Two New Spirobiflavonoids from Abies chensiensis with Moderate NO Production Inhibitory Activity

Abstract

Phytochemical investigation of the aerial parts of Abies chensiensis afforded two new (compounds 2 and 3) and 27 known compounds, including the related compound larixinol (1). The structures of spirobiflavonoids 1–3 were established using 1D and 2D NMR spectroscopic techniques. In addition, the structure of larixinol (1) was confirmed by X-ray crystallographic analysis. Compounds 1–3 were evaluated for inhibitory activities against LPS-induced NO production in macrophages. Larixinol (1) showed moderate effects, with an IC₅₀ value of 60.0 µg/mL. In addition, it did not show any cytotoxicity on RAW 264.7 macrophages at 100 µg/mL.

Key words

Abies chensiensis - Pinaceae - spirobiflavonoids - larixinol - RAW 264.7 macrophages - NO

References

• 1 Yang X W, Li S M, Shen Y H, Zhang W D. Phytochemical and biological studies of Abies species.  Chem Biodivers. 2008;  5 56-81
• 2 Yang X W, Li S M, Feng L, Shen Y H, Tian J M, Liu X H, Zeng H W, Zhang C, Zhang W D. Abiesanordines A−N: fourteen new norditerpenes from Abies georgei.  Tetrahedron. 2008;  64 4354-4362
• 3 Yang X W, Li S M, Feng L, Shen Y H, Tian J M, Zeng H W, Liu X H, Shan L, Su J, Zhang C, Zhang W D. Abiesanol A, a novel biflavanol with unique six connective hexacyclic rings isolated from Abies georgei.  Tetrahedron Lett. 2008;  19 3042-3044
• 4 Li Y L, Yang X W, Zhang W D. Stilbenes, lignans, and phenols from Abies chensiensis.  Biochem Syst Ecol. 2008;  36 932-934
• 5 Li Y L, Yang X W, Li S M, Shen Y H, Zeng H W, Liu X H, Tang J, Zhang W D. Terpenoid constituents of Abies chensiensis.  J Nat Prod. , advance online publication 2009;  DOI: 10.1021/np800790h
• 6 Min K R, Hwang B Y, Lim H S, Kang B S, Oh G J, Lee J, Kang S H, Lee K S, Ro J S, Kim Y. (−)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus.  Planta Med. 1999;  65 460-462
• 7 Shen Z, Haslam E, Falshaw C P, Begley M J. Procyanidins and polyphenols of Larix gmelini bark.  Phytochemistry. 1986;  25 2629-2635
• 8 Wagner H, Chari V M, Sonnenbichler J. ¹³C‐NMR-Spektren natürlich vorkommender Flavonoide.  Tetrahedron Lett. 1976;  17 1799-1802
• 9 Wada H, Satake T, Murakami T, Kojima T, Saiki Y, Chen C M. Chemische und chemotaxonomische Untersuchungen der Pterophyten. LIX. Chemische Untersuchungen der Inhaltsstoffe von Alsophila spinulosa TRYON.  Chem Pharm Bull. 1985;  33 4182-4187
• 10 Shen Z, Theander O. Flavonoid glycosides from needles of Pinus massoniana.  Phytochemistry. 1985;  24 155-158
• 11 Sudjaroen Y, Haubner R, Würtele G, Hull W E, Erben G, Spiegelhalder B, Changbumrung S, Bartsch H, Owen R W. Isolation and structure elucidation of phenolic antioxidants from Tamarind (Tamarindus indica L.) seeds and pericarp.  Food Chem Toxicol. 2005;  43 1673-1682
• 12 Shen C C, Chang Y S, Ho L K. Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids.  Phytochemistry. 1993;  34 843-845
• 13 Cai H, Wang M CJ. Chemical constituents from the roots of Begonia fimbristipulata Hance.  Chin J Appl Environ Biol. 1999;  5 103-105
• 14 Min K R, Hwang B Y, Lim H S, Kang B S, Oh G J, Lee J, Kang S H, Lee K S, Ro J S, Kim Y. (−)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus. .  Planta Med. 1999;  65 460-462
• 15 Nilsson M. Chalcones from the fronds of Pityrogramma chrysophylla, var. heyderi.  Acta Chem Scand. 1961;  15 211-212
• 16 Lv Y Z, Wang Y L, Lou Z X, Zu J Y, Liang H Q, Zhou Z L. The isolation and structural determination of naringenin and choerospondin from the bark of Choerospondias axillaris.  Acta Pharm Sin. 1983;  18 199-202
• 17 Zou H Y, Tu P F. Study on flavonoids from Lysimachia clethroides.  Chin J Nat Med. 2004;  2 59-61
• 18 Wollenweber E, Rüidiger W, Dörr M, Lang G, Stevens J F. C-Methyl-favonoids from the leaf waxes of some Myrtaceae.  Phytochemistry. 2000;  55 965-970
• 19 Seidel V, Bailleul F, Waterman P G. (Rel)-1β,2α-di-(2,4-dihydroxy-6-methoxybenzoyl)-3β,4α-di-(4-methoxyphenyl)-cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii.  Phytochemistry. 2000;  55 439-446
• 20 Markham K R, Ternai B, Stanley R, Geiger H, Mabry T J. Carbon-13 NMR studies of flavonoids III : naturally occurring flavonoid glycosides and their acylated derivatives.  Tetrahedron. 1978;  34 1389-1397
• 21 Matthes H WD, Luu B, Ourisson G. Cytotoxic components of Zingiber zerumbet, Curcuma zedoaria and C. domestica.  Phytochemistry. 1980;  19 2643-2650
• 22 Liu H, Orjala J, Sticher O, Rali T. Acylated flavonol glycosides from leaves of Stenochlaena palustris.  J Nat Prod. 1999;  62 70-75
• 23 Bloor S J. An antimicrobial kaempferol-diacyl-rhamnoside from Pentachondra pumila.  Phytochemistry. 1995;  38 1033-1035
• 24 Looker J H, Fisher M S. Synthesis and characterization of the naturally occurring monocyclic pyrone glucosides.  J Carbohydr Chem. 1985;  4 381-392
• 25 Yoshikawa M, Sugimoto S, Nakamura S, Matsuda H. Medicinal flowers. XXII Structures of chakasaponins V and VI, chakanoside I, and chakaflavonoside A from flower buds of Chinese tea plant (Camellia sinensis).  Chem Pharm Bull. 2008;  56 1297-1303
• 26 Teguo P W, Decendit A, Vercauteren J, Deffieux G, Mérillon J M. Trans-resveratrol-3-O-β-glucoside (piceid) in cell suspension cultures of Vitis vinifera.  Phytochemistry. 1996;  42 1591-1593
• 27 Harrison L J, Sia G L, Sim K Y, Tan H TW, Connolly J D, Lavaud C, Massiot G. A ferulic acid ester of sucrose and other constituents of Bhesa paniculata.  Phytochemistry. 1995;  38 1497-1500
• 28 Yang X W, Zeng H W, Liu X H, Li S M, Xu W, Shen Y H, Zhang C, Zhang W D. Anti-inflammatory and anti-tumour effects of Abies georgei extracts.  J Pharm Pharmacol. 2008;  60 937-941