Protosappanin A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 461788

CAS#: 102036-28-2

Description: Protosappanin A is an immunosuppressive ingredient of the medicinal herb Caesalpinia sappan L.

Chemical Structure

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Protosappanin A
CAS# 102036-28-2
Instruction

Theoretical Analysis

MedKoo Cat#: 461788
Name: Protosappanin A
CAS#: 102036-28-2
Chemical Formula: C15H12O5
Exact Mass: 272.07
Molecular Weight: 272.250
Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Protosappanin A; Sappanol B;

IUPAC/Chemical Name: 3,10,11-trihydroxy-6H-dibenzo[b,d]oxocin-7(8H)-one

InChi Key: MUKYVRVYBBYJSI-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H12O5/c16-9-1-2-11-12-6-14(19)13(18)4-8(12)3-10(17)7-20-15(11)5-9/h1-2,4-6,16,18-19H,3,7H2

SMILES Code: O=C1CC2=CC(O)=C(O)C=C2C3=CC=C(O)C=C3OC1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 272.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhang M, He J, Hou J, Wu J, Sun M, Cui J, Tian J, Jiang M, Yu B. The immunosuppressant Protosappanin A diminished recipient T cell migration into allograft via inhibition of IP-10 in rat heart transplant. PLoS One. 2014 May 5;9(5):e96138. doi: 10.1371/journal.pone.0096138. eCollection 2014. PubMed PMID: 24798458; PubMed Central PMCID: PMC4010525.

2: Zhang M, Zhang S, Wu J, Sun Y, Li L, Du W, Liu J, Hou J, Yu B. The Immunosuppressant Protosappanin A Promotes Dendritic Cell-Mediated Expansion of Alloantigen-Specific Tregs and Prolongs Allograft Survival in Rats. PLoS One. 2013 Jun 26;8(6):e66336. doi: 10.1371/journal.pone.0066336. Print 2013. PubMed PMID: 23840445; PubMed Central PMCID: PMC3694094.

3: Liu J, Zhou X, Wang C, Fu W, Chu W, Sun Z. Total synthesis of protosappanin A and its derivatives via palladium catalyzed ortho C-H activation/C-C cyclization under microwave irradiation. Chem Commun (Camb). 2016 Apr 14;52(29):5152-5. doi: 10.1039/c6cc01149g. Epub 2016 Mar 21. PubMed PMID: 26997503.

4: Zeng KW, Zhao MB, Ma ZZ, Jiang Y, Tu PF. Protosappanin A inhibits oxidative and nitrative stress via interfering the interaction of transmembrane protein CD14 with Toll-like receptor-4 in lipopolysaccharide-induced BV-2 microglia. Int Immunopharmacol. 2012 Dec;14(4):558-69. doi: 10.1016/j.intimp.2012.09.004. Epub 2012 Sep 21. PubMed PMID: 23000519.

5: Wu J, Zhang M, Jia H, Huang X, Zhang Q, Hou J, Bo Y. Protosappanin A induces immunosuppression of rats heart transplantation targeting T cells in grafts via NF-kappaB pathway. Naunyn Schmiedebergs Arch Pharmacol. 2010 Jan;381(1):83-92. doi: 10.1007/s00210-009-0461-5. Epub 2009 Nov 19. PubMed PMID: 19924402.

6: Wu J, Hou JB, Zhang MM, Zou YP, Yu B. Protosappanin a, an immunosuppressive constituent from a Chinese herb, prolongs graft survival and attenuates acute rejection in rat heart allografts. Transplant Proc. 2008 Dec;40(10):3719-22. doi: 10.1016/j.transproceed.2008.06.097. PubMed PMID: 19100473.

7: Wang Z, Sun JB, Qu W, Guan FQ, Li LZ, Liang JY. Caesappin A and B, two novel protosappanins from Caesalpinia sappan L. Fitoterapia. 2014 Jan;92:280-4. doi: 10.1016/j.fitote.2013.12.004. Epub 2013 Dec 12. PubMed PMID: 24334102.

8: Tewtrakul S, Chaniad P, Pianwanit S, Karalai C, Ponglimanont C, Yodsaoue O. Anti-HIV-1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia  sappan L. Phytother Res. 2015 May;29(5):724-9. doi: 10.1002/ptr.5307. Epub 2015 Feb 11. PubMed PMID: 25676492.

9: Sasaki Y, Hosokawa T, Nagai M, Nagumo S. In vitro study for inhibition of NO production about constituents of Sappan Lignum. Biol Pharm Bull. 2007 Jan;30(1):193-6. PubMed PMID: 17202686.

10: Washiyama M, Sasaki Y, Hosokawa T, Nagumo S. Anti-inflammatory constituents of Sappan Lignum. Biol Pharm Bull. 2009 May;32(5):941-4. PubMed PMID: 19420769.

11: Sasaki Y, Suzuki M, Matsumoto T, Hosokawa T, Kobayashi T, Kamata K, Nagumo S. Vasorelaxant activity of Sappan Lignum constituents and extracts on rat aorta and mesenteric artery. Biol Pharm Bull. 2010;33(9):1555-60. PubMed PMID: 20823574.

12: Zuo GY, Han ZQ, Han J, Hao XY, Tang HS, Wang GC. Antimicrobial activity and synergy of antibiotics with two biphenyl compounds, protosappanins A and B from Sappan Lignum against methicillin-resistant Staphylococcus aureus strains. J Pharm Pharmacol. 2015 Oct;67(10):1439-47. doi: 10.1111/jphp.12433. Epub 2015 Apr 29. PubMed PMID: 25920539.

13: Fu LC, Huang XA, Lai ZY, Hu YJ, Liu HJ, Cai XL. A new 3-benzylchroman derivative from Sappan Lignum (Caesalpinia sappan). Molecules. 2008 Aug 28;13(8):1923-30. PubMed PMID: 18794793.

14: Uddin GM, Kim CY, Chung D, Kim KA, Jung SH. One-step isolation of sappanol and brazilin from Caesalpinia sappan and their effects on oxidative stress-induced retinal death. BMB Rep. 2015 May;48(5):289-94. PubMed PMID: 25248564; PubMed Central PMCID: PMC4578569.

15: Nguyen MT, Awale S, Tezuka Y, Tran QL, Kadota S. Xanthine oxidase inhibitors from the heartwood of Vietnamese Caesalpinia sappan. Chem Pharm Bull (Tokyo). 2005 Aug;53(8):984-8. PubMed PMID: 16079532.

16: Xu H, Zhou ZH, Yang JS. [Compounds from Caesalpinia sappan L]. Zhongguo Zhong Yao Za Zhi. 1994 Aug;19(8):485-6, 511. Chinese. PubMed PMID: 7980861.

17: Liu AL, Shu SH, Qin HL, Lee SM, Wang YT, Du GH. In vitro anti-influenza viral activities of constituents from Caesalpinia sappan. Planta Med. 2009 Mar;75(4):337-9. doi: 10.1055/s-0028-1112208. Epub 2009 Jan 15. PubMed PMID: 19148862.

18: Niranjan Reddy VL, Ravikanth V, Jansi Lakshmi VV, Suryanarayan Murty U, Venkateswarlu Y. Inhibitory activity of homoisoflavonoids from Caesalpinia sappan against Beauveria bassiana. Fitoterapia. 2003 Sep;74(6):600-2. PubMed PMID: 12946725.

19: Wang LC, Liao LX, Zhao MB, Dong X, Zeng KW, Tu PF. Protosappanin A exerts anti-neuroinflammatory effect by inhibiting JAK2-STAT3 pathway in lipopolysaccharide-induced BV2 microglia. Chin J Nat Med. 2017 Sep;15(9):674-679. doi: 10.1016/S1875-5364(17)30096-1. PubMed PMID: 28991528.

20: Huang Y, Qi Y, Du J, Zhang D. Protosappanin A protects against atherosclerosis via anti- hyperlipidemia, anti-inflammation and NF-κB signaling pathway in hyperlipidemic rabbits. Iran J Basic Med Sci. 2018 Jan;21(1):33-38. doi: 10.22038/IJBMS.2017.18840.5029. PubMed PMID: 29372034; PubMed Central PMCID: PMC5776434.