Antiproliferative Triterpene Saponins from <i>Entada</i> <i>africana</i>

Cioffi, Giuseppina; Piaz, Fabrizio Dal; Caprariis, P. De; Sanogo, Rokia; Marzocco, Stefania; Autore, Giuseppina; Tommasi, Nunziatina De

doi:10.1021/np060257w

Cited by 48 publications

(43 citation statements)

References 23 publications

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“…Soaking and removal of water is expected to remove saponins and the heat treatment would inactivate trypsin inhibitor activity. From E. africana roots, Cioffi et al (2006) isolated and characterised nine new triterpenoid ester saponins having echinocystic acid and acacia acid as aglycon. Moderate to high cytotoxic potency against epithelial kidney cell lines was found for almost all compounds isolated.…”

Section: Plants Containing Multibioactive Compoundsmentioning

confidence: 99%

Bioactivity of phytochemicals in some lesser-known plants and their effects and potential applications in livestock and aquaculture production systems

Makkar

Francis

Becker

2007

Animal

378

214

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Livestock and aquaculture production is under political and social pressure, especially in the European Union (EU), to decrease pollution and environmental damage arising due to animal agriculture. The EU has banned the use of antibiotics and other chemicals, which have been shown to be effective in promoting growth and reducing environment pollutants because of the risk caused to humans by chemical residues in food and by antibiotic resistance being passed on to human pathogens. As a result of this, scientists have intensified efforts in exploiting plants, plant extracts or natural plant compounds as potential natural alternatives for enhancing the livestock productivity. This paper discusses work on the effects of various phytochemicals and plant secondary metabolites in ruminant and fish species. The focus is on (i) plants such as Ananas comosus (pine apple), Momordica charantia (bitter gourd) and Azadirachta indica (neem) containing anthelmintic compounds and for their use for controlling internal parasites; (ii) plants containing polyphenols and their applications for protecting proteins from degradation in the rumen, increasing efficiency of microbial protein synthesis in rumen and decreasing methane emission; for using as antioxidants, antibacterial and antihelmintic agents; and for changing meat colour and for increasing n-3 fatty acids and conjugated linoleic acid in meat; (iii) saponin-rich plants such as quillaja, yucca and Sapindus saponaria for increasing the efficiency of rumen fermentation, decreasing methane emission and enhancing growth; for producing desired nutritional attributes such as lowering of cholesterol in monogastric animals; for increasing growth of fish (common carp and Nile tilapia) and for changing male to female ratio in tilapia; and for use as molluscicidal agents; (iv) Moringa oleifera leaves as a source of plant growth factor(s), antioxidants, beta-carotene, vitamin C, and various glucosinolates and their degraded products for possible use as antibacterial, antioxidant, anticarcinogenic and antipest agents; (v) Jatropha curcas toxic variety with high levels of various phytochemicals such as trypsin inhibitor, lectin, phytate and phorbol esters in seeds limiting the use of seed meal in fish and livestock diets; and the use of phorbol esters as bio-pesticidal agent; and (vi) lesser-known legumes such as Entada phaseoloides seeds containing high levels of trypsin inhibitor and saponins, Sesbania aculeate seeds rich in non-starch polysaccharides and Mucuna pruriens var. utilis seeds rich in L-3,4-dihydroxyphenylalanine and their potential as fish feed; Cassia fistula seeds as a source of antioxidants; and the use of Canavalia ensiformis, C. gladiata and C. virosa seeds containing high levels of trypsin inhinitor, lectins and canavanine. The paper also presents some challenges and future areas of work in this field.

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Section: Plants Containing Multibioactive Compoundsmentioning

confidence: 99%

Bioactivity of phytochemicals in some lesser-known plants and their effects and potential applications in livestock and aquaculture production systems

Makkar

Francis

Becker

2007

Animal

378

214

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“…[6] The orientation of the hydroxyl groups of ring A were assigned as 2β and 3β on the basis of 1 those reported for related compounds. [7,8] The resonance at δ 4.53 (br m) and its multiplicity indicated the presence of a 16α-OH, a conclusion that was further supported by 13 C NMR data and by signal of Me-27 (δ 1.40, s) which resonated downfield from its usual position. [8] Assignments of all chemical shifts of protons and carbons of the aglycone portion were ascertained from a combination of 1D-TOCSY, DQF-COSY, and HSQC analysis.…”

Section: Resultsmentioning

confidence: 72%

Secondary metabolites from Paronychia argentea

Braca

Bader

Siciliano

et al. 2007

Magnetic Reson in Chemistry

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“…In the 1 H-NMR spectrum, signals assignable to carbinylic protons of the aglycon were observed at d 3.42 (dd, Jϭ11.7, 3.9 Hz) and 5.30 (br s), suggesting the carbinylic protons could be placed at 3a and 16b, respectively. 25) Thus, the aglycon was identified as 3b,16a-dihydroxyolean-12-en-28-oic acid (echinocystic acid). 26,27) The aglycon was isolated after acid hydrolysis of 1 and confirmed by comparison of the spectral and physical data with those of an authentic sample.…”

Section: Resultsmentioning

confidence: 99%

“…The extract was washed with H 2 O, and evaporated to give echinocystic acid (3 mg), which was identified by comparison of its spectral and physical data with those of an authentic sample. 25) The H 2 O layer was concentrated under reduced pressure to dryness, to give a residue of the sugar fraction. The residue was dissolved in pyridine (0.1 ml), to which 0.08 M L-cysteine methyl ester hydrochloride in pyridine (0.15 ml) was added.…”

Section: Resultsmentioning

confidence: 99%

Pancreatic Lipase-Inhibiting Triterpenoid Saponins from Fruits of Acanthopanax senticosus

et al. 2007

Chem. Pharm. Bull.

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A increasing number of people are suffering from obesity, which is often associated with the development of type II diabetes, coronary heart diseases, hyperlipidemia, hypertension, and metabolic syndrome.1,2) It is well known that pancreatic lipase plays an important role in lipid digestion. The inhibition of pancreatic lipase reduces the efficiency of dietary fat absorption in the small intestine and thereby promotes modest long-term reduction in body weight. 3)Acanthopanax senticosus (RUPR. et MAXIM.) HARMS. is a shrub, belonging to the family Araliaceae, which is commonly distributed in the northeast of Asia. Different parts of the plant have been widely used as traditional Chinese medicines for the treatment of a variety of human diseases, such as ischemic heart diseases, neurasthenia, hypertension, arthritis, and tumors.4) Recently, we have reported fifteen triterpenoid saponins from the leaves of A. senticosus, among which ciwujianoside C 1 , tauroside H 1 , 3-O-a-L-rhamnopyranosyl-(1→2)-a -L-arabinopyranosyl mesembryanthemoidigenic acid, acanthopanaxoside C, sessiloside, and chiisanoside exhibited pancreatic lipase inhibitory activity in vitro.5) The occurrence of triterpenoid saponins has also been demonstrated in a previous chemical investigation of the fruits of A. senticosus.6) As our continuous investigation on bioactive triterpenoid saponins 5,7-9) and our current interest in the natural lipase inhibitors, 5,9,10) we initiated a chemical investigation of the fruits of A. senticosus. The total saponin fraction exhibited inhibitory activity on pancreatic lipase with the IC 50 value of 3.63 mg/ml. Further isolation of this fraction resulted in the isolation of sixteen triterpenoid saponins (1-16), including a new compound, acanthopanaxoside E (1). The biological activities of 1-16 against pancreatic lipase were examined. Silphioside F (2), 11) copteroside B (3), Results and DiscussionThe air-dried fruits of A. senticosus were extracted with 70% EtOH. The 70% EtOH extract was suspended in H 2 O and then partitioned successively with EtOAc and n-BuOH. The n-BuOH soluble fraction was subjected to a Diaion HP-20 column, followed by washing with H 2 O and 50% MeOH to remove phenolic compounds, and then with MeOH to result in a crude saponin fraction, which inhibited pancreatic lipase (IC 50 value: 3.63 mg/ml). Further isolation of this fraction by combination of silica gel column chromatography (CC), ODS CC and preparative HPLC afforded sixteen triterpenoid saponins, including a new compound, acanthopanaxoside E (1). The known saponins were identified as silphioside F (2), China. Received February 7, 2007; accepted April 19, 2007; published

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Antiproliferative Triterpene Saponins from Entada africana

Cited by 48 publications

References 23 publications

Bioactivity of phytochemicals in some lesser-known plants and their effects and potential applications in livestock and aquaculture production systems

Bioactivity of phytochemicals in some lesser-known plants and their effects and potential applications in livestock and aquaculture production systems

Secondary metabolites from Paronychia argentea

Pancreatic Lipase-Inhibiting Triterpenoid Saponins from Fruits of Acanthopanax senticosus

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