RSS-Feed abonnieren
DOI: 10.1055/s-2008-1034321
© Georg Thieme Verlag KG Stuttgart · New York
Labdane-Type Diterpenes Active against Acne from Pine Cones (Pinus densiflora)
Publikationsverlauf
Received: November 2, 2007
Revised: January 20, 2008
Accepted: January 22, 2008
Publikationsdatum:
07. März 2008 (online)
Abstract
Bioassay-guided extraction and fractionation of the aqueous methanolic extract of the cones of Pinus densiflora (Pinaceae) afforded one new labdane-type diterpene aldehyde, 15-nor-14-oxolabda-8(17),12E-diene-18-oic acid, along with eight known diterpenes. Their structures were elucidated using spectroscopic methods as well as by comparison with previously reported data. The isolates showed antibacterial (Propionibacterium acnes) and antifungal activities.
Key words
Propionibacterium acnes - Pinus densiflora - Pinaceae - antimicrobial activity - labdane
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Eady E A, Ingham E. Propionibacterium acnes - friend or foe?. Rev Med Microbiol. 1994; 5 163-73
- 2 Rahman M AA, Cho S C, Song J, Mun H T, Moon S S. Dendrazawaynes A and B, antifungal polyacetylenes from Dendranthema zawadskii (Asteraceae). Planta Med. 2007; 73 1089-94
- 3 Kim Y S, Shin D H. Volatile components and antibacterial effects of pine needle (Pinus densiflora S. and Z.) extracts. Food Microbiol. 2005; 22 37-45
- 4 Jung M J, Chung H Y, Choi J H, Choi J S. Antioxidant principles from the needles of red pine, Pinus densiflora. Phytother Res. 2003; 17 1064-8
- 5 Zinkel D F. Diterpene resin acids of Pinus densiflora needles and cortex. Phytochemistry. 1976; 15 1073-4
- 6 Kobayashi M, Ishida K, Terabayashi S, Mitsuhashi H. 10-Hydroxypheophytins and a new norlabdane diterpene from the leaves of Cupressus funebris ENDL. Chem Pharm Bull. 1991; 39 3348-9
- 7 Bohlmann F, Alder A, King R M, Robinson H. Ent-labdanes from Mikania alvimii. . Phytochemistry. 1982; 21 173-6
- 8 Minami T, Wada S, Tokuda H, Tanabe G, Muraoka O, Tanaka R. Potential antitumor-promoting diterpenes from the cones of Pinus luchuensis. . J Nat Prod. 2002; 65 921-3
- 9 Hsieh Y L, Fang J M, Cheng Y S. Terpenoids and flavonoids from Pseudotsuga wilsoniana. . Phytochemistry. 1998; 47 845-50
- 10 Iwamoto M, Ohtsu H, Matsunaga S, Tanaka R. Labdane-type diterpenes and a nordrimane-type sesquiterpene from the stem bark of Thuja standishii. . J Nat Prod. 2000; 63 381-3
- 11 Sy L K, Brown G D. Abietane diterpenes from Illicium angustisepalum. . J Nat Prod. 1998; 61 907-12
- 12 Li Y C, Kuo Y H. Five new diterpenes from the wood of Cunninghamia konishii. . J Nat Prod. 1998; 61 997-1000
- 13 Du J, Wang M L, Chen R Y, Yu D Q. Two new bislabdane-type diterpenoids and three new diterpenoids from the roots of Cunninghamia lanceolata. . Planta Med. 2001; 67 542-7
- 14 van Beek T AB, Claassen F W, Dorado J, Godejohann M, Sierra-Alvarez R, Wijnberg J BPA. Fungal biotransformation products of dehydroabietic acid. J Nat Prod. 2007; 70 154-9
- 15 Lee C K, Fang J M, Cheng Y S. Norditerpenes from Juniperus chinensis. . Phytochemistry. 1995; 39 391-4
- 16 Woldemichael G M, Wachter G, Singh M P, Maiese W M, Timmermann B N. Antibacterial diterpenes from Calceolaria pinifolia. J Nat Prod. 2003; 66 242-6
- 17 Tanaka R, Ohtsu H, Matsunaga S. Abietane diterpene acids and other constituents from the leaves of Larix kaempferi. . Phytochemistry. 1997; 46 1051-7
- 18 Ayer W A, Macaulay J B. Metabolites of the honey mushroom, Armillaria mellea. . Can J Chem. 1987; 65 7-14
- 19 Zelnik R, Rabenhorst E, Haider A, Lauterwein J, Wyler H. Photosensitized oxygenation of abieta-7,9(11)-dien-13β-ol. Helv Chim Acta. 1983; 66 780-8
- 20 Gigante B, Silva A M, Curto M JM, Feio S S, Roseiro J, Reis L V. Structural effects on the bioactivity of dehydroabietic acid derivatives. Planta Med. 2002; 68 680-4
Prof. Dr. Surk-Sik Moon
Department of Chemistry
Kongju National University
Kongju 314-701
Korea
Telefon: +82-41-850-8495
Fax: +82-41-850-8479
eMail: ssmoon@kongju.ac.kr
- www.thieme-connect.de/ejournals/toc/plantamedica