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‫2102/12/4‬




                                                                                                               ‫‪Glycosides‬‬

                                                                                                                                                            ‫تعريف‬     ‫•‬
             ‫.7.1-‪Phcog‬‬
                                                                                                                          ‫از نظر کمياوی متشكل از دو قسمت ذيل مياشد‬    ‫•‬
      ‫‪Medicinal Plants Containing‬‬                                                                      ‫‪R‬‬

                                                                                                                                             ‫قسمت قندی )‪(Glycon‬‬      ‫١.‬
             ‫‪Glycosides‬‬
                                                                                                                            ‫قسمت غير قندی )‪(Aglycon or Genin‬‬         ‫٢.‬

                                                                                                       ‫ارتباط ‪Glycon‬و‪ Aglycon‬توسط 2‪ N2 ،S ، O‬و ‪ C‬تامين ميگردد‬         ‫•‬
  ‫‪Abdul Ghani Karimi‬‬
  ‫‪Department of Pharmacognosy, Faculty of Pharmacy‬‬
  ‫1931.20.20:‪Date‬‬




                      ‫خواص ھيتروزيد ھا‬                                                                            ‫خواص ....‬
                               ‫• در انساج گياھان بشکل منحل موجود ميباشند‬
                                                                                     ‫• جمع اوری در فصل نا مساعد و ذخيره نمودن نا مناسب باعث ازبين رفتن اين‬
                            ‫• بصورت استخراج شده ساختمان کرستاليک دارند‬
                                                                                                                                                  ‫مرکبات ميگردد.‬
    ‫• بصورت عموم با محلول استات سرب و محلول مواد تانيک رسوب ميدھند‬
                                                                                     ‫• خشک نمودن سريع طی حرارت ٠۵ تا ٠۶ درجۀ سانتيگراد ضروری پنداشته‬
                          ‫• نظر به موجوديت رابطۀ اسيتال غير مقاوم ميباشند.‬
                                                                                                                                                          ‫می شود.‬

                                    ‫• در مرکبات عضوی غير منحل ميباشند.‬
                                                                                         ‫• انبار نمودن بعد از جمع آوری موجب افزايش حرارت و فعال شدن انزايم ھا‬

                                                    ‫• از لحاظ نوری فعال اند‬                                                                              ‫می گردد.‬

                               ‫• انزايم ھا نقش مھم را در ھايدروليز آنھا دارند‬




                          ‫‪Classification‬‬                                                                   ‫‪2. Based on Aglycon‬‬

                         ‫‪1. Based on Glycon‬‬
                                                                                    ‫.1‬     ‫‪Cyanogenic Glycosides‬‬

                                                                                    ‫.2‬     ‫‪Thio Glycosides‬‬
‫‪α and β‬‬
                                       ‫نظر به موقعيت ھايدروکسيل در 1‪ C‬قندھا‬     ‫•‬   ‫.3‬     ‫‪Cardiotonic Glycosides‬‬

‫‪Pentosides & Hexosides‬‬
                                         ‫به اساس تعداد کاربن در واحدھای قندھا‬   ‫•‬   ‫.4‬     ‫‪Saponosids‬‬

‫‪Glucopyranosides & Glucofuranosides‬‬                                                 ‫.5‬     ‫‪Anthraglucosides‬‬
                                                      ‫به اساس توتومتری قندھا‬    ‫•‬
                                                                                    ‫.6‬     ‫‪Iridoides‬‬
‫‪O, C,S and N-Glycosides‬‬              ‫به اساس رابطه ميان قسمت قندی و غيرقندی‬     ‫•‬




                                                                                                                                                                            ‫1‬
4/21/2012




                       Group Activity
         Identify glycosides according to their Linkages




                                                 Aloin or Barbaloin

                                                                         Cyanogenitic Glycosides



    sinigrin




               Cyanogenic Glycosides                                                ‫عمده ترين ھتروزيدھای سيانوجنيک‬
• Glycosides that yield hydrocyanic acid (HCN) on hydrolysis
• Common glycosides are derivatives of mandelonitrile                 Glycoside          Source                    Family

(benzaldehyde - cyanohydrin).                                         Amygdalin          Prunus amygdalus          Rosaceae
• They are not widely distributed in the plant kingdom                Linamarin          Linum usitatissimum       Linaceae
• Widely used as flavoring agent in cough preparations                Prulaurasin        Prunus laurocerasus       Rosaceae
• Mild sedative and for treatment of irritant and persistent
                                                                      Sambunigrin        Sambucwas nigra           Caprifoliaceae
coughs
                                                                      Prunasin           Prunus serotina           Rosaceae




                       Biosynthesis                                          Amygdalus communis Var. amara
                                                                                (syn.Prunus amygdalus)

                                                                                                                ‫درختچۀ پربرگ به قامت‬      •
                                                                                                                               ‫٢-۴ متر‬
                                                                                                                 ‫برگھا ساختمان نيزه نما‬   •
                                                                                                                              ‫ونوک تيز‬
                                                                                                                 ‫گلھا منفرد و پنج عددی‬    •
                                                                                                               ‫دارای رنگ گالبی روشن‬
                                                                                                               ‫- گلھا قبل از ظھور برگھا‬
                                                                                                                          ‫شگوفا ميگردند‬
                                                                                                                   Drupa ‫ميوه بشکل‬        •




                                                                                                                                              2
‫2102/12/4‬




                 ‫‪Geographical Distribution‬‬                                                                                    ‫اوصاف درگ‬
                                               ‫• بين ارتفاعات ٠٠٨ الی ٠٠٦١متر‬                                                     ‫• دروگ گياه را تفاله دانه ھا تشکيل ميدھد.‬
            ‫- بصورت وحشی در قفقاز، افغانستان، آسيای ميانه ومرکزی ميرويد.‬                                ‫• ھيتروزيد ھا بعد از استخراج تيل شحمی بطريقه فشار سرد استخراج‬
                           ‫• کشت آن بنا بر ارزش غذايی وطبی رائج شده است‬                                                                                              ‫ميگردد.‬
‫‪The top 6 almond production countries in 2009 according to‬‬                                                  ‫• تفالۀ دارای انزايم ‪ (B-Glycosidase) Emulsine‬ميباشد.‬
‫.‪FAO in tonnes‬‬
                                                                                                          ‫• آب بادام تلخ توسط عمليه تقطير به کمک بخارات آب بدست ميايد.‬
‫.1‬   ‫002,261,1..… ‪United States of America‬‬
                                                                                                                                ‫• قبل از عمليۀ تفاله در آب گرم اخته ميشود.‬
‫.2‬   ‫001,672……………… ‪Spain‬‬
‫.3‬   ‫200,79.………………………… ‪Syria‬‬                                                                        ‫• برای تھيه مستحضر مذکور ميتوان از تفاله دانه ھای تلخ شفتالو و زردالو‬
‫.4‬   ‫448,45 ..……………‪Turkey‬‬
‫.5‬   ‫393,74..……………………… ‪Algeria‬‬                                                                                                                               ‫نيز استفاده کرد.‬
‫.6‬   ‫000,53…… ‪People's Republic of China‬‬




                            ‫تشخيص توصيفی‬                                                                                 ‫ترکيب کيمياوی‬
                                                                                                                                                  ‫تيل شحمی ٠٢ تا ٠٦ فيصد‬        ‫•‬
‫‪Grignard Reaction‬‬
                                                                                                                                         ‫ھيتروزيد ‪(3-5%) amygdaline‬‬             ‫•‬
                        ‫)‪Filter paper (strip‬‬       ‫‪Drug‬‬                                                                                               ‫مواد پروتئينی )%02(‬       ‫•‬
                                                                                                                                                         ‫تيل مفر )% 5.0 (‬       ‫•‬
                          ‫% 1 ‪Picric acid‬‬         ‫‪Flask‬‬                                                                        ‫ويتامينھا )ويتامين ھای گروپ ‪ B‬مانند 2‪(Vit. B‬‬     ‫•‬
                                                                                                                                                     ‫مواد قندی )%3 – 2 (‬        ‫•‬
                                                                                                            ‫قسمت قندی ھيتروزيد را دای سکرايد ‪ Gentiobiose‬تشكيل داده است‬         ‫•‬
                          ‫%01 3‪Na2CO‬‬
                                               ‫‪Hanging of‬‬                                                              ‫ھايدروليز ‪ Amygdalin‬طی سه مرحله صورت می گيرد‬             ‫•‬
                                               ‫‪filter paper‬‬
                                 ‫‪Dry‬‬
                                                ‫‪Heat the‬‬
                                                 ‫‪flask‬‬


                                          ‫‪Brick red color‬‬




                   ‫تاثيرات فزيولوژيکی و استطباب‬                                                                    ‫‪Prunus serotina‬‬
                                                                                        ‫‪• A woody plant growing to 15–30 m tall‬‬
      ‫• آب بادام تلخ حاوی %1.0 اسيد سيانوھيدريک بشکل ازاد ويا ارتباطی ميباشد.‬           ‫‪• The leaves are simple, 6–14 cm long, with a‬‬
       ‫• اين مستحضر بصورت قطره و محلول برای تسکين درد و به گونۀ آرام کنندۀ‬                ‫.‪serrated margin‬‬
                                                              ‫عصبی استطباب دارد .‬       ‫.‪• The flowers are small with five white petals‬‬
         ‫تيل شحمی بادام تلخ محلل خوب برای تعداد زيادی از مستحضرات دوائی‬             ‫•‬   ‫‪• The fruit is a drupe, green to red at first, ripening‬‬
          ‫محسوب ميگردد )مانند کامفر، بعضی از ھورمون ھای جنسی و غيره (.‬                    ‫. ‪black‬‬
                      ‫تيل شحمی بادام دارای خاصيت مسھل ضعيف نيز ميباشد.‬              ‫•‬   ‫‪• This plant is native to eastern states of USA and‬‬
                                                                                          ‫.‪certain parts of Canada‬‬
                                                                                        ‫,‪• In the USA it is found abundantly in Florida‬‬
                                                                                          ‫‪Dakota, Mississippi, north Carolina and Virginia‬‬




                                                                                                                                                                                     ‫3‬
4/21/2012




            Used parts, constituents and use
                                                                              Other species containing cyanogenic
•    Dried bark
                                                                                          glycosides
•    Color: dark-brown

•    Odor: bitter almond like

•    Taste: bitter and astringent

•    Size: 10 X 4 cm, Thickness= 3-4 mm

     Cherry bark contains a cyanogenic glycosid (prunasin).

     Prunasin     prunase
                                    Benzaldehyde + Glucose + HCN
                                                                                 Apricot                  Peach              Apple                Cherry
    The drug also contain p-coumaric acid, and other organic acid such   (Armeniaca vulgaris Lam.)   (Prunus persica)   (Malus sylvastiris)   (Pronus avium)

    as benzoic acid.
    Wild cherry is employed as flavored in cough syrup
    It is also used as a sedative expectorant




                            Thank you




                                                                                                                                                                      4

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Phcog 1.7

  • 1. ‫2102/12/4‬ ‫‪Glycosides‬‬ ‫تعريف‬ ‫•‬ ‫.7.1-‪Phcog‬‬ ‫از نظر کمياوی متشكل از دو قسمت ذيل مياشد‬ ‫•‬ ‫‪Medicinal Plants Containing‬‬ ‫‪R‬‬ ‫قسمت قندی )‪(Glycon‬‬ ‫١.‬ ‫‪Glycosides‬‬ ‫قسمت غير قندی )‪(Aglycon or Genin‬‬ ‫٢.‬ ‫ارتباط ‪Glycon‬و‪ Aglycon‬توسط 2‪ N2 ،S ، O‬و ‪ C‬تامين ميگردد‬ ‫•‬ ‫‪Abdul Ghani Karimi‬‬ ‫‪Department of Pharmacognosy, Faculty of Pharmacy‬‬ ‫1931.20.20:‪Date‬‬ ‫خواص ھيتروزيد ھا‬ ‫خواص ....‬ ‫• در انساج گياھان بشکل منحل موجود ميباشند‬ ‫• جمع اوری در فصل نا مساعد و ذخيره نمودن نا مناسب باعث ازبين رفتن اين‬ ‫• بصورت استخراج شده ساختمان کرستاليک دارند‬ ‫مرکبات ميگردد.‬ ‫• بصورت عموم با محلول استات سرب و محلول مواد تانيک رسوب ميدھند‬ ‫• خشک نمودن سريع طی حرارت ٠۵ تا ٠۶ درجۀ سانتيگراد ضروری پنداشته‬ ‫• نظر به موجوديت رابطۀ اسيتال غير مقاوم ميباشند.‬ ‫می شود.‬ ‫• در مرکبات عضوی غير منحل ميباشند.‬ ‫• انبار نمودن بعد از جمع آوری موجب افزايش حرارت و فعال شدن انزايم ھا‬ ‫• از لحاظ نوری فعال اند‬ ‫می گردد.‬ ‫• انزايم ھا نقش مھم را در ھايدروليز آنھا دارند‬ ‫‪Classification‬‬ ‫‪2. Based on Aglycon‬‬ ‫‪1. Based on Glycon‬‬ ‫.1‬ ‫‪Cyanogenic Glycosides‬‬ ‫.2‬ ‫‪Thio Glycosides‬‬ ‫‪α and β‬‬ ‫نظر به موقعيت ھايدروکسيل در 1‪ C‬قندھا‬ ‫•‬ ‫.3‬ ‫‪Cardiotonic Glycosides‬‬ ‫‪Pentosides & Hexosides‬‬ ‫به اساس تعداد کاربن در واحدھای قندھا‬ ‫•‬ ‫.4‬ ‫‪Saponosids‬‬ ‫‪Glucopyranosides & Glucofuranosides‬‬ ‫.5‬ ‫‪Anthraglucosides‬‬ ‫به اساس توتومتری قندھا‬ ‫•‬ ‫.6‬ ‫‪Iridoides‬‬ ‫‪O, C,S and N-Glycosides‬‬ ‫به اساس رابطه ميان قسمت قندی و غيرقندی‬ ‫•‬ ‫1‬
  • 2. 4/21/2012 Group Activity Identify glycosides according to their Linkages Aloin or Barbaloin Cyanogenitic Glycosides sinigrin Cyanogenic Glycosides ‫عمده ترين ھتروزيدھای سيانوجنيک‬ • Glycosides that yield hydrocyanic acid (HCN) on hydrolysis • Common glycosides are derivatives of mandelonitrile Glycoside Source Family (benzaldehyde - cyanohydrin). Amygdalin Prunus amygdalus Rosaceae • They are not widely distributed in the plant kingdom Linamarin Linum usitatissimum Linaceae • Widely used as flavoring agent in cough preparations Prulaurasin Prunus laurocerasus Rosaceae • Mild sedative and for treatment of irritant and persistent Sambunigrin Sambucwas nigra Caprifoliaceae coughs Prunasin Prunus serotina Rosaceae Biosynthesis Amygdalus communis Var. amara (syn.Prunus amygdalus) ‫درختچۀ پربرگ به قامت‬ • ‫٢-۴ متر‬ ‫برگھا ساختمان نيزه نما‬ • ‫ونوک تيز‬ ‫گلھا منفرد و پنج عددی‬ • ‫دارای رنگ گالبی روشن‬ ‫- گلھا قبل از ظھور برگھا‬ ‫شگوفا ميگردند‬ Drupa ‫ميوه بشکل‬ • 2
  • 3. ‫2102/12/4‬ ‫‪Geographical Distribution‬‬ ‫اوصاف درگ‬ ‫• بين ارتفاعات ٠٠٨ الی ٠٠٦١متر‬ ‫• دروگ گياه را تفاله دانه ھا تشکيل ميدھد.‬ ‫- بصورت وحشی در قفقاز، افغانستان، آسيای ميانه ومرکزی ميرويد.‬ ‫• ھيتروزيد ھا بعد از استخراج تيل شحمی بطريقه فشار سرد استخراج‬ ‫• کشت آن بنا بر ارزش غذايی وطبی رائج شده است‬ ‫ميگردد.‬ ‫‪The top 6 almond production countries in 2009 according to‬‬ ‫• تفالۀ دارای انزايم ‪ (B-Glycosidase) Emulsine‬ميباشد.‬ ‫.‪FAO in tonnes‬‬ ‫• آب بادام تلخ توسط عمليه تقطير به کمک بخارات آب بدست ميايد.‬ ‫.1‬ ‫002,261,1..… ‪United States of America‬‬ ‫• قبل از عمليۀ تفاله در آب گرم اخته ميشود.‬ ‫.2‬ ‫001,672……………… ‪Spain‬‬ ‫.3‬ ‫200,79.………………………… ‪Syria‬‬ ‫• برای تھيه مستحضر مذکور ميتوان از تفاله دانه ھای تلخ شفتالو و زردالو‬ ‫.4‬ ‫448,45 ..……………‪Turkey‬‬ ‫.5‬ ‫393,74..……………………… ‪Algeria‬‬ ‫نيز استفاده کرد.‬ ‫.6‬ ‫000,53…… ‪People's Republic of China‬‬ ‫تشخيص توصيفی‬ ‫ترکيب کيمياوی‬ ‫تيل شحمی ٠٢ تا ٠٦ فيصد‬ ‫•‬ ‫‪Grignard Reaction‬‬ ‫ھيتروزيد ‪(3-5%) amygdaline‬‬ ‫•‬ ‫)‪Filter paper (strip‬‬ ‫‪Drug‬‬ ‫مواد پروتئينی )%02(‬ ‫•‬ ‫تيل مفر )% 5.0 (‬ ‫•‬ ‫% 1 ‪Picric acid‬‬ ‫‪Flask‬‬ ‫ويتامينھا )ويتامين ھای گروپ ‪ B‬مانند 2‪(Vit. B‬‬ ‫•‬ ‫مواد قندی )%3 – 2 (‬ ‫•‬ ‫قسمت قندی ھيتروزيد را دای سکرايد ‪ Gentiobiose‬تشكيل داده است‬ ‫•‬ ‫%01 3‪Na2CO‬‬ ‫‪Hanging of‬‬ ‫ھايدروليز ‪ Amygdalin‬طی سه مرحله صورت می گيرد‬ ‫•‬ ‫‪filter paper‬‬ ‫‪Dry‬‬ ‫‪Heat the‬‬ ‫‪flask‬‬ ‫‪Brick red color‬‬ ‫تاثيرات فزيولوژيکی و استطباب‬ ‫‪Prunus serotina‬‬ ‫‪• A woody plant growing to 15–30 m tall‬‬ ‫• آب بادام تلخ حاوی %1.0 اسيد سيانوھيدريک بشکل ازاد ويا ارتباطی ميباشد.‬ ‫‪• The leaves are simple, 6–14 cm long, with a‬‬ ‫• اين مستحضر بصورت قطره و محلول برای تسکين درد و به گونۀ آرام کنندۀ‬ ‫.‪serrated margin‬‬ ‫عصبی استطباب دارد .‬ ‫.‪• The flowers are small with five white petals‬‬ ‫تيل شحمی بادام تلخ محلل خوب برای تعداد زيادی از مستحضرات دوائی‬ ‫•‬ ‫‪• The fruit is a drupe, green to red at first, ripening‬‬ ‫محسوب ميگردد )مانند کامفر، بعضی از ھورمون ھای جنسی و غيره (.‬ ‫. ‪black‬‬ ‫تيل شحمی بادام دارای خاصيت مسھل ضعيف نيز ميباشد.‬ ‫•‬ ‫‪• This plant is native to eastern states of USA and‬‬ ‫.‪certain parts of Canada‬‬ ‫,‪• In the USA it is found abundantly in Florida‬‬ ‫‪Dakota, Mississippi, north Carolina and Virginia‬‬ ‫3‬
  • 4. 4/21/2012 Used parts, constituents and use Other species containing cyanogenic • Dried bark glycosides • Color: dark-brown • Odor: bitter almond like • Taste: bitter and astringent • Size: 10 X 4 cm, Thickness= 3-4 mm Cherry bark contains a cyanogenic glycosid (prunasin). Prunasin prunase Benzaldehyde + Glucose + HCN Apricot Peach Apple Cherry The drug also contain p-coumaric acid, and other organic acid such (Armeniaca vulgaris Lam.) (Prunus persica) (Malus sylvastiris) (Pronus avium) as benzoic acid. Wild cherry is employed as flavored in cough syrup It is also used as a sedative expectorant Thank you 4