Diosgenin, a
phytosteroid sapogenin
Sapogenins are the aglycones, or non-saccharide, portions of the family of natural products known as saponins. Sapogenins contain steroid or other triterpene frameworks as their key organic feature. For example, steroidal sapogenins such as tigge ...
, 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
is a novel by the Japanese author Natsume Sōseki. It was first published in 1914 in serial form in the Japanese newspaper ''Asahi Shimbun''. The title translated literally means "heart". The word contains shades of meaning—notions of the he ...
. The sugar-free (
aglycone) product of such hydrolysis, diosgenin is used for the commercial synthesis of
cortisone,
pregnenolone
Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocor ...
,
progesterone, and other steroid products.
Sources
It is present in detectable amounts in ''
Costus speciosus
''Cheilocostus speciosus'', or crêpe ginger, is a species of flowering plant in the family Costaceae. Some botanists have now revived the synonym ''Hellenia speciosa'' for this species.
It is native to southeast Asia and surrounding regions, ...
'', ''
Smilax menispermoidea
''Smilax'' is a genus of about 300–350 species, found in the tropics and subtropics worldwide. In China for example about 80 are found (39 of which are endemic), while there are 20 in North America north of Mexico. They are climbing flowering ...
'', ''
Helicteres isora'', species of ''
Paris
Paris () is the capital and most populous city of France, with an estimated population of 2,165,423 residents in 2019 in an area of more than 105 km² (41 sq mi), making it the 30th most densely populated city in the world in 2020. Si ...
'', ''
Aletris'', ''
Trigonella
''Trigonella'' is a genus from the family Fabaceae. The best known member is the herb fenugreek. Members of the genus occur naturally in the Canary Islands, southern Europe, nontropical Africa, western and central Asia, the Indian subcontinent, ...
'', and ''
Trillium'', and in extractable amounts from many species of ''
Dioscorea'' – ''
D. althaeoides'', ''
D. colletti'', ''
D. composita'',
''
D. floribunda'', ''
D. futschauensis'', ''
D. gracillima'', ''
D. hispida'', ''
D. hypoglauca'', ''
D. mexicana'',
''
D. nipponica'', ''
D. panthaica'', ''
D. parviflora'', ''
D. septemloba'', and ''
D. zingiberensis''.
Industrial uses
Diosgenin is a precursor for several hormones, starting with the
Marker degradation process, which includes synthesis of
progesterone.
The process was used in the early manufacturing of
combined oral contraceptive pill
The combined oral contraceptive pill (COCP), often referred to as the birth control pill or colloquially as "the pill", is a type of birth control that is designed to be taken orally by women. The pill contains two important hormones: proges ...
s.
References
External links
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{{Saponins
Estrogens
Hormonal contraception
Progestogens
Spiro compounds
Steroids
Tetrahydrofurans
Tetrahydropyrans