Diosgenin, a
phytosteroid sapogenin
Sapogenins are aglycones (non-saccharide moieties) of saponins, a large family of natural products. Sapogenins contain steroid or other triterpene frameworks as their key organic feature. For example, steroidal sapogenins such as tiggenin, neo ...
, is the product of hydrolysis by acids, strong bases, or enzymes of
saponins
Saponins (Latin ''sapon'', 'soap' + ''-in'', 'one of') are bitter-tasting, usually toxic plant-derived secondary metabolites. They are Organic compound, organic chemicals that become foamy when agitated in water and have high Molar mass, molecul ...
, extracted from the
tubers
Tubers are a type of enlarged structure that plants use as storage organs for nutrients, derived from stems or roots. Tubers help plants perennate (survive winter or dry months), provide energy and nutrients, and are a means of asexual reprod ...
of ''
Dioscorea''
wild yam species, such as the
Kokoro. It is also present in smaller amounts in a number of other species. The sugar-free (
aglycone
An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid
A steroid is an organic compoun ...
) product of such hydrolysis, diosgenin is used for the commercial synthesis of
cortisone
Cortisone is a pregnene (21-carbon) steroid hormone. It is a naturally-occurring corticosteroid metabolite that is also used as a pharmaceutical prodrug. Cortisol is converted by the action of the enzyme corticosteroid 11-beta-dehydrogenase ...
,
pregnenolone,
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 ...
, and other steroid products.
Sources
It is present in detectable amounts in ''
Costus speciosus'', ''
Smilax menispermoidea'', ''
Helicteres isora'', species of ''
Paris
Paris () is the Capital city, capital and List of communes in France with over 20,000 inhabitants, largest city of France. With an estimated population of 2,048,472 residents in January 2025 in an area of more than , Paris is the List of ci ...
'', ''
Aletris'', ''
Trigonella'', and ''
Trillium
''Trillium'' (trillium, wakerobin, toadshade, tri flower, birthroot, birthwort, and sometimes "wood lily") is a genus of about fifty flowering plant species in the family Melanthiaceae. ''Trillium'' species are native to temperate regions of No ...
'', 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 chemical precursor for several hormones, starting with the
Marker degradation process, which includes synthesis 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 ...
.
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 Oral administration, taken orally by women. It is the oral form of combi ...
s.
Diosgenin in
dietary supplements
A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources, or that are synthetic ...
is not a physiological precursor to
estradiol
Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible ...
or
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 ...
, and the use of such products as
wild yam has no estrogenic hormonal activity in the human body.
[Medigović I, Ristić N, Živanović J, Šošić-Jurjević B, Filipović B, Milošević V, Nestorović ]
“Diosgenin does not express estrogenic activity: a uterotrophic assay”
Can J Physiol Pharmacol. 2014 Apr;92(4):292-8. doi: 10.1139/cjpp-2013-0419. Epub 2014 Feb 5. PMID 24708211
See also
*
List of neurosteroids
**
Spirostanes
References
External links
*
{{Saponins
Estrogens
Hormonal contraception
Progestogens
Spiro compounds
Steroids
Tetrahydrofurans
Tetrahydropyrans