REVIEW ON LUPEOL – A TRITERPENOID
HTML Full TextREVIEW ON LUPEOL - A TRITERPENOID
Poonam Lal *, Vaidehi Kale and Sanket Mendhe
Department of Pharmaceutical Sciences, P. R. Pote Patil College of Pharmacy, Amravati, Maharashtra, India.
ABSTRACT: Lupeol, a pent acyclic triterpenoid known as secondary metabolites. Chemically it is a 20(29)-Lupen-3-beta-ol derived from eggplant. The main part of this plant is steam & bark. It is obtained from vegetables, fruits & medicinal plants. The isolation of Lupeol was done by TLC monitoring column chromatography by using solvents like hexane & ethyl acetate on the basis of adsorption principal. The species of Lupeol such as S. xanthocarpum which have specifically anti diabetic action & many other species which have a dynamic and diverse effects. The doses of Lupeol vary from disease to disease and it can be administered in-vitro & in-vivo technique like intra-peritoneal, intramuscular, oral, topical. On the basis of many researches’, Lupeol shows a magical activity toward various types of diseases with less side effects & have a good ability to cross blood brain barrier.
Keywords: Lupeol, Triterpenes, Anti-inflammatory, Anti-cancer, Anti-diabetics, Cardio-protective, Skin-protective, Nephero-protective, Hepato-protective
INTRODUCTION: Eggplant with yellow fruits has been an important medicinal product since ancient times. Lupeol (20(29)-Lupen-3 betaol), which is the main active ingredient of the steam bark of S. xanthocarpum, has been reported to have many activities such as, anti-inflammatory, antihyperglycemic, antilipemic abnormalities & antimutagenic effects 1. These reports have been found in various animal models or diseases in which Lupeol has anti-diabetic, anti-asthma, anti-arthritis, cardioprotective, hepatoprotective, renal protective and anti-preventive disease, intraperitoneally and intravenously. Lupeol belongs to the pentacyclic found lupine type triterpenoids in food, fruit and many plants.
Triterpenoids are called secondary metabolites and their active substances are derived from plants, fruits, fungi, etc. Natural triterpenoids, commonly referred to as secondary metabolites, are of interest 2. Due to their extensive biological activities, triterpenoids are a widely used class of compounds containing important compounds. The pharmacological significance of the gift of a healthy life comes from medicinal herbs. Over 8,000 different plant species are employed to treat various diseases in different parts of the world. Biosynthetic rearrangements of squalene epoxides lead to the synthesis of various triterpenoids.
Hydrocarbon triterpene derivatives can be obtained by various processes such as oxidation, hydrogenation and dehydrogenation 3. Lupeol, Lupine triterpene nutrition, triterpene is naturally found in various plants called Lupeol. Although people in the Western world consume about 250 mg of triterpenoids day by day, it's worth nothing that in Mediterranen countries where most foods are dominated by olive oil, the average triterpenoid intake a person consume will reach 400 mg/day 4. Lupeol is a triterpene that has attracted doctors, scientists and pharmaceutical manufacturers for its many medicinal activities. The major triterpene business is now marketed worldwide. It is estimated that more than 2,400 subjects participated in clinical trials of various types of triterpenoids at doses of 25 grams or more per day and there were no adverse outcomes. It has attracted the attention of doctors, drug dealers and scientists, and is known all over the world for its various medical activities 5.
FIG. 1: 5
FIG. 2: 6
Sources of Lupeol: Numerous plant species are said to contain Lupeol in various forms. Genuine Lupeol is establishing in many plants such as mango, acacia, and velvet acacia. Lupeol is found in vegetables and fruits such as cabbage, peppers, cucumbers and tomatoes. Examples consist of olives, figs, mangoes, strawberries, red berries, and herbs such as American ginseng, shea butter herb, tamarind, Allanblackia monticola, Himatanthus sucuuba, Celastrus papulatus, Zanthoxylum riedelianum, Leptadenia hastadenokalta, Crataapatoria seed, and Eleptadeniahastaden. Native to North America, Latin America, Japan, China, Africa and the Caribbean islands 3.
TABLE 1: LIST OF SELECTED PLANT CONTAINING LUPEOL 3
Botanical name | Habitual name |
Aloe vera | aloe |
Daucus carota | carrot |
Glycine max | soya bean |
Olea europa | olive |
Lycopersicon esculentwn | tomato |
Lawsonia inermis | henna |
Apocynum cannabinum | bitterroot |
TABLE 2: CONTENT OF LUPEOL IN FRUIT AND IN PLANT 3
Name of plant | Lupeol (µg/g) |
Olive fruit | 3 µg/g of fruit |
Mango fruit | 1.80 µg/g mango pulp |
Aloe leaves | 280 µg/g dry leaf |
Japanese pear (shinko) | 175 µg/g twig bark |
Ginseng oil | 15.2 µg/g of oil |
Eim plant | 880 µg/g of bark |
Chemistry of Lupeol: The chemical formula of Lupeol is C30H50O and its melting point is 215-216 °C. The product calculated from the formula of Lupeol, indicates a molecular weight of 426.7174 [g/mol], H-B donor 1, H-B acceptor 1.
Infrared spectrum Lupeol was found to have hydroxyl functional groups and olefinic moieties, showing that they appear in the 3235 and 1640 cm-1 19.
The existence of seven methyl singlet and olefinic functional groups in the 1H-NMR spectrum indicates that Lupeol is an important pentacyclic triterpenoid 409.12 20.
In the LR IR spectrum of Lupeol alcohol, a strong wide band at 3384 cm and intermediate densities at 1192 cm and the O-H bond quivering of the hydroxyl category at 672 cm are found in the band and outside the C-H plane, negligible vibration is detect at 826 cm.
The correlate with C=C vibration appears as a weak band around 1654 cm. Flexural and bending vibrations of the methyl part can be seen in the density band 2916 cm-1 & in the half-density band at 1460 cm-1 8. Formula defines the presence of 6° unsaturation, which is evident from the olefinic activity 4.
The chemical structure of Lupeol is as follow:
STRUCTURE OF LUPEOL 8
MS SPECTRUM OF LUPEOL 31
IR SPECTRUM OF LUPEOL 32
Isolation of Lupeol:
Extraction: Weigh 500 g of crushed stems within a scrubbed Winchester bottle, add 1.5 liters of hexane & shake periodical at that time strain later than 48 hours, repeat for ethyl acetate.
Concentrate in vacuum at around 42 °C using a field evaporator for one-third of its original product to yield 1.2 g (0.24%) primitive n-hexane take out.
2g (0.24%) primitive ethyl acetate take out & 2.5g (0.5%) methanol take out. These were subsequently used in bioassay research & following isolation, several spectroscopic analyzes of isolated V39 were performed 8.
Separation and Purification: Coniferous tree extracts in hexane & ethyl acetate were dissolved in a minimum 9:1 ethyl acetate to hexane weight system, pre-absorbed in-silica gel, and then put onto a silica gel column. When using gradient elution with multiple hexane-ethyl acetate solvents, normal phase adsorption chromatography (10.0, 9.5: 0.5, 9.5). 0:1, 8, 5:1, 5, 8, 0:2. 0, 7, 5:2, 5, 7, 5:3, 5, 6, 0:4, 0, 5: 5: 4. 5, 5.0: 5.0) in ascending order of polarity. A 9: the basis for TLC monitoring in column chromatography was the 1 body weight ratio, which allowed TLC to compare with the hexane/ethyl acetate (9:1) weight method while simultaneously isolating V39.
This substance, designated V39, was observed as a white needle-like crystal & underwent a number of spectrum analyses 8.
Biosynthesis of Lupeol: Triterpene synthases in plants control the manufacture of Lupeol, which is one of the most intricate substances discovered in nature. Mevalonate (MVA), isopentenyl pyrophosphate (IPP), dimethyl allyl pyrophosphate (DMAPP), & fusyl pyrophosphate (FPP) are all involved in the slow cytoplasmic production of Lupeol. FPS, or farnesyl pyrophosphate synthase, catalyzes this process. Squalene synthase (SQS) then transforms FPP into squalene. Squalene 2, 3 oxysqualene is oxidized by squalene epoxidase (SQE), which is then converted into lupinyl cations by Lupeol synthase (LUS). Finally, deprotonation of the 29-methyl group transforms the lupinyl cation into Lupeol 9.
Lupeol shows many pharmacological activities which are listed as follow:
- Anti-inflammatory action
- Anti-cancer activity
- Skin protective
- Anti diabetics
- Cardio protective
- Hepato protective
- Nephero protective
- Biological activity of Lupeol on humans
Anti- Inflammatory Action of Lupeol: Some studies using wear & tear models possess appear certain the anti-inflammatory effect of Lupeol is better than that of indomethacin. Comparative studies in mouse models have gained deeper understanding (a non- steroidal anti-inflammatory drug). Lupeol is widely recognized being its constraints result in-vitro & in acute imitation. Lupeol pretreatment may delay the immunological effect of Lupeol as it shortens prostaglandin E2 (PGE2) assembly in A23187-bracing macrophages. The anti-inflammatory demeanor of the Lupeol well endowed abstract was agnate to that apparent by the careful cyclo-oxygenase constraints 1. Lupeol analysis (5–9.37 mg/kg) was appear to display anti-inflammatory action accompanied by a best reticence of 57.14% spell as α-mangostin at agnate dosage be visible anti-inflammatory action of 38.70%. Lupeol & its by products (linoleate, acetate and palmitate) were apparent to display college anti-inflammatory action than frequently acclimated non-steroidal anti-inflammatory biologic indomethacin in rat & abrasion imitation of inflammation 12. The anti-inflammatory after product of Lupeol was empiric to be according to dexamethasone, a able-bodied accepted anti-inflammatory agent. Lupeol has anti-inflammatory properties and can be operated to control colitis and heal the intestines 11. Lupeol is a common triterpene operated to shorten the inflammatory response & has immunomodulatory attribution 12.
Anti- Cancer Action of Lupeol: The available abstraction of Lupeol is appearing as anticancer act venture. Lupeol has been abeyant to perform adjoin altered types of cancers such as animal prostate, breast blight skin, liver, & claret cancer. Lupeol is appearing to display able anti-mutagenic action back activated beneath in-vitro & in-vivo conditions. Cancer is an all-encompassing appellation that comprises an ample cardinal of diseases that condition detectable genitalia of the animal body. Principal blight types that acquired added expired in 2012 were lung (1.59 million), alarmist (745,000), belly (723,000), rectal cancer (694,000), & breast blight (521,000).
Even admitting there are abounding treatments to altered blight types (i.e. surgery, chemotherapy, radiation therapy, targeted analysis & immunotherapy), these treatments accept apparent abounding accessory furnishings on patients. We previously found that Lupeol inhibited the development of carcinogenesis in the bark of two jujube trees in an abrasion model. We also displayed that the Lupeol assay (40 mg/kg) inhibited prostate cancer tumor growth in animal inducers in a allograft wearing imitation .We additionally displayed that Lupeol analysis (40 mg/kg) hamper the advance of prostate cancer tumors of animal abettor built-in a allograft abrasion imitation. Studies with assorted blight beef accept apparent that Lupeol embrace multifaceted action to arrest the advance of animal cancer beef & by prompt apoptosis. Rectal cancer blight (CRC) is the capital of patient's life after metastasis (CRC) 8. The effects of Lupeol treatment on HCT116 and SW620 rectal cancer cells & inhibition of rectal cancer cells through inhibition of the cytoskeletal RhoA-ROCK1 pathway provide metastatic protection to cancer patients 11.
Skin Protective Action of Lupeol: The bark careful furnishings of Lupeol were empiric to be analogous with its abeyant to magnify the bark anti-oxidant arrangement. A abstraction put into practice an in vitro archetypal of beastly bark keratinocytes (epidermal explants) able at Air liquid associated studies on de-epidermis removed animal skin to examine the transfer of Lupeol to the skin, inflammation caused by tissue damage, & soft tissue growth, Corrosion ion carcinogenesis in the prostate & pancreatic blight, Lupeol showed a strong inhibitory effect on the prostate Fusarium wil Supplementary beef & evaluation of 21 also showed a strong anti-tumor effect in two 22-day skin models. Lupeol provides able antioxidant aegis adjoin benzoyl peroxide-promote deadly in Swiss albino abrasion bark diminished the PGE2 assembly & reticence the assembly of TNF ά and interleukin-Ib in-vitro.
The after-effects advance the antitoxin furnishings of Lupeol on DMBA promote DNA alkylation accident in Swiss bleached cowards an excision, cavity & asleep amplitude anguish beastly archetypal is a able bodied activated archetypal to abstraction anguish healing and associated mechanisms .It is an effective chemo preventive drug against skin toxicity 14. Recent news indicates that many Lupeol-based anti-aging & anti-fungal peel creams are in improvement. Lupeol is an interesting drug used to improve the appearance of the skin & eliminate fungal infections 13, 14.
Anti-Diabetic Action of Lupeol: Diabetes mellitus frequently accepted as diabetes and an accumulation of metabolic affection that causes aerial claret amoroso akin beyond an abiding interval. There are two types of diabetes, type 1 & type 2. Lupeol appears to have anti-inflammatory properties. Many studies have shown that Lupeol has anti-hyperglycemic properties & its consumption may reduce the prospect of diabetes in animal imitation. Protein tyrosine phosphatase 1B (PTP1B) plays the above function inhibiting insulin activity 10. Many researchers have demonstrated the effectiveness of Lupeol in ameliorating diabetes using diabetes models because the effects of Lupeol are achieved by eliminating carbohydrate assimilation in the intestine. Lupeol has activity similar to metformin and alters antioxidant enzymes 15. Lupeol plant ingredient from Solanum nigrum prevents diabetes succeeding 21 days 16. Lupeol additionally reduced glycated hemoglobin, serum glucose, and nitric oxide. Plants abstract of Lupeol reticence the claret glucose levels in streptozotocin (STZ)-induced diabetic rats 17. Lupeol is also used for the analysis of diabetes which reticence the alpha-glycosidase activity 18. Lupeol also reduces glycated hemoglobin, serum glucose, & nitric oxide 16.
Cardio-Protective Action of Lupeol: Lupeol antiquated advised for its cardioprotective abeyant in beastly accepting cyclophosphamide, a biologic acclimated in the analysis of blight and autoimmune disorders. Cyclophosphamide analysis (200 mg/kg for 10 days) was appear to decidedly abatement the action of ATPases & adapt the extend of urea, uric acerbic & creatinine in serum & urine of animals 19, 20. Yet, Lupeol (50 mg/kg for 10 days) analysis was apparent to allow aegis adjoin cyclophosphamide-prompt cardiotoxicity in these mice 21, 22.
Hypercholesterolemia is appear to account astringent adulterated of the cardio-vascular arrangement Lupeol has been shown to have an anti-hypercholesterolemia effect in the first rat model of hypercholesterolemia in farm animals caused by air ingestion. Assay of Lupeol (50 mg/kg) in hypercholesterolemic animals (causing myocardial damage) is sufficient to alter the level of lysosomal hydrolases. The Lupeol assay also restores the level of lipoprotein and lipid components to their original state. Recently activated Lupeol has an antidyslipidemic effect in a hamster model of dyslipidemia. In this study, information about triglyceride, triglyceride & cholesterol levels were obtained by streptozotocin (100 mg/kg) analysis in hamsters. However, it is recommended that hamsters with dorsal dyslipidemia receive Lupeol (50 mg/kg) 9.
Hepato-protective Action of Lupeol: Lupeol has been advised for its hepatoprotective abeyant. A contempt abstraction manifest that Lupeol manage aegis adjoins aflatoxin B1, a pre-eminant hepatotoxic abettor back activated beneath in vivo altitude 23. Appealingly, the hepato-protective after upshot of Lupeol was apparent to exist added than silymarin, a acclaimed accustomed hepat- protective a better. Lupeol & Lupeol-wealthy mango extract have recently been shown to inhibit 7, 12-dimethylbenzo (a) anthracene (DMBA)-prompted alarm events in an injury imitation. Many studies have been directed estimate the effectiveness of Lupeol in increasing the maximum for liver disease 24.
Lupeol (50 mg/kg) analysis for 15 canicule decidedly relieve the alarmist action deformity & added begrimed elimination of cholesterol in hypercholesterolemia rats. Especially, Lupeol was appear to decidedly abet the extent of vitamin C and E in hypercholesterolemia animals. Lupeol decidedly alleviated adapted alarmist action by abating accustomed activities of lipid metabolizing enzymes. Another address area articulate administering of Lupeol (150 mg/kg/day) relived the metal-induced hepatotoxicity in a rat archetypal accurate the hepato-protective abeyant of Lupeol 9.
Nephro-protective Action of Lupeol: Lupeol's effects are activated by its association with nephrotoxic & antiurolytic activity. Lupeol reduce calcium oxalate & has a cytoprotective effect by reducing events caused by free radicals. It also reduces cadmium in the kidneys, renal corpuscle pallor (RCC) & an epithelial branch of the adjacent tubular brain. Lupeol was studied in SKRC-45, an RCC cell line, & may affect auditory mitochondrial dynamics in RCC 25.
Lupeol may inhibit the apparent degradation of calcium, oxalate, & uric acid in the kidneys, may also reduce the absorption & release of inhibitors such as magnesium & glycosaminoglycans. Lupeol has been shown to prevent the development of hypercholesterolemia in animals prompted by give food to rats a high cholesterol diet (HCD) for 30 days. Hypercholesterolemia in HCD-compared rats was evident with an increase in free cholesterol, triglyceride & phospholipid levels in the kidneys, as well as an increase in tissue erosion & blood biochemical levels of kidney-type enzymes (lactate dehydrogenase and acid phosphatase) 9, 21, 22. Lupeol has upshot on SKRC-45, an RCC cell line & has the prospective to inhibit RCC based on mitochondrial dynamics 9.
Biological Activity of Lupeol on Humans: Although these aloft analysis declared assorted Pharmacological activities of Lupeol in-vitro & in-vivo daily or subcutaneous studies of Lupeol alone were conducted to evaluate its potential in Basset or human melanomas and abscesses. Lupeol (0.75-1.5 mg per site) was injected locally into & Basset Hounds with random melanoma 28.
In cases I-III (injection of the metastatic site), the Lupeol caused dematerialization or disturbed the metastatic melanoma body (track in melanosomes) IV. In this case (first injection site), Lupeol triggered local dissolution of tissue. In cases V-VII, Lupeol an accessory ameliorative abettor was accumulated with hyperthermia & immunotherapy to amusement melanoma. They additionally begin that Lupeol aggregate promote dematerialization of metastatic melanoma cell. This abstraction assured that contemporary administering of Lupeol was acknowledged analysis in 6 out of 7 bassets with cancerous melanomas. Beside, Lupeol (10 mg/kg, sc) at assorted times afterwards anaplasty block bounded bump pro- gression (no bounded frequency) & abroad metastasis 28.
In addition, they additionally begin that aggregate with Lupeol & added another ameliorative method such as hyperthermia & blooming corpuscle analysis had the abeyant to prolong the activity amount & advance accomplished activity affection for basset adversity melanoma 29. Consequently, they appropriate that Lupeol apperantly a atypical accessory analysis for articulate cancerous melanoma, and a college dosage &/or again bang of Lupeol become visible to be added able in alleviative the melanoma 25.
The present paper gives the dynamic information about Lupeol which is pentacyclic triterpenoid. Lupeol is found in various types of vegetables & fruits. Lupeol show beneficial action against life threatening disease like cancer, diabetes along with other disorder e.g. Inflammation, related to liver, kidney, & heart. The important point that must have to focus about Lupeol is that it shows its action with less cytotoxicity & less side effects. Lupeol not only use to treat disease but also show valuable action on whole biological system of humans.
The experimental work on Lupeol provides a platform for added preclinical research & clinical investigation to confirm the efficacy of Lupeol, one of two by single or in fusion with other treatments. Although Lupeol has a high bioavailability, the development of artificial corresponding may increase its efficacy & bioavailability. This is deriving from on a paper that showed artificial Lupeol derivatives to have higher pharmacological activity than Lupeol itself.
ACKNOWLEDGEMENT: Nil
CONFLICT OF INTEREST: Nil
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How to cite this article:
Lal P, Kale V and Mendhe S: Review on lupeol - a triterpenoid. Int J Pharmacognosy 2024; 11(1): 7-14. doi link: http://dx.doi.org/10.13040/IJPSR.0975-8232.IJP.11(1).7-14.
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Poonam Lal *, Vaidehi Kale and Sanket Mendhe
Department of Pharmaceutical Sciences, P. R. Pote Patil College of Pharmacy, Amravati, Maharashtra, India.
vaidehikale789@gmail.com
16 January 2024
29 January 2024
30 January 2024
10.13040/IJPSR.0975-8232.IJP.11(1).7-14
31 January 2024