New Monoterpenes, Diterpenes, and Lignans from Abies recurvata

Abstract

From the aerial part of Abies recurvata, 62 miscellaneous chemical constituents were isolated including 6 new and 56 known ones. The new compounds comprised three monoterpenes, two diterpenes, and one lignan. Their chemical structures were characterized on the basis of various spectroscopic techniques. Dihydrodehydrodiconiferyl alcohol (35) showed the strongest inhibitory effects against lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells with an IC₅₀ value of 66.4 µM.

Key words

Abies recurvate - Pinaceae - monoterpenes - diterpenes - lignin - nitric oxide - lipopolysaccharide

• References

• 1 Yang XW, Li SM, Shen YH, Zhang WD. Phytochemical and biological studies of Abies species. Chem Biodivers 2008; 5: 56-81
• 2 Yu P, Zhang SD, Li YL, Yang XW, Zeng HW, Li HL, Zhang WD. Abieseconordines A and B, two novel norditerpenoids with a 18-nor-5,10; 9,10-diseco-abietane skeleton from Abies forrestii . Helv Chim Acta 2012; 95: 415-422
• 3 Xia JH, Zhang SD, Li YL, Wu L, Zhu ZJ, Yang XW, Zeng HW, Li HL, Wang N, Steinmetz A, Zhang WD. Sesquiterpenoids and triterpenoids from Abies holophylla and their bioactivities. Phytochemistry 2012; 74: 178-184
• 4 Yang XW, Li YL, Li SM, Shen YH, Tian JM, Zhu ZJ, Feng L, Wu L, Lin S, Wang N, Liu Y, Zhang WD. Mono- and sesquiterpenoids, flavonoids, lignans, and other miscellaneous compounds of Abies georgei . Planta Med 2011; 77: 742-748
• 5 Ou-Yang DW, Wu L, Li YL, Yang PM, Kong DY, Yang XW, Zhang WD. Miscellaneous terpenoid constituents of Abies nephrolepis and their moderate cytotoxic activities. Phytochemistry 2011; 72: 2197-2204
• 6 Li YL, Wu L, Ou-Yang DW, Yu P, Xia JH, Pan YX, Yang XW, Zeng HW, Cheng XR, Jin HZ, Zhang WD. Phenolic compounds of Abies nephrolepis and their NO production inhibitory activities. Chem Biodivers 2011; 8: 2299-2309
• 7 Yang XW, Li SM, Wu L, Li YL, Feng L, Shen YH, Tian JM, Tang J, Wang N, Liu Y, Zhang WD. Abiesatrines A–J: anti-inflammatory and anti-tumor triterpenoids from Abies georgei Orr. Org Biomol Chem 2010; 8: 2609-2616
• 8 Yang XW, Li SM, Li YL, Wu L, Xia JH, Shen YH, Tian JM, Wang N, Liu YH, Zhang WD. Abiespiroside A, an unprecedented sesquiterpenoid spirolactone with a 6/6/5 ring system from Abies delavayi . Eur J Org Chem 2010; 2010: 6531-6534
• 9 Wu L, Li YL, Li SM, Yang XW, Xia JH, Zhou L, Zhang WD. Systematic phytochemical investigation of Abies spectabilis . Chem Pharm Bull 2010; 58: 1646-1649
• 10 Yang XW, Ding Y, Li XC, Ferreira D, Shen YH, Li SM, Wang N, Zhang WD. Cycloabiesesquine A, a unique sesquiterpenoid from Abies delavayi . Chem Commun 2009; 3771-3773
• 11 Li YL, Yang XW, Li SM, Tang J, Tian JM, Peng XY, Huang DS, Zhang WD. Two new spirobiflavonoids from Abies chensiensis with moderate NO production inhibitory activity. Planta Med 2009; 75: 1534-1537
• 12 Li YL, Yang XW, Li SM, Shen YH, Zeng HW, Liu XH, Tang J, Zhang WD. Terpenoid constituents of Abies chensiensis with potential anti-inflammatory activity. J Nat Prod 2009; 72: 1065-1068
• 13 Yang XW, Li SM, Feng L, Shen YH, Tian JM, Zeng HW, Liu XH, Shan L, Su J, Zhang C, Zhang WD. Abiesanol A, a novel biflavanol with unique six connective hexacyclic rings isolated from Abies georgei . Tetrahedron Lett 2008; 49: 3042-3044
• 14 Yang XW, Li SM, Feng L, Shen YH, Tian JM, Liu XH, Zeng HW, Zhang C, Zhang WD. Abiesanordines A–N: fourteen new norditerpenes from Abies georgei. Tetrahedron 2008; 64: 4354-4362
• 15 Yang XW, Feng L, Li SM, Liu XH, Li YL, Wu L, Shen YH, Tian JM, Zhang X, Liu XR, Wang N, Liu Y, Zhang WD. Isolation, structure, and bioactivities of abiesadines A–Y, 25 new diterpenes from Abies georgei Orr. Bioorg Med Chem 2010; 18: 744-754
• 16 Zheng WJ, Fu LG. Pinaceae. In: Wu ZY, editor Flora of China, Vol. 7. Beijing: Science Press; 1978: 94-95
• 17 Yang XW, Zeng HW, Liu XH, Li SM, Xu W, Shen YH, Zhang C, Zhang WD. Anti-inflammatory and anti-tumour effects of Abies georgei extracts. J Pharm Pharmacol 2008; 60: 937-941
• 18 Jiang L, Kojima H, Yamada K, Kobayashi A, Kubota K. Isolation of some glycosides as aroma precursors in young leaves of Japanese pepper (Xanthoxylum piperitum DC.). J Agric Food Chem 2001; 49: 5888-5894
• 19 Matsuda N, Satao H, Yaoita Y, Kikuchi M. Isolation and absolute structures of the neolignan glycosides with the enantimetric aglycones from the leaves of Viburnum awabuki K. Koch. Chem Pharm Bull 1996; 44: 1122-1123