2019.6.22 更新義大利酮II結構式 ：義大利酮II (2,4,6,9-tetramethyl-8-decene-3,5-dione)
義大利永久花(Immortelle，Helichrysum italicum)
菊科(Asteraceae)蠟菊屬(Helichrysum)
學名：Helichrysum italicum
中文名：義大利永久花、義大利蠟菊
圖1：義大利永久花(Helichrysum italicum ssp. italicum)#1
屬名Helichrysum來自於希臘語的“helios”和“chryos”，分別代表太陽和黃金的意思，因此屬植物的花序常呈現金黃色#2。永久花是30-70公分的芳香灌木#3，帶有咖哩味#4，在5-6月開黃花#5。義大利永久花因生長在地中海流域不同地區的差異，還能再細分6個亞種#6，法國科西嘉島上的永久花品種主要有亞種microphyllum (H. italicum ssp. microphyllum)和italicum (H. italicum ssp. italicum)兩種#6-7。
【生理活性】
即便品種相同，精油主成分仍有差異。亞種microphyllum來自義大利薩丁尼亞島、希臘的克里特島和法國科西嘉島。克里特島的主成分為β-桉葉烯(β-selinene，16.7-17.1%)和γ-薑黃烯 (γ-curcumene，6.6-13.7%)，薩丁尼亞的是乙酸橙花酯(neryl acetate，17.6-56.1%)，科西嘉島上的乙酸橙花酯含量經檢測普遍較高(41.5-55.7%)#8-9。#7
來自科西嘉的亞種italicum主成分同樣是乙酸橙花酯(15.8-42.5%)，次要成分有義大利酮I (11.0%)或是γ-薑黃烯(0.8-13.6%)，其它栽種地區還包括希臘、義大利托斯卡尼或厄爾巴島，精油成分都不太一樣#7。
有一些只存在於義大利永久花的特殊酮類成分#10，例如義大利酮(italidione)和其它β-雙酮(β-diketone)類成分，過去文獻紀載有義大利酮I (4, 6, 9-trimethyldec-8-en-3, 5-dione，5.5–11.0%)、義大利酮II (2,4,6,9-tetramethyl-8-decene-3,5-dione)#41、4, 6-dimethyloctan-3, 5-dione (0.2–2.4%)和義大利酮III (可能是3,5,7,10-tetramethylundec9-en-4,6-dione)#1-2, 11。這些分子以抗血腫聞名，所以永久花也有“芳療裡的山金車”(super arnica of aromatherapy)稱號，預期對皮膚退紅、血栓和瘀傷也有療效#7, 12。(p.s. 山金車能消血腫)
民俗療法
希臘哲人和植物學家泰奧弗拉斯托斯(Theophrastus)在其著作“Historia Plantarum”描述永久花(Heleiochrysos)(和蜂蜜混合)能治療燒燙傷以及有毒動物的叮咬#13。古籍紀錄常使用屬名，因此無法得知確切的品種，希臘醫生 Pedanius Dioscorides於西元40-70年撰寫的作品“De Materia Medica”，裡頭紀載蠟菊屬植物的花絲(filaments)酒浸泡液有治療泌尿系統不適、蛇咬、疝氣、坐骨神經痛和利尿等功效#14。文藝復興時期，荷蘭植物學家Herman Boerhaave認為蠟菊屬植物能緩解焦慮和歇斯底里#15。
義大利永久花對於呼吸道和皮膚的過敏或發炎皆有幫助#16-17。由於它的促進結瘢特性，所以能幫助皮膚再生以及傷口癒合#7。特別的是，即便早期臨床試驗尚未普遍，義大利永久花精油在治療傷口癒合、血腫、傷疤或皮膚相關疾病的評價依然讓人折服，並未遭遇任何挑戰或質疑#6, 18。
抗氧化
多樣的黃酮類成分構成永久花的抗氧化力，體外研究#19發現能抑制脂質的過氧化、消除自由基並展現抗氧化活性。銀鍛苷(tiliroside)和arzanol都是其中擁有顯著抗氧化功效的活性成分#19-20。
抗菌
實驗證明，義大利永久花精油和乙醚萃取物可有效抑制金黃色葡萄球菌的生長，即便是有抗藥性的菌株，抑制力也無差別#21-22，抗菌機轉可能是因為萜烯或黃酮類成分和微生物細胞膜作用，破壞細胞功能和結構#21, 23。
此外，根據Lorenzietal的研究#24，永久花精油和其成分香葉醇(geraniol)能提高抗生素在抗藥性微生物的抑菌力，實驗顯示在精油或香葉醇存在情形下，氯黴素(Chloramphenicol)對抗藥性產氣腸桿菌(E. aerogenes)、綠膿桿菌和鮑氏不動桿(A. baumannii)抑制效果明顯提升；氨苄青黴素、青黴素和諾氟沙星等抗生素對產氣腸桿菌的最低抑菌濃度也大幅下降。
精油也可抑制白色念珠菌#25，從研究推測主要應是類萜和含氧成分發揮它們的抗菌功效#25-26。
光保護和預防曬後紅斑
暴露在UVB光前先塗抹義大利永久花黃酮萃取物的豚鼠或人皮膚，能有效減少UVB引起的紅斑、皮膚溫度和刺痛，實驗顯示前24小時效果最佳，之後隨時間漸低，且除了能過濾UVB，也有很強的過濾UVA能力#27。作者覺得這萃取物應能應用在治療燒燙傷、輻射防護或防曬產品配方中。
抗發炎
外用整株義大利永久花的有機溶劑萃取物能減少小鼠因化學毒物誘發的耳朵腫脹#28，丁醇萃取物效果最好，之後依序是甲醇、乙酸乙酯、己烷以及二氯甲烷的萃取物。作者結論指出這些抗發炎功效也許是多種作用機轉表現的結果，包含抑制促進發炎酵素活性、自由基消除力和類似腎上腺皮質素(corticoids)的消炎機轉。
根據先前研究基礎，作者持續純化可能的有效成分，實驗顯示來自多種萃取物的純物質，包含苯乙酮、吡喃葡萄糖苷和黃酮類等成分皆有抗發炎的表現，例如4-hydroxy-3-(2-hydroxy-3-isopentenyl)acetophenone、12-hydroxytremetone-12-O-β-D-glucopyranoside、3-(2-hydroxyethyl) acetophenone-4-O-β-Dglucopyranoside、maltol-β-D-O-glucopyranoside、鼠麴草黃素 (gnaphaliin)、喬松素(pinocembrin)和銀鍛苷(tiliroside)等#19, 29-30。
術後修復
胸部整形術後，口服亞種serotinum永久花精油2滴每日2次持續10天，之後塗擦10%精油持續2-3個月，能有效減少局部發炎、腫脹、瘀傷與血腫#6, 31。
可能風險
果蠅和酵母菌實驗顯示，永久花精油在實驗中最大使用濃度0.3%下未觀察到明顯的基因損傷#32-33，反而還有部分減少突變的功效#33。一般認為長期使用義大利永久花精油都是安全的，只有一位69歲老太太使用永久花乳液舒緩皮膚乾癢時產生過敏#34，經進一步檢測確認是永久花萃取物引起，但作者再找10位志願者測試，並未發生過敏，所以僅是個案，實際上永久花在動物試驗反而是有抑制接觸性皮膚炎的效果#35-36。
永久花精油不會引發光刺激性#37。雖然有研究外用100%的義大利永久花精油在芳香療法上，這可能反映它的高安全性，然而一般並不建議這樣使用，更何況永久花還有潛在神經毒性的疑慮#6。為避免有些人可能產生皮膚刺激，永久花精油建議使用在皮膚的最高濃度應低於0.5%#38。
【芳療功效】
著有Clinical Aromatherapy的作者Jane Buckle偶爾會使用未稀釋的永久花治療皮膚瘀傷，都能獲得不錯效果，可是目前沒有相關研究支持#10。
1：1混合義大利永久花和歐洲南木蒿-高天藍烴品種(Artemisia arborescens-high chamazulene)精油，再使用椰子油稀釋至10%塗擦於輻射治療後的傷口一天數次，有助於傷口癒合、預防發炎或感染。使用含1：1混合義大利永久花和摩洛哥藍艾菊(Tanacetum annuum)精油的噴霧水(2ml/ 2ml/ 112ml)噴於患部，能有效減少皮膚刺激#39。
持續1周吸聞含有胡椒薄荷、甜羅勒和義大利永久花的複方精油，14位自覺疲憊的受測者經治療後，認為能有效大幅減少疲勞感#10, 40。
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後記
為了找出義大利酮的分子結構，幾乎花掉一整個下午…… 寫完後好奇用「4, 6, 9-trimethyldec-8-en-3, 5-dione」和「義大利酮」搜尋網頁，結果這篇似乎是第一個寫出義大利酮分子結構的網路中文資料？！！
參考文獻：
(1)Morone-Fortunato I, Montemurro C, Ruta C, Perrini R, Sabetta W, Blanco A, Lorusso E, Avato P. 2010. Essential oils, genetic relationships and in vitro establishment of Helichrysum italicum (Roth) G. Don ssp. italicum from wild Mediterranean germplasm. Ind Crops Prod. 32:639–649.
(2)Perrini, R., Morone-Fortunato, I., Lorusso, E., Avato, P., 2009. Glands, essential oils and in vitro establishment of Helichrysum italicum (Roth) G. Don ssp. microphyllum (Willd.) Nyman. Ind. Crops Prod. 29, 395–403.
(3)M. Galbany-Casals, J.M. Blanco-Moreno, N. Garcia-Jacas, I. Breitwieser, R.D. Smissen. Genetic variation in Mediterranean Helichrysum italicum (Asteraceae; Gnaphalieae): do disjunct populations of subsp. microphyllum have a common origin? Plant Biol., 13 (2011), pp. 678-687
(4)G. Appendino, M. Ottino, N. Marquez, F. Bianchi, A. Giana, M. Ballero, O. Sterner, B.L. Fiebich, E. Munoz. Arzanol, an anti-inflammatory and anti-HIV-1 phloroglucinol alpha-Pyrone from Helichrysum italicum ssp. microphyllum. J. Nat. Prod., 70 (2007), pp. 608-612
(5)A. Bianchini, F. Santoni, J. Paolini, A.F. Bernardini, D. Mouillot, J. Costa. Partitioning the relative contributions of inorganic plant composition and soil characteristics to the quality of Helichrysum italicum subsp. italicum (Roth) G. Don fil. essential oil. Chem. Biodivers., 6 (2009), pp. 1014-1033
(6)Viegas, D.A.; Palmeira-de-Oliveira, A.; Salgueiro, L.; Martinez-de-Oliveira, J.; Palmeira-de-Oliveira, R. Helichrysum italicum: From traditional use to scientific data. J. Ethnopharmacol. 2014, 151, 54–65.
(7)E. Guinoiseau, V. Lorenzi, A. Luciani, A. Muselli, J. Costa, J. Casanova and L. Berti. Biological properties and resistance reversal effect of Helichrysum italicum (Roth) G. Don, , 2013, Microbial pathogens and strategies for combating them : science, technology and education A. Méndez-Vilas, Ed. 2, 1073-1080.
(8)Cristofari G, Znini M, Majidi L, Costa J, Hammouti B, Paolini J. Helichrysum italicum subsp. italicum Essential Oil as Environmentally Friendly Inhibitor on the Corrosion of Mil Steel in Hydrochloric Acid, Int. J. Electrochem. Sci 2012; 7: 9024-9041.
(9)David Crow, L.Ac. (2013) Plants That Heal: Essays On Botanical Medicine.
(10)Jane Buckle, PhD, RN, Clinical Aromatherapy: Essential Oils in Healthcare (Third Edition. United Kingdom: Churchill Livingstone Elsevier, 2015)
(11)Maksimovic S., Tadic V., Skala D., Zizovic I., Separation of phytochemicals from Helichrysum italicum: An analysis of different isolation techniques and biological activities of prepared extracts, Phytochemistry 138 (2017) 9-28.
(12)Peace Rhind Jennifer. Essential Oils: A Handbook for Aromatherapy Practice. 2012: 148-149.
(13)J. Scarborough. Theophrastus on herbals and herbal remedies. J. Hist. Biol., 11 (1978), pp. 353-385
(14)P.F. Quer. Plantas Medicinales, El Dioscórides Renovado (14th ed.), Editoral Labor, S.A., Barcelona (1993)
(15)A.C. Lourens, A.M. Viljoen, F.R. van Heerden. South African Helichrysum species: a review of the traditional uses, biological activity and phytochemistry. J. Ethnopharmacol., 119 (2008), pp. 630-652
(16)J.B. Peris, G. Stubing, A. Romo. Plantas Medicinales de la Peninsula Iberica e Islas Baleares. Ediciones Jaguar, Madrid (2001)
(17)J.B. Peris, G. Stubing, B. Vanaclocha. Fitoterapia Aplicada. MICOF, Valencia (1995)
(18)K. Schnaubelt. Medical Aromatherapy – Healing with Essential Oils (1st ed.), Frogs Ltd., Berkeley (1999)
(19)Sala A, Recio MC, Schinella GR, Máñez S, Giner RM, Cerdá-Nicolás M, Ríos JL. Assessment of the anti-inflammatory activity and free radical scavenger activity of tiliroside. European Journal of Pharmacology. 2003; 461: 53-61.
(20)Rosa A, Pollastro F, Atzeri A, Appendino G, Melis MP, Deiana M, Incani A, Loru D, Dessì MA. Protective role of arzanol against lipid peroxidation in biological system. Chemistry and Physics of Lipids. 2011; 164: 24-32.
(21)A. Nostro, G. Bisignano, M. Angela Cannatelli, G. Crisafi, M. Paola Germano, V. Alonzo. Effects of Helichrysum italicum extract on growth and enzymatic activity of Staphylococcus aureus. Int. J. Antimicrob. Agents, 17 (2001), pp. 517-520
(22)A. Nostro, M.A. Cannatelli, A.D. Musolino, F. Procopio, V. Alonzo. Helichrysum italicum extract interferes with the production of enterotoxins by Staphylococcus aureus. Lett. Appl. Microbiol., 35 (2002), pp. 181-184
(23)A. Nostro, M.P. Germano, V. D'Angelo, A. Marino, M.A. Cannatelli. Extraction methods and bioautography for evaluation of medicinal plant antimicrobial activity. Lett. Appl. Microbiol., 30 (2000), pp. 379-384
(24)V. Lorenzi, A. Muselli, A.F. Bernardini, L. Berti, J.M. Pages, L. Amaral, J.M. Bolla. Geraniol restores antibiotic activities against multidrug-resistant isolates from gram-negative species. Antimucrobial Agents Chemother., 53 (2009), pp. 2209-2211
(25)J. Mastelic, O. Politeo, I. Jerkovic, N. Radosevic. Composition and antimicrobial activity of Helichrysum italicum essential oil and its terpene and terpenoid fractions. Chem. Nat. Compds., 41 (2005), pp. 35-40
(26)A. Palmeira-de-Oliveira, L. Salgueiro, R. Palmeira-de-Oliveira, J. Martinez-de-Oliveira, C. Pina-Vaz, J.A. Queiroz, A.G. Rodrigues. Anti-Candida activity of essential oils. Mini Rev. Med. Chem., 9 (2009), pp. 1292-1305
(27)R.M. Facino, M. Carini, M. Mariani, C. Cipriani. Anti-erythematous and photoprotective activities in guinea pigs and in man of topically applied flavonoids from Helichrysum italicum G. Don. Acta Ther., 14 (1988), pp. 323-345
(28)A. Sala, M. Recio, R.M. Giner, S. Manez, H. Tournier, G. Schinella, J.L. Rios. Anti-inflammatory and antioxidant properties of Helichrysum italicum. J. Pharm. Pharmacol., 54 (2002), pp. 365-371
(29)A. Sala, M.C. Recio, R.M. Giner, S. Manez, J.L. Rios. New acetophenone glucosides isolated from extracts of Helichrysum italicum with anti-inflammatory activity. J. Nat. Prod., 64 (2001), pp. 1360-1362
(30)A. Sala, M.C. Recio, G.R. Schinella, S. Manez, R.M. Giner, J.L. Rios. A new dual inhibitor of arachidonate metabolism isolated from Helichrysum italicum. Eur. J. Pharmacol., 460 (2003), pp. 219-226
(31)V. Voinchet, A.M. Giraud-Robert. Utilisation de l'huile essentielle d'hélichryse italienne et de l'huile végétale de rose musquée après intervention de chirurgie plastique réparatrice et esthétique. Phytothérapie (2007), pp. 67-72
(32)F. Bakkali, S. Averbeck, D. Averbeck, A. Zhiri, M. Idaomar. Cytotoxicity and gene induction by some essential oils in the yeast Saccharomyces cerevisiae. Mutat. Res., 585 (2005), pp. 1-13
(33)M. Idaomar, R. El-Hamss, F. Bakkali, N. Mezzoug, A. Zhiri, D. Baudoux, A. Munoz-Serrano, V. Liemans, A. Alonso-Moraga. Genotoxicity and antigenotoxicity of some essential oils evaluated by wing spot test of Drosophila melanogaster. Mutat. Res., 513 (2002), pp. 61-68
(34)C. Foti, S. Guida, A. Antelmi, P. Romita, M. Corazza. Allergic contact dermatitis caused by Helichrysum italicum contained in an emollient cream. Contact Dermatitis, 69 (2013), pp. 62-63
(35)Sala, A., 2001. Principios antiinflamatorios y antioxidantes de Helichrysum italicum (Roth) G. Don. PhD Thesis, University of Valencia, Valencia.
(36)J.L. Ríos, E. Bas, M.C. Recio. Effects of natural products on contact dermatitis. Curr. Med. Chem. – Anti-Inflammatory Anti-Allergy Agents, 4 (2005), pp. 65-80
(37)Opdyke DLJ 1979, Monographs on fragrance raw materials Food and Chemical Toxicology. 20
(38)Bouhlal, Meynadier et al, 1988. The cutaneous effects of the common concretes and absolutes used in the perfume industry. In: Lawrence BM (Ed) 2005, The antimicrobial/biological activity of essential oils. Allured, Carol Stream, Illinois, p 10-23
(39)Sylla Sheppard-Hanger. Use of Essential Oils and Natural Extracts to Help Counter Side Effects of Radiation During Cancer Treatment. (https://essentialthree.com/essential-oils-for-radiation-therapy/)
(40)Varney E, Buckle J. Effect of inhaled essential oils on mental exhaustion and moderate burnout: a small pilot study. J Altern Complement Med. 2013; 19(1): 69–71.
(41)Ascrizzi, Roberta & Flamini, Guido & Fraternale, Daniele. (2017). The antiaging properties of Helichrysum italicum (Roth) G.Don essential oil: collagenase and elastase inhibition activities.
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