Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity.

Weibel, E. K.; Hadváry, Paul; Hochuli, Erich; Kupfer, Ernst; Lengsfeld, Hans

doi:10.7164/antibiotics.40.1081

Cited by 306 publications

(169 citation statements)

References 4 publications

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“…The lipstatin molecule includes an unusual β-lactone structure that is responsible for irreversible lipase inhibition. Lipstatins are used in diabetes and obesity treatment and are available on the market as a component of a drug termed orlistat [105].…”

Section: Other Activitiesmentioning

confidence: 99%

Biologically active secondary metabolites from Actinomycetes

Solecka¹,

Zajko²,

Postek³

et al. 2012

Open Life Sciences

110

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AbstractSecondary metabolites obtained from Actinomycetales provide a potential source of many novel compounds with antibacterial, antitumour, antifungal, antiviral, antiparasitic and other properties. The majority of these compounds are widely used as medicines for combating multidrug-resistant Gram-positive and Gram-negative bacterial strains. Members of the genus Streptomyces are profile producers of previously-known secondary metabolites. Actinomycetes have been isolated from terrestrial soils, from the rhizospheres of plant roots, and recently from marine sediments. This review demonstrates the diversity of secondary metabolites produced by actinomycete strains with respect to their chemical structure, biological activity and origin. On the basis of this diversity, this review concludes that the discovery of new bioactive compounds will continue to pose a great challenge for scientists.

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Section: Other Activitiesmentioning

confidence: 99%

Biologically active secondary metabolites from Actinomycetes

Solecka¹,

Zajko²,

Postek³

et al. 2012

Open Life Sciences

110

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“…Planar Structure of Panclicin A (1) Homodecoupling experiments on 1 established proton connectivities in partial structures, A, C1'H2 (<5H 1.76)-C2H (<3H 3.21)-C3H («SH 4.30)-C4H2 (<5H 2.00 and 2.16)-C5H (5H 5.08)-C6H2 (<5H 1.62), and B, C3"CH3 (<5H 1.46)-C2"H (t5H 4.65)-NH (dH 6.16)-C1'"H (<5H 8.19). The proton 1"'-H was assigned to the NH-CHOgroup because it was coupled with the NHand its chemical shift 3H 8.19 was almost the same as that of the formyl proton in 6.…”

Section: Structural Elucidationmentioning

confidence: 99%

Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation.

Yoshinari¹,

Aoki²,

Ohtsuka³

et al. 1994

J. Antibiot.

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Panclicins A~E are novel and potent pancreatic lipase inhibitors produced by Streptomyces sp. NR 0619. Their structures have been elucidated based on NMRand FAB-MSexperiments. The relative configurations have also been determined by NMR experiments. The absolute stereochemistry has been determined by the chiral HPLCanalysis of the hydrolysates of panclicins A and B and by modified Mosher's method on a derivative of panclicin A. They are structurally related to /Mactone esterase inhibitors of microbial origin, lipstatin, valilactone, ebelactones and esterastin. Panclicins also contain a /Mactone structure with two alkyl chains, one of which has an 7V-formylalanyloxy or iV-formylglycyloxy substituent.In our screening program for novel pancreatic lipase inhibitors, we discovered potent inhibitors, panclicins A (1), B (2), C (3), D (4) and E (5), in the culture broth of Streptomyces sp. NR 0619. Their structures were determined as shown in Fig. 1 based on NMRand MSexperiments, hydrolysis and modified Mosher's method on a degradation product of 1 and were related to /Mactone esterase inhibitors of microbial origin, lipstatin1*, valilactone2), ebelactones3) and esterastin4). In the preceding paper, the taxonomical study and the production, isolation and biological activity of panclicins have been reported5). In the present paper, we describe their physico-chemical properties and structural elucidation.

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“…It has been shown to act through inhibition of pancreatic lipase (PL), which is a key enzyme for the digestion of dietary triglycerides [26]. Orlistat is a saturated derivative of lipastatin, an inhibitor of PL isolated from the bacterium Streptomyces toxytricini [27]. This molecule exerts a modest weight lowering effect while accompanying a suitable dietary advice.…”

Section: Introductionmentioning

confidence: 99%

Obesity: Development, Epidemiology, Factors Affecting, Quantity, Health Hazards, Management and Natural Treatment-a Review

Bollapragada

Shantaram

Kumar

2017

Int J Pharm Pharm Sci

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Due to the advancement in science, enhanced knowledge on the physiological aspects of almost all the tissues and the organs of the human body is gained. One of the most important prevalent topics needed for discussion is obesity and its effect on the metabolic changes leading to disorders in the human body such as diabetes, hypertension, cardiovascular diseases in addition to chronic diseases such as stroke, osteoarthritis, sleep apnea, some cancers, and inflammation-based pathologies. In recent years, obesity is a serious socioeconomic issue, which has become one of the major health problems all over the world, affecting people of all ages, sex, ethnicities and races. Obesity is a complex and multifactorial disease caused by the interaction of a myriad genetics, dietary, lifestyle and environmental factors and it is characterised by an excessive weight for height due to an enlarged fat deposition in the adipose tissue, which is due to a higher calorie intake than the energy expenditure. The pharmaceutical drugs are currently available to treat obesity but generally they have unpleasant side effects. Recent researches demonstrated the potential of natural products to counteract on obesity. Now the novel promising approach is the usage of dietary supplements and plant products and their bioactive compounds that could interfere on pancreatic lipase activity, food intake, lipid metabolism and adipocyte differentiation. In a similar way, hundreds of extracts are currently being isolated from plants, fungi, algae or bacteria and are screened for their potential inhibitions of activity against obesity. Natural products may have a synergistic activity that increases their bioavailability and action on multiple molecular targets.

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Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation and biological activity.

Cited by 306 publications

References 4 publications

Biologically active secondary metabolites from Actinomycetes

Biologically active secondary metabolites from Actinomycetes

Panclicins, novel pancreatic lipase inhibitors. II. Structural elucidation.

Obesity: Development, Epidemiology, Factors Affecting, Quantity, Health Hazards, Management and Natural Treatment-a Review

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