Uv-b absorbing compounds isolated from plants

Abstract

The present invention relates to compounds according to general formula (I) with enhanced absorption of UV-B irradiation. The present invention also relates to an UV-B tolerant plant and a method for enhanced production of compounds according to general formula (I) in a plant or plant cell. Furthermore, the invention relates to a nucleic acid sequence SEQ-ID No.1 encoding FPT2 catalyzing the production of compounds according to general formula (I). The invention further relates to compositions comprising compounds according to general formula (I). Furthermore, the invention relates to a method of conferring UV-B tolerance to a plant as well as an UV-B tolerant plant comprising the nucleic acid sequence SEQ-ID No.1 encoding FPT2 catalyzing the production of compounds according to general formula (I).

1 . A compound of general formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         R 1 , R 2  and R 3  are independently of each other selected from: —H, —OH, and —OCH 3 ; 
         R 4  is selected from —H, —OH, and —OCH 3 ; 
         R 5  represents —H, 
       
       
         
           
           
               
               
           
         
         and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof. 
       
     
     
         2 . The compound according to  claim 1  of general formula (II) 
       
         
           
           
               
               
           
         
         wherein 
         R 4  is selected from —H, —OH, and —OCH 3 ; 
         R 5  represents —H or 
       
       
         
           
           
               
               
           
         
         and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof. 
       
     
     
         3 . The compound according to  claim 1  of general formula (III) 
       
         
           
           
               
               
           
         
         wherein 
         R 4  is selected from —H, —OH, and —OCH 3 ; 
         R 5  represents —H or 
       
       
         
           
           
               
               
           
         
         and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof. 
       
     
     
         4 . The compound according to  claim 1  of general formula (IV) 
       
         
           
           
               
               
           
         
         wherein 
         R 4  is selected from —H, —OH, and —OCH 3 ; 
         R 5  represents —H or 
       
       
         
           
           
               
               
           
         
         and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof. 
       
     
     
         5 . The compound according to  claim 1  selected from the group consisting of: Saiginol A*, Saiginol B*, Saiginol C*, Saiginol G*, Saiginol H*, Saiginol I*, Saiginol M*, Saiginol N*, Saiginol O*, Saiginol A, Saiginol B, Saiginol C, Saiginol D, Saiginol E, Saiginol F, Saiginol G, Saiginol H, Saiginol I, Saiginol J, Saiginol K, Saiginol L, Saiginol M, Saiginol N, Saiginol O, Saiginol P, Saiginol Q, and Saiginol R. 
     
     
         6 . A method for the preparation of at least one compound according to  claim 1  using an UV-B tolerant plant comprising a nucleic acid encoding a polypeptide that is suitable to synthesize a compound according to  claim 1  and wherein said nucleic acid has been introduced into the UV-B tolerant plant by genetic manipulation. 
     
     
         7 . A nucleic acid sequence which has at least 80% sequence identity to SEQ-ID No.1, wherein the nucleic acid sequence encodes a polypeptide having phenylacyltransferase activity. 
     
     
         8 . A vector comprising the nucleic acid sequence according to  claim 7 . 
     
     
         9 . The vector according to  claim 8 , wherein the vector is an expression vector. 
     
     
         10 . A method of conferring UV-B tolerance to a plant, wherein the method comprises the steps of:
 (i) transforming a recipient plant with the nucleic acid according to  claim 6 ;   (ii) producing one or more transgenic offspring of the recipient plant; and   (iii) selecting the offspring for UV-B tolerance.   
     
     
         11 . An UV-B tolerant plant comprising the nucleic acid according to  claim 6  that synthesizes a compound according to  claim 1  and wherein the nucleic acid according to  claim 6  has been introduced into the UV-B tolerant plant by genetic manipulation. 
     
     
         12 - 13 . (canceled) 
     
     
         14 . A sunscreen composition comprising the compound according to  claim 1 . 
     
     
         15 - 17 . (canceled) 
     
     
         18 . An UV-B tolerant plant comprising the nucleic acid according to  claim 7  that synthesizes a compound according to  claim 1  and wherein the nucleic acid according to  claim 7  has been introduced into the UV-B tolerant plant by genetic manipulation. 
     
     
         19 . A method of conferring UV-B tolerance to a plant, wherein the method comprises the steps of:
 (i) transforming a recipient plant with the nucleic acid according to  claim 7 ;   (ii) producing one or more transgenic offspring of the recipient plant; and   (iii) selecting the offspring for UV-B tolerance.