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Family Simarubaceae
Mamikil
Harrisonia perforata (Blanco) Merr.
Niu jin guo

Scientific names Common names
Anisifolium pubescens (Wall.) Kuntze Asimau (Tag.)
Feroniella puberula Yu. Tanaka Bakit (Ilk., Pamp.)
Feroniella pubescens (Wall. ex Hook.f.) Yu. Tanaka Dagiangas (Mbo.)
Harrisonia citrinaecarpa Elmer Kamuñgi (Sul.)
Harrisonia perforata (Blanco) Merr. Laiya (Tag.)
Lasiolepis multijuga Benn. Mamikil (Tag.)
Lasiolepis paucijuga Benn. & R.Br. Muntani (Bis.)
Limonia pubescens Wall. ex Hook.f. Sapleng (Sbl.)
Paliurus dubius Blanco Sapsapang (Ilk.)
Paliurus perforatus Blanco  
Harrisonia perforata (Blanco) Merr. is an accepted name. The Plant List

Other vernacular names
CHINESE: Nin jin guo.
INDONESIA: Sesepang, Garut, Ri kengkeng.
LAOS: Don kin ta.
MALAYSIA: Kait-kait.
THAILAND: Khonthaa, Kalanthaa, Seefan, Seefan khonthaa, Naam chee, Mee-chee.
VIETNAM: S[aa]n, Da da, H[ar]i s[ow]n.

Botany
Mamikil is a somewhat climbing and nearly erect shrub, growing from 2 to 4 meters in height. Branches are armed with short, sharp spines. Leaves are pinnate, with an unpaired terminal leaflet up to 20 centimeters long. Leaflets are 1 to 15 pairs, oblong-ovate, 1.5 to 3.5 centimeters long, and with entire or crenate margins. Flowers are white, and borne on terminal racemes 3 to 5 centimeters long. Fruit is somewhat globular, fleshy, smooth, and 1 to 1.5 centimeters in diameter.

Distribution
- In thickets at low altitudes in Ilocos Sur, Nueva Viscaya, Pangasinan, Rizal, and Batangas Provinces in Luzon; and in Samar and Mindanao.
- Also occurs in Burma to southern China and Java.

Constituents
- Roots yield a bitter principle, abundant in the cortical parenchyma. The organic base was provisionally called mamikilina, and the bitter principle, harrisonine.
- Extraction of dried leaves yielded a novel tetranortriterpenoid (limonoid), perforatin, of the obacunol class. (1)
- Study yielded eight limonoids (1–8) including three A, B and D-seco-16-nor-type ones, 5,6-dehydrodesepoxyharperforin C2 (1), harrpernoid B (2), and its C-9S epimer, harrpernoid C (3), along with six known compounds (9–14), were isolated from fruits of Harrisonia perforata. (see study below) (4)
- Fractionation of ethanol extract of fruits yielded 18 compounds[ 12 were elucidated as Ethyl 3,4,5-Trihdroxybenzoate (1)、4-ethylgallic acid (2)、Hydroxyhydroquinone (3)、Gallic acid (4)、β-Sitosterol (5)、β-Daucosterol (6)、Stigmasterol (7)、Protocatechuic acid (8)、Palmitic acid (9)、Linoleic acid (10)、Cis-Oleic acid (11)、5-hydroxymethyl-2-Furancarboxaldehyde (12). (3)
- Fractionation of a petroleum ether extract yielded 29 compounds, amounting to 69.67% of the total detected constituents. The major constituents were identified as Z-9,12-Octadecadien-1-ol (12.35%), Palmitic acid (9.67%), Z-9,17-octadecadienal (8.97%), Ethyl Oleate (5.81%), β-Sitosterol (4.88%), Ethyl Linoleate (4.10%). Linoleic acid, palmitic acid, and ß-sitosterol were the common liposoluble components in two extractions. (11)
- Alcohol extraction yielded 12 compounds amounting to 71.00% of the total detected constituents. The major constituents were identified as Quinic acid (40.44%), pyrogallol (14.64%),5-(hydroxymethyl)-2-Furancarboxaldehyde (5.89%). (3)
- Study of fruit isolated 8 compounds: caryolane-1,9beta-diol (1), gallic acid (2), 4-O-ethylgallic acid (3), syringic acid ethyl ester (4), protocatechuic acid (5), stigmasterol (6), beta-daucoster (7), beta-sitosterol (8). (19)
- Study of H. perforata isolated perforalactone A, a new 20S quassinoid, together with two biosynthetically related new quassinoids. (see study below) (23)

Properties
- Antidiarrheal, anti-dysentery.
- Studies suggest antimicrobial, antioxidant, anti-malarial, anti-inflammatory properties.

Parts used
Shoots, bark.

Uses

Folkloric
- In the Philippines, decoction of root bark used as remedy for diarrhea and dysentery; also used against cholera.
- Decoction of stems used for diarrhea.
- In the Dutch East Indies, shoots are used as a remedy for diarrhea.
- In Thailand, the wood was also recorded as medicinal. Roots used in treatment of fever.
- Ashes of roasted leaves mixed with oil and applied locally to relieve itching; crushed leaves also used for the same.
- Harrisonia perforata is one of five root components of Benchalokawichian (BCW), a Thai traditional herbal formulation, used as antipyretic and to treat skin disorders. (10)


Studies
Antimalarial:
A South Vietnam study identified 49 plants traditionally used to treat malaria. Harrisonia perforata was one of six plants with possible novel antimalarial compounds, with antiplasmodial activity (IC50 ranging from 0.4 to 8.6 mu g/ml) with good selectivity. (2)
Antioxidant: Parts of petroleum ether, ethyl acetate and ethanol extract showed high antioxidant activity by the DPPH free radical scavenging method. (11)
• Limonoids / Cytotoxicity / Fruit: Study of fruits yielded eight limonoids (1–8) including three A, B and D-seco-16-nor-type ones, 5,6-dehydrodesepoxyharperforin C2 (1), harrpernoid B (2), and its C-9S epimer, harrpernoid C (3), along with six known compounds (9–14). Limonoids 1-8 were evaluated for anti-tobacco mosaic virus and in vitro cytotoxicity against A549 and HL60 cell lines. Only compound 2, harrpernoid B, showed weak cytotoxicity. (see study below) (4)
Antimicrobial Activity: In a Cambodian study of 27 plant species for in vitro antibacterial and antifungal activities, Harrisonia perforata roots exhibited bactericidal effect against S. aureus and its roots and stems exhibited bactericidal effect against Mycobacterium smegmatis. (5)
Inhibitory Effect on Strep Mutans Adherence: Study showed A. paniculata, C. alata, Chinese black tea and Harrisonia perforata could inhibit adherence of S. mutans ATCC 25175. (6)
Anti-Inflammatory / Roots: Study investigated the in vivo and in vitro anti-inflammatory effect of an ethanolic root extract. Results showed significant reduction of inflammation in rat paw edema after carrageenan injection. The mechanism could be through suppression of pro-inflammatory cytokines. (9)
Anti-Inflammatory / Limonoids and Chromones: Study of fruits and roots yielded two new rearranged limonoids, harperforatin(1) and harperfolide (2), and a new chromone, harperamone (3), together with eight known compounds. Harperfolide (compound 2) exhibited potent anti-inflammatory activity via suppression of nitric oxide production. The effect was probably mediated by reduction of iNOS protein expression, attributable to the inhibitory action of LPS-induced NO production. (12)
Novel IDDP/ Apoptosis in Human Cancer Cells: Leaves of Harrisonia perforata have yielded limonoids. Haperforin B1, one of the isolated limonoids from the leaves of H. perforata, yielded an intermediate product, E-5-iodomethylene-6,6-dimethyl-5,6-dihydropyran-2-one (IDDP). IDDP was found more toxic to human cancer cell lines than haperforin B1. Study describes the IDDP synthesis and its in vitro anti-proliferative activity against several chemosensitive and resistant cancer cell lines, as well as its ability to induce cell death by apoptosis. (13)
Bactericidal / Staphylococcus aureus: Study evaluated 27 plant species in Cambodia for in vitro antibacterial and antifungal activities. H. perforata showed antimicrobial activity especially on Gram-positive bacteria, and showed a bactericidal effect against S. aureus (500 µg/ml) and M. smegatis (roots and stems, 250 µg/ml). (14)
Antimicrobial / Benchalokawichian: Study evaluated the antimicrobial activity of extracts from Benchalokawichian remedy and its components against clinical isolates. Harrisonia perforata and the other components showed antimicrobial activity against Candida albicans, and most Gram positive and Gram negative isolates. (15)
Antipyretic / Antinociceptive / Benchalokawichian: Study of root extract of BLW showed both antipyretic and antinociceptive properties in well-established animal models. (16)
Acute and Subchronic Toxicity Study: Water extract from Harrisonia perforata was studied for acute and subchronic toxicities in rats. At 5,000 mg/kg orally to male and female rats, the extract did not produce signs of toxicity. For subchronic toxicity testing with extract doses off 300, 600, and 1,200 mg/kbw orally for 90 days, there were no abnormalities in test groups compared to control. Results showed no acute and subchronic toxicities in rats.(17)
• Inhibitory Effect on Macrophage Activation / Antipyretic / Anti-Inflammatory / Roots: Study investigated the effect of H. perforata ethanol root extract on LPS-activated macrophage, J774A.1 cells. Results showed inhibition of LPS-activated nitric oxide (NO) production in a concentration dependent manner. There was also decrease in mRNA expression of cyclooxygenase-2 (COX-2), the enzyme required for prostaglandin synthesis in activated macrophage during inflammatory processes. Results suggest both antipyretic and anti-inflammatory activity. (21)
• Cytotoxicity / Human Epidermoid Carcinoma (KB-31) Cells / Stem Bark: Study evaluated the cytotoxic activity of lipophilic extracts of Thai herbs (Harrisonia perforata, P. pinnata, A. indica) against Human Breast Cancer (MCF-7) cells, Human Epidermoid Carcinoma (KB-31) cells and Monkey kidney (Vero) cells. H. perforata showed the highest cytotoxicity effect against KB-31 cells with IC50 of 191.06 µg/ml. (22)
• Quassinoids / Insecticidal: Study of H. perforata isolated perforalactone A, a new 20S quassinoid, together with two biosynthetically related new quassinoids. The compounds exhibited notable biological activities, including insecticidal activity against Aphis medicaginis. (23)
• Harperforin B1 / IDDP / Antiproliferative / Leaves: Analysis of leaves have yielded the presence of several limonoids belonging to the obacunol series. One of the isolated limonoids, haperforin B1, showed cytotoxic activity. Chemical synthesis of haperforin B1 yielded an intermediate product, E-5-iodomethylene- 6,6-dimethyl-5,6-dihydropyran-2-one (IDDP), which showed to be more cytotoxic to cancer cell lines than haperforin B1. Study investigated the antiproliferative activity of IDDP and its ability to induce apoptosis. Study showed an IC50 range from 0.07 to 0.50 µM, clearing indicating antiproliferative activity regardless of tumor cell origin (colon, lung, cervical carcinomas, breast carcinomas, etc.) with maximal efficacy against U87 glioblastoma (IC50=0.18 µM) and K562 leukemia (IC50=1=0.15 µM) cells. In vitro IDDP treatment led to a significant dose-dependent cell cycle arrest in the G2/M phase and induction of apoptosis in a time- and dose-dependent manner. (24)

Availability
Wild-crafted.

Last Update January 2017

IMAGE SOURCE: / Photo / Leaves / Leaves / Copyright © 2011 by Leonardo L. Co (contact: benctan@berkeley.edu) [ref. DOL28495] / Non-Commercial Use / click on image to go to source page / PhytoImages.siu.edu
OTHER IMAGE SOURCE: / Photo / Prickels / Rutaceae : Harrisonia perforata / Copyright © 2011 by Leonardo L. Co (contact: benctan@berkeley.edu) [ref. DOL28494 // Non-Commercial Use / click on image to go to source page / PhytoImages.siu.edu
OTHER IMAGE SOURCE: Herbarium Specimen / Harrisonia perforata (Blanco) Merr. / Specimen Elmer, Adolph Daniel Edward - 1344/ Creative Commons / click on image to go to source page / Tropicos.org. Missouri Botanical Garden. 08 Feb 2015

Additional Sources and Suggested Readings
(1)
Perforatin: a Novel Tetranortriterpenoid From Harrisonia perforata / LT Byrne, M Vantri, NM Phuong, MV Sargent, BW Skelton and AH White / Australian Journal of Chemistry 44 (1) 165 - 169
(2)
Antimalarial and cytotoxic activities of ethnopharmacologically selected medicinal plants from South Vietnam
/ Julie Nguyen-Pouplin, Hop Tran, Hung Tran et al / Journal of Ethnopharmacology 109 (2007) 417–427 /
DOI: 10.1016/j.jep.2006.08.011
(3)
Study on the Bioactive Constitutents from Harrisonia Perforata / Chinese Pharmacology, 2011-04-27 07:16
(4)
Chemical constituents from fruits of Harrisonia perforata / Xiao-Hui Yan, Ying-Tong Di, Xin Fang et al / Phytochemistry, Vol 72, No 6, April 2011, Pages 508-513 / doi:10.1016/j.phytochem.2011.01.010
(5)
In vitro antimicrobial activity of plants used in Cambodian traditional medicine / Chea A, Jonville MC, Bun SS, Laget M, Elias R, Duménil G, Balansard G. / Am J Chin Med. 2007;35(5):867-73.
(6)
Inhibitory effect of some herbal extracts on adherence of Streptococcus mutans / Limsong, J., Benjavongkulchai, E., Kuvatanasuchati / J. Journal of ethnopharmacology. (2004)
(7)
Harrisonia perforata (Blanco) Merr. (accepted name) / Chinese names / Catalogue of Life, China
(8)
Harrisonia perforata (Blanco) Merr / Vernacular names / GLOBinMED

(9)
In vivo and in vitro anti-inflammatory activity of Harrisonia perforata root extract / Pattama Somsil, Nijsiri Ruangrungsi, Wacharee Limpanasitikul, Chandhanee Itthipanichpong / Pharmacognosy Journal 11/2012; 4(32):38–44. DOI: 10.5530/pj.2012.32.8
(10)
Inhibitory Effect on β-Hexosaminidase Release from RBL-2H3 Cells of Extracts and Some Pure Constituents of Benchalokawichian, a Thai Herbal Remedy, Used for Allergic Disorders / Thana Juckmeta, Pakakrong Thongdeeying, and Arunporn Itharat / Evidence-Based Complementary and Alternative Medicine, Volume 2014 (2014) / http://dx.doi.org/10.1155/2014/828760
(11)
Liposoluble Components and Their Antioxidant Activities from Harrisonia perforata
/ WANG Jiangrong, WANG Maoyuan, LIANG Zhengfen, YAN Xiaoxia, WANG Zhunian / Chinese Journal of Tropical Agriculture, 2011-09
(12)
Rearranged limonoids and chromones from Harrisonia perforata and their anti-inflammatory activity. / Choodej S, Sommit D, Pudhom K / Bioorganic & medicinal chemistry letters. 23(13): 3896-900 / DOI: S0960-894X(13)00545-3
(13)
A Novel Iodomethylene-dimethyl-dihydropyranone Induces G2/M Arrest and Apoptosis in Human Cancer Cells / JÉRÔME BIGNON, MICHEL BÉNÉCHIE, DENYSE HERLEM, JIAN-MIAO LIU, ALEXIA PINAULT, FRANÇOISE KHUONG-HUU and JOANNA WDZIECZAK-BAKALA / Copyright© 2009 International Institute of Anticancer Research
(14)
In vitro antimicrobial activity of plants used in Cambodian traditional medicine. / Aun Chea, Marie-Caroline Jonville, Sok-Siya Bun, Michèle Laget, Riad Elias, Gérard Duménil, Guy Balansard / Am J Chin Med 2007 ;35(5):867-73
(15)
Antimicrobial activity of the extracts from Benchalokawichian remedy and its components. / Nuaeissara S, Kondo S, Itharat A. / J Med Assoc Thai. 2011 Dec;94 Suppl 7:S172-7.
(16)
ANTIPYRETIC AND ANTINOCICEPTIVE EFFECTS OF BEN-CHA-LO-KA- WI-CHIAN REMEDY / Anusara Jongchanapong, Chatubhong Singharachai, Chanida Palanuvej, Nijsiri Ruangrungsi and Pasarapa Towiwat* / 9th NRCT-JSPS Joint Seminar on Natural Medicine in Pharmaceutical Sciences
(17)
Acute and subchronic toxicity study of the water extract from Harrisonia perforata Merr. in rats / Seewaboon Sireeratawong; Nirush Lertprasertsuke; Umarat Srisawat; Amornat Thuppia; Anongnad Ngamjariyawat; Nadthaganya Suwanlikhid; Kanjana Jaijoy / Songklanakarin Journal of Science and Technology 2009
(18)
Harrisonia perforata / Synonyms / The Plant List
(19)
Study on the chemical constituents in the fruit of Harrisonia perforata. / Xiao Xia Yan, Zheng Fen Liang, Mao-Yuan Wang, Zhu Nian Wang / Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 36(2): 223-5, February 2013
(20)
A CLINICAL STUDY PHASE I ON SAFETY OF THAI MEDICINAL FORMULA “BENJALOKAWICHIEN (HA-RAK)” AND EACH PLANT COMPONENT EXTRACT. / Warumpa Suwannarat, Mali Achariyakul, Arunporn Itharat, Somboon Kiettinun / Thammasat Medical Journal, Vol 12, No 4 (2012)
(21)
Inhibitory effect of Harrisonia perforata root extract on macrophage activation
/ Pattama Somsill*, Chandhanee Itthipanichpong, Nijsiri Ruangrungsi, Wacharee Limpanasithikul / 168 Thai J Pharmacol Vol. 32, No.1, 2010
(22)
Cytotoxicity Effects of Lipophilic Extracts of Thai Herbs in Human Breast Cancer and Human Epidermoid Carcinoma Cells / Yuwadee Yusuk, Jariyanart Gaywee / Proceedings of the 6th IEEE International Conference on Nano/Molecular Medicine and Engineering, Nov 4-7, 2012, Bangkok, Thailand.
(23)
Unprecedented Quassinoids with Promising Biological Activity from Harrisonia perforata / Xin Fang, Ying Tong Di, Yu Zhang, Zhi Ping Xu, Yang Lu, Qian Qian Chen, Qi Tai Zheng, Xiao Jiang Hao / Internationale Ausgabe / DOI: 10.1002/anie.201412126
(24)
A Novel Iodomethylene-dimethyl-dihydropyranone Induces G2/M Arrest and Apoptosis in Human Cancer Cells / JÉRÔME BIGNON, MICHEL BÉNÉCHIE, DENYSE HERLEM, JIAN-MIAO LIU, ALEXIA PINAULT, FRANÇOISE KHUONG-HUU and JOANNA WDZIECZAK-BAKALA / ANTICANCER RESEARCH 29: 1963-1970 (2009)


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