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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> '''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>


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> 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 | 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>


==References== ==References==

Revision as of 21:13, 5 October 2011

Pharmaceutical compound
Protodioscin
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
IUPAC name
  • 26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC51H84O22
Molar mass1049.199 g/mol g·mol
3D model (JSmol)
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
InChI
  • InChI=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
  • Key:LVTJOONKWUXEFR-UEZXSUPNSA-N
  (verify)

Protodioscin is a steroidal saponin compound found in a number of plant species, most notably in the Tribulus, Trigonella and Dioscorea families. It is best known as the putative active component of the herbal aphrodisiac plant Tribulus terrestris.

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. The mechanism for these effects has not been clearly established, and while protodioscin has been demonstrated to trigger release of nitric oxide in corpus cavernosum tissue, and also to produce statistically significant increases in the levels of the hormones testosterone, dihydrotestosterone and dehydroepiandrosterone in animal studies, evidence for efficacy in humans is limited and remains controversial.

References

  1. Ganzera M, Bedir E, Khan IA (2001). "Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection". Journal of Pharmaceutical Sciences. 90 (11): 1752–1758. doi:10.1002/jps.1124. PMID 11745732.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Hibasami, H; Moteki, H; Ishikawa, K; Katsuzaki, H; Imai, K; Yoshioka, K; Ishii, Y; Komiya, T (2003). "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". International journal of molecular medicine. 11 (1): 23–6. PMID 12469212.
  3. Dong, M; Feng, XZ; Wang, BX; Ikejima, T; Wu, LJ (2004). "Steroidal saponins from Dioscorea panthaica and their cytotoxic activity". Die Pharmazie. 59 (4): 294–6. PMID 15125576.
  4. Dinchev, D; Janda, B; Evstatieva, L; Oleszek, W; Aslani, MR; Kostova, I (2008). "Distribution of steroidal saponins in Tribulus terrestris from different geographical regions". Phytochemistry. 69 (1): 176–86. doi:10.1016/j.phytochem.2007.07.003. PMID 17719068.
  5. Gauthaman, K; Adaikan, PG; Prasad, RN (2002). "Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats". Life sciences. 71 (12): 1385–96. doi:10.1016/S0024-3205(02)01858-1. PMID 12127159.
  6. Gauthaman, K; Ganesan, AP; Prasad, RN (2003). "Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model". Journal of alternative and complementary medicine. 9 (2): 257–65. doi:10.1089/10755530360623374. PMID 12804079.
  7. Adaikan, PG; Gauthaman, K; Prasad, RN; Ng, SC (2000). "Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum". Annals of the Academy of Medicine, Singapore. 29 (1): 22–6. PMID 10748960.
  8. Gauthaman, K; Ganesan, AP (2008). "The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat". Phytomedicine : international journal of phytotherapy and phytopharmacology. 15 (1–2): 44–54. doi:10.1016/j.phymed.2007.11.011. PMID 18068966.
  9. Rowland, DL; Tai, W (2003). "A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions". Journal of sex & marital therapy. 29 (3): 185–205. doi:10.1080/00926230390155096. PMID 12851124.
  10. McKay, D (2004). "Nutrients and botanicals for erectile dysfunction: examining the evidence". Alternative medicine review : a journal of clinical therapeutic. 9 (1): 4–16. PMID 15005641.
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