| Revision as of 08:30, 3 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[use← Previous edit |
Latest revision as of 17:11, 18 January 2024 edit undo100.15.190.93 (talk)No edit summaryTag: Manual revert |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 448193489 |
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| Watchedfields = changed |
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| verifiedrevid = 400871114 |
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| IUPAC_name = 26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside |
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| IUPAC_name = 26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside |
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| image = Protodioscin.png |
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| image = Protodioscin.png |
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| width = 340 |
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| width = 340 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_status = Legal |
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| legal_status = Legal |
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| routes_of_administration = Oral |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number = 55056-80-9 |
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| CAS_number = 55056-80-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = D0LC3PH24P |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| ATC_suffix = |
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| ATC_suffix = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 390467 |
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| ChemSpiderID = 390467 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=51 | H=84 | O=22 |
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| C=51 | H=84 | O=22 |
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| molecular_weight = 1049.199 g/mol |
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| smiles = C12(C32(CC43CC=C54(CC(C5)O6((((O6)CO)O7((((O7)C)O)O)O)O)O8((((O8)C)O)O)O)C)C)O1(CC(C)CO9((((O9)CO)O)O)O)O |
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| smiles = C12(C32(CC43CC=C54(CC(C5)O6((((O6)CO)O7((((O7)C)O)O)O)O)O8((((O8)C)O)O)O)C)C)O1(CC(C)CO9((((O9)CO)O)O)O)O |
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| InChI = 1/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1 |
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| InChIKey = LVTJOONKWUXEFR-UEZXSUPNBY |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1 |
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| StdInChI = 1S/C51H84O22/c1-20(19-65-45-39(60)38(59)35(56)30(17-52)69-45)9-14-51(64)21(2)32-29(73-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)68-48-44(72-47-41(62)37(58)34(55)23(4)67-47)42(63)43(31(18-53)70-48)71-46-40(61)36(57)33(54)22(3)66-46/h7,20-23,25-48,52-64H,8-19H2,1-6H3/t20-,21+,22+,23+,25+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42+,43-,44-,45-,46+,47+,48-,49+,50+,51-/m1/s1 |
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| StdInChIKey = LVTJOONKWUXEFR-UEZXSUPNSA-N |
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| StdInChIKey = LVTJOONKWUXEFR-UEZXSUPNSA-N |
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'''Protodioscin''' is a ]al ] compound found in a number of plant species, most notably in the '']'', '']'' '']'' and '' ]'' families.<ref>{{cite journal | vauthors = Ganzera M, Bedir E, Khan IA | title = Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection | journal = Journal of Pharmaceutical Sciences | volume = 90 | issue = 11 | pages = 1752–8 | date = November 2001 | pmid = 11745732 | doi = 10.1002/jps.1124 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Hibasami H, Moteki H, Ishikawa K, Katsuzaki H, Imai K, Yoshioka K, Ishii Y, Komiya T | display-authors = 6 | title = Protodioscin isolated from fenugreek (Trigonella foenumgraecum L.) induces cell death and morphological change indicative of apoptosis in leukemic cell line H-60, but not in gastric cancer cell line KATO III | journal = International Journal of Molecular Medicine | volume = 11 | issue = 1 | pages = 23–6 | date = January 2003 | pmid = 12469212 | doi = 10.3892/ijmm.11.1.23 }}</ref><ref>{{cite journal | vauthors = Dong M, Feng XZ, Wang BX, Ikejima T, Wu LJ | title = Steroidal saponins from Dioscorea panthaica and their cytotoxic activity | journal = Die Pharmazie | volume = 59 | issue = 4 | pages = 294–6 | date = April 2004 | pmid = 15125576 }}</ref> It is best known as the putative active component of the herbal ] plant '']''.<ref>{{cite journal | vauthors = Dinchev D, Janda B, Evstatieva L, Oleszek W, Aslani MR, Kostova I | title = Distribution of steroidal saponins in Tribulus terrestris from different geographical regions | journal = Phytochemistry | volume = 69 | issue = 1 | pages = 176–86 | date = January 2008 | pmid = 17719068 | doi = 10.1016/j.phytochem.2007.07.003 | bibcode = 2008PChem..69..176D }}</ref><ref>{{cite journal | vauthors = Singh PP, Patil SS, Bora PS, Bhatt V, Sharma U | title = Govanoside B, a new steroidal saponin from rhizomes of Trillium govanianum | journal = Natural Product Research | date = May 2020 | issue = 6 | pages =1–9 }}</ref> |
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Extracts from ''T. terrestris'' standardised for protodioscin content have been demonstrated to produce proerectile effects in isolated tissues and aphrodisiac action in several animal species.<ref>{{cite journal | vauthors = Gauthaman K, Adaikan PG, Prasad RN | title = Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats | journal = Life Sciences | volume = 71 | issue = 12 | pages = 1385–96 | date = August 2002 | pmid = 12127159 | doi = 10.1016/S0024-3205(02)01858-1 }}</ref><ref>{{cite journal | vauthors = Gauthaman K, Ganesan AP, Prasad RN | title = Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model | journal = Journal of Alternative and Complementary Medicine | volume = 9 | issue = 2 | pages = 257–65 | date = April 2003 | pmid = 12804079 | doi = 10.1089/10755530360623374 }}</ref> It is thought protodioscin achieves this primarily through causing an increase in androgen receptor immunoreactivity, meaning it increases the concentration of androgen receptors in cells, causing the organism to become more sensitive to androgens like testosterone and ] (DHT).<ref>{{cite journal | vauthors = Gauthaman K, Adaikan PG | title = Effect of Tribulus terrestris on nicotinamide adenine dinucleotide phosphate-diaphorase activity and androgen receptors in rat brain | journal = Journal of Ethnopharmacology | volume = 96 | issue = 1–2 | pages = 127–32 | date = January 2005 | pmid = 15588660 | doi = 10.1016/j.jep.2004.08.030 }}</ref> The mechanism for these effects has not been clearly established, and while protodioscin has been demonstrated to trigger release of ] in ] tissue,<ref>{{cite journal | vauthors = Adaikan PG, Gauthaman K, Prasad RN, Ng SC | title = Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum | journal = Annals of the Academy of Medicine, Singapore | volume = 29 | issue = 1 | pages = 22–6 | date = January 2000 | pmid = 10748960 }}</ref> and also to produce statistically significant increases in the levels of the hormones ], ] and ] in animal studies,<ref>{{cite journal | vauthors = Gauthaman K, Ganesan AP | title = The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat | journal = Phytomedicine | volume = 15 | issue = 1–2 | pages = 44–54 | date = January 2008 | pmid = 18068966 | doi = 10.1016/j.phymed.2007.11.011 }}</ref> studies in humans have failed to show ] and its use remains controversial.<ref>{{cite journal | vauthors = Rowland D, Tai W | title = A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions | journal = Journal of Sex & Marital Therapy | volume = 29 | issue = 3 | pages = 185–205 | year = 2003 | pmid = 12851124 | doi = 10.1080/00926230390155096 | s2cid = 45475327 }}</ref><ref>{{cite journal | vauthors = McKay D | title = Nutrients and botanicals for erectile dysfunction: examining the evidence | journal = Alternative Medicine Review | volume = 9 | issue = 1 | pages = 4–16 | date = March 2004 | pmid = 15005641 }}</ref> |
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'''Protodioscin''' is a ] ] compound found in a number of plant species, most notably in the '']'', '']'' and '']'' families.<ref>{{cite journal | doi = 10.1002/jps.1124 | author = Ganzera M, Bedir E, Khan IA | title = Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection | journal = Journal of Pharmaceutical Sciences | year = 2001 | volume = 90 | issue = 11 | pages = 1752–1758 | pmid = 11745732}}</ref><ref>{{cite journal | last1 = Hibasami | first1 = H | last2 = Moteki | first2 = H | last3 = Ishikawa | first3 = K | last4 = Katsuzaki | first4 = H | last5 = Imai | first5 = K | last6 = Yoshioka | first6 = K | last7 = Ishii | first7 = Y | last8 = Komiya | first8 = T | title = Protodioscin isolated from fenugreek (Trigonella foenumgraecum L.) induces cell death and morphological change indicative of apoptosis in leukemic cell line H-60, but not in gastric cancer cell line KATO III. | journal = International journal of molecular medicine | volume = 11 | issue = 1 | pages = 23–6 | year = 2003 | pmid = 12469212}}</ref><ref>{{cite journal | last1 = Dong | first1 = M | last2 = Feng | first2 = XZ | last3 = Wang | first3 = BX | last4 = Ikejima | first4 = T | last5 = Wu | first5 = LJ | title = Steroidal saponins from Dioscorea panthaica and their cytotoxic activity. | journal = Die Pharmazie | volume = 59 | issue = 4 | pages = 294–6 | year = 2004 | pmid = 15125576}}</ref> It is best known as the putative active component of the herbal ] plant '']''.<ref>{{cite journal | last1 = Dinchev | first1 = D | last2 = Janda | first2 = B | last3 = Evstatieva | first3 = L | last4 = Oleszek | first4 = W | last5 = Aslani | first5 = MR | last6 = Kostova | first6 = I | title = Distribution of steroidal saponins in Tribulus terrestris from different geographical regions. | journal = Phytochemistry | volume = 69 | issue = 1 | pages = 176–86 | year = 2008 | pmid = 17719068 | doi = 10.1016/j.phytochem.2007.07.003}}</ref> |
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== References == |
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Extracts from ''T. terrestris'' standardised for protodioscin content have been demonstrated to produce proerectile effects in isolated tissues and aphrodisiac action in several animal species.<ref>{{cite journal | last1 = Gauthaman | first1 = K | last2 = Adaikan | first2 = PG | last3 = Prasad | first3 = RN | title = Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats. | journal = Life sciences | volume = 71 | issue = 12 | pages = 1385–96 | year = 2002 | pmid = 12127159 | doi=10.1016/S0024-3205(02)01858-1}}</ref><ref>{{cite journal | last1 = Gauthaman | first1 = K | last2 = Ganesan | first2 = AP | last3 = Prasad | first3 = RN | title = Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model. | journal = Journal of alternative and complementary medicine (New York, N.Y.) | volume = 9 | issue = 2 | pages = 257–65 | year = 2003 | pmid = 12804079 | doi = 10.1089/10755530360623374}}</ref> The mechanism for these effects has not been clearly established, and while protodioscin has been demonstrated to trigger release of ] in ] tissue,<ref>{{cite journal | last1 = Adaikan | first1 = PG | last2 = Gauthaman | first2 = K | last3 = Prasad | first3 = RN | last4 = Ng | first4 = SC | title = Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum. | journal = Annals of the Academy of Medicine, Singapore | volume = 29 | issue = 1 | pages = 22–6 | year = 2000 | pmid = 10748960}}</ref> and also to produce statistically significant increases in the levels of the hormones ], ] and ] in animal studies,<ref>{{cite journal | last1 = Gauthaman | first1 = K | last2 = Ganesan | first2 = AP | title = The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat. | journal = Phytomedicine : international journal of phytotherapy and phytopharmacology | volume = 15 | issue = 1-2 | pages = 44–54 | year = 2008 | pmid = 18068966 | doi = 10.1016/j.phymed.2007.11.011}}</ref> evidence for efficacy in humans is limited and remains controversial.<ref>{{cite journal | last1 = Rowland | first1 = DL | last2 = Tai | first2 = W | title = A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions. | journal = Journal of sex & marital therapy | volume = 29 | issue = 3 | pages = 185–205 | year = 2003 | pmid = 12851124 | doi = 10.1080/00926230390155096}}</ref><ref>{{cite journal | last1 = McKay | first1 = D | title = Nutrients and botanicals for erectile dysfunction: examining the evidence. | journal = Alternative medicine review : a journal of clinical therapeutic | volume = 9 | issue = 1 | pages = 4–16 | year = 2004 | pmid = 15005641}}</ref> |
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==References== |
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