Salvianolic acids

Salvianolic acids
	; Salvianolic acids A-D
Identifiers
CAS Number	A: 96574-01-5; B: 121521-90-2; C: 115841-09-3; D: 142998-47-8;
3D model (JSmol)	A: Interactive image; B: Interactive image; C: Interactive image; D: Interactive image;
ChEBI	A: CHEBI:9017; B: CHEBI:134301; C: CHEBI:140104; D: CHEBI:177612;
ChEMBL	A: ChEMBL457077; B: ChEMBL1615434; C: ChEMBL4077922;
ChemSpider	A: 4445105;
DrugBank	A: DB15246;
KEGG	A: C10492;
PubChem CID	A: 5281793; B: 6451084; C: 13991590; D: 75412558;
UNII	B: C1GQ844199; C: I16H9Z53ZL; D: 28R85321EY;
CompTox Dashboard (EPA)	A: DTXSID701316580; B: DTXSID201031347; C: DTXSID101341785; D: DTXSID801341786;
	InChI A: InChI=1S/C26H22O10/c27-18-7-2-14(11-21(18)30)1-6-17-16(4-9-20(29)25(17)33)5-10-24(32)36-23(26(34)35)13-15-3-8-19(28)22(31)12-15/h1-12,23,27-31,33H,13H2,(H,34,35)/b6-1+,10-5+/t23-/m1/s1 Key: YMGFTDKNIWPMGF-UCPJVGPRSA-N; B: InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1 Key: SNKFFCBZYFGCQN-VWUOOIFGSA-N; C: InChI=1S/C26H20O10/c27-17-5-1-13(9-20(17)30)10-23(26(33)34)35-24(32)8-4-14-2-7-19(29)25-16(14)12-22(36-25)15-3-6-18(28)21(31)11-15/h1-9,11-12,23,27-31H,10H2,(H,33,34)/b8-4+/t23-/m1/s1 Key: GCJWPRRNLSHTRY-VURDRKPISA-N; D: InChI=1S/C20H18O10/c21-13-4-1-10(7-15(13)23)8-16(20(28)29)30-18(26)6-3-11-2-5-14(22)19(27)12(11)9-17(24)25/h1-7,16,21-23,27H,8-9H2,(H,24,25)(H,28,29)/b6-3+/t16-/m1/s1 Key: KFCMFABBVSIHTB-WUTVXBCWSA-N;
	SMILES A: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C(C(=C(C=C2)O)O)/C=C/C3=CC(=C(C=C3)O)O)O)O; B: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C3[C@@H]([C@H](OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O[C@H](CC5=CC(=C(C=C5)O)O)C(=O)O)O)O; C: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C3C=C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)O)O; D: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C(C(=C(C=C2)O)O)CC(=O)O)O)O;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Salvianolic acids are a group of polyphenolic acids consisting on several combinations of caffeic acid and danshensu (salvianic acid) through ester and enol bonds. Salvianolic acids are water-soluble components produced by many species of the genus Salvia, mainly extracted from Salvia miltiorrhiza.^[1]

Structural properties

More than 10 distinct salvianolic acids (Sal), identified by letters from A to J, have been recognized. Notably, Sal-A and Sal-B are the most abundant forms. The combination of danshensu and a caffeic acid derivative or caffeic acid dimer produces several kinds of skeletons. Sal-A is formed by a molecule of danshensu and a dimer of caffeic acid. Sal-B, on the other hand, is constituted by three molecules of danshensu and one molecule of caffeic acid. Sal-C results from the combination of two molecules of danshensu, while Sal-D is characterized as a dimer of caffeic acid.^[2]

Biosynthesis and natural occurrence

The formation of salvianolic acids is closely linked to that of rosmarinic acid. They are primarily synthesized through the phenylpropanoid and tyrosine-derived branches of the phenolic acid biosynthetic pathway. Rosmarinic acid undergoes a not well-understood oxidative reaction to convert into Salvianolic acid B.^[3] This reaction involves laccases, which are widely spread in many genera such as Arabidopsis, poplars, sorghum, etc., but appears to be highly expressed in Salvia miltiorrhiza and Salvia bowleyana.^[4]

References

^ Du, Guanhua; Song, Junke; Du, Lida; Zhang, Li; Qiang, Guifen; Wang, Shoubao; Yang, Xiuying; Fang, Lianhua (2020-01-01), Du, Guanhua (ed.), "Chapter One - Chemical and pharmacological research on the polyphenol acids isolated from Danshen: A review of salvianolic acids", Advances in Pharmacology, Pharmacological Advances in Natural Product Drug Discovery, 87, Academic Press: 1–41, doi:10.1016/bs.apha.2019.12.004, PMID 32089230, S2CID 211263286, retrieved 2024-01-17
^ Ma, Lunkun; Tang, Liling; Yi, Qian (2019). "Salvianolic Acids: Potential Source of Natural Drugs for the Treatment of Fibrosis Disease and Cancer". Frontiers in Pharmacology. 10: 97. doi:10.3389/fphar.2019.00097. ISSN 1663-9812. PMC 6391314. PMID 30842735.
^ Zhou, Zheng; Li, Qing; Xiao, Liang; Wang, Yun; Feng, Jingxian; Bu, Qitao; Xiao, Ying; Hao, Kai; Guo, Meili; Chen, Wansheng; Zhang, Lei (2021-03-18). "Multiplexed CRISPR/Cas9-Mediated Knockout of Laccase Genes in Salvia miltiorrhiza Revealed Their Roles in Growth, Development, and Metabolism". Frontiers in Plant Science. 12: 647768. doi:10.3389/fpls.2021.647768. ISSN 1664-462X. PMC 8014014. PMID 33815454.
^ Li, Qing; Feng, Jingxian; Chen, Liang; Xu, Zhichao; Zhu, Yingjie; Wang, Yun; Xiao, Ying; Chen, Junfeng; Zhou, Yangyun; Tan, Hexin; Zhang, Lei; Chen, Wansheng (2019). "Genome-Wide Identification and Characterization of Salvia miltiorrhiza Laccases Reveal Potential Targets for Salvianolic Acid B Biosynthesis". Frontiers in Plant Science. 10: 435. doi:10.3389/fpls.2019.00435. ISSN 1664-462X. PMC 6463009. PMID 31024599.

[1] Du, Guanhua; Song, Junke; Du, Lida; Zhang, Li; Qiang, Guifen; Wang, Shoubao; Yang, Xiuying; Fang, Lianhua (2020-01-01), Du, Guanhua (ed.), "Chapter One - Chemical and pharmacological research on the polyphenol acids isolated from Danshen: A review of salvianolic acids", Advances in Pharmacology, Pharmacological Advances in Natural Product Drug Discovery, 87, Academic Press: 1–41, doi:10.1016/bs.apha.2019.12.004, PMID 32089230, S2CID 211263286, retrieved 2024-01-17

[2] Ma, Lunkun; Tang, Liling; Yi, Qian (2019). "Salvianolic Acids: Potential Source of Natural Drugs for the Treatment of Fibrosis Disease and Cancer". Frontiers in Pharmacology. 10: 97. doi:10.3389/fphar.2019.00097. ISSN 1663-9812. PMC 6391314. PMID 30842735.

[3] Zhou, Zheng; Li, Qing; Xiao, Liang; Wang, Yun; Feng, Jingxian; Bu, Qitao; Xiao, Ying; Hao, Kai; Guo, Meili; Chen, Wansheng; Zhang, Lei (2021-03-18). "Multiplexed CRISPR/Cas9-Mediated Knockout of Laccase Genes in Salvia miltiorrhiza Revealed Their Roles in Growth, Development, and Metabolism". Frontiers in Plant Science. 12: 647768. doi:10.3389/fpls.2021.647768. ISSN 1664-462X. PMC 8014014. PMID 33815454.

[4] Li, Qing; Feng, Jingxian; Chen, Liang; Xu, Zhichao; Zhu, Yingjie; Wang, Yun; Xiao, Ying; Chen, Junfeng; Zhou, Yangyun; Tan, Hexin; Zhang, Lei; Chen, Wansheng (2019). "Genome-Wide Identification and Characterization of Salvia miltiorrhiza Laccases Reveal Potential Targets for Salvianolic Acid B Biosynthesis". Frontiers in Plant Science. 10: 435. doi:10.3389/fpls.2019.00435. ISSN 1664-462X. PMC 6463009. PMID 31024599.

[1]

[2]

[3]

[4]

Identifiers



Salvianolic acids A-D
CAS Number	A: 96574-01-5 B: 121521-90-2 C: 115841-09-3 D: 142998-47-8
3D model (JSmol)	A: Interactive image B: Interactive image C: Interactive image D: Interactive image
ChEBI	A: CHEBI:9017 B: CHEBI:134301 C: CHEBI:140104 D: CHEBI:177612
ChEMBL	A: ChEMBL457077 B: ChEMBL1615434 C: ChEMBL4077922
ChemSpider	A: 4445105
DrugBank	A: DB15246
KEGG	A: C10492
PubChem CID	A: 5281793 B: 6451084 C: 13991590 D: 75412558
UNII	B: C1GQ844199 C: I16H9Z53ZL D: 28R85321EY
CompTox Dashboard (EPA)	A: DTXSID701316580 B: DTXSID201031347 C: DTXSID101341785 D: DTXSID801341786
InChI A: InChI=1S/C26H22O10/c27-18-7-2-14(11-21(18)30)1-6-17-16(4-9-20(29)25(17)33)5-10-24(32)36-23(26(34)35)13-15-3-8-19(28)22(31)12-15/h1-12,23,27-31,33H,13H2,(H,34,35)/b6-1+,10-5+/t23-/m1/s1 Key: YMGFTDKNIWPMGF-UCPJVGPRSA-N B: InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1 Key: SNKFFCBZYFGCQN-VWUOOIFGSA-N C: InChI=1S/C26H20O10/c27-17-5-1-13(9-20(17)30)10-23(26(33)34)35-24(32)8-4-14-2-7-19(29)25-16(14)12-22(36-25)15-3-6-18(28)21(31)11-15/h1-9,11-12,23,27-31H,10H2,(H,33,34)/b8-4+/t23-/m1/s1 Key: GCJWPRRNLSHTRY-VURDRKPISA-N D: InChI=1S/C20H18O10/c21-13-4-1-10(7-15(13)23)8-16(20(28)29)30-18(26)6-3-11-2-5-14(22)19(27)12(11)9-17(24)25/h1-7,16,21-23,27H,8-9H2,(H,24,25)(H,28,29)/b6-3+/t16-/m1/s1 Key: KFCMFABBVSIHTB-WUTVXBCWSA-N
SMILES A: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C(C(=C(C=C2)O)O)/C=C/C3=CC(=C(C=C3)O)O)O)O B: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C3[C@@H]([C@H](OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)C(=O)O[C@H](CC5=CC(=C(C=C5)O)O)C(=O)O)O)O C: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C3C=C(OC3=C(C=C2)O)C4=CC(=C(C=C4)O)O)O)O D: C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C(C(=C(C=C2)O)O)CC(=O)O)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references