Biotransformation of steroidal saponins in sisal agave sisalana perrine to tigogenin by a newly isolated strain from a karst area of guilin, china yanchao wang a,b, xia li a, hao sun a, kexian yi c, jinlong zheng c, jie zhang d and zaibin hao a,b. Consequently, the growth of both the crop and the agro industrial production observed in recent. Biotechnological intervention of agave sisalana semantic scholar. Due to their properties, saponins are finding application in fine chemistry and pharmaceutical industry. Foaming glycosides saponins are low molecular weight secondary plant. Phytochemical and biological studies of agave attenuata. Agave sisalana sisal this plant can be weedy or invasive according to the authoritative sources noted below. Biotransformation of steroidal saponins in sisal agave sisalana perrine to tigogenin by a newly isolated strain from a karst area of guilin.
Sapogenins contain steroid or other triterpene frameworks as their key organic feature. Phytochemical and biological studies of agave attenuata core. Sterols, steroidal sapogenins, steroidal alkaloids and alkaloidal amines are derived from agave. This present invention relates to an improved method for producing steroidal sapogenins such as hecogenin from leaves of plants such as agave sisalana. Gcms characterisation of sapogenins from sisal waste and. However, this juice is very fibrous and is therefore not used much. The earliest report of the saponins of agave was in the year 1932 jones et al. Agave sisalana perrine sisal is a monocotyledonous plant of great. Abstract five steroidal sapogenins tigogenin, neotigogenina, hecogenin, gloriogenin, and dehydrohecogenin were characterised by gas chromatography coupled with mass spectrometry gcms from a hydrolysed extract of sisal waste. In the pharmaceutical industry, these natural compounds are used for. Applications of the hexanic fraction of agave sisalana. Journal of herbal pharmacotherapy 2006, 6 2, 101122. Biotransformation of steroidal saponins in sisal agave.
Furthermore, agave was recognized as a new and potential source of steroidal sapogenins marker et al. Keywords steroidal saponins, reproduction, testicular tissue. Despite the large number of secondary metabolites isolated from this family so far, there have been few reports on the bioactivity of. Diosgenin, a major raw material for the commercial production of steroidal contraceptives and sex hormones is. Sisal was introduced in india by portuguese in the 15th century. This plant can be weedy or invasive according to the authoritative sources noted below. A rodshaped bacterium was isolated from the soil in a karst area of guilin, china and its biotransformation of steroidal saponins in sisal agave sisalana perrine to tigogenin was presented for the first time. Gcms analysis of the nhexane fraction from the extract revealed the presence of 31 compounds, with mono2ethylhexyl phthalate 11. Pdf two new steroidal saponins, 8 and 10, along with 7 known steroidal sapogenins and saponins 17 and a furostanol saponin 9 were isolated from. Nov 28, 2014 biotransformation of steroidal saponins in sisal agave sisalana perrine to tigogenin by a newly isolated strain from a karst area of guilin, china. Gcms characterisation of sapogenins from sisal waste and a method to isolate pure hecogenin, biores.
The structure of smilagenin, a typical example, is shown ch3 ho h smilagenin in the diagram. Few steroidal sapogenins were found, largely because of the absence of agave, yucca, and dioscorea. Consequently, the growth of both the crop and the agroindustrial production observed in recent decades has caused. One of the steroids for example, sterols, bile acids, cardiac glycosides. Consequently, the growth of both the crop and the agroindustrial production observed in recent. Gcms characterisation of sapogenins from sisal waste and a. The agave sisalana is an important plant to semiarid regions worldwide due to its commercial applications as a supplier of hard fibers for the production of wires and cords 1,2. College of life science, northeast agriculture university, harbin, china. This plant may be known by one or more common names in different places, and some are listed above.
A total of 22 strains for the degradation of steroidal saponins in sisal were isolated from 48 soil samples, and the isolated rodshaped, bacterial strain zg21 was used for the. In general, plants of the genus agave live for long. Sapogenins with furostanol and furospirostanol skeleta have not been discovered in this genus yet. Effect of steroidal sapogenins on ruminal fermentation and. Steroidal saponins definition of steroidal saponins by. Sep 21, 1976 this present invention relates to an improved method for producing steroidal sapogenins such as hecogenin from leaves of plants such as agave sisalana. Process for obtaining sapogenin particularly hecogenin. The present study was conducted to examine various biological activities of a methanol extract of agave attenuata leaves. The term sisal may refer either to the plants common name or the fibre, depending on the context. Surfactant properties of the saponins of agave durangensis. The common name in english of agave americana century plant refers to the durability of this plant, which, although it does not usually live 100 years, it easily reaches 25 or 30. Evaluation of mosquito larvicidal efficacy of leaf extract. Among these agave sisalana, also known as sisal, is most prevalent species in india.
Toxicity of the extracts of sisal waste, obtained from decortications of. Some steroidal sapogenins can serve as a practical. Nov 02, 2014 a rodshaped bacterium was isolated from the soil in a karst area of guilin, china and its biotransformation of steroidal saponins in sisal agave sisalana perrine to tigogenin was presented for the first time. Agave sisalana is a plant belonging to asparagaceae family. Owens animal science department oklahoma state university stillwater 74078 abstract supplementation of dairy rations with steroidal sapogenins was evaluated in an in vitro, an in situ, and a. Antiinflammatory and analgesic potential of hydrolyzed. Among the species of agave studied for their saponin composition are agave cocui 7, agave americana 8 and agave cantala 9, and until further research has been conducted, there are at present no data about the evaluation of saponin. Steroidal sapogenins are a glycone nonsugar portion of the saponin molecule.
Biotransformation of steroidal saponins in sisal agave sisalana. Abstractfoaming glycosides, traditionally known for their detergent properties. Diosgenin, a major raw material for the commercial production of. Several sapogenins have been isolated from dong no 1, a cultivated form of this plant 1, 2. Plants belonging to the family agavaceae are used in folkloric medicinal practices worldwide and chemical investigations of these plants have shown that they are an abundant source of steroidal saponins and sapogenins.
Spirostanols are biogenetically derived from cholestane and are 16,22. The plant contains saponin having immense pharmacological importance. Dioscorea, agave and yucca have been reported among the promising source with regard to their valuable steroidal sapogenins. Sapogenin, any of a class of organic compounds occurring in many species of plants as derivatives of the steroid and the triterpenoid groups in the form of their glycosides, the saponins q.
Roland eddy from the eastern regional research laboratory, philadelphia, pennsylvania received for publication, february 7, 1952 in recent years the steroidal sapogenins have received considerable atten. Kon, steroidal alkaloid saponins and steroidal saponins from solanum surattense, phytochemistry, 72, 668 2011. It yields a stiff fibre used in making various products. Gcms characterisation of sapogenins from sisal waste and a method to isolate pure hecogenin five steroidal sapogenins tigogenin, neotigogenina, hecogenin, gloriogenin, and dehydrohecogenin were characterised by gas chromatography coupled with mass spectrometry gcms from a hydrolysed extract of sisal waste. Evaluation of mosquito larvicidal efficacy of leaf extract of. In the pharmaceutical industry, these natural compounds are used for the semisynthesis of medicinal steroids, as corticosteroids, sexual hormones and steroid diuretics 5. Yanchao wang college of chemistry and bioengineering, guilin university of technology, guilin, china. Process for obtaining sapogenin particularly hecogenin from. In order to find out the values of the steroid resources for the future use. It is in east africa, particularly tanzania and kenya, that cultivation of agave sisalana developed into a major industry and hybrid varieties of the plant were developed, which gave extended production life and higher fibre content to the leaves, though over the last 40 years. The ab rings may have a cis or trans fusion and, therefore, structure elucidation of sapogenins saponins of agave requires determination of the ab ring junction. The leaves of agave lecheguilla, both green and dead, contained about 1.
A total of 22 strains for the degradation of steroidal saponins in sisal were isolated from 48 soil samples, and the isolated rod. The genus name agave was given by linnaeus in 1753. Show full abstract were qualitatively identified in 86 species, 45 of which. Us2895953a us703712a us70371257a us2895953a us 2895953 a us2895953 a us 2895953a us 703712 a us703712 a us 703712a us 70371257 a us70371257 a us 70371257a us 2895953 a us2895953 a us 2895953a authority us united states prior art keywords partially hydrolyzed saponin sapogenin purification saponins prior art date 19571218 legal status the legal status is an. Sapogeninas esteroidicas em sisal steroidal sapogenins in. The most common variants are ring inversion at cl, cis. It is sometimes incorrectly referred to as sisal hemp because hemp was for centuries a major source for fibre, so other fibres were sometimes named after it. It is an extensively cultivated species around the world, in tropical and subtropical zones oashi, 1999.
Blunden g, carabot a, jewers k 1980 steroidal sapogenins from leaves of some species of agave and furcrea. It is suggested that, in the bulbils, gitogeninas first generation in sapogenin biogenesisgives tigogeninas second generationwhich transforms m the cousre of the long life of the plant to hecogenin and neotigogeninas third generation. Phytochemical and biological studies of agave attenuata komal rizwan 1, muhammad zubair 1. Preparation of steroidal hormones with an emphasis on. Isolation and enzyme inhibitory studies of steroids and alkaloidal steroid saponins from solanum surattense burm. Effect of steroidal sapogenins on ruminal fermentation and on production of lactating dairy cows 1 f. Steroidal sapogenins have been reported from a number of plant species. Introduction agave sisalana is a very important resource of hard fibre and steroidal material, which was introduced from abroad and has been cultivated in the south of china. Thus, the study of the extraction of these components from their natural matrixes and their optimization is of.
Four new steroid constituents from the waste residue of. Extraction of saponins from sisal agave sisalana and. Three new steroidal saponins, dongnosides ce, were isolated from the methanol extracts of the fermented residues of leavejuices of agave sisalana form. For example, steroidal sapogenins such as tiggenin, neogitogenin, and tokorogenin have been isolated from the tubers of chlorophytum arundinaceum. Sapogenins are the aglycones, or nonsaccharide, portions of the family of natural products known as saponins.
Santos and alexsandro branco five steroidal sapogenins tigogenin, neotigogenina, hecogenin. Action of sisal agave sisalana, perrine extract in the in vitro development of sheep and goat gastrointestinal nematodes. Hormonal steroids from steroidal sapogenins of dioscoreae one such natural source is diosgenin 27, a steroidal sapogenin, first isolated by tsukamoto from the yam dioscorea tokoro makino9, but which can also be found in the tubers of other species of the dioscoreae dioscorea villosa, d. Two new steroidal saponins, 8 and 10, along with 7 known steroidal sapogenins and saponins 17 and a furostanol saponin 9 were isolated from agave sisalana perrine ex engelm. Steroidal sapogenin contents in some domestic plants. Agave sisalana, also known as sisal, is an herbaceous monocotyledonous plant from the agavaceae family. Detection and estimation of steroidal sapogenins in plant. Agave is an important source of steroidal sapogenins of the spirostanoltype 127 whereas agavegenin d 28 is the only cholestanetype sapogenin reported from agave. Pdf studies on sapogenin concentrate from agave sisalana. Four new steroid constituents from the waste residue of fibre. Steroidal saponins and sapogenins from the agavaceae family. The steroid sapogenin constituents of agave sisaluna at various phases of growth have been identified. Agave sisalana sisal proved the most successful of these species.
Agave and other genera of agavaceae are rich in secondary metabolites, meanly steroidal saponins 6. It is rich in saponins, which are necessary for generation of steroidal materials called sapogenins specifically hecogenin and tigogenin. Many species of the genus agave constitute an important source of steroidal sapogenins, mainly hecogenin 4. Barbourgenin, a new steroidal sapogenin from agave sisalana. Consequently, the growth of both the crop and the agro industrial production observed in recent decades has caused. Sapogenin definition is a nonsugar portion of a saponin that is typically obtained by hydrolysis, has either a complex terpenoid or a steroidal structure, and in the latter case forms a practicable starting point in the synthesis of steroid hormones. The genus agave has more than 275 species distributed in different continents of the word, of which agave sisalana, agave cantala, agave mexicana, agave veracruz and agave americana occur in india. Sisal agave sisalana is an agave that yields a stiff fibre traditionally used in making twine, rope and also dartboards. Agave the genus agave consists of over 100 species and leaf extracts from these plants have been used as laxatives, diuretics, antisyphillitics and. Pdf a rodshaped bacterium was isolated from the soil in a karst area of guilin, china and its biotransformation of steroidal saponins in sisal agave. And pennogenin intrillium kamtschaticum andparis verticillata, yuccagenin inallium. Sapogenin definition of sapogenin by merriamwebster.
Steroidal saponins from a cultivated form of agave sisalana. Pdf biotransformation of steroidal saponins in sisal. Extracts from these plants have been available as cardioactive or larvicide, and are popularly used in other ailments achenbach et al. Steroidal saponins and sapogenins from the agavaceae.
Barbourgenin, a new steroidal sapogenin from agave. Barbourgenin is a steroidal sapogenin from agave sisalana leaves. Barbourgenin, a new steroidal sapogenin from agave sisalana leaves. The term may refer either to the plant or the fibre, depending on context. Till now, more than 50 species of agave have been investigated for their saponin and sapogenin constituents. However, to the best of our knowledge, no investigations on the production of tigogenin using biotransformation were reported.
From the leaves of agave lecheguilla torrey, two steroidal sapogenin diols have been isolated. Agave desmettiana is a diminutive species with relatively short leaves, a short inflorescence, and short suckers fig. Five steroidal sapogenins tigogenin, neotigogenina, hecogenin, gloriogenin, and dehydrohecogenin were characterised by gas chromatography coupled with mass spectrometry gcms from a hydrolysed extract of sisal waste. Steroid sapogenins are constituents of agave utahensis var. A similar group of steroid compounds, the genins, is present in the venom of toads, not as glycosides.
Two new steroidal saponins from the fresh leaves of agave. In 2011, the world production of sisal fibers exceeded 410,000 tons. Pdf cytotoxic steroidal saponins from agave sisalana. Agave the genus agave consists of over 100 species and leaf extracts from these plants have been used as laxatives, diuretics, antisyphillitics and in the treatment of jaundice, dysentery and skin disorders 810. Saponin glycosides are divided into 2 types based on the chemical structure of their aglycones sapogenins. The hecogenin and tigogenin contents were determined in dried leaves of sisal agave sisalana and of the hybrids of a. There are forms that may have marginal spines or entire margins.
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