27215-14-1

Basic information

• Product Name: Neoandrographolide
• Synonyms: 3-[2-[(4as,5r,8as)-5,8a-dimethyl-2-methylidene-5-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]ethyl]-5h-furan-2-one;ANDROGRAPHOLIDE, NEO-;NEOANDROGRAPHOLIDE;ANDROGRAPHOLIDE, NEO(P);2(5H)-Furanone, 3-[2-[(1R,4aS,5R,8aS)-5-[(β-D-glucopyranosyloxy)methyl]decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-;3-[2-[(1R,4aS,5R,8aS)-5-[(β-D-Glucopyranosyloxy)methyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,8a-dimethyl-2-methylenenaphthalene-1-yl]ethyl]-2(5H)-furanone;3-[2-[(1R,4aβ)-5α-[(β-D-Glucopyranosyloxy)methyl]decahydro-5,8aα-dimethyl-2-methylenenaphthalen-1α-yl]ethyl]furan-2(5H)-one;4-[2-[(4aS,5R,8aS)-5,8a-dimethyl-2-methylene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]decalin-1-yl]ethyl]-2H-furan-5-one
• CAS NO: 27215-14-1
• Molecular Formula: C₂₆H₄₀O₈
• Molecular Weight: 480.59
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 27215-14-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 167～168℃
• Boiling Point: 668.1 °C at 760 mmHg
• Flash Point: 220.1 °C
• Appearance: Colorless columnar crystal
• Density: 1.27 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.93±0.70(Predicted)
• CAS DataBase Reference: Neoandrographolide(CAS DataBase Reference)
• NIST Chemistry Reference: Neoandrographolide(27215-14-1)
• EPA Substance Registry System: Neoandrographolide(27215-14-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 27215-14-1(Hazardous Substances Data)

Usage

Description

Neoandrographolide is a colorless column crystal diterpenoid compound isolated from the stem and leaves of Andrographis paniculata, a well-recognized medicinal plant in Asia. It is characterized by a melting point of 167-168°C and specific optical rotation values of -48° (pyridine) and -45° (c=1, absolute ethanol). The compound is soluble in methanol, ethanol, acetone, and pyridine, slightly soluble in chloroform and water, but insoluble in ether and petroleum ether.

Uses

Used in Pharmaceutical Industry:
Neoandrographolide is used as an active pharmaceutical ingredient for its anti-inflammatory and antimicrobial activities. It is derived from Andrographis paniculata, a medicinal plant with a history of treating various ailments such as colds, sore throat, mouth sores, cough, and diarrhea dysentery.
Used in Traditional Medicine:
Neoandrographolide is used as a key component in traditional medicine practices, particularly in South and Southeast Asia, India, and Australia. The plant Andrographis paniculata, from which it is derived, has been utilized for its therapeutic properties and is also cultivated in various provinces in China.
Used in Research and Development:
Neoandrographolide serves as a valuable compound in the research and development of new drugs and therapies, given its anti-inflammatory and antimicrobial properties. It contributes to the ongoing efforts to discover and develop novel treatments for various health conditions.
Used in US Pharmacopeia:
Neoandrographolide is recognized and included in the US Pharmacopeia, indicating its significance and potential applications in the field of medicine and pharmaceuticals.

History

The chemical constituents of Andrographis paniculata are mainly lactones and flavonoids, including the lactone compounds such as andrographolide and dehydrated andrographolide. In 1952, Kleipool first reported the separation of andrographolide from Andrographis paniculata . In 1968 and 1971, W.?R. Chan et?al. identified the chemical structure and stereostructure of andrographolide. In the 1990s, a variety of diterpene lactones were isolated from the aerial part and the lotus leaf of Andrographis paniculata, such as andrographolide, neoandrographolide, dehydroandrographolide, deoxyandrographolid, deoxyandrographiside, 8-methylandrograpanin, 3-dehydrodeoxyandrographolide, andrograpanin, and 3-oxo-14-deoxy-andrographol,and also some flavonoids and sitosterol and daucosterol compounds . Until now, more than 40 diterpene lactone components and more than 70 flavonoids have been found from Andrographis paniculata. There are sterols, organic acids, diterpene alcohols, diterpene acid salts, and cycloalkene ether also found from Andrographis paniculata .Since the 1970s, pharmacists and organic chemists have done a lot of work on the modification of andrographolide, mainly in Michael addition of α, β-unsaturated lactone double bonds and three hydroxyl groups selective esterification, oxidation and substitution reactions, redox reduction of double bonds, intramolecular cyclization, and lactone ring replacement reactions , and the resulting andrographolide derivatives or analogues can improve the antibacterial, anti-inflammatory, cardiovascular system, immunomodulation, and antitumor activities.

Indications

Neoandrographolide is available in the Pharmacopoeia of the People’s Republic of China (1977).Neoandrographolide and andrographolide are the main active ingredients of a variety of pharmaceutical preparations containing the Andrographis herb, such as andrographolide capsules, andrographolide tablets, Andrographis injection, potassium dehydroandrographolide succinate injection, Andrographis tablets, Xiaoyan Lidan tablets, and Fufang chuan xin lian tablets. These drugs are mainly used for treating acute bacterial dysentery, acute gastroenteritis, upper respiratory tract infection, acute tonsillitis, pharyngitis, etc. In addition, they are also used to treat malignant hydatidiform mole and choriocarcinoma.

Pharmacology

Andrographis paniculata has detoxifying abilities, reduces swelling, and relieves pain. The four major diterpene lactones in Andrographis paniculata have antipyretic and anti-inflammatory activities against 2,4-dinitrophenol or endotoxin-induced fever and egg white-induced edema or croton oil-induced inflammatory models.Animal experiments have shown that Andrographis paniculata has inhibited and delayed the body temperature elevation of persons with infections caused by pneumococcus and hemolytic streptococcus. It also can be used for treating cough and asthma and especially for treating acute bacterial dysentery, acute gastroenteritis, upper respiratory tract infection, acute tonsillitis, pharyngitis, and so on.The active ingredients andrographolide and neoandrographolide inhibit lipopolysaccharide-induced NO production in the mouse peritoneal macrophages . Neoandrographolide at the high concentration can inhibit the macrophage outbreak caused by LPS and the proliferation of lymphocytes and can synergistically enhance the PMA stimulating effect on the respiratory outbreak. The possible mechanism is related to its ROS scavenging activity .

Clinical Use

Neoandrographolide is one of the main active ingredients of the natural plant Andrographis paniculata. But there is no formulation of neoandrographolide. Andrographis injection has been clinically used, but it has several side effects.

InChI:InChI=1/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

Upstream product

• 133-89-1 UDP-glucose 
• 82209-74-3 19-hydroxy-8(17),13-ent-labdadien-15->16 lactone 

Downstream Products

• 92587-12-7 19-acetoxy-8(17),13-ent-labdadien-15->16 lactone 
• 21681-03-8 neoandrographolide isoaglucone 
• 82209-74-3 19-hydroxy-8(17),13-ent-labdadien-15->16 lactone 

Relevant articles and documents

Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis

ApUGT, a diterpene glycosyltransferase from Andrographis paniculata, could transfer a glucose to the C-19 hydroxyl moiety of andrograpanin to form neoandrographolide. This glycosyltransferase has a broad substrate scope, and it can glycosylate 26 natural and unnatural compounds of different structural types. This study provides a basis for exploring the glycosylation mechanism of ent-labdane-type diterpenes and plays an important role in diversifying the structures used in drug discovery.