The Pharmacological Properties of Terpenoids from Sandoricum Koetjape

Article ID: WMC001311 2046-1690

The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape

Corresponding Author: Dr. Amin Malik Shah Abdul Majid, Lecturer in Universiti Sains Malaysia , Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, , Minden 11800, Pulau Penang, Malaysia, 11800 - Malaysia

Submitting Author: Mr. Zeyad D Nassar, Master Student , Department of Pharmacology , School of Pharmacy , University Sains Malaysia , School of Pharmaceutical Sciences, USM , 11800 - Malaysia

Article ID: WMC001311 Article Type: Review articles Submitted on:09-Dec-2010, 06:33:14 PM GMT Published on: 10-Dec-2010, 07:35:24 PM GMT Article URL: http://www.webmedcentral.com/article_view/1311 Subject Categories:COMPLEMENTARY MEDICINE Keywords:Terpenoids, Koetjapic acid, Sandoricum koetjape, Natural compounds, complementary medicine How to cite the article:Nassar Z , Aisha A , Abdul Majid A . The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape . WebmedCentral COMPLEMENTARY MEDICINE 2010;1(12):WMC001311 Source(s) of Funding: This work was financially supported by Universiti Sains Malaysia (USM) Research University Grant [Grant 1001/PFARMASI/81144]

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The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape

Author(s): Nassar Z , Aisha A , Abdul Majid A

Abstract purified from the opium .Following the isolation of salicylic acid from the bark of the willow tree, Hoffmann synthesized aspirin in 1897. Ephedrine was isolated from the Chinese herb mahuang (Ephedra) in Sandoricum koetjape is a traditional plant belonging to 1887. The antimalarial drug artemisinin was developed the family of Meliaceae. It is native to Southeast Asian in 1972 from the Chinese herb qinghao (sweet countries, including Malaysia and Philippines. In wormwood, Artemisia annua L.) [3]. Malaysia, it is locally known as Santol. The tree is a Although, humans depend on plants from thousands medium-sized with edible fruit. In Malaysia, the years, the science of medicinal plants is still a vastly aqueous extract of the bark is traditionally consumed unknown. Scholars estimate that 5 % of 250000 as a tonic after giving birth. Number of comprehensive species of plants have been investigated [2]. This fact studies on its phytochemical and pharmacological points in the importance of screen new plants for their properties has been reported. Various bioactive pharmacological properties. compounds have been isolated from fruits, seeds, Natural products and cancer treatment: leaves and bark. More than 10 terpenoids have been Some secondary metabolites of the plants such as isolated and studied for their potential medicinal alkaloids, terpenoids and glycosides serve either as properties. Terpenoids represent the largest class of protective agents against various pathogens (e.g. secondary metabolites from the natural source. This insects, fungi or bacteria) or growth regulatory article aims to review the pharmacological properties molecules (e.g. hormone-like substances), as a result, of the isolated terpenoids from Sandoricum koetjape. secondary metabolites can serve as potential anticancer drugs, either by direct cytotoxic activity against cancer cells or by modulating the tumor Review development process [4]. In fact, natural products are considered as a mainstay in cancer treatment, as 60% of worldwide anticancer drugs between 1983 and 1994 Influence of medicinal plants on diseases were from natural origin [5]. treatment: The most famous examples are vinblastine and Plants have formed the basis of sophisticated vincristine from Catharanthus roseus, paclitaxel from traditional medicine systems that have been in Taxus brevifolia Nutt, etoposide and teniposide which existence for thousands of years [1]. Plants have been are epimers of podophyllotoxin which isolated from utilized to heal ailments from alleviating headache to roots of various species of the genus podophyllum, treating heart diseases [2]. and camptothecin which isolated from the Chinese The first illustrated book about gathering, preparation tree Camptotheca acuminata [6]. The impact of these and use of medicinal plants was written by Chinese products in cancer treatment is very obvious, Emperor Shen Nung before 3000 thousand years [1]. paclitaxel and camptothecin were estimated to The Greeks also contributed in the development of the account for nearly one-third of the global anticancer herbal drugs. “De Materia Medica” written by market or about $3 billion of $9 billion in total annually Dioscorides, the Greek physician (100 A.D.), in 2002 [7]. described more than 600 medicinal plants [2]. The Terpenoids: expertises of Greeks in herbal medicine were Terpenoids are defined as secondary metabolites with preserved only by Arabs, during the dark and middle molecular structures containing carbon backbones Ages. Arabs developed this science using their own made up of isoprene (2-methylbuta- 1, 3-diene) units. resources and together with Greco-Roman, Chinese Isoprene contains five carbon atoms and as a result, and Indian herbs [1]. the number of carbon atoms in any terpenoids is a The shift from using ordinary herbal medicines to multiple of five. The terpenoids consists of two modern pharmaceuticals was just started in 1800s. isoprene units, i.e. ten carbon atoms. The This transfer was due starting isolation of pure classification of terpenoids based on the number of compounds from plants. In 1805, morphine was isoprene units [8] (Table 1).

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More than 36000 terpenoids compounds have been decoction prepared from the bark of the plant [16]. identified, making terpenoids the largest class of plant Phytochemistry and pharmacological activities of S. metabolites. Most of the thousands of terpenoids koetjape: produced by plants have no discernible role in growth The seeds, leaves, fruits and the stem bark of S. and development and are, therefore, often classified koetjape have been rigorously studied for the chemical as ‘secondary’ metabolites. Although comparatively constituents. Various S. koetjape’s extracts and many few of these substances have been investigated in isolated chemicals showed potential pharmacological depth, they are thought to serve primarily in ecological activities. roles, providing defence against and acting as Andirobin-type limonoids have been isolated from S. attractants for animals that disperse pollen or seeds or koetjape’s seeds, namely sandoricin and as inhibitors of germination and growth of 6-hydroxysandoricin. These limonoids showed neighbouring plants [9-11] remarkable anti-feedant activities [17]. The terpenoids group show significant Bryononic acid and bryonolic acid terpenoids and pharmacological activities, such as anti-viral, meso-inositol and dimethyl mucate polyalcohol have anti-bacterial, anti-malarial, anti-inflammatory, been isolated from the S. koetjape’s fruits hulls [18] inhibition of cholesterol synthesis and anti-cancer The leaves have been yielded trijugin limonoids activities [12]. namely Sandrapins A, B, C, D and E, and sandoripin A Sandoricum koetjape: and B [19]. S. koetjape is traditional medicinal plant belonging to Several comprehensive studies have been carried out the family Meliaceae, it is native to Malaysia, on the stem bark. A number of triterpenoids have been Cambodia and Southern Laos. It has been introduced isolated from the stem bark such as, katonic acid, into the Philippines, India, Indonesia, and Andaman indicic acid [20], koetjapic acid, Islands since long time ago. A few samples were 3-oxo-12-oleanen-29-oic acid, alloaromadendrene, introduced into North and South America such as caryophyllene oxide, spathulenol [21], bryononic acid, Honduras and Costa Rica, and Miami and Florida in secobryononic acid, secoisobryononic acid [22], USA [13]. 20-epikoetjapic acid, 3-epikatonic acid and sandorinic S .koetjape is an evergreen tree grows 15-45 m tall in acid A, B and C [23]. Figure 1.3 shows chemical fast manner, as the plant gets older the trunk get structure of some terpenoids extracted from the bark. buttressed and branched close to the ground. Younger Many pharmacological properties have been branches have dense brown hair. The 3 leaflets leaves investigated for the majority of the isolated terpenoids. are compound, elliptic to oblong-ovate, 20-25 cm long, The cytotoxic properties of Koetjapic acid, Katonic acid blunt at the base and pointed at the apex. The flowers and 3-oxo-12-oleanen-29-oic acid were investigated are 1 cm long consist of 5 petals stalked panicles against ten cancer cell lines. Katonic acid and 15-30 cm in length, and have green, yellow, or 3-oxo-12-oleanen-29-oic were cytotoxic against many pinkish-yellow colour Plate 1.1 shows picture of leaves of cancer cell lines (i.e. IC50 < 20 µg/ml), they were , seeds and fruits of S. koetjape . very potent against murine lymphocytic leukaemia There are two types of S. koetjape fruit, viz, red or P-388 cell line (IC50 = 0.11 and 0.61 µg/ml yellow. The rind of the former type is sour, have respectively). In contrast, koetjapic acid was inactive thicker rind and the amount of pulp is less. While the against all of tested cancer cell lines [21]. yellow fruits are sweet, have thin rind and a thicker Although koetjapic acid has not been reported as a pulp. However, nowadays only the yellow variety is cytotoxic compound till now, it showed notable DNA available in Malaysia [13,14]. polymerase inhibition activity [24]. Ismail et al., In Malaysia, S. koetjape is known as sentieh, sentol, reporetd ichthyotoxic properties of koetjapic acid and setol, sentul, setul, setui, kechapi or ketapi. The 3-oxo-12-oleanen-29-oic acid [25]. However, katonic traditional Indonesian names are ketjapi or sentool. acid has not exhibited significant ichthyotoxic activity. While in Thailand it is called saton, satawn, katon, or In the same study, the all three terpenoids was ka-thon [13,14]. considered as anti-tumor promoting agents as they The classification of S. koetjape is demonstrated in show significant inhibiory effect on induced- table 2. Epstin-Barr virus early antigen activation. Koetjapic Traditional medicinal uses of S. koetjape: acid was the most potent agents among the three In Malaysia, the aqueous extract of the bark is terpenoids in the lastest two mentioned assays traditionally consumed as a tonic after giving birth [15], (Ichthyotoxicity and anti-tumor promoion studies). while in Indonesia it is used by folk medical Koetjapic acid also appears to be a promising cancer practitioners to treat leucorrhoea and colic with the chemoprevintive compound, as it remarkably delayed

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tumor promotion in two stage mouse carcinogenesis 27, 297-309. induced by 7,12 dimethylbenz(a)anthracin and 4. Kintzios, S.E. (2003) what do we know about cancer prompoted by 12-O-tetradecanoylphorbol 13-acetate and its therapy ? In Kintzios, S.E. and Barberaki, M.G. (TBA) [25]. (eds.), plants that fight cancer CRC press pp. 1-14. In TBA-induced mouse ear odema assay to explore 5. Cragg, G.M., Newman, D.J. and Snader, K.M. the anti- inflammatory properties, methanolic extract, (1997) Natural Products in Drug Discovery and oxo-12-oleanen-29-oic acid, Katonic acid and Development. Journal of Natural Products, 60, 52-60. Koetjapic acid inhibits inflammation by 94 % 94 %, 81 6. Newman, D.J., Cragg, G.M. and Snader, K.M. % and 13 % respectively [26]. Koetjapic acid also (2000) The influence of natural products upon drug inhibited the growth of Staphylococcus aureus, discovery. Nat Prod Rep, 17, 215-34. methicillin-resistant S. aureus and Pseudomonas 7. Oberlies, N.H. and Kroll, D.J. (2004) Camptothecin aeruginosa, with MIC range of 3.125-6.25 µg/ml [27]. and Taxol:â€‰ Historic Achievements in Natural Recently, hexan extract of S.koetjape shows Products Researchâ?¥. Journal of Natural Products, noteworthy anti-angiogenic 67, 129-135. activity in a study depended on ex-vivo rat aortic ring 8. Ashour, M., Wink , M. and J., G. (2010) assay. Hexan extract also shows selective cytotoxicity Biochemistry of terpenoids : monoterpenes , against colorectal carcinoma HCT 116 cell line. The sesquiterpenes and diterpenes In Wink, M. (ed.), apoptotic propoties of S.koetjape hexan extarct have Biochemistry of Plant Secondary Metabolism. John been confirmed on two cancer cell lines, MCF-7 and Wiley & Sons, vol. 40. HCT 116 [28,29]. 9. Wink, M. (ed.) (2010) Function and Biotechnology of Koetjapic acid which is the main compound in S. Plant Secondary Metabolites. Wiley-Blackwell, Oxford. koetjape was isolated successfully with simple 10. Langenheim, J.H. (1994) Higher plant terpenoids: non-chromotgraphic method with high percentage A phytocentric overview of their ecological roles. yeild (Table 3). The remarkaple pharmacological Journal of Chemical Ecology, 20, 1223-1280. activity make this compound as good candidite as a 11. Harborne, J.B. and Tomas-Barberan, F.A. (eds.) drug, however, a comprehinsive toxicity study has to (1991) Ecological Chemistry and Biochemistryof Plant be carried out. Besides, it is very critical to find a Terpenoids, Clarendon, Oxford. solution of poor solubilty of it as well as its 12. Mahato, S.B. and Sen, S. (1997) Advances in bioavailabilty. triterpenoid research, 1990-1994. Phytochemistry, 44, 1185-236. 13. Morton, J.F. (ed.) (1987) Fruits of warm climates Acknowledgement(s) Julia F. Morton Miami , FL. 14. Uphof, J.C. (1959) Dictionary of Economic Plants. Hafner, New York. Zeyad D. Nassar and A.F.A. Aisha would like to 15. Burkill, I.H. (1966) Dictionary of the Economic acknowledge USM for the USM Fellowship. Products of the Malay Peninsula. Ministry of This work was financially supported by Universiti Sains Agriculture and Cooperatives, Kuala Lumpur, Malaysia. Malaysia (USM) Research University Grant [Grant 16. Perry, L.M. (1980) Medicinal Plants of East and 1001/PFARMASI/81144]. Southeast Asia. The MIT Press, Cambridge. 17. Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W.,

Mantus, E.K., Cherry, D. and Clardy, J. (1991) Limonoid Antifeedants from Seed of Sandoricum References koetjape. Journal of Natural Products, 54, 241-246. 18. Sim, K.Y. and Lee, H.T. (1972) Triterpenoid and other constituents from Sandoricum indicum. Phytochemistry, 11, 3341-3343. 1. Summner, J. (ed.) (2003) The natural history of 19. Ismail, I.S., Ito, H., Hatano, T., Taniguchi, S. and medicinal plants Timber press, Inc., Oregon Yoshida, T. (2003) Modified limonoids from the leaves 2. Samuelsson, G. (ed.) (1999) Drugs of natural origin of Sandoricum koetjape. Phytochemistry, 64, : a textbook of pharmacognosy Swedish 1345-1349. Pharmaceutical Press Stockholm. 20. King, F.E. and Morgan, J.W.W. (1960) 923. The 3. Fan, T.-P., Yeh, J.-C., Leung, K.W., Yue, P.Y.K. chemistry of extractives from hardwoods. Part XXX. and Wong, R.N.S. (2006) Angiogenesis: from plants to The constitution of katonic acid, a triterpene from blood vessels. Trends in Pharmacological Sciences, sandoricum indicum. Journal of the Chemical Society

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(Resumed), 4738-4747. 21. Kaneda, N., Pezzuto, J.M., Kinghorn, A.D., Farnsworth, N.R., Santisuk, T., Tuchinda, P., Udchachon, J. and Reutrakul, V. (1992) Plant anticancer agents, L. cytotoxic triterpenes from Sandoricum koetjape stems. J Nat Prod, 55, 654-9. 22. Kosela, S., Yulizar, Y., Chairul, Tori, M. and Asakawa, Y. (1995) Secomultiflorane-type triterpenoid acids from stem bark of Sandoricum koetjape. Phytochemistry, 38, 691-694. 23. Tanaka, T., Koyano, T., Kowithayakorn, T., Fujimoto, H., Okuyama, E., Hayashi, M., Komiyama, K. and Ishibashi, M. (2001) New Multiflorane-Type Triterpenoid Acids from Sandoricum indicum. Journal of Natural Products, 64, 1243-1245. 24. Hu, H.Y., Horton, J.K., Gryk, M.R., Prasad, R., Naron, J.M., Sun, D.A., Hecht, S.M., Wilson, S.H. and Mullen, G.P. (2004) Identification of small molecule synthetic inhibitors of DNA polymerase beta by NMR chemical shift mapping. J Biol Chem, 279, 39736-44. 25. Ismail, I.S., Ito, H., Mukainaka, T., Higashihara, H., Enjo, F., Tokuda, H., Nishino, H. and Yoshida, T. (2003) Ichthyotoxic and anticarcinogenic effects of triterpenoids from Sandoricum koetjape bark. Biol Pharm Bull, 26, 1351-3. 26. Rasadah, M.A., Khozirah, S., Aznie, A.A. and Nik, M.M. (2004) Anti-inflammatory agents from Sandoricum koetjape Merr. Phytomedicine, 11, 261-3. 27. Muhammad, I., El Sayed, K.A., Mossa, J.S., Al-Said, M.S., El-Feraly, F.S., Clark, A.M., Hufford, C.D., Oh, S. and Mayer, A.M.S. (2000) Bioactive 12-Oleanene Triterpene and Secotriterpene Acids from Maytenus undata. Journal of Natural Products, 63, 605-610. 28. Aisha, A.F.A., Alrokayan, S.A., Abu-Salah, K.M., Darwis, Y. and Abdul Majid, A.M.S. (2009) In vitro Cytotoxic and Apoptotic Properties of the Stem Bark Extract of Sandoricum koetjape on Breast Cancer Cells. Int. J. Cancer Res., 5, 123-129. 29. Aisha, A.F.A., Sahib, H.B., Abu-Salah, K.M., Darwis, Y. and Abdul Majid, A.M.S. (2009) Cytotoxic and Anti-Angiogenic Properties of the Stem Bark Extract of Sandoricum koetjape. Int. J. Cancer Res., 5, 105-114. 30. Nassar, Z.D., Aisha, A.F.A., Majid, A.M.S.A., Yeap, C.S. and Fun, H.-K. (2010) Koetjapic acid chloroform hemisolvate. Acta Crystallographica Section E, 66, o1301-o1302.

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Illustrations Illustration 1

Table 1 The classification of Sandricum koetjape

Class Magnoliopsida, Dicotyledons

Subclass Rosidae

Order Rutales

Suborder Meliineae

Family Meliaceae

Genus Sandoricum

Specific epithet koetjape Merr.

Botanical name Sandoricum koetjape

Synonyms Sandoricum indicum Cav., Sandoricum nervosum Webmedcentral > Review articles Page 6 of 16 Blume, and Melia koetjape Burm. f.[13] WMC001311 Downloaded from http://www.webmedcentral.com on 23-Dec-2011, 07:54:07 AM

Illustration 2

Table 2 The nomenclature of terpenoids.

Name No. of isoprene units No. of carbon atoms

Hemiterpenoids 1 5

Monoterpenoids 2 10

Sesquiterpenoids 3 15

Diterpenoids 4 20

Sesterterpenoids 5 25

Triterpenids 6 30

Tetraterpenoids 8 40

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Illustration 3

Table 3 The percentage yield of koetjapic acid gained by previous studies

Reference Percentage yield %

Kaneda et al., 1992 [21] 0.11 %

Tanaka et al., 2001 [23] 0.14%

Rasadah et al., 2004 [26] 0.0036%

Ismail et al., 2003 [25] 0.0825%

Nassar, et al., 2010 [30] 0.2 %

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Illustration 4

Figure 1 Pictures of leaves, seeds and fruits of S.koetjape

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Illustration 5

Figure 2 Chemical structures of triterpene isolated from S. koetjape

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Reviews Review 1

Review Title: The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape

Posted by Dr. Malek Alzhihlif on 21 Jan 2011 10:33:08 PM GMT

1 Is the subject of the article within the scope of the subject category? Yes 2 Are the interpretations / conclusions sound and justified by the data? Yes 3 Is this a new and original contribution? Yes 4 Does this paper exemplify an awareness of other research on the topic? Yes 5 Are structure and length satisfactory? Yes 6 Can you suggest brief additions or amendments or an introductory statement that will increase Yes the value of this paper for an international audience? 7 Can you suggest any reductions in the paper, or deletions of parts? No 8 Is the quality of the diction satisfactory? Yes 9 Are the illustrations and tables necessary and acceptable? Yes 10 Are the references adequate and are they all necessary? Yes 11 Are the keywords and abstract or summary informative? Yes

Rating: 8 Comment: The “Influence of medicinal plants on diseases treatment” section can be written in more concise way and I think the title does not reflect what is really discussed by the author

From my opinion the author need to introduce more information regarding the mechanism of action in the malignant cell especially the DNA polymerase inhibition story.

One attractive point mentioned in this review is the anti-bacterial activity and more information and scientific finding will add a better value for the review.

Competing interests: no Invited by the author to make a review on this article? : Yes Experience and credentials in the specific area of science: i have beed working on plant extracts activity agianst cancer for a while and some publications will come out soon

Publications in the same or a related area of science: No How to cite: Alzhihlif M.The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape [Review of the article 'The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape ' by ].WebmedCentral 1970;2(1):REVIEW_REF_NUM399

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Review 2

Review Title: The pharmacological properties of terpenoids from 'Sandronicum koetjape'

Posted by Prof. Marcello Iriti on 16 Dec 2010 03:52:22 AM GMT

1 Is the subject of the article within the scope of the subject category? Yes 2 Are the interpretations / conclusions sound and justified by the data? Yes 3 Is this a new and original contribution? Yes 4 Does this paper exemplify an awareness of other research on the topic? Yes 5 Are structure and length satisfactory? Yes 6 Can you suggest brief additions or amendments or an introductory statement that will increase Yes the value of this paper for an international audience? 7 Can you suggest any reductions in the paper, or deletions of parts? No 8 Is the quality of the diction satisfactory? No 9 Are the illustrations and tables necessary and acceptable? Yes 10 Are the references adequate and are they all necessary? Yes 11 Are the keywords and abstract or summary informative? Yes

Rating: 5 Comment: According to my opinion, the manuscript represents a satisfactory review on the pharmacological activities of Sandoricum koetjape. However, I suggest some modifications: 1. pg 2, 'Natyral products and cancer treatment', the authors should better specify the ecological role of secondary metabolites (for plant), in oppositio to their biological activities relevant to human health ('as a result' is misleading). Furthemore, I would add phenylpropanoids to the list of secondary metabolites. 2. I would introduce a review on limonoids, because of their abundance in ??S. koetjape, such as that of Roy and Saraf 2006, Limonoids, overview of significant bioactive triterpenes distributed in plants kingdom, Biol Pharm Bull, as well as the reference Pancharoen et al., 2009, Two new limonoids from the leaves of Sandoricum koetjape, Nar Prod Res 23(1):10-16. 3. A number of typing and diction erroer are present in the text, particularly in pg 4 and also in References. 4. Tables 1 and 2 have been exchamged; in tab 1 (that should be the tab 2) there is 'Sandricum' and in tab 2 (that should be the tab 1) there is 'triterpenids'. 5. In the text, fig. 1 and 2 should be reported, instead of 'Plate 1.1' and 'Figure 1.3' (pg 3) 6. The acronym MIC (minimun inhibitory concnetration) should be written in extenso

Competing interests: no Invited by the author to make a review on this article? : No Experience and credentials in the specific area of science: Biological activity of grape chemicals

Publications in the same or a related area of science: Yes References: Iriti, M.; Faoro, F. Bioactivity of grape chemicals for human health. Nat. Prod. Commun., 2009, 4, 611-634. How to cite: Iriti M.The pharmacological properties of terpenoids from 'Sandronicum koetjape'[Review of the article 'The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape ' by ].WebmedCentral

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1970;1(12):REVIEW_REF_NUM253

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Review 3

Review Title: Sandoricum Koetjape

Posted by Mr. Suchir Arora on 12 Dec 2010 12:04:11 PM GMT

1 Is the subject of the article within the scope of the subject category? Yes 2 Are the interpretations / conclusions sound and justified by the data? Yes 3 Is this a new and original contribution? Yes 4 Does this paper exemplify an awareness of other research on the topic? Yes 5 Are structure and length satisfactory? Yes 6 Can you suggest brief additions or amendments or an introductory statement that will increase No the value of this paper for an international audience? 7 Can you suggest any reductions in the paper, or deletions of parts? No 8 Is the quality of the diction satisfactory? Yes 9 Are the illustrations and tables necessary and acceptable? No 10 Are the references adequate and are they all necessary? Yes 11 Are the keywords and abstract or summary informative? Yes

Rating: 8 Comment: General comment on referring some patents as well.... there are many of them focussed on Terpenoids

Competing interests: None Invited by the author to make a review on this article? : Yes Experience and credentials in the specific area of science: Yes

Publications in the same or a related area of science: No How to cite: Arora S.Sandoricum Koetjape[Review of the article 'The Pharmacological Properties Of Terpenoids From Sandoricum Koetjape ' by ].WebmedCentral 1970;1(12):REVIEW_REF_NUM236

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