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Taxonomic group: fungi / Mucoromycota (Phylum: Mucoromycota)

The structure was elucidated in this paper
Publication DOI: 10.1039/c5ra09745b
Journal NLM ID: 101581657
Publisher: Cambridge, UK: Royal Society of Chemistry
Correspondence: yemin

bjmu.edu.cn
Institutions: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China

Tanshinone IIA (TIIA) is a natural product with significant anti-atherogenic activities. However, poor water-solubility and low bioavailability hinder its further exploitation as a drug candidate. In this study, microbial transformation of TIIA by Cunninghamella elegans AS 3.2028 was conducted to obtain two new glycosylated derivatives. Their structures were identified as hydroquinone TIIA 11-O-β-D-glucopyranoside (1) and hydroquinone TIIA 12-O-β-D-glucopyranoside (2) based on extensive NMR and MS spectral analyses. The solubility of 1 in 50% MeOH-H2O solution was approximately 50-fold that of TIIA, and 1 showed remarkably improved oral absorption in mice. Furthermore, 1 and 2 exhibited similar Nrf2 activation activity to TIIA

glycosylation, biotransformation, Cunninghamella elegans, tanshinone IIA

Structure type: monomer ; 459.2008 [M+H]+
C₂₅H₃₀O₈
Location inside paper: Fig. 2, Fig. 3, 1, Table 1, 1
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, MS/MS, biological assays, HPLC, UV, optical rotation measurement, column chromatography, cell growth, antioxidant activities, HR-ESI-MS, HMBC, LC, HPLC-DAD, IC-PAD, LC-SRM-MS
Biological activity: compound exhibits similar antioxidant activities to TIIA and significantly activates Nrf2 transcription in a concentration-dependent manner. Glycosylation of TIIA remarkably increases the oral absorption of TIIA
Synthetic data: enzymatic in vivo
Comments, role: atom enumeration is according to the Fig. 3 in the paper

Related record ID(s): 47892
NCBI Taxonomy refs (TaxIDs): 4853
Show glycosyltransferases

NMR conditions: in DMSO-d6 [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
11	bDGlcp	107.6	74.1	76.1	69.8	77.0	61.2
	Subst	31.0	20.0	38.8	34.7	142.7	123.4	116.7	114.2	126.2	132.4	136.1	142.7	115.3	148.6	116.3	141.1	9.6	31.5	32.5


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19
11	bDGlcp	4.41	3.43	3.25	3.21	3.04	3.44-3.57
	Subst	2.96-3.98	1.50-1.80	1.66	-	-	7.43	7.83	-	-	-	-	-	-	-	-	7.73	2.38	1.30	1.29


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
11	bDGlcp	107.6/4.41	74.1/3.43	76.1/3.25	69.8/3.21	77.0/3.04	61.2/3.44-3.57
	Subst	31.0/2.96-3.98	20.0/1.50-1.80	38.8/1.66			123.4/7.43	116.7/7.83									141.1/7.73	9.6/2.38	31.5/1.30	32.5/1.29

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19
11	bDGlcp	4.41	3.43	3.25	3.21	3.04	3.44 3.57
	Subst	2.96 3.98	1.50 1.80	1.66			7.43	7.83									7.73	2.38	1.30	1.29

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19
11	bDGlcp	107.6	74.1	76.1	69.8	77.0	61.2
	Subst	31.0	20.0	38.8	34.7	142.7	123.4	116.7	114.2	126.2	132.4	136.1	142.7	115.3	148.6	116.3	141.1	9.6	31.5	32.5

There is only one chemically distinct structure:

Cc1coc2c1c(O)c(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c1c3c(ccc12)C(C)(C)CCC3

SVG MW SMILES 3D mol Ionize

bjmu.edu.cn
Institutions: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China

glycosylation, biotransformation, Cunninghamella elegans, tanshinone IIA

Structure type: monomer ; 459.2009 [M+H]+
C₂₅H₃₀O₈
Location inside paper: Fig. 3, 2, Table 1, 2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, IR, MS/MS, biological assays, HPLC, UV, optical rotation measurement, column chromatography, cell growth, antioxidant activities, HR-ESI-MS, HMBC, LC, HPLC-DAD, IC-PAD, LC-SRM-MS
Biological activity: compound exhibits similar antioxidant activities to TIIA and significantly activates Nrf2 transcription in a concentration-dependent manner
Synthetic data: enzymatic in vivo
Comments, role: atom enumeration is according to the Fig. 3 in the paper

Related record ID(s): 47891
NCBI Taxonomy refs (TaxIDs): 4853
Show glycosyltransferases

NMR conditions: in DMSO-d6 [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
12	bDGlcp	106.7	74.0	76.2	69.8	77.5	61.0
	Subst	31.0	19.8	38.3	34.5	141.9	125.8	118.1	118.6	121.9	133.7	142.9	135.0	116.3	144.6	117.2	141.4	9.6	32.0	31.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19
12	bDGlcp	4.57	3.40	3.30	3.17	3.17	3.49-3.68
	Subst	3.49	1.74	1.66	-	-	7.55	7.88	-	-	-	-	-	-	-	-	7.69	2.39	1.32	1.30


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
12	bDGlcp	106.7/4.57	74.0/3.40	76.2/3.30	69.8/3.17	77.5/3.17	61.0/3.49-3.68
	Subst	31.0/3.49	19.8/1.74	38.3/1.66			125.8/7.55	118.1/7.88									141.4/7.69	9.6/2.39	32.0/1.32	31.9/1.30

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19
12	bDGlcp	4.57	3.40	3.30	3.17	3.17	3.49 3.68
	Subst	3.49	1.74	1.66			7.55	7.88									7.69	2.39	1.32	1.30

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19
12	bDGlcp	106.7	74.0	76.2	69.8	77.5	61.0
	Subst	31.0	19.8	38.3	34.5	141.9	125.8	118.1	118.6	121.9	133.7	142.9	135.0	116.3	144.6	117.2	141.4	9.6	32.0	31.9

There is only one chemically distinct structure:

Cc1coc2c1c(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)c(O)c1c3c(ccc12)C(C)(C)CCC3

SVG MW SMILES 3D mol Ionize