GC-MS and Bioassay-Guided Isolation of Xanthones from Mammea siamensis

https://doi.org/10.22146/ijc.79987

Wiyarat Kumutanat(1), Sakchai Hongthong(2), Sariyarach Thanasansurapong(3), Naowarat Kongkum(4), Napasawan Chumnanvej(5*)

(1) Division of Chemistry and Multidisciplinary Research in Chemistry (MulRiC) Laboratory, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand
(2) Division of Chemistry and Multidisciplinary Research in Chemistry (MulRiC) Laboratory, Faculty of Science and Technology, Rajabhat Rajanagarindra University, Chachoengsao 24000, Thailand; Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand
(3) Center of Excellence for Innovation in Chemistry (PERCH-CIC), Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand; National Nanotechnology Center, NSTDA, 111 Thailand Science Park, Klong Luang, Pathum Thani 12120, Thailand
(4) Department of Fundamental Science and Physical Education, Faculty of Science at Sriracha, Kasetsart University, Chonburi 20230, Thailand
(5) Department of Fundamental Science and Physical Education, Faculty of Science at Sriracha, Kasetsart University, Chonburi 20230, Thailand
(*) Corresponding Author

Abstract


Mammea siamensis (Miq.) T. Anders. (Calophyllaceae) plants have long been employed as an active integral composition in Thai traditional medicine. Additionally, phenylcoumarins and triterpenes were reported as major components in phytochemical research. This work explored the various parts of M. siamensis; barks, flowers, twigs, leaves, and young leaves; to determine their bioactive compounds. By using the GC-MS and bioassay guidance, two xanthones, 6-deoxyisojacareubin (1) and 1,5-dihydroxyxanthone (2), together with a mixture of phenylcoumarins, mammea A/AA cyclo D (3) and mammea A/AB cyclo D (4) have been isolated from the methanolic extract of young leaves. Their structures were identified by means of spectroscopic technique and by comparison with literature data. In particular, the current study was the first exposed report of xanthones 1 and 2 from the genus Mammea. Furthermore, compounds 1 and 2 and the methanolic young leaf extract had high antioxidant efficiency on DPPH and ABTS assays. The young leaf extract provided mild toxicity on the brine shrimp lethality test (BSLT) with LC50 value of 93.11 ± 1.37 µg/mL. In addition, the isolated compounds 1 and 2 were non-toxicity in BSLT assay. Therefore, the young leaf extract and the purified constituents 1 and 2 should be further studied and developed for using in pharmaceutical industries.

Keywords


antioxidant activity; Mammea siamensis; phenylcoumarins; toxicity; xanthones



References

[1] Ghanadian, M., Ali, Z., Khan, I.A., Balachandran, P., Nikahd, M., Aghaei, M., Mirzaei, M., and Sajjadi, S.E., 2020, A new sesquiterpenoid from the shoots of Iranian Daphne mucronata Royle with selective inhibition of STAT3 and Smad3/4 cancer-related signaling pathways, DARU J. Pharm. Sci., 28 (1), 253–262.

[2] Aghaei, M., Mirzaei, M., Ghanadian, M., Fallah, M., and Mahboodi, R., 2021, 6-Methoxylated flavonoids: Jacein, and 3-demethyljacein from Centaurea schmidii with their endoplasmic reticulum stress and apoptotic cell death in breast cancer cells along with in-silico analysis, Iran. J. Pharm. Res., 20 (2), 417–432.

[3] Shalaby, E.A., Shanab, S.M.M., Hafez, R.M., and El‑Ansary, A.E., 2023, Chemical constituents and biological activities of different extracts from ginger plant (Zingiber offcinale), Chem. Biol. Technol. Agric., 10 (1), 14.

[4] Dyshlyuk, L.S., Fotina, N.V., Milentyeva, I.S., Ivanova, S.A., Izgarysheva, N.V., and Golubtsova, Y.V., 2024, Antimicrobial and antioxidant activity of Panax ginseng and Hedysarum neglectum root crop extracts, Braz. J. Biol., 84, e256944.

[5] Kefi, S., Essid, R., Papetti, A., Abid, G., Bouslama, L., Aouani, E., Tabbene, O., and Limam, F., 2023, Antioxidant, antibacterial, and antileishmanial potential of Micromeria nervosa extracts and molecular mechanism of action of the bioactive compound, J. Appl. Microbiol., 134 (2), lxad007.

[6] Sakyiamah, M.M., Gordon, P.K., Bolah, P., Baffour, P.K., Ehun, E., Quasie, O., Kumadoh, D., Archer, M.A., Mintah, S.O., and Appiah, A.A., 2023, Assessment of the phytochemical composition and antimicrobial properties of Tapinanthus bangwensis leaves hosted by the branches of Persea americana, BMC Complementary Med. Ther., 23 (1), 34.

[7] Abdeyazdan, S., Mohajeri, M., Saberi, S., Mirzaei, M., Ayatollahi, S.A., Saghaei, L., and Ghanadian, M., 2022, Sb(V) kaempferol and quercetin derivative complexes: Synthesis, characterization and antileishmanial activities, Iran. J. Pharm. Res., 21 (1), e128379.

[8] Sukkasem, K., Panthong, S., and Itharat, A., 2016, Antimicrobial activities of Thai traditional remedy “Kheaw-Hom” and its plant ingredients for skin infection treatment in chickenpox, J. Med. Assoc. Thailand, 99 (Suppl. 4), S116–S123.

[9] Streinrut, L., Itharat, A., and Ruangnoo, S., 2011, Free radical scavenging and lipid peroxidation of Thai medicinal plants used for diabetic treatment, J. Med. Assoc. Thailand, 94 (Suppl. 7), S178–S182.

[10] Lemus, C., Smith-Ravin, J., and Marcelin, O., 2021, Mammea americana: A review of traditional uses, phytochemistry and biological activities, J. Herb. Med., 29, 100466.

[11] Byrne, C., Parnell, J.A.N., and Chayamarit, K., 2018, Systematics of the Thai Calophyllaceae and Hypericaceae with comments on the Kielmeyeroidae (Clusiaceae), Thai Forest Bull., Bot., 46 (2), 162–216.

[12] Luo, F., Manse, Y., Chaipech, S., Pongpiriyadacha, Y., Muraoka, O., and Morikawa, T., 2023, Structures of Mammeasins P and Q, coumarin-related polysubstituted benzofurans, from the Thai medicinal plant Mammea siamensis (Miq.) T. Anders.: Anti-proliferative activity of coumarin constituents against human prostate carcinoma cell line LNCaP, Pharmaceuticals, 16 (2), 231.

[13] Sangkaruk, R., Rungrojsakul, M., Tima, S., and Anuchapreeda, S., 2017, Effect of Thai Saraphi flower extracts on WT1 and Bcr/Abl protein expression in leukemic cell lines, Afr. J. Tradit., Complementary Altern. Med., 14 (2), 16–24.

[14] Ninomiya, K., Shibatani, K., Sueyoshi, M., Chaipech, S., Pongpiriyadacha, Y., Hayakawa, T., Muraoka, O., and Morikawa, T., 2016, Aromatase inhibitory activity of geranylated coumarins, Mammeasins C and D, isolated from the flowers of Mammea siamensis, Chem. Pharm. Bull., 64 (7), 880–885.

[15] Prachyawarakorn, V., Mahidol, C., and Ruchirawat, S., 2006, Siamenols A–D, four new coumarins from Mammea siamensis, Chem. Pharm. Bull., 54 (6), 884–886.

[16] Laphookhieo, S., Promnart, P., Syers, J.K., Kanjana-Opas, A., Ponglimanont, C., and Karalai, C., 2007, Coumarins and xanthones from the seeds of Mammea siamensis, J. Braz. Chem. Soc., 18 (5), 1077–1080.

[17] Rungrojsakul, M., Katekunlaphan, T., Saiai, A., Ampasavate, C., Okonogi, S., Sweeney, C.A., and Anuchapreeda, S., 2016, Down-regulatory mechanism of mammea E/BB from Mammea siamensis seed extract on Wilms’ tumor 1 expression in K562 cells, BMC Complementary Altern. Med., 16 (1), 130.

[18] Rungrojsakul, M., Saiai, A., Ampasavate, C., Anuchapreeda, S., and Okonogi, S., 2016, Inhibitory effect of mammea E/BB from Mammea siamensis seed extract on Wilms’ tumour 1 protein expression in a K562 leukaemic cell line, Nat. Prod. Res., 30 (4), 443–447.

[19] Ngo, N.T.N., Nguyen, V.T., Vo, H.V., Vang, O., Duus, F., Ho, T.D.H., Pham, H.D., and Nguyen, L.H.D., 2010, Cytotoxic coumarins from the bark of Mammea siamensis, Chem. Pharm. Bull., 58 (11), 1487–1491.

[20] Luo, F., Sugita, H., Muraki, K., Saeki, S., Chaipech, S., Pongpiriyadacha, Y., Muraoka, O., and Morikawa, T., 2021, Anti-proliferative activities of coumarins from the Thai medicinal plant Mammea siamensis (Miq.) T. Anders. against human digestive tract carcinoma cell lines, Fitoterapia, 148, 104780.

[21] Balza, F., Abramowski, Z., Towers, G.H.N., and Wiriyachitra, P., 1989, Identification of proanthocyanidin polymers as the piscicidal constituents of Mammea siamensis, Polygonum stagninum and Diospyros diepenhorstii, Phytochemistry, 28 (7), 1827–1830.

[22] El-Amier, Y.A., Soliman, H.M., ElHalawany, E.F., and El-Nabawy, B.S., 2022, Chemical characterization of Reichardia tingitana methanolic extract and evaluation of its antioxidant and anticancer activity, Egypt. J. Chem., 65 (132), 933–940.

[23] Maisarah, A.M., Nurul Amira, B., Asmah, R., and Fauziah, O., 2013, Antioxidant analysis of different parts of Carica papaya, Int. Food Res. J., 20 (3), 1043–1048.

[24] Liu, H.Y., Liu, Y., Mai, Y.H., Guo, H., He, X.Q., Xia, Y., Li, H., Zhuang, Q.G., and Gan, R.Y., 2021, Phenolic content, main flavonoids, and antioxidant capacity of instant sweet tea (Lithocarpus litseifolius [Hance] Chun) prepared with different raw materials and drying methods, Foods, 10 (8), 1930.

[25] Sumartini, S., Ratrinia, P.W., and Hutabarat, R.F., 2022, The effect of mangrove types and leave maturity on the mangrove leaves (Sonneratia alba) and (Rhizophora mucronata) tea powder, IOP Conf. Ser.: Earth Environ. Sci., 967, 012018.

[26] Dorkbuakaew, N., Ruengnet, P., Pradmeeteekul, P., Nimkamnerd, J., Nantitanon, W., and Thitipramote, N., 2016, Bioactive compounds and antioxidant activities of Camellia sinensis var. assamica in different leave maturity from Northern Thailand, Int. Food Res. J., 23 (5), 2291–2295.

[27] Mistriyani, M., Riyanto, S., Windarsih, A., and Rohman, A., 2021, Antioxidant activities and identification of an active compound from rambutan (Nephelium lappaceum L.) peel, Indones. J. Chem., 21 (2), 259–267.

[28] Hidayati, M.D., Ersam, T., Shimizu, K., and Fatmawati, S., 2017, Antioxidant activity of Syzygium polynthum extracts, Indones. J. Chem., 17 (1), 49–53.

[29] Wickramaratne, M.N., Punchihewa, J.C., and Wickramaratne, D.B.M., 2016, In-vitro alpha amylase inhibitory activity of the leaf extracts of Adenanthera pavonina, BMC Complementary Altern. Med., 16 (1), 466.

[30] Priska, M., Peni, N., and Carvallo, L., 2019, Phytochemicals screening and antioxidant effectiveness of garlic (Allium sativum) from Timor Island, Biosaintifika, 11 (1), 1–7.

[31] Mkangara, M., and Mpenda, F.N., 2022, Antimicrobial and cytotoxicity activities of medicinal plants against Salmonella gallinarum isolated from chickens, Vet. Med. Int., 2022, 2294120.

[32] Clemen-Pascual, L.M., Macahig, R.A.S., and Rojas, N.R.L., 2022, Comparative toxicity, phytochemistry, and use of 53 Philippine medicinal plants, Toxicol. Rep., 9, 22–35.

[33] Guo, P.J., Chen, T., Zheng, L., Peng, S., Lv, K.Q., Wang, W.Q., and Xuan, L.J., 2022, Two new xanthones from Hypericum japonicum and their lipid-lowering activities, Phytochem. Lett., 49, 40–44.

[34] Hano, Y., Matsumoto, Y., Sun, J.Y., and Nomura, T., 1990, Structures of three new isoprenylated xanthones, cudraxanthones E, F, and G, Planta Med., 56 (4), 399–402.

[35] Sabphon, C., Sermboonpaisarn, T., and Sawasdee, P., 2012, Cholinesterase inhibitory activities of xanthones from Anaxagorea luzonensis A. Gray, J. Med. Plants Res., 6 (21), 3781–3785.

[36] Teh, S.S., Ee, G.C.L., and Mah, S.H., 2013, Chemical constituents and new xanthone derivatives from Mesua ferrea and Mesua congestiflora, Asian J. Chem., 25 (15), 8780–8784.

[37] Verotta, L., Lovaglio, E., Vidari, G., Finzi, P.V., Neri, M.G., Raimondi, A., Parapini, S., Taramelli, D., Riva, A., and Bombardelli, E., 2004, 4-Alkyl- and 4-phenylcoumarins from Mesua ferrea as promising multidrug resistant antibacterials, Phytochemistry, 65 (21), 2867–2879.

[38] Canning, C., Sun, S., Ji, X., Gupta, S., and Zhou, K., 2013, Antibacterial and cytotoxic activity of isoprenylated coumarin mammea A/AA isolated from Mammea africana, J. Ethnopharmacol., 147 (1), 259–262.

[39] Morikawa, T., Luo, F., Manse, Y., Sugita, H., Saeki, S., Chaipech, S., Pongpiriyadacha, Y., Muraoka, O., and Ninomiya, K., 2020, Geranylated coumarins from Thai medicinal plant Mammea siamensis with testosterone 5a-reductase inhibitory activity, Front. Chem., 8, 00199.

[40] Luo, F., Manse, Y., Chaipech, S., Pongpiriyadacha, Y., Muraoka, O., and Morikawa, T., 2022, Phytochemicals with chemopreventive activity obtained from the Thai medicinal plant Mammea siamensis (Miq.) T. Anders.: Isolation and structure determination of new prenylcoumarins with inhibitory activity against aromatase, Int. J. Mol. Sci., 23 (19), 11233.



DOI: https://doi.org/10.22146/ijc.79987

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