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

The structure was elucidated in this paper
NCBI PubMed ID: 9559560
Publication DOI: 10.1093/oxfordjournals.pcp.a029351
Journal NLM ID: 9430925
Publisher: Tokyo: Oxford University Press
Institutions: Department of Biological Chemistry, Institute of Life Sciences, The Hebrew University, Jerusalem, Israel, Section of Plant Biology, University of California Davis, Davis, US, Biochemistry Department, Complex Carbohydrate Research Center, Life Sciences Building, University of Georgia, Athens, US, Plant Cell Biology Research Centre, School of Botany, The University of Melbourne, Parkville, Australia

A specific and highly potent inhibitor of diguanylate cyclase, the key regulatory enzyme of the cellulose synthesizing apparatus in the bacterium Acetobacter xylinum, was isolated from extracts of etiolated pea shoots (Pisum sativum). The inhibitor has been purified by a multistep procedure, and sufficient amounts of highly purified compound (3-8 mg) for spectral analysis were obtained. The structure of this compound was established as 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1 --> 2)-beta-D-glucuronopyranosyl soyasapogenol B 22-O-alpha-D-glucopyranoside. The structure was elucidated on the basis of susceptibility to various enzymes, chemical and spectral methods, such as GC-MS, FAB-MS, and the following types of 2D-NMR: COSY, ROESY, TOCSEY, HMQC, HMBC analyses, An identical or a very similar compound with identical biological activity was also isolated from A. xylinum, strongly suggesting that at least certain aspects of cellulose synthesis in the bacteria and in higher plants may be regulated in a similar manner. The content of this saponin in etiolated plants was about 0.04 mu mol (g fresh tissue)(-1).

inhibitor, triterpenoid saponin, Actobacter xylinun, diguanylate cyclase, Pisum sativum

Structure type: oligomer ; 1104, 941
Location inside paper: Fig. 2, Structure 2, Structure 3, table 2
Compound class: triterpenoid glycoside
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: methylation, GLC-MS, FAB-MS, GC-MS, inhibition studies, TLC, acid hydrolysis, HPLC, extraction, ROESY, TOCSY, DEAE, reversed-phase chromatography, phenol-sulfuric acid assay, DQF-COSY, centrifugation, HSQC, HBBC
Biological activity: glucosylated structure 3 inhibits diguanylate cyclase of Acetobacter xylinum; concentration of 5 μM is required for 50% inhibition of enzyme
Comments, role: structure 2 and structure 3 were obtained as mixture; NMR signals given for mixture sample

Related record ID(s): 61487
NCBI Taxonomy refs (TaxIDs): 3888
Show glycosyltransferases

NMR conditions: in D2O [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
3,2,2	aLRhap	102.18	?	?	?	?	18.08
3,2	bDGalp	102.03	?	?	?	?	?
3	bDGlcpA	105.43	?	?	?	?	?
22	%aDGlcp	93.42	?	?	?	?	?
	xXSoyasapogenolB	39.82	?	?	?	57.47	19.2	34.34	?	49.0	?	26.97	?	?	?	?	?	?	46.88	47.60	?	42.3	?	23.3	64.2	16.23	17.30	25.26-26.37	20.20-21.27	32.48-33.68	28.20-28.97


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
3,2,2	aLRhap	5.144	3.918	3.727	3.394	4.103	1.280
3,2	bDGalp	4.875	3.653	3.539	3.716	?	?
3	bDGlcpA	4.449	3.758	3.604	3.432	3.544	-
22	%aDGlcp	5.393	3.427	3.362	3.707	3.832	3.832
	xXSoyasapogenolB	1.048-1.645	1.823-2.123	3.41	-	0.95	1.386-1.566	1.40	-	1.59	-	1.89	5.21-5.25	-	-	1.045	1.317-1.772	-	2.053	0.970-1.750	-	1.434-1.451	3.392-3.476	1.126	3.140-4.190	0.920	0.976	1.128-1.160	0.830	0.910-0.920	0.980-1.017


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
3,2,2	aLRhap	102.18/5.144	?/3.918	?/3.727	?/3.394	?/4.103	18.08/1.280
3,2	bDGalp	102.03/4.875	?/3.653	?/3.539	?/3.716	?/?	?/?
3	bDGlcpA	105.43/4.449	?/3.758	?/3.604	?/3.432	?/3.544	
22	%aDGlcp	93.42/5.393	?/3.427	?/3.362	?/3.707	?/3.832	?/3.832
	xXSoyasapogenolB	39.82/1.048-1.645	?/1.823-2.123	?/3.41		57.47/0.95	19.2/1.386-1.566	34.34/1.40		49.0/1.59		26.97/1.89	?/5.21-5.25			?/1.045	?/1.317-1.772		46.88/2.053	47.60/0.970-1.750		42.3/1.434-1.451	?/3.392-3.476	23.3/1.126	64.2/3.140-4.190	16.23/0.920	17.30/0.976	25.26-26.37/1.128-1.160	20.20-21.27/0.830	32.48-33.68/0.910-0.920	28.20-28.97/0.980-1.017

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H9	H11	H12	H15	H16	H18	H19	H21	H22	H23	H24	H25	H26	H27	H28	H29	H30
3,2,2	aLRhap	5.144	3.918	3.727	3.394	4.103	1.280
3,2	bDGalp	4.875	3.653	3.539	3.716	?	?
3	bDGlcpA	4.449	3.758	3.604	3.432	3.544
22	%aDGlcp	5.393	3.427	3.362	3.707	3.832	3.832
	xXSoyasapogenolB	1.048 1.645	1.823 2.123	3.41		0.95	1.386 1.566	1.40	1.59	1.89	5.21 5.25	1.045	1.317 1.772	2.053	0.970 1.750	1.434 1.451	3.392 3.476	1.126	3.140 4.190	0.920	0.976	1.128 1.160	0.830	0.910 0.920	0.980 1.017

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
3,2,2	aLRhap	102.18	?	?	?	?	18.08
3,2	bDGalp	102.03	?	?	?	?	?
3	bDGlcpA	105.43	?	?	?	?	?
22	%aDGlcp	93.42	?	?	?	?	?
	xXSoyasapogenolB	39.82	?	?	?	57.47	19.2	34.34	?	49.0	?	26.97	?	?	?	?	?	?	46.88	47.60	?	42.3	?	23.3	64.2	16.23	17.30	25.26 26.37	20.20 21.27	32.48 33.68	28.20 28.97

The spectrum also has 32 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](O[C@@H]3[C@@H](O)[C@H](O)[C@@H](C(=O)O)O[C@H]3O[C@H]3CC[C@@]4(C)[C@@H](CC[C@]5(C)[C@@H]4CC=C4[C@@H]6CC(C)(C)C[C@@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@]6(C)CC[C@]45C)[C@@]3(C)CO)O[C@H](CO)[C@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize