Phytoconstituents of Leaves and Roots Ethanolic Extract of Talinum paniculatum and Their Biological Activities

 

Susilo Susilo¹*, Fadita Nurul Aini¹, Etin Diah Permanasari²

¹Department of Biology Education, Universitas Muhammadiyah Prof. Dr. Hamka,

East Jakarta, Indonesia 13830.

²Faculty of Pharmacy and Science, Universitas Muhammadiyah Prof. Dr. Hamka,

East Jakarta, Indonesia 13460.

 

ABSTRACT:

Javanese ginseng (Talinum paniculatum) is known to the people of Indonesia to have properties in medicine and food. People's culture generally uses leaves and roots that, until now, constituent information has yet to bereported. Therefore, variations of phytoconstituents in the leaves and roots of T. paniculatum were investigated using Gas Chromatography-Mass Spectrometry (GC-MS). The roots of T. paniculatum contain 17 active compounds dominated by N,N'-Dibutyl-N,N'-dimethylurea. The leaf has only 16 active compounds, but Python compounds from the diterpenoids class dominate it. In general, T. paniculatum contains a variety of steroid class compounds, namely Stigmasterol; Stigmast-5-en-3-ol; and 9,19-Cycloergost-24(28)-en-3-ol, 4,14-dimethyl-, acetate, (3,β., 4.α., 5.α.) - in the leaves, and stigmasterol and .γ.Sitosterol in the root. Python is known to have high efficacy as an antimicrobial, antifungal, antibacterial, antiparasitic, antimutagenic, and antioxidant. At the same time, steroid compounds are anti-cancer, antioxidant, anti-tumor, antidiabetic, and anti-inflammatory agents. The results of identifying compounds in T. paniculatum can be used as a reference in optimizing the use of T. paniculatumin the future.

 

 

 

INTRODUCTION: 

Ginseng is a herbaceous plant known throughout the world as a medicinal plant. Ginseng has a variety of species, such as Panax ginseng in Korea, Panax notoginseng in China, Panax quinguefolius in America, Pfaffia paniculate in Brazil, Withania somnifera or Ashwagandha in India¹ and Java Ginseng in Indonesia. Pharmacological studies explain different benefits such as Panax ginseng (Korea) used as an anti-cancer and anti-inflammatory², Panax quinguefolius (America) to treat hypoglycemic diseases³, Withania somnifera or Ashwagandha (India) used as an anti-Adipogenic⁴.

 

 

Furthermore, Panax notoginseng, or Chinese Ginseng, is predominantly used for cardiovascular and cerebrovascular treatment⁵. Javanese Ginseng (Talinum paniculatum) is used in medicine and mixed vegetable ingredients in Indonesia. This plant is easy to grow in tropical land and easily adapts to high environments to drought stress, salinity, and low nutrient conditions⁶.

 

T. paniculatum is known to have good antioxidants for the management of cardiovascular diseases⁷, treatment of cancer, diabetes, liver disorders, leishmania, and reproductive disorders⁸, atherosclerosis, hypertension, ischemia/reperfusion injuries, neurodegenerative diseases, inflammation, aging, and dealing with the negative impact of free radicals⁹. Secondary metabolites often found in this plant are tocopherols and phytosterol compounds¹⁰.

 

Tocopherols contain antioxidants and are also reported as anti-cancer in the large intestine. Tocopherol compounds known by the world community are Vitamin E¹¹. Vitamin E is highly effective as a natural antioxidant from plants¹². Plant Tocopherols often move with phytosterol compounds¹¹. Phytosterols and stigmasterols are widespread in every food and are efficacious in anti-inflammatory and antioxidant properties¹³. Phytosterols' ability to lower cholesterol is also closely related to preventing cardiovascular disease and diabetes¹⁰. Triterpenoids and diterpenoids are a class of compounds that often dominate in some plants¹⁴. Triterpenoid compounds are reported to have anti-cancer, anti-diabetic, and anti-inflammatory propertiesand neuroprotective activity¹⁵. Similarly, diterpenoids have many benefits, such as antibacterial, antimicrobial, antioxidant, anti-cancer, and anti-inflammatory¹⁶.

 

The use of ginseng as a medicinal plant in Indonesia has been known for a long time, especially for Chinese people who have used ginseng roots fordecades. However, these two parts' compounds are rarely reported in detail. Using Gas Chromatography-Mass Spectrometry (GC-MS), this study aimed to explore the active compounds in the leaves and roots of T. paniculatum. The identified active compound data are helpful as a reference in optimizing the utilization of T. paniculatum leaves and roots in the future.

 

MATERIALS AND METHODS:

Plant Material:

Talinum paniculatum was collected from Bogor Regency, Java Island, Indonesia farmers. The plants were identified by Herbarium Bogoriensis BRIN, Indonesia, and deposited in the university database with identification number 3079-46085-2.

 

Sample Preparation:

Young leaves and roots of T. paniculatum are separated and washed using running aquadest water. Every 100g of fresh leaves and roots are oven-dried for 72 hours at 50^oC¹⁴. Each dry sample was mashed with a grinder to powder (60 mesh) and then macerated using Ethanol P.A. (99.8%) for five days. A total of 10ml of each sample extract was put into different tubes and dried at 60^oC using the Rotary¹⁷.

 

GC-MS Analysis:

GC-MS Agilent Technologies 7890 with Mass Selective Detector and Chemstation machines were used for phytochemical analysis following previous research procedures¹⁰. The ethanol extract was filtered through a syringe filter of 5μL in split mode (8:1) with helium-carrying gas¹⁸. The initial oven temperature of 80°C was set and raised by 3°C/min to 150°C.  After being held for 1minute, the temperature setting was raised by 20°C/min to 280°C, and at peak temperature, it was held for 25 minutes.

Data Analysis:

Agilent MassHunter Software was used to identify active compounds by comparing mass fragments with standard mass spectra. Data on bioactivity have been analyzed using PubChem, Chemistry WebBook (NIST), SpectraBase, and FOODB (TMIC) libraries. The library was also used in Guang-Mei Tang's research¹⁹.

 

RESULTS:

GC-MS analysis showed that the two T. paniculatum samples had different compound variations and quantities. The output of GC-MS analysis in a chromatogram (Figure 1) is used to analyze the names of compounds present. Sixteen active compounds were identified in the leaves (Table 1), with phytol compounds occurring in number and overwhelmingly predominating (31.65%). In contrast, the root contains 17 active compounds with content that does not look much different.

 

Figure 1: Chromatogram of T. paniculatum leaves and roots from GC-MS

 

The present Retention Time (R.T.) describes of discovery compounds during process in GC-MS ¹⁴. The chemical library identified 16 compounds in leaf organs (Table 1) and 14 compounds in root organs (Table 2). Only 1 compound in the root organ for which no compound identity data was found. In contrast to the Class of Compounds identified from SpectraBase and FOODB.

 

 

Table 1: Phytochemical components in the leaves of Talinum paniculatum

No	Metabolites Compound	R.T.	Quality	% of Area	M.F.	M.W. (g/mol)	Library	Class of Compound
1	2-Butyloctanoic acid	28.30	25	1,09	C12H24O2	200,322	NCBI	Fatty acyls: Octanoic acid
2	Phytol	29.40	90	31,65	C20H40O	296,539	NCBI	Prenol lipids: Acyclic diterpenoids
3	1,3-Propanediamine, N-(3-aminopropyl)-N-methyl-	31.07	50	3,01	C7H19N3	145.2	NIST	Organonitrogen compounds: Dialkylamines
4	Oleoylchloride	31.54	56.	9,98	C18H33ClO	300,91	NCBI	Unknown
5	5-Methyl-6-phenyltetrahydro-1,3-oxazine-2-thione	31.85	49	3,96	C11H13NOS	207,29	NCBI	Benzene and substituted dervatives
6	1,1,1,4-Tetrachloro-4,4-divinyldisilethylene	32.51	35	10,98	C6H10Cl4Si2	280.10	NCBI	Unknown
7	2,6,10,14,18,22-Tetracosahexaene, 2,6,10,15,19,23-hexamethyl-, (all-E)-	32.81	99	6,16	C30H50	410,73	NCBI	Prenol lipids: Triterpenoids
8	5-Butyl-6-hexyloctahydro-1h-indene	34.09	41	1,17	C19H36	264.497	NCBI	Fluorenes: Polycyclic hydrocarbons
9	2,7,8-Trimethyl-2-(4,8,12-Trimethyltridecyl)-6-chromanol	35.02	95	1,81	C28H48O2	416,69	NCBI	Prenol lipids: Tocopherols
10	VitaminE	35.87	99	14,84	C29H50O2	430.717	NCBI	Prenol lipids: Tocopherols
11	Stigmasterol	37.84	93	8,64	C29H48O	412,702	NCBI	Steroids: Stigmastanes and derivatives
12	Stigmast-5-en-3-ol	38.82	99	5,52	C29H50O	414.718	NCBI	Steroids: Stigmastanes and derivatives
13	9,19-Cycloergost-24(28)-en-3-ol,4,14-dimethyl-,acetate, (3.β., 4.α., 5.α.)-	39.02	87	4,09	C32H52O2	468,766	NCBI	Steroids: Cycloartanols and derivatives
14	Cholest-2-en-2-ylmethanol	39.89	46	1,15	C28H48O	400.70	NCBI	Unknown
15	Cyclopropane carboxamide,2-cyclopropyl-2-methyl-N-{1-cyclopropyethyl)-	40.22	45	1,68	C13H21NO	207.31	NCBI	Cyclopropanecarboxylic acids and derivatives
16	dl-.α.-Tocopherol	41.62	60	2,14	C29H50O2	430.717	NCBI	Prenol lipids: Tocopherols

 

 

Table 2: Phytochemical components in the leaves of Talinum paniculatum

No	Metabolites Compound	R.T.	Quality	% of Area	M.F.	M.W.	Library	Class of Compound
1	Butane-1,4-d2	6.45	50	1,20	C4H8D2	60.14	WILEY	Saturated hydrocarbons: Alkanes
2	N,N'-Dibutyl-N,N'-dimethylurea	25.88	43	21,11	C11H24N2O	200.18	WILEY	Ureas
3	Hexadecanoic acid,ethylester	28.51	99	17,91	C18H36O2	284.484	NCBI	Fatty acyls: Fatty acid esters
4	1,5-Anhydro-d-mannitol	28.80	38.	16,24	C6H12O5	164.16	NCBI	Organooxygen compounds: Monosaccharides
5	Hexadecanoic acid	29.19	45	2,56	C16H32O2	256,43	NIST	Fatty acyls: Long-chain fatty acids
6	Ethyl (9z,12z)-9,12-octadecadienoate	29.57	99	11,46	C20H36O2	308,50	WILEY	Fatty acyls: Lineolic acids and derivatives
7	Hexadecanoic acid, ethyl ester	29.71	97	1,78	C18H36O2	284.484	NCBI	Fatty acyls: Fatty acid esters
8	(9e,12e)-9,12-Octadecadienoic acid)	29.85	91	3,63	C18H32O2	280.452	NCBI	Fatty acyls: Lineolic acids and derivatives
9	2-Aminoethanethiol hydrogen sulfate (ester)	30.15	92	l,24	C2H7NO3S2	157,20	NCBI	S-alkyl thiosulfates
10	n,6-Dimethyl-5-hepten-2-amine	30.99	52	1,42	C9H19N	141,2539	NCBI	Fatty acyls
11	13-Octadecenal,(Z)-	31.54	74	1,31	C18H34O	266.46	NCBI	Fatty aldehydes
12	2-Aminoethanethiol hydrogen sulfate (ester)	31.64	53	1,43	C2H7NO3S2	157,20	NCBI	S-alkyl thiosulfates
13	Z,Z-10,12, Hexadecadien-1-ol acetate	32.44	93	3,74	C18H32O2	280.40	NCBI	Fatty acyls: Long-chain fatty acids
14	7-Isopropyl-4a-methyloctahydro-2 (1h)-naphthalenone	32.87	91	1,94	C14H24O	208.34	NCBI	Cyclic ketones
15	Stigmasterol	37.82	99	4,92	C29H48O	412,702	NCBI	Steroids: Stigmastanes and derivatives
16	γ. - Sitosterol	38.78	99	2,26	C29H50O	414.70	NCBI	Steroids: Stigmastanes and derivatives
17	Methyl 3-hydroxyolen-18-en-oate	44.13	93	2,68	Unknown	Unknown	Unknown	Unknown

T. paniculatum leaves are dominated by active compounds from the prenol lipids class, specifically the Acyclic Diterpenoids subclass. In contrast, the Urea class dominated the roots with active compounds called urea, N, N'-dibutyl-N, N'- dimethyl- (21.11%). Naturally, the roots of T. paniculatum contain alkaline Urea compounds that can be found in all living things. Urea is helpful in several enzymatic reactions in the human body. In addition, only Stigmasterol compounds are found in both parts. Stigmasterol comes from the Steroid class with subclass Stigmastanes. This compound was often found in fruits and vegetables (TMIC).

 

DISCUSSION:

The organic solvent used in the study was used ethanol (C₂H₆O) which could remove fat components. Ethanol is a straight-chain primary alcohol²¹ with anM.V. of 46.07 g/mol, safe for research activities but harmful to body health, especially if ingested²². The use of ethanol is also growing, such as in photosynthetic activities²³, antioxidant defense²⁴, defense from abiotic stress, and dissolution of curcumin compounds to overcome health problems²⁵. This study chose an ethanol content of 99.8% as the solvent.Ethanol can extract several compounds and is approved in the food industry through proper processing²⁶ because it includes non-toxic and food-grade solvents²⁷.

 

T. paniculatum leaves are utilized in traditional medicine in Indonesia²⁸, with the leaves as the most commonly consumed organ in many parts of South America, Africa, and Asia⁸. T. paniculatum leaves contain phytol (C₂₀H₄₀O) as the most compound by 31.65%. Python belongs to the group of diterpenoids²⁹, with a pungent sweet aroma²⁹. Python is beneficial as a powerful antimicrobial³⁰, antifungal^31,32, antibacterial, antiparasitic, antimutagenic, antioxidant, and            cytotoxic ³², and widespread on plant bodies such as Populus plants³³, Ocimum spp.³², C. tamariscifolia, C. sedoides³⁴, Propophyllum linaria, Vitex negundo, Rhaponticum acaule, and Apiumnodflorum³¹. Python can act as a precursor of vitamin E in plants³⁴, as well as the main component of A. nodiflorum essential oil in treating yeast, dermatophytes, and Aspergillus spp³¹.

 

The root part of the ginseng group plant can be called the body part of the plant of high economic value³⁵. The 100-year-old ginseng root is thought to have many benefits and can treat rare diseases because it contains precious active compounds. T. paniculatum root has many beneficial active compounds⁸ and is often used in prescription drugs  with an ideal age of 3-4 years³⁶. The roots of T. paniculatum studied are young, but GC-MS analysis has found seventeen active compounds beneficial to the human body. This shows that the roots of T. paniculatum already have extraordinary benefits even though they are still young. Especially with the content of 1,5-Anhydro-d-mannitol as a precursor of gluconeogenesis so that it acts as an antidiabetic (SCBT) and Hexadecanoic acid as an anti-inflammatory and antioxidant³⁸. The biological activity of other active compound components is described in Table 3.

 

Table 3: Biological activities of active compounds in T. paniculatum identified

No	Metabolite of Compound	Biology Activities
1	(9e,12e)-9,12-Octadecadienoic acid)	Anti-cancer 39
2	γ. - Sitosterol	Anti-cancer 40
3	1,3-Propanediamine, N-(3- aminopropyl)-N-methyl-	Anti-cancer 41
4	1,5-Anhydro-d-mannitol	Anhydrohexitol derivatives 42 as antivirals and gluconeogenesis inhibitors (SCBT)
5	13-Octadecenal, (Z)-	Sex pheromones 43
6	2,6,10,14,18,22-Tetracosahexaene, 2,6,10,15,19,23-hexamethyl-, (all- E)-	Antioxidant, anti-cancer44, protects the liver, fights fatigue, strengthens the immune system, and increases human immunity 45
7	2,7,8-Trimethyl-2-(4,8,12-Trimethyltridecyl)-6-chromanol	Antioxidant 46
8	2-Aminoethanethiol hydrogen sulfate (ester)	Antioxidant, anticancer 47
9	2-Butyloctanoic acid	Anticovulsant48, antimicrobial (JII)
10	5-Butyl-6-hexyloctahydro-1h-indene	Spesies aromatic 50
11	5-Methyl-6-phenyltetrahydro-1,3- oxazine-2-thione	Insecticide, larvicide, pesticide (TMIC)
12	9,19-Cycloergost-24 (28)-en-3-ol, 4,14-dimethyl-, acetate, (3.β., 4.α., 5.α.) -	Antibacterial, anti-staphylococcus, pesticide (TMIC)
13	Butane-1,4-d2	Anticarcinogenic, anti cancer 51
14	dl-.α.-Tocopherol	Antioxidant52.
15	Ethyl (9z,12z)-9,12-octadecadienoate	Antioxidant 53, anti-inflammatory 54
16	Hexadecanoic acid	Anti-inflamasi, antioxidant 55
17	Hexadecanoic acid, ethyl ester	Anti-inflammatory, antioxidant, anti-cancer, and antimicrobial 53
18	Phytol	Antimicrobial, antifungal, antibacterial, antiparasitic, antimutagenic, antioxidant 32
19	Stigmast-5-en-3-ol	Antioxidant, anti-cancer(TMIC)
20	Stigmasterol	Anti-inflammatory56, antidiabetic57, anti-tumor +
21	Vitamin E	Antioxidant 59

 

Our results found nine components of active compounds that were not reported regarding their biological activity (Table 4).

 

Table 4: The active compound of T. paniculatum, whose biological activity is not identified

No	Metabolite of Compound	Biology Activities
1	1,1,1,4-Tetrachloro-4,4- divinyldisilethylene	Unknown
2	7-Isopropyl-4a-methyloctahydro-2 (1h)-naphthalenone	Unknown
3	Cholest-2-en-2-ylmethanol	Unknown
4	Cyclopropane carboxamide, 2-cyclopropyl-2-methyl-N-{1-cyclopropyethyl) -	Unknown
5	Methyl 3-hydroxyolen-18-en-oate	Unknown
6	n,6-Dimethyl-5-hepten-2-amine	Unknown
7	Oleoyl chloride	Unknown
8	Urea, N,N'-dibutyl-N,N'- dimethyl-	Unknown
9	Z,Z-10,12, Hexadecadien-1-ol acetate	Unknown

 

GC-MS analysis also succeeded in finding sterols produced by plants known as phytosterols  with various mixtures of compounds related to plant functions, with abundant amounts⁶⁰. Phytosterols have been further developed for the human body, which cannot synthesize phytosterols⁶¹. Phytosterols reduce cholesterol to overcome cardiovascular disease and anti-cancer. The group of phytosterols that are often found in various plant species are stigmasterols and -sitosterols such as γ-sitosterol^62,63 in canola, sesame, and legumes⁶⁴, sorghum seeds⁶⁵, and Eruca sativa Mill⁶⁶.

 

Through GC-MS analysis, 8.64% Stigmasterol was found in the leaves and 4.92% in the roots of T. paniculatum. Stigmasterol belongs to the sterol group⁶⁷ with the primary function of maintaining the shape of the cell membrane and can be used as an oleogelator which leads to the formation of lipid structures in plant organelles⁶⁸. For the human body, stigmasterol acts as an anti-inflammatory⁶⁹, and anti-diabetic⁷⁰ by lowering blood cholesterol levels⁷¹. Stigmasterol acts as an anti-tumor⁵⁸, capable of apoptotic ovarian cancer cells through induction of the endoplasmic reticulum and mitochondrial dysfunction and even able to overcome endometrial cancer cells⁷². Phytosterol derivative compounds named 9,19-Cycloergost-24 (28)-en-3-ol, 4,14-dimethyl-, acetate, (3.β., 4.α., 5.α.)- are also found in T. paniculatum leaves. This cycloartenol ring steroid compound is found in various plants, such as corn, cucumber, peppers, pepper, spinach, and avocado. The biological activity of this compound has never been reported in the literature. However, TMIC reported that this compound could act as an antibacterial, anti-staphylococcus, and pesticide. GC-MS analysis also found a phytosterol compound in the form of .γ.-Sitosterol (C₂₉H₅₀O), which is cytotoxic to cancer cells in the colon and liver⁴⁰.

 

In this study, the discovery of very valuable sterols, namely stigmasterol and γ sitosterol. This is similar to research on T. paniculatum in Brazil, which contains stigmasterol and sitosterol, valuable chemical compounds⁷³. Even the discovery of phytol compounds from the leaves of T. paniculatum, which is famous for its abundant properties. Therefore, we believe that the abundant metabolite content of T. paniculatum is a strong reason for its consumption as a medicinal ingredient, such as in Indonesia^74–76, Brazil⁷, China⁸, and Peru⁷⁷.

 

CONCLUSION:

T. paniculatum is an ingredient in traditional medicine in various regions because it is believed to have the same benefits as ginseng species from other groups. The leaf part of T. paniculatum is most often used. It differs from the stem because it is rarely studied, and the roots of T. paniculatum are more often used when they are adults. However, GC-MS analysis found 16 active compounds in the leaves and 17 active compounds in the roots. Biological activity is based on international libraries and found that T. paniculatum in Indonesia has very beneficial properties. T. paniculatum contains plant sterols (phytosterols), mainly in the form of stigmasterol and γ sitosterol. This study proves that the leaves and roots of T. paniculatum have high health value and can be used as medicinal ingredients.

 

ACKNOWLEDGMENTS:

The author would like to thank the ELSA Botanical Identification Services (Herbarium Bogoriense), Indonesia.

 

FUNDING:

This research supported by UHAMKA Charity with grand number 756/F.01.03/2022.

 

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Accepted on 09.11.2023           © RJPT All right reserved

Research J. Pharm. and Tech 2024; 17(2):679-685.