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Family Asteraceae
Apanang-gubat
Eupatorium chinense L.
JAPANESE THOROUGH-WORT

Chen gan cao

Scientific names Common names
Eupatorium chinense L. Apanang-gubat (Tag.)
Eupatorium crenatifolium Hand.-Mazz. Japanese bog orchid (Engl.)
Eupatorium glehni F.Schmidt ex Trautv. Japanese boneset (Engl.)
Eupatorium hakonense Nakai Japanese thorough-wort (Engl.)
Eupatorium japonicum Thunb.  
Eupatorium laciniatum Kitam.  
Eupatorium mairei Leveille  
Eupatorium melanadenium Hance  
Eupatorium sachalinense (F.Schmidt) Makino  
Eupatorium sinense J.F.Gmel.  
Eupatorium tozanense Hayata  
Eupatorium wallichii DC.  
Eupatorium japonicum Thunb. is a synonym of Eupatorium chinense L. The Plant List
Eupatorium chinense L. is an accepted name. The Plant List

Other vernacular names
CHINESE: Bai tou po, Chen gan cao.

Botany
Apanang-gubat is an erect, leafy branched, smooth herb, 60 to 90 meters high. Leaves are fragrant, up to 19 centimeters long, divided quite to the base into three segments - the upper leaves subtending the branches of the inflorescence being deeply divided. Segments are elliptic-lanceolate or elliptic-ovate, up to 13 centimeters long, pointed at both ends, and toothed at the margins. Inflorescence is terminal, measuring up to 14 centimeters across. Flowering heads are 3 to 4 millimeters across. Flowers are white and fragrant.

Distribution
- In thickets at low altitudes in the Batan Islands.
- Occurs in Japan to China and Taiwan.

Constituents
- Yields essential oil thymol.
- Contains pyrrolizidine alkaloids—class of hepatotoxic and tumorigenic compounds that have been detected in herbal plants and dietary supplements.
- Study of flowers and leaves yielded volatile oils. Main constituents were germacrene D (27.3%, 37.1%), gemacrene B (12.4%, 11.7%) and β-caryophyllene (8.6%, 10.1%). (9)
- Ethyl acetate fraction from ethanol extract yielded three new triterpenoid compounds (1-3). (see study below) (14)
- Study of whole plant yielded ten new sesquiterpenoids, eupachinilides A-J. together with seven known sesquiterpenoids. eupachifolin D (11) budlein B (12), 8-beta-(4-hydroxytiglyloxy)-2-beta-hydroxy-1 alpha H, 6 beta H, 7 alpha H guai-310 (14), 11-13-trien-6,12-olide (13), 1,10-hydrobahia (14), 2 alpha hydroxyeupatolide (15), eupaserrin (16), and mllisorin B (17). (see study below) (16)

Properties
- Considered anodyne, antibacterial, antidandruff, antiviral.
- Carminative, diaphoretic, diuretic, nervine.
- Leaves and stems considered vermifuge.
- Studies have shown ovicidal, antibacterial, anti-inflammatory, anti-osteoporosis, hepatotoxic properties.

Toxicity concerns
- Contradictory reports on toxicity: Plant reported to be poisonous, especially the leaves. However, leaves have reported use as tea or flavoring.

Parts used
Leaves, roots.

Uses

Edibility
- In Japan, leaves consumed as tea or used as flavoring. (see toxicity note above)
- In Nepal, powdered plant used to prepare marcha, a fermenting cake from which liquor is distilled. (12)
Folkloric
- Leaves used as diuretic and anthelmintic.
- Also used as tea for indigestion.

- In China, used for diseases of women.
- Milky latex applied to goiter.
- Used by Rukai tribe of Wutai, southern Taiwan, for ulcer, fever, headaches, fractures. (10)
- Root is beneficial to the circulation and restorative to women after parturition.
- Herb soaked in oil is applied to the hair as treatment for dandruff.
Others
-
Fragrance: Fragrant leaves used to perfume hair and clothes. (12)

Studies
Pyrrolizidine Alkaloids:
Study on the pyrrolizidine alkaloid composition of three Chinese herbs (E. cannabinum, E. japonicum and Crotolaria assamica) yielded viridiflorine, cynaustraline, amabiline, supinine, echinatine, rinderine and isomers of these alkaloids were found in the Eupatorium species. (1)
Hepatotoxicity: Study concludes the alkaloid in Eupatorium species is metabolized to "pyrrole" and an N-oxide metabolite in the liver, but the hepatotoxicity is much lower when compared to that caused by Crotolaria. (2)
Pyrrolizidine Alkaloids / Hepatotoxic and Tumorigenic: Studies have indicated that pyrrolizidine alkaloids induce tumors via a genotoxic mechanism mediated by 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine(DHP)-derived DNA adduct formation. (3)
Ovicide and Larval Growth Inhibitor: In a study with test insects Drosophila melanogaster, an ovicide identified as coumarin and a larval growth inhibitor, a new sesquiterpene lactone called euponin, were isolated from leaf extracts. (5)
Antibacterial / Volatile Oils: Study of volatile oils showed significant antibacterial activities against Micrococcus tetragenus, Staphylococcus aureus, Escherichia coli, and Bacillus subtilis. (6)
Osteoporosis Prevention: A previous study showed bioactive constituents can reciprocally regulate adipogenic and osteogenic fates of bone marrow cells. This study showed stems extracts suppressed lipid accumulation and inhibited the expression of adipocyte markers. Results showed bioactive anti-adipogenic and pro-osteogenic components in the stem extracts, suggesting a potential as a functional food and therapeutic alternative for preventing osteoporosis and bone fractures. (7)
Anti-Inflammatory / COX and iNOS Suppression / Flowers: Study investigated the ethanol extracts of flowers on nuclear factor (NF)-kB activation and expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) by TLR agonists in murine macrophages. Results showed EJE can regulate TLR signaling pathways and suggests a potential as anti-inflammatory drug. (8)
Safety Issues on Pyrrolizidine Alkaloids: PAs have been shown to cause toxic reactions in humans, particularly veno-occlusive disease, when ingested with food and herbal medicines (ex: comfrey). PAs are found primarily in three plant families: Asteraceae (Eupatorium and Ageratum), Boraginaceae, and Fabaceae. Peilan, a commonly used Chinese herb, contains Eupatorium fortunii and E. japonicum. (11)
Eupalinin A / Autophagocytosis in Human Leukemia HL60 Cells: Eupalinin A, a natural phytoalexin, exhibited marked inhibitory effect on cell growth of HL60 cells. Results suggest the eupalinin A-induced cell death was mainly due to autophagy, initiated by increased ROS. (13)
• Triterpenoid Compounds / Cytotoxicity Study: Ethyl acetate fraction from thanol extract yielded three new triterpenoid compounds (1-3). All the isolated compounds were tested for in vitro cytotoxic activities against HepG2, HGC-27, and MDA-MB-231 cancer cell lines. (see study below) (14)

• Thymol Derivatives / Cytotoxicity Against Cancer Cell Lines / Roots: Study of root yielded two new thymol derivatives, compounds 1 and 2. The compounds were tested in vitro for cytotoxic activities against three cancer cell lines i.e., CNE2, Caski and HGC-27. Compound 1 showed notable cytotoxic activity against the 3 cancer cell lines with IC50 values ranging from 4.2 to 11.9 µM. (15)
• Cytotoxic Sesquiterpenoids Against Cancer Cell Lines: Study of whole plant yielded ten new sesquiterpenoids, eupachinilides A-J. together with seven known sesquiterpenoids. Eupachinilides A, E, F, and I exhibited moderate cytotoxic activities against several tumor cell lines. (see constituents above) (16)
• Antipyretic: Study evaluated the antipyretic effect of E. chinense in rats. The content of arginine vasopressin (AVP) in ventral septal area and blood plasma, cyclic adenosine monophosphatre (cAMP) levels of hypothalamus and blood plasma were determined by ELISA. Results showed E. chinense has strong antipyretic effect and may affect the production of AVP and cAMP in fever in rats. (17)
• Germacrane-type Sesquiterpenoids / Antiproliferative: Study of whole plant of E. chinense yielded ten new germacrane-type sesquiterpenoids (1-10). Compounds 3 and 4 exhibited cytotoxicity against a human breast cancer cell line (MDA-MB-231) with IC50 of 0.8 and 3.4 µM, respectively. Compounds 3-5 showed cytotoxicity against human hepatocellular carcinoma cell line (HepG2), with IC50 range from 3.6 to 7,6 µM. (18)

Availability
Wild-crafted.
Extracts and supplements in the cybermarket.

Updated October 2019 / August 2016

IMAGE SOURCE: File:Eupatorium japonicum3.jpg / KENPEI / 20 Oct 2007/ GNU Free Documentation License / Click on image to go to source page / Wikimedia Commons

Additional Sources and Suggested Readings
(1)
Pyrrolizidine alkaloid composition of three Chinese medicinal herbs, Eupatorium cannabinum, E. japonicum and Crotalaria assamica / Edgar JA, Lin HJ et al /
Am J Chin Med. 1992;20(3-4):281-8.
(2)
A comparative study on the hepatic toxicity and metabolism of Crotalaria assamica and Eupatorium species / Chan MY, Zhao XL, Ogle CW /
Am J Chin Med. 1989;17(3-4):165-70.
(3)
Pyrrolizidine Alkaloids - Tumorigenic Components in Chinese Herbal Medicines and Dietary Supplements / Peter P Fu, Ya-Chen Yang et al / Journal of Food and Drug Analysis, Vol. 10, No. 4, 2002, Pages 198-211
(4)
Eupatorium japonicum / Plants For A Future
(5)
Coumarin and euponin, two inhibitors for insect development from leaves of Eupatorium japonicum
. / Nakajima, S.; Kawazu, K. / Agricultural and Biological Chemistry 1980 Vol. 44 No. 12 pp. 2893-2899
(6)
Extraction,GC-MS Analysis and Antibacterial Activities of Volatile Oils from Eupatorium fortune / LIU Jie,JIN Yan / Journal of Hebei Agricultural Sciences, 2011-03
(7)
Reciprocal Regulation of Adipocyte and Osteoblast Differentiation of Mesenchymal Stem Cells by Eupatorium japonicum Prevents Bone Loss and Adiposity Increase in Osteoporotic Rats. / Kim MJ, Jang WS, Lee IK, Kim JK, Seong KS, Seo CR, Song NJ, Bang MH, Lee YM, Kim HR, Park KM, Park KW. / J Med Food. 2014 Jun 13.
(8)
Japanese bog orchid (Eupatorium japonicum) extract suppresses expression of inducible nitric oxide synthase and cyclooxygenase-2 induced by toll-like receptor agonists / Gyo-Jeong Gu, Sang-Hoon Eom, Hwa-Jeong Shin, Ji Hun Paek, Songmun Kim, Soon Sung Lim, Hyung-Sun Youn / Food Science and Biotechnology, June 2013, Volume 22, Issue 3, pp 811-815
(9)
Volatile constituents of essential oils isolated from flowers and leaves of Eupatorium cannabinum L. from Iran /
Mehdi Mirza*, Mehrdokht Najafpour Navaei and Mohammad Dini / Iranian Journal of Pharmaceutical Research (2006) 2: 149-152
(10)
A Preliminary Study on Diverse Plant Uses of Rukai Tribe in Wutai District of Pingtung County, Southern Taiwan / Sheng-Zehn Yang* and Yueh-Ju Gao / Taiwania, 56(1): 7-16, 2011
(11)
SAFETY ISSUES AFFECTING HERBS: PYRROLIZIDINE ALKALOIDS / Subhuti Dharmananda, Ph.D., Director, Institute for Traditional Medicine, Portland, Oregon /
(12)
Eupatorium chinense / Edible Uses (Plants and People of Nepal, Manandhar, 2002) / Useful Tropical Plants
(13)
Eupalinin A isolated from Eupatorium chinense L. induces autophagocytosis in human leukemia HL60 cells / ITOH Tomohiro; ITO Yuko; OHGUCHI Kenji; OHYAMA Masayoshi; IINUMA Munekazu; OTSUKI Yoshinori; NOZAWA Yoshinori; AKAO Yukihiro / Bioorganic & medicinal chemistry, 2008; Vol 16, No 2: pp. 721-731
(14)
Three new terpenoids from the Eupatorium chinense / Xiao=Qin Yu et al / Phytochemistry Letters, June 2917; Vol 20: pp 224-227 / https://doi.org/10.1016/j.phytol.2017.04.004
(15)
Thymol derivatives from the roots of Eupatorium chinense and their cytotoxic activities / Qing-Qing Zhang, Zhi-Ying Sun, Xue-Yun Feng, Run-Jie Chen et al / Phytochemistry Letters, Feb 2019; Vol 29: pp 165-168 / https://doi.org/10.1016/j.phytol.2018.12.008
(16)
Cytotoxic Sesquiterpenoids from Eupatorim chinense / Sheng=Ping Yang, Jun Huo, Ying Wang et al / Journal of Natural Products, May 2004; 57(4): pp 638-643 / DOI: 10.1021/np0304159
(17)
Antipyretic Effects of Eupatorium chinense and Its Mechanism / Yi-ping Jiang, Jiang-ping Xu / Chinese Herbal Medicines, 2015; 7(4): pp 323-327 / DOI: 10.1016/S1674-6384(15)60059-4
(18)

Germacrane-Type Sesquiterpenoids with Antiproliferative Activities from Eupatorium chinense / Xiaoqin Yu, Qingqing Zhang, Li Tian, Zhiyong Guo, Chengxiong Liu et al / J. Nat. Prod., 2018; 81(1): pp 85-91 / https://doi.org/10.1021/acs.jnatprod.7b00693

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