Protodioscin

Protodioscin

Systematic (IUPAC) name
26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside
Clinical data
Routes of administration	Oral
Legal status	Legal
Identifiers
CAS Number	55056-80-9
ATC code	none
PubChem	CID 441891
ChemSpider	390467
Chemical data
Formula	C51H84O22
Molar mass	1049.199 g/mol
SMILES C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)C)C)O[C@@]1(CC[C@@H](C)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](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
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Protodioscin is a steroidal saponin compound found in a number of plant species, most notably in the Tribulus, Trigonella and Dioscorea families.^[1][2][3] It is best known as the putative active component of the herbal aphrodisiac plant Tribulus terrestris.^[4]

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.^[5][6] It is thought protodioscin achieves this primarily through causing an increase in androgen receptor immunoreacivity, meaning it increases the concentration of androgen receptors in cells, causing the organism to become more sensitive to androgens like testosterone and DHT.^[7] 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,^[8] and also to produce statistically significant increases in the levels of the hormones testosterone, dihydrotestosterone and dehydroepiandrosterone in animal studies,^[9] but studies in humans have failed to show efficacy and its use remains controversial.^[10][11]

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.
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. doi:10.3892/ijmm.11.1.23. 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. http://www.ncbi.nlm.nih.gov/pubmed/15588660
8. 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.
9. 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.
10. 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.
11. McKay, D (2004). "Nutrients and botanicals for erectile dysfunction: examining the evidence". Alternative Medicine Review 9 (1): 4–16. PMID 15005641.