY 3 METHOXYPHENYL) 1 (4 HYDROXYPHENYL) 3 HEPTANONE; 5 HYDROXY 7 (4 HYDROXYPHENYL) 1 PHENYL 3 HEPTANONE; 7 (3,4 DIHYDROXYPHENYL) 1 (4 HYDROXY 3 METHOXYPHENYL) 4 EN 3 HEPTANONE; BLEPHAROCALYXIN D; BLEPHAROCALYXIN E; CURCUMIN; CURCUMIN I; CURCUMIN II; CURCUMIN III; CYMODIENOL; DEOXYCYMODIENOL; GALEON; HEPTANE DERIVATIVE; HIRSUTANONE; ISOCYMODIENE; KATSUMADAIN A; KATSUMADAIN B; MYRICANONE; PAPYRIFEROSIDE A; PLATYPHYLLENONE; PLATYPHYLLONOL; PLATYPHYLLONOL 5 O BETA XYLOPYRANOSIDE; PLATYPHYLLOSIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; YAKUCHINONE A; YAKUCHINONE B;

ALDER; ALPINIA; ANTIBACTERIAL ACTIVITY; ANTIEMETIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BARK; CARBON NUCLEAR MAGNETIC RESONANCE; CURCUMA LONGA; ESTROGEN ACTIVITY; GINGER; HUMAN; HUMAN CELL; PLANT ROOT; REVIEW; RHIZOME;

ALNUS; ALPINIA; CURCUMA; ZINGIBER;

EID: 77957913256     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1000501035     Document Type: Review

References (137)

1. Vogel E, Pelletier S. (1815) Curcumin. Journal of Pharmaceutics, 2, 50-54.
2. Milobedzka J, Kostanecki SV, Lampe V. (1910) Curcumin. Berichte der Deutschen Chemischen Gesellschaft, 43, 2163-2170.
3. Srinivasan KR. (1953) A chromatographic study of the curcuminoids in Curcuma longa Linn. Journal of Pharmacy and Pharmacology, 5, 448-453.
4. Asakawa Y, Genjida F, Hayashi S, Matsuura T. (1969) A new ketol from Alnus firma Sieb. et Zucc. Tetrahedron Letters, 38, 3235-3257.
5. Asakawa Y. (1970) Chemical constituents of Alnus firma (Betulaceae). I. Phenyl propane derivatives isolated from Alnus firma. Bulletin of the Chemical Society of Japan, 43, 2223-2229.
6. Asakawa Y. (1972) Chemical constituents of Alnus firma (Betulaceae). III. The synthesis and stereochemistry of yashabushiketols. Bulletin of the Chemical Society of Japan, 45, 1794-1797.
7. Asakawa Y. (1970) A new ketol, 1,7-diaryl-5-hydroxy-3-heptanone, and trans-stilbene from Alnus firma Sieb, et Zucc. (Betulaceae). Bulletin of the Chemical Society of Japan, 43, 575.
8. Suga T, Asakawa Y, Iwata N. (1971) 1,7-Diphenyl-1,3-heptadien-5-one. New ketone from Alnus pendula (Betulaceae). Chemistry & Industry, 766.
9. Badreldin HA, Husnia M, Salwa AN, Amel OB, Gerald B. (2006) Some biological properties of curcumin: a review. Natural Product Communications, 1, 509-521.
10. Cheng AL, Hsu CH, Lin JK, Hsu JK, Ho YF, Shen TS, Ko JY, Lin JT, Lin BR, Wu MS, Yu HS, Jee SH, Chen GS, Chen TM, Chen CA, Lai MK, Pu YS, Pan MH, Wang YJ, Tsai CC, Hsieh CY. (2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Research, 21, 2895-2900.
11. NCI (http://www.cancer.gov/clinicaltrials/view-clinicaltrials.aspx? version=patient&cdrid=67916&clickitem=ClinicalTrialsSearchResult) Protocol IDs: CCUM-9941, NCI-P00-0144, UMN-9941. National Cancer Institute.
12. Claeson P, Tuchinda P, Reutrakul V. (1994) Naturally occurring 1,7-diarylheptanoids. Journal of Indian Chemical Society, 71, 509-521.
13. Claeson P, Claeson UP, Tuchinda P, Reutrakul V. (2002) Occurrence, structure and bioactivity of 1,7-diarylheptanoids. Studies in Natural Products Chemistry, 26 (Bioactive Natural Products (Part G)), 881-908.
14. Hashimoto T, Tori M, Asakawa Y. (1986) Five new diarylheptaniods from the male flowers of Alnus sieboldiana. Chemical and Pharmaceutical Bulletin, 34, 1846-1849.
15. Kuroyanagi M, Noro T, Fukushima S, Aiyama R, Ikuta A, Itokawa H, Morita M. (1983) Studies on the constituents of the seeds of Alpinia katsumadai Hayata. Chemical and Pharmaceutical Bulletin, 31, 1544-1550.
16. Luo XZ, Yu JG, Xu LZ, Li KM, Yan P, Feng JD. (2000) Studies on the chemical constituents of the fruits from Alpinia oxyphylla. Acta Pharmaceutica Sinica, 35, 204-207.
17. Shin D, Kinoshita K, Koyama K, Takahashi K. (2002) Antiemetic principles of Alpinia officinarum. Journal of Natural Products, 65, 1315-1318.
18. Uehara SI, Yasuda I, Akiyama K, Morita H, Takeya K, Itokawa H. (1987) Diarylheptanoids from the rhizomes of Curcuma xanthorrhiza and Alpinia officinarum. Chemical and Pharmaceutical Bulletin, 35, 3298-3304.
19. Araujo CAC, Alegrio LV, Leon LL. (1998) Antileishmanial activity of compounds extracted and characterized from Centrolobium sclerophyllum. Phyochemistry, 49, 751-754.
20. Akihisa T, Taguchi Y, Yasukawa K, Tokuda H, Akazawa H, Suzuki T, Kimura Y. (2006) Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor promoting effects. Chemical and Pharmaceutical Bulletin, 54, 735-739.
21. Morikawa T, Tao J, Ueda K, Mastuda H, Yoshikawa M. (2003) Medicinal foodstuffs. XXXI. Structures of new aromatic constituents and inhibitors of degranulation in RBL-2H3 cells from a Japanese folk medicine, the stem bark of Acer nikoense. Chemical and Pharmaceutical Bulletin, 51, 62-67. (Pubitemid 41702018)
22. Nagai M, Matsuda E, Inoue T, Fujita M, Chi HJ, Ando T. (1990) Studies on the contribution of Aceraceae plants. VII. Diarylheptaniods from Acer griseum and Acer triflorum. Chemical and Pharmaceutical Bulletin, 38, 1506-1508. (Pubitemid 20265617)
23. Smite E, Lundgren LN, Andersson R. (1993) Arylbutanoid and diarylheptanoid glycosides from inner bark of Betula pendula. Phytochemistry, 32, 365-369.
24. Paek D, Kim HJ, Jung SY, Yook CS, Jin C, Lee YS. (2010) A new diarylheptanoid glycoside from the stem bark of Alnus hirsuta and protective effects of diarylheptanoid derivatives in human HepG2 cells. Chemical and Pharmaceutical Bulletin, 58, 238-241.
25. Fuchino H, Konishi S, Satoh T, Yagi A, Saitsu K, Tatsumi T, Tanaka N. (1996) Chemical evaluation of Betula species in Japan. II. Constituents of Betula platyphylla var. japonica. Chemical and Pharmaceutical Bulletin, 44, 1033-1038. (Pubitemid 26194026)
26. Nagai M, Kenmochi N, Fujita M, Furukawa N, Inoue T. (1986) Studies on the constituents of Aceraceae plants. VI. Revised stereochemistry of (-)-centrolobol, and new glycosides from Acer nikoense. Chemical and Pharmaceutical Bulletin, 34, 1056-1060.
27. Mshvildadze V, Legault J, Lavoie S, Gauthier C, Pichette A. (2007) Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera. Phytochemistry, 68, 2531-2536. (Pubitemid 47451444)
28. +-glucose cotransporter (SGLT) inhibitors from Acer nikoense. Bioorganic and Medicinal Chemistry Letters, 20, 1070-1074.
29. Ali MS, Tezuka Y, Awale S, Banskota AH, Kadota S. (2001) Six new diarylheptanoids from the seeds of Alpinia blepharocalyx. Journal of Natural Products, 64, 289-293. (Pubitemid 32249789)
30. Wu FJ, Su JD. (1996) Isolation, purification and identification of antioxidative components from fruits of Amomum tsao-ko L. Journal of the Chinese Agriculture Chemical Society, 34, 438-451.
31. Nomura M, Tokoroyama T, Kubota T. (1981) Biarylheptanoids and other constituents from wood of Alnus japonica. Phytochemistry, 20, 1097-1104.
32. Zhou CX, Zhang XY, Dong XW, Tao QF, Dou H, Zhang RP, Huang KX, Li XK, Chen CX, Zeng S, Zhao Y. (2007) Three new diarylheptanoids and their antioxidant property. Chinese Chemical Letters, 18, 1243-1246.
33. Yokosuka A, Mimaki Y, Sakagami H, Sashida Y. (2002) New diarylheptanoids and diarylheptanoid glucosides from the Rhizomes of Tacca chantrieri and their cytotoxic activity. Journal of Natural Products, 65, 283-289. (Pubitemid 34260795)
34. Jiang ZH, Tanaka T, Hirata H, Fukuoka R, Kouno I. (1996) Three diarylheptanoids from Rhoiptelea chiliantha. Phytochemistry, 43, 1049-1054.
35. Li G, Seo CS, Lee SH, Jahng YD, Chang HW, Lee CS, Woo MH, Son JK. (2004) Diarylheptanoids from the roots of Juglans mandshurica. Bulletin of the Korean Chemical Society, 25, 397-399.
36. Ma J, Jin XL, Yang L, Liu ZL. (2004) Diarylheptanoids from the rhizomes of Zingiber officinale. Phytochemistry, 65, 1137-1143.
37. Kikuzaki H, Usuguchi J, Nakatani N. (1991) Constituents of Zingiberaceae. I. diaryheptanoids from the rhizomes of ginger (Zingiber officinale Roscoe). Chemical and Pharmaceutical Bulletin, 39, 120-122.
38. Kikuzaki H, Kobayashi M, Nakatani N. (1991) Diarylheptanoids from rhizomes of Zingiber officinale. Phytochemistry, 30, 3647-3651.
39. Yamahara J, Hatakeyama S, Taniguchi K, Kawamura M, Yoshikawa M. (1992) Stomachic principles in ginger. II. Pungent and anti-ulcer effects of low polar constituents isolated from ginger, the dried rhizoma of Zingiber officinale Roscoe cultivated in Taiwan. Yakugaku Zasshi, 112, 645-655.
40. Kaewamatawong R, Boonchoong P, Teerawatanasuk N. (2009) Diarylheptanoids from Curcuma comosa. Phytochemistry Letters, 2, 19-21.
41. Lee MW, Park MS, Jeong DW, Kim KH, Kim HH, Toh SH. (2000) Diarylheptanoids from the leaves of Alnus hirsuta Turcz. Archives of Pharmacal Research, 23, 50-53.
42. Kim HJ, Kim KH, Yeom SH, Kim MK, Shim JG, Lim HW, Lee MW. (2005) New diarylheptanoid from the barks of Alnus japonica Steudel. Chinese Chemical Letters, 16, 1337-1340. (Pubitemid 43872147)
43. Wada H, Tachibana H, Fuchino H, Tanaka N. (1998) Three new diarylheptaniod glycosides from Alnus japonica. Chemical and Pharmaceutical Bulletin, 46, 1054-1055. (Pubitemid 28363339)
44. Ngo KS, Geoffrey D. (1998) Stilbenes, monoterpenes, dirylheptanoids, labdanes and chalcones from Alpinia katsumadai. Phytochemistry, 47, 1117-1123.
45. Suksamrarn A, Ponglikitmongkol M, Wongkrajang K, Chindaduang A, Kittidanairak S, Jankam A, Yingyongnarongkul B, Kittipanumat N, Chokchaisiri R, Khetkam P, Piyachaturawat P. (2008) Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation. Bioorganic and Medicinal Chemistry, 16, 6891-6902.
46. Jurgens TM, Frazier EG, Schaeffer JM, Jones TE, Zink DL, Borris RP. (1994) Novel nematocidal agents from Curuma comosa. Journal of Natural Products, 57, 230-235.
47. Suksamrarn A, Eiamong S, Piyachaturawat P, Charoenpiboonsin J. (1994) Phenolic diarylheptanoids from Curcuma xanthorrhiza. Phytochemistry, 36, 1505-1508.
48. 13C-NMR studies on soliton model compounds. Journal of American Chemical Society, 112, 9519-9527.
49. Thiele G, Streitwieser A. (1994) Equilibrium acidities of some α, ω-diphenylpolyenes. Journal of American Chemical Society, 116, 446-454.
50. Sun Y, Matsubara H, Kitanaka S, Yasukawa K. (2008) Diarylheptanoids from the rhizomes of Alpinia officinarum. HeIvetica Chimica Acta, 91, 118-123.
51. Kiuchi F, shibuya M, Sankawa U. (1982) Inhibitors of prostaglandin from Alpinia officinarum. Chemical and Pharmaceutical Bulletin, 30, 2279-2282.
52. Hideji I, Makoto M, Susumu M. (1981) Two new diarylheptanoids from Alpinia officinarum Hance. Chemical and Pharmaceutical Bulletin, 29, 2383-2385.
53. Itokawa H, Morita H, Midorikawa I, Aiyama R, Morita M. (1985) Diaryheptanoids from the rhizome of Alpinia officinarum Hance. Chemical and Pharmaceutical Bulletin, 33, 4889-4893. (Pubitemid 16181327)
54. Hema PS, Nair MS. (2009) Flavonoids and other constituents from the rhizomes of Alpinia calcarata. Biochemical Systematics and Ecology, 37, 52-54.
55. Fan GJ, Kang YH, Han YN, Han BH. (2007) Platelet-activating factor (PAF) receptor binding antagonists from Alpinia officinarum. Bioorganic and Medicinal Chemistry Letters, 17, 6720-6722.
56. An N, Zhang HW, Xu LZ, Yang SL, Zou ZM. (2010) New diarylheptanoids from the rhizome of Alpinia officinarum Hance. Food Chemistry, 119, 513-517.
57. An N, Zou ZM, Tian Z, Luo XZ, Yang SL, Xu LZ. (2008) Diarylheptanoids from the rhizomes of Alpinia officinarum and their anticancer activity. Fitoterapia, 79, 27-31.
58. Tung NH, Kwon HJ, Kim JH, Ra JC, Ding Y, Kim JA, Kim YH. (2010) Anti-influenza diarylheptanoids from the bark of Alnus japonica. Bioorganic and Medicinal Chemistry Letters, 20, 1000-1003.
59. Ohta S, Koyama M, Aoki T, Suga T. (1985) Absolute configuration of platyphylloside and (-)-centrlobol. Bulletin of the Chemical Society of Japan, 58, 2423-2324.
60. Chen J, Gonzalez-Laredo RF, Karchesy JJ. (2000) Minor diarylheptanoid glycosides of Alnus rubra bark. Phytochemistry, 53, 971-973. (Pubitemid 30233134)
61. Kuroyanagi M, Shimomae M, Nagashima Y, Muto N, Okuda T, Kawahara N, Nakane T, Sano T. (2005) New diarylheptanoids from Alnus japonica and their antioxidative activity. Chemical and Pharmaceutical Bulletin, 53, 1519-1523. (Pubitemid 41744475)
62. Terazawa M, Koga T, Okuyama H, Miyake M. (1973) Isolation of platyphyllonol, a new diarylheptanoid from green bark of shirakanba,Betula platyphylla Sukatch. var. japonica Ham. Mokuzai Gakkaishi, 19, 47-48.
63. Li G, Xu ML, Choi HG, Lee SH, Jahng YD, Lee CS. (2003) Four new diarylheptanoids from the roots of Juglans mandshurica. Chemical and Pharmaceutical Bulletin, 51, 262-264.
64. Flynn DL, Rafferty MF, Bocter AM. (1986) Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally occurring diarylheptanoids: inhibitory activities of curcuminoids and yakuchinones. Prostaglandins Leukotrienes and Medicine, 22, 357-360.
65. Itokawa H, Aiyama R, Ikuta A. (1981) A pungent diaryl-heptanoids from Alpinia oxyphylla. Phytochemistry, 20, 769-771.
66. Jin WY, Cai XF, Na MK, Lee JJ, Bae KH. (2007) Triterpenoids and diarylheptanoids from Alnus hirsuta inhibit HIF-1 in AGS cells. Archives of Pharmacal Research, 30, 412-418.
67. Giang PM, Son PT, Matsunami K, Otsuka H. (2006) New diarylheptanoids from Amomum muricarpum Elmer. Chemical and Pharmaceutical Bulletin, 54, 139-140. (Pubitemid 43036770)
68. Chen J, Karchesy JJ, Gonzalez-Laredo RF. (1998) Phenolic diarylheptenones from Alnus rubra. Planta Medica, 64, 74-75.
69. Lee KS, Li G, Kim SH, Lee CS, Woo MH, Lee SH, Jhang YD, Son JK. (2002) Cytotoxic diarylheptanoids from the roots of Juglans mandshurica. Journal of Natural Products, 65, 1707-1708. (Pubitemid 35386813)
70. Li YX, Ruan HL, Zhou XF, Zhang YH, Pi HF, Wu JZ. (2008) Cytotoxic diarylheptanoids from pericarps of Juglans cathayensis Dode. Chemical Research in Chinese Universities, 24, 427-429.
71. Endo K, Kanno E, Oshima Y. (1990) Structures of antifungal diarylheptenones, gingerenones A, B, C and isogingerenone B, isolated from the rhizomes of Zingiber officinale. Phytochemistry, 29, 797-799.
72. Carmen MC, Miguel LL, Maria AA, Eduardo N, Juan T, Maria JA. (2001) A cytotoxic diarylheptanoid from Viscum cruciatum. Phytochemistry, 58, 567-569.
73. Dong H, Chen SX. (1998) A new antiplatelet diarylheptanoid from Alpinia blepharocalyx. Journal of Natural Products, 61, 142-144. (Pubitemid 28086996)
74. Wang LY, Zhang M, Zhang CF, Wang ZT. (2008) Diaryl derivatives from the root tuber of Curcuma longa. Biochemical Systematics and Ecology, 36, 476-480.
75. Nakayama R, Tamura Y, Yamanaka H, Kikuzaki H, Nakatani N. (1993) Two curcuminoid pigments from Curcuma domestica. Phytochemistry, 33, 501-502.
76. Kim JE, Kim AR, Chung HY, Han SY, Kim BS, Choi JS. (2003) In vitro peroxynitrite scavenging activity of diarylheptanoids from Curcuma longa. Phytotherapy Research, 17, 481-484.
77. Kiuchi F, Goto Y, Sugimoto N, Akao N, Kondo K, Tsuda Y. (1933) Nematocidal activity of surmerio synergistic action curcuminoids. Chemical and Pharmaceutical Bulletin, 41, 1640-1643.
78. Yang Y, Kinoshita K, Koyama K, Takahashi K, Tai T, Nunoura Y, Watanabe K. (1999) Two novel anti-emetic principles of Alpinia katsumadai. Journal of Natural Products, 62, 1672-1674. (Pubitemid 30030613)
79. Zhao Y, Tao QF, Zhang RP, Zhou CX, Dou H, Shi SY, Xiao YC, Sun LL, Zeng S, Huang KX, Zhang XD, Li XK. (2007) Two new compounds from Zingiber officinale. Chinese Chemical Letters, 18, 1247-1249.
80. Kikuzaki H, Nakatanit N. (1996) Cyclic diarylbeptanoids from Zingiber officinale. Phytochemistry, 43, 273-277.
81. Ali MS, Tezuka Y, Banskota AH, Kadota S. (2001) Blepharocalyxins C-E, three new dimeric-diarylheptanoids, and related compounds from the seeds of Alpinia blepharocalyx. Journal of Natural Products, 64, 491-496. (Pubitemid 32423876)
82. Prasain JK, Tezuka Y, Li JX, Tanaka K, Basnet P, Dong H, Namba T, Kadota S. (1999) New diarylheptanoid from the seeds of Alpinia blepharocalyx. Planta Medica, 65, 196-196.
83. Yin J, Liu ZH, Wang Y, Chen YJ, Shigetoshi K. (2006) The isolation and structure identification of two new diarylheptanoids from Dioscorea spongiosa. Modern Chinese Medicine, 8, 16-19.
84. Giang PM, Son PT, Matsunami K, Otsuka H. (2005) New diarylheptanoids from Alpinia pinnanensis. Chemical and Pharmaceutical Bulletin, 53, 1335-1337.
85. Prasain JK, Li JX, Tezuka Y, Tanaka K, Basnet P, Dong H, Namba T, Kadota S. (1998) Calyxin H, epicalyxin H, and blepharocalyxins A and B, novel diarylheptanoids from the seeds of Alpinia blepharocalyx. Journal of Natural Products, 61, 212-216. (Pubitemid 28136774)
86. Kumar PJ, Tezuka Y, Jian JL, Tanaka K, Basnet P, Dong H, Namba T, Kadota S. (1997) Six novel diarylheptanoids bearing chalcone or flavanone moiety from the seeds of Alpinia blepharocalyx. Tetrahedron, 53, 7833-7842. (Pubitemid 27239292)
87. Kadota S, Hui D, Basnet P, Prasain JK, Xu GJ, Namba T. (1994) Three novel diarylheptanoids, calyxin A, calyxin B, and 3-epi-calyxin B from a Chinese crude drug "Yunnan Cao Kou" (Alpinia blepharocalyx K. Schum.). Chemical and Pharmaceutical Bulletin, 42, 2647-2649.
88. Prasain JK, Tezuka Y, Li JX, Tanaka K, Basnet P, Dong H, Nambaa T, Kadota S. (1998) Novel diarylheptanoids from the seeds of Alpinia blepharocalyx: Revised structure of calyxin A. Journal of Chemical Research, (S) 22-23, (M) 265-279.
89. Tezuka Y, Gewali MB, Ali MS, Banskota AH, Kadota S. (2001) Eleven novel diarylheptanoids and two unusual diarylheptanoid derivatives from the seeds of Alpinia blepharocalyx. Journal of Natural Products, 64, 208-213. (Pubitemid 32198348)
90. Zhao L, Liang JY, Zhang JY, Chen Y. (2010) A novel diarylheptanoid bearing flavonol moiety from the rhizomes of Alpinia officinarum Hance. Chinese Chemical Letters, 21, 194-196.
91. Tezuka Y, Ali MS, Banskota AH, Kadota S. (2000) Blepharocalyxins C-E three novel antiproliferative diarylheptanoids from the seeds of Alpinia blepharocalyx. Tetrahedron Letters, 41, 5903-5907. (Pubitemid 30490648)
92. Kontiza I, Vagias C, Jakupovic J, Moreau D, Roussakis C, Roussis V. (2005) Cymodienol and cymodiene new cytotoxic diarylheptanoids from the sea grass Cymodocea nodosa. Tetrahedron Letters, 46, 2845-2847. (Pubitemid 40431751)
93. Kontiza I, Stavri M, Zloh M, Vagias C, Gibbons S, Roussis V. (2008) New metabolites with antibacterial activity from the marine angiosperm Cymodocea nodosa. Tetrahedron, 64, 1696-1702.
94. Kubo M, Nagai M, Inoue T. (1983) Studies on the constituents of Aceraceae plants. IV. Carbon-13 nuclear magnetic resonance spectra of acerogenin A, rhododendrol, and related compounds, and structure of aceroside IV from Acer nikoense. Chemical and Pharmaceutical Bulletin, 31, 1917-1922.
95. Morikawa T, Tao J, Toguchida I, Matsuda H, Yoshikawa M. (2003) Structures of new cyclic diarylheptanoids and inhibitors of nitric oxide production from Japanese folk medicine Acer nikoense. Journal of Natural Products, 66, 86-91. (Pubitemid 36150823)
96. Nagai M, Kubo M, Takahashi K, Fujita M, Inoue T. (1983) Studis on the constituents of Aceraceae plants. V. Two diaryheptaniod glycosides and an arylburanol apiosiylgucoside from Acer nikoense. Chemical and Pharmaceutical Bulletin, 31, 1923-1928.
97. Nagumo S, Ishizawa S, Nagai M, Nagumo S, Ishizawa S, Nagai M, Inoue T. (1996) Studies on the constituents of Aceraceae plants XIII. Diarylheptanoids and other phenolics from Acer nikoense. Chemical and Pharmaceutical Bulletin, 44, 1086-1089. (Pubitemid 26194028)
98. Wang JF, Zhang CL, Lu Q, Yu YF, Zhong HM, Long CL, Cheng YX. (2009) Three new diarylheptanoids from Myrica nana. HeIvetica Chimica Acta, 92, 1594-1599.
99. Fujinori H, Motoo S, Yoshioki H. (1997) Heartwood constituents of Betula maximowicziana. Phytochemistry, 45, 589-595.
100. Yu YF, Lu Q, Guo L, Mei RQ, Liang HX, Luo DQ, Cheng YX. (2007) Myricananne and Myricanandiol: Two new cyclic 'diarylheptanoids' from the roots of Myrica nana. HeIvetica Chimica Acta, 90, 1691-1696.
101. Tanaka T, Jiang ZH, Kouno I. (1998) Distribution of ellagic acid derivatives and a diarylheptanoid in wood of Platycarya strobilacea. Phytochemistry, 47, 851-854. (Pubitemid 28136895)
102. Liu JX, Meng M, Li C, Huang XY, Di DL. (2008) Simultaneous determination of three diarylheptanoids and an α-tetralone derivative in the green walnut husks (Juglans regia L.) by high-performance liquid chromatography with photodiode array detector. Journal of Chromatograph A, 1190, 80-85.
103. Jiang ZH, Tanaka T, Inutsuka C, Kouno I. (2001) Alkaloids, diarylheptanoid and naphthalene carboxylic acid ester from Rhoiptelea chiliantha. Chemical and Pharmaceutical Bulletin, 49, 737-740. (Pubitemid 32587122)
104. Malterud, KE, Anthonsen T, Hjortas J. (1976) 14-oxa-[7,1]-metapara- cyclophanes from Myrica gale L., a new class of natural products. Tetrahedron Letters, 17, 3069-3072.
105. Kim SH, Lee KS, Son JK, Je GH, Lee JS, Lee CH, Cheong CJ. (1998) Cytotoxic compounds from the roots of Juglans mandshurica. Journal of Natural Products, 61, 643-645.
106. Morohara M, Sakurai N, Inoue T, Kawai K, Nagai M. (1997) Two new diarylheptaniods glucosides from Myrica gale var. tomentosa and absolute structure of plane-chiral galleon. Chemical and Pharmaceutical Bulletin, 45, 820-823. (Pubitemid 27255095)
107. Wang JF, Dong SS, Wang YH, Lu Q, Zhong HM, Du GH, Zhang L, Cheng YX. (2008) Cyclic diarylheptanoids from Myrica nana inhibiting nitric oxide release. Bioorganic and Medicinal Chemistry, 16, 8510-8515.
108. Liu J, Di DL, Huang XY, Li C. (2007) Two new diarylheptanoids from the pericarps of Juglans regia L. Chinese Chemical Letters, 18, 943-946.
109. Lakshmi NRV, Ravinder K, Srinivasulu M, Venkateshwar GT, Malla RS, Srujankumar D, Prabhakar RT, Suryanarayana MU, Venkateswarlu Y. (2003) Two new macrocyclic diaryl ether heptanoids from Boswellia ovalifoliolata. Chemical and Pharmaceutical Bulletin, 51, 1081-1084. (Pubitemid 41701937)
110. Nagumo S, Kaji N, Inoue T, Nagai M. (1993) Studies on the constituents of Aceraceae plants. XI. Two types of cyclic diarylheptanoid from Acer nikoense. Chemical and Pharmaceutical Bulletin, 41, 1255-1257. (Pubitemid 23279404)
111. Venkatraman G, Mishra AK, Thombare PS, Sabata BK. (1993) Diarylheptanoids from Garuga pinnata. Phytochemistry, 33, 1221-1225.
112. Ara K, Rahman AH, Hasan CM, Iskander MN, Asakawa Y, Quang DN, Rashid MA. (2006) Macrocyclic diarylheptanoids from Garuga pinnata. Phytochemistry, 67, 2659-2662.
113. Mishra AK, Haribal MM, Sabata BK. (1985) Garuganin III, a macrocyclic biphenyl ether from Garuga pinnata. Phytochemistry, 24, 2463-2465.
114. Kalchhauser H, Krishnamurty HG. (1989) NMR spectral assignment and conformation of macrocyclic biaryl ethers from Garuga gamblei. Magnetic Resonance in Chemistry, 27, 635-639.
115. Fuchino H, Satoh T, Tanaka N. (1996) Chemical evaluation of Betula species in Japan. III. Constituents of Betula maximowicziana. Chemical and Pharmaceutical Bulletin, 44, 1748-1753. (Pubitemid 26342290)
116. Kaneda N, Kinghorn AD, Farnsworth NR, Tuchinda P, Udchachon J, Santisuki T, Reutrakul V. (1990) Two diarylheptanoids and a lignan from Casuarina junghuhniana. Phytochemistry, 29, 3366-3368.
117. Lee MW, Tanaka T, Nonaka GI, Hahn DR. (1992) Phenolic compounds on the leaves of Betula platyphylla var. latifolia. Archives of Pharmacal Research, 15, 211-214. (Pubitemid 23124607)
118. Wang DY, Liu EG, Feng YJ. (2008) A new diarylheptanoid from the bark of Myrica rubra. Chinese Chemical Letters, 19, 547-549.
119. Tene M, Wabo HK, Kamnaing P, Tsopmo A, Tane P, Ayafor JF, Sterner O. (2000) Diarylheptanoids from Myrica arborea. Phytochemistry, 54, 975-978.
120. Tao J, Morikawa T, Toguchida I, Ando S, Matsuda H, Yoshikawa M. (2002) Inhibitors of nitric oxide production from the bark of Myrica rubra structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpeney. Bioorganic and Medicinal Chemistry, 10, 4005-4012. (Pubitemid 36164699)
121. Takeda Y, Fujita T, Shingu T, Ogimi C. (1987) Studies on the bacterial gall Myrica rubra isolation of a new [7,0]-metacyclophan from the gall and DL-β-phenyllactic acid from the culture of gall-forming bacteria. Chemical and Pharmaceutical Bulletin, 35, 2569-2573.
122. Balawant S, JoshiS, Pelletier W. (1996) Extensive 1D, 2D NMR spectra of some [7.0]-metacyclophanes and X-ray analysis of (±)-myricanol. Journal of Natural Products, 59, 759-764.
123. Matsuda H, Morikawa T, Tao J, Ueda K, Yoshikawa M. (2002) Bioactive constituents of chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute atereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra. Chemical and Pharmaceutical Bulletin, 50, 208-215. (Pubitemid 41694582)
124. Inoue T, Arai Y, Nagai M. (1984) Diarlheptanoids in the bark of Myrica rubra Sieb. et Zucc. Yakugaku Zasshi, 104, 37-41. (Pubitemid 14150530)
125. Yaguchi Y, Sakurai N, Nagai M, Inoue T. (1988) Constituents of Myrica rubra III. Structures of two glycosides of myricanol. Chemical and Pharmaceutical Bulletin, 36, 1419-1424.
126. Sasaya T, Sawa Y, Ozawa S. (1989) Extractives of genus Carpinus II. Diarylheptanoids of sawashiba, Carpinus cordata Blume, wood (2). Mokuzai Gakkaishi, 35, 36-41.
127. Nagai M, Dohi J, Morohara M, Sakurai N. (1995) Diaryheptaniods from Myrica gale var. tomentosa and revised structure of porson. Chemical and Pharmaceutical Bulletin, 43, 1674-1677.
128. Lee JS, Kim HJ, Park H, Lee YS. (2002) New diarylheptanoids from the stems of Carpinus cordata. Journal of Natural Products, 65, 1367-1370.
129. Malterud KE, Anthonsen T. (1980) 13-oxomyricanol, a new [7,0]-metacyclophane from Myrica nagi. Phytochemistry, 19, 705-707.
130. Moritami Y. (1965) The chemistry of wood extractives. IX. The structure of asadanin (1). Mokuzai Gakkaishi, 11, 146-157.
131. Fuchino H, Satoh T, Shimizu M, Tanaka N. (1988) Chemical evaluation of Betula spcies in Japan. IV. Constituents of Betula davurica. Chemical and Pharmaceutical Bulletin, 46, 166-168.
132. Guo H, Li BG, Wu ZJ, Zhang GL. (2006) Lupane triterpenoids and a diarylhenpoid from Clematoclethra actinidioides. Planta Medica, 72, 180-183. (Pubitemid 43293875)
133. Chun KS, Sohn Y, Kim HS, Kim OH, Park KK, Lee JM, Lee J, Lee JY, Moon A, Lee SS, Surh YJ. (1999) Anti-tumor promoting potential of naturally occurring diarylheptanoids structurally related to curcumin. Mutation Research, 428, 49-57. (Pubitemid 29389676)
134. Ishida J, Kozuka M, Wang HK, Konoshima T, Tokuda H, Okuda M, Mou XY, Nishino H, Sakurai N, Lee KH, Nagai M. (2000) Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. Cancer Letters, 159, 135-140.
135. Yang Y, Kinoshita K, Koyama K, Takahashi K, Kondo S, Watanabe K. (2002) Structure-antiemetic-activity of some diarylheptanoids and their analogues. Phytomedicine, 9, 146-152. (Pubitemid 34297370)
136. Kurzer MS, Xu X. (1997) Dietary phytoestrogens. Annual Review of Nutrition, 17, 353-381.
137. Winuthayanon W, Piyachaturawat P, Suksamrarn A, Ponglikitmongkol M, Arao Y, Hewitt SC, Korach KS. (2009) Diarylheptanoid phytoestrogens isolated from the medicinal plant Curcuma comosa: biologic actions in vitro and in vivo indicate estrogen receptor-dependent mechanisms. Environmental Health Perspectives, 117, 1155-1161.