石花酸

石花酸
	IUPAC名; 2-Hydroxy-3-(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy-4-methoxy-6-propylbenzoic acid
識別
CAS號	607-11-4
PubChem	12315460
SMILES	CCCC1=CC(=C(C(=C1C(=O)O)O)OC(=O)C2=C(C=C(C=C2O)OC)CCC)OC;
InChI	1S/C22H26O8/c1-5-7-12-9-14(28-3)11-15(23)17(12)22(27)30-20-16(29-4)10-13(8-6-2)18(19(20)24)21(25)26/h9-11,23-24H,5-8H2,1-4H3,(H,25,26);
InChIKey	CPHXGYQLOSNELY-UHFFFAOYSA-N
ChEBI	144301
性質
化學式	C22H26O8
摩爾質量	418.44 g·mol−1
外觀	直角稜柱形或菱片狀晶體
熔點	150-151 °C（272 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

石花酸（英語：Sekikaic acid）^[1]是一種從地衣中提取得到的縮酚酸類化合物。其最初從樹花屬的石樹花（Ramalina sekika）中提取得到，同時其他樹花屬地衣以及石蕊屬地衣均含有石花酸^[2]。此外在癩屑衣屬的Lepraria sekikaica地衣中也發現了石花酸，是除樹花屬和石蕊屬之外的一個罕見特例^[3]。

在這些地衣體內代謝產生石花酸過程中，同時有4'O-去甲石花酸（4'O-demethylsekikaic acid）和高石花酸（homosekikaic acid）等伴生產物生成^[4]。

性質

石花酸純品為無色直角稜柱狀或菱片狀晶體，熔點為150-151°C。其作為一種酚類物質，其乙醇溶液可以與三氯化鐵顯紫色。其紫外吸收光譜有三個最大吸收峰，分別為219、263和303 nm^[5]。

研究證明石花酸具有多種生物活性，包括抗氧化活性^[6]、抑制α-葡萄糖苷酶和α-澱粉酶活性以及降血糖血脂作用^[7]。此外其對人類呼吸道合胞病毒也有顯著抑制作用，且效果優於標準抗病毒藥物利巴韋林^[8]。

參考文獻

^ 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. ISBN 9787801569103.
^ Culberson, Chicita. Supplement to "Chemical and Botanical Guide to Lichen Products". The Bryologist. 1970, 73 (2): 177–377. JSTOR 3241261. doi:10.2307/3241261.
^ Lumbsch, H.T.; Ahti, T.; Altermann, S.; De Paz, G.A.; Aptroot, A.; Arup, U.; et al. One hundred new species of lichenized fungi: a signature of undiscovered global diversity. Phytotaxa. 2011, 18 (1): 81–82. doi:10.11646/phytotaxa.18.1.1 . hdl:11336/4198 .
^ Cordeiro, Lucimara M.C.; Iacomini, Marcello; Stocker-Wörgötter, Elfie. Culture studies and secondary compounds of six Ramalina species. Mycological Research. 2004, 108 (5): 489–497. PMID 15230001. doi:10.1017/s0953756204009402.
^ Huneck, Siegfried. Identification of Lichen Substances. Berlin, Heidelberg: Springer Berlin Heidelberg. 1996: 49; 115; 296–297. ISBN 978-3-642-85245-9. OCLC 851387266.
^ Sisodia, R.; Geol, M.; Verma, S.; Rani, A.; Dureja, P. Antibacterial and antioxidant activity of lichen species Ramalina roesleri. Natural Product Research. 2013, 27 (23): 2235–2239. PMID 23822758. doi:10.1080/14786419.2013.811410.
^ Tatipamula, Vinay Bharadwaj; Annam, Satya Sowbhagya Priya; Nguyen, Ha Thi; Polimati, Haritha; Yejella, Rajendra Prasad. Sekikaic acid modulates pancreatic β-cells in streptozotocin-induced type 2 diabetic rats by inhibiting digestive enzymes. Natural Product Research. 2020, 35 (23): 5420–5424. PMID 32498563. doi:10.1080/14786419.2020.1775226.
^ Lai, Daowan; Odimegwu, Damian; Esimone, Charles; Grunwald, Thomas; Proksch, Peter. Phenolic compounds with in vitro activity against Respiratory Syncytial Virus from the Nigerian lichen Ramalina farinacea. Planta Medica. 2013, 79 (15): 1440–1446. PMID 23970423. doi:10.1055/s-0033-1350711.

[1] 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. ISBN 9787801569103.

[Culberson_1970-2] Culberson, Chicita. Supplement to "Chemical and Botanical Guide to Lichen Products". The Bryologist. 1970, 73 (2): 177–377. JSTOR 3241261. doi:10.2307/3241261.

[Lumbsch_et_al._2011-3] Lumbsch, H.T.; Ahti, T.; Altermann, S.; De Paz, G.A.; Aptroot, A.; Arup, U.; et al. One hundred new species of lichenized fungi: a signature of undiscovered global diversity. Phytotaxa. 2011, 18 (1): 81–82. doi:10.11646/phytotaxa.18.1.1 . hdl:11336/4198 .

[Cordeiro_et_al._2004-4] Cordeiro, Lucimara M.C.; Iacomini, Marcello; Stocker-Wörgötter, Elfie. Culture studies and secondary compounds of six Ramalina species. Mycological Research. 2004, 108 (5): 489–497. PMID 15230001. doi:10.1017/s0953756204009402.

[Huneck_1996-5] Huneck, Siegfried. Identification of Lichen Substances. Berlin, Heidelberg: Springer Berlin Heidelberg. 1996: 49; 115; 296–297. ISBN 978-3-642-85245-9. OCLC 851387266.

[Sisodia_et_al._2013-6] Sisodia, R.; Geol, M.; Verma, S.; Rani, A.; Dureja, P. Antibacterial and antioxidant activity of lichen species Ramalina roesleri. Natural Product Research. 2013, 27 (23): 2235–2239. PMID 23822758. doi:10.1080/14786419.2013.811410.

[Tatipamula_et_al._2020-7] Tatipamula, Vinay Bharadwaj; Annam, Satya Sowbhagya Priya; Nguyen, Ha Thi; Polimati, Haritha; Yejella, Rajendra Prasad. Sekikaic acid modulates pancreatic β-cells in streptozotocin-induced type 2 diabetic rats by inhibiting digestive enzymes. Natural Product Research. 2020, 35 (23): 5420–5424. PMID 32498563. doi:10.1080/14786419.2020.1775226.

[Lai_et_al._2013-8] Lai, Daowan; Odimegwu, Damian; Esimone, Charles; Grunwald, Thomas; Proksch, Peter. Phenolic compounds with in vitro activity against Respiratory Syncytial Virus from the Nigerian lichen Ramalina farinacea. Planta Medica. 2013, 79 (15): 1440–1446. PMID 23970423. doi:10.1055/s-0033-1350711.

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