View of A REVISED APPROACH FOR EXTRACTING RHEIN FROM SENNA

(1)

ACCENT JOURNAL OF ECONOMICS ECOLOGY & ENGINEERING

Peer Reviewed and Refereed Journal ISSN NO. 2456-1037 IMPACT FACTOR: 7.98 (INTERNATIONAL JOURNAL) Vol. 04, Issue 08,August 2019 Available Online: www.ajeee.co.in/index.php/AJEEE

1

A REVISED APPROACH FOR EXTRACTING RHEIN FROM SENNA

Kadasi Sundeep

Assoc. Professor, Department of Pharmaceutical Chemistry, Princeton College of Pharmacy, Hyderabad, Telangana, India

Hariprasad Kadiyam

Assoc. Professor, Department of Pharmaceutical Chemistry, Princeton College of Pharmacy, Hyderabad, Telangana, India

Abstract - The hydrolysis of the sennosides and the extraction of the hydrolysis products (free anthraquinones) are carried out in one step in a straightforward and effective method for isolating rhein from Cassia angustifolia (senna) leaves. The anthraquinone mixture is used to isolate rhein once more. When compared to more traditional approaches, this one requires fewer steps to isolate rhein than other methods.

Keywords: Aloe-emodin, Sennosides, Rhein, and Cassia angustifolia.

1 INTRODUCTION

In the free state and as a glucoside, Rhein (1, 8- dihydroxyanthraquinone-3-

carboxylic acid) can be found in Rheum species' senna leaves; and also in a number of Cassia species[1]. Due to its antiviral, antitumor, and antioxidant properties, Rhein is currently a topic of interest. Additionally, it is utilized as a starting material for the synthesis of diacerein (fig. 1,8- diacyl derivative). 1), which is

helpful in treating osteoarthritis and has anti-inflammatory properties. Rhein from indigenous plant sources must therefore be extracted in a straightforward and effective manner. Oxidative hydrolysis of aloin, a C-glycoside found in Aloe species, to obtain aloe-emodin, acetylation of aloe- emodin, and chromic oxidation of the acetylated product to obtain diacerein is currently the preferred method for the synthesis of diacerein[2].

Fig. 1 Rhein and its 1,8-diacyl derivative (diacerein)

(2)

2 Senna (Cassia angustifolia) is a little bush that is generally developed in southern India, essentially in Tamil Nadu. This plant's leaves and pods contain at least 2.5% anthraquinone glycosides, primarily sennosides A and B (fig.). 2), which are aloe- emodin and rhein-derived dianthrone glucosides. Because of this, senna leaf is a significant source of rhein. A straightforward method for separating rhein from

senna leaf is described in the following paper.

The Mumbai market served as the source for the C.

angustifolia leaves. Sodium hydrogen carbonate and hydrochloric corrosive were of insightful grade and were bought from S. D. Fine Substance Restricted, Mumbai. The leaves were ground up into a powder, and the powdered leaves were used for extraction.

Fig. 2 Anthraquinone glycosides (sennosides) present in senna leaves.

25 grams of powdered senna leaves were mixed with a mixture of 75% water and alcohol. 5 milliliters of hydrochloric acid were added after the mixture was slightly warmed. After incorporating one hundred milliliters of toluene into a biphasic mixture and refluxing it for six hours, the mixture was slightly cooled, filtered to remove any

crude drug, and the aqueous and organic layers were separated from one another. To recover any free anthraquinones and combine the toluene layers, the crude drug and aqueous layers were washed with toluene. The pink color of the aqueous layer was removed by partitioning the toluene layer with 10% sodium hydrogen carbonate solution. Hydrochloric acid was

(3)

3 used to acidify the aqueous layer, and ethyl acetate was used to dissolve the precipitate. The product was made from glacial acetic acid after the ethyl acetate layer was evaporated. Chemical tests and spectral studies were conducted on the obtained dark yellow compound to determine its identity. Borntrager's reagent was used to treat the isolated compound in an alcoholic solution (5 percent alcoholic potassium hydroxide); Anthraquinones were found to be present, as evidenced by the pink color.

Using ethyl acetate, thin- layer chromatography was carried out on a precoated silica gel G60 F254 plate (E. Merck): methanol:

With water serving as the mobile phase, Borntrager's reagent produced a pink color due to the presence of a single band at Rf 0.3.

On a Perkin- Elmer FTIR spectrometer, the isolated compound's infrared (IR) spectrum was recorded. A large peak at 3063 cm-1 (hydroxyl), 1629 cm-1 (chelated carbonyl), and 1696 cm- 1 (carboxyl) was observed in the infrared spectra. Mass range, was recorded on a Micromass, Q-TOF MS ES+. The compound's molecular weight was determined by the molecular ion peak at 285 m/e. The UV/Vis range was recorded on a Jasco V-530 UV/Vis Spectrophotometer. Methanol's UV/Vis maxima (nm) were discovered at 228, 258 (for Ar- C=O) and 432 (for the quinonoid

group)[5]. In view of substance tests and unearthly examinations, the segregated compound was distinguished as rhein.

On a laboratory scale, it was found that the above-described method of hydrolyzing and extracting anthraquinones in a single step using a biphasic system was effective for isolating rhein.

The rhein so acquired can be utilized for the amalgamation of diacerein and different subsidiaries of rhein. This method needs to be improved further in order to be suitable for large-scale extraction.

REFERENCES

1. Windholz M. editor. The Merck Index: An Encyclopaedia of Chemical, Drugs and Biologicals, 10th ed. Rahway, NJ: Merck Publications; 1983. p. 1179.

2. Vittori N, Collins M. Production of rhein and rhein derivatives. US Patent 5652265, 1997.

3. WHO Monographs on selected medicinal plants, Vol. 1, World Health Organization: Geneva;

1999. p. 244.

4. Trease GE, Evans WE, editors.

Pharmacognosy. 15th ed. London:

Hartcourt Publishers Limited;

2002. p. 230.

5. Gyanchandani ND, Nigam IC.

Anthraquinone drugs II:

Inadvertent acetylation of aloe- emodin during preparation of aglycone from crude drug- UV, IR and NMR spectra of the products.

J Pharm Sci 1969; 58:834.