A Review on Phytochemistry, Spermidine alkaloids and Stachydrine: Capparis decidua (Forssk.) Edgew
Prashant Kumar Dhakad1*, Pramod Kumar Sharma2, Raghav Mishra3
1Asst. Professor, School of Pharmaceutical Sciences, Jaipur National University, Jagatpura,
Jaipur, 302025 Rajasthan.
2Pro VC and Dean, School of Medical and Allied Sciences, Galgotias University, Greater Noida, U.P.
3Asst. Professor, Institute of Pharmaceutical Research, GLA University, Mathura, 281406, U.P.
*Corresponding Author E-mail: dhakadprashant654@gmail.com
ABSTRACT:
A few spermidine alkaloids have been portrayed in writing as constituents of the root bark of Capparis decidua. Four noteworthy spermidine alkaloids of the codonocarpine type were recognized and their structures explained in this review. The present audit portrays the different disengaged spermidine alkaloids of codonocarpine in concentrate of Capparis decidua in writing study. Pharmacological possibilities of the Capparis decidua plant can be ascribed to the nearness of a wide scope of phytochemicals including alkaloids (capparisinine, capparisine, stachydrine, isocodonocarpine), phenolics, flavonoids, sterols and unsaturated fats. This survey likewise centers around nitty gritty Phytochemistry of Capparis decidua. The structures of the four alkaloids were substantiated by NMR and MS information, and the four mixes are in coherent concurrence with biosynthetic contemplations: they would emerge from α,ω-bis-adducts of spermidine with coumaric as well as ferulic acids, trailed by phenol oxidation. In this article we additionally uncover the examination on the portrayal of stachydrine done.
KEYWORDS: Spermidine alkaloids, Codonocarpine, Capparis decidua, Phytochemistry, Stachydrine.
INTRODUCTION:
The "proof based" search, truth be told, has demonstrated very effective: for example, of the 1073 new medications presented in the time of 1980 to 2010 [5], 64% were motivated by common items and despite the fact that various elective methodologies for medication revelation are entrenched, the pool of regular items is as yet considered as an important wellspring of new pharmaceuticals [3].
To have a sound reason for medication disclosure dependent on regular items, notwithstanding, not just creatures that offer ascent to organically dynamic concentrates must be recognized. It is of essential significance, too that the compound constituents that may be in charge of the watched natural impacts are dependably portrayed and basically allocated. Such a portrayal is as yet pending for some codonocarpine type alkaloids that were depicted as constituents of Capparis decidua (Forssk.) Edgew. This plant is broadly found in the dry areas of Africa, the Middle East, and southern Asia, where it is widely utilized in nearby conventional prescription for the treatment of numerous scatters [6,7].
PHYTOCHEMISTRY:
C. decidua has been found to contain various alkaloids, terpenoids, glycosides, and unsaturated fats. The root bark of C. decidua has been accounted for to contain two sitosterols (24-b-methylcholest-7-ene-22-one-3 b-ol and 24-b-methylcholest-9 (11)- ene-22-one-3a-ol), one diterpene liquor (3-methyl-7-hydroxymethylene-10-(12, 16, 16-trimethylcyclohex-11-enyl)- dec-9-ene-5-one-8-ol), two aliphatic constituents (butyl-3-oxoeicosanoate and 25-oxooctosan-1, 20-diol) and one diterpenic ester(9-(11,15,15-trimethylcyclohex-11-ene-13-one-yl)-one-6-hydroxymethylene-7-one-yl, 40-Methyl heptanoate). Spermidine and spermine polyamines are found to have a significant job in the expansion, development, and improvement of mammalian cells. Additionally, these mixes likewise had cancer prevention agent, hostile to arteriosclerotic, and against allergenic properties. These polyamines have additionally been seen to advance sound hair development which can be clarified based on their cell proliferative properties. Isocodonocarpine, capparisinine and capparidisine are the significant spermidine alkaloids detached from root bark of C. decidua. Among different alkaloids, 14-N-acetyl isocodonocarpine, 15-N-acetyl capparisine, cadabicine, stachydrine, capparisine and codonocarpine have been confined from root bark. The structures of some the alkaloids present in the C. decidua are appeared in Fig. 1. Significant oxygenated heterocyclic constituents present in root bark of C. decidua were portrayed by ghastly examinations and recognized as 7,11,15,19-tetramethyleicos-13-ene-17-ol-6, 21-olide, 13-(15,19–19-trimethylcyclohex-14,17-diene-16-oneyl)- 10-methyI-6-hydroxymethylenetridec-10-ene-7,8,12-triol-5-(20)- olide, 13-(15,19-trimetylcyclohex-14,17-diene-16-one-yl)- 100-methyl-6-hydroxymethylene-tridec-6-ene-1,8,12-triol-5,(20)- olide, 14-(16,20,20-trimethylcyclohex-15,18-diene-17-one-yl)- tetradec-3-ene-13-ol-1(5),8(24)- diolide, 14-(16,20,20-trimethylcyclohex-15,18-diene-17-one-yl)- 11-ethylpentadec-1, 22-dihy droxymethylene-7-ene-13-one-6,21-olide and 19-(21,25,25-trimethyl cyclohex-20) 30-diene-22-one-yl)- 16-methyl-nona dec-8-ene-14-one-8-hydroxymethylene-18-ol-7,26-olide-28-oic acid, individually. The roots of C. decidua contained crystalline, dry and hygroscopic alkaloids, for example, capparine, cappariline and capparinine. The constituents of the ethereal pieces of C. decidua included one shikimate subordinate, two non-cyclic terpenoids, four unsaturated fats, two sterols and two lupine terpenoids. The two sesquiterpene lactones, germacr-3b-ol-7, 9-dien-6, 14-olide-15-oic acid and germacr-3b-ol-12-ene-6,14-olide-15-oic acid were likewise disconnected from the methanolic concentrate of ethereal parts. Glucocapparin and methyl isothiocyanate were separated from methanolic seed extricate. Isothiocyanates have been accounted for to display disease preventive action. N-pentacosane, β-sitosterol and β-carotene have additionally been secluded from unsaponifiable part of seeds. The hydrocarbon part of blooms contained nonacosane and triacontane. Ascorbic acid (1190 mg kg-1), phytic acid (680 mg kg-1), oxalic acid (1 mg kg-1), and phthalic acid have additionally been researched in the blooms and natural product husk. Two new soaked aliphatic ketones (C28 and C32), n-nonacosanol, β-sitosterol, β-D-glucoside of β-sitosterol, another isomer of β-sitosterol, another glycoside, pelargonidin-3-galactoside, glucocappasalin, glucocapparin, and two free sugars, D glucose and D galactose are different phytochemicals present in roses of plant. Stachydrine (2-carboxy-1, 1-dimethyl pyrrolidine) was recognized in the organic product mash, natural product husk, and blooms. Escapade foods grown from the ground husk contained a lot of carotene (210 mg kg-1). Among flavonoids, isorhamnetin was investigated in the leaves of C. decidua. Leaves additionally comprised of phenolic constituents, for example, phydroxybenzoic acid, protocatechuic acid, salicylic acid, syringic acid, vanillic acid, gentisic acid, 2-hydroxy-6-methoxybenzoic acid, and sinapic acid. The structures of chosen acidic phytochemicals from C. decidua are given in Fig. 2 [8].
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Isocodonocarpine |
Capparisine |
Capparidisine |
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Codonocarpine |
Capparasine |
15-N-acetylcapparasine |
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14-N-acetylcodonocarpine |
Stachydrine |
Cadabicine |
Figure 1: Chemical structures of different phytochemical found in Capparis decidua.
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Protocatechuic acid |
Syringic acid |
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Vanillic acid |
Gentisic acid |
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Sinapic acid |
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Figure 2: Representation of various acidic phytochemical found in different parts of Capparis decidua.
ISOLATION, PURIFICATION, AND SPECTROSCOPIC CONCERN:
In an investigation the UHPLC-UV(DAD)- HR-ESI-MS of the rough methanolic concentrate of the root bark of C. decidua demonstrated that separated particle chromatograms (EIC) for m/z 436, 466, 496, 598, 628, and 658 uncovered the nearness of two gatherings of exacerbates that are identified with the codonocarpines. The pinnacles enlisted at higher maintenance times (tR= 4.2-4.4 min) relate to the real alkaloids. The pinnacles recorded at lower maintenance times (tR =3.4-3.7 min) were less extreme and are considered to emerge from glycosidic subsidiaries of the fundamental alkaloids. The exact masses of their individual basic ionized particles coordinate the substance formulae of the alkaloids in addition to an extra unit of C6H10O5. Just when the HPLC segment was intensely over-burden, little crests for particles with m/z 508 and 538d however not for particles with m/z 478d were identified which demonstrated that acetylated alkaloids may likewise be available in the concentrate, yet just in follow sums. Capparis decidua extricates chromatography on SiO2 with dissolvable blends of changed structures indicated 3 portions containing alkaloids with the majority 435 Da, 465 Da, and 495 Da, separately. The chromatograms propose that the three portions contain four noteworthy alkaloids. The four noteworthy mixes were seen as the alkaloids: cadabicine, isocodonocarpine, codonocarpine, and capparidisinine. The minor parts were most presumably mono-(Z)- subsidiaries of these mixes. The structures of the real mixes were reasoned essentially based on the total arrangements of the NMR spectra of their hydrochlorides (1H, 13C, Cozy, NOESY, HSQC, and HMBC), together with data from the HR-ESI-MS. From the sign appropriations in the NMR spectra it ended up clear that the four mixes have a place, true to form, to the class of the Codonocarpine type alkaloids. For each intensify, the sign for two cinnamic acid units were promptly perceived in the 13C NMR spectra d two singlets in the carboxylic area (at approx. d 169) and 14 flag in the fragrant/alkene area (at approx. d 110-160) d, and the run of the mill signals for the aliphatic carbons of a spermidine moiety were found at approx. d 25-50 (7 triplets). For the alkaloids of higher masses, extra quadruplets for methoxy bunches at approx. d 57 were identified [9].
CHARACTERISATION OF STACHYDRINE:
In another examination rosy darker shading crystalline powder (stachydrine) separated from C. decidua was dissolvable in methanol, ethanol and water having softening point in the scope of 132–135˚C and sub-atomic equation C7H1402N and sub-atomic weight 144. One-dimensional 1H-NMR spectra gave reverberation crests (2.50–4.56ppm), at 4.56 (1H, t, J=9.8 Hz), 4.00 to 3.96 (1H, m), 3.84 (1H, dd, J=9.8 Hz), 3.58 (3H, s), 3.38 (3H, s), 2.84 to 2.72 (1H, m), 2.70 to 2.55 (1H, m), 2.50 to 2.38 (2H, m). 13C-NMR trials were reliable with those detailed for stachydrine. The sign in CDCl3 were alloted to C-2, C-5, N-CH3, N-CH3 and C-3 and C-4 protons, separately, at 4.56 δ (m, 1H), 3.78 δ (m, 2H), 3.37 δ (S, 3H), 3.54 δ (S, 3H) and expansive multiplets in the district 2.3–3.08 (4H). The alkaloid stachydrine gave solid sub-atomic particles, MH+ at 144.3m/z. The UV retention range demonstrated a band at 226.5nm in CHCl3 and IR range indicated groups at 3469.80 cm-1 (N-H str), 1635 cm-1 (C=O str), 1386.31 cm-1 (C–H def), 837.69–624.29 cm-1 (C-C def). The spectroscopic estimation information coordinated with the detailed information, the crystalline powder was affirmed to be stachydrine [10].
ISOLATION OF PHYTOCHEMICALS:
Alkaloids:
Hydro-methanolic extract (1:1, w/v) was utilized to obtain the phytoconstituents of root bark of Capparis decidua. It was then focused and 4 alkaloids codonocarpine (2, 465 Da), cadabicine (1, 435 Da), capparidisinine (4, 495 Da) and, isocodonocarpine (3, 465 Da) were separated utilizing column and thin layer chromatography [11]. In another investigation, roots were extricated with ethanol and undergone chromatography to segregate drab, crystalline, and hygroscopic alkaloids, for example cappariline (melting point 188°C), capparinine (melting point 229°C) and capparine (melting point 236°C) utilizing chloroform-methanol (80:20, 90:10, 20:80, and 50:50) [12]. In a past report, generally ground defatted plant material was separated with ethanol utilizing consistent hot extraction technique. At that point the liquor content was isolated from the concentrate in-vacuo until the arrangement of a semi-strong buildup, which was suspended in 400mL of refined water, shaked for two hours and separated. Nearness of alkaloids was demonstrated in the combined watery filtrates. Alkaloids were encouraged out as yellowish-dark colored accelerates [13].
Saponins:
Aerial plant parts were blended in with 50mL of 20% hydroalcohol and resultant suspension was warmed with persistent mixing over a heated water shower for 4 h at 55°C. The blend was separated and afterward buildup was re-removed with new 50mL of 20% watery ethanol. The extract was heated to 10mL over water shower at 90°C and afterward fractionated in separating funnel into diethyl ether and fluid parts. The fluid layer was recuperated and 15mL of n-butanol was added to it. The joined n-butanol separates washed twice with 10mL 5% watery sodium chloride. The rest of the arrangement was warmed over water shower to get the saponins [14].
Tannins:
5g of the dried natural product test was mixed with 50mL refined water for 1 h in a shaker. The filtrate was weakened to 50mL with distilled water. This filtrate (5 mL) was blended in with 3mL of 0.1 M FeCl3 in 0.1 N HCl and 0.008 M potassium ferrocyanide. The absorbance of the arrangement was estimated at 605nm. A similar system was rehashed with the clear [15].
Phenolic compounds:
Fluid concentrate of natural product (100μL) was shaken with 1.15mL of distilled water and 250μL of Folin Ciocalteu reagent and afterward 1.5mL of 20% sodium carbonate was included. The dilution with distilled water (2mL) was done after 2 h and absorbance was noted at 765nm. Total phenolic content were communicated regarding Gallic acid proportionate. In another study air-dried plant material (100g) was macerated in methanol-water solution (85:15 v/v). Subsequent to keeping 24 h in dull, the suspension was sifted through Buchner channel and the filtrate was exposed to fixation on a rotational evaporator to give rough concentrate. Lipid part was disposed of by extraction with hexane. The water division was then re-separated with chloroform and ethyl acetic acid derivation, each part being dissipated to dryness. At that point 0.1mL of plant separate was blended in with 2.5mL of distilled water and 0.5mL of the Folin–Ciocalteu stock reagent leaving it for 5 min. At that point 1.0mL of sodium carbonate reagent (20%) was added to the blend. The blend was left for 1 h at room temperature. Absorbance of the blend was estimated with the assistance of spectrophotometer at wavelength 760nm. Polyphenol content was determined from a standard bend of gallic acid and communicated as gallic acid proportional [16].
Flavonoids:
Aluminium chloride colorimetric method was used for determination of flavonoids [17]. Fruit extract (250μL) of C. decidua was diluted with distilled water (4.5mL) and then NaNO2 (5%, 0.3mL) was added. After 5 min, AlCl3 (10%, 0.3mL) was mixed with solution. After 6 min, NaOH (1 M, 2mL) solution was mixed with prepared solution and volume was made up to 10mL with distilled water. The absorbance was noted at 510 nm using rutin as standard [18]. AlCl3 reagent was used for flavonoids measurement by UV spectroscopy. A mixture was prepared by mixing 1mL of plant root extract, 1mL of aerial extract, 1mL of AlCl3 in methanol. Leaving at room temperature for 10 min, the absorbance of mixture was obtained at 430nm. In another study, powdered leaves of C. decidua were extracted with 80% hot ethanol on a water bath for 24 h. [19]. The extracts were concentrated and re-extracted with petroleum ether, ether and ethyl acetate in succession. Ethyl acetate fraction was dried in-vacuo and the concentrate was treated with 7% sulfuric acid for 2 h. The fraction was filtered, concentrated and applied on chromatgraphy plates. The plates were treated with the solvent system n-butanol, acetic acid and water (4:1:5). Kaempferol and quercetin were detected on the plate, which were then isolated through preparative chromatgraphy [20].
In another examination, confinement of phenolic mixes were done utilizing a technique. The air-dried plant material (100g) was dumped into 1000mL of methanol-water arrangement (85:15 v/v). Subsequent to keeping 24 h in dull, the suspension was sifted through Buchner channel and the filtrate was exposed to fixation on a rotational evaporator to give rough concentrate. Lipid part was disposed of by extraction with hexane. The water division was then re-separated with chloroform and ethyl acetic acid derivation, each part being dissipated to dryness. At that point 0.1mL of plant separate was blended in with 2.5mL of refined water and 0.5mL of the Folin–Ciocalteu stock reagent leaving it for 5 min. At that point 1.0mL of sodium carbonate reagent (20%) was added to the blend. The blend was left for 1 h at room temperature. Absorbance of the blend was estimated with the assistance of spectrophotometer at wavelength 760nm. Polyphenol content was determined from a standard bend of gallic corrosive and communicated as gallic acid proportional [21].
Lipid compounds:
Air dried bark of Capparis decidua changed over into coarse powder and exposed to constant hot extraction utilizing ether, petroleum ether, chloroform, and ethanol as solvents. Gotten removes were vanished to steady loads. Petroleum ether extricate was then exposed to saponification to isolate the non-saponifable substance. A dark colored non-crystalline issue was acquired, which was then gone through a section of alumina. An aggregate of 30 eluates part were gathered. Initial five with oil ether followed with benzene till ninth, at that point a blend of benzene with ether (4:1) till eighteenth, next dry ether till 28th, and in conclusion outright ethanol. Crystals were acquired during elution with a blend of benzene and ether (4:1) in portion 11–17 with m. p. of 78–79°C. The acetic acid derivation subsidiary of compound dissolved at 68°C and this substance compares to n-triacontanol. During elution with dry ether, another crystalline item was acquired in portions 19–26. This item gave agreed outcomes with Hesses, Liebermann and Liebermann-Burchard tests. The unadulterated precious stones of this item liquefied at 136–137°C. The m.p. of the substance, its acetic acid derivation subsidiary and its optical pivot relates to β-sitosterol [13].
CONCLUSION:
Capparis decidua uncovered four noteworthy codonocarpine type alkaloids. One of the four compounds, isocodonocarpine, was recently portrayed as a constituent of such a concentrate, and a second, cadabicine, was proposed as a potential segment. Structure of capparidisine fits legitimately into the biosynthetic plan that must be proposed for Codonocarpine type alkaloids: arrangement of α,ω-bis-adducts of spermidine with coumaric or potentially ferulic acid, trailed by phenol oxidation. The examination on portrayal of stachydrine additionally correspond the natural and utilitarian parts of Capparis decidua for further investigations. The phytochemicals found in Capparis decidua possess pharmacological potentials to act against several diseases and acts as a major concern for researchers to explore the biological activities.
CONFLICT OF INTEREST:
The authors declare no conflict of interest, financial or otherwise.
ACKNOWLEDGEMENTS:
This research received no specific grant from any funding agency in the public, commercial, or not-for-profit sectors.
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Received on 11.02.2020 Modified on 18.04.2020
Accepted on 09.06.2020 © RJPT All right reserved
Research J. Pharm. and Tech. 2021; 14(2):1171-1176.
DOI: 10.5958/0974-360X.2021.00209.2