脱水莫诺苷元

脱水莫诺苷元
	IUPAC名; Methyl (1S,3S,7R,8R,9R)-9-methyl-2,4,10-trioxatricyclo[5.3.1.03,8]undec-5-ene-6-carboxylate
识别
CAS号	59653-37-1
PubChem	427877
ChemSpider	10226990
SMILES	CC1C2C3CC(O1)OC2OC=C3C(=O)OC;
性质
化学式	C11H14O5
摩尔质量	226.23 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

脱水莫诺苷元（英语：Sarracenin），也叫瓶子草素，是一种环烯醚萜化合物，存在于瓶子草科的多种植物中，这种植物是肉食性的。^[1]它也可在其它非肉食植物中找到，例如Strychnos spinosa（马钱科）^[2]和墓头回（忍冬科）。^[3]

历史

脱水莫诺苷元于1976年首次从黄瓶子草根中分离出。奥克弗诺基沼泽地区的人们将黄瓶子草提取物用作民间疗法，促使人们对黄瓶子草提取物进行分析。^[4]

生物合成

据信，脱水莫诺苷元源自马钱子苷，而莫诺苷或断马钱子苷则在生物合成过程中起着中间体的作用。^[4]

用途

脱水莫诺苷元对多种病原体表现出抗菌活性，包括金黄色葡萄球菌、化脓性链球菌、痢疾志贺氏菌、肺炎克雷伯氏菌、白色念珠菌、热带念珠菌、Candida thrusei和星状念珠菌。^[2]它还证明了对三种肿瘤细胞系的细胞毒性：A-375（人黑色素瘤细胞）、SGC-7901（维基数据所列：Q54953170）（人胃癌细胞）和HeLa。^[3]

生态

脱水莫诺苷元是太阳瓶子草属物种吸引昆虫的勺子中存在的主要挥发物。在实验室环境中培养的太阳瓶子草属植物中，很少发现有脱水莫诺苷元存在。产生脱水莫诺苷元的植物通常比没有产生的吸引更多的昆虫，这表明它在吸引或捕捉猎物方面发挥着作用。^[5]脱水莫诺苷元也存在于眼镜蛇瓶子草和许多瓶子草属物种的瓶盖中，很可能起着与太阳瓶子植物相同的作用。^[1]

参考资料

^ ^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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