Sunday, September 11, 2011

Phytochemicals: 15 Health Benefits of Limonoids

Limonoid, a type of phytochemical, is found abundantly in circus fruit and plants of the families Rutaceae (the rue or citrus family) and Meliaceae (a flowering plant family)

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1. Cancers
According to the study of " The neem limonoids azadirachtin and nimbolide inhibit cell proliferation and induce apoptosis in an animal model of oral oncogenesis." by Harish Kumar G, Vidya Priyadarsini R, Vinothini G, Vidjaya Letchoumy P, Nagini S. (Source from Department of Biochemistry and Biotechnology, Faculty of Science, Annamalai University, Annamalainagar, 608 002, Tamil Nadu, India.) posted in PunMed, researchers found that The results provide compelling evidence that azadirachtin and nimbolide mediate their antiproliferative effects by downregulating proteins involved in cell cycle progression and transduce apoptosis by both the intrinsic and extrinsic pathways. On a comparative basis, nimbolide was found to be a more potent antiproliferative and apoptosis inducing agent and offers promise as a candidate agent in multitargeted prevention and treatment of cancer.

2. Leukemia cells
In a study of " Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem). by Kikuchi T, Ishii K, Noto T, Takahashi A, Tabata K, Suzuki T, Akihisa T. (Source from College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.) posted in PubMed, researchers found that 7-deacetyl-7-benzoylepoxyazadiradione (7), 7-deacetyl-7-benzoylgeduin (18), and 28-deoxonimbolide (28) exhibited potent cytotoxic activity against HL60 leukemia cells with IC(50) values in the range 2.7-3.1 μM. Compounds 7, 18, and 28 induced early apoptosis in HL60 cells, observed by flow cytometry. Western blot analysis showed that compounds 7, 18, and 28 activated caspases-3, -8, and -9 in HL60 cells. This suggested that compounds 7, 18, and 28 induced apoptotic cell death in HL60 cells via both the mitochondrial- and the death receptor-mediated pathways.

3. Aedes albopictus (Asian tiger mosquito)
In a study of " Mosquito larvicidal activity of citrus limonoids against Aedes albopictus." by Hafeez F, Akram W, Shaalan EA (Source from Department of Agricultural Entomology, University of Agriculture, Faisalabad, Pakistan.) posted in PubMed, researchers found that The oils from Minneola and Chinese lime did not contain limonin and nomilin, and were therefore weak in terms of LC(50) values. Presence of limonin and nomilin in plant products is therefore a significant indicator of the pest control that needs to be exploited in other plants as well.

4. Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects
In a study of " Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. Juss. (neem)." by Akihisa T, Noto T, Takahashi A, Fujita Y, Banno N, Tokuda H, Koike K, Suzuki T, Yasukawa K, Kimura Y. (Source
from College of Science and Technology, Nihon University, Tokyo, Japan. posted in PubMed, researchers found that Upon evaluation of compounds 1-32 on the melanogenesis in the B16 melanoma cells, five compounds, 20, 26, 27, 29, and 31, exhibited marked inhibitory effect (74-91% reduction of melanin content at 25 microg/mL) with no or almost no toxicity to the cells. Seven compounds, 1, 6, 9, 10, 18, 20, and 26, on evaluation for their inhibitory effect against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, exhibited, except for compound 26, marked anti-inflammatory activity (ID(50) values 0.09-0.26 mg/ear). In addition, all of the 32 compounds exhibited moderate or potent inhibitory effects (IC(50) values of 230-501 mol ratio/32 pmol TPA) against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA. Furthermore, on evaluation of azadirachtin B (21) for its anti-tumor-initiating activity on the two-stage carcinogenesis of mouse skin tumor induced by peroxynitrite (ONOO-; PN) as an initiator and TPA as a promoter, this exhibited marked inhibitory activity.

5. Detoxification
In a study of " Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase." byPerez JL, Jayaprakasha GK, Valdivia V, Munoz D, Dandekar DV, Ahmad H, Patil BS. (Source from Department of Horticultural Sciences, Vegetable and Fruit Improvement Center, Texas A&M University, College Station Texas 77843-2119, USA.) posted in PubMed, researchers wrote that Our results indicated the highest induction of glutathione S-transferase (GST) activity against 1-chloro-2,4-dinitrobenzene (CDNB) by DNAG (67%) in lung homogenates followed by limonin-7-methoxime (32%) in treated liver homogenates. Interestingly, limonin-7-methoxime showed the highest GST activity (270%) in liver against 4-nitroquinoline 1-oxide (4NQO), while the same compound in the stomach induced GST by 51% compared to the control. The DNAG treated group induced 55% in stomach homogenates. Another phase II enzyme, quinone reductase (QR), was significantly induced by limonin-7-methoxime by 65 and 32% in liver and lung homogenates, respectively. Defuran limonin induced QR in lung homogenates by 45% and concluded that modification of limonin has differential induction of phase II enzymes. These findings are indicative of a possible mechanism for the prevention of cancer by aiding in the detoxification of xenobiotics.

6. Colon cancer
In a study of " Obacunone and obacunone glucoside inhibit human colon cancer (SW480) cells by the induction of apoptosis." by Chidambara Murthy KN, Jayaprakasha GK, Patil BS. (Source from Vegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, College Station, TX 77845-2119, USA.) posted in PubMed, researchers found that additive activity of proliferation inhibition and activation of caspase-3 by limonoids was observed when combined with camptothecin, demonstrating the induction of apoptosis and concluded that both limonoids induced apoptosis by activation of intrinsic apoptosis pathway and activation of p21 leading to arresting cells at G2/M phase of the cell cycle.

7. Immune system
According to the study of " Dietary curcumin and limonin suppress CD4+ T-cell proliferation and interleukin-2 production in mice." by Kim W, Fan YY, Smith R, Patil B, Jayaprakasha GK, McMurray DN, Chapkin RS. (Source from Program in Integrative Nutrition and Complex Diseases, Texas A&M University, College Station, TX 77843, USA.) posted in PubMed, researchers found that dietary combination with FO enhanced the suppressive effects (P < 0.05) of Cur or Lim with respect to CD4(+) T-cell proliferation in response to anti-CD3/28 mAb. These results suggest that combination chemotherapy (FO+Cur or Lim) may favorably modulate CD4(+) T-cell-mediated inflammation.

8. Antibacterial activity
in a study of " Antibacterial activity of two limonoids from Swietenia mahagoni against multiple-drug-resistant (MDR) bacterial strains." by Rahman AK, Chowdhury AK, Ali HA, Raihan SZ, Ali MS, Nahar L, Sarker SD. (Source from Department of Clinical Pharmacy and Pharmacology, Faculty of Pharmacy, University of Dhaka, Dhaka, 1000, Bangladesh.) posted in PubMed, researchers found that The antibacterial activity of these compounds was assessed against eight multiple-drug-resistant bacterial strains (clinical isolates) by the conventional disc diffusion method. While both compounds were active against all test organisms, compound 2 displayed overall more potent activity than compound 1.

9. Anti-inflammatory and analgesic activities
In a study of "Anti-inflammatory and analgesic activities of ethanolic extract and two limonoids from Melia toosendan fruit." by Xie F, Zhang M, Zhang CF, Wang ZT, Yu BY, Kou JP. (Source from Key Laboratory of Modern Chinese Medicines (China Pharmaceutical University), Ministry of Education, Nanjing 210038, PR China; Research Department of Pharmacognosy, China Pharmaceutical University, Nanjing 210038, PR China.), posted in PubMed, reseachers found that both the ethanolic extract and two limonoids displayed significant anti-inflammatory effects. Although the ethanolic extract showed remarkable analgesic effects in both writhing and hot-plate tests, the two limonoids had analgesic effects just in writhing test and suggested that the ethanolic extract of MTF had obvious anti-inflammatory and analgesic activities, and the two limonoids were the active constituents contributing to the anti-inflammatory and analgesic effects of MTF.

10. Antioxidant activity
In a study of " Red Mexican grapefruit: a novel source for bioactive limonoids and their antioxidant activity." by Mandadi KK, Jayaprakasha GK, Bhat NG, Patil BS. (Source from Vegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A & M University, College Station, TX 77843, USA) posted in PubMed, researchers found that Antioxidant capacity of the extracts as equivalents to ascorbic acid (micromol/g of the extract) was in the order, EtOAc extract > acetone extract > water extract > methanol extract. Furthermore, the EtOAC and acetone extracts were loaded onto silica gel columns to obtain four limonoid aglycons. MeOH fraction was loaded onto a dowex-50 and sepabeads resin column to obtain a limonoid glucoside. The purity of the isolated five compounds was analyzed by HPLC using a C18 column and UV detection at 210 nm. Finally, the structures of the compounds were identified as obacunone, nomilin, limonin, deacetylnomilin (DAN) and limonin-17-beta-D-glucopyranoside (LG) using 1H and 13C NMR studies.

11. Plasmodium falciparum
In a study of " Antimalarial tetranortriterpenoids from the seeds of Lansium domesticum Corr." by Saewan N, Sutherland JD, Chantrapromma K. (Source from School of Science, Walailak University, Thasala, Nakhon Si Thammarat 80160, Thailand., posted in PuBMed, researchers wrote in abstract that Five tetranortriterpenoids, domesticulide A-E (1-5), were isolated from seeds of Lansium domesticum Corr. together with 11 known triterpenoids (6-16). Their structures were elucidated by analysis of their spectroscopic data. Compounds 2, 3, 4, 7, 8, 10, 11, and 15 showed antimalarial activity against Plasmodium falciparum with IC(50)'s of 2.4-9.7 microg/ml.

12. Gender differences
In a study of " Gender differences in limonin pharmacokinetics in rats." by Liang Y, Xie L, Liu XD, Hu YZ, Lu T, Wang GJ. (Source fromCentral Laboratory of Drug Metabolism and Pharmacokinetics, Pharmaceutical University of China, Nanjing 210038, People's Republic of China.) posted in PubMed, researchers found that The total excretion of LM in the urine and bile of female rats was also found to be significantly higher than in male rats, which displayed lower concentrations of LM in the tissues, amounting to around one-half to one-tenth of those in female rats, apart from levels in the rectum and duodenum. In conclusion, the present results demonstrate the existence of marked gender difference in LM pharmacokinetics in rats.

13. Neuroblastoma
In a study of " Citrus limonoids induce apoptosis in human neuroblastoma cells and have radical scavenging activity." by Poulose SM, Harris ED, Patil BS. (Source from Vegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A&M University, College Station, TX 77843, USA) posted in PubMed, researchers found that Cytotoxicity was related to a concentration- and time-dependent increase in caspase 3/7 activity, suggesting that limonoid glucosides were capable of inducing apoptosis. Arrested cell growth and the induction of apoptosis were confirmed by flow cytometry and DNA fragmentation analysis. Importantly, caspase induction at 12 h correlated with cell survival at 24 h (P = 0.046), suggesting that apoptosis was the primary cause of cell death. We conclude that citrus limonoid glucosides are toxic to SH-SY5Y cancer cells. Cytotoxicity is exerted through apoptosis by an as yet unknown mechanism of induction. Individual limonoid glucosides differ in efficacy as anticancer agents, and this difference may reside in structural variations in the A ring of the limonoid molecule.

14. Antifungal activity
in a study of " Antifungal activity of limonoids from Khaya ivorensis." by Abdelgaleil SA, Hashinaga F, Nakatani M. (Source from Department of Pesticide Chemistry, Faculty of Agriculture (Elshatby), Alexandria University, Alexandria, Egypt. posted in PubMed, researchers found that Methyl angolensate and 1,3,7-trideacetylkhivorin displayed the highest antifungal activity against B. cinerea, with respectively 62.8 and 64.0% mycelial growth inhibition at 1000 mg litre(-1), and 73.3 and 68.6% mycelial growth inhibition at 1500 mg litre(-1). 3,7-Dideacetylkhivorin showed stronger antifungal and antibacterial activities than methyl 6-hydroxyangolensate against all of the test fungi and bacteria except Penicillium expansum Link. This is the first report on the antifungal and antibacterial effects of these limonoids. Structure-antifungal activity relationships of the limonoids isolated are discussed.

15. Anti-HIV-1
In a study of " Anti-HIV-1 limonoid: first isolation from Clausena excavata." by Sunthitikawinsakul A, Kongkathip N, Kongkathip B, Phonnakhu S, Daly JW, Spande TF, Nimit Y, Napaswat C, Kasisit J, Yoosook C. (Source from Natural Products and Organic Synthesis Research Unit (NPOS), Department of Chemistry, Faculty of Science, Kasetsart University, Bangkok 10900, Thailand.) posted in PubMed, researchers wrote in abstract that A limonoid, clausenolide-1-ethyl ether (1) and two coumarins, dentatin (2) and nor-dentatin (3), were isolated from Clausena excavata. Limonoid 1 was obtained from the crude ethanol extract of the rhizomes and the roots but had not previously been isolated from C. excavata and exhibited HIV-1 inhibitory activity. Coumarins 2 and 3, with their structures related to an anti-HIV-1 substance, (+)-calanolide A (4), were obtained from the crude chloroform extract of the rhizomes. Both induced toxicity to cells used in a syncytium assay for anti-HIV-1 activity. These compounds, 1-3, did not show any cytotoxic effect against KB and BC-1 cell lines (IC(50) value > 20 microgram/mL).

16. Etc.

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