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

The structure was elucidated in this paper
Publication DOI: 10.1016/S0031-9422(97)00584-0
Journal NLM ID: 0151434
Publisher: Elsevier
Institutions: Lehrstuhl für Pharmazeutische Chemie der Universität Freiburg, Freiburg, Germany, Herbarium BTU, Institut für Biologie, Berlin, Germany

A new spirocyclic nortriterpene, 22-acetoxy-15-deoxo-eucosterol, was isolated together with a corresponding pentaglycoside from the bulbs of Veltheimia viridifolia. The structures of the isolated compounds were elucidated by spectroscopic methods including 1D- and 2D-1H NMR, 13C NMR, 1D-INEPT, 1D- and 2D-TOCSY, HSQC, HMBC, ROESY experiments, FAB- and HRESI- mass spectrometry.

22-acetoxy-15-deoxo-eucosterol and 22-acetoxy-15-deoxo-eucosterol pentaglycoside, Hyacinthaceae, Veltheimia viridifolia

Structure type: oligomer ; 1289 [M+Na]+
Location inside paper: p. 430, Scheme, compound 2, table 1, table 3
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_153543,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, FAB-MS, extraction, optical rotation measurement, TOCSY, melting point determination, HMBC, DEPT, HSQC, HETCOR, INEPT, HR-ESI, ROSEY

NCBI Taxonomy refs (TaxIDs): 81803
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
3,6,2,2	bDApif	111.2	77.7	79.5	74.8	64.9
3,6,2,3	bDGlcp	104.5	75.1	78.3	71.5	78.4	62.3
3,6,2	bDGlcp	103.6	81.1	88.2	69.3	77.5	61.9
3,6	aLArap	101.8	80.7	72.4	67.3	64.4
3	bDGlcp	106.1	75.4	78.4	72.4	76.0	69.0
22	Ac	169.8	20.8
	Subst	35.8	27.5	89.1	44.4	51.8	18.8	26.9	135.1	134.8	36.8	21.2	25.3	49.9	50.4	32.6	40.1	97.5	19.3	19.7	49.5	15.4	82.0	85.0	208.8	33.3	7.6	23.1	63.2	26.5


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27	H28	H29	H30	H31	H32	H33	H34	H35	H36	H37	H38	H39
3,6,2,2	bDApif	6.22	4.70	-	4.32	4.15-4.79
3,6,2,3	bDGlcp	5.14	3.98	4.18	4.09	4.00	4.22-4.52
3,6,2	bDGlcp	5.06	4.00	4.03	4.03	3.69	4.17-4.32
3,6	aLArap	5.10	4.48	4.40	4.44	3.76-4.29
3	bDGlcp	4.98	3.96	4.16	4.14	4.07	4.55-4.60
22	Ac	-	2.00
	Subst	1.20	1.76	2.34	2.05	3.61	-	1.31	1.84	1.52	2.05	2.09	-	-	-	2.22	2.03	2.44	1.51	-	-	1.51	1.76	2.62	2.00	-	0.92	0.98	2.40	1.10	5.40	4.98	-	2.57	2.57	1.09	1.56	3.66	4.44	1.59


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18	C19/H19	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27	C28/H28	C29/H29	C30/H30	C31/H31	C32/H32	C33/H33	C34/H34	C35/H35	C36/H36	C37/H37	C38/H38	C39/H39
3,6,2,2	bDApif	111.2/6.22	77.7/4.70		74.8/4.32	64.9/4.15-4.79
3,6,2,3	bDGlcp	104.5/5.14	75.1/3.98	78.3/4.18	71.5/4.09	78.4/4.00	62.3/4.22-4.52
3,6,2	bDGlcp	103.6/5.06	81.1/4.00	88.2/4.03	69.3/4.03	77.5/3.69	61.9/4.17-4.32
3,6	aLArap	101.8/5.10	80.7/4.48	72.4/4.40	67.3/4.44	64.4/3.76-4.29
3	bDGlcp	106.1/4.98	75.4/3.96	78.4/4.16	72.4/4.14	76.0/4.07	69.0/4.55-4.60
22	Ac		20.8/2.00
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H15	H16	H17	H18	H21	H22	H23	H24	H26	H27	H28	H29	H30	H31	H33	H34	H35	H36	H37	H38	H39
3,6,2,2	bDApif	6.22	4.70		4.32	4.15 4.79
3,6,2,3	bDGlcp	5.14	3.98	4.18	4.09	4.00	4.22 4.52
3,6,2	bDGlcp	5.06	4.00	4.03	4.03	3.69	4.17 4.32
3,6	aLArap	5.10	4.48	4.40	4.44	3.76 4.29
3	bDGlcp	4.98	3.96	4.16	4.14	4.07	4.55 4.60
22	Ac		2.00
	Subst	1.20	1.76	2.34	2.05	3.61		1.31	1.84	1.52	2.05	2.09	2.22	2.03	2.44	1.51	1.51	1.76	2.62	2.00	0.92	0.98	2.40	1.10	5.40	4.98	2.57	2.57	1.09	1.56	3.66	4.44	1.59

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
3,6,2,2	bDApif	111.2	77.7	79.5	74.8	64.9
3,6,2,3	bDGlcp	104.5	75.1	78.3	71.5	78.4	62.3
3,6,2	bDGlcp	103.6	81.1	88.2	69.3	77.5	61.9
3,6	aLArap	101.8	80.7	72.4	67.3	64.4
3	bDGlcp	106.1	75.4	78.4	72.4	76.0	69.0
22	Ac	169.8	20.8
	Subst	35.8	27.5	89.1	44.4	51.8	18.8	26.9	135.1	134.8	36.8	21.2	25.3	49.9	50.4	32.6	40.1	97.5	19.3	19.7	49.5	15.4	82.0	85.0	208.8	33.3	7.6	23.1	63.2	26.5

There is only one chemically distinct structure:

CCC(=O)[C@H]1O[C@@]2(CC[C@@]3(C)C4CCC5[C@@](C)(CO)[C@@H](O[C@@H]6O[C@H](CO[C@@H]7OC[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H]7O[C@@H]7OC[C@](O)(CO)[C@H]7O)[C@@H](O)[C@H](O)[C@H]6O)CC[C@]5(C)C4CC[C@@]32C)[C@H](C)[C@H]1OC(C)=O

SVG MW SMILES 3D mol Ionize