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原薯蕷皂苷

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原薯蕷皂苷
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  • 26-O-beta-D-Glycopyranosyl-22-hydroxyfurost-5-ene-3beta,26-diol-3-O-beta-diglucorhamnoside
CAS號55056-80-9
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ChemSpider
UNII
化學資訊
化學式C51H84O22
摩爾質量1,049.21 g·mol−1
3D模型(JSmol英語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

原薯蕷皂苷(英語:Protodioscin)簡稱原薯蕷苷,是一種甾體皂苷(具體為呋喃固醇皂苷)[1][2]。其存在於多種植物中,尤屬蒺藜屬胡盧巴屬薯蕷屬以及延齡草屬最甚[3][4][5]。它被認為是知名壯陽植物蒺藜(學名:Tribulus terrestris)的主要活性成分[6][7]。同時也是穿龍薯蕷(中藥名:穿山龍,學名:Dioscorea nipponica)中的主要活性成分[1][8]

不同產地的蒺藜中含有的原薯蕷皂苷含量不同。中國產的蒺藜果實不含或很少含有原薯蕷皂苷;越南、印度以及保加利亞等歐洲國家所產蒺藜含有原薯蕷皂苷,而且後者原薯蕷皂苷含量遠超出前兩地產的蒺藜的數十至數百倍。不過蒺藜經過炒制後,原薯蕷皂苷會先經脫水生成偽原薯蕷皂苷(pseudoprotodiosin),隨後發生脫糖反應分解成次級皂苷[9]

研究證實蒺藜標準原薯蕷皂苷提取物對離體組織有助勃起作用,以及對幾種動物具有催情作用[10][11]。研究者認為原薯蕷皂苷是通過促使雄激素受體的免疫反應來實現這一效果,使得細胞中雄激素受體濃度增加,造成動物對諸如睾酮二氫睾酮等雄激素更加敏感[12],但是其具體機制尚未明確。目前已證實原薯蕷皂苷能引發陰莖海綿體組織釋放一氧化氮[13]。在動物身上發現能顯著提高睾酮、二氫睾酮和脫氫表雄酮激素水平[14],但在人體研究上未能展示出其有效性,而且其用途仍存在爭議[15][16]

參考文獻

  1. ^ 1.0 1.1 韓君,林帥. 核磁共振定量技术测定原薯蓣皂苷对照品的含量. 化學工程師. 2021, (6): 21-23. doi:10.16247/j.cnki.23-1171/tq.20210621. 
  2. ^ 蘇子仁 、賴小平 (編). 汉英、英汉中草药化学成分词汇. 北京: 中國中醫藥出版社. 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可免費查閱. 
  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. ^ 張杰,胡天宇,沈國亮,楊陽,顧正兵. 穿山龙中原薯蓣皂苷杂质的分离与鉴定. 中成藥. 2015, 37 (12): 2682-2686. doi:10.3969/j.issn.1001-1528.2015.12.024. 
  9. ^ 劉坤琳,王麗麗,王帥. 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. 中藥材. 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.