CHEMICAL CONSTITUENTS OF ANDROGRAPHIS PANICULATA (BURM.F) NEES: A REVIEW
HTML Full TextCHEMICAL CONSTITUENTS OF ANDROGRAPHIS PANICULATA (BURM.F) NEES: A REVIEW
Anju Bhatnagar
Department of Chemistry, D. B. S. (PG) College, Dehradun, Uttarakhand, India.
ABSTRACT: Andrographis paniculata Nees is a valuable medicinal herb of Acanthaceae family, is used for centuries to treat several diseases including viral hepatitis, cirrhosis, malaria and diabetes. This medicinal plant has hepato-protective, immunological, anti-bacterial, anti-inflammatory, anti-oxidant and antithrombotic qualities. It has many important bioactive compounds such as diterpenoids, flavonoids and polyphenols. Diterpenoids, including andrographolide, neoandro-grapholide and dehydroandrographolide are the main determinants of Andrographis paniculata quality. The most common and abundant form is andrographolide. Numerous human ailments are treated and prevented by it. Due to its various therapeutic applications, it is widely cultivated in many parts of the world and its relevance as a medicinal plant is constantly increasing. A comprehensive bibliographic search was conducted using offline and Online Databases. The current review aims to offer an updated and thorough analysis of the chemical components, explore their pharmacological potential and lay the basis for further research.
Keywords: Chemical constitutents, Diterpenoids, Flavonoids, Polyphenols, Biological activity hepato-protective, Andrographolide
INTRODUCTION: From ancient times, medicinal plants have been used to treat various ailments and disorders. Worldwide, around 80,000 plant species have been recognized and utilized as medicines. In India, 7500 medicinal plants have been recognized for therapeutic use for curing different diseases 1, 2. Natural ingredients derived from medicinal plants, used as sources of drug. In spite of tremendous development of synthetic drugs and antibiotics during the 20th century, plant still constitute one of the major sources of drugs in the modern and traditional system of medicine throughout the world.
The largely rural population relies on medicinal plants as a source of treatments or to meet their healthcare needs for several reasons, including accessibility, affordability, and low cost 3, 4. It is advantageous to the nature of healthy human life 5, 6. Andrographis paniculata , often referred to as Kalmegh, is commonly used as traditional medicine in Asian countries to treat various diseases such as upper respiratory infections, fever, herpes, sore throats, and several chronic ailments 7.
The plant is widely used in Indian traditional medicine, including Ayurveda, Unani, and Siddha, as a home cure for many illnesses. It has many bioactive compounds like diterpenoids, lactones, diterpenes glycosides, flavonoids, and flavonoid glycosides 8. A significant chemical andrographolide is a diterpenoid lactone having several pharmacological properties 9-10. The amount of andrographolide is highest in the leaves (2.39 %) and lowest in the seeds of Andrographis 11. It cures and prevents several diseases such as cold, fever and colic pain, and it is active against inflammatory 12, antidiabetic activity 13, antioxidant 14, antifertility 15, cardiovascular 16, hepatoprotective 17, anti-cancer properties 36-38 and anti-virus including inhibited HIV 39. This study provides the most current information about phytochemical components, pharmacological potentials and research needs relevant to Andrographis paniculata.
About the Genus Andrographis: Genus Andrographis includes 28 species of small herbs basically dispensed in tropical and subtropical Asia as well as some other countries such as Malaysia, Indonesia, Vietnam, Sri Lanka, Laos, Cambodia, Pakistan, Myanmar and the Caribbean islands. Some species, such as Andrographis paniculata, are recognized to have healing properties 18. It belongs to the Acanthaceae family, a potent herb utilized for the number of Ayurvedic, Siddha and homoeopathic formulations.
Andrographis paniculata is commonly used in indigenous medicine, especially as a bitter tonic, to treat fevers, diarrhoea and to get rid of intestinal worms. The herb is utilized as a liver tonic, blood purifier, and stomachic 19.
The annual herb Andrographis paniculata are found in different habitats including forests, plains, hill area and wetlands. It abundantly grows up to 1 m height with dark green slender stem, glabrous leaves in lanceolate arranged and tiny, hairy, white to pink small flowers. It is very abundant in South East Asia, India and Sri Lanka. Especially, In India, Andrographis paniculata are found in southern part such Karnataka, Andhra Pradesh, Tamil Nadu, Uttar Pradesh, and Madhya Pradesh. The plant's leaves and other parts, including the root, have been used medicinally 20. It is grown as a kharif (rainy season) crop in India. Heat and humidity with lots of sunshine are the ideal climate conditions for the plant Fig. 1.
FIG. 1: AERIAL PARTS OF ANDROGRAPHIS PANICULATA PLANT
Bioactive Constituents of Andrographis paniculata: All parts of this plant are used to extract the active photochemical. Active components mainly isolated from ethanol or methanol extract of leaves, stems, roots, and whole plant of Andrographis paniculata, which include diterpenes, lactones, flavonoids, and xanthones 21-23. But the compositions of phytoconstituents widely differ from one part to another. Flavonoids are mostly found in the roots of plants 24-25. Alkanes, ketones and aldehydes are also present in the aerial components.
Chemistry of Andrographolide: In 1896, Boorsma first isolated Andrographolide from Andrographis paniculata and Gorter identified it as a lactone in 1911. It has a bitter taste and is a light yellow or colourless crystal compound. The chemical name of andrographolide is 3-[2-[decahydro – 6 – hydroxyl – 5 - (hydroxymethyl) -5, 8a – dimethyl – 2 - methylene-1-napthalenyl] ethylidene] dihydro- 4-hydroxy-2(3H)-furanone Fig. 2(1). Its molecular formula is C20H30O5 and molecular mass 350.4 (C= 68.5%, H= 8.6%, O = 22.8%) is the major phyto-constituent mainly concentrated in leaves of Andrographis paniculata plant. It is insoluble in water but soluble in acetone, ether, chloroform and hot ethanol. Crystalline Andrographolide is highly stable even at 70°C for three months, its UV absorption maxima in methanol or ethanol at 222-224 nm.
In this review, we described the information of 47 main bioactive constituents isolated from Andrographis paniculata and extraction mode with the plant part listed in Table 1.
TABLE 1: BIOACTIVE COMPOUNDS OF ANDROGRAPHIS PANICULATA
Chemical constituents (chemical structure No.) | Plant sources/ solvent of extraction | Bio-activity/References |
Ent-labdane diterpenoids | ||
Andrographolides (1)
|
Whole plant/
Methanol, Ethanol, Hexane, Acetone water,
|
Anti-inflammatory 26-27, Hepatoprotective 28-29, Anti diabetic 30-32, Anti-influenza 33, Anticancer 34-37, Anti retroviral 38-39, Analgesic,antipyretic 40, Anti angiogenic 41, Cardio protective 42, Cholestatic 43, |
14-Deoxyandrographolide (2) | Leaves, whole plant &Aerial parts / Hexane, Acetone water ethanol | Hepatoprotective 44, Anti fungal 45, Anti bacterial 46, Immunomodulator 47, Antihypertensive 48-49. |
Neoandrographolide:(3) | Leaves , whole plant and Aerial parts /
Methanol, Ethanol, Acetone water |
Anti-inflammatory 50-51, Antioxidant 52, Antiparasitic 53, Antiherpes-simplex virus 38 , Hepatoprotective 54,
Chemosensitiser 55, |
14-Deoxy 11,12-didehydro andrographolide (4) | Leaves, whole plant, and Aerial parts / Ethanol, Hexane, Dichloromethane | Antiretroviral 39,Cholestatic 43, Antioxidant 52, Antifungal 45, Antihypertensive 48, Antidiabetic 56, Hepatoprotective 57, Cytotoxic 58, Antiherpes 38, |
Andrographiside (5) | Whole plant, roots /Methanol, petroleum ether & chloroform | Hepatoprotective 44, |
Isoandrographolide (6) | Leaves, Aerial parts, whole plant & roots /Methanol, Ethanol, Hexane | Anti- cancer and Anti inflammatory 38, Antiproliferative 59, Anti bacterial 60, Cytotoxic 37 , Cell differentiation inducer 60 |
Andrograpanin (7) | Leaves , and Aerial parts Ethanol and Hexane | Anti-inflammatory 61 |
14-Deoxy-11-oxo-andrographolide (8) | Aerial parts /Ethanol and water-Acetone | Anti leishmaniasis 62 |
14-Deoxy-11-hydroxy-
andrographolide(9) |
Aerial parts / Ethanol | Cell differentiation inducer 60 |
15-Methoxy-3,19-dihydroxy 8(17)11,13-entlabda-trien-16,15-olide (10) | Aerial parts /
Ethanol |
Anti proliferative 59 |
8(17),13-Ent-labda-diene-15,16,19-triol (11) | Aerial parts /
Ethanol |
Anti proliferative 59 |
3-O- 𝛽-D-glucosyl-14-deoxyandrographolide (12) | Whole plant/
Methanol and Ethanol |
Anti bacterial 44, Antifungal 45 |
14-Deoxy-12-hydroxyandrographolide(13) | Whole plant/
Methanol |
Anti microbial 46 |
6’-Acetyl-neo-andrographolide (14) | Aerial parts /Methanol | Cell differentiation inducer 60 |
3,14-Dideoxyandrographolide (15) | Aerial parts /Ethanol | Anti proliferative 59, |
3-Oxo-14-deoxyandrographolide (16) | Aerial parts /Ethanol | Antiproliferative 59 |
3-O- 𝛽 -D-glucopyranosyl 14,19-dideoxy andrographolide (17) | Aerial parts / water Acetone
|
Antimicrobial 46
|
3-O- 𝛽 -D-glucopyranosyl andrographolide (18) | ||
Andrographolactone (19) | Aerial parts /Ethanol | Cytotoxic 37 |
8,17-Epoxy-14 deoxyandrographolide(20) | Leaves /
Acetone water |
Anti microbial 46 |
14-Deoxy-17-betahydroxyandrographolide (21) | Leaves / water,
Acetone |
Antimicrobial 46 |
12-Hydroxyandrographolide (22) | Aerial parts /Ethanol | Antiproliferative 59 |
3-Oxo-14-deoxy-11,12 didehydroandrographolide (23) | Leaves /Ethanol | Antiproliferative 59 |
Bis-andrographolide A (24) | Aerial parts /Methanol | Cell differentiation inducer 60, analgesic, anti-inflammatory 70, |
7-Hydroxy-14-deoxyandrographolide (25) | Leaves /Ethanol | Antiproliferative 59, |
19-O-[beta-D-apiofuranosyl-beta Dglucopyranoyl]-3,14- dideoxyandrographolide (26) | Leaves /Acetone, water | Antimicrobial 46 |
Andrographalide-B (47) | Aerial parts/Ethanol | Antiviral 21 |
Flavonoids | ||
Apigenin (27) | Whole plant parts / Methanol | Antiplatelet aggregator 66, 64
|
7-O-methylwogonin (28) | Whole plant parts / Methanol , hexane | |
Onysilin (29) | Whole plant parts / Methanol | |
7,8-Dimethoxy-2-D-glucopyranosyl oxyflavone (30) | Leaves / Ethanol
|
Anti proliferative 63, 59 |
7-O-methyl-dihydrowogonin (31) | ||
Skullcapavone-1,2’methoxylether (32) | ||
5,4’-Dihydroxy-7-methoxy-8- O--D-glucopyranosyloxy flavone (33) | ||
5,7,8-Trimethoxydihydroflavone (34) | ||
7,8-dimethoxy 2 hydroxy-5-O- 𝛽 –dglucopyranosyloxyflavone , (35) | ||
Andrographidine A, (36) | ||
Andrographidine C, (37) | ||
Luteolin, (38) | ||
7,8,2’,5’-Tetramethoxy 5-O- 𝛽 -D-glucopyranosyloxyflavone, (39) | ||
5,4’-Dihydroxy-7-O- 𝛽 -D pyranglycuronate butyl ester, (40) | ||
5,4'-Dihydroxy-7-methoxy-8- 𝛽 -D-glucopyranosyloxyflavone (41) | ||
Xanthones | ||
1,2-dihydroxy-6,8-dimethoxy-xanthone (42) | Roots / Petroleum Ether , Methanol, CHCl3 and water | Antimalarial 65
|
1,8-dihydroxy-2,6-dimethoxyxanthen-9-one (43) | ||
8-hydroxy-1,2,6-trimethoxyxanthen-9-one (44) | ||
4,8-dihydroxy-2,7-di-methoxy-xanthene-9-one (45) | ||
3,4-Dicaffeoylquinic acid (46) | Whole Plant parts /Methanol | Anti platelet aggregator 66 |
Fig. 2: Chemical Structures of Bioactive Constituents of Andrographis paniculata
Flavonoids | |||||||||||||||
Xanthones | |||||||||||||||
Pharmacological Properties: Andrographis paniculata crude extracts and its isolated chemical constituents show a numerous medicinal activities 67-68.
It includes antioxidant activity 69, anti-bacterial 46 and anti-microbial activities 47, anti-malarial, cold and fever, anti-venom activity, anti-diarrhoeal activity, anticancer activity 70, urinary tract infection and antidiabetic activity, cardiovascular activity, immunomodulatory activity etc.
CONCLUSION: The primary bioactive constituents in the herb are flavonoids, diterpenoids and polyphenols. Extensive literature review and experimental data analysis suggest that Andrographis paniculata are traditionally used for treating fever and several infections. The plant improves the activities of the heart and liver by treating cardiovascular illness and preventing liver damage. According to reports, andrographis reduces fertility in both male and female animals as well as people. In addition, it has enormous benefits for the functioning of the brain and central nervous system, allergic reactions and respiratory problems. Due to its enormous medicinal potential, Andrographis paniculata demand has significantly surged in recent years.
Numerous clinical trials were conducted successfully and without any negative effects, proving that the plant is a valuable and safe medical resource for people. Cultivation could be an excellent solution to make Andrographis paniculata available for research in order to satisfy commercial demand. More research is still required to learn more about the novel bioactive compounds and improve the bioactivity of the original chemicals.
ACKNOWLEDGMENTS: I appreciate my institution's head giving me all the assistance to complete this review. I also express my gratitude to my friends, who have supported and inspired me throughout the investigation.
Funding: This research received no external funding.
CONFLICTS OF INTEREST: The authors declare no conflict of interest.
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How to cite this article:
Bhatnagar A: Chemical constituents of Andrographis paniculata (Burm. F) Nees: a review. Int J Pharm Sci & Res 2023; 14(7):3238-45. doi: 10.13040/IJPSR.0975-8232.14(7).3238-45.
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