A chemical investigation of the trepang (stychopus Japonicus Selenka): The structure of triterpenoid aglycones obtained from trepang glycosides.
✍ Scribed by G.B. Elyakov; T.A. Kuznetsova; A.K. Dzizenko; Yu.N. Elkin
- Publisher
- Elsevier Science
- Year
- 1969
- Tongue
- French
- Weight
- 244 KB
- Volume
- 10
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
We have previously (1) demonstrated that the methanol extract of the Far-Eastern sea cucumber -the trepang -contains 2 glycosides called stichoposides A and C. The present work cites data on the structure of two substances, namely stichopogenins A2 and.A4 , obtained at hydrolyzing stichoposide A with a 12% hydrochloric acid aqueous solution. Stichopogenins A2 snd A4 are the main hydrolysis products, the chromatographically uniform stichopogenin A4 being capable, under these conditions, of partially converting into stichopogenin A2' Stichopogenins A2 and A4 were separated by partition chromatography on a silica gel in the benzene -benzene t ethyl acetate (2rl) gradient elution system. Stichopogenin A2, Ia, C30H4404, m.p. 238-240° (from MeOH>,[d]D 25_ QS* (C 2.5, CHC13), IR spectra: 1755-1760 cm-' (r-la&one). Found: C 76.71 H 9.57; mol.wt. 4.68 (mass spectrometry). Calcd. for C30E4404: C 76.88 H 9.46; mo1.w-t. 468. Stichopogenin A2 monoacetate, Ic, C32H4605, m.p. 2X-219* (from abs. MeOH),[d]$5 -36.3 (C 3.3,,GCHC13), IR spectra in CHC13: 3600 om-' (OH group), 1255 cm-', 1720 om-' (-&L). Found: C 75.11 H 9.38, mol.wt. 510 (mass spectrometry). Celcd. for C32H46 5 0 : C 75.26 H 9.(X, mol.wt. 510. Stichopogenin A4, IIa, C30H4605, m.p. 238-240* (from aqueous Me20>, IR spectra in CHC13s 1755 cm-' (r-lactone). Founds C 72.65 H 9.49, (M+-18) -468 (mass spectrometry). Calcd. for C30R4605W2E20: C 72.72 H 9.49, mol.wt. 486.