Phytosteroids, also known as plant steroids, are

naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

s that are found in

plant Plants are the eukaryotes that form the Kingdom (biology), kingdom Plantae; they are predominantly Photosynthesis, photosynthetic. This means that they obtain their energy from sunlight, using chloroplasts derived from endosymbiosis with c ...

s. Examples include

digoxin Digoxin (better known as digitalis), sold under the brand name Lanoxin among others, is a medication used to treat various heart disease, heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. ...

digitoxin Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, whic ...

diosgenin Diosgenin, a phytosteroid sapogenin, is the product of hydrolysis by acids, strong bases, or enzymes of saponins, extracted from the tubers of '' Dioscorea'' wild yam species, such as the Kokoro. It is also present in smaller amounts in a num ...

, and

guggulsterone Guggulsterone is a phytosteroid found in the resin of the guggul plant, ''Commiphora mukul''. Guggulsterone can exist as either of two stereoisomers, ''E''-guggulsterone and ''Z''-guggulsterone. In humans, it acts as an antagonist of the farnesoi ...

, as well as

phytosterol Phytosterols are phytosteroids, similar to cholesterol, that serve as structural components of biological membranes of plants. They encompass plant sterols and stanol ester, stanols. More than 250 sterols and related compounds have been identified ...

s like β-sitosterol.

Industrial use

Steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

pharmaceuticals that are identical or similar to human

steroid hormone A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into two classes: corticosteroids (typically made in the adrenal cortex, hence ''cortico-'') and sex steroids (typically made in the gonads or placenta). Wit ...

s are very widely used in medicine. However, the four-ring structure of a steroid is quite expensive to replicate using direct synthetic methods. In 1938–1940, American chemist

Russell Earl Marker Russell Earl Marker (March 12, 1902 – March 3, 1995) was an American chemist who invented the octane rating system when he was working at the Ethyl Corporation. Later in his career, he went on to found a steroid industry in Mexico when he s ...

developed the process known as

Marker degradation The Marker degradation is a three-step chemical synthesis, synthetic route in steroid chemistry developed by American chemist Russell Earl Marker in 1938–1940. It is used for the production of cortisone and mammalian sex hormones (progesterone, e ...

, which converts

from Mexican ''

Dioscorea ''Dioscorea'' is a genus of over 600 species of flowering plants in the family Dioscoreaceae, native throughout the tropical and warm temperate regions of the world. The vast majority of the species are tropical, with only a few species extendin ...

'' yams into

16-dehydropregnenolone acetate 16-Dehydropregnenolone acetate (16-DPA) is a chemical compound used as an intermediate or synthon in the production of many semisynthetic steroids. As 7-ACA is for cephalosporins and 6-APA is for penicillins, 16-DPA is for steroids. While it is ...

, which has a four-ring structure and can be used to synthesize commonly used steroid hormones. Marker's process reduced the price of

progesterone Progesterone (; P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the ma ...

from $80/gram in early 1944 to $2/gram in 1951. Also in 1940, American chemist

Percy Lavon Julian Percy Lavon Julian (April 11, 1899 – April 19, 1975) was an American research chemist and a pioneer in the chemical synthesis of medicinal drugs from plants. Julian was the first person to synthesize the natural product physostigmine, and a pio ...

discovered a process to convert a much more abundant phytosteroid --

stigmasterol Stigmasterol – a plant sterol (''phytosterol'') – is among the most abundant of plant sterols, having a major function to maintain the structure and physiology of cell membranes. In the European Union, it is a food additive listed with E nu ...

from

soybean The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean. Soy is a staple crop, the world's most grown legume, and an important animal feed. Soy is a key source o ...

-- into progesterone. Stigmasterol is a byproduct of soybean oil refinement. His process was improved by

Padmanabhan Sundararaman Notable people with the name Padmanabhan include: * C. M. Padmanabhan Nair (?–1977), an Indian politician *Dayal Padmanabhan, an Indian film director and producer * Govindarajan Padmanabhan, a renowned biochemist and a pioneer in Indian biotechn ...

and

Carl Djerassi Carl Djerassi (October 29, 1923 – January 30, 2015) was an Austrian-born Bulgarian-American pharmaceutical chemist, novelist, playwright and co-founder of Djerassi Resident Artists Program with Diane Wood Middlebrook. He is best known for his ...

in 1977, just as stocks of wild Mexican yam became depleted. Soy stigmasterol soon replaced yam diosgenin as the main starting material for hormone production globally.

References

Steroids {{steroid-stub