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Takaishi Y, Uda M, Ohashi T, Nakano K, Murakami K, Tomimatsu T
Glycosides of ergosterol derivatives from Hericum erinacens
Phytochemistry 30(12) (1991)
4117-4120
|
b-D-Glcp-(1-3)-Subst
Subst = ergosterol = SMILES O{3}[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@@]3(C)CC4 |
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Hericium erinaceus
(NCBI TaxID 91752,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(91)83478-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan, Tokushima Prefectural Tomioka Nishi High School, Tokushima, Japan
A new glycoside of ergosta-7,22-diene-3,5,6-triol was isolated from the dry fruiting body of Hericum erinacens and the structure was established by chemical and spectroscopic means. Six ergosterol derivatives were also isolated from H. erinacens.
glycoside, Hericium erinaceus, Basidiomycete, Hericum erinacens, higher fungi
Structure type: monomer ; 558 [M]+; 581.3799 [M+Na]+
C
34H
5406Location inside paper: p.4418, 2, table 1, table 2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, acid hydrolysis, extraction, optical rotation measurement, EI-MS, column chromatography, HRFAB-MS
Related record ID(s): 44027, 44028
NCBI Taxonomy refs (TaxIDs): 91752
Show glycosyltransferases
NMR conditions: in 5N (C)
[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
3 bDGlcp 102.6 75.3 78.5 71.7 78.6 62.9
Subst 38.0 30.6 76.8 38.0 140.2 120.1 117.0 141.0 46.4 37.5 21.3 39.3 43.0 54.8 23.4 28.7 55.8 12.2 16.4 40.8 21.4 136.1 132.5 43.1 33.4 19.9 20.1 17.9
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
3 bDGlcp 5.05 4.06 4.29 4.29 3.99 4.42-4.58
Subst - 2.19 4.06 2.53-2.90 - 5.64 5.46 - - ? ? ? ? ? ? ? ? 0.66 0.93 - 1.09 5.24 5.30 - - 0.88 0.89 0.99
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
3 bDGlcp 102.6/5.05 75.3/4.06 78.5/4.29 71.7/4.29 78.6/3.99 62.9/4.42-4.58
Subst 30.6/2.19 76.8/4.06 38.0/2.53-2.90 120.1/5.64 117.0/5.46 37.5/? 21.3/? 39.3/? 43.0/? 54.8/? 23.4/? 28.7/? 55.8/? 12.2/0.66 16.4/0.93 21.4/1.09 136.1/5.24 132.5/5.30 19.9/0.88 20.1/0.89 17.9/0.99
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 |
|---|
| 3 | bDGlcp | 5.05 | 4.06 | 4.29 | 4.29 | 3.99 | 4.42
4.58 | |
| | Subst |
| 2.19 | 4.06 | 2.53
2.90 |
| 5.64 | 5.46 |
|
| ? | ? | ? | ? | ? | ? | ? | ? | 0.66 | 0.93 |
| 1.09 | 5.24 | 5.30 |
|
| 0.88 | 0.89 | 0.99 |
|
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 |
|---|
| 3 | bDGlcp | 102.6 | 75.3 | 78.5 | 71.7 | 78.6 | 62.9 | |
| | Subst | 38.0 | 30.6 | 76.8 | 38.0 | 140.2 | 120.1 | 117.0 | 141.0 | 46.4 | 37.5 | 21.3 | 39.3 | 43.0 | 54.8 | 23.4 | 28.7 | 55.8 | 12.2 | 16.4 | 40.8 | 21.4 | 136.1 | 132.5 | 43.1 | 33.4 | 19.9 | 20.1 | 17.9 |
|
There is only one chemically distinct structure:
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Takaishi Y, Uda M, Ohashi T, Nakano K, Murakami K, Tomimatsu T
Glycosides of ergosterol derivatives from Hericum erinacens
Phytochemistry 30(12) (1991)
4117-4120
|
b-D-Glcp-(1-3)-Subst
Subst = (22E)-ergosta-7,22-diene-3β,5α,6β-triol = SMILES [H][C@@]12CC[C@]([C@@]1(C)CC[C@@]3([H])C2=C{6}[C@@H](O){5}[C@@]4(O)C{3}[C@@H](O)CC[C@]34C)([H])[C@H](C)/C=C/[C@H](C)C(C)C |
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Hericium erinaceus
(NCBI TaxID 91752,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(91)83478-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan, Tokushima Prefectural Tomioka Nishi High School, Tokushima, Japan
A new glycoside of ergosta-7,22-diene-3,5,6-triol was isolated from the dry fruiting body of Hericum erinacens and the structure was established by chemical and spectroscopic means. Six ergosterol derivatives were also isolated from H. erinacens.
glycoside, Hericium erinaceus, Basidiomycete, Hericum erinacens, higher fungi
Structure type: monomer ; 615 [M+Na]+
C
34H
56O
8Location inside paper: p.4418, 4, table 1, table 2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, acid hydrolysis, extraction, optical rotation measurement, EI-MS, column chromatography, HRFAB-MS
Related record ID(s): 44026, 44028
NCBI Taxonomy refs (TaxIDs): 91752
Show glycosyltransferases
NMR conditions: in 5N (C)
[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
3 bDGlcp 102.4 75.3 78.6 71.5 78.6 62.7
Subst 33.5 30.1 75.3 38.1 75.9 74.2 120.4 141.4 43.6 38.0 22.3 39.8 43.7 55.2 23.5 28.5 56.1 12.5 18.5 40.9 21.4 136.2 132.1 43.0 33.3 20.2 19.8 17.8
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
3 bDGlcp 4.99 4.08 4.21 4.32 3.75 4.41-4.50
Subst - 2.30 4.93 2.65-2.90 - 4.32 5.76 - 2.54 ? ? ? ? ? ? ? ? 0.67 1.44 - 1.04 5.19 5.27 - - 0.88 0.87 0.97
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
3 bDGlcp 102.4/4.99 75.3/4.08 78.6/4.21 71.5/4.32 78.6/3.75 62.7/4.41-4.50
Subst 30.1/2.30 75.3/4.93 38.1/2.65-2.90 74.2/4.32 120.4/5.76 43.6/2.54 38.0/? 22.3/? 39.8/? 43.7/? 55.2/? 23.5/? 28.5/? 56.1/? 12.5/0.67 18.5/1.44 21.4/1.04 136.2/5.19 132.1/5.27 20.2/0.88 19.8/0.87 17.8/0.97
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 |
|---|
| 3 | bDGlcp | 4.99 | 4.08 | 4.21 | 4.32 | 3.75 | 4.41
4.50 | |
| | Subst |
| 2.30 | 4.93 | 2.65
2.90 |
| 4.32 | 5.76 |
| 2.54 | ? | ? | ? | ? | ? | ? | ? | ? | 0.67 | 1.44 |
| 1.04 | 5.19 | 5.27 |
|
| 0.88 | 0.87 | 0.97 |
|
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 |
|---|
| 3 | bDGlcp | 102.4 | 75.3 | 78.6 | 71.5 | 78.6 | 62.7 | |
| | Subst | 33.5 | 30.1 | 75.3 | 38.1 | 75.9 | 74.2 | 120.4 | 141.4 | 43.6 | 38.0 | 22.3 | 39.8 | 43.7 | 55.2 | 23.5 | 28.5 | 56.1 | 12.5 | 18.5 | 40.9 | 21.4 | 136.2 | 132.1 | 43.0 | 33.3 | 20.2 | 19.8 | 17.8 |
|
There is only one chemically distinct structure:
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Takaishi Y, Uda M, Ohashi T, Nakano K, Murakami K, Tomimatsu T
Glycosides of ergosterol derivatives from Hericum erinacens
Phytochemistry 30(12) (1991)
4117-4120
|
b-D-Glcp-(1-3)-Subst
Subst = (22E,24R)-5α,8α-epidioxyergosta-6,22-diene-3β-ol = SMILES CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@@H]3[C@]1(C)CC[C@@H]4[C@@]2(C)CC{3}[C@H](O)C[C@]25/C=C\[C@]34OO5 |
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Hericium erinaceus
(NCBI TaxID 91752,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1016/0031-9422(91)83478-4Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, University of Tokushima, Tokushima, Japan, Tokushima Prefectural Tomioka Nishi High School, Tokushima, Japan
A new glycoside of ergosta-7,22-diene-3,5,6-triol was isolated from the dry fruiting body of Hericum erinacens and the structure was established by chemical and spectroscopic means. Six ergosterol derivatives were also isolated from H. erinacens.
glycoside, Hericium erinaceus, Basidiomycete, Hericum erinacens, higher fungi
Structure type: monomer ; 613 [M+Na]+
C
34H
5408Location inside paper: p.4418, 7, p.4119, table 2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, acid hydrolysis, extraction, optical rotation measurement, EI-MS, column chromatography, HRFAB-MS
Comments, role: error in the taxon name
Related record ID(s): 44025, 44026, 44027
NCBI Taxonomy refs (TaxIDs): 91752
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
3 bDGlcp 103.0 75.3 78.3 71.5 78.6 62.7
Subst 35.1 29.0 73.8 34.6 82.0 136.1 131.0 79.3 51.8 37.4 21.1 39.5 44.7 52.0 23.6 29.0 56.3 13.0 18.1 40.1 21.1 136.0 132.3 43.0 33.3 20.2 19.9 17.9
1H NMR data:
missing...
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 |
|---|
| 3 | bDGlcp | 103.0 | 75.3 | 78.3 | 71.5 | 78.6 | 62.7 | |
| | Subst | 35.1 | 29.0 | 73.8 | 34.6 | 82.0 | 136.1 | 131.0 | 79.3 | 51.8 | 37.4 | 21.1 | 39.5 | 44.7 | 52.0 | 23.6 | 29.0 | 56.3 | 13.0 | 18.1 | 40.1 | 21.1 | 136.0 | 132.3 | 43.0 | 33.3 | 20.2 | 19.9 | 17.9 |
|
There is only one chemically distinct structure:
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Kim HS, Kim YH, Hong YS, Paek NS, Lee HS, Kim TH, Kim KW, Lee JJ
α-Glucosidase inhibitors from Commelina communis
Planta Medica 65(5) (1999)
437-439
|
b-D-Glcp-(1-7)-Subst
Subst = α-homonojirimycin = SMILES O{7}C[C@H]1N[C@H]({1}CO){2}[C@@H](O){3}[C@H](O){4}[C@H]1O |
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Commelina communis
(NCBI TaxID 4744,
species name lookup)
Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: aerial part
NCBI PubMed ID: 10418330Publication DOI: 10.1055/s-2006-960803Journal NLM ID: 0066751Publisher: George Thieme
Correspondence: Lee JJ <jjlee
kribb4680.kribb.re.kr>
Institutions: Natural Product Biosynthesis Research Unit, Korea Research Institute of Bioscience and Biotechnology, Taejeon, South Korea, Ildong Pharmaceutical Co., Korea, College of Pharmacy, Chungnam National University, Taejeon, South Korea
A methanolic extract of Commelina communis showed potent inhibitory activity against α-glucosidase. One pyrrolidine alkaloid, 2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP, 1) and four piperidine alkaloids, 1-deoxymannojirimycin (2), 1-deoxynojirimycin (3), α-homonojirimycin (4) and 7-O-β-D-glucopyranosyl α-homonojirimycin (5) were isolated by bioassay-directed fractionation and separation. These compounds have been identified for the first time from Commelina communis, supporting the pharmacological basis of this plant that has been used as a traditional herbal medicine for the treatment of diabetes.
diabetes, α-glucosidase inhibitor, Commelina communis, pyrrolidine alkaloid
Structure type: monomer ; 356.1567 [M+H]+
Location inside paper: compound 5, p. 437 (fig., 5)
Trivial name: 7-O-β-D-glucopyranosyl α-homonojirimycin
Compound class: alkaloid
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: HPLC, optical rotation measurement, HRFAB-MS
NCBI Taxonomy refs (TaxIDs): 4744
Show glycosyltransferases
There is only one chemically distinct structure:
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