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Structures of triterpenoids from the leaves of Lansium domesticum

Matsumoto T, Kitagawa T, Ohta T, Yoshida T, Imahori D, Teo S, et al.

J Nat Med, 2019 Sep;73(4):727-734.
PMID: 31104253 DOI: 10.1007/s11418-019-01319-2

From the methanolic extract of the leaves of Lansium domesticum, three new onoceranoid-type triterpenoids, lansium acids X-XII and a new cycloartane-type triterpene, lansium acid XIII, were isolated. The chemical structures of the isolated new compounds were elucidated on the basis of chemical/physicochemical evidence. For new onoceranoid-type triterpenoids, the absolute configurations were established by comparison of experimental and predicted electronic circular dichroism (ECD) data. The isolated onoceranoid-type triterpenoids showed antimutagenic effects in the Ames assay against 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1).

Matched MeSH terms: Antimutagenic Agents/pharmacology*
Antimutagenic effects of aqueous fraction of Myristica fragrans (Houtt.) leaves on Salmonella typhimurium and Mus musculus

Akinboro A, Bin Mohamed K, Asmawi MZ, Yekeen TA

Acta Biochim. Pol., 2014;61(4):779-85.
PMID: 25520963

Natural plant extracts offer a promising hope in the prevention/treatment of cancer arising from genetic mutations. This study evaluated in vitro and in vivo mutagenic and antimutagenic effects of aqueous fraction of Myristica fragrans (AFMF) leaves on TA100 strain of Salmonella typhimurium and Mus musculus (Male Swiss albino mice), respectively. The antioxidant activity of AFMF against 2,2-diphenyl-1-picrylhydrazyl (DPPH), total phenolic and flavonoid contents were determined, followed by its phytochemical elucidation using the Ultra Performance Liquid Chromatography technique (UPLC). The mutagenicity of AFMF at 4, 20, 50, 100, 200, 500, and 1000 µg/well was <2.0 in S. typhimurium and the induced micronucleated polychromatic and normochromatic erythrocytes at 500, 1000, 2000, and 4000 mg/kg were not significantly different from the negative control (p≥0.05). The mutagenic activity of benzo[a]pyrene and cyclophosphamide was significantly suppressed above 50.0% throughout the tested concentrations. Fifty percent of the free radicals from DPPH were scavenged by AFMF at 0.11 mg/ml. Total phenolic and flavonoid contents of AFMF were 51.0 mg GAE/g and 27 mg QE/g, respectively. Rutin was elucidated by the UPLC technique, and thereby suspected to be the phytochemical responsible for the observed antimutagenic activity. Thus far, AFMF seems to contain a promising chemotherapeutic agent for the prevention of genetic damage that is crucial for cancer development.

Matched MeSH terms: Antimutagenic Agents/pharmacology*; Antimutagenic Agents/therapeutic use*
Toxicology study of vanillin on rats via oral and intra-peritoneal administration

Ho K, Yazan LS, Ismail N, Ismail M

Food Chem Toxicol, 2011 Jan;49(1):25-30.
PMID: 20807560 DOI: 10.1016/j.fct.2010.08.023

Vanillin is useful as anti-sickle cell anemia, anti-mutagen and anti-bacteria agent. However, vanillin must be administered at high concentration and cannot be oxidized by the upper gastrointestinal track of patients to be medically effective. In this study, we assessed the toxic effect of vanillin when administered in an un-oxidized form at high concentrations (150 and 300 mg/kg) via oral and intra-peritoneal injection. It was found that 300 mg/kg vanillin injection caused the rats to be unconscious without exerting any toxic effect on blood cells, kidney and liver. Besides, it showed blood protective property. Further analysis with GenomeLab GeXP genetic system on brain tissues showed that the expression of most xenobiotic metabolism, cell progression, tumor suppressor, DNA damage and inflammation genes were maintained at normal level. However, the expression of a few xenobiotic metabolism, cell cycle arrest and apoptosis genes were up-regulated by 5% ethanol injection. Nevertheless, when 5% ethanol was injected with the presence of vanillin, the expression was back to normal level. It is postulated that vanillin might have neuro-protective property. In conclusion, vanillin is not toxic at high concentration in both oral and intra-peritoneal injection and could provide blood and brain protective properties.

Matched MeSH terms: Antimutagenic Agents/administration & dosage; Antimutagenic Agents/toxicity*
Mutagenic and antimutagenic activities of aqueous and methanol extracts of Euphorbia hirta

Loh DS, Er HM, Chen YS

J Ethnopharmacol, 2009 Dec 10;126(3):406-14.
PMID: 19778596 DOI: 10.1016/j.jep.2009.09.025

Euphorbia hirta (E. hirta) is a weed commonly found in tropical countries and has been used traditionally for asthma, bronchitis and conjunctivitis. However, one of the constituents in this plant, quercetin, was previously reported to be mutagenic. This work aimed to determine the level of quercetin in the aqueous and methanol plant extracts and to investigate the mutagenic effects of quercetin and the extracts in the Ames test utilising the mutant Salmonella typhimurium TA98 and TA100 strains. The antimutagenic activity of Euphorbia hirta aqueous and methanol extracts was also studied in Salmonella typhimurium TA98. HPLC analyses showed that quercetin and rutin, a glycosidic form of quercetin, were present in the acid-hydrolysed methanol extract and non-hydrolysed methanol extract respectively. The quercetin concentration was negligible in both non-hydrolysed and acid-hydrolysed aqueous extracts. The total phenolic contents in Euphorbia hirta were determined to be 268 and 93 mg gallic acid equivalent (GAE) per gram of aqueous and methanol extracts, respectively. Quercetin (25 microg/mL) was found to be strongly mutagenic in Salmonella typhimurium TA98 in the absence and presence of S-9 metabolic activation. However, both the aqueous and methanol extracts did not demonstrate any mutagenic properties when tested with Salmonella typhimurium TA98 and TA100 strains at concentrations up to 100 microg/mL in the absence and presence of S-9 metabolic activation. In the absence of S-9 metabolic activation, both the extracts were unable to inhibit the mutagenicity of the known mutagen, 2-nitrofluorene, in Salmonella typhimurium TA98. On the other hand, the aqueous extracts at 100 microg/mL and methanol extracts at 10 and 100 microg/mL exhibited strong antimutagenic activity against the mutagenicity of 2-aminoanthracene, a known mutagen, in the presence of S-9 metabolic activating enzymes. The results indicated that these extracts could modulate the xenobiotic metabolising enzymes in the liver at the higher concentrations.

Matched MeSH terms: Antimutagenic Agents/toxicity*
Structures and Antimutagenic Effects of Onoceranoid-Type Triterpenoids from the Leaves of Lansium domesticum

Matsumoto T, Kitagawa T, Teo S, Anai Y, Ikeda R, Imahori D, et al.

J Nat Prod, 2018 10 26;81(10):2187-2194.
PMID: 30335380 DOI: 10.1021/acs.jnatprod.8b00341

A methanol extract of the dried leaves of Lansium domesticum showed antimutagenic effects against 3-amino-1,4-dimethyl-5 H-pyrido[4,3- b]indole (Trp-P-1) and 2-amino-1-methyl-6-phenylimidazo[4,5- bI]pyridine (PhIP) using the Ames assay. Nine new onoceranoid-type triterpenoids, lansium acids I-IX (1-9), and nine known compounds (10-16) were isolated from the extract. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. The absolute stereostructures of the new compounds were determined via their electronic circular dichroism spectra. Several isolated onoceranoid-type triterpeneoids showed antimutagenic effects in an in vitro Ames assay. Moreover, oral intake of a major constituent, lansionic acid (10), showed antimutagenic effects against PhIP in an in vivo micronucleus test.

Matched MeSH terms: Antimutagenic Agents/pharmacology*
Fulltext In vivo anticlastogenic effect of silymarin from milk thistle Silybum marianum L

Anwar S, Madkor HR, Ahmed N, Wagih ME

Indian J Pharmacol, 2018 9 1;50(3):108-115.
PMID: 30166747 DOI: 10.4103/ijp.IJP_660_16

OBJECTIVE: Silymarin, extracted from the seeds of Silybum marianum L. (Milk thistle), is traditionally used for treating various illnesses such as diabetes, cancer, inflammation, hepatitis, liver cirrhosis, and renal problems. Acute cytotoxicity and genotoxicity studies have been reported with ambiguous outcomes; however, its relevant anticlastogenic potential is not yet evaluated. This study was aimed to evaluate in vivo subacute anticlastogenic properties of silymarin to validate its use as a medicinal agent.
MATERIALS AND METHODS: Silymarin was isolated from seeds of milk thistle. Various genotoxicity bioassays of silymarin were performed using mice. First, the bone marrow cell proliferation was estimated by calculating mitotic index. Second, the chromosomal abnormalities in mice bone marrow cells were studied. Third, micronucleated polychromatic erythrocytes (MPE) test and in vivo activation of sister chromatid exchanges (SCEs) were carried out in mice bone marrow cells. Finally, primary spermatocytes were analyzed to estimate genotoxic effect of silymarin on germ cells.
RESULTS: We found that silymarin is capable of inducing a significant increase (P ≤ 0.05) in cell proliferation of bone marrow cells. There is no increase in chromosomal aberrations following silymarin treatments. Results clearly showed that it significantly (P ≤ 0.05) decreased the MPE. Likewise, it was found to be a negative inducer of SCEs. It decreased in total abnormal metaphase, SCEs, MPE, and aberrant diakinesis.
CONCLUSION: The results demonstrated that silymarin has a strong anticlastogenic activity upon mice genome in somatic and germ cells, indicating its safe use as a medicinal substance. Furthermore, it is not only safe but also has protective effect from clastogens.

Matched MeSH terms: Antimutagenic Agents/pharmacology*
Mutagenic and antimutagenic assessment of methanol leaf extract of Myristica fragrans (Houtt.) using in vitro and in vivo genetic assays

Akinboro A, Mohamed KB, Asmawi MZ, Othman AS, Ying TH, Maidin SM

Drug Chem Toxicol, 2012 Oct;35(4):412-22.
PMID: 22149219 DOI: 10.3109/01480545.2011.638300

The role of diets in causing cancers necessitates the ongoing search for natural antimutagens of promising anticancer therapeutics. This study determined the potential anticancer efficacy of the leaf extract of Myristica fragrans (Houtt.). Methanol leaf extract of M. fragrans (Houtt.) alone was screened for mutagenicity in the bacterial reverse mutation (Ames) test, using the Salmonella typhimurium TA100 strain, the Allium cepa, and the mouse in vivo bone marrow micronucleus tests. The antimutagenicity of this extract against benzo[a]pyrene- and cyclophosphamide-induced mutations was evaluated. An antioxidant test on the extract was performed with 2,2-diphenyl-1-picrylhydrazyl, using butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) as the standards, whereas its phytochemicals were elucidated by following the gas chromatography/mass spectrometry protocol. In S. typhimurium (TA100), the mutagenicity ratio at 200,500 and 1,000 µg/well was >2. Cell division in the A. cepa root tips and mouse bone marrow was significantly (P ≤ 0.05) inhibited at 2,000 and 4,000 mg/kg, whereas the observed chromosomal aberrations and micronucleated polychromatic erythrocytes were non-dose-related and were insignificantly (P ≥ 0.05) different from the negative control. Inhibition of benzo[a]pyrene- and cyclophosphamide-induced mutagenicity by this extract was above 40%. Half-maximal inhibitory concentration of the extract in the antioxidant test was lower than that of BHA and BHT. Phytochemical compounds, possessing antioxidant activity, may be responsible for the observed effects, suggesting a strong antimutagenic activity of the MeOH leaf extract of M. fragrans, a necessary characteristic of a promising anticancer agent.

Matched MeSH terms: Antimutagenic Agents/administration & dosage; Antimutagenic Agents/isolation & purification; Antimutagenic Agents/pharmacology*
Apoptosis and cell cycle arrest of human colorectal cancer cell line HT-29 induced by vanillin

Ho K, Yazan LS, Ismail N, Ismail M

Cancer Epidemiol, 2009 Aug;33(2):155-60.
PMID: 19679064 DOI: 10.1016/j.canep.2009.06.003

Vanillin is responsible for the flavor and smell of vanilla, a widely used flavoring agent. Previous studies showed that vanillin could enhance the repair of mutations and thus function as an anti-mutagen. However, its role in cancer, a disease that is closely related to mutation has not yet been fully elucidated.

Matched MeSH terms: Antimutagenic Agents/pharmacology*
50% Ethanol extract of Orthosiphon stamineus modulates genotoxicity and clastogenicity induced by mitomycin C

Al-Dualimi DW, Shah Abdul Majid A, Al-Shimary SFF, Al-Saadi AA, Al Zarzour R, Asif M, et al.

Drug Chem Toxicol, 2018 Jan;41(1):82-88.
PMID: 28635332 DOI: 10.1080/01480545.2017.1317785

Herbal products contain a variety of compounds which may be useful in protecting against cellular damage caused by mutagens. Orthosiphon stamineus (O.s) also known as Cat whiskers. The herb has been shown anti-oxidative properties and can modulate key cellular proteins that have cytoprotective effect. The study aimed to evaluate the effects of different doses (250, 500 and 1000 mg kg-1) of 50% ethanol extract of O.s (Et. O.s) on micro-nucleated polychromatic erythrocytes (MNPCE), Polychromatic to normachromatic erythrocytes ratio (PCE/NCE), Mitotic index (MI), and Chromosomal aberration (CA) in Bab/c mice. Moreover, these parameters were used to evaluate the anti-genotoxic and clastogenic potencies of (Et. O.s) against mitomycin c (MMC) that interact with biological molecules and induce genotoxic and clastogenic disorders in non-tumor cells. MMC (4 mg kg-1) was injected intraperitoneally (i.p.) to the mice before and after treatment with three different doses of (Et. O.s). The results indicated that the extract at different doses did not show significant (p ≥ 0.05) differences in (MNPCE), (PCE/NCE) ratios, and (CA) values. The higher doses sowed high (MI) values compared with untreated control group. MMC showed significant increase (p ≤ 0.001) in (MNPCE), (CA) and reduce (PCE/NCE) and (MI) values compared with untreated control group. Treatment with (Et. O.s) at different doses before and after MMC injection showed to modulate MNPCE, PCE/NCE ratios, CA and MI values in mice bone marrow cells suggesting genoprotective potential of this plant extract.

Matched MeSH terms: Antimutagenic Agents/isolation & purification; Antimutagenic Agents/pharmacology*
Phytochemistry and biology of Loranthus parasiticus Merr, a commonly used herbal medicine

Moghadamtousi SZ, Kamarudin MN, Chan CK, Goh BH, Kadir HA

Am J Chin Med, 2014;42(1):23-35.
PMID: 24467533 DOI: 10.1142/S0192415X14500025

Loranthus parasiticus Merr (L. parasiticus) is a member of Loranthaceae family and is an important medicinal plant with a long history of Chinese traditional use. L. parasiticus, also known as Sang Ji Sheng (in Chinese), benalu teh (in Malay) and baso-kisei (in Japanese), is a semiparasitic plant, which is mostly distributed in the southern and southwestern regions of China. This review aims to provide a comprehensive overview of the ethnomedicinal use, phytochemistry and pharmacological activity of L. parasiticus and to highlight the needs for further investigation and greater global development of the plant's medicinal properties. To date, pharmacological studies have demonstrated significant biological activities, which support the traditional use of the plant as a neuroprotective, tranquilizing, anticancer, immunomodulatory, antiviral, diuretic and hypotensive agent. In addition, studies have identified antioxidative, antimutagenic, antiviral, antihepatotoxic and antinephrotoxic activity. The key bioactive constituents in L. parasiticus include coriaria lactone comprised of sesquiterpene lactones: coriamyrtin, tutin, corianin, and coriatin. In addition, two proanthocyanidins, namely, AC trimer and (+)-catechin, have been recently discovered as novel to L. parasiticus. L. parasiticus usefulness as a medicinal plant with current widespread traditional use warrants further research, clinical trials and product development to fully exploit its medicinal value.

Matched MeSH terms: Antimutagenic Agents