Andrographolide

Andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata.[1] Andrographolide is an extremely bitter substance.

Andrographolide
Andrographolide
Names
IUPAC name
3-[2-[Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-napthalenyl]ethylidene]dihydro-4-hydroxy-2(3H)-furanone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.024.411
UNII
  • 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 checkY
    Key: BOJKULTULYSRAS-FNTFRYDESA-N checkY
  • 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
    Key: BOJKULTULYSRAS-UHFFFAOYAB
  • 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/b13-5+/t14-,15?,16+,17-,19+,20?/m1/s1
    Key: BOJKULTULYSRAS-FNTFRYDEBY
  • O=C3OCC(O)C3=CCC1\C(=C)CCC2C(C)(CO)C(O)CCC12C
  • OC3COC(=O)\C3=C\C[C@@H]1C(=C)CC[C@@H]2C(C)(CO)[C@H](O)CC[C@@]12C
Properties
C20H30O5
Molar mass 350.455 g·mol−1
Appearance Rhombic prisms or plates from ethanol or methanol
Density 1.2317 g/cm3
Melting point 230 to 231 °C (446 to 448 °F; 503 to 504 K)
Sparingly soluble
Related compounds
Related labdanes
 14-deoxyandrographolide
Related compounds
 Xiyanping
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Andrographolide has been studied for its effects on cell signaling, immunomodulation, and stroke.[2] Study has shown that andrographolide may bind to a spectrum of protein targets including NF-κB and actin by covalent modification.[3][4]

Biosynthesis

While andrographolide is a relatively simple diterpene lactone, the biosynthesis by Andrographis paniculata was determined in the 2010s.[5][6] Andrographolide is a member of the isoprenoid family of natural products. The precursors to isoprenoid biosynthesis, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), can be synthesized through either the mevalonic acid pathway (MVA) or deoxyxylulose pathway (DXP).[7] 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.[7] 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. Another molecule of IPP is then added, yielding 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 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.[7]

Biosynthesis of andrographolide

See also

References
  1. Chakravarti RN, Chakravarti D (March 1951). "Andrographolide, the active constituent of Andrographis paniculata Nees; a preliminary communication". The Indian Medical Gazette. 86 (3): 96–7. PMC 5191793. PMID 14860885.
  2. abcamBiochemicals Andrographolide-ab120636
  3. Wang J, Tan XF, Nguyen VS, Yang P, Zhou J, Gao M, et al. (March 2014). "A quantitative chemical proteomics approach to profile the specific cellular targets of andrographolide, a promising anticancer agent that suppresses tumor metastasis". Molecular & Cellular Proteomics. 13 (3): 876–86. doi:10.1074/mcp.M113.029793. PMC 3945915. PMID 24445406.
  4. Tan WS, Liao W, Zhou S, Wong WS (September 2017). "Is there a future for andrographolide to be an anti-inflammatory drug? Deciphering its major mechanisms of action". Biochemical Pharmacology. 139: 71–81. doi:10.1016/j.bcp.2017.03.024. PMID 28377280. S2CID 26727535.
  5. Garg A, Agrawal L, Misra RC, Sharma S, Ghosh S (September 2015). "Andrographis paniculata transcriptome provides molecular insights into tissue-specific accumulation of medicinal diterpenes". BMC Genomics. 16 (1): 659. doi:10.1186/s12864-015-1864-y. PMC 4557604. PMID 26328761.
  6. Sharma SN, Jha Z, Sinha RK, Geda AK (February 2015). "Jasmonate-induced biosynthesis of andrographolide in Andrographis paniculata". Physiologia Plantarum. 153 (2): 221–9. doi:10.1111/ppl.12252. PMID 25104168.
  7. Srivastava N, Akhila A (August 2010). "Biosynthesis of andrographolide in Andrographis paniculata". Phytochemistry. 71 (11–12): 1298–304. doi:10.1016/j.phytochem.2010.05.022. PMID 20557910.
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