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原薯蓣皂苷

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原薯蓣皂苷
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识别信息
  • 26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside
CAS号55056-80-9
PubChem CID
ChemSpider
UNII
化学信息
化学式C51H84O22
摩尔质量1,049.21 g·mol−1
3D模型(JSmol英语JSmol
  • 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=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 checkY
  • Key:LVTJOONKWUXEFR-UEZXSUPNSA-N checkY

原薯蓣皂苷(英語:Protodioscin)简称原薯蓣苷,是一种甾体皂苷(具体为呋喃固醇皂苷)[1][2]。其存在于多种植物中,尤属蒺藜属胡卢巴属薯蓣属以及延龄草属最甚[3][4][5]。它被认为是知名壮阳植物蒺藜(学名:Tribulus terrestris)的主要活性成分[6][7]。同时也是穿龙薯蓣(中药名:穿山龙,学名:Dioscorea nipponica)中的主要活性成分[1][8]

不同产地的蒺藜中含有的原薯蓣皂苷含量不同。中国产的蒺藜果实不含或很少含有原薯蓣皂苷;越南、印度以及保加利亚等欧洲国家所产蒺藜含有原薯蓣皂苷,而且后者原薯蓣皂苷含量远超出前两地产的蒺藜的数十至数百倍。不过蒺藜经过炒制后,原薯蓣皂苷会先经脱水生成伪原薯蓣皂苷(pseudoprotodiosin),随后发生脱糖反应分解成次级皂苷[9]

研究证实蒺藜标准原薯蓣皂苷提取物对离体组织有助勃起作用,以及对几种动物具有催情作用[10][11]。研究者认为原薯蓣皂苷是通过促使雄激素受体的免疫反应来实现这一效果,使得细胞中雄激素受体浓度增加,造成动物对诸如睾酮二氢睾酮等雄激素更加敏感[12],但是其具体机制尚未明确。目前已证实原薯蓣皂苷能引发阴茎海绵体组织释放一氧化氮[13]。在动物身上发现能显著提高睾酮、二氢睾酮和脱氢表雄酮激素水平[14],但在人体研究上未能展示出其有效性,而且其用途仍存在争议[15][16]

参考文献

  1. ^ 1.0 1.1 韩君,林帅. 核磁共振定量技术测定原薯蓣皂苷对照品的含量. 化学工程师. 2021, (6): 21-23. doi:10.16247/j.cnki.23-1171/tq.20210621. 
  2. ^ 苏子仁 、赖小平 (编). 汉英、英汉中草药化学成分词汇. 北京: 中国中医药出版社. 2006: 679. ISBN 9787801569103. 
  3. ^ Ganzera M, Bedir E, Khan IA. Determination of steroidal saponins in Tribulus terrestris by reversed-phase high-performance liquid chromatography and evaporative light scattering detection. Journal of Pharmaceutical Sciences. November 2001, 90 (11): 1752–8. PMID 11745732. doi:10.1002/jps.1124可免费查阅. 
  4. ^ Hibasami H, Moteki H, Ishikawa K, Katsuzaki H, Imai K, Yoshioka K, et al. 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. January 2003, 11 (1): 23–6. PMID 12469212. doi:10.3892/ijmm.11.1.23. 
  5. ^ Dong M, Feng XZ, Wang BX, Ikejima T, Wu LJ. Steroidal saponins from Dioscorea panthaica and their cytotoxic activity. Die Pharmazie. April 2004, 59 (4): 294–6. PMID 15125576. 
  6. ^ Dinchev D, Janda B, Evstatieva L, Oleszek W, Aslani MR, Kostova I. Distribution of steroidal saponins in Tribulus terrestris from different geographical regions. Phytochemistry. January 2008, 69 (1): 176–86. Bibcode:2008PChem..69..176D. PMID 17719068. doi:10.1016/j.phytochem.2007.07.003. 
  7. ^ Singh PP, Patil SS, Bora PS, Bhatt V, Sharma U. Govanoside B, a new steroidal saponin from rhizomes of Trillium govanianum. Natural Product Research. May 2020, (6): 1–9. 
  8. ^ 张杰,胡天宇,沈国亮,杨阳,顾正兵. 穿山龙中原薯蓣皂苷杂质的分离与鉴定. 中成药. 2015, 37 (12): 2682-2686. doi:10.3969/j.issn.1001-1528.2015.12.024. 
  9. ^ 刘坤琳,王丽丽,王帅. 不同炒制温度和时间对蒺藜中4个薯蓣皂苷类成分的影响. 中药材. 2022, 45 (1): 62-72. doi:10.13863/j.issn1001-4454.2022.01.012. 
  10. ^ Gauthaman K, Adaikan PG, Prasad RN. Aphrodisiac properties of Tribulus Terrestris extract (Protodioscin) in normal and castrated rats. Life Sciences. August 2002, 71 (12): 1385–96. PMID 12127159. doi:10.1016/S0024-3205(02)01858-1. 
  11. ^ Gauthaman K, Ganesan AP, Prasad RN. Sexual effects of puncturevine (Tribulus terrestris) extract (protodioscin): an evaluation using a rat model. Journal of Alternative and Complementary Medicine. April 2003, 9 (2): 257–65. PMID 12804079. doi:10.1089/10755530360623374. 
  12. ^ Gauthaman K, Adaikan PG. Effect of Tribulus terrestris on nicotinamide adenine dinucleotide phosphate-diaphorase activity and androgen receptors in rat brain. Journal of Ethnopharmacology. January 2005, 96 (1–2): 127–32. PMID 15588660. doi:10.1016/j.jep.2004.08.030. 
  13. ^ Adaikan PG, Gauthaman K, Prasad RN, Ng SC. Proerectile pharmacological effects of Tribulus terrestris extract on the rabbit corpus cavernosum. Annals of the Academy of Medicine, Singapore. January 2000, 29 (1): 22–6. PMID 10748960. 
  14. ^ Gauthaman K, Ganesan AP. The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat. Phytomedicine. January 2008, 15 (1–2): 44–54. PMID 18068966. doi:10.1016/j.phymed.2007.11.011. 
  15. ^ Rowland D, Tai W. A review of plant-derived and herbal approaches to the treatment of sexual dysfunctions. Journal of Sex & Marital Therapy. 2003, 29 (3): 185–205. PMID 12851124. S2CID 45475327. doi:10.1080/00926230390155096. 
  16. ^ McKay D. Nutrients and botanicals for erectile dysfunction: examining the evidence. Alternative Medicine Review. March 2004, 9 (1): 4–16. PMID 15005641.