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.
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
2630 Sugitani
Toyama 930-0194
Japan
Phone: +81-76-434-7625
Fax: +81-76-434-5059
Email: kadota@ms.toyama-mpu.ac.jp