Woodiixanthone A from the Stem Bark of Calophyllum woodii P. F. Stevens

Woodiixanthone A from the Stem Bark of Calophyllum woodii P. F. 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F. Stevens Sheril Nur Haziani, VIVIEN JONG YI MIAN This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-6158637/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract A new pyranocoumarin, wooiixanthone A (1), along with seven known compounds, isocalanone (2), calanone (3), euxanthone (4), teysmanone A (5), tovopyrifolin C (6) 6-deoxyjacaruebin (7) and friedelin (8) were isolated from the stem bark of Calophyllum woodie P. F. Stevens collected from Sarawak. The structure of (1) was confirmed using 1D NMR, FTIR, and MS spectra. Natural Product Chemistry woodiixanthone A Calophyllum woodii NMR characterization Figures Figure 1 1. Introduction The genus Calophyllum , a large group of trees that are members of the Calophyllaceae family comprises approximately 180–200 species, some of which are indigenous to Sarawak, Malaysia's tropical rainforest (Lim et al., 2019). This woody tree exclusively grows on sandy sea beaches along the Western Ghats of India and other parts of the world such as Tropical Asia, East Africa, Malaysia, Vietnam, Indonesia, Philippines, Australia, and several Pacific islands (Pawar & Patil, 2019). The phytochemical study of Calophyllum has revealed that it is a rich source of bioactive secondary metabolites, and several species of the genus have been explored for their phytochemical content (Gupta & Gupta, 2020). These include xanthones, flavonoids, acylphloroglucinols, terpenoids, and chromanones, which have also been reported to be present in plants within this genus. (Ogasawara et al., 2022). The plant has a long history of traditional and therapeutic uses, and it has been reported to have several medicinally important bioactive principles including anti_HIV, anti-microbial, cytotoxic activities, antimalarial and antioxidant properties (Daud et al., 2021). C. woodii , also known as ‘Billian’ or ‘Kayu Billian’ is a medium-sized to large tree native belonging to the Myrtaceae family, primarily found in the wet tropical biome of North and Northwest Borneo. This plant has gained attention for its potential medicinal uses. However, research on the biological and phytochemical properties of C. woodii has yielded few scientific reports up to recently. As part of an ongoing phytochemical study on Sarawak Calophyllum plants, we are pleased to report the structural elucidation and isolation of a new pyranocoumarin, named woodiixanthone A ( 1 ) and identified as 5,7-dihydroxy-8-(3-hydroxy-2-methylbutanoyl)-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H-chromen-2-one. 2. Result and Discussion Phytochemical study on the hexane extract of C. woodii yielded a new pyranocoumarin, woodiixanthone ( 1 ) along with seven known compounds, isocalanone ( 2 ), calanone ( 3 ), euxanthone ( 4 ), teysmanone A ( 5 ), tovopyrifolin C ( 6 ) 6-deoxyjacaruebin ( 7 ) and friedelin ( 8 ). Woodiixanthone ( 1 ) was isolated as pale-yellow crystal, displayed m/z of 422.17 corresponding to the molecular formula of C 25 H 26 O 6 . The 13 C NMR spectrum of 1 showed signals corresponding to 25 carbons, including 4 methyl, 1 methine, and 7 quaternary carbons. Analysis on the 1 H NMR spectrum showed a chelated hydroxyl group (O-H) at the most downfield of the region in the form of singlet at δ H 13.28 was assigned as 7-OH attached to C-7. A singlet assigned as H-3 showed a lone aromatic proton at δ H 5.93 (1H, s) attached to the nucleus of the coumarin. A triplet at δ H 5.28 (1 H, t, J = 7.4 Hz) and a doublet at δ H 3.47 (2H, d , J = 7.4 Hz) displayed the existence of a prenyl group in the structure. In addition, compound 1 demonstrated 4-phenyl signals with two pairs of multiplets at δ H 7.42 were assigned as H-3’, H-4’ and H-5’ and the other multiplet at δ H 7.33 for the aromatic proton H-2’ and H-6’. Furthermore, the existence of 8-(3-hydroxy-2-methylbutanoyl) signals was proved at δ H 4.49 (1H, m , H-3’’’), δ H 1.22 (3H, d , J = 6.3 Hz, H-4’’’) and δ H 1.61 (3H, d, J = 6.3 Hz, H-5’’’). The isolated compound was deduced to be 5,7-dihydroxy-8-(3-hydroxy-2-methylbutanoyl)-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H-chromen-2-one. The identified compound was isolated for the first time from C. woodii . The 1 H and 13 C NMR spectral data of woodiixanthone A in acetone-d 6 Position d C (ppm) d H (ppm) HMBC COSY 2 158.6 3 112.4 5.93 (1H, s ) C-2, C-4a, C-1ʹ 4 155.6 4a 101.9 5 160.4 C-7 6 108.0 7 160.4 8 103.4 8a 159.0 1ʹ 139.1 2ʹ 127.3 7.42 (1H, m ) C-4ʹ H-3ʹ 3ʹ 128.2 7.33 (1H, m ) C-1ʹ, C-2ʹ H-2ʹ 4ʹ 127.6 7.42 (1H, m ) 5ʹ 128.2 7.42 (1H, m ) C-1ʹ, C-6ʹ H-6ʹ 6ʹ 127.3 7.42 (1H, m ) C-4ʹ H-5 ʹ 1ʺ 21.4 3.47 (2H, d , J = 7.4 Hz) 2ʺ 121.4 5.28 (1H, t , J = 7.4 Hz) C-3ʺ, C-4ʺ, C-5ʺ H-3ʺ 3ʺ 131.2 H-2ʺ 4ʺ 17.2 1.87 (3H, s ) C-5 ʺ 5ʺ 25.0 1.69 (3H, s ) C-4 ʺ 1ʺʹ 201.0 C-3ʺʹ 2ʺʹ 45.6 2.85 (1H, m ) C-1ʺʹ, C-3ʺʹ, C-4ʺʹ H-3ʺʹ 3ʺʹ 79.2 4.49 (1H, m ) C-1ʺʹ, C-4ʺʹ 4ʺʹ 9.2 1.22 (3H, d , J = 6.3 Hz) C-1ʺʹ 5ʺʹ 18.8 1.61 (3H, d , J = 6.3 Hz) H-5ʺʹ 7-OH 160.4 13.28 (1H, s ) C-8 H-8 3. Experiment Section 3.1 General The BRUKER AVANCE III 400 MHz spectrometer (Karlsruhe, Germany) with 400 MHz and 100 MHz instrument operating system, respectively, were used to obtain the 1 H NMR and 13 C NMR spectra. In the corresponding analysis, deuterated acetone (acetone-d 6 ) and deuterated chloroform (CDCl 3 ) were employed 3.2 Plant Material The stem bark of C. woodii were obtained from the herbarium vouchers located at Universiti Teknologi MARA (UiTM), Kampus Samarahan 2, Sarawak. The stem barks were air-dried at room temperature and were ground into powder form prior to the extraction process. 3.3 Extraction and isolation The stem bark of C. woodii was dried and ground to fine powder producing 1.2 kg samples. The samples were macerated with n- hexane and allowed to stand for 14 days at room temperature. The macerated sample was filtered, and n-hexane was added again to the stem bark after the first filtration was collected. The samples were then evaporated by using a rotary evaporator to dry under reduced pressure at 40°C. The yield of 10.3447 g n -hexane extracts. The crude extract was then subjected to silica gel column chromatography (CC) using n-hexane as the initial solvent, followed by elution with mixtures of n-hexane and EtOAc (ranging from 90:10 to 0:100), resulting in 13 fractions (CWH1-13). Fraction CWH5-6 was further isolated using Sephadex LH-20 CC and eluted with 100% MeOH to obtain 7 subfractions (CWH56A-G). Purification of subfraction CWH56H-G using chromatatron elution with 100% chloroform yielded 2.5 mg of woodiixanthone A in the form of pale yellow crystals. 4. Conclusion The isolation of the n-hexane extract from C. woodii stem bark has led to the discovery of a new compound, woodiixanthone A. The unique structure of the compound makes it a promising subject for further investigation Declarations Declarations Conflict of Interest: The authors declare no conflict of interest. Author Contributions: SNH has contributed to writing - original draft preparation resources, and VJYM conceptualization writing- review, supervision, and funding acquisition. Acknowledgments: The authors would like to acknowledge the UiTM Sarawak for financial assistance and support given throughout the research conducted on the genus Calophyllum by VJYM and SNH. References Aminudin, N. I., Ahmad, F., & Taher, M. (2019). Antibacterial and antioxidant activities of extracts from Calophyllum ferrugineum and Calophyllum incrassatum . Malaysian Journal of Analytical Sciences, 23 (4), 637-647. Cassien, M., Mercier, A., Thétiot-Laurent, S., Culcasi, M., Ricquebourg, E., Asteian, A., ... & Pietri, S. (2021). Improving the antioxidant properties of Calophyllum inophyllum seed oil from French Polynesia: Development and biological applications of resinous ethanol-soluble extracts. Antioxidants, 10 (2), 199. Daud, S., Karunakaran, T., Santhanam, R., Nagaratnam, S. R., Jong, V. Y. M., & Ee, G. C. L. (2021). Cytotoxicity and nitric oxide inhibitory activities of xanthones isolated from Calophyllum hosei Ridl. Natural Product Research, 35 (24), 6067-6072. de Sousa, N. F., Scotti, L., de Moura, É. P., dos Santos Maia, M., Rodrigues, G. C. S., de Medeiros, H. I. R., ... & Scotti, M. T. (2022). Computer-aided drug design methodologies with natural products in the drug research against Alzheimer’s disease. Current Neuropharmacology, 20 (5), 857. Działo, M., Mierziak, J., Korzun, U., Preisner, M., Szopa, J., & Kulma, A. (2016). The potential of plant phenolics in prevention and therapy of skin disorders. International Journal of Molecular Sciences, 17 (2), 160. Gupta, S., & Gupta, P. (2020). The genus Calophyllum : Review of ethnomedicinal uses, phytochemistry, and pharmacology. In Bioactive natural products in drug discovery (pp. 215-242). Karunakaran, T., Firouz, N. S., Santhanam, R., & Jong, V. Y. M. (2022). Phytochemicals from Calophyllum macrocarpum Hook. f. and its cytotoxic activities. Natural Product Research, 36 (2), 654-659. Lim, C. K., Subramaniam, H., Say, Y. H., Jong, V. Y. M., Khaledi, H., & Chee, C. F. (2015). A new chromanone acid from the stem bark of Calophyllum teysmannii . Natural Product Research, 29 (21), 1970-1977. Lizazman, M. A., Jong, V. Y. M., Chua, P., Lim, W. K., & Karunakaran, T. (2023). Phytochemicals from Calophyllum canum Hook f. ex T. Anderson and their neuroprotective effects. Natural Product Research, 37 (12), 2043-2048. Ogasawara, A., Noguchi, R., Shigi, T., Nugroho, A. E., Hirasawa, Y., Kaneda, T., ... & Morita, H. (2022). Caloforines A–G, coumarins from the bark of Calophyllum scriblitifolium . Journal of Natural Medicines, 76 (3), 645-657. Pawar, K. D., & Patil, R. V. (2020). Phytochemicals of Calophyllum inophyllum . In H. Murthy & V. Bapat (Eds.), Bioactive compounds in underutilized fruits and nuts (pp. [insert page range if available]). Reference Series in Phytochemistry. Springer, Cham. Additional Declarations The authors declare no competing interests. Supplementary Files SPECTRALDATAWOOIIXANTHONE.docx Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-6158637","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":424279744,"identity":"3f4c8c48-1080-483a-9cda-98334f33380c","order_by":0,"name":"Sheril Nur Haziani","email":"","orcid":"","institution":"Universiti Teknologi MARA Sarawak Branch","correspondingAuthor":false,"prefix":"","firstName":"Sheril","middleName":"Nur","lastName":"Haziani","suffix":""},{"id":424279745,"identity":"f4f184f9-ff9b-4d13-8298-9753257e3f1d","order_by":1,"name":"VIVIEN JONG YI MIAN","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAwklEQVRIiWNgGAWjYDACZgaGAwwMNgxsYB4b8VrSGNjYiNYCAYehqonRYnCcx/DAxx3nE/vkuxMYPpQdZtCdkUBAy2Eeg4Mzz9xObGPj3cA449xhBrMbBLRINrMlHOZtg2hh5m0jVsvftnMQLX+J0cLPzHzgMGPbAYgWRmK1HOxtSzZuY8vdcLDnXDqP2ZkH+LWw8R9s/vCzzU52fvPZjQ9+lFnLmR0nYAsKOADEPAwCpGiBuvUAyVpGwSgYBaNgeAMAR5NExMlspHgAAAAASUVORK5CYII=","orcid":"","institution":"Universiti Teknologi MARA Sarawak Branch","correspondingAuthor":true,"prefix":"","firstName":"VIVIEN","middleName":"JONG YI","lastName":"MIAN","suffix":""}],"badges":[],"createdAt":"2025-03-05 04:15:17","currentVersionCode":1,"declarations":{"humanSubjects":false,"vertebrateSubjects":false,"conflictsOfInterestStatement":false,"humanSubjectEthicalGuidelines":false,"humanSubjectConsent":false,"humanSubjectClinicalTrial":false,"humanSubjectCaseReport":false,"vertebrateSubjectEthicalGuidelines":false},"doi":"10.21203/rs.3.rs-6158637/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-6158637/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":77853519,"identity":"0f320a6d-7a69-4af1-9503-98f13ddf429e","added_by":"auto","created_at":"2025-03-06 07:20:58","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":117341,"visible":true,"origin":"","legend":"\u003cp\u003eLegend not included with this version.\u003c/p\u003e","description":"","filename":"1.png","url":"https://assets-eu.researchsquare.com/files/rs-6158637/v1/31189537c08293b862efaa2e.png"},{"id":77854907,"identity":"98f7f1c1-2200-4480-8ffa-4933fcba25e4","added_by":"auto","created_at":"2025-03-06 07:36:59","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":522442,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-6158637/v1/0f4008ef-7124-411f-b74c-f035ad23bb0f.pdf"},{"id":77853528,"identity":"10854c65-db97-4e8a-ae1f-c7df10051c8f","added_by":"auto","created_at":"2025-03-06 07:21:05","extension":"docx","order_by":1,"title":"","display":"","copyAsset":false,"role":"supplement","size":827288,"visible":true,"origin":"","legend":"","description":"","filename":"SPECTRALDATAWOOIIXANTHONE.docx","url":"https://assets-eu.researchsquare.com/files/rs-6158637/v1/8ff1d4b85d04771a87f6e6ac.docx"}],"financialInterests":"The authors declare no competing interests.","formattedTitle":"\u003cp\u003eWoodiixanthone A from the Stem Bark of \u003cem\u003eCalophyllum woodii\u003c/em\u003e P. F. Stevens\u003c/p\u003e","fulltext":[{"header":"1. Introduction","content":"\u003cp\u003eThe genus \u003cem\u003eCalophyllum\u003c/em\u003e, a large group of trees that are members of the Calophyllaceae family comprises approximately 180\u0026ndash;200 species, some of which are indigenous to Sarawak, Malaysia's tropical rainforest (Lim et al., 2019). This woody tree exclusively grows on sandy sea beaches along the Western Ghats of India and other parts of the world such as Tropical Asia, East Africa, Malaysia, Vietnam, Indonesia, Philippines, Australia, and several Pacific islands (Pawar \u0026amp; Patil, 2019). The phytochemical study of \u003cem\u003eCalophyllum\u003c/em\u003e has revealed that it is a rich source of bioactive secondary metabolites, and several species of the genus have been explored for their phytochemical content (Gupta \u0026amp; Gupta, 2020). These include xanthones, flavonoids, acylphloroglucinols, terpenoids, and chromanones, which have also been reported to be present in plants within this genus. (Ogasawara et al., 2022). The plant has a long history of traditional and therapeutic uses, and it has been reported to have several medicinally important bioactive principles including anti_HIV, anti-microbial, cytotoxic activities, antimalarial and antioxidant properties (Daud et al., 2021).\u003c/p\u003e \u003cp\u003e \u003cem\u003eC. woodii\u003c/em\u003e, also known as \u0026lsquo;Billian\u0026rsquo; or \u0026lsquo;Kayu Billian\u0026rsquo; is a medium-sized to large tree native belonging to the Myrtaceae family, primarily found in the wet tropical biome of North and Northwest Borneo. This plant has gained attention for its potential medicinal uses. However, research on the biological and phytochemical properties of \u003cem\u003eC. woodii\u003c/em\u003e has yielded few scientific reports up to recently. As part of an ongoing phytochemical study on Sarawak \u003cem\u003eCalophyllum\u003c/em\u003e plants, we are pleased to report the structural elucidation and isolation of a new pyranocoumarin, named woodiixanthone A (\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e) and identified as 5,7-dihydroxy-8-(3-hydroxy-2-methylbutanoyl)-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H-chromen-2-one.\u003c/p\u003e"},{"header":"2. Result and Discussion","content":"\u003cp\u003ePhytochemical study on the hexane extract of \u003cem\u003eC. woodii\u003c/em\u003e yielded a new pyranocoumarin, woodiixanthone (\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e) along with seven known compounds, isocalanone (\u003cspan citationid=\"CR2\" class=\"CitationRef\"\u003e2\u003c/span\u003e), calanone (\u003cspan citationid=\"CR3\" class=\"CitationRef\"\u003e3\u003c/span\u003e), euxanthone (\u003cspan citationid=\"CR4\" class=\"CitationRef\"\u003e4\u003c/span\u003e), teysmanone A (\u003cspan citationid=\"CR5\" class=\"CitationRef\"\u003e5\u003c/span\u003e), tovopyrifolin C (\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e) 6-deoxyjacaruebin (\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e) and friedelin (\u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e). Woodiixanthone (\u003cspan citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e) was isolated as pale-yellow crystal, displayed m/z of 422.17 corresponding to the molecular formula of C\u003csub\u003e25\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eO\u003csub\u003e6\u003c/sub\u003e. The \u003csup\u003e13\u003c/sup\u003eC NMR spectrum of 1 showed signals corresponding to 25 carbons, including 4 methyl, 1 methine, and 7 quaternary carbons.\u003c/p\u003e \u003cp\u003eAnalysis on the \u003csup\u003e1\u003c/sup\u003eH NMR spectrum showed a chelated hydroxyl group (O-H) at the most downfield of the region in the form of singlet at δ\u003csub\u003eH\u003c/sub\u003e 13.28 was assigned as 7-OH attached to C-7. A singlet assigned as H-3 showed a lone aromatic proton at δ\u003csub\u003eH\u003c/sub\u003e 5.93 (1H, s) attached to the nucleus of the coumarin. A triplet at δ\u003csub\u003eH\u003c/sub\u003e 5.28 (1 H, t, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.4 Hz) and a doublet at δ\u003csub\u003eH\u003c/sub\u003e 3.47 (2H, \u003cem\u003ed\u003c/em\u003e, J\u0026thinsp;=\u0026thinsp;7.4 Hz) displayed the existence of a prenyl group in the structure. In addition, compound 1 demonstrated 4-phenyl signals with two pairs of multiplets at δ\u003csub\u003eH\u003c/sub\u003e 7.42 were assigned as H-3\u0026rsquo;, H-4\u0026rsquo; and H-5\u0026rsquo; and the other multiplet at δ\u003csub\u003eH\u003c/sub\u003e 7.33 for the aromatic proton H-2\u0026rsquo; and H-6\u0026rsquo;. Furthermore, the existence of 8-(3-hydroxy-2-methylbutanoyl) signals was proved at δ\u003csub\u003eH\u003c/sub\u003e 4.49 (1H, \u003cem\u003em\u003c/em\u003e, H-3\u0026rsquo;\u0026rsquo;\u0026rsquo;), δ\u003csub\u003eH\u003c/sub\u003e 1.22 (3H, \u003cem\u003ed\u003c/em\u003e, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;6.3 Hz, H-4\u0026rsquo;\u0026rsquo;\u0026rsquo;) and δ\u003csub\u003eH\u003c/sub\u003e 1.61 (3H, \u003cem\u003ed, J\u003c/em\u003e\u0026thinsp;=\u0026thinsp;6.3 Hz, H-5\u0026rsquo;\u0026rsquo;\u0026rsquo;).\u003c/p\u003e \u003cp\u003eThe isolated compound was deduced to be 5,7-dihydroxy-8-(3-hydroxy-2-methylbutanoyl)-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H-chromen-2-one. The identified compound was isolated for the first time from \u003cem\u003eC. woodii\u003c/em\u003e.\u003c/p\u003e \u003cp\u003eThe \u003csup\u003e1\u003c/sup\u003eH and \u003csup\u003e13\u003c/sup\u003eC NMR spectral data of woodiixanthone A in acetone-d\u003csup\u003e6\u003c/sup\u003e\u003c/p\u003e \u003cp\u003e \u003cdiv class=\"gridtable\"\u003e\u003ctable float=\"No\" id=\"Taba\" border=\"1\"\u003e \u003ccolgroup cols=\"5\"\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c1\" colnum=\"1\"\u003e\u003c/div\u003e \u003cdiv align=\"char\" char=\".\" class=\"colspec\" colname=\"c2\" colnum=\"2\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c3\" colnum=\"3\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c4\" colnum=\"4\"\u003e\u003c/div\u003e \u003cdiv align=\"left\" class=\"colspec\" colname=\"c5\" colnum=\"5\"\u003e\u003c/div\u003e \u003cthead\u003e \u003ctr\u003e \u003cth align=\"left\" colname=\"c1\"\u003e \u003cp\u003ePosition\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c2\"\u003e \u003cp\u003e\u003csup\u003ed\u003c/sup\u003eC (ppm)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c3\"\u003e \u003cp\u003e\u003csup\u003ed\u003c/sup\u003eH (ppm)\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c4\"\u003e \u003cp\u003eHMBC\u003c/p\u003e \u003c/th\u003e \u003cth align=\"left\" colname=\"c5\"\u003e \u003cp\u003eCOSY\u003c/p\u003e \u003c/th\u003e \u003c/tr\u003e \u003c/thead\u003e \u003ctbody\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e158.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e112.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e5.93 (1H, \u003cem\u003es\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-2, C-4a, C-1ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e155.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4a\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e101.9\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e160.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e108.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e160.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e103.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e8a\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e159.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e139.1\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e127.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7.42 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-4ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-3ʹ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e128.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7.33 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-1ʹ, C-2ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-2ʹ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e127.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7.42 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e128.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7.42 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-1ʹ, C-6ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-6ʹ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e6ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e127.3\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e7.42 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-4ʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-5 ʹ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e21.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e3.47 (2H, \u003cem\u003ed\u003c/em\u003e, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.4 Hz)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e121.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e5.28 (1H, \u003cem\u003et\u003c/em\u003e, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;7.4 Hz)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-3ʺ, C-4ʺ, C-5ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-3ʺ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e131.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-2ʺ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e17.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.87 (3H, \u003cem\u003es\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-5 ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e25.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.69 (3H, \u003cem\u003es\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-4 ʺ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e1ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e201.0\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-3ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e2ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e45.6\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e2.85 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-1ʺʹ, C-3ʺʹ, C-4ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-3ʺʹ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e3ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e79.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e4.49 (1H, \u003cem\u003em\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-1ʺʹ, C-4ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e4ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e9.2\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.22 (3H, \u003cem\u003ed\u003c/em\u003e, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;6.3 Hz)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-1ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e\u0026nbsp;\u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e5ʺʹ\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e18.8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e1.61 (3H, \u003cem\u003ed\u003c/em\u003e, \u003cem\u003eJ\u003c/em\u003e\u0026thinsp;=\u0026thinsp;6.3 Hz)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e\u0026nbsp;\u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-5ʺʹ\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003ctr\u003e \u003ctd align=\"left\" colname=\"c1\"\u003e \u003cp\u003e7-OH\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"char\" char=\".\" colname=\"c2\"\u003e \u003cp\u003e160.4\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c3\"\u003e \u003cp\u003e13.28 (1H, \u003cem\u003es\u003c/em\u003e)\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c4\"\u003e \u003cp\u003eC-8\u003c/p\u003e \u003c/td\u003e \u003ctd align=\"left\" colname=\"c5\"\u003e \u003cp\u003eH-8\u003c/p\u003e \u003c/td\u003e \u003c/tr\u003e \u003c/tbody\u003e \u003c/colgroup\u003e \u003c/table\u003e\u003c/div\u003e \u003c/p\u003e"},{"header":"3. Experiment Section","content":"\u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003e3.1 General\u003c/h2\u003e \u003cp\u003eThe BRUKER AVANCE III 400 MHz spectrometer (Karlsruhe, Germany) with 400 MHz and 100 MHz instrument operating system, respectively, were used to obtain the \u003csup\u003e1\u003c/sup\u003eH NMR and \u003csup\u003e13\u003c/sup\u003eC NMR spectra. In the corresponding analysis, deuterated acetone (acetone-d\u003csub\u003e6\u003c/sub\u003e) and deuterated chloroform (CDCl\u003csub\u003e3\u003c/sub\u003e) were employed\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003e3.2 Plant Material\u003c/h2\u003e \u003cp\u003eThe stem bark of \u003cem\u003eC. woodii\u003c/em\u003e were obtained from the herbarium vouchers located at Universiti Teknologi MARA (UiTM), Kampus Samarahan 2, Sarawak. The stem barks were air-dried at room temperature and were ground into powder form prior to the extraction process.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec6\" class=\"Section2\"\u003e \u003ch2\u003e3.3 Extraction and isolation\u003c/h2\u003e \u003cp\u003eThe stem bark of \u003cem\u003eC. woodii\u003c/em\u003e was dried and ground to fine powder producing 1.2 kg samples. The samples were macerated with \u003cem\u003en-\u003c/em\u003ehexane and allowed to stand for 14 days at room temperature. The macerated sample was filtered, and n-hexane was added again to the stem bark after the first filtration was collected. The samples were then evaporated by using a rotary evaporator to dry under reduced pressure at 40\u0026deg;C. The yield of 10.3447 g \u003cem\u003en\u003c/em\u003e-hexane extracts. The crude extract was then subjected to silica gel column chromatography (CC) using n-hexane as the initial solvent, followed by elution with mixtures of n-hexane and EtOAc (ranging from 90:10 to 0:100), resulting in 13 fractions (CWH1-13). Fraction CWH5-6 was further isolated using Sephadex LH-20 CC and eluted with 100% MeOH to obtain 7 subfractions (CWH56A-G). Purification of subfraction CWH56H-G using chromatatron elution with 100% chloroform yielded 2.5 mg of woodiixanthone A in the form of pale yellow crystals.\u003c/p\u003e \u003c/div\u003e"},{"header":"4. Conclusion","content":"\u003cp\u003eThe isolation of the n-hexane extract from \u003cem\u003eC. woodii\u003c/em\u003e stem bark has led to the discovery of a new compound, woodiixanthone A. The unique structure of the compound makes it a promising subject for further investigation\u0026nbsp;\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e\u003cstrong\u003eDeclarations Conflict of Interest:\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\n\u003cp\u003eThe authors declare no conflict of interest.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAuthor Contributions:\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eSNH has contributed to writing - original draft preparation resources, and VJYM conceptualization writing- review, supervision, and funding acquisition.\u003c/p\u003e\n\u003cp\u003e\u003cstrong\u003eAcknowledgments:\u003c/strong\u003e\u003c/p\u003e\n\u003cp\u003eThe authors would like to acknowledge the UiTM Sarawak for financial assistance and support given throughout the research conducted on the genus \u003cem\u003eCalophyllum\u003c/em\u003e by VJYM and SNH.\u0026nbsp;\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\n \u003cli\u003eAminudin, N. I., Ahmad, F., \u0026amp; Taher, M. (2019). Antibacterial and antioxidant activities of extracts from \u003cem\u003eCalophyllum ferrugineum\u003c/em\u003e and \u003cem\u003eCalophyllum incrassatum\u003c/em\u003e. \u003cem\u003eMalaysian Journal of Analytical Sciences, 23\u003c/em\u003e(4), 637-647.\u003c/li\u003e\n \u003cli\u003eCassien, M., Mercier, A., Th\u0026eacute;tiot-Laurent, S., Culcasi, M., Ricquebourg, E., Asteian, A., ... \u0026amp; Pietri, S. (2021). Improving the antioxidant properties of \u003cem\u003eCalophyllum inophyllum\u003c/em\u003e seed oil from French Polynesia: Development and biological applications of resinous ethanol-soluble extracts.\u0026nbsp;\u003cem\u003eAntioxidants, 10\u003c/em\u003e(2), 199.\u003c/li\u003e\n \u003cli\u003eDaud, S., Karunakaran, T., Santhanam, R., Nagaratnam, S. R., Jong, V. Y. M., \u0026amp; Ee, G. C. L. (2021). Cytotoxicity and nitric oxide inhibitory activities of xanthones isolated from \u003cem\u003eCalophyllum hosei\u003c/em\u003e Ridl. \u003cem\u003eNatural Product Research, 35\u003c/em\u003e(24), 6067-6072.\u003c/li\u003e\n \u003cli\u003ede Sousa, N. F., Scotti, L., de Moura, \u0026Eacute;. P., dos Santos Maia, M., Rodrigues, G. C. S., de Medeiros, H. I. R., ... \u0026amp; Scotti, M. T. (2022). Computer-aided drug design methodologies with natural products in the drug research against Alzheimer\u0026rsquo;s disease. \u003cem\u003eCurrent Neuropharmacology, 20\u003c/em\u003e(5), 857.\u003c/li\u003e\n \u003cli\u003eDziało, M., Mierziak, J., Korzun, U., Preisner, M., Szopa, J., \u0026amp; Kulma, A. (2016). The potential of plant phenolics in prevention and therapy of skin disorders. \u003cem\u003eInternational Journal of Molecular Sciences, 17\u003c/em\u003e(2), 160.\u003c/li\u003e\n \u003cli\u003eGupta, S., \u0026amp; Gupta, P. (2020). The genus \u003cem\u003eCalophyllum\u003c/em\u003e: Review of ethnomedicinal uses, phytochemistry, and pharmacology. In \u003cem\u003eBioactive natural products in drug discovery\u003c/em\u003e (pp. 215-242).\u003c/li\u003e\n \u003cli\u003eKarunakaran, T., Firouz, N. S., Santhanam, R., \u0026amp; Jong, V. Y. M. (2022). Phytochemicals from \u003cem\u003eCalophyllum macrocarpum\u003c/em\u003e Hook. f. and its cytotoxic activities. \u003cem\u003eNatural Product Research, 36\u003c/em\u003e(2), 654-659.\u003c/li\u003e\n \u003cli\u003eLim, C. K., Subramaniam, H., Say, Y. H., Jong, V. Y. M., Khaledi, H., \u0026amp; Chee, C. F. (2015). A new chromanone acid from the stem bark of \u003cem\u003eCalophyllum teysmannii\u003c/em\u003e. \u003cem\u003eNatural Product Research, 29\u003c/em\u003e(21), 1970-1977.\u003c/li\u003e\n \u003cli\u003eLizazman, M. A., Jong, V. Y. M., Chua, P., Lim, W. K., \u0026amp; Karunakaran, T. (2023). Phytochemicals from \u003cem\u003eCalophyllum canum\u003c/em\u003e Hook f. ex T. Anderson and their neuroprotective effects. \u003cem\u003eNatural Product Research, 37\u003c/em\u003e(12), 2043-2048.\u003c/li\u003e\n \u003cli\u003eOgasawara, A., Noguchi, R., Shigi, T., Nugroho, A. E., Hirasawa, Y., Kaneda, T., ... \u0026amp; Morita, H. (2022). Caloforines A\u0026ndash;G, coumarins from the bark of \u003cem\u003eCalophyllum scriblitifolium\u003c/em\u003e. \u003cem\u003eJournal of Natural Medicines, 76\u003c/em\u003e(3), 645-657.\u003c/li\u003e\n \u003cli\u003ePawar, K. D., \u0026amp; Patil, R. V. (2020). Phytochemicals of \u003cem\u003eCalophyllum inophyllum\u003c/em\u003e. In H. Murthy \u0026amp; V. Bapat (Eds.), \u003cem\u003eBioactive compounds in underutilized fruits and nuts\u003c/em\u003e (pp. [insert page range if available]). Reference Series in Phytochemistry. Springer, Cham.\u003c/li\u003e\n\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":true,"hideJournal":true,"highlight":"","institution":"Universiti Teknologi MARA","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"woodiixanthone A, Calophyllum woodii, NMR characterization","lastPublishedDoi":"10.21203/rs.3.rs-6158637/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-6158637/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eA new pyranocoumarin, wooiixanthone A (1), along with seven known compounds, isocalanone (2), calanone (3), euxanthone (4), teysmanone A (5), tovopyrifolin C (6) 6-deoxyjacaruebin (7) and friedelin (8) were isolated from the stem bark of \u003cem\u003eCalophyllum woodie \u003c/em\u003eP. F. Stevens collected from Sarawak. The structure of (1) was confirmed using 1D NMR, FTIR, and MS spectra.\u003c/p\u003e","manuscriptTitle":"Woodiixanthone A from the Stem Bark of Calophyllum woodii P. F. Stevens","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2025-03-06 07:20:53","doi":"10.21203/rs.3.rs-6158637/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"2552ded7-c4ef-40b7-90ee-fab2505b1655","owner":[],"postedDate":"March 6th, 2025","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[{"id":45212721,"name":"Natural Product Chemistry"}],"tags":[],"updatedAt":"2025-03-06T07:20:53+00:00","versionOfRecord":[],"versionCreatedAt":"2025-03-06 07:20:53","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-6158637","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-6158637","identity":"rs-6158637","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}