Glandless Cottonseed Research Articles

Improvement of the Solubility of Protein Isolate from Glandless Cottonseed

Improvement of the Solubility of Protein Isolate from Glandless Cottonseed

The Effects of Oil Content on the Structural and Textural Properties of Cottonseed Butter/Spread Products.

Plant-based butters from nuts and seeds have steadily increased in consumer popularity due to their unique flavors and healthy nutritional properties. Oil content is a critical parameter to measure the proper consistency and stability of plant butter and spread products. Previous work has shown that glandless cottonseed can be used to formulate cottonseed butter products to increase the values of cottonseed. As part of the efforts made in the valorization of cottonseed, this work evaluated the effects of oil content on the microstructural and textural properties of cottonseed butter/spread products. While the oil content in the raw cottonseed kernels was 35% of the kernel biomass, additional cottonseed oil was added to make cottonseed butter products with six oil content levels (i.e., 36, 43, 47, 50, 53, and 57%). The values of three textural parameters, firmness, spreadability, and adhesiveness, decreased rapidly in an exponential mode with the increasing oil content. The particle size population in these butter samples was characterized by similar trimodal distribution, with the majority in the middle mode region with particle sizes around 4.5-10 μm. Higher oil content decreased the butter particle size slightly but increased oil separation during storage. The oxidation stability with a rapid oxygen measurement was gradually reduced from 250 min with 36% oil to 65 min with 57% oil. The results of this work provide information for the further optimization of formulation parameters of cottonseed butter products.

The nutritional and industrial significance of cottonseeds and genetic techniques in gossypol detoxification

Societal Impact StatementGossypol and its derivatives represent a class of toxic and immunosuppressive compounds that are naturally synthesized in cottonseed. These compounds pose several health hazards to humans and animals, such as heart and lung damage, breathing difficulties, and death in swine. In poultry, gossypol reduces egg production and slows growth. Studies have also shown that gossypol can indirectly harm humans and animals through the food chain. Although several physical and chemical approaches are adopted to reduce gossypol levels in cottonseed before food and feed processing, these techniques are expensive. Therefore, genetically regulating gossypol production in cotton could provide a cheaper alternative.SummaryCotton (Gossypium spp.), the most important fiber crop, is cultivated in over a hundred countries to provide raw materials for the growing textile industry. The seed obtained after delinting cotton is a rich source of protein with a vast potential for oil and feed production. Cottonseed oil production is estimated at 5.08 million metric tons and is expected to generate over 6.56 billion United States Dollars in revenue by 2029. The cake from defatted cottonseed is used as animal feed and food supplements. However, the contamination of gossypol in cottonseed limits its use. Gossypol ingestion impairs weight gain and causes anorexia, respiratory distress, and death under extreme exposure. This review highlights the significance of cottonseed oil and meal; the pharmacological uses and impact of gossypol; the chemistry, toxicity, and bioactivity of gossypol; and the physical and chemical methods used in gossypol removal during feed and food supplement processing. In addition, the biosynthetic pathway of gossypol and attempts to genetically transform some key regulators of this pathway to produce glandless cottonseed or reduce the gossypol levels in the seed are discussed.

Nutritional composition, antioxidant activity and gossypol level of Nazilli glandless cottonseed, cottonseed kernel and their cold-pressed meal

BackgroundThe study was conducted to determine the nutrient composition and gossypol levels of glandless cottonseed (GCS), glandless cottonseed kernel (GCSK) glandless cottonseed meal (GCSM) and cottonseed kernel meal (GCSKM) obtained by cold pressing of cotton seeds and kernels (Glandless Nazilli variety) as a raw material of compound feed industry.ResultFeed and dry matter (DM)-based nutrient analyses showed significant differences (p < 0.05) in DM, OM (organic matter), CP (crude protein), EE (ether extract), ash and NFE (nitrogen-free extract) contents between GCS and GCSK. The DM-based K, P, S, Mg, Ca, Na, Fe, Cu, Zn and Al contents were significantly different (p < 0.05) between GCS and GCSK. The concentrations of nonessential heavy metals (Cd, Pb, Ni and Al) in GCS, GCSK, GCSM and GCSKM samples were below the permissible limits. The linoleic acid (C18:2; ω6) was the main component (55.55%) among the 20 fatty acids identified in GCS oil. The level of unsaturated fatty acids (70.78%) was higher than that of saturated fatty acids (29.22%). Total phenolics concentrations of GCS, GCSK, GCSM and GCSKM samples were 7.87, 2.18, 5.86 and 1.91 mg gallic acid equivalents (GAE)/g, respectively. Free and total gossypol levels of GCS and GCSK were 294 and 440, and 521 and 706 mg/kg, respectively.ConclusionThe results revealed that nutritional properties of Nazilli GCS with low gossypol and high linoleic acid content were relatively higher compared to the other meals investigated. The antioxidant activity of phenolic compounds, albeit at low levels in Nazilli GCS and GCSM, may contribute to animal health and production efficiency when used in animal rations.

Cross-Serological Reaction of Glandless Cottonseed Proteins to Peanut and Tree Nut Allergic IgE

Food allergy is a potentially life-threatening health concern caused by immunoglobulin E (IgE) antibodies that mistakenly recognize normally harmless food proteins as threats. Peanuts and tree nuts contain several seed storage proteins that commonly act as allergens. Glandless cottonseed, lacking the toxic compound gossypol, is a new food source. However, the seed storage proteins in cottonseed may act as allergens. To assess this risk, glandless cottonseed protein extracts were evaluated for IgE binding by peanut and tree nut allergic volunteers. ELISA demonstrated that 25% of 32 samples had significant binding to cottonseed extracts. Immunoblot analysis with pooled sera indicated that IgE recognized a pair of bands migrating at approximately 50 kDa. Excision of these bands and subsequent mass-spectrometric analysis demonstrated peptide matches to cotton C72 and GC72 vicilin and legumin A and B proteins. Further, in silico analysis indicated similarity of the cotton vicilin and legumin proteins to peanut vicilin (Ara h 1) and cashew nut legumin (Ana o 2) IgE-binding epitopes among others. The observations suggest both the cotton vicilin and legumin proteins were recognized by the nut allergic IgE, and they should be considered for future allergen risk assessments evaluating glandless cottonseed protein products.

Initial Formulation of Novel Peanut Butter-like Products from Glandless Cottonseed.

Glandless (Gl) cottonseed is a unique cotton variety with only a trace content of toxic gossypol present. This new cottonseed raises the potential of its enhanced utilization as an agro-food for human consumption. In this work, Gl cottonseed kernels were used with additional cottonseed oil to produce novel peanut butter-like products. Kernels roasted at two temperatures (140 or 150 °C) for a given time (15 or 30 min) were first ground with different ratios of cottonseed oil and two other ingredients (i.e., salt and sugar) with a food blender, and then passed through a meat grinder with a 4-mm-hole grinding plate. Per the preliminary result, the butter-like products with Gl kernels roasted at 150 °C were subject to further structural and textural evaluation. The color of the two butter-like products was comparable to a commercial peanut butter, but the formers' textural properties were significantly different (p ≤ 0.05) from the latter. Morphologic examination by Scanning Electron Microscopy (SEM) and cryo-SEM revealed that the butter product with a longer (30 min) roasting time possessed a smoother surface than the products with a shorter (15 min) roasting time. Oil stability test showed no substantial oil separation (&lt;3%) from the butter products over 7 weeks at ambient temperature (22 °C). This work provides the basic information and parameters for lab cottonseed butter making so that optimization and characterization of cottonseed butter formation can be designed and performed in future research.

Cottonseed extracts regulate gene expression in human colon cancer cells

Cotton plant provides economically important fiber and cottonseed, but cottonseed contributes 20% of the crop value. Cottonseed value could be increased by providing high value bioactive compounds and polyphenolic extracts aimed at improving nutrition and preventing diseases because plant polyphenol extracts have been used as medicinal remedy for various diseases. The objective of this study was to investigate the effects of cottonseed extracts on cell viability and gene expression in human colon cancer cells. COLO 225 cells were treated with ethanol extracts from glanded and glandless cottonseed followed by MTT and qPCR assays. Cottonseed extracts showed minor effects on cell viability. qPCR assay analyzed 55 mRNAs involved in several pathways including DGAT, GLUT, TTP, IL, gossypol-regulated and TTP-mediated pathways. Using BCL2 mRNA as the internal reference, qPCR analysis showed minor effects of ethanol extracts from glanded seed coat and kernel and glandless seed coat on mRNA levels in the cells. However, glandless seed kernel extract significantly reduced mRNA levels of many genes involved in glucose transport, lipid biosynthesis and inflammation. The inhibitory effects of glandless kernel extract on gene expression may provide a useful opportunity for improving nutrition and healthcare associated with colon cancer. This in turn may provide the potential of increasing cottonseed value by using ethanol extract as a nutrition/health intervention agent.

Quantitative comparison of the storage protein distribution in glandless and glanded cottonseeds

AbstractGlanded (Gd) cottonseed (Gossypium hirsutum L.) contains scattered gossypol glands. Glandless (Gl) cottonseed is a new type of seed containing only trace levels of gossypol. This work quantitatively compared the content and migration pattern of Gd and Gl protein isolates. Both protein samples were subjected to sodium dodecyl sulfate (SDS)‐gel electrophoresis, and the protein gel bands were separated into seven partitions for peptide mass spectroscopic analysis. While multiple peptide fragments (isoformers) of vicilin and legumin proteins were present in both samples, the percentage of vicilins in total seed protein was higher in Gd (74.9%) than in Gl (63.4%). In contrast, legumin proteins were more abundant in Gl (30.4%) than Gd (23.6%). Minor protein components such as lipid‐related oleosins and vicilin‐like antimicrobial peptides 2‐2 were also observed at a relatively higher incidence in Gl compared with Gd, potentially reflecting a need for increased protein‐related defense capability in the absence of gossypol against natural predators or adverse growth environment.

Production of Yellow Poplar Interior Plywood with Cottonseed-based Protein Adhesives

Defatted cottonseed (CS) and water-washed CS meals were prepared from glandless CS and were used in adhesive formulations to produce three-ply yellow poplar plywood panels. Adhesive resins were prepared from each protein meal with sodium bisulfite and one of two polyamido-amine-epichlorohydrin (PAE) wet strength agents, and the plywood panels were produced by hot pressing. Shear strength and water resistance were determined by American Society of Testing and Materials (ASTM) and American National Standards Institute for Hardwood and Decorative Plywood/Hardwood Plywood and Veneer Association (ANSI/HPVA) methods and were compared with the properties of plywood panels made with an adhesive formulated from a commercial soybean meal. Panels prepared from three protein meals had comparable shear strengths. The combinations of the two CS preparations and the two wet strength agents produced panels with acceptable wet resistant properties, whereas the soybean meal only produced acceptable panels with one of the wet strength agents. Because the panels prepared from the two CS meals had comparable properties, there appears to be no benefit to including a water-washing step to increase the meal’s protein level. In contrast with recent literature reports suggesting the addition of alkali to elevate the formulation pH was necessary with CS meal, suitable panels were prepared herein without the addition of the base. This difference may have been due to the slightly higher pressing temperature and longer press times used in this work compared with earlier results. The CS meals showed promise as formaldehyde-free hardwood-plywood wood-based adhesives for interior applications.

Vicilin and legumin storage proteins are abundant in water and alkali soluble protein fractions of glandless cottonseed

In this work, we sequentially extracted water (CSPw)- and alkali (CSPa)-soluble protein fractions from glandless cottonseed. SDS-Gel electrophoresis separated CSPw and CSPa to 8 and 14 dominant polypeptide bands (110–10 kDa), respectively. Liquid chromatography-electrospray ionization-tandem mass spectrometry identified peptide fragments from 336 proteins. While the majority of peptides were identified as belonging to vicilin and legumin storage proteins, peptides from other functional and uncharacterized proteins were also detected. Based on the types (unique peptide count) and relative abundance (normalized total ion current) of the polypeptides detected by mass spectrometry, we found lower levels (abundance) and types of legumin isoforms, but higher levels and more fragments of vicilin-like antimicrobial peptides in glandless samples, compared to glanded samples. Differences in peptide fragment patterns of 2S albumin and oleosin were also observed between glandless and glanded protein samples. These differences might be due to the higher extraction recovery of proteins from glandless cottonseed as proteins from glanded cottonseed tend to be associated with gossypol, reducing extraction efficiency. This work enriches the fundamental knowledge of glandless cottonseed protein composition. For practical considerations, this peptide information will be helpful to allow better understanding of the functional and physicochemical properties of glandless cottonseed protein, and improving the potential for food or feed applications.

Cottonseed Ethanol Extracts and Gossypol Regulate Anti-Inflammatory Tristetraprolin Family Gene Expression in Mouse Cells

Abstract Objectives Bioactive plant extracts have been used for the prevention and treatment of various diseases. One of the major classes of bioactive compounds is plant polyphenols. The objective of this study was to investigate the effect of cottonseed ethanol extracts and gossypol on the cytotoxicity and regulation of anti-inflammatory tristrataprolin (TTP) family gene expression in mouse cells. Methods Mouse RAW 264.7 macrophages and 3T3-L1 adipocytes were treated with various concentrations of cottonseed extracts, gossypol and lipopolysaccharides (LPS, as a control) for 2, 8, 24 and 72 h. MTT, qPCR and immunoblotting assays were used to evaluate the effects of cottonseed extracts, gossypol and LPS on cell viability and gene expression in the mouse cells. Results No cytotoxicity effect was observed in macrophages treated with extracts from the coat or kernel of glanded and glandless cottonseed. Similarly, the viability of mouse adipocytes was not affected by cottonseed extracts. In contrast, gossypol and LPS were toxic to macrophages but not adipocytes under high concentration or long time treatment. Cottonseed extracts exhibited modest effect on TTP family gene expression in macrophages but glandless cottonseed coat extract significantly increased TTP mRNA and protein levels with a magnitude similar to cinnamon and green tea polyphenol extract and insulin. Conclusions These results demonstrated that cottonseed extracts are harmless towards the mouse cells and that glandless cottonseed coat extract stimulates TTP gene expression. We propose that glandless cottonseed is a safe source of plant polyphenols with anti-inflammatory property. Funding Sources This work was supported by the USDA-ARS Quality and Utilization of Agricultural Products National Program 306 through CRIS 6054-41,000-103-00-D. USDA is an equal opportunity provider and employer.

Regulation of Cell Viability and Anti-inflammatory Tristetraprolin Family Gene Expression in Mouse Macrophages by Cottonseed Extracts

Bioactive plant extracts have been used for the prevention and treatment of various diseases. One of the major classes of bioactive compounds is plant polyphenols. Cottonseed ethanol extracts were determined by HPLC-MS analysis to be essentially free of toxic gossypol. The objective of this study was to investigate the effect of cottonseed ethanol extracts on the cytotoxicity and regulation of anti-inflammatory tristrataprolin (TTP) family gene expression in mouse cells. MTT, qPCR and immunoblotting assays tested the effects of cottonseed extracts in mouse RAW264.7 macrophages and 3T3-L1 adipocytes. No cytotoxicity effect was observed in macrophages treated with extracts from the coat or kernel of glanded and glandless cottonseed. Similarly, the viability of mouse adipocytes was not affected by cottonseed extracts. In contrast, gossypol and lipopolysaccharides were toxic to macrophages but not adipocytes under high concentration or long time treatment. Cottonseed extracts exhibited modest effect on TTP family gene expression in macrophages but glandless cottonseed coat extract significantly increased TTP mRNA and protein levels with a magnitude similar to cinnamon and green tea polyphenol extract and insulin. These results demonstrated that cottonseed extracts are harmless towards the mouse cells and that glandless cottonseed coat extract stimulates TTP gene expression. We propose that glandless cottonseed is a safe source of plant polyphenols with anti-inflammatory property.

Characterization of Soluble Glandless Cottonseed Meal Proteins Based on Electrophoresis, Functional Properties, and Microscopic Structure.

This investigation aimed to extract and characterize the GCSM proteins, determine their solubility potential at two different temperatures and different solvents, and explore their functional properties. During the extraction, no water- or ethanol-soluble protein was found. Most of the protein was extracted with KOH solution. GCSM showed major protein bands between 13,273 and 56,564 Da with an isoelectric point of 5.1. The results showed that extraction temperature and solvent affected the amount of protein extracted from GCSM. The highest protein yield (63.4%) was obtained with KOH at 55 °C. Fat content negatively affected the protein solubility. The highest protein purity (99.9%) was obtained with 6% of fat content and the lowest one with 19% of fat content. GCSM has a high glutamic acid content, followed by arginine and aspartic acid compared to the other amino acids. The essential amino acids make up about 30.0% of the total amino acid concentration in KOH-soluble fractions. The results showed a denaturation temperature of GCSM protein ranging from 61.4 to 63.6 °C. Scanning electron microscopy reveals a microglobular protein structure. GCSM protein isolate showed lower (P < 0.05) water-holding and oil-holding capacity but similar gelation properties as soy protein. GCSM protein shows a high foaming capacity at high pH values and high emulsion stability. PRACTICAL APPLICATION: The results of this investigation have a direct impact on the plant protein processing industry. This paper presents a new source of plant protein with a high foaming capacity in alkaline conditions with potential applications for human consumption and feed for aquaculture and animals. The results of this research may impact the cotton producers who can increase their income, and the aquaculture industry will have a cheaper source of protein that can partially substitute the expensive fishmeal. Cottonseed protein can be used to develop high protein extruded snacks and other functional foods, such as plant protein-based food products.

Gossypol but Not Cottonseed Extracts or Lipopolysaccharides Stimulates HuR Gene Expression in Mouse Macrophages (P06-071-19)

ObjectivesHuman antigen R (HuR) is a homolog of Drosophila embryonic lethal abnormal vision (ELAV1). HuR binds to, stabilizes cytokine mRNAs, and plays an important role in tumorigenesis and inflammation. Plant extracts and compounds that can regulate HuR gene expression may have nutritional and therapeutic value, but no prior research was done. The objective of this study was to evaluate the effect of cottonseed extracts, anti-nutritional gossypol and endotoxin lipopolysaccharides (LPS) on the regulation of HuR gene expression in mouse macrophages. MethodsMouse RAW264.7 macrophages were treated with multiple concentrations of glanded and glandless cottonseed extracts, gossypol and LPS for 2, 8 and 24 h. qPCR and immunoblotting were used to detect the expression of HuR mRNA and protein. ResultsqPCR assay showed that cottonseed extracts and LPS had minimal effect on HuR gene expression. However, gossypol increased HuR mRNA levels up to 16-fold in cells treated for 24 h. Immunoblotting confirmed that gossypol also increased HuR protein in macrophages. ConclusionsThese results show for the first time that gossypol is a strong stimulator of HuR gene expression and that cottonseed extracts essentially free of gossypol are probably safe to use as a reliable source of plant polyphenols. Funding SourcesThis work was supported by the USDA-ARS Quality and Utilization of Agricultural Products National Program 306 through CRIS 6054–41,000-103–00-D. USDA is an equal opportunity provider and employer.

Gossypol but not cottonseed extracts or lipopolysaccharides stimulates HuR gene expression in mouse cells

Abstract Human antigen R (HuR) stabilizes cytokine mRNAs and plays an important role in tumorigenesis and inflammation. Plant extracts and compounds that can regulate HuR gene expression may have nutritional and therapeutic value, but little research has been done in this area. This study evaluated the effect of cottonseed extracts, anti-nutritional gossypol and endotoxin lipopolysaccharides (LPS) on HuR gene expression in mouse macrophages. Mouse RAW264.7 macrophages were treated with multiple concentrations of glanded and glandless cottonseed extracts, gossypol and LPS for 2–24 h. qPCR assay showed that cottonseed extracts and LPS had minor effect on HuR gene expression. However, gossypol increased HuR mRNA levels 16 fold in cells treated for 24 h. Immunoblotting confirmed that gossypol increased HuR protein in macrophages. These results showed that gossypol is a strong stimulator of HuR gene expression.

Isolation of Cottonseed Extracts That Affect Human Cancer Cell Growth

Cottonseeds are classified as glanded or glandless seeds depending on the presence or absence of gossypol glands. Glanded cottonseed has anticancer property and glandless cottonseed was reported to cause cancer in one animal study. It is important to investigate the effect of bioactive components from cottonseeds. Our objectives were to isolate ethanol extracts from cottonseeds and investigate their effects on human cancer cells. A protocol was developed for isolating bioactive extracts from seed coat and kernel of glanded and glandless cottonseeds. HPLC-MS analyzed the four ethanol extracts but only quercetin was identified in the glandless seed coat extract. Residual gossypol was detected in the glanded and glandless seed kernel extracts and but only in the glanded seed coat extract. Ethanol extracts were used to treat human cancer cells derived from breast and pancreas followed by MTT assay for cell viability. Ethanol extracts from glanded and glandless cottonseed kernels and gossypol significantly decreased breast cancer cell mitochondrial activity. Ethanol extract from glanded cottonseed kernel and gossypol also significantly decreased pancreas cancer cell mitochondrial activity. These results suggest that ethanol extracts from cottonseeds, like gossypol, contain anticancer activities.

Development and Characterization of Glandless Cottonseed Meal/Pullulan Fine Fiber Mats

Development and Characterization of Glandless Cottonseed Meal/Pullulan Fine Fiber Mats

Cytotoxicity of ethanol extracts from glanded and glandless cottonseed in cultured mouse RAW macrophages

Cotton plant provides two economically important products, fiber as the major product and cotton seed as the minor product. However, cotton plant produces more seed in terms of quantity than fiber with a seed/fiber ratio of 1.5 – 1.7. Cottonseed typically accounts for 15 – 25% of the crop value. Due to presence of toxic gossypol in the commonly cultivated cotton (glanded cotton), the uses of cottonseed is limited to feeding cows and not for human and other animal consumption. To explore the potential use of glandless cottonseed which has only trace amount of gossypol, we investigated the cytotoxicity of extracts from glandless cottonseed along with those from glanded cottonseed and compared directly with gossypol and lipopolysaccharide (LPS) using cultured mouse macrophages. Cottonseeds were separated into coat and kernel fractions. Both fractions were homogenized in 0.1 N acetic acid, defatted with chloroform and hexane and extracted with ethanol. The ethanol extracts were rotoevaporated to remove ethanol and the dried extracts were reconstituted in DMSO before being added to cultured mouse RAW264.7 macrophages using gossypol and LPS as controls. Cell cytotoxicity was determined with MTT method. Dosage study showed that no cytotoxicity effect was observed in cells treated for 2–24 h with extracts (up to 1 mg/ml) from glandless cottonseed coat or kernels, nor with glanded cottonseed coat. However, mitochondrial activity measured by the MTT method was decreased by 40% with glanded cottonseed kernel extract after cells were treated with 0.1–1 mg/ml for 24 h. LPS (up to 1 ug/ml) did not show toxic activity but gossypol (≥5 ug/ml, 24h) almost completely inhibited cell viability. These results suggest that glandless cottonseed extractis harmless towards the cultured macrophages but glanded cottonseed extract from its kernel, like gossypol, is harmful to the immunological cells.Support or Funding InformationSupported by USDA‐ARS Quality and Utilization of Agricultural Products Research Program 306 through CRIS 6054‐41000‐103‐00D.

The TMEn, Proximate Analysis, Amino Acid Content and Amino Acid Digestibility of Glandless and Commercial Cottonseed Meal for Broilers

Cotton seed meal (CSM) is an alternative ingredient in poultry diets but its use is limited due to the presence of gossypol and the potential effects of gossypol on digestibility of nutrients. Glandless cottonseed is available and contains very low gossypol but there has been a limited amount of poultry nutritional studies completed with glandless cottonseed meal (GCSM). The TMEn, proximate analysis, amino acid content and amino acid (AA) digestibility of a glandless (GCSM) and a commercial (CCSM) cottonseed meal were determined with broilers. Thirty 42-day old Cobb 500 male broilers were precision-fed 30g of CCSM, GCSM and glucose and excreta collected during a 48 h period. Glucose was fed to serve as a control (no nitrogen or AA content). The chemical composition, gossypol content, True metabolizable energy (TMEn) and digestibility coefficients for AA were calculated for both meals. The crude protein and fat content of GCSM was higher than the CCSM (54 and 51%, 6 and 2%, respectively). Both meals were similar in calcium, total phosphorus and phytic acid contents. The CCSM had a higher content of total and free gossypol (1.52 and 0.161%, respectively) when compared to GCSM (0.02 and .003%, respectively). The TMEn for the GCSM provided approximately one thousand kcal more per energy/ kg than the CCSM. The essential AA content (g/kg; 90% DM) was determined for both cottonseed meals and was generally higher for GCSM compared to CCSM but both types of CSM contained higher levels of key essential AA than reported values for AA in the literature. The most extreme differences were for methionine and cystine; % methionine content was approximately 2 fold higher than values in the literature and the % cystine was 74 to 93% higher. The true digestibility coefficients for essential AA ranged from the low of 73.9% for isoleucine to 91.8% for arginine, for CCSM; the amino acid digestibility coefficients for GCSM were all higher than 90% for the essential AAs.

A new flavonol glycoside from glandless cotton seeds

A new flavonol glycoside, namely quercetin 3-O-[α-d-apiofuranosyl(1–5)-β-d-apiofuranosyl(1–2)]-α-l-rhamnopyranosyl(1–6)-β-d-glucopyranoside (1), was isolated from glandless cotton seeds together with the known compounds quercetin 3-O-α-l-rhamnopyranosyl(1–2)-[α-l-rhamnopyranosyl(1–6)]-β-d-glucopyranoside (manghaslin, 2), kaempferol 3-O-β-d-apiofruranosyl(1–2)-β-d-glucopyranoside (3) and kaempferol 3-O-α-l-rhamnopyranosyl(1–6)-β-d-glucopyranoside (4). It is interesting that the tetrasaccharide fragment of 1 contained both a β-apiosyl and an unusual α-apiosyl group.