Sains Malaysiana 54(5)(2025): 1345-1355

http://doi.org/10.17576/jsm-2025-5405-12

Oligostilbenoids and Phenolic Compounds from the Stem Bark of Shorea materialis RIDL. (Dipterocarpaceae)

(Oligostilbenoid dan Sebatian Fenol daripada Kulit Batang Shorea materialis RIDL. (Dipterocarpaceae))

MUHAMMAD SULAIMAN MOHD JOHARI^1,2, NIK FATINI NIK AZMIN¹, WAN AZMIZA SYAHIRA WAN AZHAR¹, SITI ZAKIRAH AZAHAR^1,2, NOORAZLINA ADNAN^1,2,3, NURUL SHAHIRA ZAKARIA¹, FATIMAH SALIM^1,2, NORIZAN AHMAT³ & AISYAH SALIHAH KAMAROZAMAN^2,3,*

¹Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia

²Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA, Cawangan Selangor, Kampus Puncak Alam, 42300 Bandar Puncak Alam, Selangor, Malaysia

³Centre of Foundation Studies, Universiti Teknologi MARA, Cawangan Selangor, Kampus Dengkil, 43800 Dengkil, Selangor, Malaysia

Received: 25 April 2024/Accepted: 24 February 2025

Abstract

The Shorea genus is known for its abundance of sources of oligostilbenoids, which exhibit diverse biological functions. Nevertheless, despite its considerable potential, there remains a dearth of phytochemical investigations including Shorea materialis. Consequently, this study aims to isolate the chemical constituents from the stem bark of this species. The crude extract of S. materialis was obtained from the maceration technique and fractionation using vacuum liquid chromatography. The resulting fractions were further purified via column chromatography. The molecular structures of the isolated molecules were determined using various spectroscopic techniques. Two dimer stilbenoids, ampelopsins A (1) and D (2), three trimers, namely α-viniferin (3), hopeanolin (4) and davidiol A (5), one tetramer, vaticanol B (6), together with two phenolic compounds, p-hydroxybenzaldehyde and (7) 2,3,5-trihydroxybenzoic acid (8) were effectively isolated. The isolation of these compounds was the first report from this species.

Keywords: Dipterocarpaceae; oligostilbenoids; phenolic compounds; Shorea materialis   

Abstrak

Genus Shorea terkenal dengan kekayaan sumber oligostilbenoid yang menunjukkan pelbagai fungsi biologi. Walaupun genus ini mempunyai potensi yang tinggi, kajian fitokimia berkaitan spesies daripada genus ini masih sedikit termasuklah Shorea materialis. Oleh itu, kajian ini dijalankan bertujuan untuk mengasingkan sebatian kimia daripada kulit batang spesies ini. Ekstrak kasar S. materialis diperoleh daripada kaedah rendaman dan fraksinasi menggunakan kromatografi cecair vakum. Fraksi yang diperoleh seterusnya ditulenkan lagi menggunakan kromatografi turus. Struktur molekul sebatian yang telah dipencilkan ditentukan menggunakan pelbagai teknik spektroskopi. Dua sebatian stilbenoid dimer, ampelopsin A (1) dan D (2), tiga stilbenoid trimer, iaitu α-viniferin (3), hopeanolin (4) dan davidiol A (5), satu stilbenoid tetramer, vaticanol B (6), bersama dengan dua sebatian fenol, p-hidroksibenzaldehid dan (7) asid benzoik 2,3,5-trihidroksi (8) telah berjaya dipencilkan. Penulenan sebatian ini merupakan pertama kali dilaporkan daripada spesies ini.

Kata kunci: Dipterocarpaceae; oligostilbenoid; sebatian fenol; Shorea materialis  

REFERENCES

Aoki-Utsubo, C., Hanafi, M., Armanti, D.T., Fuchino, H., Kawahara, N., Hartati, S. & Hotta, H. 2023. Identification of an oligostilbene, vaticanol B, from Dryobalanops aromatica leaves as an antiviral compound against the Hepatitis C virus. Biological and Pharmaceutical Bulletin 46(8): 1079-1087.

Ashton, P.S. 2004. Dipterocarpaceae. In Tree Flora of Sabah and Sarawak, edited by Soepadmo, E., Saw, L.G. & Chung, R.C.K. Malaysia: Forest Research Institute Malaysia, Sabah Foresty Department, and Sarawak Foresty Department. pp. 63-388.

Chhabra, G., Singh, C.K., Amiri, D., Akula, N. & Ahmad, N. 2021. Recent advancements on immunomodulatory mechanisms of resveratrol in tumor microenvironment. Molecules 26: 1343.

Corner, E.J.H. 1988. Wayside trees of Malaya. Malayan Nature Society 1: 296-304.

Espinoza, J.L. & Inaoka, P.T. 2017. Gnetin‐C and other resveratrol oligomers with cancer chemopreventive potential. Annals of the New York Academy of Sciences 1403(1): 5-14.

Ge, H.M., Huang, B., Tan, S.H., Shi, D.H., Song, Y.C. & Tan, R.X. 2006. Bioactive oligostilbenoids from the stem bark of Hopea exalata. Journal of Natural Products 69(12): 1800-1802.

Guo, Z., Cheng, Y., Huang, W. & Jiao, R. 2020. Shoreanol A and B, unprecedented oligostilbenoids from the twigs of Shorea obtusa Wall. Fitoterapia 142: 104502.

Haryoto, H., Wibowo, A., Ahmat, N. & Khong, H.Y. 2014. Resveratrol oligomers from the tree bark of Shorea accuminatissima: Their properties and significance. Medicinal Plants 6(2): 120-127.

Haryoto, H., Hakim, E.H., Syah, Y.M., Achmad, S.A., Juliawaty, L.D., Din, L.B. & Latip, J. 2008. Trimer resveratrol dari kulit batang Shorea rugosa dan Shorea brunnescens (Dipterocarpaceae). J. Sains MIPA 14(1): 8-12.

Ito, T., Nishiguchi, M. & Iinuma, M. 2019. Three new resveratrol trimer di-C-glucosides in Shorea uliginosa. Phytochemistry Letters 32: 123-128.

Ito, T., Nishiguchi, M., Fukaya, M., Ryu, K. & Iinuma, M. 2022. Occurrence of a resveratrol trimer diglucoside derivative with a fused heptacyclic skeleton in Shorea uliginosa. Phytochemistry Letters 49: 120-124.

Ito, T., Tanaka, T., Ido, Y., Nakaya, K., Iinuma, M. & Riswan, S. 2000. Four new stilbenoid C-glucosides isolated from the stem bark of Shorea hemsleyana. Chemical & Pharmaceutical Bulletin 48(12): 1959-1963.

Ito, T., Hayashi, K., Nishiguchi, M., Hayashi, T. & Iinuma, M. 2018. Resveratrol oligomer C-glucosides and anti-viral resveratrol tetramers isolated from the stem bark of Shorea uliginosa. Phytochemistry Letters 28: 1-7.

Jiang, X., Wang, W., Wang, H., He, Z.H., Yang, Y., Wang, K. & Han, B. 2022. Solvent-free aerobic photocatalytic oxidation of alcohols to aldehydes over ZnO/C₃N₄. Green Chemistry 24(19): 7652-7660.

Jong, K. 1976. Cytology of the Dipterocarpaceae: Tropical Trees. London: Academic Press.

Kamarozaman, A.S., Latip, J., Syah, Y.M., Rajab, N. & Jaloh, A. 2013. Oligostilbenoids from Vatica pauciflora and the oxidative effect on Chang cells. Journal of Physics: Conference Series 423: 012045.

Kamarozaman, A.S., Ahmat, N., Sharif, F.N.S., Azmi, N.A., Johari, M.S.M., Hafiz, Z.Z., Adenan, M.I. & Azmin, N.F.N. 2019. Bioactive oligostilbenoids from Shorea leprosula Miq. Research Journal of Chemistry and Environment 23(11): 65-69.

Karplus, M. 1963. Vicinal proton coupling in nuclear magnetic resonance. J. Am. Chem. Soc. 85: 2870-2871.

Larjavaara, M. & Muller-Landau, H.C. 2013. Measuring tree height: A quantitative comparison of two common field methods in a moist tropical forest. Methods in Ecology and Evolution 4(9): 793-801.

Mabberley, D.J. 2017. The Plant-Book. 2nd ed., Cambridge: Cambridge University Press. p. 858.

Morikawa, T., Chaipech, S., Matsuda, H., Hamao, M., Umeda, Y., Sato, H. & Muraoka, O. 2012. Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3, 4-dihydroisocoumarins from the bark of Shorea roxburghii. Bioorganic & Medicinal Chemistry 20(2): 832-840.

Moriyama, H., Moriyama, M., Ninomiya, K., Morikawa, T. & Hayakawa, T. 2016. Inhibitory effects of oligostilbenoids from the bark of Shorea roxburghii on malignant melanoma cell growth: Implications for novel topical anticancer candidates. Biol. Pharm. Bull. 39: 1675-1682.

Mufarhatun, N., Hilwan, I. & Rachmat, H.H. 2021. Identification of red meranti group (Shorea spp., Dipterocarpaceae) saplings based on variations in the morphological features of quantitative leaves. Jurnal Penelitian Hutan dan Konservasi Alam 18(2): 137-149.

Muhammad, N., Din, L.B., Ibrahim, N., Zakaria, Z. & Yaacob, W.A. 2014. Hopeanolin and other resveratrol oligomers from the twigs of Shorea acuminata: Antioxidant properties and chemotaxonomic significance. The Open Conference Proceedings Journal 5(1): 5-10.

Muharini, R., Hakim, E.H., Achmad, S.A., Aimi, N., Makmur, L., Syah, Y.M. & Takayama, H. 2001. α-viniferin, a trimer stilbenoid and related compounds from Shorea guiso Blume.  Third International Seminar on Tropical Rainforest Plants and Their Utilisation for Development, Padang, Indonesia 12: 83.

Nazri, N.A.A.M., Ahmat, N., Abdullah, M., Sidik, N.J. & Johari, S.A.T.T. 2012. Antioxidant, antimicrobial and cytotoxic activities of resveratrol oligomers of Shorea macroptera Dyer. Australian Journal of Basic and Applied Sciences 6(8): 431-436.

Oshima, Y. & Ueno, Y. 1993. Ampelopsins E, E, H and cis-ampelopsin E, oligostilbenes from Ampelopsis brevipedunculata var. Hancei roots. Phytochemistry 33(1): 179-182.

Oshima, Y., Ueno, Y., Hikino, H., Yang, L.L. & Yen, K.Y. 1990. Ampelopsins A, B and C, new oligostilbenes of Ampelopsis brevipedunculatavar. hancei. Tetrahedron 46: 5121-5126.

Patcharamun, W., Sichaem, J., Siripong, P., Khumkratok, S., Jong-aramruang, J. & Tip-pyang, S. 2011. A new dimeric resveratrol from the roots of Shorea roxburghii. Fitoterapia 82(3): 489-492.

Rosyidah, K., Syah, Y.M., Achmad, S.A., Hakim, E.H., Makmur, L., Juliawati, L.D. & Said, I.M. 2005. Dua senyawa oligomer resveratrol dari kulit batang Shorea parvifolia Dyer. (Dipterocarpaceaea). The 6th ITB-UKM Joint Seminar on Chemistry 62: 508-513.

Soni, R.K., Dixit, V., Irchhaiya, R.I. & Singh, H. 2013. A review update on Shorea robusta Gaertn F. (Sal). Journal of Drug Delivery and Therapeutics 3(6): 127-132.

Takaya, Y., Yan, K.X., Terashima, K., Ito, J. & Niwa, M. 2002. Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F. Tetrahedron 58(36): 7259-7265.

Tanaka, T., Ito, T., Nakaya, K., Iinuma, M. & Riswan, S. 2000. Oligostilbenoids in stem bark of Vatica rassak. Phytochemistry 54: 63-69.

Tarbeeva, D.V., Fedoreev, S.A., Veselova, M.V., Kalinovskii, A.I., Gorovoi, P.G., Vishchuk, O.S. & Zadorozhnyi, P.A. 2015. Polyphenolic metabolites from Iris pseudacorus roots. Chemistry of Natural Compounds 51: 451-455.

Woodhead, S., Galeffi, C. & Bettolo, G.M. 1982. p-Hydroxybenzaldehyde as a major constituent of the epicuticular wax of seedling Sorghum bicolor. Phytochemistry 21(2): 455-456.

Yong, W.S.Y., Chua, L.S.L., Suhaida, M. & Aslina, B. 2011. Forest Research Institute Malaysia: A Sanctuary for Threatened Trees (Research Pamphlet; No. 130). Kepong: Forest Research Institute Malaysia.

Zawawi, N.K.N.A., Ahmat, N., Mazatulikhma, M.Z., Shafiq, R.M., Wahid, N.H. & Sufian, A.S. 2013. Bioactive oligostilbenoids from Shorea maxwelliana King and their chemotaxonomic significance. Natural Product Research 27(17): 1589-1593.

Zhang, J., Henry, E. & Zhang, L. 2020. In vitro comparison of anticancer and immunomodulatory activities of resveratrol and its oligomers. Journal of Emerging Investigators 3: 1-8.

*Corresponding author; email: aisyah2910@uitm.edu.my