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Li P, Linhardt RJ, Cao Z
Structural characterization of oligochitosan elicitor from Fusarium sambucinum and its elicitation of defensive responses in Zanthoxylum bungeanum
International Journal of Molecular Sciences 17(12) (2016)
ID E2076
Fusarium sambucinum
(NCBI TaxID 5128,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 27973408Publication DOI: 10.3390/ijms17122076Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: Li P <lipq
nwsuaf.edu.cn>; Li P <lipq110
163.com>
Institutions: Department of Forest Pathology, College of Forestry, Northwest A&F University, Yangling, Shaanxi, China, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New Yourk, USA, Department of Chemistry and Chemical Biology, Chemical and Biological Engineering, and Biology and Biomedical Engineering, Rensselaer Polytechnic Institute, Troy, New York, USA
Oligosaccharide elicitors from pathogens have been shown to play major roles in host plant defense responses involving plant-pathogen chemoperception and interaction. In the present study, chitosan and oligochitosan were prepared from pathogen Fusarium sambucinum, and their effects on infection of Zanthoxylum bungeanum stems were investigated. Results showed that oligochitosan inhibited the infection of the pathogen, and that the oligochitosan fraction with a degree of polymerization (DP) between 5 and 6 showed the optimal effect. Oligochitosan DP5 was purified from fraction DP5-6 and was structurally characterized using electrospray ionization mass spectrometry, Fourier transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy. Oligochitosan DP5 showed significant inhibition against the infection of the pathogenic fungi on host plant stems. An investigation of the mechanism underlying this effect showed that oligochitosan DP5 increased the activities of defensive enzymes and accumulation of phenolics in host Z. bungeanum. These results suggest that oligochitosan from pathogenic fungi can mediate the infection of host plants with a pathogen by acting as an elicitor that triggers the defense system of a plant. This information will be valuable for further exploration of the interactions between the pathogen F. sambucinum and host plant Z. bungeanum.
Structural characterization, plant-pathogen interaction, fungal oligochitosan elicitor, Fusarium sambucinum, Zanthoxylum bungeanum, defensive response
Structure type: oligomer ; 823.33
C
30H
57O
21N
5Location inside paper: DP5, fig. 3, fig. 4, fig. 5
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, ESI-MS, FTIR, statistical analysis, ROESY, DEPT, COSY, HSQC, HCl hydrolysis, sulfuric acid hydrolysis, TLS
Biological activity: The effects of oligochitosan DP5 on F. sambucinum infection of Z. bungeanum stems were evaluated: DP5 treatment at concentrations of 0.01, 0.05 and 0.1 mg/mL decreased the infection of the pathogen relative to that of the control. The incidence of infection in the control was 90.4%, increasing DP5 concentration from 0.01 to 0.1 mg/mL, decreased infection from 64.4% to 25.6%. The application of oligochitosan DP5 in all treatments significantly enhanced defensive activities of PAL, PPO, POD, and CHI enzymes in Z. bungeanum stems, that are involved in plant defenses against pathogen infection in dose-dependent manner (see Fig. 7).
Comments, role: DP5 oligochitosan was obtained by degradation of extracted chitosan (isolated and purified fraction DP5-6) from fungal mycelia by hydrochloric acid; 1H NMR spectrum also showed minor peak at δ 5.34 which was attributed to α form of the reducing end of the pentasaccharide
Related record ID(s): 44856, 44877, 44886, 144096
NCBI Taxonomy refs (TaxIDs): 5128
Show glycosyltransferases
NMR conditions: in D2O at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4 bDGlcpN 98.6 56.7 71.2 78.2 75.1 60.0
bDGlcpN 98.6 56.7 71.2 78.2 75.1 60.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4 bDGlcpN 4.77 3.05 3.80 3.64 3.83 3.67-3.84
bDGlcpN 4.77 3.05 3.80 3.64 3.83 3.67-3.84
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4 bDGlcpN 98.6/4.77 56.7/3.05 71.2/3.80 78.2/3.64 75.1/3.83 60.0/3.67-3.84
bDGlcpN 98.6/4.77 56.7/3.05 71.2/3.80 78.2/3.64 75.1/3.83 60.0/3.67-3.84
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4 | bDGlcpN | 4.77 | 3.05 | 3.80 | 3.64 | 3.83 | 3.67
3.84 |
| | bDGlcpN | 4.77 | 3.05 | 3.80 | 3.64 | 3.83 | 3.67
3.84 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4 | bDGlcpN | 98.6 | 56.7 | 71.2 | 78.2 | 75.1 | 60.0 |
| | bDGlcpN | 98.6 | 56.7 | 71.2 | 78.2 | 75.1 | 60.0 |
|
There is only one chemically distinct structure:
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Chang SY, Yook CS, Nohara T
Two new lupane-triterpene glycosides from leaves of Acanthopanax koreanum
Chemical and Pharmaceutical Bulletin 46(1) (1998)
163-165
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = lup-20(29)-en-3α-ol-23,28-dioic acid = SMILES C[C@@]1({23}C(O)=O){3}[C@H](O)CC[C@]2(C)[C@@]3([H])CC[C@]4([H])[C@@]5([H])[C@H](C(C)=C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Acanthopanax koreanum
(later renamed to: Eleutherococcus koreanus)
(NCBI TaxID 96667,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.46.163Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kumanoto University, Kumamoto, Japan, College of Pharmacy, Kyung-Hee University, Seul, Korea
Two new lupane-triterpene glycosides, acankoreoside A (1) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae). Based on spectroscopic data, the chemical structures of 1 and 2 were determined as 3 alpha-hydroxy-lup-20(29)-en-23,28-dioic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester and 3 alpha,11 alpha,23-trihydroxy-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively.
leaf, araliaceae, Acanthopanax koreanum, lupane-triterpene glycoside, acankoreoside A and B
Structure type: oligomer ; 979.4878 [M+Na]+
C
48H
76O
19Location inside paper: p. 165, Scheme, compound 1, table 1, table 2
Trivial name: acankoreoside A
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GLC, extraction, optical rotation measurement, EI-MS, melting point determination, HMBC, HR-FAB-MS, TLS, aid hydrolysis
Related record ID(s): 120834
NCBI Taxonomy refs (TaxIDs): 96667Reference(s) to other database(s): CCSD:
8972, CBank-STR:21885
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
28,6,4 aLRhap 102.7 72.5 72.7 73.9 70.3 18.5
28,6 bDGlcp 105.1 75.3 76.4 78.2 77.1 61.3
28 bDGlcp 95.2 74.0 78.7 70.8 77.9 69.4
Subst 32.9 46.2 73.0 52.0 44.9 21.8 34.5 41.8 51.0 37.4 20.9 26.0 38.3 42.9 30.1 31.9 57.0 49.7 47.4 150.8 30.8 36.9 179.0 18.0 16.8 16.7 14.8 174.9 110.0 19.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
28,6,4 aLRhap 5.84 4.66 4.54 4.34 4.96 1.69
28,6 bDGlcp 4.95 3.93 4.13 4.39 3.65 4.07-4.19
28 bDGlcp 6.34 4.08 4.21 4.30 4.09 4.28-4.67
Subst ? ? 4.28 - ? ? ? - 1.66 - 1.23-1.47 ? 2.67 - ? ? - ? 3.38 - ? ? - 1.46 0.95 1.20 0.87 - 4.72-4.85 1.70
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
28,6,4 aLRhap 102.7/5.84 72.5/4.66 72.7/4.54 73.9/4.34 70.3/4.96 18.5/1.69
28,6 bDGlcp 105.1/4.95 75.3/3.93 76.4/4.13 78.2/4.39 77.1/3.65 61.3/4.07-4.19
28 bDGlcp 95.2/6.34 74.0/4.08 78.7/4.21 70.8/4.30 77.9/4.09 69.4/4.28-4.67
Subst 32.9/? 46.2/? 73.0/4.28 44.9/? 21.8/? 34.5/? 51.0/1.66 20.9/1.23-1.47 26.0/? 38.3/2.67 30.1/? 31.9/? 49.7/? 47.4/3.38 30.8/? 36.9/? 18.0/1.46 16.8/0.95 16.7/1.20 14.8/0.87 110.0/4.72-4.85 19.4/1.70
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 28,6,4 | aLRhap | 5.84 | 4.66 | 4.54 | 4.34 | 4.96 | 1.69 | |
| 28,6 | bDGlcp | 4.95 | 3.93 | 4.13 | 4.39 | 3.65 | 4.07
4.19 | |
| 28 | bDGlcp | 6.34 | 4.08 | 4.21 | 4.30 | 4.09 | 4.28
4.67 | |
| | Subst | ? | ? | 4.28 |
| ? | ? | ? |
| 1.66 |
| 1.23
1.47 | ? | 2.67 |
| ? | ? |
| ? | 3.38 |
| ? | ? |
| 1.46 | 0.95 | 1.20 | 0.87 |
| 4.72
4.85 | 1.70 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 28,6,4 | aLRhap | 102.7 | 72.5 | 72.7 | 73.9 | 70.3 | 18.5 | |
| 28,6 | bDGlcp | 105.1 | 75.3 | 76.4 | 78.2 | 77.1 | 61.3 | |
| 28 | bDGlcp | 95.2 | 74.0 | 78.7 | 70.8 | 77.9 | 69.4 | |
| | Subst | 32.9 | 46.2 | 73.0 | 52.0 | 44.9 | 21.8 | 34.5 | 41.8 | 51.0 | 37.4 | 20.9 | 26.0 | 38.3 | 42.9 | 30.1 | 31.9 | 57.0 | 49.7 | 47.4 | 150.8 | 30.8 | 36.9 | 179.0 | 18.0 | 16.8 | 16.7 | 14.8 | 174.9 | 110.0 | 19.4 |
|
There is only one chemically distinct structure:
Expand this record
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Chang SY, Yook CS, Nohara T
Two new lupane-triterpene glycosides from leaves of Acanthopanax koreanum
Chemical and Pharmaceutical Bulletin 46(1) (1998)
163-165
|
a-L-Rhap-(1-4)-b-D-Glcp-(1-6)-b-D-Glcp-(1-28)-Subst
Subst = lup-20(29)-en-3α,11α,23-triol-28-oic acid = SMILES C[C@@]1({23}CO){3}[C@H](O)CC[C@]2(C)[C@@]3([H]){11}[C@H](O)C[C@]4([H])[C@@]5([H])[C@H](C(C)=C)CC[C@@]({28}C(O)=O)5CC[C@](C)4[C@@](C)3CC[C@@]12[H] |
Show graphically |
Acanthopanax koreanum
(later renamed to: Eleutherococcus koreanus)
(NCBI TaxID 96667,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaf
The structure was elucidated in this paperPublication DOI: 10.1248/cpb.46.163Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Kumanoto University, Kumamoto, Japan, College of Pharmacy, Kyung-Hee University, Seul, Korea
Two new lupane-triterpene glycosides, acankoreoside A (1) and B (2), were isolated from the leaves of Acanthopanax koreanum NAKAI (Araliaceae). Based on spectroscopic data, the chemical structures of 1 and 2 were determined as 3 alpha-hydroxy-lup-20(29)-en-23,28-dioic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester and 3 alpha,11 alpha,23-trihydroxy-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively.
leaf, araliaceae, Acanthopanax koreanum, lupane-triterpene glycoside, acankoreoside A and B
Structure type: oligomer ; 957 [M-H]-
C
48H
78O
19Location inside paper: p. 165, Scheme, compound 2, table 1, table 2
Trivial name: acankoreoside B
Compound class: triterpene glycoside
Contained glycoepitopes: IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, GLC, extraction, optical rotation measurement, EI-MS, melting point determination, HMBC, HR-FAB-MS, TLS, aid hydrolysis
Related record ID(s): 120833
NCBI Taxonomy refs (TaxIDs): 96667Reference(s) to other database(s): CCSD:
8999, CBank-STR:21886
Show glycosyltransferases
NMR conditions: in C5D5N
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30
28,6,4 aLRhap 102.7 72.5 72.7 73.9 70.3 18.5
28,6 bDGlcp 105.0 75.2 76.4 78.2 77.1 61.3
28 bDGlcp 95.3 74.0 78.6 70.8 78.0 69.4
Subst 35.9 27.1 75.7 41.1 43.8 18.3 35.4 42.7 55.6 39.6 69.8 38.3 37.4 42.9 30.0 32.2 56.9 49.4 47.1 150.4 30.9 36.7 71.9 18.3 17.1 17.7 14.8 175.0 110.0 19.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30
28,6,4 aLRhap 5.83 4.66 4.53 4.32 4.93 1.70
28,6 bDGlcp 4.94 3.94 4.15 4.39 3.67 4.11-4.19
28 bDGlcp 6.32 4.08 4.21 4.30 4.11 4.28-4.67
Subst ? ? 3.92 - ? ? ? - 1.92 - 4.33 ? 2.98 - ? ? - ? 3.38 - ? ? 3.67-3.88 0.83 1.29 1.25 1.00 - 4.61-4.80 1.64
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24 C25/H25 C26/H26 C27/H27 C28/H28 C29/H29 C30/H30
28,6,4 aLRhap 102.7/5.83 72.5/4.66 72.7/4.53 73.9/4.32 70.3/4.93 18.5/1.70
28,6 bDGlcp 105.0/4.94 75.2/3.94 76.4/4.15 78.2/4.39 77.1/3.67 61.3/4.11-4.19
28 bDGlcp 95.3/6.32 74.0/4.08 78.6/4.21 70.8/4.30 78.0/4.11 69.4/4.28-4.67
Subst 35.9/? 27.1/? 75.7/3.92 43.8/? 18.3/? 35.4/? 55.6/1.92 69.8/4.33 38.3/? 37.4/2.98 30.0/? 32.2/? 49.4/? 47.1/3.38 30.9/? 36.7/? 71.9/3.67-3.88 18.3/0.83 17.1/1.29 17.7/1.25 14.8/1.00 110.0/4.61-4.80 19.5/1.64
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 | H25 | H26 | H27 | H28 | H29 | H30 |
|---|
| 28,6,4 | aLRhap | 5.83 | 4.66 | 4.53 | 4.32 | 4.93 | 1.70 | |
| 28,6 | bDGlcp | 4.94 | 3.94 | 4.15 | 4.39 | 3.67 | 4.11
4.19 | |
| 28 | bDGlcp | 6.32 | 4.08 | 4.21 | 4.30 | 4.11 | 4.28
4.67 | |
| | Subst | ? | ? | 3.92 |
| ? | ? | ? |
| 1.92 |
| 4.33 | ? | 2.98 |
| ? | ? |
| ? | 3.38 |
| ? | ? | 3.67
3.88 | 0.83 | 1.29 | 1.25 | 1.00 |
| 4.61
4.80 | 1.64 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 | C25 | C26 | C27 | C28 | C29 | C30 |
|---|
| 28,6,4 | aLRhap | 102.7 | 72.5 | 72.7 | 73.9 | 70.3 | 18.5 | |
| 28,6 | bDGlcp | 105.0 | 75.2 | 76.4 | 78.2 | 77.1 | 61.3 | |
| 28 | bDGlcp | 95.3 | 74.0 | 78.6 | 70.8 | 78.0 | 69.4 | |
| | Subst | 35.9 | 27.1 | 75.7 | 41.1 | 43.8 | 18.3 | 35.4 | 42.7 | 55.6 | 39.6 | 69.8 | 38.3 | 37.4 | 42.9 | 30.0 | 32.2 | 56.9 | 49.4 | 47.1 | 150.4 | 30.9 | 36.7 | 71.9 | 18.3 | 17.1 | 17.7 | 14.8 | 175.0 | 110.0 | 19.5 |
|
There is only one chemically distinct structure:
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