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MedKoo Cat#: 600108 | Name: Andrographolide
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Description:

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

Andrographolide is a labdane diterpenoid that is the main bioactive component of the medicinal plant Andrographis paniculata. Andrographolide is an extremely bitter substance extracted from the stem and leaves of A. paniculata. Andrographolide is used experimentally in different areas of research including cell signaling, immunomodulation, and stroke. Several targets are described for andrographolide, including the interference of transcription factors NF-κB, AP-1, and HIF-1 and signaling pathways such as PI3K/Akt, MAPK, and JAK/STAT. In addition, an increase in the Nrf2 (nuclear factor erythroid 2-related factor 2) signaling pathway also supports its antioxidant and anti-inflammatory properties.

Chemical Structure

Andrographolide
Andrographolide
CAS#5508-58-7

Theoretical Analysis

MedKoo Cat#: 600108

Name: Andrographolide

CAS#: 5508-58-7

Chemical Formula: C20H30O5

Exact Mass: 350.2093

Molecular Weight: 350.45

Elemental Analysis: C, 68.54; H, 8.63; O, 22.83

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
3-dehydroandrographolide; Andrographis; Andrographiside aglycon
IUPAC/Chemical Name
(S,E)-4-Hydroxy-3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethylidene)dihydrofuran-2(3H)-one
InChi Key
BOJKULTULYSRAS-OTESTREVSA-N
InChi Code
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
SMILES Code
O=C1OC[C@@H](O)/C1=C\C[C@@H]2C(CC[C@]3([H])[C@](C)(CO)[C@H](O)CC[C@@]23C)=C
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 350.45 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
1: Burgos RA, Alarcón P, Quiroga J, Manosalva C, Hancke J. Andrographolide, an Anti-Inflammatory Multitarget Drug: All Roads Lead to Cellular Metabolism. Molecules. 2020 Dec 22;26(1):5. doi: 10.3390/molecules26010005. PMID: 33374961; PMCID: PMC7792620. 2: Dai Y, Chen SR, Chai L, Zhao J, Wang Y, Wang Y. Overview of pharmacological activities of Andrographis paniculata and its major compound andrographolide. Crit Rev Food Sci Nutr. 2019;59(sup1):S17-S29. doi: 10.1080/10408398.2018.1501657. Epub 2018 Sep 10. PMID: 30040451. 3: Zhang H, Li S, Si Y, Xu H. Andrographolide and its derivatives: Current achievements and future perspectives. Eur J Med Chem. 2021 Nov 15;224:113710. doi: 10.1016/j.ejmech.2021.113710. Epub 2021 Jul 20. PMID: 34315039. 4: Zeng B, Wei A, Zhou Q, Yuan M, Lei K, Liu Y, Song J, Guo L, Ye Q. Andrographolide: A review of its pharmacology, pharmacokinetics, toxicity and clinical trials and pharmaceutical researches. Phytother Res. 2022 Jan;36(1):336-364. doi: 10.1002/ptr.7324. Epub 2021 Nov 24. PMID: 34818697. 5: Geng J, Liu W, Gao J, Jiang C, Fan T, Sun Y, Qin ZH, Xu Q, Guo W, Gao J. Andrographolide alleviates Parkinsonism in MPTP-PD mice via targeting mitochondrial fission mediated by dynamin-related protein 1. Br J Pharmacol. 2019 Dec;176(23):4574-4591. doi: 10.1111/bph.14823. Epub 2019 Nov 14. PMID: 31389613; PMCID: PMC6932945. 6: Gao J, Peng S, Shan X, Deng G, Shen L, Sun J, Jiang C, Yang X, Chang Z, Sun X, Feng F, Kong L, Gu Y, Guo W, Xu Q, Sun Y. Inhibition of AIM2 inflammasome- mediated pyroptosis by Andrographolide contributes to amelioration of radiation- induced lung inflammation and fibrosis. Cell Death Dis. 2019 Dec 20;10(12):957. doi: 10.1038/s41419-019-2195-8. PMID: 31862870; PMCID: PMC6925222. 7: Patil R, Jain V. Andrographolide: A Review of Analytical Methods. J Chromatogr Sci. 2021 Jan 14;59(2):191-203. doi: 10.1093/chromsci/bmaa091. PMID: 33221827. 8: Ahmed S, Kwatra M, Ranjan Panda S, Murty USN, Naidu VGM. Andrographolide suppresses NLRP3 inflammasome activation in microglia through induction of parkin-mediated mitophagy in in-vitro and in-vivo models of Parkinson disease. Brain Behav Immun. 2021 Jan;91:142-158. doi: 10.1016/j.bbi.2020.09.017. Epub 2020 Sep 22. PMID: 32971182. 9: Zhang J, Zheng Y, Zhao Y, Zhang Y, Liu Y, Ma F, Wang X, Fu J. Andrographolide ameliorates neuroinflammation in APP/PS1 transgenic mice. Int Immunopharmacol. 2021 Jul;96:107808. doi: 10.1016/j.intimp.2021.107808. Epub 2021 May 30. PMID: 34162168. 10: Kumar G, Singh D, Tali JA, Dheer D, Shankar R. Andrographolide: Chemical modification and its effect on biological activities. Bioorg Chem. 2020 Jan;95:103511. doi: 10.1016/j.bioorg.2019.103511. Epub 2019 Dec 17. PMID: 31884143. 11: Hao M, Lv M, Xu H. Andrographolide: Synthetic Methods and Biological Activities. Mini Rev Med Chem. 2020;20(16):1633-1652. doi: 10.2174/1389557520666200429100326. PMID: 32348215. 12: Agrawal P, Nair MS. An insight into the pharmacological and analytical potential of Andrographolide. Fundam Clin Pharmacol. 2022 Aug;36(4):586-600. doi: 10.1111/fcp.12757. Epub 2022 Jan 23. PMID: 35001431. 13: Wang DW, Xiang YJ, Wei ZL, Yao H, Shen T. Andrographolide and its derivatives are effective compounds for gastrointestinal protection: a review. Eur Rev Med Pharmacol Sci. 2021 Mar;25(5):2367-2382. doi: 10.26355/eurrev_202103_25276. PMID: 33755974. 14: Enmozhi SK, Raja K, Sebastine I, Joseph J. Andrographolide as a potential inhibitor of SARS-CoV-2 main protease: an in silico approach. J Biomol Struct Dyn. 2021 Jun;39(9):3092-3098. doi: 10.1080/07391102.2020.1760136. Epub 2020 May 5. PMID: 32329419; PMCID: PMC7212536. 15: Latif R, Wang CY. Andrographolide as a potent and promising antiviral agent. Chin J Nat Med. 2020 Oct;18(10):760-769. doi: 10.1016/S1875-5364(20)60016-4. PMID: 33039055. 16: Gupta S, Mishra KP, Gupta R, Singh SB. Andrographolide - A prospective remedy for chikungunya fever and viral arthritis. Int Immunopharmacol. 2021 Oct;99:108045. doi: 10.1016/j.intimp.2021.108045. Epub 2021 Aug 12. PMID: 34435582. 17: Mishra SK, Tripathi S, Shukla A, Oh SH, Kim HM. Andrographolide and analogues in cancer prevention. Front Biosci (Elite Ed). 2015 Jan 1;7(2):255-66. doi: 10.2741/E732. PMID: 25553378. 18: Wang W, Yang Y, Liu Y, Sun D, Li H, Chen L. Recent Progress in Andrographolide Derivatization: Structural Modification and Biological Activity. Mini Rev Med Chem. 2022;22(11):1559-1584. doi: 10.2174/1389557521666211022150032. PMID: 34719362. 19: Liu MY, Li HJ, Yang C, Zang WD, Liu ZD, Zhang L, Li PH, Zhu YJ, Zhao YY, Liu RZ, Gao YZ. Insight into the pharmacological effects of andrographolide in musculoskeletal disorders. Biomed Pharmacother. 2022 Feb;146:112583. doi: 10.1016/j.biopha.2021.112583. Epub 2021 Dec 23. PMID: 34954644. 20: Ren X, Xu W, Sun J, Dong B, Awala H, Wang L. Current Trends on Repurposing and Pharmacological Enhancement of Andrographolide. Curr Med Chem. 2021;28(12):2346-2368. doi: 10.2174/0929867327666200810135604. PMID: 32778020.

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