植物蛻皮類固醇

植物蛻皮類固醇（英語：Phytoecdysteroid）是指由植物合成的一類甾體化合物，後來也在一些動物體內發現。其與節肢動物的蛻皮激素結構上類似，用作毒素或拒食劑來對抗植食性昆蟲^[1]，目前已發現超二百種，推測自然界有超過一千種^[2]。

例子

C27

化合物	分子式	結構	對蛻皮酮的化學修飾	CAS號	常見於^[3]	發現年代^[1]
20-羥基蛻皮酮	C₂₇H₄₄O₇		20β-羥基	5289-74-7	白花蠅子草^[4]、黃雪輪^[5]	1966
坡那甾酮A	C₂₇H₄₄O₆		20β-羥基 -25-去氧	13408-56-5	東北紅豆杉、蕨類植物、耳狀網褶菌、側身地蟹、藍蟹、普通濱蟹、羅漢松^[6]	1966
坡那甾酮B	C₂₇H₄₄O₆	[[File:\|200px]]	20β-羥基 -25-去氧 (2α,3α)	19338-77-3	台灣羅漢松	1966
坡那甾酮C（維基數據所列：Q105216104）	C₂₇H₄₄O₈	[[File:\|200px]]	5β,20β,24S-三羥基 -25-去氧	PubChem CID：15249992	台灣羅漢松、黃銀陸均松	1966
牛膝甾酮（維基數據所列：Q27103165）	C₂₇H₄₄O₇		20β,26-二羥基 -25-去氧	混合：15130-85-5 25R：19682-38-3 25S：19595-18-7	桑屬、日本牛膝（弗氏牛膝）、歐亞多足蕨、藍蟹	1967
羅漢松甾酮B（維基數據所列：Q27103838）	C₂₇H₄₂O₆	[[File:\|200px]]	7-氫-9,15-脫氫-14-去羥基（8(9),14(15)共軛雙鍵）	22612-27-7	羅漢松屬	1968^[7]
羅漢松甾酮C（維基數據所列：Q27109250）	C₂₇H₄₄O₈		20β,26-二羥基	混合：19458-46-9 25R：？ 25S：？		1968^[7]
筋骨草甾酮C	C₂₇H₄₄O₇		11α,20β-二羥基 -25-去氧	23044-80-6	千日紅^[8] 紫背金盤^[9] 蛛絲毛藍耳草^[10]	1969
土克甾酮	C₂₇H₄₄O₈		11α,20β-二羥基	41451-87-0	新疆筋骨草（英語：Ajuga turkestanica）^[11] 普通小麥^[12]	1975
水龍骨甾酮B	C₂₇H₄₄O₈		5β,20β-二羥基	18069-14-2	軸藜^[13] 四葉重樓^[14] 歐亞多足蕨^[15]	1967
米樂甾酮A	C₂₇H₄₄O₈		5β,11α,20β-三羥基 -25-去氧	38778-30-2	千日紅^[8] 短穗假千日紅（宿霧語：Gomphrena serrata）^[8] 月光花屬^[16]	1972^[17]

C28

化合物	分子式	結構	對蛻皮酮的化學修飾	CAS號	發現年代
馬克甾酮A（維基數據所列：Q27149824）	C₂₈H₄₆O₇		20β-羥基 -24R-甲基	20137-14-8	1968
24-表馬克甾酮A	C₂₈H₄₆O₇	[[File:\|200px]]	20β-羥基 -24S-甲基	PubChem SID：274426079	1985
馬克甾酮B（維基數據所列：Q27103229）	C₂₈H₄₆O₇		20β,26-二羥基 -25-去氧 -24R-甲基	20512-31-6	1968

C29

化合物	分子式	結構	對蛻皮酮的化學修飾	CAS號	常見於	發現年代
伏石蕨甾酮（維基數據所列：Q104401829）也稱為：馬克甾酮C、羅漢松甾酮A	C₂₉H₄₈O₇		20β-羥基 -24R-乙基	RS混合：PubChem CID 24984905 19974-41-5		1968^[7]
馬克甾酮D	C₂₉H₄₈O₇	[[File:\|200px]]	20β-羥基 -25-去氧 -24R-羥乙基	20137-11-5		1968

參考文獻

^ ^1.0 ^1.1 Dinan L. Phytoecdysteroids: biological aspects. Phytochemistry. 2001, 57 (3): 325–339. PMID 11393511. doi:10.1016/S0031-9422(01)00078-4.
^ Dinan L, Savchenko T, Whiting P. On the distribution of phytoecdysteroids in plants. Cellular and Molecular Life Sciences. 2001, 58 (8): 1121–1132. PMID 11529504. doi:10.1007/PL00000926.
^ ECDTBASE—THE ECDYSONE HANDBOOK.
^ Abubakirov, N. K. Ecdysteroids of flowering plants (Angiospermae). Chemistry of Natural Compounds. 1981-11, 17 (6): 489–503. doi:10.1007/BF00574363.
^ Báthori, M; Girault, JP; Kalász, H; Máthé, I; Lafont, R. New minor ecdysteroids from Silene otites (L.) Wib.. Journal of pharmaceutical and biomedical analysis. 1997-10, 16 (2): 327–36. PMID 9408851. doi:10.1016/s0731-7085(97)00051-4.
^ 呂岱竹,袁宏球,尹桂豪,高麗花. 高效液相色谱法测定坡那甾酮-A. 熱帶作物學報. 2006, 27 (3): 97-99.
^ ^7.0 ^7.1 ^7.2 Galbraith, M. N.; Horn, D. H. S.; Porter, Q. N.; Hackney, R. J. Structure of podecdysone A, a steroid with moulting hormone activity from the bark of Podocarpus elatus R.Br.. Chemical Communications (London). 1968, (16): 971. doi:10.1039/C19680000971.
^ ^8.0 ^8.1 ^8.2 Tamara Savchenko; Pensri Whiting; Satyajit D Sarker. Distribution and identity of phytoecdysteroids in Gomphrena spp. (Amaranthaceae). Biochemical Systematics and Ecology. 2002-07, 26 (3). doi:10.1016/S0305-1978(97)00106-3.
^ Zeng, XN; Coll, J; Camps, F; Palacin, MJ. Analysis of phytoecdysteroids in cultured plants of Ajuga nipponensis makino.. Journal of Asian natural products research. 2000, 2 (4): 263–9. PMID 11249608. doi:10.1080/10286020008041365.
^ Tan, CY; Wang, JH; Zhang, H; Li, X. A new phytosterone from Cyanotis arachnoidea.. Journal of Asian natural products research. 2002-03, 4 (1): 7–10. PMID 11991195. doi:10.1080/10286020290019631.
^ Guibout L, Mamadalieva N, Balducci C, Girault JP, Lafont R. The minor ecdysteroids from Ajuga turkestanica (PDF). Phytochemical Analysis. 2015, 26 (5): 293–300 [2022-08-06]. PMID 25953625. doi:10.1002/pca.2563. （原始內容存檔 (PDF)於2022-01-07）.
^ Janeczko A, Oklestkova J, Tarkowská D, Drygaś B. Naturally Occurring Ecdysteroids in Triticum aestivum L. and Evaluation of Fenarimol as a Potential Inhibitor of Their Biosynthesis in Plants. International Journal of Molecular Sciences. March 2021, 22 (6): 2855. PMC 7999220  . PMID 33799719. doi:10.3390/ijms22062855  .
^ S D Sarker; V Sik; H H Rees; L Dinan. 1 alpha,20R-dihydroxyecdysone from Axyris amaranthoides. Phytochemistry. 1998-12, 49 (8). doi:10.1016/S0031-9422(98)00446-4.
^ N. K. Abubakirov. Ecdysteroids of flowering plants (Angiospermae). Chemistry of Natural Compounds. 2004-11, 17 (6). doi:10.1007/BF00574363.
^ Maria-Pilar Marco; Francisco J. Sánchez-Baeza; Francisco Camps; José Coll. Phytoecdysteroid analysis by high-performance liquid chromatography-thermospray mass spectrometry. Journal of Chromatography A. 1993-07, 641 (1). doi:10.1016/0021-9673(93)83461-Z （英語）.
^ Luigi Canonica, Bruno Danieli, Giorgio Ferrari, Jiri Krepinsky, Irene Weisz-Vincze. A novel method of isolation of phytoecdysones from kaladana seeds. Phytochemistry. 1975, 14 (2): 525-527. doi:10.1016/0031-9422(75)85122-3.
^ L. Canonica, B. Danieli, I. Weisz-Vincze, G. Ferrari. Structure of muristerone A, a new phytoecdysone. Journal of the Chemical Society, Chemical Communications. 1972, (19): 1060b-1061. doi:10.1039/C3972001060B.

外部連結

Ecdybase (The Ecdysone Handbook) - a free online ecdysteroids database. ecdybase.org.

[Dinan_L2001-1] 1.0 ^1.1 Dinan L. Phytoecdysteroids: biological aspects. Phytochemistry. 2001, 57 (3): 325–339. PMID 11393511. doi:10.1016/S0031-9422(01)00078-4.

[2] Dinan L, Savchenko T, Whiting P. On the distribution of phytoecdysteroids in plants. Cellular and Molecular Life Sciences. 2001, 58 (8): 1121–1132. PMID 11529504. doi:10.1007/PL00000926.

[3] ECDTBASE—THE ECDYSONE HANDBOOK.

[4] Abubakirov, N. K. Ecdysteroids of flowering plants (Angiospermae). Chemistry of Natural Compounds. 1981-11, 17 (6): 489–503. doi:10.1007/BF00574363.

[5] Báthori, M; Girault, JP; Kalász, H; Máthé, I; Lafont, R. New minor ecdysteroids from Silene otites (L.) Wib.. Journal of pharmaceutical and biomedical analysis. 1997-10, 16 (2): 327–36. PMID 9408851. doi:10.1016/s0731-7085(97)00051-4.

[6] 呂岱竹,袁宏球,尹桂豪,高麗花. 高效液相色谱法测定坡那甾酮-A. 熱帶作物學報. 2006, 27 (3): 97-99.

[罗汉松-7] 7.0 ^7.1 ^7.2 Galbraith, M. N.; Horn, D. H. S.; Porter, Q. N.; Hackney, R. J. Structure of podecdysone A, a steroid with moulting hormone activity from the bark of Podocarpus elatus R.Br.. Chemical Communications (London). 1968, (16): 971. doi:10.1039/C19680000971.

[千日紅-8] 8.0 ^8.1 ^8.2 Tamara Savchenko; Pensri Whiting; Satyajit D Sarker. Distribution and identity of phytoecdysteroids in Gomphrena spp. (Amaranthaceae). Biochemical Systematics and Ecology. 2002-07, 26 (3). doi:10.1016/S0305-1978(97)00106-3.

[9] Zeng, XN; Coll, J; Camps, F; Palacin, MJ. Analysis of phytoecdysteroids in cultured plants of Ajuga nipponensis makino.. Journal of Asian natural products research. 2000, 2 (4): 263–9. PMID 11249608. doi:10.1080/10286020008041365.

[10] Tan, CY; Wang, JH; Zhang, H; Li, X. A new phytosterone from Cyanotis arachnoidea.. Journal of Asian natural products research. 2002-03, 4 (1): 7–10. PMID 11991195. doi:10.1080/10286020290019631.

[11] Guibout L, Mamadalieva N, Balducci C, Girault JP, Lafont R. The minor ecdysteroids from Ajuga turkestanica (PDF). Phytochemical Analysis. 2015, 26 (5): 293–300 [2022-08-06]. PMID 25953625. doi:10.1002/pca.2563. （原始內容存檔 (PDF)於2022-01-07）.

[12] Janeczko A, Oklestkova J, Tarkowská D, Drygaś B. Naturally Occurring Ecdysteroids in Triticum aestivum L. and Evaluation of Fenarimol as a Potential Inhibitor of Their Biosynthesis in Plants. International Journal of Molecular Sciences. March 2021, 22 (6): 2855. PMC 7999220  . PMID 33799719. doi:10.3390/ijms22062855  .

[13] S D Sarker; V Sik; H H Rees; L Dinan. 1 alpha,20R-dihydroxyecdysone from Axyris amaranthoides. Phytochemistry. 1998-12, 49 (8). doi:10.1016/S0031-9422(98)00446-4.

[14] N. K. Abubakirov. Ecdysteroids of flowering plants (Angiospermae). Chemistry of Natural Compounds. 2004-11, 17 (6). doi:10.1007/BF00574363.

[15] Maria-Pilar Marco; Francisco J. Sánchez-Baeza; Francisco Camps; José Coll. Phytoecdysteroid analysis by high-performance liquid chromatography-thermospray mass spectrometry. Journal of Chromatography A. 1993-07, 641 (1). doi:10.1016/0021-9673(93)83461-Z （英語）.

[16] Luigi Canonica, Bruno Danieli, Giorgio Ferrari, Jiri Krepinsky, Irene Weisz-Vincze. A novel method of isolation of phytoecdysones from kaladana seeds. Phytochemistry. 1975, 14 (2): 525-527. doi:10.1016/0031-9422(75)85122-3.

[17] L. Canonica, B. Danieli, I. Weisz-Vincze, G. Ferrari. Structure of muristerone A, a new phytoecdysone. Journal of the Chemical Society, Chemical Communications. 1972, (19): 1060b-1061. doi:10.1039/C3972001060B.

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