DHSA

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title: "DHSA" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["secosteroids"] topic_path: "general/secosteroids" source: "https://en.wikipedia.org/wiki/DHSA" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 443680947 | ImageFile = DHSA.svg | ImageSize = 120px | IUPACName = 3,4-Dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione | SystematicName = (3aS,4S,7aS)-4-[2-(2,3-Dihydroxy-6-methylphenyl)ethyl]-7a-methylhexahydro-1H-indene-1,5(4H)-dione | OtherNames = |Section1={{Chembox Identifiers | CASNo=2168-61-8 | CASNo_Ref = | PubChem=440483 | ChEBI_Ref = | ChEBI = 15896 | DrugBank_Ref = | DrugBank = DB08542 | KEGG = C04793 | SMILES=CC1=C(C(=C(C=C1)O)O)CCC2C3CCC(=O)C3(CCC2=O)C | ChemSpiderID_Ref = | ChemSpiderID = 389410 | StdInChI_Ref = | StdInChI=1S/C19H24O4/c1-11-3-7-16(21)18(23)12(11)4-5-13-14-6-8-17(22)19(14,2)10-9-15(13)20/h3,7,13-14,21,23H,4-6,8-10H2,1-2H3/t13-,14-,19-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = YUHVBHDSVLKFNI-NJSLBKSFSA-N |Section2={{Chembox Properties | Formula=C19H24O4 | MolarMass=316.39146 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = 3,4-DHSA is an organic compound which is the intermediate product of the metabolism of cholesterol, by the bacteria most commonly responsible for tuberculosis (Mycobacterium tuberculosis). 3,4-DHSA is an acronym for 3,4-dihydroxy-9,10-seco-androst-1,3,5(10)-triene-9,17-dione, the official name of this substance. It is classified as a secosteroid, since one of the four rings of cholesterol from which it is derived is broken.

3,4-DHSA is a catecholic intermediate (a compound containing an aromatic ring with two adjacent hydroxyl groups) produced by M. tuberculosis during the breakdown of cholesterol. 3,4-DHSA is also produced by other bacteria such as Comamonas testosteroni.

A particular type of enzyme known as extradiol dioxygenase is responsible for the oxidation and ring opening of 3,4-DHSA to 4,9-DSHA (see metabolic scheme below). M. tuberculosis bacteria that are deficient in this enzyme are less lethal than wild-type bacteria. 3,4-DHSA itself appears to be toxic to the bacteria while the breakdown products of 3,4-DHSA can be used as energy source by the bacteria. Hence blocking the oxidation of 3,4-DHSA by the extradiol dioxygenase enzyme may be useful in the treatment of tuberculosis.

A crystal structure of DHSA in complex with M. tuberculosis iron-dependent extradiol dioxygenase has been determined.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/6/6b/DHSA_metabolism.tif" caption="Synthesis and degradation of 3,4-DHSA."] ::

References

References

  1. (March 2009). "Studies of a Ring-Cleaving Dioxygenase Illuminate the Role of Cholesterol Metabolism in the Pathogenesis of Mycobacterium tuberculosis". PLOS Pathog..
  2. (November 2004). "Steroid degradation gene cluster of Comamonas testosteroni consisting of 18 putative genes from meta-cleavage enzyme gene tesB to regulator gene tesR". Biochem. Biophys. Res. Commun..
  3. (October 2004). "The genes encoding the hydroxylase of 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione in steroid degradation in Comamonas testosteroni TA441". J. Steroid Biochem. Mol. Biol..

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secosteroids