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Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: seed

The structure was elucidated in this paper
NCBI PubMed ID: 10748717
Publication DOI: 10.1248/cpb.47.1744
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan

Following the elucidation of jujubosides A1 and C and acetyljujuboside B, novel protojujubogenin type triterpene bisdesmosides, protojujubosldes A, B, and B1, were isolated from Zizyphi Spinosi Semen, the seeds of Zizyphus jujuba MILL. var. spinosa Hu. The structures of protojujubosides A, B, and B1 were determined on the basis of chemical and physicochemical evidence, which included the conversion of protojujubosides to known jujubosides using enzymatic hydrolysis. Protojujubosides A and jujubosides A, B, and C were found to show potent immunological adjuvant activity.

Zizyphus jujuba var. spinosa, protojujubosides, Zizyphi Spinosi Semen, protojujubogenin type triterpene bisdesmoside, immunological adjuvant activity

Structure type: oligomer ; 1385 [M-H]-
C₆₄H₁₀₆O₃₂
Location inside paper: compound 1, chart 1(1), table 1(1)
Trivial name: protojujuboside A
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_241101,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, ELISA, enzymatic hydrolysis, GLC, HPLC, optical rotation measurement, ROESY, immunological assays, HMBC, HR-FAB-MS, trimethylsilylation, mathanolysis
Biological activity: Compound 1 at PHA titer of 194 had effect on serum anti-OVA antibody levels in OVA-immunized mice with ELISA value (492 nm) of 1.240±0.455.
Comments, role: NMR temperature was not specified

Related record ID(s): 60167, 60168, 60169, 60170, 60171, 60172, 63814, 63815
NCBI Taxonomy refs (TaxIDs): 714518
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	C29	C30
3,2	aLRhap	101.6	72.4	72.5	73.9	70.1	18.6
3,3,2	bDXylp	106.4	76.3	75.0	70.8	67.9
3,3,6	bDGlcp	105.2	75.4	78.2	71.4	75.4	62.5
3,3	bDGlcp	104.0	53.1	75.0	71.4	76.6	70.3
3	aLArap	104.0	75.1	82.8	67.9	63.4
23	bDGlcp	104.6	75.5	75.9	71.6	78.4	62.5
	Subst	39.2	26.6	88.4	39.7	56.4	18.6	36.4	40.7	51.8	37.3	21.9	27.6	41.8	49.4	45.2	219.3	59.8	16.9	16.7	74.5	27.3	45.2	76.6	125.8	132.6	25.8	18.3	28.0	17.1	62.7

¹H NMR data: present in publication

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	C29	C30
3,2	aLRhap	101.6	72.4	72.5	73.9	70.1	18.6
3,3,2	bDXylp	106.4	76.3	75.0	70.8	67.9
3,3,6	bDGlcp	105.2	75.4	78.2	71.4	75.4	62.5
3,3	bDGlcp	104.0	53.1	75.0	71.4	76.6	70.3
3	aLArap	104.0	75.1	82.8	67.9	63.4
23	bDGlcp	104.6	75.5	75.9	71.6	78.4	62.5
	Subst	39.2	26.6	88.4	39.7	56.4	18.6	36.4	40.7	51.8	37.3	21.9	27.6	41.8	49.4	45.2	219.3	59.8	16.9	16.7	74.5	27.3	45.2	76.6	125.8	132.6	25.8	18.3	28.0	17.1	62.7

There is only one chemically distinct structure:

CC(C)=C[C@H](C[C@](C)(O)[C@H]1C(=O)C[C@]2(CO)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4OC[C@H](O)[C@H](O[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O)[C@H]5O[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)C(C)(C)C3CC[C@]12C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Zizyphus jujuba var. spinosa, protojujubosides, Zizyphi Spinosi Semen, protojujubogenin type triterpene bisdesmoside, immunological adjuvant activity

Structure type: oligomer ; 1223 [M-H]-
C₅₈H₉₆O₂₇
Location inside paper: compound 2, chart 1(2), table 1(2)
Trivial name: protojujuboside B
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, ELISA, enzymatic hydrolysis, GLC, HPLC, optical rotation measurement, ROESY, immunological assays, HMBC, HR-FAB-MS, trimethylsilylation, mathanolysis
Biological activity: Compound 2 at PHA titer of 97 had effect on serum anti-OVA antibody levels in OVA-immunized mice with ELISA value (492 nm) of 1.289±0.379.
Comments, role: NMR temperature was not specified

Related record ID(s): 60167, 60168, 60169, 60170, 60171, 60172, 63813, 63815
NCBI Taxonomy refs (TaxIDs): 714518
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	C29	C30
3,2	aLRhap	101.6	72.3	72.5	74.0	70.1	18.5
3,3,2	bDXylp	106.3	76.1	75.1	70.8	67.8
3,3	bDGlcp	103.7	83.4	78.2	71.2	78.5	62.5
3	aLArap	104.1	74.9	81.9	67.8	63.6
23	bDGlcp	104.5	75.5	78.9	71.7	78.3	62.4
	Subst	39.2	26.6	88.4	39.7	56.4	18.6	36.4	40.7	51.8	37.4	21.9	27.6	41.9	49.4	45.2	219.4	59.8	16.9	16.7	74.5	27.3	45.4	76.5	125.8	132.6	25.8	18.3	25.1	17.1	62.8

¹H NMR data: present in publication

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	C29	C30
3,2	aLRhap	101.6	72.3	72.5	74.0	70.1	18.5
3,3,2	bDXylp	106.3	76.1	75.1	70.8	67.8
3,3	bDGlcp	103.7	83.4	78.2	71.2	78.5	62.5
3	aLArap	104.1	74.9	81.9	67.8	63.6
23	bDGlcp	104.5	75.5	78.9	71.7	78.3	62.4
	Subst	39.2	26.6	88.4	39.7	56.4	18.6	36.4	40.7	51.8	37.4	21.9	27.6	41.9	49.4	45.2	219.4	59.8	16.9	16.7	74.5	27.3	45.4	76.5	125.8	132.6	25.8	18.3	25.1	17.1	62.8

There is only one chemically distinct structure:

CC(C)=C[C@H](C[C@](C)(O)[C@H]1C(=O)C[C@]2(CO)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4OC[C@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]5OC[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)C(C)(C)C3CC[C@]12C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Zizyphus jujuba var. spinosa, protojujubosides, Zizyphi Spinosi Semen, protojujubogenin type triterpene bisdesmoside, immunological adjuvant activity

Structure type: oligomer ; 1223 [M-H]-
C₅₈H₉₆O₂₇
Location inside paper: compound 3, chart 1(3), table 1(3)
Trivial name: protojujuboside B1
Compound class: saponin glycoside
Contained glycoepitopes: IEDB_114701,IEDB_136045,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_152214,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_983931,SB_192,SB_86

Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, ELISA, enzymatic hydrolysis, GLC, HPLC, optical rotation measurement, ROESY, immunological assays, HMBC, HR-FAB-MS, trimethylsilylation, mathanolysis
Biological activity: Compound 3 at PHA titer of 64 had effect on serum anti-OVA antibody levels in OVA-immunized mice with ELISA value (492 nm) of 0.572±0.153.
Comments, role: NMR temperature was not specified

Related record ID(s): 60167, 60168, 60169, 60170, 60171, 60172, 63813, 63814
NCBI Taxonomy refs (TaxIDs): 714518
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	C29	C30
3,2	aLFucp	101.5	67.8	72.1	74.2	67.0	17.3
3,3,2	bDXylp	105.9	75.8	75.1	70.8	67.7
3,3	bDGlcp	103.4	82.5	75.5	71.6	78.4	62.4
3	aLArap	104.6	74.5	52.6	67.8	64.7
23	bDGlcp	104.6	75.5	78.9	71.2	78.5	62.5
	Subst	39.2	26.7	88.0	39.6	56.4	18.6	36.4	40.7	51.8	37.3	21.9	27.6	41.9	49.4	45.2	219.3	59.7	17.1	16.7	74.5	27.3	45.3	76.5	125.8	132.6	25.8	15.3	28.0	16.7	62.8

¹H NMR data: present in publication

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	C29	C30
3,2	aLFucp	101.5	67.8	72.1	74.2	67.0	17.3
3,3,2	bDXylp	105.9	75.8	75.1	70.8	67.7
3,3	bDGlcp	103.4	82.5	75.5	71.6	78.4	62.4
3	aLArap	104.6	74.5	52.6	67.8	64.7
23	bDGlcp	104.6	75.5	78.9	71.2	78.5	62.5
	Subst	39.2	26.7	88.0	39.6	56.4	18.6	36.4	40.7	51.8	37.3	21.9	27.6	41.9	49.4	45.2	219.3	59.7	17.1	16.7	74.5	27.3	45.3	76.5	125.8	132.6	25.8	15.3	28.0	16.7	62.8

There is only one chemically distinct structure:

SVG MW SMILES 3D mol Ionize