# Andrographolide
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> Markdown URL: https://mediated.wiki/source/Andrographolide.md
> Source: https://en.wikipedia.org/wiki/Andrographolide
> Source revision: 1344415202
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{cs1 config|name-list-style=vanc}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 419851636
| Name = Andrographolide
| ImageFile = Andrographolide.svg
| ImageClass = skin-invert-image
| ImageName = Andrographolide
| IUPACName = 3-[2-[Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-napthalenyl]ethylidene]dihydro-4-hydroxy-2(3''H'')-furanone
| OtherNames =
|Section1={{Chembox Identifiers
| SMILES = O=C3OCC(O)C3=CCC1\C(=C)CCC2C(C)(CO)C(O)CCC12C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16735664
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 65408
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 186141
| PubChem = 5318517
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 410105JHGR
| InChI = 1/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
| InChIKey = BOJKULTULYSRAS-UHFFFAOYAB
| InChI1 = 1/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
| InChIKey1 = BOJKULTULYSRAS-FNTFRYDEBY
| SMILES1 = OC3COC(=O)\C3=C\C[C@@H]1C(=C)CC[C@@H]2C(C)(CO)[C@H](O)CC[C@@]12C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BOJKULTULYSRAS-FNTFRYDESA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 5508-58-7
| RTECS =
}}
|Section2={{Chembox Properties
| C=20 | H=30 | O=5
| Appearance = Rhombic prisms or plates from ethanol or methanol
| Density = 1.2317 g/cm3
| Solubility = Sparingly soluble
| MeltingPtC = 230 to 231
| MeltingPt_notes =
| BoilingPt =
| pKa =
| pKb =
| Viscosity =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards =
| FlashPt =
}}
|Section8={{Chembox Related
| OtherFunction_label = [labdane](/source/labdane)s
| OtherFunction = [14-deoxyandrographolide](/source/14-deoxyandrographolide)
| OtherCompounds = [Xiyanping](/source/Xiyanping)
}}
}}
'''Andrographolide''' is a [labdane](/source/labdane) [diterpenoid](/source/diterpenoid) that has been isolated from the stem and leaves of ''[Andrographis paniculata](/source/Andrographis_paniculata)''.[{{cite journal | vauthors = Chakravarti RN, Chakravarti D | title = Andrographolide, the active constituent of Andrographis paniculata Nees; a preliminary communication | journal = The Indian Medical Gazette | volume = 86 | issue = 3 | pages = 96–7 | date = March 1951 | pmid = 14860885 | pmc = 5191793 }}] Andrographolide is an extremely bitter substance.
Andrographolide has been studied for its effects on [cell signaling](/source/cell_signaling), [immunomodulation](/source/Immunotherapy), and [stroke](/source/stroke).[[http://www.abcam.com/Andrographolide-ab120636.html abcamBiochemicals Andrographolide-ab120636]] Study has shown that andrographolide may bind to a spectrum of protein targets including [NF-κB](/source/NF-%CE%BAB) and [actin](/source/actin) by [covalent modification](/source/covalent_modification).[{{cite journal | vauthors = Wang J, Tan XF, Nguyen VS, Yang P, Zhou J, Gao M, Li Z, Lim TK, He Y, Ong CS, Lay Y, Zhang J, Zhu G, Lai SL, Ghosh D, Mok YK, Shen HM, Lin Q | display-authors = 6 | title = A quantitative chemical proteomics approach to profile the specific cellular targets of andrographolide, a promising anticancer agent that suppresses tumor metastasis | journal = Molecular & Cellular Proteomics | volume = 13 | issue = 3 | pages = 876–86 | date = March 2014 | pmid = 24445406 | pmc = 3945915 | doi = 10.1074/mcp.M113.029793 | doi-access = free }}][{{cite journal | vauthors = Tan WS, Liao W, Zhou S, Wong WS | title = Is there a future for andrographolide to be an anti-inflammatory drug? Deciphering its major mechanisms of action | journal = Biochemical Pharmacology | volume = 139 | pages = 71–81 | date = September 2017 | pmid = 28377280 | doi = 10.1016/j.bcp.2017.03.024 | s2cid = 26727535 }}]
Andrographolide is a non-ATP-competitive, substrate-competitive [GSK-3β](/source/GSK-3%CE%B2) inhibitor.[{{cite journal |url=https://www.professionalnutritionals.com/wp-content/uploads/2015/11/Andrographolide-Activates-the-Canonical-Wnt-Pathway.pdf |title=Andrographolide activates the canonical Wnt signalling pathway by a mechanism that implicates the non-ATP competitive inhibition of GSK-3β: autoregulation of GSK-3β in vivo | journal=Biochem J | date=1 March 2015 |volume=466 |issue=2 |pages=415–430 |doi=10.1042/BJ20140207 |pmc=|pmid=|author=Cheril Tapia-Rojas, Andreas Schüller, Carolina B. Lindsay, Roxana C. Ureta, Cristóbal Mejías-Reyes, Juan Hancke, Francisco Melo, Nibaldo C. Inestrosa}}][{{cite journal |url=https://onlinelibrary.wiley.com/doi/full/10.1111/cns.14885 |title=Natural compounds from herbs and nutraceuticals as glycogen synthase kinase-3β inhibitors in Alzheimer's disease treatment | journal=CNS Neuroscience & Therapeutics | date=11 August 2024 |volume=30 |issue=8 |pages= |doi=10.1111/cns.14885 |pmc=11317746|pmid=|author=Zheng Zhao, Ye Yuan, Shuang Li, Xiaofeng Wang, Xue Yang}}][{{cite journal |url=https://msptm.org/files/Vol39No3/tb-39-3-008-Hassan-W-R-M.pdf |title=Medicinal plants with antimalarial activities mediated via glycogen synthase kinase-3 beta (GSK3β) inhibition | journal=Trop Biomed | date=1 September 2022 |volume=39 |issue=3 |pages= 384-393 |doi=10.47665/tb.39.3.008 |pmc=|pmid=36214435|author=Hassan WRM, Ali AH, Basir R, Embi N, Sidek HM}}] When the [substrate](/source/Substrate_(chemistry)) concentration is 25μM, the [IC50](/source/IC50) of andrographolide for GSK-3β is 5.58±0.40μM. When the substrate concentration is increased to 90μM, the IC50 increases to 37.7μM.[
==Biosynthesis==
While andrographolide is a relatively simple [diterpene](/source/diterpene) [lactone](/source/lactone), the biosynthesis by Andrographis paniculata was determined in the 2010s.][{{cite journal | vauthors = Garg A, Agrawal L, Misra RC, Sharma S, Ghosh S | title = Andrographis paniculata transcriptome provides molecular insights into tissue-specific accumulation of medicinal diterpenes | journal = BMC Genomics | volume = 16 | issue = 1 | pages = 659 | date = September 2015 | pmid = 26328761 | pmc = 4557604 | doi = 10.1186/s12864-015-1864-y | doi-access = free }}][{{cite journal | vauthors = Sharma SN, Jha Z, Sinha RK, Geda AK | title = Jasmonate-induced biosynthesis of andrographolide in Andrographis paniculata | journal = Physiologia Plantarum | volume = 153 | issue = 2 | pages = 221–9 | date = February 2015 | pmid = 25104168 | doi = 10.1111/ppl.12252 }}] Andrographolide is a member of the [isoprenoid](/source/isoprenoid) family of [natural products](/source/natural_products). The precursors to isoprenoid biosynthesis, [isopentenyl pyrophosphate](/source/isopentenyl_pyrophosphate) (IPP) and [dimethylallyl pyrophosphate](/source/dimethylallyl_pyrophosphate) (DMAPP), can be synthesized through either the [mevalonic acid pathway](/source/mevalonic_acid_pathway) (MVA) or [deoxyxylulose pathway](/source/deoxyxylulose_pathway) (DXP).[{{cite journal | vauthors = Srivastava N, Akhila A | title = Biosynthesis of andrographolide in Andrographis paniculata | journal = Phytochemistry | volume = 71 | issue = 11–12 | pages = 1298–304 | date = August 2010 | pmid = 20557910 | doi = 10.1016/j.phytochem.2010.05.022 | bibcode = 2010PChem..71.1298S }}] Through selective C13 labeling of the precursors to both the MVA and DXP pathways, it was determined that the majority of the andrographolide precursors are synthesized through the DXP pathway.[ There are a small portion of andrographolide precursors synthesized through the MVA pathway. The biosynthesis of andrographolide begins with the addition of IPP to DMAPP, which forms [geranyl pyrophosphate](/source/geranyl_pyrophosphate). Another molecule of IPP is then added, yielding [farnesyl pyrophosphate](/source/farnesyl_pyrophosphate) (FPP). The final IPP molecule is added to the FPP to complete the backbone of the diterpene. The double bond originating from DMAPP is oxidized to an [epoxide](/source/epoxide) prior to the ring closing cascade that forms two six-membered rings. A series of oxidations form a five-membered lactone in addition to adding on the alcohol groups. The order of these post-synthetic modifications is not entirely known.][
thumb|center|Biosynthesis of andrographolide
== Research ==
In 2022, a research found that the combinatorial drug of [guaifenesin](/source/guaifenesin) and andrographolide has potential [anticonvulsant](/source/anticonvulsant) activity using network virtual screening. The possible [mechanism of action](/source/mechanism_of_action) is the two drugs synergistically affect [NMDA receptors](/source/NMDA_receptor).][{{cite journal|url=https://pubs.acs.org/doi/10.1021/acschemneuro.1c00774|title=Identification of Guaifenesin–Andrographolide as a Novel Combinatorial Drug Therapy for Epilepsy Using Network Virtual Screening and Experimental Validation|doi=10.1021/acschemneuro.1c00774|volume=13|issue=7|date=2022-03-25|journal=ACS Chemical Neuroscience|author=Yunyuan Huang, Haiyan Xu, Pei Wang, Rurong Gu, Xiaokang Li, Yixiang Xu, Jiqun Wang, Sicong Qiao, Donglei Shi, Zhaobing Gao, Jian Li|url-access=subscription}}]
== See also ==
* [Xiyanping](/source/Xiyanping) [WINDOSE-Tablet](/source/WINDOSE-Tablet)
== References ==
{{reflist|30em}}
Category:Bitter compounds
Category:Diterpenes
Category:Furanones
Category:Hydroxymethyl compounds
Category:Secondary alcohols
Category:Decalins
Category:Triols
Category:Tetrahydrofurans
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Adapted from the Wikipedia article [Andrographolide](https://en.wikipedia.org/wiki/Andrographolide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Andrographolide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.