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Family Meliaceae
Piyagaw
Xylocarpus granatum J.Koenig

PUZZLENUT TREE
Hai you

Scientific names  Common names 
Amoora salomoniensis C.DC. Bigi (Tagb.) 
Carapa granatum (J.Koenig) Alston Kolimbaning (Ilk.) 
Carapa obovata Blume Lubanayong (Ibn.) 
Granatum obovatum (Blume) Kuntze Migi (Pamp.) 
Xylocarpus granatum Koenig Nige (Tagb., Bik., Tag.) 
Xylocarpus obovatus (Blume) A.Juss. Nigi (Tagb.) 
  Piadak (Tagb.) 
  Piagau (Tag., P. Bis., Sul.) 
  Piyagaw (Tag.) 
  Pulit (Yak.) 
  Tabigi (Tag., Bik., P. Bis., S. L. Bis., C. Bis.) 
  Tibigi (Tag., Bik.) 
  Tambo-tambo (Sub., Mag., Sul.) 
  Tambu-tambu (Mag.) 
  Puzzle fruit tree (Engl.)
  Puzzlenut tree (Engl.)
  Cannonball mangrove (Engl.)
Xylocarpus granatum J.Koenig is an accepted name The Plant List

Other vernacular names
BENGALI: Dhundal, Dhundul, Tutul, Karamphul, Karambola, Karamfola.
CHINESE: Hai you, Mu guo lian.
TAMIL: Somuntheri, kadal manga.
TELUGU: Chenuga.
SINGHALESE: Kontalai, mutti kad.

Botany
Piyagaw is a small tree growing 3 to 12 meters high. Leaves are abruptly pinnate, with pairs of leaflets which are elliptic or obovate, 8 to 18 centimeters long, 4 to 8 centimeters wide, with a pointed base and rounded tip. Flowers are small and white, 4-parted, borne on short terminal or axillary (upper) panicles. Fruit is spherical, 9 to 12 centimeters in diameter, with 6 to 12 seeds. Pericarp is hard and fibrous, splitting into 4 valves. Seeds are angled, with a spongy integument.

X. moluccensis is similar to Xylocarpus granatum (piyagaw). X. granatum has larger fruit, smooth, patchy bark, buttresses and plant-like aerial roots. X. moluccensis has a smaller fruit, with conical pneumatophores. (1)

Distribution
- Throughout the Philippines in mangrove swamps, bordering tidal streams.
- Also occurs in India and Ceylon through Malaya and New Caledonia.


Constituents
- Solid fat, 40-60%; tannin.
- The seeds, fruits and stems yield a large number of limonoids.

- Phytochemical exam of fruits of X. granatum isolated five new protolimonoids, protoxylocarpins A-E, and two new limonoids, xylocarpins J and K, together with xyloccensis M and Y. (8)
- Seeds yielded 13 compounds: a new one, indiangranatumin A, together with known compounds swietemahonolide, febrifugin ,khayasin T, febrifugin A , gedunin, isolariciresinol, phaseic acid, aromadendrin, 4-hydroxy cinnamic acid, 4-hydroxybenzoic acid, 4-hydroxyphenylacetic acid,and xylogranatinin. (9)
- Seed kernels yielded three new phragmalin limonoids, moluccensins H-J.
- Methanolic extract yielded carbohydrates, saponins, tannins, and flavonoids. Alkaloids and glycosides were not found in the extract.
- Study of seed yielded a new glyceride, 1,3-di-(16'-acetoxy-palmitoyl)-glycerol ( 1), and a known ceramide, (2 S,3 S,4 R,8 E)-2-[(2' R)-hydroxypalmitoylamino]-8-tetracosene-1,3,4-triol ( 2). (18)
- Study of stem bark yielded a new flavonol derivative dihydrocaffeic acid-(3→8)-epicatechin together with two known derivatives, (+)-catechin and catechin-(4β→8)-catechin. (see study below) (19)
- Study for chemical constituents of fruit yielded ten compounds identified as: spicatin (1), xyloccensin K(2), 6-acetoxycedrodorin (3), aurantiamide acetate (4), (+)-catechin (5), alpha-tocopherol (6), abscisic acid (7), daucosterol (8), 4-hydroxybenzoic acid (9) and ethyl 3,4-dihydroxybenzoate (10). (20)
- Phytochemical screening yielded major constituents viz., alkaloids, steroids, tannins, triterpenes, limonoids, flavonoids, saponins. Various compounds isolated with known biologic activities were: 4-hydroxybenzoic acid, ethyl 3,4- dihydroxybenzoate, xylogranatinin, granatoin, N-Methyl indersine, β-Sitosterol, β -Sitosterol β -D-glucoside, Methyl angolensate, Gedunin and 1α-hydroxy-1,2-dihydrogedu., xyloccensin O, xyloccensin P , xyloccensin Q, Catechin, epicatechin, procyanidins of the B, trimer and pentamer xyloccensins O-P, xyloccensins Q-V, Xyloccensin L, xyloccensin K, xyloccensin IJ. Chelerythrine and dihydrochelerythrine. (22)
- Fruit yielded two new mexicanolides: 3-deacetyl xyloccensin M and 3-deacetyl xyloccensin N. (25)
- Study of twigs and leaves isolated eight new tetratriterpenoids viz., 9-epixylogranatin A (1), Xylogranatumin A (2), 6-O-acetyl xylocarpin D (3), 14-Hydroxy-14,15-dihydrogranatumin C (4), 30-O-tigloylhainangranatumin J (5), 9-O-methyl xylogranatin R (6), 30-O-acetylhainangranatumin E (7), 1,2-Dihydro-3α-hydroxy-turranolide (8), together with four related known compounds (9-12). (see study below) (26)
- Study of fruits for fatty acids yielded eleven kinds of fatty acids, 5 were unsaturated, total amount was 81.97%, with the highest content composed of 9,12,15-octadecatrienoic acid. (29)

Properties
- Bitter, astringent, anti-diarrhetic.
- Bark and root considered astringent.
- Studies have shown antimicrobial, antioxidant, cytotoxic, antimalarial, antidiarrheal, antihyperglycemic, hypolipidemic, cardiotonic, tyrosinase inhibitory, antifilarial, antitumor, neuroprotective properties.


Parts used
Fruits, bark, leaves, seeds.

Uses
Folkloric
- Fruits or seeds , powdered or decoction, are used for diarrhea.
- In Tonga, the bark is used for candidiasis, scabies, baby rash, stomach pains, constipation.
- In Malaya, used for cholera, colic diarrhea, and other abdominal affections.
- In Fiji, bark used for headaches, fatigue, candidiasis (leaves and bark), joint pains, chest pains and buccal pains.
- In East India and Sri Lanka, seed paste used for breast tumors. Roots used as remedy for cholera and dysentery. (15)
- Also used for replapsing sickness.
- In Bangladesh, used for gastrointestinal disturbances such as cholera, dysentery, diarrhea; also for fever.

Others
- Wood: Used for boat building, furniture, and a fuel bark.
- Tanning: Bark used for tanning.
- Illuminant: Seed oil used for illumination

Studies
Antimicrobial:
Study of crude extract of X. granatum showed significant antimicrobial activity against S epidermis, S aureus, Shigella boydii and Proteus spp and moderate activity against E coli and S pyogenes. (1)
Antioxidant / Flavonols:
Methanol extract showed to be rich in flavan-3-ols and procyanidins. It exhibited excellent DPPH radical scavenging and 15-lipoxygenase inhibiting activities attributed to the high content of catechins and procyanidins.
Phragmalins:
Study isolated three new polyhydroxylated phragmalins, named xyloccensins Y, Z1 and Z2 from the fruit of Xylocarpus granatum, with eight known compounds. (5)
Antidiarrheal / Bark:
Study of methanol extract of XG bark for in experimental diarrhea induced by castor oil and magnesium sulfate in mice showed significant dose-dependent antidiarrheal activity and supports its use in traditional herbal medicine. (6)
Antibacterial:
Study of methanol extract demonstrated antibacterial activity against gram positive bacteria Staphylococcus aureus and Bacillus subtilis and gram negative bacteria Proteus vulgaris. (12)
Antibacterial / Bark:
Antimicrobial screening showed the crude ethanol extract and partial fraction of barks showed significant antimicrobial activity against Staphylococcus epidermis, S. aureus, Shigella boydii and Proteus spp. and moderate activity against E. coli, Streptococcus pyogenes. (13)
Antimalarial / Gedunin and Xyloccensin-I:
Study evaluated the antimalarial activity of Xylocarpus granatum fruits and their active constituents. A chloroform fraction showed promising anti-malarial activity in an in vitro model of Plasmodium falcifarum. Gedunin and xyloccensin-I, pure compounds isolated from the active fraction, showed activity equivalent to the parent active fraction in vitro model. (14)
Antidiarrheal / Antimicrobial / Bark and Leaves:
An ethanolic extract of bark and leaf showed antidiarrheal activity in castor oil induced diarrheal rats in a dose-dependent manner. The bark extract showed gram positive antibacterial activity and anti-yeast activity. (15)
Cardiotonic / Bark:
Study evaluated the cardiotonic activity of an alcoholic bark extract of Xylocarpus granatum. Extract showed dose dependent positive ionotropic effect on normal and hypodynamic frog heart. There was also dose dependent inhibition of Na, K ATPase activity. The cardiotonic activity is similar to the mechanism of digoxin (inhibition of Na, K ATPase enzyme activity). (16)
Antihyperglycemic/ Antidyslipidemic / Fruits:
Study of ethyl acetate fraction of fruits of X. granatum and X. moluccensis showed both are effective in improving glucose tolerance, decreasing blood glucose, serum cholesterol and triglycerides in STZ-induced diabetic rats and dyslipidemic hamsters. There was also increase glucose uptake by L6 skeletal muscle cells. (17)
Antioxidant / Flavanol / Stem Bark:
Study of stem bark yielded a new flavanol derivative dihydrocaffeic acid-(3→8)-epicatechin together with two known derivatives, (+)-catechin and catechin-(4β→8)-catechin were isolated from the stem bark. Catechin-(4β→8)-catechin showed the highest DPPH radical scavenging activity with IC50 of 4.5 µg/mL. (19)
Tyrosinase Inhibitory and Antioxidant Activity / Seed Kernel:
Study evaluated various extracts of seed kermel for tyrosinase inhibitory activity. A methanol extract showed best activity on inhibition of monophenolase and diphenolase activity. The extract also showed antioxidant activity with IC50 of 10.61 ± 2.1µg/mL. Results showed the seed kernel has potential as tyrosinase inhibitor and antioxidant agent. (
21)
Antifilarial / Genudin and Photogedunin:
Study in experimental rodent host evaluating the antifilarial activity of X. granatum showed the fruit extract contains promising in vitro and in vivo antifilarial activity against human lymphatic filarial parasite B. malayi. Results showed antifilarial activity primarily localized in the ethyl acetate soluble fraction with IC50 of 8.5 and 6.9 µg/ml in adult worms and microfilaria, respectively. The activity was attributed to two pure compounds gedunin and photogedunin. (
23)
Xylocarpin H / Limonoid / Antidepressant:
Study of Xylocarpin H, a limonoids from X. granatum, showed antidepressant-like effects in mouse forced swimming and tail suspension tests. The antidepressant activity in mouse behavioral models of depression was likely through inhibition of HPA axis systems. Results suggest a potential as novel antidepressant candidate for treatment of depression and related disorders. (
24)
Tetratriterpenoids / Neuroprotectice:
Study of twigs and leaves isolated eight new tetratriterpenoids (1-8), together with four related known compounds (9-12). Compounds 11 and 12 displayed moderate effects against h2)2-induced neurotoxicity in PC12 cells. (see constituents above) (
26)
Xylogranatins / Antifeedants / Seeds:
Study of seeds yielded 13 limonoids, xylogranatins F-R (1-13). The structure of the compounds suggest a new biogenetic pathway to tetranortriterpenoids. Xylogranatins F, G, and R exhibited marked antifeedant activity against the third larvae of Mythimma separata. The most potent was xylogranatin G. (
27)
Xylogranin B / Wnt Signal Inhibitory Limonoid / Cytotoxicity / Seeds:
Study isolated xylogranin B (compound 2) from X. granatum leaves. Compound 2 inhibited TCF/ß-catenin transcriptional activity (IC50 48.9 nµ) and exhibited strong cytotoxicity against colon cancer cell lines. Compound 2 significantly decreased ß-catenin levels in nuclei which in Wnt signal inhibitory effects. (
28)

Availability
Wild-crafted.

Godofredo U. Stuart Jr., M.D.

Last Update October 2016

IMAGE SOURCES: Public Domain (1) Minor Products of Philippine Forests / Vol 1 / Philippine Mangrove Swamps / William Brown and Arthur Fisher / Plate XII / Xylocarpus moluccensis / 1920
OTHER IMAGE SOURCES: File:Xylocarpus granatum.jpg / Cannonball mangrove (Xylocarpus granatum) / Toby Hudson / 18 July 2010 / Creative Commons / Wikipedia

Additional Sources and Suggested Readings
(1)
ANTIBACTERIAL ACTIVITY OF THE CRUDE ETHANOLIC EXTRACT OF XYLOCARPUS GRANATUM STEM BARKS / M A Alam et al / Bangl. J. Vet. Med. (2006). 4 (1): 69–72
(
2)
NATURAL AND ANTHROPOGENIC BIOGEOGRAPHY OF MANGROVES IN THE SOUTHWEST PACIFIC

(
3)
Chemical and biological studies of medicinal plants from the Sundarbans mangrove forest / Wangensteen H et al / Advances in Phytotherapy Research, 2009: 59-78
(
4)
Cytotoxic Effects of Bangladeshi Medicinal Plant Extracts / Uddin S J et al / Evid Based Complement Alternat Med. 2009 Aug 25
(5)
Polyhydroxylated Phragmalins from the Fruit of a Chinese Mangrove, Xylocarpus granatum / Yuan Zhou, Fan Cheng, Jun Wu and Kun Zou / J. Nat. Prod., 2006, 69 (7), pp 1083–1085 / DOI: 10.1021/np050545c

(6)
Assessment of antidiarrhoeal activity of the methanol extract of Xylocarpus granatum bark in mice model / Razina Rouf, Shaikh Jamal Uddin, Jamil Ahmad Shilpi, Mahiuddin Alamgir / Journal of Ethnopharmacology
Vol 109, Issue 3, 12 February 2007, Pages 539-542 / doi:10.1016/j.jep.2006.08.015
(7)
In Vitro Cytotoxicity Screening of Xylocarpus Sp. Crude Extracts Against Human Hepatocellular Carcinoma Cell Line (HepG2) / A S Nur Khairina, A F A Fuad et al / UMTAS 2011
(8)
Protolimonoids and Limonoids from the Chinese Mangrove Plant Xylocarpus granatum / Jianxin Cui, Zhiwei Deng, Minjuan Xu et al / Helvetica Chimica Acta, Volume 92, Issue 1, pages 139–150, January 2009 / DOI: 10.1002/hlca.200800177
(9)
Chemical constituents in seeds of Indian mangrove Xylocarpus granatum / Yang Xiao-bo, Yang Shen-xin et al /
DOI: CNKI:SUN:ZCYO.0.2010-06-004
(10)
Xylocarpus granatum K. D. Koenig (accepted name) / Chinese names / Catalogue of Life, China
(11)
Xylocarpus granatum J. König - MELIACEAE - Dicotyledon / Checklist of Mangrove species of South East India and Sri Lanka
(12)
PHYTOCHEMICAL SCREENING, PLANT GROWTH INHIBITION, AND ANTIMICROBIAL ACTIVITY STUDIES OF XYLOCARPUS GRANATUM / A F M SHAHID-UD-DAULA AND MOHAMMAD ANWARUL BASHER* / Malaysian Journal Pharmaceutical Sciences, Vo. 7, No. 1, 9–21 (2009)
(13)
ANTIBACTERIAL ACTIVITY OF THE CRUDE ETHANOLIC EXTRACT OF XYLOCARPUS GRANATUM STEM BARKS / M. A. Alam*, M. Sarder, M. A. Awal, M. M. H. Sikder and K. A. Daulla / Bangl. J. Vet. Med. (2006). 4 (1): 69–72
(14)
Antimalarial activity in Xylocarpus granatum (Koen) / Vijai Lakshmi*, Shishir Srivastava, Sunil Kumar Mishra, Mahendra Nath Srivastava, Kumkum Srivastava & Sunil Kumar Puri /  Natural Product Research, Volume 26, Issue 11, 2012 / DOI:10.1080/14786419.2010.535000
(15)
Antidiarrheal and Antimicrobial Activities of Bark and Leaf Extracts of Xylocarpus granatum Koenig / P. Rajeswara Rao , Y. Trilochana , K. K. Chaitanya / Journal of Natural Remedies, Vol 3, Issue 2, June 2003
(16)
Cardiotonic Activity of Alcoholic Bark Extract of Xylocarpus Granatum with Emphasis on Its Mechanism of Action / Y. Trilochana, P. Sowjanya, G.P.V. Sangeetha, P. Rajeswara Rao, Prof. P. Rajeswara Rao / Iosr Journal Of Pharmacy, Volume 3, Issue 1 (February 2013), Pp 04-09
(17)
ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC ACTIVITY IN ETHYL ACETATE FRACTION OF THE FRUITS OF XYLOCARPUS GRANATUM AND XYLOCARPUS MOLUCCENSIS / Swayam Prakash Srivastava, Neha Rahuja, Savita Srivastava, Akhilesh Kumar Tamrakar, Sunil Kumar Mishra, Shishir Srivastava, Vijai Lakshmi, Mahendra Nath Srivastava, Arvind Kumar Srivastava / International Journal of Pharmacy and Pharmaceutical Sciences, Vol 7, Issue 2, 2015
(18)
A new glyceride from the seeds of Xylocarpus granatum / Huo, Changhong; Zhang, Qing; Wu, Yibing; Ge, Ying; Wang, Yufang; Zhang, Manli; Li, Ligeng; Shi, Qingwen / Chemistry of Natural Compounds; Jan 2013, Vol. 48, Issue 6, p 934
(19)
Flavanol derivatives with antioxidant activity from the stem bark of Xylocarpus granatum
/ Musa CHACHA / Int. J. Biol. Chem. Sci. 4(2): 371-376, April 2010
(20)
Studies on the chemical constituents of the fruit of Xylocarpus granatum / Cheng F, Zhou Y, Zou K, Wu J. / Zhong Yao Cai. 2009 Aug;32(8):1220-3.
(21)
The Study of Tyrosinase and Antioxidant Activity of Xylocarpus Granatum Koenig Seed Kernel Extract toward Evidence Based Indigenous Knowledge from Togean Archipelago, Indonesia / Zamani NP*, Gazali M and Batubara I / J Marine Sci Res Dev 5:168. doi:10.4172/2155-9910.1000168
(22)
Ethnomedicinal, Antimicrobial and Antidiarrhoeal Studies on the Mangrove Plants of the Genus Xylocarpus: A Mini Review / Swagat Kumar Das, Dibyajyoti Samantaray and Hrudayanath Thatoi* / J Bioanal Biomed 2014 / http://dx.doi.org/10.4172/1948-593X.S12-004
(23)
Gedunin and photogedunin of Xylocarpus granatum possess antifilarial activity against human lymphatic filarial parasite Brugia malayi in experimental rodent host / Sweta MisraMeenakshi Verma, Sunil Kumar Mishra, Shishir Srivastava, Vijai Lakshmi, Shailja Misra-Bhattacharya / Parasitol Res (2011) 109: 1351. / doi:10.1007/s00436-011-2380-x
(24)
Xylocarpin H, a Limonoid of Xylocarpus granatum, Produces Antidepressant-Like Activities in Mice / Xi Yin*, Xin Li*, Yaoguang Hao*, Yiwen Zhao, Jinghong Zhou, Haishui Shi / Journal of Behavioral and Brain Science, 2015, 5, 524-532 / DOI: http://dx.doi.org/10.4236/jbbs.2015.511050
(25)
Two New Mexicanolides from the Fruit of the Chinese Mangrove Xylocarpus granatum / Jun Wu/ Si Zhang, Yang Song, Zhihui Xiao, Qiang Xiao, Qingxin Li / Zeitschrift für Naturforschung B, A Journal of Chemical Sciences, Volume 60, Issue 12 (Dec 2005)
(26)
Novel and Neuroprotective Tetranortriterpenoids from Chinese Mangrove Xylocarpus granatum Koenig
/
Zhen-Fang Zhou, Tibor Kurtán, Attila Mándi, Yu-Cheng Gu, Li-Gong Yao, Guo-Rong Xin, Xu-Wen Li & Yue-Wei Guo / Scientific Reports 6, Article number: 33908 (2016) / doi:10.1038/srep33908
(27)
Xylogranatins F–R: Antifeedants from the Chinese Mangrove, Xylocarpus granatum, A New Biogenetic Pathway to Tetranortriterpenoids / Jun Wu Dr., Si Zhang Prof., Torsten Bruhn Dr., Qiang Xiao Dr., Haixin Ding, Gerhard Bringmann Prof. Dr. / Chemisty: A European Journal / DOI: 10.1002/chem.200700663
(28)
Xylogranin B: A Potent Wnt Signal Inhibitory Limonoid from Xylocarpus granatum / Kazufumi Toume, Kentaro Kamiya, Midori A. Arai, Naomi Mori, Samir K. Sadhu, Firoj Ahmed, and Masami Ishibashi* / Org. Lett., 2013, 15 (23), pp 6106–6109 / DOI: 10.1021/ol4029995
(29)
Analysis of Fatty Acid of Fruits of Xylocarpus granatum with GC-MS / XU Hui-wang,WU Jun,CHENG Fan, ZOU Kun, ZHOU Yuan / Chinese Journal of Experimental Traditional Medical Formulae, 2013-07 /

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