一枝香
Vernonia cinerea (L.) Less.

別名：夜香牛、傷寒草、大號一枝香、紅花一枝香、生肌香、生枝香、返魂香、枝香草、星拭草、染色草、寄色草、四眼草、天紅草、夜仔草、夜牽牛、香山虎、消山虎、四時春、假鹹蝦、假鹹蝦花、紫野菊、縮蓋斑鳩菊、拐棍參

形態：

一年生直立草本。單葉，互生。葉紙質，卵形或長卵形或長橢圓形，兩面被短柔毛；先端漸尖或銳尖；葉緣鈍鋸齒；羽狀脈。頭狀花序排成總狀或圓錐，腋生或假頂生。總苞筒狀綠色，被伏毛，總苞片內外 3 層，先端具芒尖，筒狀花，淺紫色，筒長約 7 mm，花徑約 1.8 mm。花萼特化成絲狀冠毛，花冠瓣淺紫色，先端 5 裂，裂片線狀披針形，雄蕊 5 枚，聚藥；花絲絲狀，白色，長約 3.8 mm；花藥 2 室縱裂。子房倒圓錐形，白色，高約 1.4 mm，徑約 0.3 mm，被毛，子房上位 1 室；花柱長約 4.9 mm；柱頭 2 叉舌狀，熟紅深紫色突出雄蕊筒；胚珠 1 枚，卵球形，基生胎座。

典籍記載之相關效用：

一枝香的全草，味淡苦微甘性涼；全草有疏風散熱、拔毒消腫、安神鎮靜、消積化滯之效，主治感冒發熱、痢疾、疳積、跌打扭傷、蛇傷、乳癰、瘡癤腫毒等。《台灣藥用植物資源名錄468》

傷寒草《嶺南採藥錄》為夜香牛的全草或根，味苦辛性涼，有疏風清熱、除濕解毒、鎮靜安神、消積化滯之效。主治外感發熱、咳嗽、鼻炎、急性黃疸型肝炎、乳腺炎、濕熱腹瀉、痢疾、小兒驚風、小兒夜尿、白帶、疔瘡腫毒、毒蛇咬傷、跌打損傷等。《中華本草》

藥理研究：

抗關節炎作用 [1]：動物實驗發現一枝香花的乙醇提取物能逆轉大鼠佐劑致關節炎的主要病理變化。解熱、鎮痛、抗發炎作用 [2-6]：動物實驗證實一枝香葉的甲醇、氯仿、乙醚提取物具有鎮痛、解熱、消炎活性。甲醇提取物對酵母誘導大鼠發熱具有與對照藥撲熱息痛 (Paracetamol) 相當的降溫解熱作用。全草甲醇提取物對急慢性發炎反應有照藥 phenylbutazone 相當的改善作用。全草醇提取的抗氧化、神經保護和鈣離子通道抑制潛力，使得對長春新鹼致大鼠痛性神經病變和慢性縮窄性坐骨神經損傷致大鼠神經病理性疼痛具改善作用。抗菌作用 [7-9]：一枝香的苯提取實驗顯示有廣譜的抗菌活性。提取物影響銅綠假單胞菌細胞結構來抗菌。甲醇提取抑制白色念珠菌的生長。抗癌作用 [10★-15]：由一枝香莖部乙醇提取分離的 vernolide A、B 對 KB、DLD-1、NCI-661、Hela 人類癌細胞具細胞毒活性。一枝香倍半萜內酯 vernolide-A 通過調節 p53 和 caspase-3 的基因表達和調節 NF-κB 介導的 bcl-2 的活化，誘導 B16F10 黑色素瘤細胞的細胞凋亡。Vernolide-A 能增強 B16F10 轉移性黑素瘤負載小鼠的免疫反應，抑制黑色素瘤轉移進程。機轉實驗證明一枝香可以通過調節基質金屬蛋白酶、血管內皮生長因子、脯氨醯羥化酶、賴氨醯氧化酶、ERK-1、ERK-2、TIMPs、nm23 和轉移性肺組織促炎細胞因子的基因表達，抑制黑色素細胞在小鼠的肺轉移浸潤。一枝香的 8α-(2'Z-tigloyloxy)-hirsutinolide-13-O-acetate能抑制在膠質瘤 U251MG 細胞、乳癌 MDA-MB-231 細胞株異常 STAT3 的活性及抑制細胞株存活率。一枝香二氯甲烷部位能誘導 HeLa、A549、MCF-7、Caco-2 等癌細胞的細胞凋亡，並抑制多藥阻抗 (MDR) 轉運而促進癌細胞的藥物吸收和敏感。抗瘧活性 [16]：一枝香醇提取的 8α-tigloyloxy-hirsutinolide-13-O-acetate, 8α-(4-hydroxymethacryloyloxy)- hirsutinolide-13-O-acetate, vernolides D 對奎寧抗性 W2 惡性瘧原蟲有拮抗活性。保肝作用 [17]：動物實驗發現一枝香葉子粉末能改善四氯化碳誘導的大鼠肝功能障礙。抗氧化、抗發炎作用 [18-19]：一枝香甲醇提取在角叉菜膠誘導腳水腫實驗動物上，具有清除自由基、提高抗氧化酶活性、下調一氧化氮和炎性細胞因子的作用。一枝香甲醇提取抑制 LPS 刺激巨噬細胞的促炎性細胞因子、iNOS 和 COX-2 表達。戒菸作用 [20-21]：補充一枝香和運動會改變主動吸煙者的氧化應激狀態和 b-內啡肽釋放，可減少吸煙率。人類細胞色素 P450 2A6 (CYP2A6) 和單胺氧化酶 (MAO-A 和 MAO-B) 分別催化菸鹼和多巴胺代謝，是尼古丁依賴兩個治療靶點。一枝香分離黃酮類化合物與 hirsutinolides，對 CYP2A6 與 MAOs 有不同模式的抑制作用。提升化療作用 [22-23]：動物實驗發現一枝香提取物不影響化療藥物環磷醯胺 (cyclophosphamide, CTX) 化療效果，但對 CTX 所引起的小鼠免疫抑制和氧化應激具改善作用。動物實驗發現一枝香甲醇提取物不影響放射治療功效，仍顯著提升動物的抗氧化和抗發炎狀態。免疫調節作用 [24]：一枝香和vernolide A 在 BALB/c 小鼠通過增強細胞因子 IL-2 和 IFN-γ 的產生來調節細胞毒性T淋巴細胞、自然殺傷細胞、抗體依賴性細胞毒性和補體介導的細胞毒性。綜述 [25]：回顧一枝香具有抗炎、抗糖尿病藥、神經保護、抗癌、抗病毒、抗微生物等活性。

化學成分研究：

一枝香根部分離出 3b-acetoxyurs-19-ene 命名為lupeol acetate [26]。★ 莖部乙醇提取中分離鑒定出兩種新的倍半萜內酯 vernolide A、B [10]。一枝香莖部分離到 vernolide C、D, 8α-tigloyloxy-hirsutinolide-13-O-acetate, 8α-epoxymethacryloyloxy- hirsutinolide-13-O-acetate, 8α-tigloyloxyhirsutinolide, hirsutinolide-13-O-acetate, piptocarphin D, 8α-(4-hydroxymethacryloyloxy)-hirsutinolide-13-O-acetate [27]。全草分離到 vernocinolide A, 8α-[4-hydroxytigloyloxy]-hirsutinolide-13-O-acetate, 8α-[4-hydroxytigloyloxy]-10-hydroxyhirsutinolide-13-O-acetate, 8α-tigloyloxyhirsu tinolide, 8α-tigloyloxyhirsutinolide-13-O-acetate, vernolide A, vernolide B, 8α-[2- methylacryloyloxy]-hirsutinolide, 8α-[2-methylacryloyloxy]-hirsutinolide-13-O- acetate, 8α-[2-methylacryloyloxy]-1b,4b-epoxy-1α-methoxy-10bH-germacra-5E, 7(11)-dien-12,6-olide, 8α-[2-methylacryloyloxy]-1b,4b-epoxy-1α-methoxy-13-O- acetate-10bH-germacra-5E,7(11)-dien-12,6-olide 等倍半萜內酯 [28]。全草得到具神經生長因子誘導活性的 (+)-lirioresinol B, stigmasterol, stigmasterol-3-O-b- D-glucoside, 4-sulfo-benzocyclobutene；及 (-)-clovane-2,9-diol, caryolane- 1,9b-diol, apigenin, chrysoeriol, luteolin, thermopsoside, luteolin-7-O-b-D-glucoside, quercetin, apigenin-4'-O-b-D-glucoside, hyperin, b-amyrin aceate, lupeol acetate [29]。葉部甲醇提取含有 gallic acid, rutin, quercetin, caffeic acid, ferulic acid [30]。花的正己烷提取含有 8α-hydroxyhirsutinolide, 8α-hydroxyl-1-O-methylhirsutinolide、8α-tigloyloxy hirsutinolide, 8α-tigloyloxyhirsutinolide-13-O-acetate, 8α-(2-methylacryloyloxy)- hirsutinolide-13-O-acetate, 8α-(2-methylacryloyloxy)-1α-methoxyhirsutinolide-13-O- acetate, vernolide A、B, hirsutinolide-13-O-acetate。莖葉含有 8α-(2’Z-tigloyloxy)- hirsutinolide, 8α-(2’Z-tigloyloxy)-hirsutinolide-13-O-acetate, 8α-(4-hydroxytigloyl oxy)-hirsutinolide, 8α-hydroxy-13-O-tigloyl-hirsutinolide, 8α-(2-methylacryloyloxy)- hirsutinolide, 8α-tigloyloxyhirsutinolide, 8α-tigloyloxyhirsutinolide-13-O-acetate, 8α-(2-methylacryloyloxy)-hirsutinolide-13-O-acetate, vernolide A、B, 8α-hydroxy hirsutinolide, loliolide, isololiolide, (3R)-3-hydroxy-ionone, apigenine, (9Z,12S,13S)- dihydroxy-9-octadecanoic acid [31-32]。一枝香根部揮發油主要是倍半萜烴，含有 α-muurolene, b-caryophyllene, α-selinene, cyperene, α-gurjunene 等成分 [33]。

參考文獻：

  1. Latha, R. M., Geetha, T. and Varalakshmi, P. (1998) Effect of Vernonia cinerea Less flower extract in adjuvant-induced arthritis, Gen. Pharmacol., 31 (4): 601-6
  2. Gupta, M., Mazumder, U. K., Manikandan, L., Bhattacharya, S., Haldar, P. K. and Roy, S. (2003) Evaluation of antipyretic potential of Vernonia cinerea extract in rats, Phytother. Res., 17 (7): 804-6
  3. Iwalewa, E. O., Iwalewa, O. J. and Adeboye, J. O. (2003) Analgesic, antipyretic, anti-inflammatory effects of methanol, chloroform and ether extracts of Vernonia cinerea less leaf, J. Ethnopharmacol., 86 (2-3): 229-34
  4. Mazumder, U. K., Gupta, M., Manikandan, L., Bhattacharya, S., Haldar, P. K. and Roy, S. (2003) Evaluation of anti-inflammatory activity of Vernonia cinerea Less. extract in rats, Phytomedicine, 10 (2-3): 185-8
  5. Thiagarajan, V. R., Shanmugam, P., Krishnan, U. M. and Muthuraman, A. (2014) Ameliorative effect of Vernonia cinerea in vincristine-induced painful neuropathy in rats, Toxicol. Ind. Health, 30 (9): 794-805
  6. Thiagarajan, V. R., Shanmugam, P., Krishnan, U. M. and Muthuraman, A. (2014) Ameliorative potential of Vernonia cinerea on chronic constriction injury of sciatic nerve induced neuropathic pain in rats, An. Acad. Bras. Cienc., 86 (3): 1435-50
  7. Gupta, M., Mazumder, U. K., Manikandan, L., Haldar, P. K., Bhattacharya, S. and Kandar, C. C. (2003) Antibacterial activity of Vernonia cinerea, Fitoterapia, 74 (1-2): 148-50
  8. Latha, L. Y., Darah, I., Kassim, M. J. and Sasidharan, S. (2010) Antibacterial activity and morphological changes of Pseudomonas aeruginosa cells after exposure to Vernonia cinerea extract, Ultrastruct. Pathol., 34 (4): 219-25
  9. Latha, L. Y., Darah, I., Jain, K. and Sasidharan, S. (2011) Effects of Vernonia cinerea less methanol extract on growth and morphogenesis of Candida albicans, Eur. Rev. Med. Pharmacol. Sci., 15 (5): 543-9
  10. ★Kuo, Y. H., Kuo, Y. J., Yu, A. S., Wu, M. D., Ong, C. W., Yang Kuo, L. M., Huang, J. T., Chen, C. F. and Li, S. Y. (2003) Two novel sesquiterpene lactones, cytotoxic vernolide-A and -B, from Vernonia cinerea, Chem. Pharm. Bull. (Tokyo), 51 (4): 425-6
  11. Pratheeshkumar, P. and Kuttan, G. (2011) Vernolide-A, a sesquiterpene lactone from Vernonia cinerea, induces apoptosis in B16F-10 melanoma cells by modulating p53 and caspase-3 gene expressions and regulating NF-κB-mediated bcl-2 activation, Drug Chem. Toxicol., 34 (3): 261-70
  12. Pratheeshkumar, P. and Kuttan, G. (2011) Effect of vernolide-A, a sesquiterpene lactone from Vernonia cinerea L., on cell-mediated immune response in B16F-10 metastatic melanoma-bearing mice, Immunopharmacol. Immunotoxicol., 33 (3): 533-8
  13. Pratheeshkumar, P. and Kuttan, G. (2011) Vernonia cinerea Less. inhibits tumor cell invasion and pulmonary metastasis in C57BL/6 mice, Integr Cancer Ther., 10 (2): 178-91
  14. Appadath Beeran, A., Maliyakkal, N., Rao, C. M. and Udupa, N. (2014) The enriched fraction of Vernonia cinerea L. induces apoptosis and inhibits multi-drug resistance transporters in human epithelial cancer cells, J. Ethnopharmacol., 158 Pt A: 33-42
  15. Youn, U. J., Miklossy, G., Chai, X., Wongwiwatthananukit, S., Toyama, O., Songsak, T., Turkson, J. and Chang, L. C. (2014) Bioactive sesquiterpene lactones and other compounds isolated from Vernonia cinerea, Fitoterapia, 93: 194-200
  16. Chea, A., Hout, S., Long, C., Marcourt, L., Faure, R., Azas, N. and Elias, R. (2006) Antimalarial activity of sesquiterpene lactones from Vernonia cinerea, Chem. Pharm. Bull. (Tokyo), 54 (10): 1437-9
  17. Gokilaveni, C., Nishadh, A. and Selvi, V. (2006) Ameliorative role of Vernonia cinerea in carbon tetrachloride induced hepatic dysfunction in rats, Anc. Sci. Life., 25 (3-4): 1-5
  18. Kumar, P. P. and Kuttan, G. (2009) Vernonia cinerea L. scavenges free radicals and regulates nitric oxide and proinflammatory cytokines profile in carrageenan induced paw edema model, Immunopharmacol. Immunotoxicol., 31 (1): 94-102
  19. Pratheeshkumar, P. and Kuttan, G. (2011) Modulation of immune response by Vernonia cinerea L. inhibits the proinflammatory cytokine profile, iNOS, and COX-2 expression in LPS-stimulated macrophages, Immunopharmacol. Immunotoxicol., 33 (1): 73-83
  20. Leelarungrayub, D., Pratanaphon, S., Pothongsunun, P., Sriboonreung, T., Yankai, A. and Bloomer, R. J. (2010) Vernonia cinerea Less. supplementation and strenuous exercise reduce smoking rate: relation to oxidative stress status and b-endorphin release in active smokers, J. Int. Soc. Sports Nutr., 7: 21
  21. Prasopthum, A., Pouyfung, P., Sarapusit, S., Srisook, E. and Rongnoparut, P. (2015) Inhibition effects of Vernonia cinerea active compounds against cytochrome P450 2A6 and human monoamine oxidases, possible targets for reduction of tobacco dependence, Drug Metab. Pharmacokinet., 30 (2): 174-81
  22. Pratheeshkumar, P. and Kuttan, G. (2010) Ameliorative action of Vernonia cinerea L. on cyclophosphamide-induced immunosuppression and oxidative stress in mice, Inflammopharmacology, 18 (4): 197-207
  23. Pratheeshkumar, P. and Kuttan, G. (2011) Protective role of Vernonia cinerea L. against γ radiation--induced immunosupression and oxidative stress in mice, Hum. Exp. Toxicol., 30 (8): 1022-38
  24. Pratheeshkumar, P. and Kuttan, G. (2012) Modulation of cytotoxic T lymphocyte, natural killer cell, antibody-dependent cellular cytotoxicity, and antibody-dependent complement-mediated cytotoxicity by Vernonia cinerea L. and vernolide-A in BALB/c mice via enhanced production of cytokines IL-2 and IFN-γ, Immunopharmacol. Immunotoxicol., 34 (1): 46-55
  25. Dogra, N. K. and Kumar, S. (2015) A review on ethno-medicinal uses and pharmacology of Vernonia cinerea Less, Nat. Prod. Res., 29 (12): 1102-17
  26. Misra, T. N., Singh, R. S., Srivastava, R., Pandey, H. S., Prasad, C. and Singh, S. (1993) A New Triterpenoidal from Vernonia cinerea, Planta Med., 59 (5): 458-60
  27. Chea, A., Hout, S., Long, C., Marcourt, L., Faure, R., Azas, N. and Elias, R. (2006) Antimalarial activity of sesquiterpene lactones from Vernonia cinerea, Chem. Pharm. Bull. (Tokyo), 54 (10): 1437-9
  28. Chen, X., Zhan, Z. J. and Yue, J. M. (2006) Sesquiterpenoids from Vernonia cinerea, Nat. Prod. Res., 20 (2): 125-9
  29. Zhu, H. X., Tang, Y. P., Pan, L. M. and Min, Z. D. (2008) Studies on bioactive constituents of whole herbs of Vernonia cinerea, Zhongguo Zhong Yao Za Zhi, 33 (16) 1986-8;  Zhu, H., Tang, Y., Min, Z. and Gong, Z. (2009) Bioactive constituents from whole herbs of Vernonia cinerea (II), Zhongguo Zhong Yao Za Zhi, 34 (21): 2765-7
  30. Rajamurugan, R., Selvaganabathy, N., Kumaravel, S., Ramamurthy, Ch, Sujatha, V., Suresh Kumar, M. and Thirunavukkarasu, C. (2011) Identification, quantification of bioactive constituents, evaluation of antioxidant and in vivo acute toxicity property from the methanol extract of Vernonia cinerea leaf extract, Pharm. Biol., 49 (12): 1311-20
  31. Youn, U. J., Park, E. J., Kondratyuk, T. P., Simmons, C. J., Borris, R. P., Tanamatayarat, P., Wongwiwatthananukit, S., Toyama, O., Songsak, T., Pezzuto, J. M. and Chang, L. C. (2012) Anti-inflammatory sesquiterpene lactones from the flower of Vernonia cinerea, Bioorg. Med. Chem. Lett., 22 (17): 5559-62
  32. Youn, U. J., Miklossy, G., Chai, X., Wongwiwatthananukit, S., Toyama, O., Songsak, T., Turkson, J. and Chang, L. C. (2014) Bioactive sesquiterpene lactones and other compounds isolated from Vernonia cinerea, Fitoterapia, 93: 194-200
  33. Joshi, R. K. (2015) GC/MS analysis of the essential oil of Vernonia cinerea, Nat. Prod. Commun., 10 (7): 1319-20

討論話題：

  • 一枝香又別名“大號一枝香”，那麼有沒有“小號一枝香”？
    有，金絲桃科田基黃也稱小號一枝香，全草味甘苦性平，是解熱劑；水煎服治瘰癧、腫瘤、胃腸虛弱。《甘偉松，台灣藥用植物誌III-552；台灣植物藥材誌II-32》
1 / 2