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DOI: 10.1055/s-2006-947189
Diterpenes from ”Pini Resina” and their Preferential Cytotoxic Activity under Nutrient-Deprived Condition
Publikationsverlauf
Received: March 12, 2006
Accepted: June 1, 2006
Publikationsdatum:
10. August 2006 (online)
Abstract
In the course of our search for anticancer agents based on a novel anti-austerity strategy, we found that the 70 % EtOH extract of ”Pini Resina” showed 100 % preferential cytotoxicity at the concentration of 50 μg/mL. Further bioassay-guided fractionation and purification led to the isolation of 15 compounds including one new compound 7-oxo-13α-hydroxyabiet-8(14)-en-18-oic acid (1). Their structures were elucidated on the basis of spectroscopic analysis. Among the isolated compounds, methyl abieta-8,11,13-trien-18-oate (7) showed the most potent preferential cytotoxicity at 10 μg/mL under nutrient-deprived condition.
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References
- 1 Li D, Xie K, Wolff R, Abbruzzese J L. Pancreatic cancer. Lancet. 2004; 363 1049-57
- 2 Shore S, Vimalachandran D, Raraty M GT, Ghaneh P. Cancer in the elderly: pancreatic cancer. Surg Oncol. 2004; 13 201-10
- 3 Izushi K, Kato K, Ogura T, Kinoshita T, Esumi H. Remarkable tolerance of tumor cells to nutrient deprivation: possible new biochemical target for cancer therapy. Cancer Res. 2000; 60 6201-7
- 4 Awale S, Lu J, Kalauni S K, Kurashima Y, Tezuka Y, Kadota S. et al . Identification of arctigenin as an antitumor agent having the ability to eliminate the tolerance of cancer cells to nutrient starvation. Cancer Res. 2006; 66 1751-7
- 5 Awale S, Nakashima E MN, Kalauni S K, Tezuka Y, Kurashima Y, Lu J. et al . Angelmarin, a novel anti-cancer agent able to eliminate the tolerance of cancer cells to nutrient starvation. Bioorg Med Chem Lett. 2006; 16 581-3
- 6 Lu J, Kunimoto S, Yamazaki Y, Kaminishi M, Esumi H. Kigamicin D, a novel anticancer agent based on a new anti-austerity strategy targeting cancer cells’ tolerance to nutrient starvation. Cancer Sci. 2004; 95 547-52
- 7 Zinkel D, Russel J. Naval stores: production, chemistry, utilization. In: Zinkel D, Russel J, editors Atlanta; Pine Chemicals Association 1989
- 8 Usmanghani K, Saeed A, Alam M T. Indusynic Medicine. In: Usmanghani K, editor 1st edition A-952. Karachi; Research Institute of Indusyunic Medicine 1997: p 338-9
- 9 William M C. Non-wood forest products from conifers. Rome; FAO-Food and Agriculture Organization of the United Nations 1995: p 1-15
- 10 Namba T. Coloured illustrations of Wakan-Yaku (The crude drugs in Japan, China and the neighbouring countries). In: Namba T, editor Vol II Osaka; Hoikusha Publishing Co, Ltd 1980: p 24-5
- 11 Ruzicka L, Sternbach L. Zur Kenntnis der Diterpene. Helv Chim Acta. 1940; 23 341-55
- 12 Darling T R, Turro N J. Carbon-13 nuclear magnetic resonances spectroscopy of naturally occurring substances. X. Pimaradienes. J Am Chem Soc. 1972; 94 4367-9
- 13 Ayer W A, Macaulay J B. Metabolites of the honey mushroom, Armillaria mellea . Can J Chem. 1987; 65 7-13
- 14 Bol’shakova V I, Shmidt E N, Pentegova V A, Mamatyuk V I. Minor constituents of the resin of the Kurile Dahurian, Japanese and Siberian larches. Khim Prir Soedin. 1986; 5 571-6
- 15 Erdtman H, Malmborg L. The Beckmann rearrangement of the oxime of 7-ketodehydroabietate. A side reaction. Acta Chem Scand. 1970; 24 2252
- 16 Chamy M C, Piovano M, Gambaro V, Garbarino J A, Nicoletti M. Dehydroabietane diterpenoids from Calceolaria ascendens . Phytochemistry. 1987; 26 1763-5
- 17 Cheung H TA, Miyase T, Lenguyen M P, Smal M A. Further acidic and neutral components of Pinus massoniana Resin. Tetrahedron. 1993; 49 7903-15
- 18 Kinouchi Y, Ohtsu H, Tokuda H, Nishino H, Matsunaga S, Tanaka R. Potential antitumor-promoting diterpenoids from the stem bark of Picea glehni . J Nat Prod. 2000; 63 817-20
- 19 Ohtsu H, Tanaka R, In Y, Matsunaga S, Tokuda H, Nishino H. Abietane diterpenoids from the cones of Larix kaempferi and their inhibitory effects on Epstein-Barr virus activation. Planta Med. 2001; 67 55-60
- 20 Tanaka R, Ohtsu H, Matsunaga S. Abietane diterpene acids and other constituents from the leaves of Larix kaempferi . Phytochemistry. 1997; 46 1051-7
- 21 Roshchin V I, Kolodynskaya L A, Raldugin V A. Abietic and dehydroabietic acid derivatives from the needle-free shoots of Pinus sylvestris . Khim Prir Soedin. 1985; 3 345-51
Dr. Prof. Shigetoshi Kadota
Institute of Natural Medicine
University of Toyama
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Japan
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