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Structure type: oligomer
Trivial name: trillenoside, trillenoside A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823

• Article ID: 10370
  Nohara T, Nakano A, Miyahara K, Komori T, Kawasaki T "Structure of a novel type steroid glycoside, 18-norspirostanol oligoglycoside" - Tetrahedron Letters 49 (1975) 4381-4384
  

  (no abstract)

  Publication DOI: 10.1016/S0040-4039(00)91130-4
  Journal NLM ID: 2984819R
  Publisher: Elsevier
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan
  
   
  
  Trillium kamtschaticum
  CSDB ID 148882 (all data & tools)
• Article ID: 10380
  Nohara T, Komori T, Kawasaki T "Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pall. III. On the structure of a novel type of steroid glycoside, trillenoside A, an 18-norspirostanol oligoside" - Chemical and Pharmaceutical Bulletin 28 (1980) 1437-1448
  

  A glycoside, mp 209-220° (decomp), [α] D-142°, C_<47>H_<70>O_<24>, named trillenoside A (I), was isolated from the rhizomes of Trillium kamtschaticum PALL (Liliaceae). The structure of its aglycone (designated trillenogenin, II), mp 250-251°, [α] D-198°, C_<26>H_<36>O_8,was determined by X-ray crystallographic analysis of the tetraacetyl monobrosyl derivative, mp 242-244° (dec.), [α] D-112°, C_<40>H_<47>BrO_<14>S, and I was characterized as 15-oxo-18-nor-25 R-spirosta-5,13-diene-1β,3β,21,23α,24β-pentaol 1-O-β-D-apiofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside. I is thus a novel type of steroid glycoside, noteworthy in that the aglycone is an 18-norspirostane derivative having an enone system in the D-ring and hydroxyl groups at C_<21> and in the F-ring, and also in that the sugar moiety is a branched-chain tetrasaccharide containing apiose.

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003662509
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  
   
  
  Trillium kamtschaticum
  CSDB ID 118976 (all data & tools)
• Article ID: 10382
  Fukuda N, Imamura N, Saito E, Nohara T, Kawasaki T "Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pall. IV. Additional oligoglycosides of 18-norspirostane derivatives and other steroidal constituents" - Chemical and Pharmaceutical Bulletin 29(2) (1981) 325-335
  

  Three oligoglycosides of 18-norspirostane derivatives, Ty-2,Ty-3,and Ty-4,along with two steroidal compounds, Tm and Tj, were isolated from the underground parts of Trillium kamtschaticum PALL. These five compounds and two other compounds, Th and Tz acetate, which had been obtained previously but remained unidentified, were characterized as follows. Ty-2,mp 235-240°(dec.), [α]D-110° : deapio-trillenoside A (II) (named trillenoside B). Ty-3,mp 182-185°(dec.), [α]D-98.7° : 3,21-di-O-acetyl-24-epitrillenogenin 1-O-(2', 3', 4'-tri-O-acetyl-α-L-rha・pyr)-(1-2)-α-L-ara・pyranoside (IV) (epitrillenoside C-PA). Ty-4,mp 226-230°(dec.), [α]D-105°; 21-deoxytrillenoside A (VII) (deoxytrillenoside A). Tm, mp 326-329°(dec.), [α]D-99.4° : 24β-hydroxypennogenin (V). Tj, mp 205-212°(dec.), [α]D-66.5° : prototype compound (VIII) of pennogenin 3-O-β-chacotrioside. Th, mp 194-200°(dec.), [α]D-90° : prototype compound (IX) of pennogenin 3-O-α-L-rha・pyr-β-chacotrioside. Tz acetate : crude ecdysterone triacetate (X). This is the first report of the natural occurrence of these compounds, except for IX and X ; the occurrence of IV is particularly interesting. VIII and IX had been expected to coexist with the corresponding pennogenin glycosides.

  Structure determination, oligoglycosides of 18-norspirostane derivatives, trillenoside B, epitrillenoside C-PA, deoxytrillenoside A, 24β-hydroxypennogenin, prototype compounds of pennogenin glycosides, ecdysterone, Trillium kamtschaticum PALL

  Publication DOI: 10.1248/cpb.29.325
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003633659
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  Methods: IR, partial acid hydrolysis, TLC, acid hydrolysis, MS, methanolysis, alkaline hydrolysis, UV, permethylation, CD, PMR, Baeyer-Villiger oxidation
  
   
  
  Trillium kamtschaticum
  CSDB ID 119004 (all data & tools)

Show legend Show as text

Structure type: oligomer
C₄₂H₆₂O₂₀
Trivial name: trillenoside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823

• Article ID: 10380
  Nohara T, Komori T, Kawasaki T "Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pall. III. On the structure of a novel type of steroid glycoside, trillenoside A, an 18-norspirostanol oligoside" - Chemical and Pharmaceutical Bulletin 28 (1980) 1437-1448
  

  A glycoside, mp 209-220° (decomp), [α] D-142°, C_<47>H_<70>O_<24>, named trillenoside A (I), was isolated from the rhizomes of Trillium kamtschaticum PALL (Liliaceae). The structure of its aglycone (designated trillenogenin, II), mp 250-251°, [α] D-198°, C_<26>H_<36>O_8,was determined by X-ray crystallographic analysis of the tetraacetyl monobrosyl derivative, mp 242-244° (dec.), [α] D-112°, C_<40>H_<47>BrO_<14>S, and I was characterized as 15-oxo-18-nor-25 R-spirosta-5,13-diene-1β,3β,21,23α,24β-pentaol 1-O-β-D-apiofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside. I is thus a novel type of steroid glycoside, noteworthy in that the aglycone is an 18-norspirostane derivative having an enone system in the D-ring and hydroxyl groups at C_<21> and in the F-ring, and also in that the sugar moiety is a branched-chain tetrasaccharide containing apiose.

  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003662509
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  
   
  
  Trillium kamtschaticum
  CSDB ID 118977 (all data & tools)
• Article ID: 10382
  Fukuda N, Imamura N, Saito E, Nohara T, Kawasaki T "Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pall. IV. Additional oligoglycosides of 18-norspirostane derivatives and other steroidal constituents" - Chemical and Pharmaceutical Bulletin 29(2) (1981) 325-335
  

  Three oligoglycosides of 18-norspirostane derivatives, Ty-2,Ty-3,and Ty-4,along with two steroidal compounds, Tm and Tj, were isolated from the underground parts of Trillium kamtschaticum PALL. These five compounds and two other compounds, Th and Tz acetate, which had been obtained previously but remained unidentified, were characterized as follows. Ty-2,mp 235-240°(dec.), [α]D-110° : deapio-trillenoside A (II) (named trillenoside B). Ty-3,mp 182-185°(dec.), [α]D-98.7° : 3,21-di-O-acetyl-24-epitrillenogenin 1-O-(2', 3', 4'-tri-O-acetyl-α-L-rha・pyr)-(1-2)-α-L-ara・pyranoside (IV) (epitrillenoside C-PA). Ty-4,mp 226-230°(dec.), [α]D-105°; 21-deoxytrillenoside A (VII) (deoxytrillenoside A). Tm, mp 326-329°(dec.), [α]D-99.4° : 24β-hydroxypennogenin (V). Tj, mp 205-212°(dec.), [α]D-66.5° : prototype compound (VIII) of pennogenin 3-O-β-chacotrioside. Th, mp 194-200°(dec.), [α]D-90° : prototype compound (IX) of pennogenin 3-O-α-L-rha・pyr-β-chacotrioside. Tz acetate : crude ecdysterone triacetate (X). This is the first report of the natural occurrence of these compounds, except for IX and X ; the occurrence of IV is particularly interesting. VIII and IX had been expected to coexist with the corresponding pennogenin glycosides.

  Structure determination, oligoglycosides of 18-norspirostane derivatives, trillenoside B, epitrillenoside C-PA, deoxytrillenoside A, 24β-hydroxypennogenin, prototype compounds of pennogenin glycosides, ecdysterone, Trillium kamtschaticum PALL

  Publication DOI: 10.1248/cpb.29.325
  Journal NLM ID: 0377775
  WWW link: http://ci.nii.ac.jp/naid/110003633659
  Publisher: Pharmaceutical Society Of Japan
  Institutions: Faculty of Pharmaceutical Sciences, Kyushu University, Japan
  Methods: IR, partial acid hydrolysis, TLC, acid hydrolysis, MS, methanolysis, alkaline hydrolysis, UV, permethylation, CD, PMR, Baeyer-Villiger oxidation
  
   
  
  Trillium kamtschaticum
  CSDB ID 119005 (all data & tools)