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

The structure was elucidated in this paper
Publication DOI: 10.1016/S0031-9422(98)00130-7
Journal NLM ID: 0151434
Publisher: Elsevier
Institutions: Laboratoire de Génie Biologique et Sciences des Aliments, Unité de Microbiologic et Biochimie Industrielles, Associée à l’INRA, Université de Montpellier, Montpellier, France

Cyanogenic beta-rutinoside ((R)-mandelonitrile alpha-L-rhamnopyranosyl-beta-D-glucopyranoside was isolated from fruits of Passiflora edulis. Its structure was elucidated mainly by enzymatic hydrolysis using a specific enzyme, CC-mass spectrometric analysis of trifuoroacetyl derivatives, and NMR spectroscopy.

Passiflora edulis, cyanogenesis, Passifloraceae, passion fruit, (R)-mandelonitrile alpha-L-rhamnopyranosyl-beta-D-glucopyranoside

Structure type: oligomer ; 442 [M+H]+
Location inside paper: p. 758, Scheme, compound 1a, table 1
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, FAB-MS, GC-MS, GC-EI-MS, TLC, GC, HPLC, extraction, trifluoroacetolysis, liquid chromatography, 2D NMR, enzymatic hydrolyisis, NCI-MS
Enzymes that release or process the structure: almond glycosidase, α-L-rhamnopyranosidase

Related record ID(s): 61765
NCBI Taxonomy refs (TaxIDs): 78168
Show glycosyltransferases

NMR conditions: in D2O [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
7,6	aLRhap	100.9	70.3	70.5	72.4	69.0	17.0
7	bDGlcp	101.9	73.0	75.3	69.7	75.7	66.7
	Subst	132.7	129.7	128.2	130.8	128.2	129.7	69.7	118.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
7,6	aLRhap	4.7	3.89	3.71	3.08-3.36	3.62	1.19
7	bDGlcp	4.52	3.24	3.08	3.36	3.44	3.55-3.87
	Subst	-	-	7.40-7.51	-	7.40-7.51	-	5.76	-


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
7,6	aLRhap	100.9/4.7	70.3/3.89	70.5/3.71	72.4/3.08-3.36	69.0/3.62	17.0/1.19
7	bDGlcp	101.9/4.52	73.0/3.24	75.3/3.08	69.7/3.36	75.7/3.44	66.7/3.55-3.87
	Subst			128.2/7.40-7.51		128.2/7.40-7.51		69.7/5.76

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
7,6	aLRhap	4.7	3.89	3.71	3.08 3.36	3.62	1.19
7	bDGlcp	4.52	3.24	3.08	3.36	3.44	3.55 3.87
	Subst			7.40 7.51		7.40 7.51		5.76

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
7,6	aLRhap	100.9	70.3	70.5	72.4	69.0	17.0
7	bDGlcp	101.9	73.0	75.3	69.7	75.7	66.7
	Subst	132.7	129.7	128.2	130.8	128.2	129.7	69.7	118.7

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)c3ccccc3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Passiflora edulis, cyanogenesis, Passifloraceae, passion fruit, (R)-mandelonitrile alpha-L-rhamnopyranosyl-beta-D-glucopyranoside

Structure type: oligomer ; 1017 [M+H]+
Location inside paper: p. 758, Scheme, compound 1b
Compound class: glycoside
Contained glycoepitopes: IEDB_130422,IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192,SB_61

Methods: 13C NMR, 1H NMR, FAB-MS, GC-MS, GC-EI-MS, TLC, GC, HPLC, extraction, trifluoroacetolysis, liquid chromatography, 2D NMR, enzymatic hydrolyisis, NCI-MS
Comments, role: product of trifluoroacetylation of ID: 61764

Related record ID(s): 61764
NCBI Taxonomy refs (TaxIDs): 78168
Show glycosyltransferases

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](O[C@@H](C#N)c3ccccc3)[C@H](OC(=O)C(F)(F)F)[C@@H](OC(=O)C(F)(F)F)[C@@H]2OC(=O)C(F)(F)F)[C@H](OC(=O)C(F)(F)F)[C@H](OC(=O)C(F)(F)F)[C@H]1OC(=O)C(F)(F)F

SVG MW SMILES 3D mol Ionize