Stigmasterol
Encyclopedia
Stigmasterol is one of a group of plant sterols, or phytosterols, that include beta-sitosterol
, campesterol
, ergosterol
(provitamin D2), brassicasterol
, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol
. Phytosterols are insoluble in water but soluble in most organic solvents and contain one alcohol functional group.
Stigmasterol is an unsaturated plant sterol
occurring in the plant fats or oils of soybean
, calabar bean
, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng
. Stigmasterol is also found in various vegetables, legumes, nuts
, seeds
, and unpasteurized milk
. Pasteurization
will inactivate stigmasterol. Edible oils contains higher amount than vegetables.
Stigmasterol is used as a precursor in the manufacture of synthetic progesterone
, a valuable human hormone
that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen
effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D3.
Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate
, breast
, and colon cancers. Studies have also indicated that a diet
high in phytoesterols may inhibit the absorption of cholesterol and lower serum cholesterol levels by competing for intestinal absorption. Studies with laboratory animals fed stigmasterol found that both cholesterol and sitosterol absorption decreased 23% and 30%, respectively, over a 6-week period. It was demonstrated that it inhibits several pro-inflammatory and matrix degradation mediators typically involved in osteoarthritis
-induced cartilage
degradation. It also possesses potent antioxidant
, hypoglycemic and thyroid
inhibiting properties.
Phytosterols normally are broken down in the bile
.
Beta-sitosterol
β-Sitosterol is one of several phytosterols with chemical structures similar to that of cholesterol. Sitosterols are white, waxy powders with a characteristic odor...
, campesterol
Campesterol
Campesterol is a phytosterol whose chemical structure similar to that of cholesterol. Many vegetables, fruits, nuts and seeds contain campesterol, but in low concentrations. Banana, pomegranate, pepper, coffee, grapefruit, cucumber, onion, oat, potato and lemon grass are few examples of common...
, ergosterol
Ergosterol
Ergosterol is a sterol found in fungi, and named for ergot, a common name for the members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol does not occur in plant or animal cells...
(provitamin D2), brassicasterol
Brassicasterol
Brassicasterol is a 28-carbon sterol synthesised by several unicellular algae and some terrestrial plants, e.g., oilseed rape...
, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol
Cholesterol
Cholesterol is a complex isoprenoid. Specifically, it is a waxy steroid of fat that is produced in the liver or intestines. It is used to produce hormones and cell membranes and is transported in the blood plasma of all mammals. It is an essential structural component of mammalian cell membranes...
. Phytosterols are insoluble in water but soluble in most organic solvents and contain one alcohol functional group.
Stigmasterol is an unsaturated plant sterol
Sterol
Sterols, also known as steroid alcohols, are a subgroup of the steroids and an important class of organic molecules. They occur naturally in plants, animals, and fungi, with the most familiar type of animal sterol being cholesterol...
occurring in the plant fats or oils of soybean
Soybean
The soybean or soya bean is a species of legume native to East Asia, widely grown for its edible bean which has numerous uses...
, calabar bean
Calabar bean
The Calabar bean is the seed of a leguminous plant, Physostigma venenosum, a native of tropical Africa, poisonous to humans. It derives the first part of its scientific name from a curious beak-like appendage at the end of the stigma, in the centre of the flower; this appendage, though solid, was...
, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng
American Ginseng
American ginseng, Panax quinquefolius, is a herbaceous perennial plant in the ivy family, commonly used as Chinese or herbal medicine.It is native to eastern North America, though it is also cultivated in places such as China....
. Stigmasterol is also found in various vegetables, legumes, nuts
Nut (fruit)
A nut is a hard-shelled fruit of some plants having an indehiscent seed. While a wide variety of dried seeds and fruits are called nuts in English, only a certain number of them are considered by biologists to be true nuts...
, seeds
SEEDS
SEEDS is a voluntary organisation registered under the Societies Act of India....
, and unpasteurized milk
Raw milk
Raw milk is milk that has not been pasteurized or homogenized.-History:Humans consumed raw milk exclusively prior to the industrial revolution and the invention of the pasteurization process in 1864. During the industrial revolution large populations congregated into urban areas detached from the...
. Pasteurization
Pasteurization
Pasteurization is a process of heating a food, usually liquid, to a specific temperature for a definite length of time, and then cooling it immediately. This process slows microbial growth in food...
will inactivate stigmasterol. Edible oils contains higher amount than vegetables.
Stigmasterol is used as a precursor in the manufacture of synthetic progesterone
Progesterone
Progesterone also known as P4 is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy and embryogenesis of humans and other species...
, a valuable human hormone
Hormone
A hormone is a chemical released by a cell or a gland in one part of the body that sends out messages that affect cells in other parts of the organism. Only a small amount of hormone is required to alter cell metabolism. In essence, it is a chemical messenger that transports a signal from one...
that plays an important physiological role in the regulatory and tissue rebuilding mechanisms related to estrogen
Estrogen
Estrogens , oestrogens , or œstrogens, are a group of compounds named for their importance in the estrous cycle of humans and other animals. They are the primary female sex hormones. Natural estrogens are steroid hormones, while some synthetic ones are non-steroidal...
effects, as well as acting as an intermediate in the biosynthesis of androgens, estrogens, and corticoids. It is also used as the precursor of vitamin D3.
Research has indicated that stigmasterol may be useful in prevention of certain cancers, including ovarian, prostate
Prostate
The prostate is a compound tubuloalveolar exocrine gland of the male reproductive system in most mammals....
, breast
Breast
The breast is the upper ventral region of the torso of a primate, in left and right sides, which in a female contains the mammary gland that secretes milk used to feed infants.Both men and women develop breasts from the same embryological tissues...
, and colon cancers. Studies have also indicated that a diet
Diet (nutrition)
In nutrition, diet is the sum of food consumed by a person or other organism. Dietary habits are the habitual decisions an individual or culture makes when choosing what foods to eat. With the word diet, it is often implied the use of specific intake of nutrition for health or weight-management...
high in phytoesterols may inhibit the absorption of cholesterol and lower serum cholesterol levels by competing for intestinal absorption. Studies with laboratory animals fed stigmasterol found that both cholesterol and sitosterol absorption decreased 23% and 30%, respectively, over a 6-week period. It was demonstrated that it inhibits several pro-inflammatory and matrix degradation mediators typically involved in osteoarthritis
Osteoarthritis
Osteoarthritis also known as degenerative arthritis or degenerative joint disease, is a group of mechanical abnormalities involving degradation of joints, including articular cartilage and subchondral bone. Symptoms may include joint pain, tenderness, stiffness, locking, and sometimes an effusion...
-induced cartilage
Cartilage
Cartilage is a flexible connective tissue found in many areas in the bodies of humans and other animals, including the joints between bones, the rib cage, the ear, the nose, the elbow, the knee, the ankle, the bronchial tubes and the intervertebral discs...
degradation. It also possesses potent antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
, hypoglycemic and thyroid
Thyroid
The thyroid gland or simply, the thyroid , in vertebrate anatomy, is one of the largest endocrine glands. The thyroid gland is found in the neck, below the thyroid cartilage...
inhibiting properties.
Phytosterols normally are broken down in the bile
Bile
Bile or gall is a bitter-tasting, dark green to yellowish brown fluid, produced by the liver of most vertebrates, that aids the process of digestion of lipids in the small intestine. In many species, bile is stored in the gallbladder and upon eating is discharged into the duodenum...
.
See also
- CharantinCharantinCharantin is a chemical substance obtained from the Asian bitter melon , reputed to be responsible for the hypoglycaemic properties of those plants. It was identified by Lolitkar and Rao in 1960. It was also found in the similar African species M. foetida, by A...
, a stigmasteryl glucoside found in the bitter melonBitter melonMomordica charantia, called bitter melon or bitter gourd in English, is a tropical and subtropical vine of the family Cucurbitaceae, widely grown in Asia, Africa, and the Caribbean for its edible fruit, which is among the most bitter of all fruits...
plant. - StigmastanolStigmastanolStigmastanol is a phytosterol found in a variety of plant sources. Similar to sterol esters and stanol esters, stigmasterol inhibits the absorption of cholesterol from the diet. Animal studies suggest that it also inhibits biosynthesis of cholesterol in the liver....
, a closely related phytosterol