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Danshensu

Danshensu
Names
IUPAC name
(2R)-3-(3,4-Dihydroxyphenyl)lactic acid
Other names
Salvianic acid A
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.231.388 Edit this at Wikidata
EC Number
  • 804-698-5
  • Na salt: 804-287-0
KEGG
UNII
  • InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)/t8-/m1/s1
    Key: PAFLSMZLRSPALU-MRVPVSSYSA-N
  • Na salt: InChI=1S/C9H10O5.Na/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14;/h1-3,8,10-12H,4H2,(H,13,14);/q;+1/p-1
    Key: ZMMKVDBZTXUHFO-UHFFFAOYSA-M
  • C1=CC(=C(C=C1C[C@H](C(=O)O)O)O)O
  • Na salt: C1=CC(=C(C=C1CC(C(=O)[O-])O)O)O.[Na+]
Properties
C9H10O5
Molar mass 198.174 g·mol−1
Melting point 84–86 °C (183–187 °F; 357–359 K) [1]
Related compounds
Related compounds
 Protocatechuic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Danshensu or salvianic acid A is an alpha hydroxy carboxylic acid. It is found in the plants Salvia miltiorrhiza, and Melissa officinalis. It is a component of some traditional Chinese medicine.[2]

It was discovered in the water soluble extract of roots of Salvia miltiorrhiza.[3][4] The substance can dissolve in water, methanol, ethanol, ethyl acetate and acetone. In practice the roots are extracted with boiling water. Then ethanol is added to bring the concentration up to %70 ethanol. This causes precipitation of protein, starch and polysaccharides. Chloroform then extracts coloured chemicals from the alcoholic solution.[4]

Danshensu as a racemic form has been made from protocatechuic aldehyde.[4]

Reactions

Danshensu is sensitive to air or alkaline conditions. It oxidises, polymerises and darkens on exposure.[4]

Danshensu can have its hydroxy groups methylated on treatment with dimethylsulfate.[4] In acid conditions it can convert to salvianolic acid C.[4]

Pharmacology

Danshensu dilates cardiac arteries.[5]

It can be sold as a sodium salt.

See also

References

  1. ^ Zhou, Jiaju; Xie, Guirong; Yan, Xinjian (21 February 2011). Encyclopedia of Traditional Chinese Medicines - Molecular Structures, Pharmacological Activities, Natural Sources and Applications: Vol. 2: Isolated Compounds D-G. Springer Science & Business Media. pp. 6–7. ISBN 978-3-642-16738-6.
  2. ^ Cao, Hong-Ying; Ding, Rui-Lin; Li, Meng; Yang, Mao-Nan; Yang, Ling-Lin; Wu, Jing-Bo; Yang, Bo; Wang, Jing; Luo, Cui-Lian; Wen, Qing-Lian (February 2017). "Danshensu, a major water-soluble component of Salvia miltiorrhiza, enhances the radioresponse for Lewis Lung Carcinoma xenografts in mice". Oncology Letters. 13 (2): 605–612. doi:10.3892/ol.2016.5508. PMC 5351344. PMID 28356936.
  3. ^ Lian-niang, Li; Rui, Tan; Wei-ming, Chen (June 1984). "Salvianolic Acid A, a New Depside from Roots of Salvia miltiorrhiza". Planta Medica. 50 (3): 227–228. Bibcode:1984PlMed..50..227L. doi:10.1055/s-2007-969684. PMID 17340301. S2CID 10164834.
  4. ^ a b c d e f Li, Lianniang (2015). "Water Soluble Components of Danshen". Dan Shen (Salvia miltiorrhiza) in Medicine: Volume 1. Biology and Chemistry. Springer Netherlands. pp. 97–117. doi:10.1007/978-94-017-9469-5_7. ISBN 978-94-017-9469-5.
  5. ^ Liu, Guang; Zhang, Qianqian; Zhang, Jinli; Zhang, Ning (May 2020). "Preventive but nontherapeutic effect of danshensu on hypoxic pulmonary hypertension". Journal of International Medical Research. 48 (5): 030006052091421. doi:10.1177/0300060520914218. PMC 7235679. PMID 32419546.

Extra reading

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