Available from stock

Andrographolide

SKU: A0576

Category: Phytochemicals

Synonyms: Andrographis; 5508-58-7
CAS-Number: C₂₀H₃₀O₅
Molecular Formula: 350.455
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98% (HPLC)
Appearance: White to light yellow powder
Identity: 1H-NMR

Properties

Solvents: chloroform, DMF (15 mg/ml), DMSO (2 mg/ml)
Melting Point: 229-232 °C (lit.)
Optical Activity: [α]20/D -126°, c = 1.5 in acetic acid

Shipping: AMBIENT
Short Term Storage: -20°C
Long Term Storage: -20°C
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.

Hazard statements: H315, H319, H335
Precautionary statements: P264, P280, P261, P362+364
GHS Symbol: GHS07
Signal word: Warning
Transportation: Not dangerous goods

Description: Andrographolide, a bioactive diterpene lactone, is the main constituent of Andrographis paniculata, a plant used in traditional medicines. It is known to have different biological properties such as anti-inflammatory, immunosuppressive, antidiabetic, antihyperglycemic, antibacterial, antioxidant, antinoniceptive, antimalarial, anticancer and hepatoprotective activity. It also shows potent anti-viral effect against dengue virus. It blocks T-cell proliferation and the proliferation of several cancer cell lines in vitro. It acts as an irreversible antagonist of NF-?B and AP-1 (IC50 ≤ 15 µM) activation, and prevents in vitro and in vivo T cell activation.
Smiles: C=C1CC[C@@]([C@@](CO)(C)[C@H](O)CC2)([H])[C@]2(C)[C@@H]1C/C=C3C(OC[C@H]/3O)=O
InChi Key: BOJKULTULYSRAS-OTESTREVSA-N
References: (1) P.K. Visen, et al., J. Ethnopharmacol. 40, 131 (1993) , (2) W.F. Chiou, et al., Br. J. Pharmacol. 129, 1553 (2000) , (3) B.C. Yu, et al., Planta Med. 69, 1075 (2003) , (4) Y.F. Xia, et al., J. Immunol. 173, 4207 (2004) , (5) J.H. Chen, et al., Biochem. Pharmacol. 67, 1337 (2004) , (6) R.A. Burgos, et al., Planta Med. 71, 429 (2005) , (7) M.I. Iruretagoyena, et al., J. Pharmacol. Exp. Ther. 312, 366 (2005) , (8) C. Liu, et al., Genes Cancer 2, 151 (2011) , (9) J.C. Lim, et al., Clin. Exp. Pharmacol. Physiol. 39, 300 (2012) (Review) , (10) S.K. Mishra, et al., Front. Biosci. 7, 255 (2015) (Review) , (11) V. Kishore, et al., Curr. Top. Med. Chem. 17, 845 (2017) (Review) , (12) S. Gupta, et al., Arch. Virol. 162, 611 (2017) (Review) , (13) W.S.D. Tan, et al., Biochem. Pharmacol. 139, 71 (2017) (Review) , (14) C.H. Yang, et al., Int. J. Mol. Sci. 18, E1638 (2017) (Review) , (15) M.T. Islam, Front. Pharmacol. 8, 571 (2017) (Review) , (16) J. Lu, et al., Biomed. Pharmacother. 117, 109078 (2019) (Review) , (17) L. Zhang, et al., Pharmacology (Epub ahead of print) (2019) (Review) , (18) E. Mussard, et al., Antioxidants 8, E571 (2019) (Review)
InChi: 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

Andrographolide, a bioactive diterpene lactone, is the main constituent of Andrographis paniculata, a plant used in traditional medicines. It is known to have different biological properties such as anti-inflammatory, immunosuppressive, antidiabetic, antihyperglycemic, antibacterial, antioxidant, antinoniceptive, antimalarial, anticancer and hepatoprotective activity. It also shows potent anti-viral effect against dengue virus. It blocks T-cell proliferation and the proliferation of several cancer cell lines in vitro. It acts as an irreversible antagonist of NF-?B and AP-1 (IC50 ≤ 15 µM) activation, and prevents in vitro and in vivo T cell activation.

SKU: A0576 Category: Phytochemicals

Additional information

Additional information

Synonyms	Andrographis
Purity	≥98% (HPLC)
Appearance	White to light yellow powder
CAS-Number	5508-58-7
Molecular Formula	C20H30O5
Molecular Weight	350.455
Identity	1H-NMR
Solvents	chloroform, DMF (15 mg/ml), DMSO (2 mg/ml)
Melting Point	229-232 °C (lit.)
Optical Activity	[α]20/D -126°, c = 1.5 in acetic acid
Smiles	C=C1CC[C@@]([C@@](CO)(C)[C@H](O)CC2)([H])[C@]2(C)[C@@H]1C/C=C3C(OC[C@H]/3O)=O
InChi Key	BOJKULTULYSRAS-OTESTREVSA-N
Shipping	AMBIENT
Short Term Storage	-20°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H315, H319, H335
Precautionary statements	P264, P280, P261, P362+364
GHS Symbol	GHS07
Signal word	Warning
Transportation	Not dangerous goods
References	(1) P.K. Visen, et al., J. Ethnopharmacol. 40, 131 (1993), (2) W.F. Chiou, et al., Br. J. Pharmacol. 129, 1553 (2000), (3) B.C. Yu, et al., Planta Med. 69, 1075 (2003), (4) Y.F. Xia, et al., J. Immunol. 173, 4207 (2004), (5) J.H. Chen, et al., Biochem. Pharmacol. 67, 1337 (2004), (6) R.A. Burgos, et al., Planta Med. 71, 429 (2005), (7) M.I. Iruretagoyena, et al., J. Pharmacol. Exp. Ther. 312, 366 (2005), (8) C. Liu, et al., Genes Cancer 2, 151 (2011), (9) J.C. Lim, et al., Clin. Exp. Pharmacol. Physiol. 39, 300 (2012) (Review), (10) S.K. Mishra, et al., Front. Biosci. 7, 255 (2015) (Review), (11) V. Kishore, et al., Curr. Top. Med. Chem. 17, 845 (2017) (Review), (12) S. Gupta, et al., Arch. Virol. 162, 611 (2017) (Review), (13) W.S.D. Tan, et al., Biochem. Pharmacol. 139, 71 (2017) (Review), (14) C.H. Yang, et al., Int. J. Mol. Sci. 18, E1638 (2017) (Review), (15) M.T. Islam, Front. Pharmacol. 8, 571 (2017) (Review), (16) J. Lu, et al., Biomed. Pharmacother. 117, 109078 (2019) (Review), (17) L. Zhang, et al., Pharmacology (Epub ahead of print) (2019) (Review), (18) E. Mussard, et al., Antioxidants 8, E571 (2019) (Review)
InChi	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
Quantity	500 mg, Bulk