Acetylenic terrestrial anticancer agents

Natural Product Communications

Volumn 1, Issue 5, 2006, Pages 405-429

  Dembitsky, Valery M ^a   Levitsky, Dmitri O ^b  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITÉ DE NANTES   (France)

Author keywords

Acetylenic; Anticancer; Bacteria; Cytotoxic; Fungi; Metabolites; Plants; Polyacetylenes

Indexed keywords

EID: 33845306165     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0600100512     Document Type: Review

References (295)

1. (a) Lam J, Breteler H, Arnason A, Hansen H. (Eds). (1988) Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds, Elsevier, Amsterdam, pp. 366;
2. (b) Sarker SD, Nahar L. (2004) Natural medicine: the genus Angelica. Current Medicinal Chemistry, 11, 1479-1500;
3. (c) Ross RAM. (1972) Natural acetylenes of special biosynthetic interest. Phytochemistry, 11, 221-227
4. (d) Krishna V, Gupta GS, Singh P. (1999) Acetylenic derivatives from some Compositae plants. Journal of the Indian Chemical Society, 76, 689-691.
5. (a) Tyrrell D. (1969) Biochemical systematics and fungi. Botanical Review, 35, 305-316;
6. (b) Bu'Lock JD. (1966) Biosynthesis of polyacetylenes in fungi. Biosynthesis of Antibiotics, 1, 141-157;
7. (c) Bu'Lock, JD. (1966) Biogenesis of natural acetylenes. Complementary Phytochemistry, 79-95;
8. (d) Johnson, AW. (1965) Polyacetylenic compounds in nature. Endeavour, 24, 126-130.
9. (a) Herbst P. (1996) The alkyne acids from fungi. Planta Medica, 8, 394-402;
10. (b) McAfee BJ, Taylor A. (1999) A review of the volatile metabolites of fungi found on wood substrates. Natural Toxins, 7, 283-303;
11. (c) Paiz L, Lopez, I, Rodriguez E. (1989) Chemistry and distribution of bioactive polyacetylenes in Asteraceae. Revista Latinoamericana de Quimica, 20, 120-125.
12. (a) Dembitsky VM, Tolstikov GA, Tolstikov AG. (2003) Natural halogenated polyacetylenides. Chemistry of Sustainable Development (Russia), 11, 341-348;
13. (b) Nie B, Lu Y, Chen Z. (2002) Progress in studies on naturally occurring polyacetylenes. Zhongcaoyao (China), 33, 1050-1053;
14. (c) Whitehead R. (1999) Natural product chemistry. Annual Reports on the Progress of Chemistry, 95B, 183-205.
15. (a) Parr AJ. (1989) The production of secondary metabolites by plant cell cultures. Journal of Biotechnology, 10, 1-26;
16. (b) Cosio EG, Towers GHN, Norton RA, Rodriguez E. (1988) Polyacetylenes. Phytochemicals in plant cell cultures. Cell Cultured Somatic Cell and Genetic Plants, 5, 495-508;
17. (c) Schulte KE. (1979) Occurrence of polyacetylenes - chemistry and biosynthesis. Saengyak Hakhoechi, 9, 11-32;
18. (d) Shulte KE. (1979) Occurrence of polyacetylenes in plants. Chemistry and biosynthesis. Eastern Pharmacist, 22, 85-99.
19. (a) Panter KE. (2005) Natural toxins of plant origin. In:USDA ARS Poisonous Plant Research Laboratory, Logan, UT, USA. Dabrowski WM, Sikorski ZE. (Eds), Toxins in Food, pp. 11-63, CRC Press LLC, Boca Raton, Florida;
20. (b) Shukla YN. (2003) Chemical, botanical and pharmacological studies on the genus Echinops: A review. Journal of Medicinal and Aromatic Plant Sciences, 25, 720-732;
21. (c) Wolski, T, Ludwiczuk A. (2002) Naturally occurring pesticides and their plant protection applications. Przemysl Chemiczny (Polska), 81, 370-373.
22. (a) Chitwood DJ. (1993) Naturally occurring nematicides. ACS Symposium Series, 524, 300-315;
23. (b) Halstead BW. (1969) Marine biotoxins: a new source of medicinals. Lloydia, 32, 484-488;
24. (c) Amano K. (1967) Marine products. Genshiryoku Kogyo, 13, 24-26.
25. (a) Dembitsky VM, Tolstikov GA, (2003) Natural Organic Halogenated Compounds. Nauka Press, Novosibirsk, pp. 366;
26. (b) Pettit GP, Pierson FH, Herald CL. (1994) Anticancer Drugs from Animals, Plants, and Microorganisms. John Wiley & Sons, Inc. New York, pp.670.
27. (a) Ebermann R, Alth G, Kreitner M, Kubin A. (1996) Natural products derived from plants as potential drugs for the photodynamic destruction of tumor cells. Journal of Photochemistry and Photobiology, 36B, 95-97;
28. (b) Kasprzycka-Guttman T. (1994) The thermochemistry of the C-triple-C bond. Chemistry of Triple-Bonded Functional Groups, 2, 473-483.
29. (a) Horspool WM. (1994) Photochemistry and radiation chemistry. Chemistry of Triple-Bonded Functional Groups, 2, 375-471;
30. (b) Heinrich M, Robles M, West JE, Ortiz de Montellano BR, Rodriguez E. (1998) Ethnopharmacology of Mexican Asteraceae (Compositae). Annual Review of Pharmacology and Toxicology, 38 539-365.
31. (a) Sugiyama T. (1987) Chemical studies on optically active natural products with interesting biological activities. Nippon Nogei Kagaku Kaishi, 61, 925-930;
32. (b) Cheuk KKL, Li BS, Tang BZ. (2002) Amphiphilic polymers comprising of conjugated polyacetylene backbone and naturally occurring pendants: synthesis, chain helicity, self-assembling structure, and biological activity. Current Trends in Polymer Science, 7, 41-55;
33. (c) Lam JWY, Tang BZ. (2005) Functional polyacetylenes. Accounts of Chemical Research, 38, 745-754;
34. (d) Malchenko OA, Soboleva NP, Zotchik N V, Pavlovskaya G, Rubtsov IA. (1974) Preparation and biological activity of a number of compounds of the acetylene series. Pharmaceutical Chemical Journal, 8, 458-461.
35. (a) Soerensen NA. (1968) Taxonomic significance of acetylenic compounds in plants. Recent Advances in Phytochemistry, 1, 187-227;
36. (b) Soerensen NA. (1963) Chemical taxonomy of acetylenic compounds. In: Chemistry of Plant Taxonomy (Swain T, Ed.), pp. 219-252, Academic Press, London-N.Y.;
37. (c) Soerensen NA. (1960) Acetylene compounds in Compositae; variations and possibilities of application. Svensk Kemisk Tidskrift, 72, 265-274;
38. (d) Bohlmann F. (1988) Naturally-occurring acetylenes. Bioactive Molecules, 7, 1-19;
39. (e) Bohlmann F. (1973) Naturally occurring acetylenes. Phytochemistry, 3, 112-131;
40. (f) Bohlmann F. (1969) Natural acetylene compounds. Chemie in Unserer Zeit, 3, 106-110;
41. (g) Bohlmann F. (1969) Acetylenes from nature. Chemistry of Acetylenes, 977-986.
42. (a) Christensen LP, Lam J. (1991) Acetylenes and related compounds in Heliantheae. Phytochemistry, 30, 11-49;
43. (b) Christensen LP, Lam J. (1991) Acetylenes and related compounds in Asteraceae. Phytochemistry, 30, 2453-2476;
44. (c) Christensen LP. (1998) Biological activities of naturally occurring acetylenes and related compounds from higher plants. Recent Research Developments in Phytochemistry, 2, 227-257;
45. (d) Christensen LP, Lam J. (1990) Acetylenes and related compounds in Cynareae. Phytochemistry, 29, 2753-2785.
46. (a) Frodin DG, Govaerts R. (2004) A comprehensive systematic alphabetical catalogue of genera and species in the family Araliaceae, with full synonymy, source references, generic descriptions and historical accounts, and black-and-white illustrations. Kew Publishing, Surrey, UK, pp. 456;
47. (b) Cannon JFM. (1978) Araliaceae. Flora zambesiaca, 4, 621-632;
48. (c) Plunkett GM, Soltis DE, Soltis PS. (1997) Clarification of the relationship between Apiaceae and Araliaceae based on MATK and RBCL sequence data. American Journal of Botany, 84, 565-580;
49. (d) Strey RG. (1981) Observations on the morphology of the Araliaceae in southern Africa. Journal of Dendrology, 1, 66-83.
50. (a) Yun YS, Lee SY, Kim BS, Yun TK. (1980) Studies on the mechanism of action of the cytotoxic fractions from Korean ginseng roots. II. Effects of ethyl acetate fraction from Korean ginseng roots on the biosynthesis of macromolecules in mammalian neoplastic cells. Han'guk Saenghwa Hakhoechi, 13, 219-234;
51. (b) Sohn J, Lee CH, Chung DJ, Park SH, Kim I, Hwang WI. (1998) Effect of petroleum ether extract of Panax ginseng roots on proliferation and cell cycle progression of human renal cell carcinoma cells. Experimental & Molecular Medicine, 30, 47-51;
52. (c) Yun YS, Lee SY, Kim BS, Yun TK. (1980) Studies on the mechanism of action of the cytotoxic fraction from Korean ginseng roots. I. Effects of petroleum ether fraction from Korean ginseng roots on the biosynthesis of macromolecules in mammalian neoplastic cells. Han'guk Saenghwa Hakhoechi, 13, 203-217;
53. (d) Oh M, Choi YH, Choi S, Chung H, Kim K, Kim SI, Kim DK, Kim ND. (1999) Anti-proliferating effects of ginsenoside Rh2 on MCF-7 human breast cancer cells. International Journal of Oncology, 14, 869-875;
54. (e) Matsuzaki P, Akisue G, Salgado OSC, Gorniak SL, Zaidan DML. (2003) Effect of Pfaffia paniculata (Brazilian ginseng) on the Ehrlich tumor in its ascitic form. Life sciences, 74, 573-579;
55. (f) Duda RB, Taback B, Kessel B, Dooley DD, Yang H, Marchiori J, Slomovic BM, Alvarez JG. (1996) pS2 expression induced by American ginseng in MCF-7 breast cancer cells. Annals of Surgical Oncology, 3, 515-520.
56. (a) Yamamoto M. (1973) Biochemical effects of Panax ginseng on bone marrow, testicular, and cancer cells. Taisha, 10, 581-589;
57. (b) Arichi S, Hayashi T, Kubo M. (1982) Antitumor agent. 41 pp. Patent CA 1116521 A1 19820119, Application: CA 78-306536 19780629;
58. (c) Hatono S, Fuwa T, Natori S, Mizutani K, Kasai R, Tanaka O. (1986) Tumor killing factor inducers. Japan Kokai Tokkyo Koho, 5 pp. Japanese Patent: 61109732 A2 19860528 Showa;
59. (d) Yuan Q. (1987) Complex herb decoction-inert gas combinations as neoplasm inhibitors. Faming Zhuanli Shenqing Gongkai Shuomingshu, 3 pp. Chinese Patent: CN 85105783 A 19870121;
60. (e) Bespalov VG, Alexandrov VA, Yaremenko KV, Davydov VV, Lazareva NL, Limarenko AYu, Slepyan LI, Petrov AS, Troyan DN. (1992) The inhibitory effect of phytoadaptogenic drugs bioginseng, Eleutherococcus senticosus, and Rhaponticum carthamoides on development of N-nitrosoethylurea-induced tumors of the nervous system in rats. Voprosy Onkologii, 38, 1073- 1080;
61. (f) Konoshima T, Takasaki M, Tokuda H. (1999) Anti-carcinogenic activity of the roots of Panax notoginseng. II. Biological & Pharmaceutical Bulletin, 22, 1150-1152.
62. (a) Fujimoto Y, Satoh M. (1987) Acetylenes from the callus of Panax ginseng. Phytochemistry, 26, 2850-2852;
63. (b) Fujimoto Y, Ushiyama K, Sato Y. (1986) Extraction of panaxacol from Panax ginseng for its use as an anticancer agent. Japan Kokai Tokkyo Koho, 7 pp. Japanese Patent: 61218524 A2 19860929 Showa;
64. (c) Fujimoto Y, Satoh M, Takeuchi N, Kirisawa M. (1989) Synthesis and the absolute configuration of panaxacol. Chemistry Letters, 9, 1619-1622;
65. (d) Fujimoto Y, Sato Y, Takeuchi N, Ushama K.(1990) Preparation of dihydropanaxacol derivatives as potential anticancer agents. Japan Kokai Tokkyo Koho, 10 pp. Japanese Patent: JP 02073026 A2 19900313 Heisei;
66. (e) Fujimoto Y, Satoh M, Takeuchi N, Kirisawa M. (1990) Synthesis and absolute configurations of the cytotoxic polyacetylenes isolated from the callus of Panax ginseng. Chemical & Pharmaceutical Bulletin, 38, 1447-1450;
67. (f) Kotsuki H. (1990) Enantioselective total synthesis of natural products by using novel coupling reactions of chiral triflates. Trends in Organic Chemistry, 1, 141-150;
68. (g) Kotsuki H. (1999) Chiral triflate technology. An efficient tool for the construction of biologically interesting natural products in optically pure forms. Yuki Gosei Kagaku Kyokaishi, 57, 334-345;
69. (h) Kotsuki H, Kadota I, Ochi M. (1990) An efficient method for the alkylation of chiral triflates with alkynyllithium reagents. A highly concise total synthesis of (+)- panaxacol. Tetrahedron Letters, 31, 4609-4612.
70. (a) Kim SI, Kang KS, Kim H, Ahn BZ. (1989) Panaxyne, a new cytotoxic polyyne from Panax ginseng root against L1210 cell. Saengyak Hakhoechi, 20, 71-75;
71. (b) Kim H, Kim SI. (1990) HPLC analysis of free malonaldehyde in nine ginseng polyacetylenetreated liver microsome. Koryo Insam Hakhoechi, 14, 373-378.
72. Kim SI, Kang KS, Lee YH. (1989) Panaxyne epoxide, a new cytotoxic polyyne from Panax ginseng root against L1210 cells. Archives of Pharmacal Research, 12, 48-51.
73. (a) Poplawski J, Wrobel JT, Glinka T. (1980) Panaxydol, a new polyacetylenic epoxide from Panax ginseng roots. Phytochemistry, 19, 1539-1541;
74. (b) Saita T, Katano M, Matsunaga H, Yamamoto H, Fujito H, Mori M. (1993) The first specific antibody against cytotoxic polyacetylenic alcohol, panaxynol. Chemical & Pharmaceutical Bulletin, 41, 549-552;
75. (c) Kitagawa I, Taniyama T, Shibuya H, Noda T, Yoshikawa M. (1987) Chemical studies on crude drug processing. V. On the constituents of ginseng radix rubra (2): Comparison of the constituents of white ginseng and red ginseng prepared from the same Panax ginseng root. Yakugaku Zasshi, 107, 495-505;
76. (d) Ahn BZ, Kim SI. (1988) Relation between structure and cytotoxic activity of panaxydol analogs against L1210 cells. Archiv der Pharmazie (Weinheim), 321, 61-63;
77. (e) Matsunaga H, Katano M, Yamamoto H, Fujito H, Mori M, Takata K. (1990) Cytotoxic activity of polyacetylene compounds in Panax ginseng C.A. Meyer. Chemical & Pharmaceutical Bulletin, 38, 3480-3484.
78. Kim YS, Kim SI, Hahn DR. (1989) Effects of polyacetylenes from Panax ginseng on some microsomal and mitochondrial enzymes. Saengyak Hakhoechi, 20, 154-161.
79. Kim H, Lee YH, Kim SI. (1988) A possible mechanism of polyacetylene membrane cytotoxicity. Korean Journal of Toxicology, 4, 95-105.
80. Matsunaga H, Katano M, Saita T, Yamamoto H, Mori M. (1994) Potentiation of cytotoxicity of mitomycin C by a polyacetylenic alcohol, panaxytriol. Cancer Chemotherapy and Pharmacology, 33, 291-297.
81. Matsunaga H, Saita T, Nagumo F, Mori M, Katano M. (1995) A possible mechanism for the cytotoxicity of a polyacetylenic alcohol, panaxytriol: Inhibition of mitochondrial respiration. Cancer Chemotherapy and Pharmacology, 35, 291-296.
82. (a) Kim YS, Kim SI, Hahn DR. (1988) Effect of polyacetylene compounds from Panax ginseng on macromolecular synthesis by lymphoid leukemia L1210. Yakhak Hoechi, 32, 137-140;
83. (b) Otsuka H, Komiya T, Fujioka S, Goto M, Hiramatsu Y, Fujimura H. (1981) Studies on anti-inflammatory agents. IV. Anti-inflammatory constituents from roots of Panax ginseng C.A. Meyer. Yakugaku Zasshi, 101, 1113-1117;
84. (c) Alanko J, Kurahashi Y, Yoshimoto T, Yamamoto S, Baba K. (1994) Panaxynol, a polyacetylene compound isolated from oriental medicines, inhibits mammalian lipoxygenases. Biochemical pharmacology, 48, 1979-1981.
85. (a) Kim JY, Lee K-W, Kim S-H, Wee JJ, Kim Y-S, Lee HJ. (2002) Inhibitory effect of tumor cell proliferation and induction of G2/M cell cycle arrest by panaxytriol. Planta Medica, 68, 119-122;
86. (b) Nakano Y, Matsunaga H, Saita T, Mori M, Katano M, Okabe H. (1998) Antiproliferative constituents in Umbelliferae plants II. Screening for polyacetylenes in some Umbelliferae plants, and isolation of panaxynol and falcarindiol from the root of Heracleum moellendorffii. Biological & Pharmaceutical Bulletin, 21, 257-261.
87. (a) Fujimoto Y, Sato M. (1988) A new cytotoxic chlorine-containing polyacetylene from the callus of Panax ginseng. Chemical & Pharmaceutical Bulletin, 36, 4206-4208;
88. (b) Fujiki Y, Sato Y, Ushiyama K. (1987) Anticancer agents containing heptadeca-4,6- diynes and formulations thereof. Japan Kokai Tokkyo Koho, 6 pp. Japanese Patent: JP 62207234 A2 19870911 Showa;
89. (c) Fujimoto Y, Honma Y, Sato Y, Ushiyama, K. (1989) Fungicides containing heptadecadiyne derivatives. Japan Kokai Tokkyo Koho, 5 pp. Japanese Patent: JP 01006201 A2 19890110 Heisei.
90. Kim SI, Lee YH, Kang KS. (1989) 10-Acetyl panaxytriol, a new cytotoxic polyacetylene from Panax ginseng. Yakhak Hoechi, 33, 118-123.
91. Hirakura K, Takagi H, Morita M, Nakajima K, Niitsu K, Sasaki H, Maruno M, Okada M. (2000) Cytotoxic activity of acetylenic compounds from Panax ginseng. Natural Medicines (Tokyo), 54, 342-345.
92. Kazuhiro F, Fushimi K, Chin M. (1994) Acetylnic compounds of Panax ginseng and neoplasm inhibitors containing them. Japan Kokai Tokkyo Koho, 6 pp. Japanese Patent: JP 06025088 A2 19940201 Heisei.
93. (a) Saita T, Katano M, Matsunaga H, Kouno I, Fujito H, Mori M. (1995) Screening of polyacetylenic alcohols in crude drugs using the ELISA for panaxytriol. Biological & Pharmaceutical Bulletin (Tokyo), 18, 933-937;
94. (b) Lee G, Park H-G, Choi M-L, Kim YH, Park YB, Song K-S, Cheong C, Bae Y-S. (2000) Falcarindiol, a polyacetylenic compound isolated from Peucedanum japonicum, inhibits mammalian DNA topoisomerase I. Journal of Microbiology and Biotechnology, 10, 394-398;
95. (c) Setzer WN, Gu X, Wells EB, Setzer MC, Moriarity DM. (2000) Synthesis and cytotoxic activity of a series of diacetylenic compounds related to falcarindiol. Chemical & Pharmaceutical Bulletin, 48, 1776-1777;
96. (d) Bae YS, Choi MR, Jung JJ, Kim YH, Lee G, Park HG, Park YB, Song GS. (2002) Falcarindiol extracted from Peucedanum japonicum and production thereof. Korean Kongkae Taeho Kongbo, Korean Patent: KR 2002053473 A 20020705.
97. Fujimoto Y, Satoh M, Takeuchi N, Kirisawa M. (1991) Cytotoxic acetylene from Panax quinquefolium. Chemical & Pharmaceutical Bulletin, 39, 521-523.
98. Fujimoto Y. (1994) Panaquinquecols of Panax quinquefolium and their use as anticancer agents. Japan Kokai Tokyo Koho, 9 pp. Japanese Patent: JP 06009418 A2 19940118 Heisei.
99. Fujimoto Y, Wang H, Kirisawa M, Satoh M, Takeuchi N. (1992) Acetylenes from Panax quinquefolium. Phytochemistry, 31, 3499-3501.
100. (a) Bae HO, Chae GY, Chung HT, Jang SI, Kwon TO, Lee HS, Oh HC, Yun YG. (2003) Acetylene compounds separated from Acanthopanax senticosus and composition containing the same to induce apoptosis. Kongkae Taeho Kongbo, No pp. Korean Patent: KP 2003059643 A 20030710;
101. (b) Zhang Y, Liu B, Pei Y. (2002) Pharmacological action of Acanthopanax senticosus (Rupr. et Maxim.) Harms. Shenyang Yaoke Daxue Xuebao, 19, 143-146;
102. (c) Kwak TH, Shin MS, Kim JY, Park J-K. (2003) Active fraction having anticancer and anti-metastasis isolated from Acanthopanax species and fruits. PCT International, 43 pp. WO 2003099309 A1 Application: WO 2003-KR1043 20030528;
103. (d) Zhang Z. (2005) Manufacture of traditional Chinese medicine freeze dried powder injection for treating tumors. Faming Zhuanli Shenqing Gongkai Shuomingshu, 15 pp. Chinese Patent: CN 1559454 A 20050105;
104. (e) Kustrak D. (1993) Siberian ginseng or the root from taiga - Eleutherococcus senticosus. Farmaceutski Glasnik, 49, 1-7;
105. (f) Nishibe S. (1995) Bioactive lignans and flavonoids from traditional medicines. Colloques - Institut National de la Recherche Agronomique, 69, 113-122;
106. (g) Smith M, Boon HS. (1999) Counseling cancer patients about herbal medicine. Patient education and counseling, 38, 109-120;
107. (h) Nishibe S, Deyama T. (2002) Bioactive lignans from herbal medicines. Natural Medicines (Tokyo), 56, 227-238.
108. Fujihashi T, Okuma T, Hirakura K, Mihashi H. (1991) Anticancer agents containing polyacetylenes. Japan Kokai Tokkyo Koho, 14 pp. Japanese Patent: JP 03200736 A2 19910902 Heisei.
109. Fujimoto Y, Wang H, Satoh M, Takeuchi N. (1994) Polyacetylenes from Panax quinquefolium. Phytochemistry, 35, 1255-1257.
110. Tanaka S, Ikeshiro Y, Tabata M, Konoshima M. (1977) Anti-nociceptive substances from the roots of Angelica acutiloba. Arzneimittel-Forschung, 27, 2039-2045.
111. (a) Haigh WG, Morris LJ, James AT. (1968) Acetylenic acid biosynthesis in Crepis rubra. Lipids, 3, 307-312;
112. (b) Haigh WG, James AT. (1967) The biosynthesis of an acetylenic acid, crepenynic acid. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism, 137, 391-392;
113. (c) Susilo R. (2002) Preparation of pharmaceutically active uridine ester nucleosides against a variety of diseases. PCT Int. Application, 73 pp., German Patent: WO 2002088159 A1 20021107;
114. (d) Nugteren DH, Christ-Hazelhof E. (1987) Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesis. Prostaglandins, 33, 403-417.
115. (a) Brandt K, Christensen LP. (2000) Vegetables as nutraceuticals - falcarinol in carrots and other root crops. Special Publication - Royal Society of Chemistry, 255, 386-391;
116. (b) Yates SG, England RE, Kwolek WF, Simon PW. (1983) Analysis of carrot constituents: myristicin, falcarinol, and falcarindiol. ACS Symposium Series, Xenobiotics Foods Feeds, 234, 333-344.
117. (a) Bernart MW, Cardellina JH, II, Balaschak MS, Alexander M, Shoemaker RH, Boyd MR. (1996) Cytotoxic falcarinol oxylipins from Dendropanax arboreus. Journal of Natural Products, 59, 748-753;
118. (b) Setzer WN, Green TJ, Whitaker KW, Moriarity DM, Yancey CA, Lawton RO, Bates RB (1995) A cytotoxic diacetylene from Dendropanax arboreus. Planta Medica, 61, 470-471.
119. (c) Pino JA, Marbot R, Payo A, Chao D, Herrera P, Marti MP. (2005) Leaf oil of Dendropanax arboreus L. from Cuba. Journal of Essential Oil Research, 17, 547-548.
120. (a) Moriarity DM, Huang J, Yancey CA, Zhang P, Setzer WN, Lawton RO, Bates RB, Caldera S. (1998) Lupeol is the cytotoxic principle in the leaf extract of Dendropanax cf. querceti. Planta Medica, 64, 370-372;
121. (b) Nagaya H, Nagae T, Usami A, Itokawa H, Takeya K, Omar AA. (1994) Cytotoxic chemical constituents from Egyptian medicinal plant, Ambrosia maritima L. Natural Medicines (Tokyo), 48, 223-226;
122. (c) Zid SA, Orihara Y. (2005) Polyacetylenes accumulation in Ambrosia maritima hairy root and cell cultures after elicitation with methyl jasmonate. Plant Cell, Tissue and Organ Culture, 81, 65-75.
123. (a) Li Y, Li M, Wang L, Jiang Z, Li W, Li H. (2004) Induction of apoptosis of cultured hepatocarcinoma cell by essential oil of Artemisia annua L. Sichuan Daxue Xuebao, Yixueban, 35, 337-339;
124. (b) Morelli I, Scoccianti E. (2003) Antitumor extracts from plants of the Asteraceae family. Italian Patent: IT 1317107 B1 20030526, 12 pp.;
125. (c) Seo H-J, Park K-K, Han SS, Chung W-Y, Son M-W, Kim W-B, Surh Y-J. (2002) Inhibitory effects of the standardized extract (DA-9601) of Artemisia asiatica Nakai on phorbol ester-induced Orn decarboxylase activity, papilloma formation, cyclooxygenase-2 expression, inducible nitric oxide synthase expression, and nuclear transcription factor kB activation in mouse skin. International Journal of Cancer, 100, 456-462.
126. (a) Jung DY, Park SW. (2002) Cytotoxicity of water fraction of Artemisia argyi against L1210 cells and antioxidant enzyme activities. Yakhak Hoechi, 46, 39-46;
127. (b) Jung DY, Ha HK, Kim AN, Lee SM, Min TJ, Park SW. (2000) Cytotoxicity of SD-994, a methanolic extract of Artemisia argyi, against L1210 cells with concomitant induction of antioxidant enzymes. Yakhak Hoechi, 44, 213-223.
128. Bhakuni RS, Jain DC, Sharma RP, Kumar S. (2001) Secondary metabolites of Artemisia annua and their biological activity. Current Science, 80, 35-48.
129. (a) Nakamura Y, Ohto Y, Murakami A, Jiwajinda S, Ohigashi H. (1998) Isolation and identification of acetylenic spiroketal enol ethers from Artemisia lactiflora as inhibitors of superoxide generation induced by a tumor promoter in differentiated HL-60 cells. Journal of Agricultural and Food Chemistry, 46, 5031-5036;
130. (b) Murakami A, Ohigashi H. (1999) Cancer preventive potentials of edible plants from subtropical countries. Food Style, 3, 35-39;
131. (c) Ohigashi H, Nakamura Y, Murakami A. (1998) Active components and antitumor effects of tropical Asian foods. Food Style, 2, 31-35.
132. Nakamura Y, Kawamoto N, Ohto Y, Torikai K, Murakami A, Ohigashi H. (1999) A diacetylenic spiroketal enol ether epoxide, AL-1, from Artemisia lactiflora inhibits 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion possibly by suppression of oxidative stress. Cancer Letters, 140, 37-45.
133. (a) Xu C, Sun X, Yang J, Yu D, Li Q, Zhang Y, Dou S. (1986) The structure of lactiflorasyne isolated from Artemisia lactiflora wall. Yao Xue Xue Bao, 21, 772-775;
134. (b) Fang H, Hu Q, Ma Y, Sun S, Xu C, Zeng X,; Zhang Q, Zhou Y. (1984) Constituents of volatile oils. IV. Chemical constituents of the volatile oil from Bai Hua Hao (Artemisia lactiflora Wall). Zhongcaoyao, 15, 99-101.
135. (a) Matsumoto T, Katsuya H, Matsumoto A, Tokuda H. (1991) Japan Kokai Tokkyo Koho, 4 pp. Japanese Patent: JP 03287528 A2 19911218 Heisei;
136. (b) Matsumoto T, Katsuya H, Matsumoto A, Tokuda H. (1991) Antitumor capillin and/or capillone from plants. Japan Kokai Tokkyo Koho, 4 pp. Japanese Patent: JP 03287528 A2 19911218 Heisei;
137. (c) Xie T, Liu J, Liang J-Y, Zhang Z-M, Wei X-L. (2005) Acetylenes and flavonoids from Artemisia scoparia II. Zhongguo Tianran Yaowu, 3, 86-89.
138. (a) Konovalov DA, Konovalova OA, Chelombit'ko VA. (1992) Chemical composition of the essential oil of Artemisia scoparia. Khimiya Prirodnykh Soedinenii, 1, 142-143;
139. (b) Spiridonov NA, Konovalov DA, Arkhipov VV. (2005) Cytotoxicity of some Russian ethnomedicinal plants and plant compounds. Phytotherapy Research, 19, 428-432.
140. Appendino G, Menichini F, Puntillo D. (1988) Aromatic acetylenes and flavanones from Artemisia variabilis. Fitoterapia, 59, 425-426.
141. De Pascual T, Jr, Gonzales MS, De Dios MA, San Segundo JM, Vicente S, Bellido IS. (1981) Essential oil of Santolina rosmarinifolia Linnaeus. Rivista Italiana EPPOS, 63, 355-356.
142. Whelan LC, Ryan MF. (2004) Effects of the polyacetylene capillin on human tumor cell lines. Anticancer Research, 24, 2281- 2286;
143. (b) Okuno I, Namba T. (2004) Pharmacognostical studies on Yinchenhao. Journal of Traditional Medicines, 21, 187-198.
144. Konovalov DA, Chelombit'ko VA. (1991) The composition of essential oil of Artemisia scoparia Waldst et Kit. during growth. Rastitel'nye Resursy (Russia), 27, 135-139.
145. Yano K. (1975) Natural acetylenes. 2. Variation in acetylene content of different ecotypes of Artemisia capillaris. Phytochemistry, 14, 1783-1784.
146. (a) Liu W. (1999) Medicine for treatment of cancer. Faming Zhuanli Shenqing Gongkai Shuomingshu, 5 pp. Chinese Patent: CN 1231922 A 19991020;
147. (b) Zhang Z, Cheng D, Xu H, Wu Y, Fan J. (2004) The bioactivities and mechanism of spiro enol ether derivatives. Zhiwu Baohu Xuebao, 31, 411-417;
148. (c) Yin B-L, Fan J-F, Gao Y, Wu Y-L. (2003) Progress in molecular diversity of tonghaosu and its analogs. ARKIVOC (Gainesville, FL, USA), 2, 70-83.
149. (a) Fan J-F, Yin B-L, Zhang Y-F, Wu Y-L, Wu Y-K. (2001) Molecular diversity of tonghaosu analogs. Synthesis of 2-(Z)- benzylidene-1,6,9- trioxaspiro[4,5]dec-3-ene. Huaxue Xuebao, 59, 1756-1762;
150. (b) Windsor JB, Roux SJ, Lloyd AM, Thomas CE. (2005) Methods and compositions for increasing the efficacy of biologically-active ingredients such as antitumor agents. PCT International, Application, 243 pp. WO 2005014777 A2 20050217.
151. (a) Chen L, Xu HH, Yin BL, Xiao C, Hu TS, Wu YL.(2004) Synthesis and antifeeding activities of tonghaosu analogues. Journal of Agricultural and Food Chemistry, 52, 6719-6723;
152. (b) Trovato A, Monforte MT, Rossitto A, Forestieri AM (1996) In vitro cytotoxic effect of some medicinal plants containing flavonoids. Bollettino Chimico Farmaceutico, 135, 263-266.
153. (a) Chen L, Xu HH, Hu TS, Wu YL. (2005) Synthesis of spiroketal enol ethers related to tonghaosu and their insecticidal activities. Pest Management Science, 61, 477-482;
154. (b) Xu H, Zhang Z, Cheng D, Wu Y, Fan J. (2000) Study on bioactivity of derivate of spiro enol ether against Spodopter litura fabricius. Huazhong Nongye Daxue Xuebao, 19, 543-546.
155. Fullas F, Brown DM, Wani MC, Wall ME, Chagwedera TE, Farnesworth NR, Pezzuto JM, Kinghorn AD. (1995) Gummiferol, a cytotoxic polyacetylene from the leaves of Adenia gummifera. Journal of Natural Products, 58, 1625-1628.
156. Jung HJ, Min BS, Park JY, Kim YH, Lee HK, Bae KH. (2002) Gymnasterkoreaynes A-F, cytotoxic polyacetylenes from Gymnaster koraiensis. Journal of Natural Products, 65, 897-901.
157. Bae KH, Jung HJ, (1999) Biological polyacetylenes from Gymnaster koraiensis (Nakai) Kitamura. Recent Advances in Natural Products Research, Proceedings of the International Symposium on Recent Advances in Natural Products Research, 3rd, Seoul, Republic of Korea, Nov. 19, 37-41.
158. (a) Matsumoto A, Katsuya H, Matsumoto T,; Tokuda H. (1991) Antitumor polyacetylene extraction from plants. Japan Kokai Tokyo Koho, 4 pp. Japanese Patent: JP 03287532 A2 19911218 Heisei;
159. (b) Ionkova I, Alferman A. (2000) Use of DNA for detection and isolation of potential anticancer agents from plants. Farmatsiya (Sofia), 47, 10-16;
160. (c) Nakamura N, Nemoto M. (1997) cis-Dehydromatricaria ester concentration in plant and its leaching of Solidago altissima L. Zasso Kenkyu, 41, 359-361;
161. (d) Lu T, Menelaou MA, Vargas D, Fronczek FR, Fischer NH. (1993) Polyacetylenes and diterpenes from Solidago canadensis. Phytochemistry, 32, 1483-1488;
162. (e) Lam J, Christensen LP, Farch T, Thomasen T. (1992) Acetylenes from the roots of Solidago species. Phytochemistry, 31, 4159-4161;
163. (f) Zdero C, Bohlmann F, King RM, Robinson H. (1988) Polyynes from Calotis species. Phytochemistry, 27, 1105-1107.
164. (a) Marles RJ, Farnsworth NR, Neill DA. (1989) Isolation of a novel cytotoxic polyacetylene from a traditional anthelmintic medicinal plant, Minquartia guianensis. Journal of Natural Products, 52, 261-266;
165. (b) Mell CD. (1937) Interesting sources of natural dyestuffs. Textile Colorist, 59, 482-484.
166. Fort DM, King SR, Carlson TJ, Nelson ST. (2000) Minquartynoic acid from Coula edulis. Biochemical Systematics and Ecology, 28, 489-490.
167. (a) Ito A, Cui B, Chavez D, Chai HB, Shin YG, Kawanishi K, Kardono LB, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Kinghorn AD. (2001) Cytotoxic polyacetylenes from the twigs of Ochanostachys amentacea. Journal of Natural Products, 64, 246-248;
168. (b) Rashid MA, Gustafson KR, Cardellina JH, II, Boyd MR. (2001) Absolute stereochemistry and anti-HIV activity of minquartynoic acid, a polyacetylene from Ochanostachys amentacea. Natural Product Letters, 15, 21-26.
169. El-Seedi HR, Hazell AC, Torssell KBG. (1994) Triterpenes, lichexanthone and an acetylenic acid from Minquartia guianensis. Phytochemistry, 35, 1297-1299.
170. Rasmussen HB, Christensen SB, Kvist LP, Kharazmi A, Huansi AG. (2000) Absolute configuration and antiprotozoal activity of minquartynoic acid. Journal of Natural Products, 63, 1295-1296.
171. Zidorn C, Joehrer K, Ganzera M, Schubert B, Sigmund EM, Mader J, Greil R, Ellmerer EP, Stuppner H. (2005) Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities. Journal of Agricultural and Food Chemistry, 53, 2518-2523.
172. Hu CQ, Chang JJ, Lee KH. (1990) Antitumor agents. 115. Seselidiol, a new cytotoxic polyacetylene from Seseli mairei. Journal of Natural Products, 53, 932-935.
173. (a) Perry NB, Span EM, Zidorn C. (2001) Aciphyllal - a C34-polyacetylene from Aciphylla scott-thomsonii (Apiaceae). Tetrahedron Letters, 42, 4325-4328;
174. (b) Patnam R, Touaibia M, Liu B, Roy R. (2005) Studies toward the total synthesis of Aciphyllal, a novel C34-polyacetylene. Abstracts of Papers, 230th ACS National Meeting, Washington, DC, Aug. 28-Sept. 1, ORGN-172.
175. (a) Takaishi Y, Okuyama T, Nakano K, Murakami K, Tomimatsu T. (1991) Absolute configuration of a triolacetylene from Cirsium japonicum. Phytochemistry, 30, 2321-2324;
176. (b) Takaishi Y, Okuyama T, Masuda A, Nakano K, Murakami K, Tomimatsu T. (1990) Acetylenes from Cirsium japonicum. Phytochemistry, 29, 3849-3852;
177. (c) Fei Z, Kong L, Peng S. (2001) Progress in chemical and pharmacological studies on Cirsium japonicum. Zhongcaoyao, 32, 664-667.
178. Yim SH, Kim HJ, Lee IS. (2003) A polyacetylene and flavonoids from Cirsium rhinoceros. Archives of Pharmacal Research, 26, 128-131.
179. (a) Ohashi K, Winarno H, Mukai M, Inoue M, Prana MS, Simanjuntak P, Shibuya H. (2003) Indonesian medicinal plants. XXV. Cancer cell invasion inhibitory effects of chemical constituents in the parasitic plant Scurrula atropurpurea (Loranthaceae). Chemical & Pharmaceutical Bulletin, 51, 343-345;
180. (b) Winarno H, Ohashi K, Shibuya H. (2003) Chemical study on the parasitic plant Scurrula atropurpurea (Loranthaceae), an Indonesian medicinal plant. Fukuyama Daigaku Yakugakubu Kenkyu Nenpo, 21, 13-29.
181. Ohashi K, Winarno H, Mukai M, Shibuya H. (2003) Preparation and cancer cell invasion inhibitory effects of C16-alkynic fatty acids. Chemical & Pharmaceutical Bulletin, 51, 463-466.
182. (a) Zhang H.-J, Sydara K, Tan GT, Ma C, Southavong B, Soejarto DD, Pezzuto JM, Fong HHS. (2004) Bioactive Constituents from Asparagus cochinchinensis. Journal of Natural Products, 67, 194-200;
183. (b) Terada K, Honda C, Suwa K, Takeyama S, Oku H, Kamisako W. (1995) Acetylenic compounds isolated from cultured cells of Asparagus officinalis. Chemical & Pharmaceutical Bulletin, 43, 564-566;
184. (c) Terada K, Suwa K, Takeyama S, Honda C, Kamisako W. (1996) Biosynthesis of the acetylenic compounds in cultured cells of Asparagus officinalis from D- and 13C-labeled phenylalanines. Biological & Pharmaceutical Bulletin, 19, 748-751.
185. (a) Resch M, Heilmann J, Steigel A, Bauer R. (2001) Further phenols and polyacetylenes from the rhizomes of Atractylodes lancea and their anti-inflammatory activity. Planta Medica, 67, 437-442;
186. (b) Nakai Y, Kido T, Hashimoto K, Kase Y, Sakakibara I, Higuchi M, Sasaki H, (2003) Effect of the rhizomes of Atractylodes lancea and its constituents on the delay of gastric emptying. Journal of Ethnopharmacology, 84, 51-55;
187. (c) Nishikawa Y, Yasuda I, Watanabe Y, Seto T. (1976) Studies on the components of Atractylodes. II. New polyacetylenic compounds in the rhizome of Atractylodes lancea De Candolle var. chinensis Kitamura. Yakugaku Zasshi, 96, 1322-1326;
188. (d) Nakajima K, Yanagisawa T, Iimura F, Mihashi H. (1992) Anti-inflammatory and antiallergy agents containing polyacetylenes. Japan Kokai Tokkyo Koho, 6 pp., Japanese Patent: JP 04208222 A2 19920729 Heisei.
189. (a) Gonzalez AG, Estevez-Reyes R, Estevez-Braun A, Ravelo AG, Jimenez IA, Bazzocchi IL, Aguilar MA, Moujir L. (1997) Biological activities of some Argyranthemum species. Phytochemistry, 45, 963-967;
190. (b) Badisa RB, Couladis M, Tsortanidou V, Chaudhuri SK, Walker L, Pilarinou E, Santos-Guerra A, Francisco-Ortega J. (2004) Pharmacological activities of some Argyranthemum species growing in the Canary Islands. Phytotherapy research, 18, 763-767.
191. (a) Hu J-F, Kuhen K, Hafenbradl D, Li J, Chen T, Harris J, Gray N, Schultz PG. (2005) Twenty high-grade traditional Chinese medicines: Their anti-HIV, antibacterial, and anticancer biological screening. Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, March 13-17, MEDI-397;
192. (b) Au TK, Lam TL, Ng TB, Fong WP, Wan DCC. (2001) A comparison of HIV-1 integrase inhibition by aqueous and methanol extracts of Chinese medicinal herbs. Life Sciences, 68, 1687-1694;
193. (c) Collins RA, Ng TB, Fong WP, Wan CC, Yeung HW. (1997) A comparison of human immunodeficiency virus type 1 inhibition by partially purified aqueous extracts of Chinese medicinal herbs. Life Sciences, 60, PL345-PL351.
194. (a) Sarker SD, Nahar L. (2004) Natural medicine: The genus Angelica. Current Medicinal Chemistry, 11, 1479-1500;
195. (b) Li J. (1983) Studies on the chemical constituents of Angelica sinensis. Zhongcaoyao, 14, 377-378;
196. (b) Chen J, Yang C, (2004) Researches in Angelica L. Tianran Chanwu Yanjiu Yu Kaifa, 16, 359-365;
197. (c) Yoshikawa M. (2005) Angelica keiskei. Shokuhin to Kagaku, 47, 27-28;
198. (d) Ma R, Wang Q, Chen X, Sun K, Zhang L. (2002) Advance in research of Angelica sinensis. Zhongcaoyao, 33, 280-282;
199. (e) Huang W, Song C. (2001) Advance in chemical and pharmacological studies of Angelica sinensis (Oliv.) Diel. Zhongguo Zhongyao Zazhi, 26, 147-151.
200. Fujioka T, Furumi K, Fujii H, Okabe H, Mihashi K, Nakano Y, Matsunaga H, Katano M, Mori M. (1999) Antiproliferative constituents from Umbelliferae plants. V. A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chemical & Pharmaceutical Bulletin, 47, 96-100.
201. Furumi K, Fujioka T, Fuji H, Okabe H, Nakano Y, Matsunaga H, Katano M, Mori M, Mihash K. (1998) Novel antiproliferative falcarindiol furanocoumarin ethers from the root of Angelica japonica, Bioorganic & Medicinal Chemistry Letters, 8, 93-96.
202. Akihisa T, Tamura T, Matsumoto T, Kokke WCMC, Yokota T. (1989) Isolation of acetylenic sterols from a higher plant. Further evidence that marine sterols are not unique. Journal of Organic Chemistry, 54, 606-610.
203. (a) Jeon G-C, Park M-S, Yoon D-Y, Shin C-H, Sin H-S, Um S-J. (2005) Antitumor activity of spinasterol isolated from Pueraria roots. Experimental and Molecular Medicine (Korea) 37, 111-120;
204. (b) Rodriguez JB, Gros EG, Bertoni MH, Cattaneo P. (1996) The sterols of Cucurbita moschata ("calabacita") seed oil. Lipids, 31, 1205-1208;
205. (c) Xu L, Liu J, Min D, Wang S, Zhang Z, Guo D, Zheng K. (1998) Chemical constituents of Conyza blinii Levl. Zhongguo Zhong Yao Za Zhi, 23, 293-295;
206. (d) Yang S, Zhong Y, Luo H, Ding X, Zuo C. (1999) Studies on chemical constituents of the roots of Gypsophila oldhamiana Miq. Zhongguo Zhong Yao Za Zhi, 24, 680-681;
207. (e) Herath HM, Athukoralage PS, Jamie JF. (2001) A new oleanane triterpenoid from Gordonia ceylanica. Natural Product Letters, 15, 339-344;
208. (f) Pech GG, Brito WF, Mena GJ, Quijano L. (2002) Constituents of Acacia cedilloi and Acacia gaumeri. Revised structure and complete NMR assignments of resinone. Zeitschrift für Naturforschung, 57C, 773-776;
209. (g) Villasenor IM, Domingo AP. (2000) Anticarcinogenicity potential of spinasterol isolated from squash flowers. Teratogenesis, Carcinogenesis, and Mutagenesis, 20, 99-105.
210. (a) Reisch J, Spitzner W, Schulte KE. (1967) On the problem of the microbiological activity of simple acetylene compounds. Arzneimittel-Forschung, 17, 816-819;
211. (b) Anchel M. (1952) Acetylenic compounds from fungi. Journal of the American Chemical Society, 74, 1588-1590;
212. (c) Jones ERH. (1966) Natural polyacetylenes and their precursors. Chemistry in Britannia, 2, 6-13;
213. (d) McAfee BJ, Taylor A. (1999) A review of the volatile metabolites of fungi found on wood substrates. Natural Toxins, 7, 283-303.
214. (a) Herbst P. (1960) The alkyne acids from fungi. Planta Medica, 8, 394-402;
215. (b) Varadi J, Somogyi J. (1966) Vegetable antimicrobial substances. Gyogyszereszet, 10, 408-414;
216. (c) Stickings CE, Raistrick H. (1956) Chemistry of the fungi. Annual Review of Biochemistry, 25, 225-256.
217. (a) Niimura Y, Hatanaka S. (1977) Biochemical studies on nitrogen compounds of fungi. Part 15. Two g-glutamyl-peptides of acetylenic amino acids in Tricholomopsis rutilans. Phytochemistry, 16, 1435-1436;
218. (b) Okishi H. (1977) 2-g-Glutamylamino-4- hexynic acid and 2-g-glutamylamino-3-hydroxy-4-hexynic acid. Japan Kokai Tokkyo Koho, 4 pp., Japanese Patent: JP 52054084 19770502 Showa;
219. (c) Hatanaka SI, Niimura Y, Taniguch K. (1973) Biochemical studies on nitrogen compounds of fungi. V. Another new amino acid of the acetylene type from Tricholomopsis rutilans. Zeitschrift fuer Naturforschung, 28C, 475-478.
220. (a) Patel RN. (2001) Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Current Opinion in Biotechnology, 12, 587-604;
221. (b) Abdulganeva SA, Erzhanov KB. (1991) Acetylenic amino acids. Uspekhi Khimii, 60, 1318-1342;
222. (c) Metcalf BW, Jung M. (1976) Acetylene derivatives of amino acids. US Patent: 9 pp. US 3959356 19760525;
223. (c) Sung M-L, Fowden L, Millington DS, Sheppard RC. (1969) Acetylenic amino acids from Euphoria longan. Phytochemistry, 8, 1227-1233.
224. (a) Takada Y, Greig NH, Vistica DT, Rapoport SI, Smith QR. (1991) Affinity of antineoplastic amino acid drugs for the large neutral amino acid transporter of the blood-brain barrier. Cancer Chemotherapy and Pharmacology, 29, 89-94;
225. (b) Metcalf BW, Jung M. (1978) α-Acetylenic amino acids useful as inhibitors of aromatic amino acid decarboxylase. Belgrag, 40 pp. Ugoslavia Patent: BE 868596 19781016 CAN 90:204493;
226. (c) Washtien WS. (1977) Acetylenic suicide inactivators. 163 pp. CAN 87:97992 AN 1977:497992;
227. (d) Washtien WS. (1977) Acetylenic suicide inactivators. 163 pp. Dissertation Abstract International B, 37(12, Pt. 1), 6109, CAN 87:97992;
228. (e) Whitehead R. (1999) Natural product chemistry. Annual Reports on the Progress of Chemistry, Section B: Organic Chemistry, 95, 183-205.
229. Jenkins, D.E. (1950) Mycomycin: a new antibiotic with tuberculostatic properties. Journal of Laboratory and Clinical Medicine, 36, 841-842.
230. (a) King DS. (1950) Tuberculosis. New England Journal of Medicine, 243, 530-536;
231. (b) Chain EB. (1958) Chemistry and biochemistry of new antibiotics. Giornae Italian Chemioterapea, 4, 213-242;
232. (c) Beer J. (1955) Natural alkynes. Wiadomosci Chemiczne (Polska), 9, 460-481.
233. (a) Du L, Hu W. (1997) Hepatic artery target embolic chemotherapy in treatment of late-stage primary hepatocellular carcinoma. Shaanxi Yixue Zazhi, 26, 9-11;
234. (b) Veljkovic V, Lalovic DI. (1978) Correlation between the carcinogenicity of organic substances and their spectral characteristics. Experientia, 34, 1342-1343.
235. Schlingmann G, Milne L, Pearce CJ, Borders DB, Greenstein M, Maiese WM, Carter GT. (1995) Isolation, characterization and structure of a new allenic polyene antibiotic produced by fungus LL- 07F275. Journal of Antibiotics, 48, 375-379.
236. (a) Jones ERH, Leeming PR, Remers WA. (1960) Chemistry of the higher fungi. XI. Polyacetylenic metabolites of Drosophila subatrata. Journal of the Chemical Society, 2257-2263;
237. (b) Kavanagh F, Hervey A, Robbins WJ. (1952) Antibiotic substances from basidiomycetes. IX. Drosophila subatrata. Proceedings of the National Academy of Sciences of the United States of America, 38, 555-560;
238. (c) Ahmed M, Hearn MTW, Jones ERH, Thaller V. (1977) Natural acetylenes. Part LI. Biosynthetic studies with C18 acetylenic precursors in fungal cultures. Origin of the carbon skeletons of mycomycin and drosophilins C and D. Journal of Chemical Research, Synopses, 5, 125-131.
239. Anchel M. (1953) Characterization of drosophilin C as a polyacetylene. Archives of Biochemistry and Biophysics, 43, 127-135.
240. Kavanagh F, Hervey A, Robbins WJ. (1952) Antibiotic substances from basidiomycetes. IX. Drosophila subatrata. Proceedings of the National Academy of Sciences of the United States of America, 38, 555-560.
241. (a) Anchel M. (1954) Some naturally occurring antibiotic polyacetylenes. Transactions of the New York Academy of Sciences, 16, 337-342;
242. (b) Asheshov IN, Strelitz F, Hall EA, Flon H. (1954) A survey of actinomycetes for antiphage activity. Antibiotics and Chemotherapy (Washington), 4, 380-394.
243. (a) Garlaschelli L, Magistrali E, Vidari G, Zuffardi O. (1995) Fungal metabolites. 38. Tricholomenyns A and B, novel antimitotic acetylenic cyclohexenone derivatives from the fruiting bodies of Tricholoma acerbum. Tetrahedron Letters, 36, 5633-5636;
244. (b) Garlaschelli L, Vidari G, Vita-Finzi P. (1996) Fungal metabolites. 41. Tricholomenyns C, D, and E, novel dimeric dienyne geranyl cyclohexenones from the fruiting bodies of Tricholoma acerbum. Tetrahedron Letters, 37, 6223-6226.
245. (a) Baeuerle J, Anke T, Jente R, Bosold F. (1982) Antibiotics from Basidiomycetes. XVI. Antimicrobial and cytotoxic polyines from Mycena viridimarginata Karst. Archives of Microbiology, 132, 194-196;
246. (b) Jente R, Bosold F, Bauerle J, Anke T. (1985) Tetra-acetylenic metabolites from Mycena viridimarginata. Phytochemistry, 24, 553-559.
247. Hautzel R, Anke H, Sheldrick WS. (1990) Mycenon, a new metabolite from a Mycena species TA 87202 (Basidiomycetes) as an inhibitor of isocitrate lyase. Journal of Antibiotics, 43, 1240-1244.
248. (a) Takahashi A, Endo T, Nozoe S. (1992) Repandiol, a new cytotoxic diepoxide from the mushrooms Hydnum repandum and H. repandum var. album. Chemical & Pharmaceutical Bulletin, 40, 3181-3184;
249. (b) Nozoe S, Takahashi A, Endo T. (1993) Preparation of repandiol derivatives as antitumor agents. Japan. Kokai Tokkyo Koho, 8 pp., Japanese Patent: JP 05247017 A2 19930924 Heisei;
250. (c) Conklin JE, Millard JT. (2000) DNA interstrand cross-linking by a diepoxide mycotoxin. Book of Abstracts, 219th ACS National Meeting, San Francisco, CA, March 26-30.
251. Millard JT, Katz JL, Goda J, Frederick ED, Pierce SE, Speed TJ, Thamattoor DM. (2004) DNA interstrand cross-linking by a mycotoxic diepoxide. Biochimie, 86, 419-423.
252. (a) Lee MD, Dunne TS, Siegel MM, Chang CC, Morton GO, Borders DB. (1987) Calichemicins, a novel family of antitumor antibiotics .1. Chemistry and partial structure of calichemicin-gamma-1. Journal of the American Chemical Society, 109, 3464- 3466;
253. (b) Lee MD, Dunne TS, Chang CC, Siegel M, Morton GO, Ellestad GE, McGahren WJ, Borders DB. (1993) The calicheamicins, a family of extremely potent antitumor antibiotics. Youji Huaxue, 13, 166-70;
254. (c) Konishi M, Ohkuma H, Saitoh K, Kawaguchi H, Golik J, Dubay G, Groenewold G, Krishnan B, Doyle TW. (1985) Esperamicins, a novel class of potent antitumor antibiotics. I. Physicochemical data and partial structure. Journal of Antibiotics, 38, 1605-1609.
255. Lee MD, Dunne TS, Chang CC, Ellestad GA, Seigel MM, Morton GO, McGahren WJ, Borders DB. (1987) Calichemicins, a novel family of antitumor antibiotics. 2. Chemistry and structure of calichemicin-1 Journal of the American Chemical Society, 109, 3466-3468.
256. Golik J, Dubay G, Groenwold G, Kawaguchi M, Konishi M, Krishnan B, Ohkuma H, Saitoh K, Doyle TW. (1987) Esperamicins, a novel class of potent antitumor antibiotics. 3. Structures of esperamicins-A1, esperamicin-A2, and esperamicin-A1b. Journal of the American Chemical Society, 109, 3462-3464.
257. Golik J, Clardy J, Dubay G, Groenewold G, Kawaguchi H, Konishi M, Krishnan B, Ohkuma M, Saitoh K, Doyle TW. (1987) Esperamicins, a novel class of potent antitumor antibiotics. 2. Structure of esperamicin-X. Journal of the American Chemical Society, 109, 3461-3462.
258. Lee MD, Ellestad GA, Borders DB. (1991) Calicheamicins - discovery, structure, chemistry, and interaction with DNA. Accounts of Chemical Research, 24, 235-243.
259. Beutler JA, Clark P, Alvarado AB, Golik J. (1994) Esperamicin-P, the tetrasulfide analog of esperamicin-A(1). Journal of Natural Products, 57, 629-633.
260. Konishi M, Ohkuma H, Matsumoto K, Tsuno T, Kamei H, Miyaki T, Oki T, Kawaguchi H, VanDuyne GD, Clardy J. (1989) Dynemicin a, a novel antibiotic with the anthraquinone and 1,5-diyn-3-ene subunit Journal of Antibiotics, 42, 1449-1452.
261. (a) Otani T, Minami Y, Sakawa K, Yoshida K. (1991) Isolation and characterization of non-protein chromophore and its degradation product from antibiotic C-1027. Journal of Antibiotics, 44, 564-568;
262. (b) Hu JL, Xue YC, Xie MY, Zhang R, Otani T, Minami Y, Yamada Y, Marunaka T. (1988) A new macromolecular antitumor antibiotic, C-1027. I. Discovery, taxonomy of producing organism, fermentation and biological activity. Journal of Antibiotics, 41, 1575-1579;
263. (c) Shen B, Liu W, Christenson SD, Standage S. (2000) The Streptomyces globisporus gene cluster encoding enzymes of biosynthesis of the enediyne antitumor antibiotic C-1027. PCT International Application, 160 pp. WO 2000040596 A1 20000713;
264. (e) Hu J, Zhen Y. (1989) Antibiotic C-1027 from Streptomyces for use as a neoplasm inhibitor. Faming Zhuanli Shenqing Gongkai Shuomingshu, 15 pp., Chinese Patent: CN 1037539 A 19891129.
265. Sugimoto Y, Otani T, Oie S, Wierzba K, Yamada Y. (1990) Mechanism of action of a new macromolecular antitumor antibiotic, C-1027 Journal of Antibiotics, 43, 417-421.
266. (a) Zhen Y, Ming X, Yu B, Otani T, Saito H, Yamada, Y. (1989) A new macromolecular antitumor antibiotic, C-1027. III. Antitumor activity. Journal of Antibiotics, 42, 1294-1298;
267. (b) Liu Y-P, Li Q-S, Huang Y-R, Liu C-X. (2005) Tissue distribution and excretion of 125I-lidamycin in mice and rats. World Journal of Gastroenterology, 11, 3281-3284;
268. (c) Liu Y-P, Li Q-S, Huang Y-R, Zhou M-J, Liu C-X. (2005) Pharmacokinetics of C-1027 in mice as determined by TCA-RA method. World Journal of Gastroenterology, 11, 717-720.
269. (a) Edo K, Saito K, Matsuda Y, Akiyamamurai Y, Mizugaki M, Koide Y, Ishida N. (1991) Neocarzinostatin - selective tryptophan oxidation and neocarzinostatin-chromophore binding to apo-neocarzinostatin. Chemical & Pharmaceutical Bulletin, 39, 170-176;
270. (b) Kuromizu K, Maeda H. (1997) Chemical structure of the apoprotein of neocarzinostatin. In: Neocarzinostatin. (Maeda H, Edo K, Ishida N., Es), pp. 3-22., Publisher: Springer, Tokyo, Japan.
271. (a) Myers AG, Proteau PJ, Handel TM. (1988) Stereochemical assignment of neocarzinostatin chromophore - structures of neocarzinostatin Chromophore methyl thioglycolate adducts. Journal of The American Chemical Society, 110, 7212-7214;
272. (b) Kudo K, Suto T, Koide Y, Edo K, Ishida N. (1982) Production of a free chromophore component of neocarzinostatin (NCS) in the culture filtrate of Streptomyces carzinostaticus var. F-41. Journal of Antibiotics, 35, 1111-1115.
273. (a) Koide Y, Ishii F, Hasuda K, Koyama Y, Edo K, Katamine S, Kitame F, Ishida N. (1980) Isolation of a non-protein component and a protein-component from neocarzinostatin (Ncs) and their biological-activities. Journal of Antibiotics, 33, 342-346;
274. (b) Ishida N, Miyazaki K, Kumagai K, Rikimaru M, Kuroya M. (1967) Neocarzinostatin produced by Streptomyces carzinostaticus var neocarzinostaticus. US Patent, 7 pp. US 3334022 19670801;
275. (c) Maeda H, Kumagai K, Ishida N. (1966) Characterization of neocarzinostatin. Journal of Antibiotics, 19, 253-259.
276. (a) Kawata S, Ashizawa S, Hirama M. (1997) Synthetic study of kedarcidin chromophore: Revised structure. Journal of The American Chemical Society, 119, 12012-12013;
277. (b) Hofstead SJ, Matson JA, Malacko AR, Marquardt H. (1992) Kedarcidin, a new chromoprotein antitumor antibiotic. II. Isolation, purification and physico-chemical properties. Journal of Antibiotics, 45, 1250- 1254;
278. (c) Lam KS, Hesler GA, Gustavson DR, Crosswell AR, Veitch JM, Forenza S, Tomita K. (1991) Kedarcidin, a new chromoprotein antitumor antibiotic. I. Taxonomy of producing organism, fermentation and biological activity. Journal of Antibiotics, 44, 472-478.
279. Leet JE, Schroeder DR, Hofstead SJ, Golik J, Colson KL, Huang S, Klohr SE, Doyle TW, Matson JA. (1992) Kedarcidin, a new chromoprotein antitumor antibiotic - structure elucidation of kedarcidin chromophore Journal of The American Chemical Society, 114, 7946-7948;
280. Leet JE, Schroeder DR, Langley DR, Colson KL, Huang S, Klohr SE, Lee MS, Golik J, Hofstead SJ. (1993) Chemistry and structure elucidation of the kedarcidin chromophore. Journal of the American Chemical Society, 115, 8432-8443.
281. (a) Schroeder DR, Colson KL, Klohr SE, Zein N, Langley DR, Lee MS, Matson JA, Doyle TW. (1994) Isolation, structure determination, and proposed mechanism of action for artifacts of maduropeptin chromophore Journal of the American Chemical Society, 116, 9351-9352;
282. (b) Hanada M, Ohkuma H, Yonemoto T, Tomita K, Ohbayashi M, Kamei H, Miyaki T, Konishi M, Kawaguchi H, Forenza S. (1991) Maduropeptin, a complex of new macromolecular antitumor antibiotics. Journal of Antibiotics, 44, 403-414.
283. (a) Ando T, Ishii M, Kajiura T, Kameyama T, Miwa K, Sugiura Y. (1998) A new non-protein enediyne antibiotic N1999A2: Unique enediyne chromophore similar to neocarzinostatin and DNA cleavage feature. Tetrahedron Letters, 39, 6495-6498;
284. (b) Ishii M, Ando T, Kajiura T, Kameyama T, Nihei Y. (1995) Antitumoric antibiotic N1999A2 manufacture with Streptoverticillium. Japan. Kokai Tokkyo Koho, 9 pp. Japanese Patent: JP 07291955 A2 19951107 Heisei;
285. (c) Ando T, Ishii M, Kajiura T, Kameyama T, Miwa K. (1996) Structure of the novel enediyne antibiotic N1999A2. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu, 38, 487-492.
286. (a) Ishida N, Miyazaki K, Kumagai K, Rikimaru M. (1965) Neocarzinostatin an antitumor antibiotic of high molecular weight - isolation physicochemical properties and biological activities Journal of Antibiotics, 18, 68-74;
287. (b) Zein N. (1996) Kedarcidin and maduropeptin, two novel chromoproteins with potent antitumor activities. NATO ASI Series, Series C: Mathematical and Physical Sciences, (DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases), 479, 53-63.
288. (a) Lam KS, Hesler GA, Gustavson DR, Crosswell AR, Veitch JM, Forenza S, Tomita K. (1991) Kedarcidin, a new chromoprotein antitumor antibiotic. 1. Taxonomy of producing organism, fermentation and biological-activity. Journal of Antibiotics, 44, 472- 478;
289. (b) Zein N, Casazza AM, Doyle TW, Leet JE, Schroeder DR, Solomon W, Nadler SG. (1993) Selective proteolytic activity of the antitumor agent kedarcidin. Proceedings of the National Academy of Sciences of the United States of America, 90, 8009-8012.
290. Hanada M, Ohkuma H, Yonemoto T, Tomita K, Ohbayashi M, Kamei H, Miyaki T, Konishi M, Kawaguchi H, Forenza S. (1991) Maduropeptin, a complex of new macromolecular antitumor antibiotics. Journal of Antibiotics (Tokyo), 44, 403-414.
291. Takeshita M, Kappen LS, Grollman AP, Eisenberg M, Goldberg IH. (1981) Strand scission of deoxyribonucleic acid by neocarzinostatin, auromomycin, and bleomycin: studies on base release and nucleotide sequence specificity. Biochemistry, 20, 7599-7606.
292. (a) Galm U, Hager MH, Van Lanen SG, Ju J, Thorson JS, Shen B. (2005) Antitumor antibiotics: bleomycin, enediynes, and mitomycin. Chemical Reviews, 105, 739-758;
293. (b) Shen B, Liu W, Nonaka K. (2003) Enediyne natural products: biosynthesis and prospect towards engineering novel antitumor agents. Current Medicinal Chemistry, 10, 2317-2325;
294. (d) Jones GB, Fouad FS. (2002) Designed enediyne antitumor agents. Current Pharmaceutical Design, 8, 2415-2440;
295. (e) Schreiner PR, Navarro-Vazquez A, Prall M. (2005) Computational studies on the cyclization of enediynes, enyne-allenes, and related polyunsaturated systems. Accounts of Chemical Research, 38, 29-37.