The structure of a new triterpenoid trisaccharide isolated from the seeds of Acacia auriculiformis has been elucidated as acacic acid lactone-3-O-β-d-glucopyranosyl(1→6)-[α-l-arabinopyranosyl(1→2)]-β-d-glucopyranoside based on its spectral properties and some chemical transformations.
Publication DOI: 10.1016/0031-9422(89)85039-3Journal NLM ID: 0151434Publisher: Elsevier
Institutions: AFRC Institute of Food Research, Norwich, UK, Indian Institute of Chemical Biology, Jadavpur Calcutta, India
Chemistry of some natural products of biological interest is reviewed. Cleomeolide, a diterpene lactone with unprecedented structural features is isolable in quantity from renewable regions of Cleome icosandra widely distributed in India. Its chemical convertibility to a tricarboxylic system analogous to that found in taxane indicated its potential for use as a base material for the synthesis of taxol analogues. Novel triterpene acids isolable by acid hydrolysis of the saponins from Mimusops elengi are potential bioactive compounds. Acaciasides A, B and C, the acylated triterpenoid bisglycosides from the pericarps of Acacia auriculiformis, abundantly available throughout India hold promise for their use as spermicidal and antifilarial agents. Unambiguous structure elucidation of four new saponins from Bacopa monniera reputed for its use as a nervine tonic for memory improvement has been achieved and presence of at least eight other saponins has been confirmed. The results disprove the prevailing notion of occurrence in the plant of only bacoside A1 and bacoside A3. Saikosaponins are biologically interesting compounds reported so far from Bupleurum species. Saikosaponins-like glycosides corchorusins A, B, C, D, C1, D1, D2 and D3 have been isolated from Corchorus acutangulus, a plant of different genus and family occurring throughout the hotter parts of India. Interesting acid-catalysed rearrangemednts of some aglyeones are described. Spermidine and spermine alkaloids which belong to the class of polyamine conjugates possess diverse biochemical profiles. Three spermidine alkaloids, Caesalpinines A, B and C have been isolated from the prickly scandent shrub growing in eastern India. Caesalpinine A possessses a novel skeleton of a 13-membered lactum ring fused to a five-membered lactum ring. Flavonoid-, and phenylpropanoid glycosides from polar fraction of Lantana camara widely occurring in many tropical and subtropical parts of the world are of interst for their use for therapeutic intervention in a wide range of diseases including cancer.
- Compound ID: 31185
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b-D-Glcp-(1-28)-Subst
Subst = arjungenin = SMILES C[C@@]12CC[C@@H]3[C@@](C{2}[C@@H](O){3}[C@H](O)[C@]3({24}CO)C)(C)[C@H]1CC=C4[C@@]2(C)CC[C@]5({28}C(O)=O)[C@H]4{22}[C@H](O)C(C)(C)CC5 |
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Structure type: monomer
Trivial name: arjunglucoside I, arjunglucoside
Compound class: glycoside, triterpenoid glycoside
- Compound ID: 22429
Structure type: oligomer
Trivial name: acteoside, verbascoside, acteoside, verbascoside, trans-verbascoside, verbascoside, acteoside
Compound class: saponin glycoside, glycoside, phenolic glycoside, phenylethanoid glycoside, phenylpropanoid glycoside, iridoid glycoside, lignan glycoside
- Compound ID: 30681
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Subst-(9-4)-+
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a-L-Rhap-(1-3)-b-D-Glcp-(1-8)-3,4,8HOPhet
Subst = 3,4-dihydroxy-cis-cinnamic acid = SMILES O={9}C(O)/C=C\C1=CC={4}C(O){3}C(O)=C1 |
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Structure type: oligomer
Trivial name: cis-verbascoside, lantanaside
Compound class: glycoside, phenylpropanoid glycoside
- Compound ID: 31327
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b-D-Glcp-(1-7)-Subst6Me4'Me
Subst = scutellarein = SMILES O=C(C1=C(C={7}C(O){6}C(O)={5}C1O)O2)C=C2C3=CC={54}C(O)C=C3 |
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Structure type: monomer
Trivial name: linaroside
Compound class: glycoside, flavonoid glycoside
- Compound ID: 32268
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b-D-Glcp-(1-7)-Subst6Me4'Me
Subst = 6-hydroxykaempferol = SMILES O=C(C1=C(C={7}C(O){6}C(O)={5}C1O)O2){3}C(O)=C2C3=CC={54}C(O)C=C3 |
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Structure type: monomer
Trivial name: camaraside
Compound class: glycoside
- Compound ID: 25434
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b-D-Glcp-(1-6)-+
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a-L-Arap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = 16-epi-acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@@](O6)([H])C[C@@](C6=O)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: acaciaside
Compound class: saponin glycoside, glycoside
Reference(s) to other database(s): CCSD:
27983, CBank-STR:6860
- Compound ID: 32253
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a-L-Arap-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = 16-epi-acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@@](O6)([H])C[C@@](C6=O)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: proacaciaside-I
Compound class: glycoside
- Compound ID: 32254
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b-D-Glcp-(1-6)-b-D-Glcp-(1-3)-Subst
Subst = 16-epi-acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@@](O6)([H])C[C@@](C6=O)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: proacaciaside-II
Compound class: glycoside
- Compound ID: 32255
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a-L-Arap-(1-6)-b-D-GlcpNAc-(1-3)-Subst
Subst = 16-epi-acacic acid 21,28-lactone = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@@](O6)([H])C[C@@](C6=O)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: oligomer
Trivial name: acaciamine
Compound class: glycoside
- Compound ID: 32250
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b-D-Glcp-(1-6)-+
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a-L-Arap-(1-2)-b-D-Glcp-(1-3)-+
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a-L-Rhap-(1-6)-+ |
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b-D-Xylp-(1-2)-b-D-Glcp-(1-28)-Subst
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b-D-Glcp-(1-6)-Subst1-(1-21)-+
Subst = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst1 = 6S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C(C)/{1}C(O)=O |
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Structure type: oligomer
Trivial name: acaciaside A
Compound class: glycoside
- Compound ID: 32251
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a-L-Rhap-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Glcp-(1-28)-+
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b-D-Xylp-(1-2)-b-D-Glcp-(1-6)-Subst1-(1-21)-Subst
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b-D-Glcp-(1-6)-+ |
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a-L-Arap-(1-2)-b-D-Glcp-(1-3)-+
Subst = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst1 = 6S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C(C)/{1}C(O)=O |
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Structure type: oligomer
Trivial name: acaciaside B
Compound class: glycoside
- Compound ID: 32252
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a-L-Rhap-(1-6)-+
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b-D-Xylp-(1-2)-b-D-Glcp-(1-28)-+
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a-L-Rhap-(1-2)-b-D-Glcp-(1-6)-Subst1-(1-21)-Subst
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b-D-Glcp-(1-6)-+ |
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a-L-Arap-(1-2)-b-D-Glcp-(1-3)-+
Subst = acacic acid = SMILES C[C@]12CC{3}[C@H](O)C(C)(C)[C@@H]1CC[C@]3(C)[C@@H]2CC=C4[C@@]3(C)C{16}[C@@H](O)[C@]5({28}C(O)=O)[C@H]4CC(C)(C){21}[C@@H](O)C5;
Subst1 = 6S-menthiafolic acid = SMILES C=C{6}[C@@](C)(O)CC/C=C(C)/{1}C(O)=O |
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Structure type: oligomer
Trivial name: acaciaside C
Compound class: glycoside
- Compound ID: 31352
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b-D-Glcp-(1-3)-+
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a-L-Araf-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = jujubogenin = SMILES C/C(C)=C/[C@H]1C[C@](C)(O)[C@@H]2[C@H]3CC[C@@H]4[C@@]5(C)CC{3}[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]36C[C@]2(OC6)O1 |
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Structure type: oligomer
Trivial name: bacoside A3
Compound class: glycoside
- Compound ID: 31354
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b-D-Glcp-(1-3)-+
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a-L-Araf-(1-2)-a-L-Arap-(1-3)-Subst
Subst = pseudojujubogenin = SMILES C{20}[C@]1(O)[C@H](/C=C(C)/C)CO[C@]2(C3)OC[C@]43[C@]5(C)CC[C@H]6C(C)(C){3}[C@@H](O)CC[C@@](C)6[C@H]5CC[C@@H]4[C@@H]12 |
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Structure type: oligomer
Trivial name: bacopasaponin C
Compound class: glycoside
- Compound ID: 32256
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a-L-Araf-(1-2)-a-L-Arap-(1-3)-Subst
Subst = jujubogenin = SMILES C/C(C)=C/[C@H]1C[C@](C)(O)[C@@H]2[C@H]3CC[C@@H]4[C@@]5(C)CC{3}[C@H](O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]36C[C@]2(OC6)O1 |
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Structure type: oligomer
Trivial name: bacoside A1
Compound class: glycoside
- Compound ID: 32257
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a-L-Arap-(1-3)-+
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a-L-Arap-(1-20)-Subst
Subst = jujubogeninAdd20 |
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Structure type: oligomer
Trivial name: bacopasaponin A
Compound class: glycoside
- Compound ID: 32258
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a-L-Araf-(1-2)-a-L-Arap-(1-3)-Subst
Subst = pseudojujubogenin = SMILES C{20}[C@]1(O)[C@H](/C=C(C)/C)CO[C@]2(C3)OC[C@]43[C@]5(C)CC[C@H]6C(C)(C){3}[C@@H](O)CC[C@@](C)6[C@H]5CC[C@@H]4[C@@H]12 |
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Structure type: oligomer
Trivial name: bacopasaponin B
Compound class: glycoside
- Compound ID: 32259
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a-L-Araf-(1-2)-b-D-Glcp-(1-3)-Subst
Subst = pseudojujubogenin = SMILES C{20}[C@]1(O)[C@H](/C=C(C)/C)CO[C@]2(C3)OC[C@]43[C@]5(C)CC[C@H]6C(C)(C){3}[C@@H](O)CC[C@@](C)6[C@H]5CC[C@@H]4[C@@H]12 |
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Structure type: oligomer
Trivial name: bacopasaponin D
Compound class: glycoside
- Compound ID: 32260
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b-D-Galp-(1-3)-Subst
Subst = longispinogenin = SMILES C[C@]1(C2=CC[C@]3([C@@]1(C)CC[C@@]4([C@]3(C)CC{3}[C@@H](C4(C)C)O)[H])[H])C{16}[C@@H]([C@@]5([C@]2(CC(C)(CC5)C)[H]){28}CO)O |
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Structure type: monomer
Trivial name: corchorusin A
Compound class: glycoside
- Compound ID: 32261
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b-D-Galp-(1-3)-Subst
Subst = saikogenin F = SMILES C[C@@]1({23}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])C=C[C@]45[C@]6([H])CC(C)(C)CC[C@@](CO5)6{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: monomer
Trivial name: corchorusin B
Compound class: glycoside
- Compound ID: 32262
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b-D-Galp-(1-3)-Subst
Subst = 23-hydroxylongispinogenin = SMILES C[C@@]1({23}CO){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)CC[C@@]({28}CO)5{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: monomer
Trivial name: corchorusin C
Compound class: glycoside
- Compound ID: 32263
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b-D-Galp-(1-3)-Subst
Subst = saikogenin E = SMILES CC1(C){3}[C@@H](O)CC[C@]2(C)[C@@]3([H])C=C[C@]45[C@]6([H])CC(C)(C)CC[C@@](CO5)6{16}[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H] |
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Structure type: monomer
Trivial name: corchorusin D
Compound class: glycoside
- Compound ID: 32264
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b-D-Galp-(1-3)-Subst
Subst = saikogenin C = SMILES C[C@@]12C{16}[C@@H]([C@]3({28}CO)C(CC(C)(CC3)C)=C1C=C[C@]4([C@@]2(C)CC[C@@]5([C@]4(C)CC{3}[C@@H]([C@@]5(C)C)O)[H])[H])O |
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Structure type: monomer
Trivial name: corchorusin C1
Compound class: glycoside
- Compound ID: 32265
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b-D-Glcp-(1-2)-b-D-Galp-(1-3)-Subst
Subst = saikogenin B = SMILES C[C@]1(C2=CC=C3[C@@]1(C)CC[C@@]4([C@]3(C)CC{3}[C@@H](C4(C)C)O)[H])C{16}[C@@H]([C@]5({28}CO)[C@@]2([H])CC(C)(CC5)C)O |
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Structure type: oligomer
Trivial name: corchorusin D1
Compound class: glycoside
- Compound ID: 32266
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b-D-Glcp-(1-2)-b-D-Galp-(1-3)-Subst
Subst = longispinogenin = SMILES C[C@]1(C2=CC[C@]3([C@@]1(C)CC[C@@]4([C@]3(C)CC{3}[C@@H](C4(C)C)O)[H])[H])C{16}[C@@H]([C@@]5([C@]2(CC(C)(CC5)C)[H]){28}CO)O |
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Structure type: oligomer
Trivial name: corchorusin D2
Compound class: glycoside
- Compound ID: 32267
Structure type: oligomer
Trivial name: corchorusin D3
Compound class: glycoside
Found