脫水莫諾苷元

脫水莫諾苷元
	IUPAC名; Methyl (1S,3S,7R,8R,9R)-9-methyl-2,4,10-trioxatricyclo[5.3.1.03,8]undec-5-ene-6-carboxylate
識別
CAS號	59653-37-1
PubChem	427877
ChemSpider	10226990
SMILES	CC1C2C3CC(O1)OC2OC=C3C(=O)OC;
性質
化學式	C11H14O5
摩爾質量	226.23 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

脫水莫諾苷元（英語：Sarracenin），也叫瓶子草素，是一種環烯醚萜化合物，存在於瓶子草科的多種植物中，這種植物是肉食性的。^[1]它也可在其它非肉食植物中找到，例如Strychnos spinosa（馬錢科）^[2]和墓頭回（忍冬科）。^[3]

歷史

脫水莫諾苷元於1976年首次從黃瓶子草根中分離出。奧克弗諾基沼澤地區的人們將黃瓶子草提取物用作民間療法，促使人們對黃瓶子草提取物進行分析。^[4]

生物合成

據信，脫水莫諾苷元源自馬錢子苷，而莫諾苷或斷馬錢子苷則在生物合成過程中起着中間體的作用。^[4]

用途

脫水莫諾苷元對多種病原體表現出抗菌活性，包括金黃色葡萄球菌、化膿性鏈球菌、痢疾志賀氏菌、肺炎克雷伯氏菌、白色念珠菌、熱帶念珠菌、Candida thrusei和星狀念珠菌。^[2]它還證明了對三種腫瘤細胞系的細胞毒性：A-375（人黑色素瘤細胞）、SGC-7901（維基數據所列：Q54953170）（人胃癌細胞）和HeLa。^[3]

生態

脫水莫諾苷元是太陽瓶子草屬物種吸引昆蟲的勺子中存在的主要揮發物。在實驗室環境中培養的太陽瓶子草屬植物中，很少發現有脫水莫諾苷元存在。產生脫水莫諾苷元的植物通常比沒有產生的吸引更多的昆蟲，這表明它在吸引或捕捉獵物方面發揮着作用。^[5]脫水莫諾苷元也存在於眼鏡蛇瓶子草和許多瓶子草屬物種的瓶蓋中，很可能起着與太陽瓶子植物相同的作用。^[1]

參考資料

^ ^1.0 ^1.1 Hotti H, Gopalacharyulu P, Seppänen-Laakso T, Rischer H. Metabolite profiling of the carnivorous pitcher plants Darlingtonia and Sarracenia. PLOS ONE. 2017-02-21, 12 (2): e0171078. Bibcode:2017PLoSO..1271078H. PMC 5319649 . PMID 28222171. doi:10.1371/journal.pone.0171078 .
^ ^2.0 ^2.1 Tor-Anyiin TA, Igoli JO, Anyam JV, Anyam JN. Isolation and Antimicrobial Activity of Sarracenin From Root Bark of Strychnos Spinosa.. Journal of Chemical Society of Nigeria. 2015, 40 (1). S2CID 55620516.
^ ^3.0 ^3.1 Sheng L, Yang Y, Zhang Y, Li N. Chemical constituents of Patrinia heterophylla Bunge and selective cytotoxicity against six human tumor cells. Journal of Ethnopharmacology. May 2019, 236: 129–135. PMID 30853646. S2CID 73727478. doi:10.1016/j.jep.2019.03.005.
^ ^4.0 ^4.1 Miles DH, Kokpol U, Bhattacharyya J, Atwood JL, Stone KE, Bryson TA, Wilson C. Structure of sarracenin. An unusual enol diacetal monoterpene from the insectivorous plant Sarracenia flava. Journal of the American Chemical Society. March 1976, 98 (6): 1569–1573. doi:10.1021/ja00422a048.
^ Jaffé K, Blum MS, Fales HM, Mason RT, Cabrera A. On insect attractants from pitcher plants of the genusHeliamphora (sarraceniaceae). Journal of Chemical Ecology. March 1995, 21 (3): 379–384. Bibcode:1995JCEco..21..379J. PMID 24234068. S2CID 12537352. doi:10.1007/BF02036725.

[:0-1] 1.0 ^1.1 Hotti H, Gopalacharyulu P, Seppänen-Laakso T, Rischer H. Metabolite profiling of the carnivorous pitcher plants Darlingtonia and Sarracenia. PLOS ONE. 2017-02-21, 12 (2): e0171078. Bibcode:2017PLoSO..1271078H. PMC 5319649 . PMID 28222171. doi:10.1371/journal.pone.0171078 .

[Tor-Anyiin_2015-2] 2.0 ^2.1 Tor-Anyiin TA, Igoli JO, Anyam JV, Anyam JN. Isolation and Antimicrobial Activity of Sarracenin From Root Bark of Strychnos Spinosa.. Journal of Chemical Society of Nigeria. 2015, 40 (1). S2CID 55620516.

[Sheng_2019-3] 3.0 ^3.1 Sheng L, Yang Y, Zhang Y, Li N. Chemical constituents of Patrinia heterophylla Bunge and selective cytotoxicity against six human tumor cells. Journal of Ethnopharmacology. May 2019, 236: 129–135. PMID 30853646. S2CID 73727478. doi:10.1016/j.jep.2019.03.005.

[Miles_1976-4] 4.0 ^4.1 Miles DH, Kokpol U, Bhattacharyya J, Atwood JL, Stone KE, Bryson TA, Wilson C. Structure of sarracenin. An unusual enol diacetal monoterpene from the insectivorous plant Sarracenia flava. Journal of the American Chemical Society. March 1976, 98 (6): 1569–1573. doi:10.1021/ja00422a048.

[5] Jaffé K, Blum MS, Fales HM, Mason RT, Cabrera A. On insect attractants from pitcher plants of the genusHeliamphora (sarraceniaceae). Journal of Chemical Ecology. March 1995, 21 (3): 379–384. Bibcode:1995JCEco..21..379J. PMID 24234068. S2CID 12537352. doi:10.1007/BF02036725.

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