Structure-Activity Relationship of Triterpenes and Triterpenoid Glycosides against Tobacco Mosaic Virus

Abstract

A new activity of triterpenes and triterpenoid glycosides against phytovirus has been found. Based on the anti-TMV replication activity in vivo, 47 triterpenes and triterpenoid glycosides were screened through the leaf-disk method together with indirect ELISA. Structure-activity relationships were analyzed according to the results of bio-activity screening. Besides, the EC₅₀ values of those compounds having higher activities were measured.

Abbreviations

Cpd(s):compound(s)

DMSO:dimethyl sulfoxide

EC₅₀:median effective concentration

ELISA:enzyme linked immunosorbent assay

SAR:structure-activity relationship

TMV:tobacco mosaic virus

Key words

Structure-activity relationship - triterpenes - triterpenoid glycosides - tobacco mosaic virus (TMV) - EC₅₀

References

• 1 Cheplick S M, Agrios G N. Effect of injected antiviral compounds on apple mosaic, scar skin and dapple apple disease of apple trees.  Plant Dis. 1983;  67 1130-3.
• 2 French C J, Nell T. Inhibition of infectivity of potato virus X by flavonoids.  Phytochemistry. 1992;  31 3017-20.
• 3 Connolly J D, Hill R A. Triterpenoids.  Nat Prod Rep. 2000;  17 463-82.
• 4 Connolly J D, Hill R A. Triterpenoids.  Nat Prod Rep. 2001;  18 560-78.
• 5 Connolly J D, Hill R A. Triterpenoids.  Nat Prod Rep. 2001;  18 131-47.
• 6 Connolly J D, Hill R A. Triterpenoids.  Nat Prod Rep. 2002;  19 494-513.
• 7 Connolly J D, Hill R A. Triterpenoids.  Nat Prod Rep. 2005;  22 230-48.
• 8 Wu Z J, Ouyang M A, Wang C Zh, Zhang Z hK, Shen J G. Anti- tobacco mosaic virus (TMV) triterpenoid saponins from the leaves of leaves of Ilex oblonga .  J Agric Food Chem. 2007;  55 1712-7.
• 9 Wu Z J, Ouyang M A, Wang C Zh, Zhang Z hK. Six new triterpenoid saponins from the leaves of Ilex oblonga and their inhibitory activities against TMV replication.  Chem Pharm Bull. 2007;  55 422-7.
• 10 Padgett H S, Beachy R N. Analysis of a tobacco mosaic virus strain capable of overcoming N gene-mediated resistance.  Plant Cell. 1993;  5 577-86.
• 11 Ouyang M A, Yang C R, Chen Z L, Wang H Q. Triterpenes and triterpenoid glycosides from the leaves of Ilex kudincha .  Phytochemistry. 1996;  41 871-7.
• 12 Ouyang M A, Wang H Q, Chen Z L, Yang C R. Triterpenoid glycosides from Ilex kudincha .  Phytochemistry. 1996;  43 443-5.
• 13 Ouyang M A, Wang H Q, Yang C R. Triterpenoid saponins from the leaves of Ilex kudincha .  J Asian Nat Prod Res. 2001;  3 31-42.
• 14 Ouyang M A, Wang H Q, Su J H. Triterpene esters and triterpenes from Ilex kudincha .  Chin Nat Prod Res Dev. 1997;  9 19-23.
• 15 Kitagawa I. Soil bacterial hydrolysis leading to genuine aglycone. III. The structures of glycosides and genuine aglycone of sanguisorbae radix.  Chem Pharm Bull. 1971;  19 1700-7.
• 16 Ouyang M A, Wang H Q, Liu Y Q, Yang C R. Triterpenoid saponins from the leaves of Ilex latifolia .  Phytochemistry. 1997;  45 1501-5.
• 17 Ouyang M A. Glycosides from the leaves of Ilex hylonoma .  Nat Prod Res. 2003;  17 183-8.
• 18 Ouyang M A, Liu Y Q, Wang H Q, Yang C R. Triterpenoid saponins from Ilex latifolia .  Phytochemistry. 1998;  49 2483-6.
• 19 Amimoto K, Yoshikawa K, Arihara S. Triterpenoid saponins of aquifoliaceous plants. VIII. Ilexosides XXIX - XXXII from the leaves of Ilex rotunda THUNB.  Chem Pharm Bull. 1992;  40 3138-41.
• 20 Gao F, Chen F H, Tanaka T, Tanaka O. 19α-Hydroxyursane-type glucosyl esters from the roots of Rubus suavissimus S. Lee.  Chem Pharm Bull. 1985;  33 37-9.
• 21 Ouyang M A, Zhang X, Li D P. Aculeoside I, a novel 18,19-seco-ursane saponin isolated from Ilex aculeolata .  Nat Prod Lett. 2002;  16 137-41.
• 22 Kojima H, Ogura H. Triterpenoids from Prunella vulgaris .  Phytochemistry. 1986;  25 729-33.
• 23 Ouyang M A. Glycosides from the leaves of Ilex latifolia .  Chin J Chem. 2001;  9 885-92.
• 24 Qing W J, Zhao J J. Chemical constituents from Ilex cornuta .  Zhongcaoyao. 1988;  19 2-8.
• 25 Ouyang M A, Wu C L. Three new saponins from the leaves of Ilex hylonoma .  J Asian Nat Prod Res. 2003;  5 89-94.
• 26 Yang C R, Jiang Z D, Wu M Z, Zhou J, Tanaka O. Studies on saponins of rhizomes of Panax zingiberensis Wu et Feng.  Acta Pharm Sin. 1989;  19 232-6.
• 27 Takabe S, Takeda T, Chen Y J, Ogihara Y. Triterpenoid glycosides from the roots of Tetrapanax papyriferum K. Koch. III: Structures of four new saponins.  Chem Pharm Bull. 1985;  33 4701-6.
• 28 Ouyang M A, Li D P. Four new triterpenoid saponins from Ilex godajam .  J Asian Nat Prod Res. 2002;  4 25-31.
• 29 Annaev C h, Isamukhmedov M, Abubakirov N K. Triterpene glycosides of Climacoptera transoxana .  Chem Nat Comp. 1983;  4 202-5.