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1. (Article ID: 11260)
Luo J, Nishiyama Y, Fuell C, Taguchi G, Elliott K, Hill L, Tanaka Y, Kitayama M, Yamazaki M, Bailey P, Parr A, Michael AJ, Saito K, Martin C
Convergent evolution in the BAHD family of acyl transferases: identification and characterization of anthocyanin acyl transferases from Arabidopsis thaliana
Plant Journal: for Cell and Molecular Biology 50 (2007)
678-695
Members of the BAHD family of plant acyl transferases are very versatile catalytically, and are thought to be able to evolve new substrate specificities rapidly. Acylation of anthocyanins occurs in many plant species and affects anthocyanin stability and light absorption in solution. The versatility of BAHD acyl transferases makes it difficult to identify genes encoding enzymes with defined substrate specificities on the basis of structural homology to genes of known catalytic function alone. Consequently, we have used a modification to standard functional genomics strategies, incorporating co-expression profiling with anthocyanin accumulation, to identify genes encoding three anthocyanin acyl transferases from Arabidopsis thaliana. We show that the activities of these enzymes influence the stability of anthocyanins at neutral pH, and some acylations also affect the anthocyanin absorption maxima. These properties make the BAHD acyl transferases suitable tools for engineering anthocyanins for an improved range of biotechnological applications.
anthocyanins, acyl transferases, convergent evolution, functional genomics
Publication DOI: 10.1111/j.1365-313X.2007.03079.xJournal NLM ID: 9207397Publisher: Oxford: Blackwell Scientific Publishers and BIOS Scientific Publishers for the Society for Experimental Biology
Correspondence: cathie.martin

bbsrc.ac.uk
Institutions: John Innes Centre, Norwich Research Park, Colney, Norwich, NR4 7UH, UK, Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan, Institute of Life Science, Ehime Women’s College, 421 Ibuki-cho Baba, Uwajima-shi, Ehime, 798-0025, Japan, Technologies for Systems Biology, Institute of Food Research, Norwich Research Park, Colney, Norwich, NR4 7UA, UK, Department of Applied Biology, Faculty of Textile Science and Technology, Shinshu University, 3-15-1 Tokida, Ueda, Nagano 386-8567, Japan, Institute of Advanced Technology, Suntory Ltd., 1-1-1 Wakayamadai, Shimamoto-cho, Mishima-gun, Osaka, 618-8503, Japan, RIKEN Plant Science Center, Suehiro-cho 1-7-22, Tsurumi-ku, Yokohama, 230-0045, Japan
Methods: ESI-MS, biological assays, HPLC, UV, LC-MS, enzymatic assay, genetic manipulations
The publication contains the following compound(s):
- Compound ID: 26750
Structure type: oligomer
Trivial name: A1
Compound class: glycoside, flavonoid glycoside
Reference(s) to other database(s): CCSD:
41319, CBank-STR:7431
- Compound ID: 28250
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Mal-(1-6)-b-D-Glcp-(1-5)-+
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Sin-(9-2)-b-D-Xylp-(1-2)-+ |
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b-D-Glcp-(1-4)-pCoum-(9-6)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A11
- Compound ID: 28251
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Mal-(1-6)-b-D-Glcp-(1-5)-+
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b-D-Xylp-(1-2)-+ |
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b-D-Glcp-(1-4)-pCoum-(9-6)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A8
- Compound ID: 28252
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b-D-Glcp-(1-5)-+
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pCoum-(9-6)-+ |
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Sin-(9-2)-b-D-Xylp-(1-2)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A7
- Compound ID: 28253
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Mal-(1-6)-b-D-Glcp-(1-5)-+
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pCoum-(9-6)-+ |
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b-D-Xylp-(1-2)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A5
- Compound ID: 28254
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b-D-Glcp-(1-5)-+
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Sin-(9-2)-b-D-Xylp-(1-2)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A4
- Compound ID: 28255
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Mal-(1-6)-b-D-Glcp-(1-5)-+
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pCoum-(9-6)-+ |
| |
Sin-(9-2)-b-D-Xylp-(1-2)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A9
- Compound ID: 28256
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b-D-Glcp-(1-5)-+
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pCoum-(9-6)-+ |
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b-D-Xylp-(1-2)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A3
- Compound ID: 28309
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Mal-(1-6)-b-D-Glcp-(1-5)-+
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b-D-Xylp-(1-2)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A2
- Compound ID: 28310
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b-D-Glcp-(1-5)-+
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b-D-Xylp-(1-2)-+ |
| |
b-D-Glcp-(1-4)-pCoum-(9-6)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A6
- Compound ID: 28311
|
b-D-Glcp-(1-5)-+
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Sin-(9-2)-b-D-Xylp-(1-2)-+ |
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b-D-Glcp-(1-4)-pCoum-(9-6)-b-D-Glcp-(1-3)-Cyanidin |
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Structure type: oligomer
Trivial name: A10
- Compound ID: 26776
Structure type: oligomer
Trivial name: A13
Compound class: glycoside, flavonoid glycoside, anthocyanin glucoside
Reference(s) to other database(s): CCSD:
41382, CBank-STR:3385
- Compound ID: 28414
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a-L-Rhap-(1-6)-b-D-Glcp-(1-3)-Subst
Subst = pelargonidin = SMILES O{3}C1=C(C2=CC={54}C(O)C=C2)[O+]=C3C={7}C(O)C={5}C(O)C3=C1 |
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Structure type: oligomer
Trivial name: A12
Compound class: glycoside, flavonoid glycoside
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2. (Article ID: 11621)
Zou K, Wang B, Li DY, Cai SQ, Zhang RY, Zhao YY
Structural identification of two diastereoisomeric saponins from Albizia julibrissin
Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao = Chemical Journal of Chinese Universities [Chinese] 20(12) (1999)
1877-1882
Two new diastereoisomeric saponins named as Julibroside J14 and Julibroside J15 were isolated from the dried stem barks of Albizia julibrissin. On the basis of chemical and spectral methods, their structures were elucidated as 3-O-[β-D-xylopyranosyl-(1→2)-β-D-arabinonosyl-(1→6)-β-D-glucopyranosyl]-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[4-O-((6R)-2-trans-2,6-dimethyl-6-O-β-D-quinovopyranosyl-2,7-octadienoyl)-β-D-quinovopyranosyl]-2,7-octadienoyl} acacic acid 28-O-β-D-glucopyranosyl-(1→3)-[α-L-arabinofuranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester (1) and 3-O-[β-D-xylopyranosyl-(1→2)-β-D-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]-21-O-{(6S)-2-trans-2,6-dimethyl-6-O-[4-O-((6S)-2-trans-2,6-dimethyl-6-O-β-D-quinovopyranosyl-2,7-octadienoyl)-β-D-quinovopyranosyl]-2,7-octadienoyl} acacic acid 28-O-β-D-glucopyranosyl-(1→3)-[α-L-arabinofuranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl ester (2), respectively.
triterpenoid saponins, Albizia julibrissin, Leguminousae, diastereoisomerism, julibroside J14, julibroside J15
The publication contains the following compound(s):
- Compound ID: 29892
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a-L-Araf-(1-4)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-+
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b-D-Quip-(1-6)-Subst3-(1-4)-b-D-Quip-(1-6)-Subst2-(1-21)-Subst1
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b-D-Xylp-(1-2)-b-D-Arap-(1-6)-b-D-Glcp-(1-3)-+
Subst1 = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst2 = 6S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C(C)/{1}C(O)=O;
Subst3 = 6R-menthiafolic acid = SMILES C=C{6}[C@](C)(O)CC/C=C(C)/{1}C(O)=O |
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Structure type: oligomer
; 2164 [M+Na]+
C101H160O48
Trivial name: julibroside J14
Compound class: saponin glycoside
- Compound ID: 29893
|
a-L-Araf-(1-4)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-+
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b-D-Quip-(1-6)-Subst2-(1-4)-b-D-Quip-(1-6)-Subst2-(1-21)-Subst1
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b-D-Xylp-(1-2)-b-D-Arap-(1-6)-b-D-Glcp-(1-3)-+
Subst1 = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst2 = 6S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C(C)/{1}C(O)=O |
Show graphically |
Structure type: oligomer
; 2142 [M+H]+
C101H160O48
Trivial name: julibroside J15
Compound class: saponin glycoside
- Compound ID: 29894
|
a-L-Araf-(1-4)-+
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b-D-Glcp-(1-3)-a-L-Rhap-(1-2)-b-D-Glcp-(1-28)-+
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b-D-Quip-(1-6)-Subst3-(1-4)-b-D-Quip-(1-6)-Subst2-(1-21)-Subst1
|
b-D-Xylp-(1-2)-b-D-Arap-(1-6)-b-D-Glcp-(1-3)-+
Subst1 = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst3 = 6S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C(C)/{1}C(O)=O;
Subst2 = 6S-hydroxy-2-hydroxymethyl-6-methyl-2E,7-octadienoic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C({9}CO)/{1}C(O)=O |
Show graphically |
Structure type: oligomer
Trivial name: julibroside J1
Compound class: saponin glycoside
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3. (Article ID: 11622)
Chen MJ
Steroidal saponins from Speirantha gardenii (Liliaceae)
Acta Botanica Sinica 41(11) (1999)
1249-1251
Two new steroidal saponins were isolated from the rhizome of the Chinese native plant, Speirantha gardenii (Hook.) Baill. Their structures were established as 22-methoxy-(25R)-5β-furostane-1β,3β,4β,5β,26-pentaol 26-O-β-D-glucopyranoside (I) and 22-methoxy-(25R)-5β-furostane-1β,2β,3β,4β,5β,26-hexaol 26-O-β-D-glucopyranoside (II) on the basis of chemical and spectral evidences.
steroidal saponin, Speirantha gardenii
The publication contains the following compound(s):
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4. (Article ID: 11623)
Ma JY, He AM, Zhang DC, Wang ZT, Xu LS, Xu GJ, Namba T, Kadota S
Two new sesquiterpene glucosides from Ixseris plants
Studies in Plant Science 6 (1999)
394-398
The whole plant of Ixeris denticulata f. pinnatipartita and I. sonchifolia respectively afforded a new guaianolide sesquiterpene lactone glucoside named ixerin X, 8β,15-dihydroxy-1(10),3,11(13)-guaiatriene-12, (1), ixerin Z, 1(10),3,11(13)-guaiatriene-12,6-olide-2-one-3-O-beta-D-glucopyranoside (2), whose structure and stereo-chemistry were determined by spectroscopic methods. 1 inhibited the growth of human breast cancer MCF7 and MDA468 cell lines.
cytotoxicity, compositae, guaianolide, ixerin Z, Ixeris denticulata f. pinnatipartita Kitag., I. sonchifolia Hance, sesquiterpene lactone glucoside, ixerin X
Publication DOI: 10.1016/S0928-3420(99)80052-4Journal NLM ID: 101589254Publisher: Toronto, ON: Canadian Center of Science and Education
Institutions: Shanghai Representative Office, Generation Health Co., Shanghai Medical University, 200032, Shanghai, China, Department of Pharmacognosy, China Pharmaceutical University, No 1 Shennong Rd. Nangjing, 210038, China, Toyama Medical & Pharmaceutical University, 230-01, Toyama, Japan
Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, TLC, optical rotation measurement, cytotoxicity assay, HMBC, HMQC, COSY, NOESY, FT-IR
The publication contains the following compound(s):
- Compound ID: 29897
|
b-D-Glcp-(1-15)-Subst
Subst = 8β,15-dihydroxy-1(10),3,11(13)-guaiatriene-12,6-olide = SMILES CC1=C(CC=C2{15}CO)[C@H]2[C@@H](OC(C3=C)=O)[C@H]{8}3[C@H](O)C1 |
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Structure type: monomer
; 424
C21H25O9
Trivial name: ixerin X
Compound class: sesquiterpenoid glycoside
- Compound ID: 29898
|
b-D-Glcp-(1-3)-Subst
Subst = l(10),3,11(13)-guaiatriene-12,6-olide-2-one = SMILES CC1={3}C(O)C(C2=C(C)CC[C@@H]3[C@H](OC(C3=C)=O)[C@H]21)=O |
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Structure type: monomer
; 445 [M+Na]+
C21H25O9
Trivial name: ixerin Z
Compound class: sesquiterpenoid glycoside
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