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MedKoo Cat#: 330173 | Name: Neoandrographolide
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Description:

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

Neoandrographolide is one of the principle diterpenoids isolated from A. paniculata, a well-recognized medicinal plant in Asia. Extracts from A. paniculata have been reported to exert a wide range of therapeutic actions, including immunosuppressant, antithrombotic, anti-inflammatory, antineoplastic, anti-viral, anti-bacterial, anti-diabetic, anti-oxidative stress, antipyretic, anti-edematogenic, and anti-nociceptive activities.

Chemical Structure

Neoandrographolide
Neoandrographolide
CAS#27215-14-1

Theoretical Analysis

MedKoo Cat#: 330173

Name: Neoandrographolide

CAS#: 27215-14-1

Chemical Formula: C26H40O8

Exact Mass: 480.2723

Molecular Weight: 480.60

Elemental Analysis: C, 64.98; H, 8.39; O, 26.63

Price and Availability

Size Price Availability Quantity
5mg USD 295.00 2 weeks
10mg USD 545.00 2 weeks
25mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Neoandrographolide
IUPAC/Chemical Name
3-(2-((1R,4aS,5R,8aS)-5,8a-dimethyl-2-methylene-5-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)decahydronaphthalen-1-yl)ethyl)furan-2(5H)-one
InChi Key
YGCYRQKJYWQXHG-RDNQFMDVSA-N
InChi Code
InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19-,20-,21+,22-,24-,25+,26+/m1/s1
SMILES Code
C[C@@]12[C@@]([H])([C@@](C)(CCC2)CO[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)CCC([C@H]1CCC4=CCOC4=O)=C
Appearance
Solid powder
Purity
>95% (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
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Neoandrographolide is a diterpenoid from the Andrographis paniculata (Acanthaceae).
In vitro activity:
Dealkenylated Neoandrographolide (DN) exhibited hepatoprotective, cholesterol synthesis and absorption inhibition property, and β-glucuronidase inhibition activity with a superior binding score of -42.6+/-1.5 with FXR. Reference: J Biomol Struct Dyn. 2022 Mar 7:1-10. https://pubmed.ncbi.nlm.nih.gov/35253613/
In vivo activity:
The present study aimed to evaluate the cardioprotective effect of neoandrographolide (Neo) on myocardial ischemia/reperfusion injury (I/R) mouse models and explore its possible mechanism. Compared to the I/R group, Neo significantly suppressed IMI, infarct size, inflammatory cell infiltration, cell apoptosis, inflammatory cytokines, bax, cleaved caspase-3, P-IKBa, and P-NF-κB protein expressions, and the translocation of NF-kB subunit p65 from the cytoplasm to the nucleus in vivo or in vitro. Reference: Environ Toxicol. 2021 Dec;36(12):2367-2379. https://pubmed.ncbi.nlm.nih.gov/34397165/
Solvent mg/mL mM
Solubility
DMSO 75.3 156.75
DMSO:PBS (pH 7.2) (1:1) 0.5 1.04
Ethanol 10.0 2.81
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 480.60 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:
1. Sharma R, Kumar K, Tanvi K. Dealkenylation of neoandrographolide, a phytochemical from Andrographis paniculata stimulates FXR (Farnesoid X Receptor) and enhances gallstone dissolution. J Biomol Struct Dyn. 2022 Mar 7:1-10. doi: 10.1080/07391102.2022.2048078. Epub ahead of print. PMID: 35253613. 2. Zhang J, Sun Y, Zhong LY, Yu NN, Ouyang L, Fang RD, Wang Y, He QY. Structure-based discovery of neoandrographolide as a novel inhibitor of Rab5 to suppress cancer growth. Comput Struct Biotechnol J. 2020 Nov 30;18:3936-3946. doi: 10.1016/j.csbj.2020.11.033. PMID: 33335690; PMCID: PMC7734235. 3. Liu Y, Liu Y, Zhang HL, Yu FF, Yin XR, Zhao YF, Ye F, Wu XQ. Amelioratory effect of neoandrographolide on myocardial ischemic-reperfusion injury by its anti-inflammatory and anti-apoptotic activities. Environ Toxicol. 2021 Dec;36(12):2367-2379. doi: 10.1002/tox.23350. Epub 2021 Aug 16. PMID: 34397165. 4. Batkhuu J, Hattori K, Takano F, Fushiya S, Oshiman K, Fujimiya Y. Suppression of NO production in activated macrophages in vitro and ex vivo by neoandrographolide isolated from Andrographis paniculata. Biol Pharm Bull. 2002 Sep;25(9):1169-74. doi: 10.1248/bpb.25.1169. PMID: 12230111.
In vitro protocol:
1. Sharma R, Kumar K, Tanvi K. Dealkenylation of neoandrographolide, a phytochemical from Andrographis paniculata stimulates FXR (Farnesoid X Receptor) and enhances gallstone dissolution. J Biomol Struct Dyn. 2022 Mar 7:1-10. doi: 10.1080/07391102.2022.2048078. Epub ahead of print. PMID: 35253613. 2. Zhang J, Sun Y, Zhong LY, Yu NN, Ouyang L, Fang RD, Wang Y, He QY. Structure-based discovery of neoandrographolide as a novel inhibitor of Rab5 to suppress cancer growth. Comput Struct Biotechnol J. 2020 Nov 30;18:3936-3946. doi: 10.1016/j.csbj.2020.11.033. PMID: 33335690; PMCID: PMC7734235.
In vivo protocol:
1. Liu Y, Liu Y, Zhang HL, Yu FF, Yin XR, Zhao YF, Ye F, Wu XQ. Amelioratory effect of neoandrographolide on myocardial ischemic-reperfusion injury by its anti-inflammatory and anti-apoptotic activities. Environ Toxicol. 2021 Dec;36(12):2367-2379. doi: 10.1002/tox.23350. Epub 2021 Aug 16. PMID: 34397165. 2. Batkhuu J, Hattori K, Takano F, Fushiya S, Oshiman K, Fujimiya Y. Suppression of NO production in activated macrophages in vitro and ex vivo by neoandrographolide isolated from Andrographis paniculata. Biol Pharm Bull. 2002 Sep;25(9):1169-74. doi: 10.1248/bpb.25.1169. PMID: 12230111.
1: Banerjee T, Singh A, Kumar S, Dhanani T, Gajbhiye NA, Koley TK, Maurya A, Filgona J. Ovicidal and larvicidal effects of extracts from leaves of Andrographis paniculata (Burm. f.) Wall.ex Nees against field isolates of human hookworm (Ancylostoma duodenale). J Ethnopharmacol. 2019 Feb 11. pii: S0378-8741(18)31263-7. doi: 10.1016/j.jep.2019.02.021. [Epub ahead of print] PubMed PMID: 30763693. 2: Zhang X, Wu H, Yu X, Luo H, Lu Y, Yang H, Li X, Li Z, Tang L, Wang Z. Determination of Bitterness of Andrographis Herba Based on Electronic Tongue Technology and Discovery of the Key Compounds of Bitter Substances. Molecules. 2018 Dec 19;23(12). pii: E3362. doi: 10.3390/molecules23123362. PubMed PMID: 30572573; PubMed Central PMCID: PMC6321225. 3: Sun W, Leng L, Yin Q, Xu M, Huang M, Xu Z, Zhang Y, Yao H, Wang C, Xiong C, Chen S, Jiang C, Xie N, Zheng X, Wang Y, Song C, Peters RJ, Chen S. The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide. Plant J. 2018 Nov 16. doi: 10.1111/tpj.14162. [Epub ahead of print] PubMed PMID: 30444296. 4: Li Y, Lin HX, Wang J, Yang J, Lai CJ, Wang X, Ma BW, Tang JF, Li Y, Li XL, Guo J, Gao W, Huang LQ. Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis. Org Lett. 2018 Oct 5;20(19):5999-6002. doi: 10.1021/acs.orglett.8b02146. Epub 2018 Sep 20. PubMed PMID: 30234309. 5: Wang KH, Zhang YT, Yang XW, Xu W, Zhang P, Gong Y, Liu NF. [Chemical constituents from Fukeqianjin formula]. Zhongguo Zhong Yao Za Zhi. 2018 Jun;43(11):2300-2312. doi: 10.19540/j.cnki.cjcmm.20180408.006. Chinese. PubMed PMID: 29945383. 6: Wang Y, Jiao J, Yang Y, Yang M, Zheng Q. Screening and Identification for Immunological Active Components from Andrographis Herba Using Macrophage Biospecific Extraction Coupled with UPLC/Q-TOF-MS. Molecules. 2018 Apr 30;23(5). pii: E1047. doi: 10.3390/molecules23051047. PubMed PMID: 29710865; PubMed Central PMCID: PMC6102597. 7: Singh S, Pandey P, Ghosh S, Banerjee S. Anti-cancer labdane diterpenoids from adventitious roots of Andrographis paniculata: augmentation of production prospect endowed with pathway gene expression. Protoplasma. 2018 Sep;255(5):1387-1400. doi: 10.1007/s00709-018-1211-7. Epub 2018 Mar 20. PubMed PMID: 29560544. 8: Sharma V, Kapoor KK, Mukherjee D, Gupta VK, Dhar MK, Kaul S. Camphor sulphonic acid mediated quantitative 1,3-diol protection of major Labdane diterpenes isolated from Andrographis paniculata. Nat Prod Res. 2018 Aug;32(15):1751-1759. doi: 10.1080/14786419.2017.1402313. Epub 2017 Nov 16. PubMed PMID: 29143537. 9: Nantajit D, Jetawattana S, Suriyo T, Grdina DJ, Satayavivad J. Andrographis paniculata Diterpenoids Protect against Radiation-Induced Transformation in BALB/3T3 Cells. Radiat Res. 2017 Jul;188(1):66-74. doi: 10.1667/RR14698.1. Epub 2017 May 11. PubMed PMID: 28492344. 10: Suzuki R, Matsushima Y, Okudaira N, Sakagami H, Shirataki Y. Cytotoxic Components Against Human Oral Squamous Cell Carcinoma Isolated from Andrographis paniculata. Anticancer Res. 2016 Nov;36(11):5931-5935. PubMed PMID: 27793918. 11: Pholphana N, Panomvana D, Rangkadilok N, Suriyo T, Puranajoti P, Ungtrakul T, Pongpun W, Thaeopattha S, Songvut P, Satayavivad J. Andrographis paniculata: Dissolution investigation and pharmacokinetic studies of four major active diterpenoids after multiple oral dose administration in healthy Thai volunteers. J Ethnopharmacol. 2016 Dec 24;194:513-521. doi: 10.1016/j.jep.2016.09.058. Epub 2016 Oct 3. PubMed PMID: 27702690. 12: Khan A, Sharma P, Khan F, Ajayakumar PV, Shanker K, Samad A. In silico and in vitro Studies on Begomovirus Induced Andrographolide Biosynthesis Pathway in Andrographis Paniculata for Combating Inflammation and Cancer. Mol Inform. 2016 Jul;35(6-7):253-61. doi: 10.1002/minf.201501010. Epub 2016 May 3. PubMed PMID: 27492239. 13: Liu FF, Fan CL, Huang XJ, Wang GY, Wang Y, Ye WC. [HPLC Specific Fingerprint of Alcohol Extract of Andrographis paniculata]. Zhong Yao Cai. 2015 Jul;38(7):1505-8. Chinese. PubMed PMID: 26946847. 14: Yang N, Xiong A, Wang R, Yang L, Wang Z. Quality Evaluation of Traditional Chinese Medicine Compounds in Xiaoyan Lidan Tablets: Fingerprint and Quantitative Analysis Using UPLC-MS. Molecules. 2016 Jan 22;21(2):83. doi: 10.3390/molecules21020083. PubMed PMID: 26805803; PubMed Central PMCID: PMC6273587. 15: Pholphana N, Panomvana D, Rangkadilok N, Suriyo T, Ungtrakul T, Pongpun W, Thaeopattha S, Satayavivad J. A Simple and Sensitive LC-MS/MS Method for Determination of Four Major Active Diterpenoids from Andrographis paniculata in Human Plasma and Its Application to a Pilot Study. Planta Med. 2016 Jan;82(1-2):113-20. doi: 10.1055/s-0035-1558115. Epub 2015 Nov 17. Erratum in: Planta Med. 2016 Jan;82(1-02):E2. PubMed PMID: 26576030. 16: Garg A, Agrawal L, Misra RC, Sharma S, Ghosh S. Andrographis paniculata transcriptome provides molecular insights into tissue-specific accumulation of medicinal diterpenes. BMC Genomics. 2015 Sep 2;16:659. doi: 10.1186/s12864-015-1864-y. PubMed PMID: 26328761; PubMed Central PMCID: PMC4557604. 17: Xu FF, Fu SJ, Gu SP, Wang ZM, Wang ZZ, He X, Xiao W. Simultaneous determination of andrographolide, dehydroandrographolide and neoandrographolide in dog plasma by LC-MS/MS and its application to a dog pharmacokinetic study of Andrographis paniculata tablet. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 May 15;990:125-31. doi: 10.1016/j.jchromb.2015.03.014. Epub 2015 Mar 30. PubMed PMID: 25864014. 18: Huang JY, Liu XL, Zhou SP, Tong L, Ding L. [Research on UPLC-PDA fingerprint of andrographis paniculata and quantitative determination of 4 major constituents]. Zhongguo Zhong Yao Za Zhi. 2014 Nov;39(21):4240-5. Chinese. PubMed PMID: 25775801. 19: Koushik Kumar G, Prasanna G, Marimuthu T, Saraswathi NT. Structural basis for complementary and alternative medicine: Phytochemical interaction with non-structural protein 2 protease-a reverse engineering strategy. Chin J Integr Med. 2015 Jun;21(6):445-52. doi: 10.1007/s11655-014-1764-z. Epub 2014 Dec 9. PubMed PMID: 25491534. 20: Zhang HY, Xu XF, Huang Y, Wamg DQ, Deng QH. [Characteristic fingerprint analysis and determination of main components on Andrographis paniculata extract by UPLC]. Zhong Yao Cai. 2014 Jun;37(6):1055-8. Chinese. PubMed PMID: 25470974.