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

 

 Buy Article Permissions and Reprints

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.

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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 4 Li Y L, Yang X W, Zhang W D. Stilbenes, lignans, and phenols from Abies chensiensis.  Biochem Syst Ecol. 2008;  36 932-934
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 7 Shen Z, Haslam E, Falshaw C P, Begley M J. Procyanidins and polyphenols of Larix gmelini bark.  Phytochemistry. 1986;  25 2629-2635
  CrossrefPubMedGoogle Scholar
• 8 Wagner H, Chari V M, Sonnenbichler J. ¹³C‐NMR-Spektren natürlich vorkommender Flavonoide.  Tetrahedron Lett. 1976;  17 1799-1802
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 10 Shen Z, Theander O. Flavonoid glycosides from needles of Pinus massoniana.  Phytochemistry. 1985;  24 155-158
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 12 Shen C C, Chang Y S, Ho L K. Nuclear magnetic resonance studies of 5,7-dihydroxyflavonoids.  Phytochemistry. 1993;  34 843-845
  CrossrefPubMedGoogle Scholar
• 13 Cai H, Wang M CJ. Chemical constituents from the roots of Begonia fimbristipulata Hance.  Chin J Appl Environ Biol. 1999;  5 103-105
  PubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 15 Nilsson M. Chalcones from the fronds of Pityrogramma chrysophylla, var. heyderi.  Acta Chem Scand. 1961;  15 211-212
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 17 Zou H Y, Tu P F. Study on flavonoids from Lysimachia clethroides.  Chin J Nat Med. 2004;  2 59-61
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 21 Matthes H WD, Luu B, Ourisson G. Cytotoxic components of Zingiber zerumbet, Curcuma zedoaria and C. domestica.  Phytochemistry. 1980;  19 2643-2650
  CrossrefPubMedGoogle Scholar
• 22 Liu H, Orjala J, Sticher O, Rali T. Acylated flavonol glycosides from leaves of Stenochlaena palustris.  J Nat Prod. 1999;  62 70-75
  CrossrefPubMedGoogle Scholar
• 23 Bloor S J. An antimicrobial kaempferol-diacyl-rhamnoside from Pentachondra pumila.  Phytochemistry. 1995;  38 1033-1035
  CrossrefPubMedGoogle Scholar
• 24 Looker J H, Fisher M S. Synthesis and characterization of the naturally occurring monocyclic pyrone glucosides.  J Carbohydr Chem. 1985;  4 381-392
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar

Dr. Wei-Dong Zhang

Department of Natural Product Chemistry
School of Pharmacy
Second Military Medical University

325 Guohe Road

Shanghai 200433

People's Republic of China

Phone: + 86 21 81 87 12 44

Fax: + 86 21 81 87 12 44

Email: wdzhangy@hotmail.com

Dr. Xian-Wen Yang

Key Laboratory of Marine Bio-resources Sustainable Utilization
South China Sea Institute of Oceanology
Chinese Academy of Sciences

164 West Xingang Road

Guangzhou 510301

People's Republic of China

Phone: + 86 20 89 02 31 74

Fax: + 86 21 84 45 16 72

Email: yangxw76@163.com

• Supplementary Material