PHCH 2202: Pharmacognosy and Plant Chemistry - Endocrine Products

Hormones

• Also known as chemical messengers
• Substances secreted by endocrine or ductless glands of animals
• History: In 1891, Horsley showed that patients with myxoedema and cretinism benefited from the administration of animal thyroid glands

Hormone Therapy vs Organotherapy

• Hormone therapy: using the active principles
• Organotherapy: using the glands or more or less crude preparations of them

Classes of Hormones

Steroid Hormones

• Insoluble in water and transported by transport proteins in blood, resulting in longer circulation than peptide hormones
• Steroid nucleus: any compound having a cyclopentano-perhydrophenanthrene (CPPP) nucleus
• Alpha and beta configuration

Biosynthesis of Steroids

• Formed from isopentenyl pyrophosphate
• Cholesterol is not necessarily the precursor, but its formation is a general mechanism of steroid biosynthesis

Forms of Steroids

• Sterols
• Bile acids
• Cardiac glycosides
• Steroid hormones

Sterols

• Solids and high molecular weight (HMW) with 27-29 carbon atoms
• First isolated from human gallstones
• Other sources: algae, fungi, actinomyces

Examples of Sterols

• Ergosterol: 28 carbon structure, principal fungi sterol, also known as provitamin D2 (exposure to UV produces Vitamin D)
• Beta-Sitosterol: 29 carbon structure, most common plant sterol, from plant-derived oils (corn, cottonseed, etc.), used to treat atherosclerosis and has anti-hypercholesterolemic effects

Bile Acids

• Cholesterol → C24 steroids (where C24 is a carboxyl) → collected in bile and referred to as bile acids
• Conjugated bile acids: released into the duodenum to emulsify meals for fat absorption

Examples of Bile Acids

• Deoxycholic acid (from cholic acid)
• Lithocholic acid (from chenodesoxycholic acid)
• Primary bile acids (liver): cholic acid and chenodesoxycholic acid
• Ox bile extract: partial evaporation of fresh ox bile, precipitation of the mucus and albuminous matter with alcohol, and consequent evaporation (evaporate to dryness at < 80°C), contains Na salts of glycholic acid and taurocholic acid equivalent to not less than 45% cholic acid, used as a laxative

Chenodesoxycholic Acid

• Also known as Chenodiol
• Suppresses hepatic synthesis of cholesterol and cholic acid, leading to biliary cholesterol desaturation and dissolution of cholesterol gallstones
• Types of cholesterol gallstones: radiolucent and radiopaque (calcified)

Cardiac Glycosides

• Review notes on cardiac glycosides as previously discussed

Steroid Hormones

Sex Hormones

• Produced primarily in the gonads
• Mediate the growth, development, maintenance, and function of the reproductive tract and accessory sex organs
• 3 categories:
  • Estrogen and progesterone: female reproductive tract
  • Androgen: male reproductive organs

Adrenocorticoid Hormones

• Produced by the outer cortical portion of the adrenal glands
• 2 classes:
  • Mineralocorticoids: affect the excretion of fluid and electrolytes with subsequent sodium and potassium retention
  • Glucocorticoids: affect intermediary metabolism
• Examples:
  • Aldosterone (principal) and desoxycorticosterone (mineralocorticoids)
  • Cortisone and hydrocortisone (protein and carb metabolism)

Learn about endocrine products, hormone therapy, and organotherapy in pharmacognosy and plant chemistry. Understand the classification, history, and benefits of hormones as chemical messengers. A comprehensive lesson for pharmacy students.