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Su HJ, Fann YF, Chung MI, Won SJ, Lin CN
New lanostanoids of Ganoderma tsugae
Journal of Natural Products 63 (2000)
514-516
b-D-Xylp-(1-21)-Subst3Ac
Subst = 5α-lanosta-8,24-diene-3α,21-diol = SMILES O{3}[C@@H]1CC[C@]2(C)C3=C([C@@]4(CC[C@H]([C@H]({21}[CH2]O)CC/C=C(C)\C)[C@]4(CC3)C)C)CC[C@H]2C1(C)C |
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Ganoderma tsugae
(NCBI TaxID 34467,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1021/np990367lJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: lincna

cc.kmu.edu.tw
Institutions: School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan 807, Republic of China, Department of Microbiology, Medical College, National Cheng Kung University, Tainan, Taiwan 701, Republic of China
Three new compounds, (24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid C (1); 3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-D-xyloside, named tsugarioside B (2); and 3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1−3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.
Structure type: monomer ; 617 [M+H]+
Location inside paper: structure 2
Trivial name: tsugarioside B
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332
Methods: 13C NMR, 1H NMR, FAB-MS, IR spectroscopy, optical rotation, LiAlH4 reduction, tumor cell growth inhibition sssays
Related record ID(s): 40718, 40719, 49628
NCBI Taxonomy refs (TaxIDs): 34467Reference(s) to other database(s): Chemspider:8779234
Show glycosyltransferases
NMR conditions: in CDCl3
[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
21 bDXylp 102.7 71.9 73.7 69.7 63.7
3 Ac 170.9 21.4
Subst 30.2 23.3 78.1 36.7 45.3 18.0 26.0 134.0 134.6 36.9 21.0 30.8 44.3 49.9 27.5 29.7 40.6 16.1 19.0 44.9 70.2 30.7 24.7
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 |
21 | bDXylp | 102.7 | 71.9 | 73.7 | 69.7 | 63.7 | |
3 | Ac | 170.9 | 21.4 | |
| Subst | 30.2 | 23.3 | 78.1 | 36.7 | 45.3 | 18.0 | 26.0 | 134.0 | 134.6 | 36.9 | 21.0 | 30.8 | 44.3 | 49.9 | 27.5 | 29.7 | 40.6 | 16.1 | 19.0 | 44.9 | 70.2 | 30.7 | 24.7 |
|
There is only one chemically distinct structure:
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Su HJ, Fann YF, Chung MI, Won SJ, Lin CN
New lanostanoids of Ganoderma tsugae
Journal of Natural Products 63 (2000)
514-516
b-D-Xylp-(1-21)-Subst3Ac
Subst = (Z)-24-methyl-5α-lanosta-8,23,25-trien-3α-ol-21-oic acid = SMILES O{3}[C@@H]1CC[C@]2(C)C3=C([C@@]4(CC[C@H]([C@H]({21}[CH2]O)C/C=C(C)/C(C)=C)[C@]4(CC3)C)C)CC[C@H]2C1(C)C |
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Ganoderma tsugae
(NCBI TaxID 34467,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1021/np990367lJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: lincna

cc.kmu.edu.tw
Institutions: School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan 807, Republic of China, Department of Microbiology, Medical College, National Cheng Kung University, Tainan, Taiwan 701, Republic of China
Three new compounds, (24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid C (1); 3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-D-xyloside, named tsugarioside B (2); and 3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1−3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.
Structure type: monomer ; 643.3791 [M+H]+
Location inside paper: structure 3
Trivial name: tsugarioside C
Contained glycoepitopes: IEDB_114701,IEDB_167188,IEDB_174332
Methods: 13C NMR, 1H NMR, FAB-MS, IR spectroscopy, optical rotation, LiAlH4 reduction, tumor cell growth inhibition sssays
Related record ID(s): 40504, 40719, 49629
NCBI Taxonomy refs (TaxIDs): 34467Reference(s) to other database(s): Chemspider:8922064
Show glycosyltransferases
NMR conditions: in CDCl3
[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
21 bDXylp 94.5 72.3 75.9 69.5 65.8
3 Ac 170.9 21.4
Subst 30.4 23.3 78.1 36.7 45.3 18.0 25.9 133.7 134.7 36.9 20.8 30.8 44.3 49.5 27.0 28.9 47.0 16.3 19.0 47.8 175.2 32.9 123.5
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 |
21 | bDXylp | 94.5 | 72.3 | 75.9 | 69.5 | 65.8 | |
3 | Ac | 170.9 | 21.4 | |
| Subst | 30.4 | 23.3 | 78.1 | 36.7 | 45.3 | 18.0 | 25.9 | 133.7 | 134.7 | 36.9 | 20.8 | 30.8 | 44.3 | 49.5 | 27.0 | 28.9 | 47.0 | 16.3 | 19.0 | 47.8 | 175.2 | 32.9 | 123.5 |
|
There is only one chemically distinct structure:
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Su HJ, Fann YF, Chung MI, Won SJ, Lin CN
New lanostanoids of Ganoderma tsugae
Journal of Natural Products 63 (2000)
514-516
b-D-Glcp-(1-21)-Subst3Ac
Subst = fomitoside H, I aglycon = SMILES C/C(C)=C\CC[C@@H]({21}C(=O)O)[C@H]1CC[C@@]2(C)/C4=C(CC[C@]12C)/[C@@]3(C)CC{3}[C@@H](O)C(C)(C)[C@@H]3CC4 |
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Ganoderma tsugae
(NCBI TaxID 34467,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Organ / tissue: fruiting body
The structure was elucidated in this paperPublication DOI: 10.1021/np990367lJournal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Correspondence: lincna

cc.kmu.edu.tw
Institutions: School of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan 807, Republic of China, Department of Microbiology, Medical College, National Cheng Kung University, Tainan, Taiwan 701, Republic of China
Three new compounds, (24R,S)-3α-acetoxy-24-hydroxy-5α-lanosta-8,25-dien-21-oic acid, named tsugaric acid C (1); 3α-acetoxy-5α-lanosta-8,24-diene-21-O-β-D-xyloside, named tsugarioside B (2); and 3α-acetoxy-(Z)-24-methyl-5α-lanosta-8,23,25-trien-21-oic acid ester β-D-xyloside, named tsugarioside C (3), and a mixture of two known steroids were isolated from the fruit bodies of Ganoderma tsugae. The structures of 1−3 were determined by spectral and chemical methods. The cytotoxic activity of the lanostanoid constituents of this fungus was evaluated against several different cancer cell lines.
Structure type: monomer
Location inside paper: structure 7
Trivial name: tsugarioside A
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, FAB-MS, IR spectroscopy, optical rotation, LiAlH4 reduction, tumor cell growth inhibition sssays
Related record ID(s): 40504, 40718
NCBI Taxonomy refs (TaxIDs): 34467Reference(s) to other database(s): Chemspider:8945953
Show glycosyltransferases
There is only one chemically distinct structure:
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