Eclipta, Han Lian Cao;
Nature's Remedy for Liver and Kindey Dysfunction

By: Elissa H. Williams

Eclipta, Han Lian Cao. D.L. Nofziger, Copyright 2003. Permission Requested.
http://www.weedscience.okstate.edu/Weeds/PEETWeeds.htm

Table of Contents:

Introduction to Eclipta, Han Lian Cao


Eclipta prostrata Linn, more commonly referred to as Han Lian Cao, is a flowering plant that is native to the United States. Eclipta is not only found in over forty U.S. states, it is also found in tropical areas worldwide. The Eclipta plant is approximately 50 centimeters tall and from a single stem protruding from the ground, it branches into several more stems [1]. The stems can contain little white flowers that look very similar to daisys. For this reason, the Eclipta plant has an alternative name of the "Fake Daisy". Oddly, Eclipta seeds not only sprout in the ground but also the seeds can sprout in water.


Eclipta, D. Tenaglia, Copyright 2007. Permission Requested. http://www.missouriplants.com/Whiteopp/White_flowers_opposite_page2.html


Eclipta, Han Lian Cao, is used primarily for the "treatment of liver damage due to cirrhosis, infective hepatitis, and hepatic enlargement" [2]. The plant is also known to treat dysfunction of the kidneys, spleen, and gall bladder. The chemical compounds which give Eclipta its medicinal value are Wedelolactone and Demethylwedlolactone.

Scientific studies have been conducted in which rats were treated with phalloidin or carbon tetrachloride. The rats were then given Eclipta plant extracts and the mortality rates of the rats were obtained. 70% of the rats that were not given Eclipta extracts died, whereas all 100% of the rats that were given the eclipta extract remained alive. Researchers later concluded that the Eclipta extract, more specifically the Wedelolactone contained within the extract, could regulate the levels of liver drug-metabolizing enzymes [3].

Eclipta Biology

The common names of the Eclipta plant include: Eclipta, Han Lian Cao, Bhringraj, Keshraj, Yerba de Tajo and False Daisy. The botonical name of the Eclipta plant is Eclipta prostrata (L.) L.. There are two subspecies of the Eclipta plant which fall below Eclipta prostrata (L.) L. and include: Eclipta alba (L.) Hassk. and Eclipta erecta L..

The Eclipta plant is found all over the world in primarily warm temperate climates. The Eclipta plant can grow in a variety of soil types; sand, dirt, and clay, and "the soil pH can range from about 5.2 to 7.9" [4]. The soil must be moist or wet providing the plant with a fairly constant source of water. The plant also prefers a shaded environment. Since the Eclipta plant is an annual, its active growth rate occurs during the summer each year. It is at this time that the little flowers of the Eclipta plant also bloom. The Eclipta plant has a maximum mature height at 3 foot 2 inches and grows vertically into a "bunch"[4]. The Ecplita plant is endangered in the state of New York [5].


Eclipta Distribution in the United States. Regions in which the Eclipta plant is found is shaded in green.

USDA. Copyright 2007. Permission Requested.
http://plants.usda.gov/java/profile?symbol=ECPR

Pharmacological Effects of Eclipta

The Eclipta plant has numerous pharmcological effects depending upon which part of the plant is used medicinally. The stems and roots of the Eclipta plant have antihepatotoxic acitivty. Therefore, the Eclipta plant can protect the liver from damaging toxins. The stems and roots can also be administired to promote bile flow and increased kidney function. The leaves of the Eclipta plant, when dried, have analgesic activity." The leaves demonstrate antibacterial activity against pathogenic bacteria including Bacillus subtillis, Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus" [6]. A paste can be prepared from griding the leaves and stems of the plant which can be used as an anti-inflammatory agent in treating insect bites, burns, swelling, and other skin diseases. The juice extracted from the plant is said to help reduce fevers, lessen joint pain, increase memory function, and decrease respiratory congestion. The leaves of the Eclipta plant can also be boiled to produce a black hair and body dye. Medicinally, usage of the Eclipta plant is considered safe with no adverse side effects." This is an assumption, however, based upon the fact that rats and mice treated with Eclipta plant extracts show no signs of toxicity" [6] .

The Eclipta plant has been incorporated into a variety of dietary supplements that can be bought directly through pharmaceutical companies or at local drug stores. One particular research group, The Allergy Research Group offers a dietary supplement titled "Eclipta Morinda." The supplement is hypoallergenic and contains 1200 mg of Eclipta leaf extract per capsule. The possible benefits of the "Eclipta Morinda" supplement are "hepatoprotective activity, health of the mind, nerves, liver, eyes, and hair, increase in cellular energy production, immunity, strenght and recovery" [3].

Eclipta Tablets, Healing Arts Alliance, Copyright 2007. Permission Requested.
http://www.healing-arts-alliance.com/herbs.htm

Effective Agents in Eclipta

The major effective agent in the Eclipta plant is Wedelolactone and its derivatives dimethylewedelolactone-7-glucoside and nor-wedelolacetone. These chemical compounds are found within the dried leaves of Eclipta alba [6]. 2.2:5.2:5-terthienylmethanol is also contained within the leaves. Other effective agents in the Eclipta plant are polyacetylene substituted thiophenes, hentriacontanol, and heptacosanol. These chemical compounds are contained within the roots of the plant [6]. Phytosterol, beta-amyrin, and beta-glucoside of phytosterol are found in the aerial regions of Eclipta. Also, stigmasterol and nicotine are found throughout the entire plant.

Wedelolactone is a furanocoumarin with the chemical formula C16H10O7. It is a yellow-green solid with a molecular weight of 314.3 [7]. Wedelolactone is also a selective and irreversible inhibitor of kinase activities within the cell." Wedelolactone inhibits NF-KB-mediated gene transcription in cells by preventing the phosphorylation and dissemination of IKB-alpha" [9].

Chemical Information about Wedelolactone

The systematic name of Wedelolactone is 7-Methoxy-5,11,12-trihydroxycoumestan. Wedelolactone has no common names other than Wedelolactone.


Wedelolactone Information
Common Name: Wedelolactone
Systematic Name: 7-Methoxy-5,11,12-trihydroxycoumestan
Molecular Weight: 314.25
Molecular Formula: C16H10O7
CAS Number: 524-12-9

Wedelolactone Chemical Structure, Sigma-Aldrich, Copyright 2007. Permission Requested.
http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/W4016

Isolation and Synthesis of Wedelolactone

In 1956, Wedelolactone was first isolated from an extract of a plant called Wedelia calandulaceae . Shortly after this first isolation, Wedelolactone was obtained from the Eclipta plant. Extracting Wedelolactone from these plant sources proved difficult due to the fact that "Wedelolactone contains oxygenated polyphenols which decompose under basic conditions" [9]. Because Wedelolactone demonstrates a variety of medicinal uses, and medical benefits, its synthesis for use in pharmeuctical drugs has been throughougly investigated. In 1999, researchers at the College of Chemistry in Peking University developed a method to synthesize Wedelolactone, in large quantities, in order for Wedelolactone to be further investigated for possible drug design. The researchers proposed that a terminal acetylene, connected to a benzene ring, be added to a phenyl iodine in the presence PdCl2(PPh3)2, CuI, Et3N, and CH3CN. This reaction produces a di-benzene molecule connected through a carbon-carbon triple bond. This intermediate can then be treated with NH2NH2-H2 and THF to turn a AcO group into an OH group. The resulting intermediate is treated with PdI2-thiourea, CBr4, Cs2CO3, MeOH, THF, and CO at 50 degrees celcius to produce an intermediate with two benzene rings and one furan ring. Treating this intermediate with Pd-C, H2, and EtOAc causes a BnO group to become an OH group. Treating this final intermediate with 10% sulfuric acid and AcOH produces Wedelolactone. The synthesis of Wedelolactone reaction, determined by the researchers is below:


Synthesis of Wedelolacetone, C.C. Li, Copyright 2003. Permission Requested.
http://mutex.gmu.edu:2343/acs/journals/doilookup?in_doi=10.1021/jo030228f


The researchers at the University of Chemistry at the University of Bejing were able to synthesize Wedelolactone using their prosposed reaction and "obtain 93% Wedelolactone" [9]. To ensure that the synthesized Wedelolactone was indeed the same as naturally occuring Wedelolactone, the researched obtained a NMR spectrum of both the synthesized Wedelolactone and extracted Wedelolactone from Eclipta alba. Both the synthesized and natural occuring Wedelolactone yielded the same NMR spectrum concluding that the researchers had developed a synthetic pathway for the production of naturally occuring Wedelolactone.
In 2001, the ACS Journal of Organic Chemistry featured an article, by Wu, Liao, and Yang, on the synthesis of 4-substituted coumarins. Coumarins are a class of benzopyrons which occur in nature and include Wedelolactone. In the journal article, Wu, Liao and Yang, present their method for synthesisizing various coumarins, including Wedelolactone. In order to synthesize naturally occuring coumarins, "4-tosylcoumarin is mixed with a terminal acetylene and an organozinc reagent in a Sonogashira reaction" [10]. This method of synthesizing coumarins is quite different from the synthesis of coumarins using "palladium-catalyzed cross coupling reactions" such as the reaction used by the researchers at the Unviersity of Bejing. Wu, Liao, and Yang stress that their method of synthesizing coumarins is more efficient because the reagents are less expensive and the intermediates of the reaction are more stable.
In addition to synthesizing Wedelolactone, Wedelolactone derivatives have been synthesized. These Wedelolactone derivates contain a different oxygenation patterns in the four ring system of Wedelolactone [11]. Wedelolactone derivates have been determined to demonstrate nearly the same medicinal benefits as Wedelolactone.


Chem Sketch Drawing of Wedelolactone (All carbons in Wedelolactone are sp2 hybridized and therefore there are no carbon stereocenters) , Elissa Williams, Copyright 2007.


3D Optimization of Chem Sketch Drawing of Wedelolactone, Elissa Williams, Copyright 2007.


Other Interesting Eclipta Facts and Figures

Eclipta extracts are a common ingredient in hair oils, shampoos, conditioners, and hair dyes. When Eclipta leaf extracts are mixed with mineral oil and applied to the hair, "the hair will become dark and silky" [8]. Eclipta hair oil thus removes gray hairs. Eclipta extracts are a source of nutrition for the scalp and prevents hair loss. When the Eclipta hair oil is massaged into the scalp, "there is an increase in blood circulation cauing the hair roots to become stronger" [8]. The hair oil can also be made by boiling Eclipta leaf juice in coconut oil.


Eclipta, Herbalistics, Copyright 2007.
http://www.herbalistics.com.au/shop/index.php?cPath=3_10

Bibliography

  1. Tenaglia D., 2007. "Eclipta alba (L.) Hassk." Retrieved Feburary 23, 2007, from http://www.missouriplants.com/Whiteopp/Eclipta_alba_page.html

  2. Tropilab Inc., 2007. "Eclipta Tincture". Retrieved Feburary, 26, 2007, from http://www.tropilab.com/ecliptatincture.html

  3. Allergy Research Group, 2006."Eclipta-Morinda PDF Product Sheet". Retrieved Feburary 26, 2007, from http://www.allergyresearchgroup.com/proddesc/discuss/Eclipta-MorindaPDFProductSheet081706.pdf

  4. Plants for a Future, 2004. "Eclipta prostrata". Retrieved Feburary 26, 2007, from http://www.ibiblio.org/pfaf/cgi-bin/arr_html?Eclipta+prostrata

  5. United States Department of Agriculture, 2007. "Plants Profile: Eclipta prostrata (L.) L.. Retrieved Feburary 26, 2007, from http://plants.usda.gov/java/profile?symbol=ECPR

  6. ICS-Unido. Database on Important Medicinal and Aromatic Plants. "Eclipa alba (L.) Hassk." Retrieved Feburary 27, 2007, from http://www.ics.trieste.it/MedicinalPlant/_MedicinalPlant.aspx?id=36

  7. Biomol Int., LP. Online Catalog ."Wedelolactone." Retrieved Feburary 27, 2007, from http://www.biomol.com/Online_Catalog/Online_Catalog/Products/Product_Detail/38/?categoryId=181&productId=2490

  8. Aclepsa.com, Online Health Superstore, 2007. "Eclipa Raj Hair Oil." Retrieved Feburary 27, 2007, from http://www.aclepsa.com/eclipta-raj-hair-oil.shtml

  9. Li, C.C. J. of Organic Chemistry 2003, 68, 8500-8504. "Total Synthesis of Wedelolactone." http://mutex.gmu.edu:2314/cgi-bin/article.cgi/joceah/2003/68/i22/pdf/jo030228f.pdf

  10. Wu, J., Liao, Y., Yang, Zhen., J. of Organic Chemistry 2001, 66, 3642-3645. "Synthesis of 4-Substituted Coumarins via the Palladium-Catalyzed Cross-Couplings of 4-Tosylcoumarins with Terminal Acetylenes and Organozinc Reagents." http://mutex.gmu.edu:2314/cgi-bin/article.cgi/joceah/2001/66/i10/pdf/jo0102157.pdf

  11. Alcides J. M. da Silva, Paulo A. Melo, Noelson M. V. Silva, Flávia V. Brito, Camilla D. Buarque, Daniele V. de Souza, Verônica P. Rodrigues, Elisa S. C. Poças, François Noël, Edson X. Albuquerque, et al. Bioorganic & Medicinal Chemistry Letter 2001, 3, 283-286. "Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation." http://mutex.gmu.edu:2096/science?_ob=ArticleListURL&_method=list&_ArticleListID=544441412&_sort=d&view=c&_acct=C000035118&_version=1&_urlVersion=0&_userid=650615&md5=27eb267355a70f1caee2b5bc2614a802

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