# US 11,306,118 B2 · UV-B absorbing compounds isolated from plants

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- Number: US 11,306,118 B2
- Document ID: US11306118B2
- Status: Granted
- Kind: B2
- Application number: 16/592,975
- Filed: 2019-10-04
- Published: 2020-03-12
- Granted: 2022-04-19
- Earliest claimed: 2015-06-09
- Assignees: Max-Planck-Gesellschaft zur Forderung der Wissenschaften e.V.
- Applicants: Max-Planck-Gesellschaft Zur FöRderung Der Wissenschaften E.V.
- Inventors: Alisdair R. Fernie; Takayuki Tohge; Regina Wendenburg; Hirofumi Ishihara; Ronan Sulpice; Mark Stitt
- Web page: https://patentgrep.com/patent/US11306118B2

## CPC

- C07H 17/07: Benzo[b]pyran-4-ones
- A61K 8/60: Sugars; Derivatives thereof
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- C07H 21/04: with deoxyribosyl as saccharide radical
- C12N 9/1029: {transferring groups other than amino-acyl groups (2.3.1)}
- C12N 15/8271: {for stress resistance, e.g. heavy metal resistance}
- C12Q 1/68: involving nucleic acids
- C12Q 1/6895: for plants, fungi or algae
- C12Q 2600/13: Plant traits
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12Q: MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS (immunoassay G01N33/53); COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES

## 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).

## Claims

### Claim 1

A transgenic UV-B tolerant Arabidopsis plant cell, Arabidopsis plant tissue or Arabidopsis plant comprising an exogenous nucleic acid molecule consisting of the cDNA encoding a flavonol phenylacyltransferase 2 protein having at least 95% sequence identity to SEQ-ID NO:2, wherein said exogenous nucleic acid molecule has been introduced by genetic manipulation into a plant that does not naturally express said nucleic acid molecule, wherein said exogenous nucleic acid molecule is operably linked to a promoter, wherein said transgenic plant cell, plant tissue or plant has enhanced tolerance to UV-B irradiation relative to a native plant cell, plant tissue or plant of the same species that does not naturally express said nucleic acid molecule, and wherein said enhanced UV-B tolerance is assessed after UV-B irradiation treatment for at least 2 hours per day for 28 days with 2000 mW/m2.

### Claim 2 (depends on 1)

The transgenic UV-B tolerant plant cell, plant tissue or plant according to claim 1, wherein said flavonol phenylacyltransferase 2 protein synthesizes a compound of general formula (I)
wherein
R1, R2 and R3 are independently of each other selected from: —H, —OH, and —OCH3;
R4 is selected from —H, —OH, and —OCH3;
R5 represents —H,
and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof.

### Claim 3 (depends on 1)

The transgenic UV-B tolerant plant cell, plant tissue or plant according to claim 1, wherein said flavonol phenylacyltransferases 2 protein synthesizes a compound of general formula (II)
wherein
R4 is selected from —H, —OH, and —OCH3;
R5 represents —H or
and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof.

### Claim 4 (depends on 1)

The transgenic UV-B tolerant plant cell, plant tissue or plant according to claim 1, wherein said flavonol phenylacyltransferases 2 protein synthesizes a compound of general formula (III)
wherein
R4 is selected from —H, —OH, and —OCH3;
R5 represents —H or
and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof.

### Claim 5 (depends on 1)

The transgenic UV-B tolerant plant cell, plant tissue or plant according to claim 1, wherein said flavonol phenylacyltransferases 2 protein synthesizes a compound of general formula (IV)
wherein
R4 is selected from —H, —OH, and —OCH3;
R5 represents —H or
and enantiomers, mixtures of enantiomers, diastereoisomers, mixtures of diastereoisomers, hydrates and solvates thereof.

### Claim 6 (depends on 1)

The transgenic UV-B tolerant plant cell, plant tissue or plant according to claim 1, wherein said flavonol phenylacyltransferases 2 protein synthesizes a compound 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.

### Claim 7 (depends on 1)

The transgenic UV-B tolerant plant cell, plant tissue or plant according to claim 1, wherein said exogenous nucleic acid molecule consists of a cDNA encoding a flavonol phenylacyltransferase 2 protein, wherein said nucleic acid molecule has at least 95% sequence identity to SEQ-ID NO:1.