InChI=1S/C27H46O3/c1- 16(2)6-9-23(29)17(3)25-24(30)15-22-20-8-7-18-14-19(28)10-12-26(18,4)21(20)11-13-27(22,25)5/h7,16-17,19-25,28-30H,6,8-15H2,1-5H3/t17-,19+,20-,21+,22+,23+,24+,25+,26+,27+/m1/s1 |
| IIGMATMTMWUMJV-QKFQEXBKSA-N |
| [H][C@]1([C@H](C)[C@@H](O)CCC(C)C)[C@@H](O)C[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C |
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plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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View more via ChEBI Ontology
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(22S)-cholest-5-ene-3β,16β,22-triol
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(16S,22S)-16,22-dihydroxycholesterol
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SUBMITTER
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(16S,22S)-dihydroxycholesterol
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UniProt
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(3S,16S,22S)-cholest-5-ene-3,16,22-triol
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SUBMITTER
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(3S,22S)-cholesta-5-ene-3β,16β,22-triol
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ChEBI
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16S,22S-dihydroxycholesterol
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SUBMITTER
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Zhou C, Yang Y, Tian J, Wu Y, An F, Li C, Zhang Y (2022)
22R- but not 22S-hydroxycholesterol is recruited for diosgenin biosynthesis.
The Plant journal : for cell and molecular biology 109, 940-951 [PubMed:34816537]
[show Abstract]
Diosgenin is an important compound in the pharmaceutical industry and it is biosynthesized in several eudicot and monocot species, herein represented by fenugreek (a eudicot), and Dioscorea zingiberensis (a monocot). Formation of diosgenin can be achieved by the early C22,16-oxidations of cholesterol followed by a late C26-oxidation. This study reveals that, in both fenugreek and D. zingiberensis, the early C22,16-oxygenase(s) shows strict 22R-stereospecificity for hydroxylation of the substrates. Evidence against the recently proposed intermediacy of 16S,22S-dihydroxycholesterol in diosgenin biosynthesis was also found. Moreover, in contrast to the eudicot fenugreek, which utilizes a single multifunctional cytochrome P450 (TfCYP90B50) to perform the early C22,16-oxidations, the monocot D. zingiberensis has evolved two separate cytochrome P450 enzymes, with DzCYP90B71 being specific for the 22R-oxidation and DzCYP90G6 for the C16-oxidation. We suggest that the DzCYP90B71/DzCYP90G6 pair represent more broadly conserved catalysts for diosgenin biosynthesis in monocots. | Christ B, Xu C, Xu M, Li FS, Wada N, Mitchell AJ, Han XL, Wen ML, Fujita M, Weng JK (2019)
Repeated evolution of cytochrome P450-mediated spiroketal steroid biosynthesis in plants.
Nature communications 10, 3206 (Source: SUBMITTER) [PubMed:31324795]
[show Abstract]
Diosgenin is a spiroketal steroidal natural product extracted from plants and used as the single most important precursor for the world steroid hormone industry. The sporadic occurrences of diosgenin in distantly related plants imply possible independent biosynthetic origins. The characteristic 5,6-spiroketal moiety in diosgenin is reminiscent of the spiroketal moiety present in anthelmintic avermectins isolated from actinomycete bacteria. How plants gained the ability to biosynthesize spiroketal natural products is unknown. Here, we report the diosgenin-biosynthetic pathways in himalayan paris (Paris polyphylla), a monocot medicinal plant with hemostatic and antibacterial properties, and fenugreek (Trigonella foenum-graecum), an eudicot culinary herb plant commonly used as a galactagogue. Both plants have independently recruited pairs of cytochromes P450 that catalyze oxidative 5,6-spiroketalization of cholesterol to produce diosgenin, with evolutionary progenitors traced to conserved phytohormone metabolism. This study paves the way for engineering the production of diosgenin and derived analogs in heterologous hosts. | Mimaki Y, Kuroda M, Yokosuka A, Sashida Y (2001)
Five new polyoxygenated cholestane bisdesmosides from the bulbs of Galtonia candicans.
Journal of natural products 64, 1069-1072 [PubMed:11520229]
[show Abstract]
Two new cholestane bisdesmosides (1, 2) based upon (22S)-cholest-5-ene-3 beta,16 beta,22-triol with an acetyl group at the sugar moiety and three new ones (3-5) based upon (22S)-cholest-5-ene-1 beta,3 beta,16 beta,22-tetrol, along with a known cholestane glycoside, were isolated from the bulbs of Galtonia candicans. The structures of the new compounds were determined by spectroscopic analysis and chemical transformations. |
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