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1. Introduction
Calotropis procera is a traditional, medicinal, and therapeutic plant in Pakistan and native people of Pakistan as well as all over the world use it for health-related properties. This is a flowering plant and belongs to Apocynaceae family [1]. In different regions of the world, the common name of Calotropis procera is dead sea, Calotrope and Calotropis in English, madar and oak in India and Pakistan, isipekag in Turkish, extranjero, bomba, algodon, and cazuela in Spanish, while kisher and oshar in Arabic language [2]. The different parts of Calotropis procera, for instance, stem, root, flowers, latex, and leaves are used for therapeutic purposes [3].
Calotropis procera is present in different parts of the world, for instance, in Asian countries such as Afghanistan, Nepal, China, Malaysia, Indonesia, India, and Pakistan, in African countries such as Niger, Nigeria, and Kenya, and in the Australian continent, this plant is distributed widely [4].
Calotropis procera consists of a variety of phytochemicals, for instance, calotropenyl acetate and multiflavenol in flowers, calotropin and calotropagenin in leaves, uzarigenin and terpineol ester in latex, while benzoylinesolone and benzolisolinelone in root [5]. Procerleanol, calopfriedelenyl, triterpenoids, procerudenyl acetate, proceranol, mono-oleolyl-2-phosphate, N-doctriacont-6-ene, methyl behenate, and methyl myristate are the compounds present in Calotropis procera [6].
The family Apocynaceae comprises of 180 genera and 2000 species of which the medicinal plant, Calotropis procera belongs to. This plant is distributed in tropical and subtropical regions of the world and is grown in deserts with evergreen nature. The leaves of Calotropis procera are flat, fluffy, and soft and with single branches or some stem. The large leaves of this traditional plant touch the lower region of growth. A light grey color bark covers the stem. Sap is also present in this plant and is released by cutting the stem, flower, and leaf. The root of this medicinal plant reaches up to 1.7–3.0 meters at the depth of the soil. The length of leaves is up to 7–18 cm and breadth is up to 5–13 cm. The color of the leaves is dark green with the white color veins inside the leaves. On the surface of leaves, minor hair-like structures are present which by pressing or rubbing the leaves can be felt. The color of the flower is white to pink. Sepals are usually 5 in number with a length of 5-4 cm. A green color fruit is also present in this plant with enclosed brown color seed inside the fruit. A bunch of white hairs is present on the seed which help to establish the floral part of the plant with the help of water, animal, and wind and also helps to transport the seed at long distances [7].
Calotropis procera has the ability to tolerate the condition of drought for longer periods, grow in saline environments and sandy soil, ability for fighting diverse changes in the environment, adaptability to numerous environmental conditions, for instance, cold, heat, drought, and salinity [7]. The part of a rich source of ethnomedicines is latex which is very important [8]. At the age of 3–5 years, the height of the plant reaches from 2.5 to 6 m. Ropes, papers, nets and bags can be made from this plant [7].
The medicinal plant Calotropis procera is used for the treatment of diverse form of diseases in the entire world, for instance, boils, indigestion, eczema, tooth decay, diarrhea, paralysis, fever, hair fall, cold, rheumatism, joint pain, and jaundice. The root is used to cure dysentery, cough, eczema, leprosy, tumors, paralysis, bronchitis, digestion, inflammation, abdominal pain, skin diseases, kill worms in the intestine, body pain, enlarged abdominal viscera, headache, enlargement of spleen and liver, diarrhea, and asthma, while the stem is used to treat skin diseases and to kill intestinal worm [9–13].
The latex is used to cure the disease of leprosy, wounds, boils, to stop bleeding in the area of bleeding, painful joints, swelling, skin burn, snake bites, intestinal worms and splenic and hepatic enlargement, abortion of babies, and contraction of muscle of uterus during baby birth. Leaves are used for the treatment of joint pain and swelling and the body with paralyzed parts is treated with the oil extracted from leaves. Flowers are used to treat asthma, loss of appetite, stomachic, digestive problems, and cough [14–18]. In countries such as India, the leaves are used for worshipping purposes [19]. The picture of Calotropis procera plant is shown in Figure 1.
[figure(s) omitted; refer to PDF]
2. Materials and Methods
2.1. Plant Material
The traditional, medicinal, and therapeutic plant Calotropis procera (Linn) was analyzed for biological and GC-MS studies at the University of Turbat. Dr. Shazia Saeed, Department of Botany, University of Balochistan, Quetta, Pakistan identified Calotropis procera (Linn) and the voucher number is QUETTA 000230.
2.2. Extraction
Calotropis procera (Linn) was dried in its entirety for a month in the shade. This is caused by solar radiation, which eliminates bioactive chemicals found throughout the entire Calotropis procera (Linn). Calotropis procera (Linn) was dried and the whole plant was ground into a powder using a mechanical grinder. The plant powdered 0.4 kg was then macerated in 3 L of methanol for just one week, and the mixture was then concentrated at reduced pressure and below 55°C while being filtered using Whatman filter paper No. 1. This crude whole plant methanol extract of Calotropis procera (WMECP) was 37.1 g [20–23].
2.3. Fractionation of Crude Extract
Crude extract with nonpolar solvent such as n-hexane and polar solvent such as aqueous was fractionated into whole plant n-hexane fraction of Calotropis procera (WHFCP) 5 g and whole plant aqueous fraction of Calotropis procera (WAFCP) 14 g [20–23].
2.4. MTT Assay (HeLa, 3T3, and PC3 Cell Lines)
The American Type Culture Collection was used to purchase the cell lines of HeLa, 3T3, and PC3 (ATCC). A medium resembling Dulbecco’s Eagle-modified media was used. It contained 10% FBS and 2% antibiotics such as penicillin and streptomycin at 100 IU/mL and 100 μg/mL and then this overall is preserved in 5% CO2 which is at 37°C in this assay to create a culture of cancer cell line. Cell lines were extracted once confluence had formed. In a 96-well flat, 5, 104 cells were seeded in each well. Extracts and fractions containing 50 μg/ml were added after 24 hours. Cell lines and a sample were grown in a 96-well plate for 48 hours. Fractions and extracts containing 50 μg/mL were added after 24 hours. Cell lines and a sample were grown in a 96-well plate for 48 hours. The decrease of MTT led to the formation of formazan crystals. Crystals were dissolved by adding 100 μL of DMSO, and then, in order to measure using a microplate reader, at 570 nm, the absorbance was measured. The standard drug for HeLa, 3T3, and PC3 cell lines during the MTT assay was Doxorubicin.
In order to calculate the IC50, a stock solution of the fraction or extracts at a concentration of 20 mM is diluted into a working solution at a concentration of 50 μM. The working solution is then serially diluted to produce less than 50% inhibition. With the aid of the EZ-fit5 programme, the IC50 is determined [24].
2.5. Antileishmanial Activity
The fractions and extracts of therapeutic plants were evaluated against Leishmania major using microplates for culture (promastigotes). Leishmania major promastigotes (MHOM/PK/88/DESTO) were cultivated using bulk normal physiological saline in an NNN biphasic medium. The mixture was then concentrated at reduced pressure and below 55°C while being filtered using Whatman filter paper No. 1. There were 37.1 g of this whole plant methanol extract of Calotropis procera (WMECP). The leishmanial parasites were centrifuged for 10 minutes at 2000 rpm after the promastigotes were extracted at the log phase. At the same speed and timing, leishmanial major was washed three times in saline.
180 μL of the culture medium was added to each of the 96 wells of a microtitre plate. Fractions and extracts of therapeutic plants were dissolved in PBS with a pH of 7.4 and 0.5% DMSO and 0.5% MeOH to create a 1000 mg/mL stock solution. In order to create a working solution with a concentration range of 1–100 μg/mL, the fractions and extracts with a 20 μL concentration were added to wells and serially diluted. 100 μL of the parasite culture was given to each well. In this experiment, two rows remained: one for the positive control, which received typical antileishmanial drugs such as amphotericin B (Fluka) and pentamidine, and the other for the negative control, which received medium (ICN).96-well plates were then incubated at 21-22°C for 72 h. To calculate the IC50 values of fractions and extracts with antileishmanial activities, a Neubauer chamber with EZ-Fit 5.03 (Percella Scientific, USA) was used to count motile cells. The culture was inspected for indications of cell viability, such as [25, 26].
2.6. Antibacterial Activity
Pseudomonas aeruginosa (ATCC 10145), Staphylococcus aureus (NCTC 6571), Escherichia coli (ATCC 25922), and Salmonella typhi (ATCC 14028) were the five types of microorganisms employed in this investigation as standard bacterial strains. ICCBS, University of Karachi, Karachi, Pakistan, provided the PCMD with access to its collection of common bacterial strains.
2.6.1. Microplate Alamar Blue Assay
The antibacterial activity is assessed using this test. The growing medium for organisms was Mueller–Hinton medium. A McFarland turbidity index with a value of 0.5 was employed to modify the inoculums. By dissolving extracts in DMSO, the stock solution was created. Media was moved to each well. Except for the control well, where extracts were not added, wells had extracts added to them. The wells were made into 200 μL in size. Last but not least, 5 × 106 cells were added to both the test and control 96-well plates. The plate was sealed with parafilm with the aid of parafilm before being placed in an incubator for 18–20 hours. Alamar Blue Dye was applied to each well, and the plate was shaken for two to three hours at an RPM of 80. The color of the dye, for example, Alamar Blue dye was turned pink to demonstrate the development of bacteria. For the measurement of absorbance at 570 nm, an ELISA reader was used [27].
2.7. Antifungal Assay
As a standard fungal strain, seven fungi were employed in this study: Aspergillus niger, Candida albicans, Fusarium lini, Trichophyton rubrum, Microsporum canis, Candida glabarata, and Aspergillus fumigatus. Seven fungi were acquired from the Northern Regional Research Laboratories or given as gifts by the Karachi University Culture Collection (NRRL).
2.7.1. Agar Tube Dilution Method
It was performed by dilution of agar tubes to assess the extracts’ antifungal efficacy. Extracts were dissolved in 1 ml of DMSO at a concentration of 24 mg (Merck). SDA was made by dissolving Sabouraud, 4% glucose agar, and 4 g of agar-agar in 500 cc of distilled water (Sigma-Aldrich, Germany). Through a magnetic stirrer, mixture was then carefully stirred. This growth media was steamed until it totally dissolved, and then 4 ml was added to screw-cap tubes, which were subsequently autoclaved for 15 minutes at 121°C. After the tubes had cooled to 15°C and the SDA had not yet solidified, 66.6 μl of crude extracts were placed into them. At room temperature, tubes were allowed to harden in a slanting orientation. A 4 mm-diameter portion of the fungus was injected into the tubes. In other media, the negative control and the positive control, such as standard antifungal medicines, such as DMSO, were utilised. For 3–7 days, tubes were incubated at 27–29°C. Fungal cultures were checked twice a week while they were incubating [25, 28].
2.8. Anti-Inflammatory Assay
2.8.1. Oxidative Burst Assay Using Chemiluminescence Technique
Diluted whole blood in HBSS++ with the concentration of 25 μL including CaCl2 and MgCl2 was used (Sigma, St. Louis, USA) as well as the fractions and extracts of medicinal plants at a concentration of 25 μL were incubated at 37°C for 15 min. 96-well plates were then used to plate this mixture (CoStar, NY, USA). The unfinished wells were filled with HBSS++. Cells and HBSS++ were introduced to the control wells. 25 μl each of serum opsonized zymosan and luminol from the St. Louis-based Sigma Chemical Co., Missouri, the United States, was warmly received (Sigma Chemical Co., St. Louis, MO, USA). Relative light units were used to measure the ROS concentration in luminometers. Ibuprofen was used as a common treatment and had an IC50 of 11.2 1.9. [29].
2.9. Brine Shrimp Lethality Assay
2.9.1. B-Hatching Techniques
Using this approach, at 37°C for 2 days, 50 mg of shrimp eggs was incubated on a hatching tray with filtered brine solution, dissolved in 2 mL of a solvent, such as methanol, and in 20 mg of plant extracts and fractions. The concentration was increased to 10, 100, and 1000 μg/mL by dividing this solution into three vials and adding 5, 50, and 500 μl to each. The solvent was evaporated overnight. Each container received 30 larvae by Pasteur pipette addition. Seawater (5 ml) was then added. 24 hours of incubation at a temperature of 25−27°C with light was performed. Other vials included solvent-reference cytotoxic medication along with negative and positive controls. Etoposide, 7.4625 μg/mL, was the standard drug utilised in this investigation. The Finney computer programme was used to calculate the LD50 [30].
2.10. GC-MS Analysis
2.10.1. Triple Quadrupole Acquisition Method MS Parameters
We isolated and quantified chemicals from Calotropis procera in a column HP-5MS. 2 μL and mass spectrometer of the fraction or extracts were directly fed into the gas chromatograph mod using the 5973 Network Mass Selective Detector (Agilent Technologies Palo Alto, CA) 6890N Network GC System (0.25 mm interior diameter, 30 m length, and 0.25 μm film width; Agilent Technologies, Palo Alto, CA), and the incorrect variety of helium gas. A split-splitless injector at 250°C was injected using a 30 : 1 split ratio.
The oven’s schedule was as follows: 70°C for three minutes, followed by six minutes at 180°C, five minutes at 280°C, and finally ten minutes at 290°C. 250°C was the MSD transfer line’s temperature; the MSD quadrupole temperature was 150°C, the mass spectra were at 70 eV, the ionization temperature was 230°C, and the scan was successful in the series between 35 and 300 m/z. The identification of the components of the Calotropis procera extract or fraction was assigned by matching their mass spectra with those available in the libraries NIST 02 and WILEY [20, 21, 31].
3. Results and Discussion
In this research study, the medicinal plant of Balochistan, Calotropis procera was extracted and fractionated to form whole plant methanol extract of Calotropis procera (WMECP), whole plant n-hexane fraction of Calotropis procera (WHFCP), and whole plant aqueous fraction of Calotropis procera (WAFCP).
All the extracts and fractions of Calotropis procera exhibited significant anticancer activities against the HeLa cell line. Whole plant methanol extract of Calotropis procera (WMECP) inhibited 69.1% of the growth of the HeLa cell line with an IC50 value of 3.1 ± 0.4 and whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant and aqueous fraction of Calotropis procera (WAFCP) inhibited 70.2% and 65.2% with IC50 values of 5.0 ± 0.3 and 17.1 ± 1.0. The standard drug, doxorubicin inhibited the growth of HeLa cell line 100% with an IC50 value of 0.9 ± 0.14. Anticancer activities (HeLa cell line) of extract and fractions of Calotropis procera are shown in Table 1.
Table 1
Anticancer activities (HeLa cell line) Calotropis procera extract and fractions.
| S. no. | Extract/fraction/std. drug | Conc. (μg/mL) | % inhibition/stimulation | IC50 ± S.D. |
| 1 | WMECP | 30 | 69.1 | 3.1 ± 0.4 |
| 2 | WHFCP | 30 | 70.2 | 5.0 ± 0.3 |
| 3 | WAFCP | 30 | 65.2 | 17.1 ± 1.0 |
| 5 | Doxorubicin | 30 | 100 | 0.9 ± 0.14 |
All the extracts and fractions of Calotropis procera exhibited significant anticancer activities against the PC3 cell line. Whole plant methanol extract of Calotropis procera (WMECP) inhibited 70.1% of the growth of the PC3 cell line with IC50 value 5.1 ± 0.3 and whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant aqueous fraction of Calotropis procera (WAFCP) inhibited 61.6% and 59.7% with IC50 values 3.7 ± 0.5 and 16.4 ± 1.0. The standard drug, doxorubicin inhibited the growth of the HeLa cell line 89.9% with IC50 1.9 ± 0.14. Anticancer activities (PC3 cell line) of extract and fractions of Calotropis procera are shown in Table 2.
Table 2
Anticancer activities (PC3 cell line) of Calotropis procera extract and fractions.
| S. no. | Extract/fraction/std. drug | Conc. (μg/mL) | % inhibition/stimulation | IC50 ± S.D. |
| 1 | WMECP | 30 | 70.1 | 5.1 ± 0.3 |
| 2 | WHFCP | 30 | 61.6 | 3.7 ± 0.5 |
| 3 | WAFCP | 30 | 59.7 | 16.4 ± 1.0 |
| 5 | Doxorubicin | 30 | 89.9 | 1.9 ± 0.14 |
None of the extract and fractions of Calotropis procera showed anticancer activities against the 3T3 cell line. The standard drug doxorubicin inhibited 96.2% of the growth of the cell line with an IC50 value of 0.1 ± 0.02. Anticancer activities (3T3 cell line) of extract and fractions of Calotropis procera are shown in Table 3.
Table 3
Anticancer activities (3T3 cell line) of Calotropis procera extract and fractions.
| S. no. | Extract/fraction/std. drug | Conc. (μg/mL) | % inhibition/stimulation | IC50 ± S.D. |
| 1 | WMECP | 30 | 12.4 | Inactive |
| 2 | WHFCP | 30 | 14.1 | Inactive |
| 3 | WAFCP | 30 | 3.5 | Inactive |
| 5 | Doxorubicin | 30 | 96.2 | 0.1 ± 0.02 |
None of the extract and fractions of Calotropis procera showed antileishmanial activities and had an IC50 above 100. The standard drugs used for antileishmanial activities are amphotericin B and pentamidine with IC50 values of 3.41 ± 0.02 and 4.56 ± 0.01. Antileishmanial activities of extract and fractions of Calotropis procera are shown in Table 4.
Table 4
Antileishmanial studies of Calotropis procera extract and fraction.
| S. no | Extract/fractions/standard drugs | IC50 (μg/mL) ± S.D. |
| 1 | WMECP | >100 |
| 2 | WHFCP | >100 |
| 3 | WAFCP | >100 |
| 9 | Amphotericin B | 3.41 ± 0.02 |
| 10 | Pentamidine | 4.56 ± 0.01 |
The extract and fractions of Calotropis procera were inactive against bacterial strains. Ofloxacin was the standard drug used against bacterial strains with percent inhibitions of 92.54%, 92.41%, 93.05%, 92.68%, and 92.37% against Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, and Bacillus subtilis. Antibacterial activities of extract and fractions of Calotropis procera are shown in Table 5.
Table 5
Antibacterial studies of Calotropis procera extract and fractions.
| S. no | Extract/fraction/standard drug | Inhibition % | Inhibition % | Inhibition % | Inhibition % | Inhibition % |
| E. coli ATCC 25922 | B. subtilis ATCC 23857 | S. aureus NCTC 6571 | P. aeruginosa ATCC 10145 | S. typhi ATCC 14028 | ||
| 1 | WMECP | NI | NI | NI | NI | NI |
| 2 | WHFCP | NI | NI | NI | NI | NI |
| 3 | WAFCP | NI | NI | NI | NI | NI |
| 4 | Ofloxacin | 92.68% | 92.37% | 92.54% | 92.41% | 93.05% |
All extracts and fractions of Calotropis procera exhibited no antifungal activities. Miconazole and amphotericin B were the standard drugs used against seven strains of fungi, for instance, Aspergillus niger, Microsporum canis, Fusarium lini, Candida glabarata, Aspergillus fumigatus, Candida albicans, and Trichphyton rubrum. Antifungal activities of extract and fractions of Calotropis procera are shown in Table 6.
Table 6
Antifungal studies of Calotropis procera extract and fractions.
| S. no | Name of fungus | WMECP | WHFCP | WAFCP | Mic (μg/mol) | Linear growth (mm) of control | Linear growth (mm) of sample | Std. drug |
| Inhibition (%) | Inhibition (%) | Inhibition (%) | ||||||
| 1 | C. albicans | 0 | 0 | 0 | 110 | 100 | 100 | Miconazole |
| 2 | T. rubrum | 0 | 0 | 0 | 70 | 100 | 100 | Miconazole |
| 3 | A. niger | 0 | 0 | 0 | 20 | 100 | 100 | Amphotericin B |
| 4 | M. canis | 0 | 0 | 0 | 98.4 | 100 | 100 | Miconazole |
| 5 | F. lini | 0 | 0 | 0 | 73.25 | 100 | 100 | Miconazole |
| 6 | C. glabarata | 0 | 0 | 0 | 110.8 | 100 | 100 | Miconazole |
| 7 | Aspergillus fumigatus | 0 | 0 | 0 | 100 | 100 | 100 | Amphotericin B |
None of the extract and fractions of Calotropis procera showed anti-inflammatory activities. The standard drug used for anti-inflammatory activity is ibuprofen with 73.2% inhibition and an IC50 value of 11.2 ± 1.4 μg/mL. Anti-inflammatory activities of extract and fractions of Calotropis procera are shown in Table 7
Table 7
Anti-inflammatory studies of Calotropis procera extract and fractions.
| S. no | Extract/fraction/std. drug | Conc. (μg/mL) | % inhibition/stimulation | IC50 ± S.D. |
| 1 | WMECP | 50 | −20.1 | — |
| 2 | WHFCP | 50 | 12.8 | — |
| 3 | WAFCP | 50 | −3.7 | — |
| 5 | Ibuprofen | 25 | 73.2 | 11.2 ± 1.4 μg/mL |
The whole plant methanol extract of Calotropis procera (WMECP) exhibited lethality at the highest concentration, while other fractions, for instance, whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant aqueous fraction of Calotropis procera (WAFCP) did not exhibit lethality. Brine shrimp lethality bioassay of extract and fractions of Calotropis procera are shown in Table 8.
Table 8
Brine shrimp lethality bioassay of Calotropis procera extract and fractions.
| S. no | Extract and fractions | Dose (μg/mL) | No. of shrimps | No. of survivors | Mortality % | LD50 (μg/ml) | STD. Drug | LD50 (μg/ml) | Mortality% |
| 1 | WMECP | 10 | 30 | 29 | 3.3 | Etoposide | 7.5 | 70 | |
| 100 | 30 | 26 | 13.3 | ||||||
| 1000 | 30 | 18 | 40 | ||||||
| 2 | WHFCP | 10 | 30 | 30 | 0 | Etoposide | 7.5 | 70 | |
| 100 | 30 | 29 | 3.33 | ||||||
| 1000 | 30 | 29 | 3.33 | ||||||
| 3 | WAFCP | 10 | 30 | 30 | 0 | Etoposide | 7.5 | 70 | |
| 100 | 30 | 29 | 3.33 | ||||||
| 1000 | 30 | 29 | 3.33 | ||||||
GC-MS studies revealed that whole plant methanol extract of Calotropis procera (WMECP) consists of 11 compounds such as 12-methyloctadec-11-enoic acid trimethylsilyl ester, (1S.15S)-bicyclo[13.1.0] hexadecane-2-one, cholest-5-en-3-ol. (3@), melezitose, @-D-glucose, heptane. 1.7-dibromo, 1-decanol. 9-[(trimethylsilyl)oxy]-, trifluoroacetate, 15-tetracosenoic acid, methyl ester, isosorbide, 2TBDMS derivative, oleic acid, (Z)-TMS derivative, and 3.7.11.15.18-pentaoxa-2, 19-disilaeicosane, 2,2,19.19-tetramethyl. The chromatogram of whole plant methanol extract of Calotropis procera (WMECP) is presented in Figure 2. Name, molecular formula, molecular mass, RT, area, and % composition of compounds 1–11 of whole plant methanol extract of Calotropis procera (WMECP) are shown in Tables 9 and 10. Mass spectra of compounds 1–11 of whole plant methanol extract of Calotropis procera (WMECP) are shown in Tables 11 and 12. Structure and mass spectra of compounds 1–11 of whole plant methanol extract of Calotropis procera (WMECP) are shown in Figures 3–24.
[figure(s) omitted; refer to PDF]
Table 9
GC-MS of compounds 1–5 of methanol extract of Calotropis procera.
| Compound | Name | Molecular formula | Molecular Mass | RT | Area | % composition |
| 1 | 12-Methyloctadec-11-enoic acid trimethylsilyl ester | C22H44O2Si | 368 | 3.033 | 433982.7 | 1.167034018274278 |
| 2 | (1S.15S)-Bicyclo[13.1.0]hexadecane-2-one | C16H28O | 236 | 3.153 | 9035313 | 24.2970927834702 |
| 3 | Cholest-5-en-3-ol, (3@)- | C27H46O | 386 | 5.0259 | 222203.6 | 0.597533321427677 |
| 4 | Melezitose | C18H32O16 | 504 | 5.675 | 440087.3 | 1.18345020587543 |
| 5 | @-D-Glucose | C6H12O6 | 180 | 6.02 | 2432547 | 6.54142408623575 |
Table 10
GC-MS of compounds 6–11 of methanol extract of Calotropis procera.
| Compound | Name | Molecular formula | Molecular Mass | RT | Area | % composition |
| 6 | Heptane. 1.7-dibromo- | C7H14Br2 | 380 | 7.395 | 22935970 | 61.6777073654105 |
| 7 | 1-Decanol. 9-[(trimethylsilyl)oxy]-, trifluoroacetate | C15H29F3O3Si | 342 | 9.586 | 7243.527 | 0.0194787549251 |
| 8 | 15-Tetracosenoic acid, methyl ester | C25H48O2 | 380 | 10.577 | 14132.67 | 0.038004524023802 |
| 9 | Isosorbide, 2TBDMS derivative | C18H38O4Si2 | 374 | 12.292 | 124957.5 | 0.336026451531588 |
| 10 | Oleic acid, (Z)-. TMS derivative | C21H42O2Si | 354 | 13.443 | 893.462 | 0.002402631664504 |
| 11 | 3.7.11.15.18-Pentaoxa-2, 19-disilaeicosane, 2,2,19.19-tetramethyl- | C17H40O5Si2 | 380 | 13.558 | 972.03 | 0.002613910895872 |
Table 11
Mass spectra of compounds 1–5 of whole plant methanol extract of Calotropis procera (WMECP).
| Compound | m/z (% relative abundance) |
| 1 | 368(M+), 353(438), 243(329), 129(300), 117(389), 83(300), 77(609), 75(999), 73(879), 69(558), 55(820) |
| 2 | 236(M+), 98(340), 98(370), 96(310), 95(460), 82(430), 81(620), 71(400), 69(580), 67(580), 55(999) |
| 3 | 386(M+962), 368(755), 275(414), 107(427), 95(449), 81(465), 71(609), 69(491), 57(999), 55(641) |
| 4 | 504(M+), 97(603), 73(999), 71(364), 69(383), 61(361), 60(705), 57(587), 55(353), 43(534), 29(451) |
| 5 | 180(M+), 73(999), 71(296), 61(603), 60(826), 57(244), 45(190), 44(196), 43(500), 31(391), 29(293) |
Table 12
Mass spectra of compounds 6–11 of whole plant methanol extract of Calotropis procera (WMECP).
| Compound | m/z (% relative abundance) |
| 6 | 380(M+), 348(280), 97(260), 83(410), 74(500), 69(570), 67(250), 57(350), 55(999), 43(600), 41(650) |
| 7 | 342(M+), 117(534), 103(305), 97(498), 83(999), 75(377), 73(578), 69(550), 57(234), 55(649), 41(168) |
| 8 | 380(M+), 348(280), 97(260), 83(410), 74(500), 69(570), 67(250), 57(350), 55(999), 43(600), 41(650) |
| 9 | 374(M+), 317(184), 185(152), 133(214), 129(202), 117(999), 101(180), 75(400), 73(845), 69(753), 59(207) |
| 10 | 354(M+), 339(437), 145(299), 129(450), 117(634), 75(881), 73(999), 67(257), 55(549), 43(305), 41(404) |
| 11 | 380(M+), 131(461), 130(293), 129(178), 117(584), 116(277), 115(154), 103(350), 75(198), 73(999), 58(146) |
[figure(s) omitted; refer to PDF]
Whole plant n-hexane fraction of Calotropis procera (WHFCP) consists of 9 compounds, for instance, 13-methyltetradec-9-enoic acid methyl ester, 4-methoxy-6-methyl-6.7-dihydro-4H-furo[3,2-c]pyran, propanoic acid. 2,2-dimethyl, 3,cis-(1,1-dimethylethyl)-4,cis-methoxycyclohexanol, 11-fluoroundecan-1-ol, TMS derivative, 3-nonen-1-ol, (Z, 3-methylpentan-1-yl trifluoroacetate, cholest-5-en-3-ol. (3a), and retinal. The chromatogram of whole plant n-hexane fraction of Calotropis procera (WHFCP) is presented in Figure 25. Name, molecular formula, molecular mass, RT, area, and % composition of compounds 1–9 of whole plant n-hexane fraction of Calotropis procera (WHFCP) are shown in Tables 13 and 14. Mass spectra of compounds 1–9 of whole plant n-hexane fraction of Calotropis procera (WHFCP) are shown in Tables 15 and 16. Structures and mass spectra of whole plant n-hexane fraction of Calotropis procera (WHFCP) are shown in Figures 26–41.
[figure(s) omitted; refer to PDF]
Table 13
GC-MS of compounds 1–5 of n-hexane fraction of Calotropis procera.
| Compound | Name | Molecular formula | Molecular mass | RT | Area | % composition |
| 1 | 13-Methyltetradec-9-enoic acid methyl ester | C16H30O2 | 254 | 3.153 | 2197781 | 0.945739463770572 |
| 2 | 4-Methoxy-6-methyl-6.7-dihydro-4H-furo[3,2-c]pyran | C9H12O3 | 168 | 4.989 | 15017268 | 25.8524569440841 |
| 3 | Propanoic acid. 2,2-dimethyl- | C5H10O2 | 102 | 5.599 | 6589.031 | 0.389520015937791 |
| 4 | 3,cis-(1,1-dimethylethyl)-4,cis-methoxycyclohexanol | C11H22O2 | 168 | 6.07 | 24715722 | 10.6355609002819 |
| 5 | 11-Fluoroundecan-1-ol, TMS derivative | C14H31FOSi | 262 | 7.535 | 184247600 | 79.2846177235197 |
Table 14
GC-MS of compounds 6–9 of n-hexane fraction of Calotropis procera.
| Compound | Name | Molecular formula | Molecular mass | RT | Area | % composition |
| 6 | 3-Nonen-1-ol, (Z | C9H18O | 142 | 9.986 | 7863172 | 13.5365710709783 |
| 7 | 3-Methylpentan-1-yl trifluoroacetate | C8H13F3O2 | 198 | 11.697 | 13496.69 | 0.02323476206308 |
| 8 | Cholest-5-en-3-ol. (3a)- | C27H46O | 386 | 13.118 | 549191.188 | 0.236325539099047 |
| 9 | Retinal | C20H28O | 284 | 12.292 | 7806661.5 | 3.35932827740724 |
Table 15
Mass spectra of compounds 1–5 of whole plant n-hexane fraction of Calotropis procera (WHFCP).
| Compound | m/z (% relative abundance) |
| 1 | 254(M+), 96(348), 87(348), 84(399), 83(408), 74(588), 69(910), 67(327), 57(389), 56(700), 55(999) |
| 2 | 168(M+), 124(210), 137(160), 124(210), 109(240), 83(160), 81(160), 69(200), 59(270), 58(999), 55(260) |
| 3 | 102(M+), 87(47), 59(56), 58(44), 57(999), 56(60), 45(38), 41(436), 39(99), 29(292), 27(80) |
| 4 | 186(M+), 97(234), 95(192), 80(354), 72(999), 71(329), 70(235), 69(289), 58(260), 57(648), 55(311) |
| 5 | 262(M+), 107(321), 103(314), 97(598), 83(750), 75(247), 73(460), 69(926), 55(999), 43(300), 41(282) |
Table 16
Mass spectra of compounds 6–9 of whole plant n-hexane fraction of Calotropis procera (WHFCP).
| Compound | m/z (% relative abundance) |
| 6 | 142(M+), 95(407), 82(454), 81(707), 69(601), 68(779), 67(683), 57(327), 55(999), 54(466), 41(736) |
| 7 | 198(M+), 85(118), 84(262), 69(999), 57(623), 56(352), 55(799), 43(203), 41(480), 39(117), 29(206)s |
| 8 | 386(M+,962), 368(755), 275(414), 107(427), 95(449), 81(465), 69(491), 71(609), 57(999), 55(641) |
| 9 | 284(M+), 119(690), 109(570), 105(730), 95(860), 91(999), 81(550), 79(530) 77(530), 69(730), 55(670) |
[figure(s) omitted; refer to PDF]
Whole plant aqueous fraction of Calotropis procera (WAFCP) consists of 7 compounds such as 1-(1-butynyl)cyclopentanol, eicosyl heptyl ether, 1,2-trans-1,5-trans-2,5-dihydroxy-4-methyl-1-(-1-hydroxy-1-isopropyl) cyclohex-3-ene, 3-methyl-2(2-oxopropyl)furan, oleic acid, 5,5-dimethyl-cyclohex-3-en-1-ol, and 1H-imidazole, 1-(-1 oxopentyl). A chromatogram of the whole plant aqueous fraction of Calotropis procera (WAFCP) is presented in Figure 42. Name molecular formula, molecular mass, RT, area, and % composition of compounds 1–7 of whole plant aqueous fraction of Calotropis procera (WAFCP) are shown in Table 17. Mass spectra of compounds 1–7 of whole plant aqueous fraction of Calotropis procera (WAFCP) are shown in Table 18. Structures and mass spectra of whole plant aqueous fraction of Calotropis procera (WAFCP) are shown in Figures 43–56.
[figure(s) omitted; refer to PDF]
Table 17
GC-MS of compounds 1–7 of aqueous fraction of Calotropis procera.
| Compound | Name | Molecular formula | Molecular mass | RT | Area | % composition |
| 1 | 1-(1-Butynyl)cyclopentanol | C9H14O | 138 | 3.829 | 15017268 | 9.72796890337357 |
| 2 | Eicosyl heptyl ether | C27H56O | 396 | 3.574 | 5650818 | 9.72796890337357 |
| 3 | 1,2-trans-1,5-trans-2,5-dihydroxy-4-methyl-1-(-1-hydroxy-1-isopropyl) cyclohex-3-ene | C10H18O3 | 186 | 6.22 | 2676.132 | 0.00460700223947 |
| 4 | 3-Methyl-2(2-oxopropyl)furan | C8H10O2 | 138 | 6.78 | 8543020 | 14.7069398190436 |
| 5 | Oleic acid | C18H34O2 | 282 | 8.501 | 10011715 | 17.2353207636663 |
| 6 | 5,5-Dimethyl-cyclohex-3-en-1-ol | C8H14O | 126 | 13.935 | 136.373 | 0.00023476820889 |
| 7 | 1H-Imidazole, 1-(-1 oxopentyl) | C8H12N2O3 | 152 | 13.973 | 921.289 | 0.00158601312872 |
Table 18
Mass spectra of compounds 1–7 of whole plant aqueous fraction of Calotropis procera (WAFCP).
| Compound | m/z (% relative abundance) |
| 1 | 138(M+), 109(999), 95(454), 81(568), 79(297), 67(511), 55(397), 53(433), 41(354), 39(379), 27(402) |
| 2 | 396(M+), 99(193), 97(263), 85(168), 83(239), 71(253), 70(205), 69(235), 57(999), 55(243), 43(300) |
| 3 | 186(M+), 110(420), 109(470), 95(940), 81(270), 71(999), 70(860), 69(500), 67(310), 59(950), 55(350) |
| 4 | 138(M+), 109(240), 95(450), 71(450), 70(250), 69(680), 67(230), 65(210), 57(999), 56(260), 55(770) |
| 5 | 282(M+), 83(299), 69(425), 67(253), 57(241),55(824), 54(254), 43(595), 41(999), 29(504) 27(258), |
| 6 | 126(M+), 93(197), 85(817), 83(578), 82(932), 69(173), 67(767), 57(999), 56(360), 55(890), 53(240) |
| 7 | 152(M+,137), 85(571), 69(809), 68(257), 57(999), 55(246), 41(593), 40(199), 29(413), 27(149) |
[figure(s) omitted; refer to PDF]
4. Conclusion
None of the extract and fractions of Calotropis procera showed antileishmanial activities and had an IC50 above 100. The extract and fractions of Calotropis procera were inactive against bacterial strains. All extracts and fractions of Calotropis procera exhibited no antifungal activities.
All the extracts and fractions of Calotropis procera exhibited significant anticancer activities against the HeLa cell line. Whole plant methanol extract of Calotropis procera (WMECP) inhibited 69.1% of the growth of HeLa cell line with an IC50 value of 3.1 ± 0.4 and whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant and aqueous fraction of Calotropis procera (WAFCP) inhibited 70.2% and 65.2% with IC50 values of 5.0 ± 0.3 and 17.1 ± 1.0. All the extracts and fractions of Calotropis procera exhibited significant anticancer activities against the PC3 cell line. Whole plant methanol extract of Calotropis procera (WMECP) inhibited 70.1% of the growth of the PC3 cell line with an IC50 value of 5.1 ± 0.3 and whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant aqueous fraction of Calotropis procera (WAFCP) inhibited 61.6% and 59.7% of the growth with IC50 values of 3.7 ± 0.5 and 16.4 ± 1.0.
None of the extract and fractions of Calotropis procera showed anticancer activities against the 3T3 cell line. None of the extract and fractions of Calotropis procera showed anti-inflammatory activities. Whole plant methanol extract of Calotropis procera (WMECP) exhibited lethality at the highest concentration, while other fractions, for instance, whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant and aqueous fraction of Calotropis procera (WAFCP) did not exhibit lethality.
GC-MS studies reveal that whole plant methanol extract of Calotropis procera (WMECP) consists of 11 compounds such as 12-methyloctadec-11-enoic acid trimethylsilyl ester, (1S.15S)-bicyclo[13.1.0] hexadecane-2-one, cholest-5-en-3-ol. (3@), melezitose, @-glucose, heptane. 1.7-dibromo, 1-decanol. 9-[(trimethylsilyl)oxy]-, trifluoroacetate, 15- tetracosenoic acid, methyl ester, isosorbide, 2TBDMS derivative, oleic acid, (Z)-TMS derivative, and 3.7.11.15.18-pentaoxa-2, 19-disilaeicosane, 2,2,19.19-tetramethyl.
Whole plant n-hexane fraction of Calotropis procera (WHFCP) contains 9 compounds, for instance, 13-methyltetradec-9-enoic acid methyl ester, 4-methoxy-6-methyl-6.7-dihydro-4H-furo[3,2-c]pyran, propanoic acid. 2,2-dimethyl, 3,cis-(1,1-dimethylethyl)-4,cis-methoxycyclohexanol, 11-fluoroundecan-1-ol, TMS derivative, 3-nonen-1-ol, (Z, 3-methylpentan-1-yl trifluoroacetate, cholest-5-en-3-ol. (3a), and retinal.
Whole plant and an aqueous fraction of Calotropis procera (WAFCP) contains 7 compounds such as 1-(1-butynyl)cyclopentanol, eicosyl heptyl ether, 1,2-trans-1,5-trans-2,5-dihydroxy-4-methyl-1-(-1-hydroxy-1-isopropyl) cyclohex-3-ene, 3-methyl-2(2-oxopropyl)furan, oleic acid, 5,5-dimethyl-cyclohex-3-en-1-ol, and 1H-Imidazole, 1-(-1 oxopentyl).
Acknowledgments
The authors are thankful to Hussain Ebrahim Jamal (HEJ), Research Institute of Chemistry, University of Karachi, Karachi, Pakistan, for providing antibacterial, antifungal, antileishmanial, and MCF-7 cell line facilities and GC-MS analysis and Institute of Biochemistry, University of Balochistan, Quetta, Pakistan, for providing lab facilities for extraction and fractionation. The study was funded by all authors.
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Abstract
Calotropis procera is a medicinal, traditional, and therapeutic plant in Pakistan. In this research study, the biological activities, for instance, anticancer, antileishmanial, antibacterial, antifungal, anti-inflammatory, and brine shrimp lethality assay and GC-MS are studied. MTT assay, antileishmanial bioassay, microplate Alamar Blue assay, agar tube dilution method, oxidative burst assay using chemiluminescence technique, B-hatching techniques, and triple quadrupole acquisition method MS parameters were the methods used for anticancer, antileishmanial, antibacterial, antifungal, anti-inflammatory, brine shrimp lethality assay, and gas chromatography-mass spectrometry. Whole plant methanol extract of Calotropis procera (WMECP) inhibited 69.1% of the growth of HeLa cell line with an IC50 value of 3.1 ± 0.4 and whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant and aqueous fraction of Calotropis procera (WAFCP) inhibited the growth by 70.2% and 65.2% with IC50 values of 5.0 ± 0.3 and 17.1 ± 1.0. Whole plant methanol extract of Calotropis procera (WMECP) inhibited 70.1% of the growth of the PC3 cell line with an IC50 value of 5.1 ± 0.3 and whole plant n-hexane fraction of Calotropis procera (WHFCP) and whole plant aqueous fraction of Calotropis procera (WAFCP) inhibited 61.6% and 59.7% with IC50 values of 3.7 ± 0.5 and 16.4 ± 1.0. None of the extract and fractions of Calotropis procera showed anticancer activities against the 3T3 cell line. None of the extract and fractions of Calotropis procera showed antileishmanial, antibacterial, antifungal, and anti-inflammatory activities. Whole plant methanol extract of Calotropis procera (WMECP) exhibited lethality at the highest concentration while other fractions did not exhibit lethality. GC-MS studies revealed that the whole plant methanol extract of Calotropis procera (WMECP) consists of 11 compounds, whole plant n-hexane fraction of Calotropis procera (WHFCP) consists of 9 compounds, and whole plant aqueous fraction of Calotropis procera (WAFCP) consists of 7 compounds.
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Details
; Muhammad Anwar Panezai 3 ; Akhtar, Basira 4 ; Abdul Manan Kakar 3 ; Akbar, Ali 5
; Kakar, Shahabuddin 6 ; Nisar Ahmed Shahwani 7 ; Khan, Javed 8 ; Nazima Yousaf Khan 3 ; Ghulam Mustafa Khan 9 ; Baloch, Nizam 9 ; Bakht Zareen Rahim 4 ; Hassan, Noor 3
1 Department of Chemistry, University of Turbat, Turbat 92600, Balochistan, Pakistan
2 Discipline of Biochemistry, Department of Natural and Basic Sciences, University of Turbat, Turbat 92600, Balochistan, Pakistan
3 Institute of Biochemistry, University of Balochistan, Quetta 87300, Pakistan
4 Department of Botany, University of Balochistan, Quetta 87300, Pakistan
5 Centre for Biotechnology and Microbiology (CBM) University of Swat, Swat 19130, Khyber Pakhtunkhwa, Pakistan
6 Department of Zoology, University of Balochistan, Quetta 87300, Pakistan
7 Faculty of Pharmacy, University of Balochistan, Quetta 87300, Pakistan
8 Department of Microbiology, Quaid-i-Azam University, Islamabad 45320, Pakistan
9 Department of Chemistry, University of Balochistan, Quetta 87300, Pakistan