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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)

The structure was elucidated in this paper
NCBI PubMed ID: 36889998
Publication DOI: 10.1016/j.jbiosc.2023.02.004
Journal NLM ID: 100888800
Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
Correspondence: T.S. Chang <cts

mail.nutn.edu.tw>
Institutions: Department of Cosmetic Science, Chia Nan University of Pharmacy and Science, Tainan 717, Taiwan, Biodiversity Research Center, Academia Sinica, Taipei 115, Taiwan, Department of Food Science, National Quemoy University, Kinmen 892, Taiwan, Department of Biological Sciences and Technology, National University of Tainan, Tainan 700, Taiwan

Ganoderma sp. contains high amounts of diverse triterpenoids; however, few triterpenoid saponins could be isolated from the medicinal fungus. To produce novel Ganoderma triterpenoid saponins, biotransformation-guided purification (BGP) process was applied to a commercial Ganoderma extract. The commercial Ganoderma extract was partially separated into three fractions by preparative high-performance liquid chromatography, and the separated fractions were then directly biotransformed by a Bacillus glycosyltransferase (BsUGT489). One of the biotransformed products could be further purified and identified as a novel saponin: ganoderic acid C2 (GAC2)-3-O-β-glucoside by nucleic magnetic resonance (NMR) and mass spectral analyses. Based on the structure of the saponin, the predicted precursor should be the GAC2, which was confirmed to be biotransformed into four saponins, GAC2-3-O-β-glucoside, GAC2-3,15-O-β-diglucoside and two unknown GAC2 monoglucosides, revealed by NMR and mass spectral analyses. GAC2-3-O-β-glucoside and GAC2-3,15-O-β-diglucoside possessed 17-fold and 200-fold higher aqueous solubility than that of GAC2, respectively. In addition, GAC2-3-O-β-glucoside retained the most anti-α-glucosidase activity of GAC2 and was comparable with that of the anti-diabetes drug (acarbose). The present study showed that the BGP process is an efficient strategy to survey novel and bioactive molecules from crude extracts of natural products.

glycosyltransferase, glycosylation, Ganoderma lucidum, biotransformation, triterpenoid

Structure type: monomer
Location inside paper: Fig. 4, table S1, compound 1 (GAC2-3-O-b-glucoside)
Trivial name: ganoderic acid C2 (GAC2)-3-O-β-glucoside
Compound class: triterpenoid saponin

Biological activity: extraction,biotransformation,column chromatography,RP-HPLC,MS,1H NMR,13C NMR,DEPT,NMR-2D
Comments, role: NMR temperature was not specified

Related record ID(s): 41404
NCBI Taxonomy refs (TaxIDs): 5315
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	bDGlcp	107.4	76.1	79.1	72.1	78.7	63.3
	Subst	35.6	27.7	88.7	39.8	50.3	29.1	69.7	160.7	142.1	39.0	200.0	53.0	47.8	55.1	72.7	37.4	49.2	20.1	17.8	33.5	20.1	50.3	209.4	47.5	36.0	178.7	18.0	20.7	28.6	17.4


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	bDGlcp	4.96	4.06	4.28	4.25	4.02	4.43-4.60
	Subst	1.04-3.02	1.99-2.36	3.47	-	1.33	1.92	4.94	-	-	-	-	2.66-2.99	-	-	5.24	1.96-2.17	-	-	-	-	-	-	-	2.61-3.11	-	-	1.36	-	-	-


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	bDGlcp	107.4/4.96	76.1/4.06	79.1/4.28	72.1/4.25	78.7/4.02	63.3/4.43-4.60
	Subst	35.6/1.04-3.02	27.7/1.99-2.36	88.7/3.47		50.3/1.33	29.1/1.92	69.7/4.94					53.0/2.66-2.99			72.7/5.24	37.4/1.96-2.17								47.5/2.61-3.11			18.0/1.36

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	bDGlcp	4.96	4.06	4.28	4.25	4.02	4.43 4.60
	Subst	1.04 3.02	1.99 2.36	3.47		1.33	1.92	4.94					2.66 2.99			5.24	1.96 2.17								2.61 3.11			1.36

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	bDGlcp	107.4	76.1	79.1	72.1	78.7	63.3
	Subst	35.6	27.7	88.7	39.8	50.3	29.1	69.7	160.7	142.1	39.0	200.0	53.0	47.8	55.1	72.7	37.4	49.2	20.1	17.8	33.5	20.1	50.3	209.4	47.5	36.0	178.7	18.0	20.7	28.6	17.4

There is only one chemically distinct structure:

C[C@@H](CC(=O)[C@@H](C)[C@H]1C[C@H](O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)[C@@H]1C[C@@H]3O)C(=O)O

SVG MW SMILES 3D mol Ionize

glycosyltransferase, glycosylation, Ganoderma lucidum, biotransformation, triterpenoid

Structure type: oligomer
Location inside paper: Fig. 4, table S1, compound 4 (GAC2-3,15-O-b-glucoside)
Trivial name: ganoderic acid C2 (GAC2)-3,15-O-β-glucoside
Compound class: triterpenoid saponin

Biological activity: extraction,biotransformation,column chromatography,RP-HPLC,MS,1H NMR,13C NMR,DEPT,NMR-2D
Comments, role: NMR temperature was not specified

Related record ID(s): 41034
NCBI Taxonomy refs (TaxIDs): 5315
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	bDGlcp	105.6	76.1	79.3	72.1	78.9	63.3
15	bDGlcp	105.6	76.1	79.3	72.1	78.9	63.3
	Subst	35.7	27.7	88.7	41.4	50.2	30.1	68.1	161.2	142.7	39.7	199.9	52.8	47.4	54.6	83.2	38.8	49.6	19.7	17.9	33.4	20.0	50.3	209.4	47.3	35.9	178.7	18.0	22.1	30.1	16.7


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	bDGlcp	4.96	4.06	4.24	4.26	4.01	4.42-4.59
15	bDGlcp	4.95	4.09	4.22	4.27	3.93	4.38-4.54
	Subst	1.05-3.05	1.95-2.36	3.47	-	1.12	1.97-2.30	5.26	-	-	-	-	2.66-2.96	-	-	5.36	2.04-2.59	1.88	1.47	1.15	2.24	0.94	2.22	-	2.54-3.07	3.28	-	1.35	1.57	1.30	1.08


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	bDGlcp	105.6/4.96	76.1/4.06	79.3/4.24	72.1/4.26	78.9/4.01	63.3/4.42-4.59
15	bDGlcp	105.6/4.95	76.1/4.09	79.3/4.22	72.1/4.27	78.9/3.93	63.3/4.38-4.54
	Subst	35.7/1.05-3.05	27.7/1.95-2.36	88.7/3.47		50.2/1.12	30.1/1.97-2.30	68.1/5.26					52.8/2.66-2.96			83.2/5.36	38.8/2.04-2.59	49.6/1.88	19.7/1.47	17.9/1.15	33.4/2.24	20.0/0.94	50.3/2.22		47.3/2.54-3.07	35.9/3.28		18.0/1.35	22.1/1.57	30.1/1.30	16.7/1.08

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H12	H15	H16	H17	H18	H19	H20	H21	H22	H24	H25	H27	H28	H29	H30
3	bDGlcp	4.96	4.06	4.24	4.26	4.01	4.42 4.59
15	bDGlcp	4.95	4.09	4.22	4.27	3.93	4.38 4.54
	Subst	1.05 3.05	1.95 2.36	3.47		1.12	1.97 2.30	5.26	2.66 2.96	5.36	2.04 2.59	1.88	1.47	1.15	2.24	0.94	2.22	2.54 3.07	3.28	1.35	1.57	1.30	1.08

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	bDGlcp	105.6	76.1	79.3	72.1	78.9	63.3
15	bDGlcp	105.6	76.1	79.3	72.1	78.9	63.3
	Subst	35.7	27.7	88.7	41.4	50.2	30.1	68.1	161.2	142.7	39.7	199.9	52.8	47.4	54.6	83.2	38.8	49.6	19.7	17.9	33.4	20.0	50.3	209.4	47.3	35.9	178.7	18.0	22.1	30.1	16.7

There is only one chemically distinct structure:

C[C@@H](CC(=O)[C@@H](C)[C@H]1C[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@]1(C)CC[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)[C@@H]1C[C@@H]3O)C(=O)O

SVG MW SMILES 3D mol Ionize