Phytopharm midterm

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What defines a GLYCOSIDE?

A multitude of glycosides are found in nature. These are not related at all, either botanically or chemically. What make them glycosides is that the sugar unit is attached to a non-carbohydrate molecule - an Aglycone.

Name the 11 subdivisions of the GLYCOSIDE family

1. Anthraquinone 2. Saponin 3. Cyanophore 4. Alcohol 5. Isothiocyanate 6. Lactone 7. Phenolic 8. Cardiac 9. Tannins 10. Flavinoids 11. Aldehyde

What is the function of the sugar portion of a GLYCOSIDE and what is the non-carb portion called?

The sugar allows for easy absorption and dispersion within the body. After the sugar is removed, the remaining molecule, called an Aglycone becomes active.

What is the basic structure and function of an ANTHRAQUINONE?

1. Found in well known laxative plants such as: Aloe, Senna, Cascara and Rhubarb
2. They have strong cathartic action
3. Hoffman states: they can damage epithelial cells, leading to changes in absorption, secretion and motility. Can cause pigmentation of the epithelial cells and cellular damage leading to cancer (Psuedomelanosis).
4. Also lead to griping and potenial electrolyte depletion.
5. Use only in stubborn cases, never for longer than a month and never in pregnancy.

What type of GLYCOSIDE is in Senna?

An ANTHRAQUINONE: Glycoside = Sennoside A (as well as others): a dimeric glycoside (two phenolic groups attached with hydrogen bonding). Contains KETONES, which are very irritating to the body/colon.

What type of GLYCOSIDE is in Cascara Sagrada (Rhamnus Purshiana) A.K.A Buckthorne?

An ANTHRAQUINONE: Cascarosides A, B, C & D.
The bark of the tree is used. It is dried for a year to oxidise the glycosides for a milder action. Contraindicated for Ulcerative Colitis and Crohns disease due to their irritating nature. Do not use in pregnancy.

What type of GLYCOSIDES are found in Aloe?

Two ANTHRAQUINONES: Aloe-Emodin and Emodin. Found in the exterior of the leaves. Highly cathartic. The inner gel polysaccharides contain Acemannan that speeds cell growth & healing.

What type of GLYCOSIDE is found in Chinese Rhubarb?

The favorite of the Chinese Cathartics. The Root is used and contains the ANTHRAQUINONE Rhein. Has been shown to prevent Kidney damage.

What defines SAPONIN GLYCOSIDES?

Adaptogens, good for inflammation -Saponins on hydrolysis yield an aglycone known as SAPOGENIN. Two types:
1. "Steriodal": The so-called NEUTRAL saponins are derivatives of STEROIDS with spiroketal side chains (4 rings).
2. "Triterpenoid": The ACID saponins possess triterpenoid structures (5 rigns).
Saponins come from the word Saponify or "like soap".

What type of GLYCOSIDE is in Licorice? What is the name of the AGLYCONE?

The triterpeniod saponin glycoside is GLYCYRRHIZIN. The Aglycone is GLYCYRRHETINIC ACID. It is of the Triterpenoid group.

What are the properties of Glycyrrhetinic Acid?

1. Has both expectorant and antitussive properties.
2. Anti-inflammatory - structure similar to Cortisone.
3. Believed to inhibit the enzymes that metabolize prostaglandins, increasing the level in the digestive system. Prostaglandins inhibit gastric secretion and stimulate pancreatic secretions and mucus secretions in the intestines. Can relieve paptic ulcers.
4. Can mimick aldosterone (increases urinary excretion of potassium making sodium levels too high -EDEMA

Give examples of medicinal herbs that are anthraquinone glycosides

1. Senna - contains the AGLYCONE: Sennoside A
2. Cascara Sagrada (Buckthorne)
3. Aloe Vera - AGLYCONE: Aloe-emodin and emodin
4. Chinese Rhubarb - AGLYCONE: Rhein

Give examples of herbs that are saponin glycosides

Steroidal (4 rings): Alteratives, Balance hormones
1. Soy - binds to estrogen receptors, less estrogenic
2. Yucca - alterative, cleans blood, balances hormones
3. Eleuthero (eleutherosides) - alterative
4. Ginsing (ginsenosides) & Ashwaganda (withanolide)- raises low testoserone, supports healthy iron levels.
Others: Wild yam (diosogenin), Tribulus, Smilax, Fenugreek
Triterpenoid (5 rings):
1. Liccorice -(glyzzheretenic acid) treats ulcers and heals the gut
2. Poke root - treats lymphatic congestion

What type of glycoside is found in Poke Root?

A Triterpenoid saponin glycoside

What defines Cyanophore glycosides?

1. Expectorants, sooths smooth muscle spasms.
2. All cyanophore glycosides break down into aglycone, sugar and cyanide (smells like almonds). Can be very toxic in larger doses.
3. Found in the rose family: Wild cherry, apples, pears, apricots, almonds.

What type of glycoside is in Wild cherry bark? What is the name of the aglycone? What are the end products of the metabolized aglycone?

1. Wild Cherry contains Cyanophore glycosides
2. The Aglycone is called Prunasin
3. Prunasin is metabolized into glucose, cyanide and benzaldehyde

What are the properties of Prunasin and it's component Benzaldehyde?

Benzaldehyde is a nontoxic derivative or Prunasin (cyanide has been removed). It has shown significant cancer-fighting abilities. It kills cancer cells.

What type of glycoside is in Almonds?

Amygdalin. It has powerful anticancer properties, but is contoversial due to the cyanide content. A drug called Laetrile or Vitamin B17 has been synthesized to mimick it's cancer fighting abilities. Cyanide poisoning can lead to liver and nerve damage, vomiting, blue skin color from lack of axygen, etc.

What are the properties of Alcohol Glycosides?

Antiinflammatory and analgesic. Good for pain, but take 6 hours to covert to the aglycone and activate (vs. 20 min for aspirin). Good for chronic pain -no negative side effects on the gut lining. Can be used in people with Dysbiosis (poor gut flora), although they do not absorb them well.

What type of glycoside is in White Willow Bark?
What is the name of the glycoside and the aglycone?

Salix Alba contains the alcohol glycoside Salicin. The aglycone is Saligenin, which is metabolized to the carboxylic acid Salicylic Acid. Salicylic Acid has similar health effects to Asalicylic Acid (aspirin). It is an analgesic and antiinflammatory. It does not reduce fever, irritate the stomach lining or prevent joint healing and is metabolized at a much slower rate (6hrs vs. 20min). It is also not nearly as concentrated so a much larger quatity is needed for the same effect.

Define the properties of an Isothocyanate Glycoside.

Alteratives. They are Nitrogen-Sulfur compounds. Found in the Brassica family: Wasabi, Horse Radish, Mustard Greens, Brussle Sprouts, Broccoli, Kale. Contains Sulfur, and induce glutathione Transferase which is very important in supporting the detox functions of the liver (4 out of the 7 phase II detox pathways contain S). They are also rubifacients (topical, warmimg anagesic), can suppress thyroid activity, decongestants and help prevent cancer.

What type of glycoside is in Broccoli? What is the Aglycone called? How does it function in the body?

The Isothiocyanate Glycoside Glucobracssicin is metabloized to the stable Aglycone Indole-3-carbinol. This aglycone is used by the body to break down excess estrogens in the liver and prevent the production of toxic estorgen levels.

What type of glycoside is in Wasabi?

Wasabi contains the Isothiocyanate glycoside Sinigrin.

What are the properties of the Lactone Glycosides?

Blood thinners. Contain the Coumarins found in the Apiaceae family. It includes angelica, anise, caraway, carrot, celery, coriander/cilantro, cumin, dill, fennel, hemlock, lovage, Queen Anne's Lace, parsley, parsnip, etc. Are excellent in the treatment of skin conditions such as Psoriasis, but enhance the photosensitivity of the skin.

What type of glycoside is found in Arabian Pea? What is the name of the Aglycone?

It contains Lactone glycosides called furanocoumarins (5 c sugar). The aglycone is called Angelicin. It is an antiinflammatory, but causes photosensitive sun rash due to its ability to absorb UV light.

What type of glycoside is found in the Apiacia family (Cellery, Fennell, etc.) as well as AGED red and white Clover?

Lactone Glycosides such as Hydroxycoumarins. These are vitamine K antagonists which means they are anticoagulants. Photosensitivity is an issue.

What is the glycoside found in the seeds of Figs and Celery?

A Lactone glycoside called Psoralen - a pyranocumarin. Psoralen occurs naturally in the seeds of Psoralea corylifolia, as well as in the common Fig, celery, parsley and West Indian satinwood. It is widely used in PUVA (=Psoralen +UVA) treatment for psoriasis, eczema, vitiligo, and cutaneous T-cell lymphoma.

What type of glycoside is found in Ruta and Citris Bergamia?

The Lactone glycoside Bergapten. It can also be found in Parsley, Anise and Lovage. These are furanocumarins. (has a 5 C ring). Is is used in the treatment of Vitiligo and Psoriasis. It is also an anitspasmotic and vascular tonic. It benefits connective tissue as well.

What type of glycosides are found in Ammi Visnaga (aka Khella)?

Khella is part of the carrot family (related to queen anne's lace). It contains the Lactone glycoside, who's aglycone is called Khellin. Khellin is a vasodilator of coronary and respiratory smooth muscle and is used in the treatment of asthma. A drug called Intal has been developed based on Khellin. Similar to Quercitin. Photosensitivity an issue.

What are the properties of Phenolic glycosides?

They are antibiotics. They kill fungus, bacteria, parasites and candida. An example would be Uva Ursi.

What type of glycoside is in Uva Ursi? What is the name of its aglycone?

Uva Ursi contains a phenolic glycoside called Arbutin. The aglycone is called Hydroquinone.

What are the properties of Tannin glycosides?

They bind and heal wounds. They are polymerized by Polyphenol oxidase to form large molecules that are not digested. Good for healing the epithelium. They can be found in tea leaves and witch hazel.

What are the properties of Flavonoid glycosides?

They are ant-ioxidents that strengthen veins, are good for treating allergies, high blood pressure, suppress cancer genes and strengthen collagen. An example is Quercetin.

What are the properties of Aldehyde glycosides?

Used for flavorings -an example would be vanilla.

What are the basic functions of steroids in nature?

1. Reproduction in mammals and insects (esp. molting)
2. Used as anti-inflammatory and anabolic agents
3. Vit. D
4. Billiary system: contains fatty steroids that help emulsify other fats.
5. Cholesterol: used as precursor for hormones and as a patch for damaged artery walls.

Where are the sugar and R group located on the steroidal backbone?

R is at C17 and the sugar is at C3.

What type of steroid has an R=6 C lactone ring?

A Bufadienolide - taken originally from the skin of toads.

What type of steriod has an R=5 C lactone ring?

A Cardenolide - these are more prevalent in nature.

What are the properties of Cardiac glycosides?

These glycosides have powerful effects on the heart and are used to treat atrial fibrilation, flutter and congestive heart failure (CHF):
1. Positively Ionotropic: increase the strength of contraction - blood is pumped more efficiently which can decrease edema and fluid congestion around the heart.
2. Negatively chronotropic: slows down the rate of contractions - allows weak heart tissue a longer time to rest and recover between contractions.
3. Speeds up filtration rate of the kidneys - reducing edema and fluid build up due to excess salts.

What is Congestive Heart Failure?

Failure of the heart to pump blood at a sufficient rate to metabolizing tissues. Reduced contractility of the heart muscle, esp. the ventricles. Sx: shortness of breath, Ascites, pulmonary edema, low BP, swelling in the limbs, Renal failure.

What is the mechanism of action of the Cardiac glycosides?

1. Inhibits Na+/K+/ATPase pump: increases Na+ in the cell, decreases K+ in the cell, Increases free Ca++ in the cell.
This reduces the cardiac cell membrane potential so that it is easier to trigger a contraction. Reduction in stress load on heart muscle.

What effect does the increase in free calcium ions in cardiac cells have on the heart?

More free Ca++ will bind to more Troponin. When Troponin in bound, it frees up the actin so that myocin can bind to it and the cardiac muscle will contract. Increased free Ca++ equals stronger contractions.

What is the proper dosing protocol for cardiac glycosides? What is the main symptom of toxicity?

1. Give patient an initial load
2. Titrate dose with amount metabolized.
Continuous blood monitoring.
Note: 50-60% Toxic dose= Therapeutic dose
Toxicity: Ventricular extrasystoles (rapid hear rate in the ventricles only, not the atria. Vomiting -contain Anthrquinone glycosides that will make you vomit the herbs up if a toxic dose is taken.

How does the sugar portion of the cardiac glycoside function in the body? What is the significance of hydroxyl groups on the molecule?

The sugar portion of the molecule confers solubility and helps it to be properly distributed in the body. The more -OH groups, the more:
1. rapid action
2. water soluble
3. easily excreted, thus SAFER (but has to be dosed continuously).

What are the three classes of molecules that can be useful in treating CHF?

1. Cardiac glycosides - (Digitalis, Adonis vernalis, Strophanthus, squill, convillaria) the most effective, but also the most dangerous. They are fat soluble, so the body takes a long time to excrete them.
2. Phosphodiesterase inhibitors - (Crutagus/Hawthorne, Cactus) Indirectly increase cAMP, which increases free Ca++ in the cell leading to stronger contractions of the heart tissue.
3. Direct c AMP stimulants - (Forskolin from Coleus/Indian oregano) directly increases cAMP.

What type of Glycoside is in Digitalis ssp. (Foxglove)? What are the aglycones? What are the basic properties of the herb?

Cardiac Glycosides - The most lipid soluble with a half-life of 2-3 weeks. It is very easy to overdose. The medicine is made of the basal rosette of the 1st year leaves. Used historically to treat Dropsy. There are at least 30 glycosides, the main 2 are: Digitoxin and Gitoxin. The herb ranges widely in concentration of glycosides, therefore standardization is very important for optimum dosing control.

What is the dosing protocol for Digitallis ssp?

To treat CHF, superventricular tachycardia, atrial flutter and atrial fibrillation:
1st dose: 1-2grams USP crude drug
Maintenance: 100-200mg
Note: reduce dose by 25% for the elderly or overly skinny, more for obese. Onset of action: 2-4 hrs. Dissipation of drug: 2-3 weeks.

What is the allopathic drug derived from Digitallis?

Digitoxin. 800 micrograms, then 200 every 6-8 hrs for 2-3 doses, then maint. dose of 50-200 ug per day.

What type of glycosides are in Strophanthus?

The Cardiac glycosides Oubain and Strophanthin-G. Used for CHF without valvular disease (weak heart, rapid pulse, low BP, dyspnea). These have a half-life of only 2 hours. Very fast acting. Can be used for elderly and low vitality patients. Toxicity still an issue, so blood monitoring important.

What type of glycoside is in Adonis Vernalis (Pheasant's eye)?

Cardiac glycoside - Buttercup family with Goldenseal and echinaecia. Use a very low dose: 5-10 drops tincture (highly toxic). Increases cardiac contractility and decreases heart rate.

What type of glycosides are in Squill (Urginea maritime)?

Cardiac glycosides - part of the Lilly family. The primary glycoside is Scillaren A, the aglycone is Scillarenin, which is a Bufadienolide. Vinegar is the best solvent -Acetal of Scilla. Can cause liver damage in large doses.

What type of glycosides are in Convallaria (Lilly of the Valley)?

Convallaria contains some of the most water soluble, "safest" cardiac glycosides - Convallotoxin, convalloside & convallotoxol. It also is high in Flavinoids, which strengthen tissue and anthraquinones, so excessive doses cause diarrhea.

What type of cardiac patient would Lilly of the Valley be well suited for?

Used for patients with cardiac irregularities with mechanical impediments. Dx Mitral valve insufficiency or feeble circulation with low atrial tension.

What is the CCC formula?

Popularized by Dr. Basyr: The CCC formula contains:
1. Crateagus (Hawthorne)- Co Q10
2. Cactus
3. Convallaria (Lily of the Valley)
Crateagus and Cactus do not have cardiac glycosides. They have vasoactive amines and flavinoids that help weak and feeble heart tissue.
Dosing: 5-30 drops of the 1:5 tincture per day.

What type of glycosides are in Oleander?

Cardiac glycosides: Oleandrin, Digitalium and Gitoxigenin. Used in the tropics where Digitalis doesn't grow.

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