Calabanones A-H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells

doi:10.1007/s13659-026-00603-5

Natural Products and Bioprospecting ›› 2026, Vol. 16 ›› Issue (3): 43-43.DOI: 10.1007/s13659-026-00603-5

• ORIGINAL ARTICLES • Previous Articles

Calabanones A-H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells

Sutin Kaennakam¹, Fadjar Mulya², Manussada Ratanasak³, Kitiya Rassamee⁴, Pongpun Siripong⁴, Yasuteru Shigeta³, Preecha Phuwapraisirisan⁵, Edwin R. Sukandar⁶

1. Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand;
2. Nanotechnology Engineering, Faculty of Advanced Technology and Multidiscipline, Universitas Airlangga, Surabaya 60115, Indonesia;
3. Center for Computational Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan;
4. Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, 10400, Thailand;
5. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;
6. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, Bandung 40132, Indonesia

Received:2025-10-30 Online:2026-06-24
Contact: Sutin Kaennakam,E-mail:sutin.k@sci.kmutnb.ac.th;Edwin R. Sukandar,E-mail:esukandar@itb.ac.id
Supported by:
This research was funded by National Science, Research and Innovation Fund (NSRF), and King Mongkut’s University of Technology North Bangkok (Project No. KMUTNB-FF-68-B-40). E.R.S acknowledges the funding by the Indonesian Endowment Fund for Education (LPDP) on behalf of the Indonesian Ministry of Higher Education, Science and Technology and managed under the EQUITY Program (Contract No. 4298/B3/DT.03.08/2025). M.R. and Y.S. acknowledge the MEXT Promotion of the Development of a Joint Usage/Research System Project: Coalition of Universities for Research Excellence (CURE) Program [Grant Number JPMXP1323015474] and the Multidisciplinary Cooperative Research Program at the Center for Computational Sciences, University of Tsukuba. Some of the computations were performed using computer facilities at the Research Center for Computational Science, Okazaki, Japan (Project: 25-IMS-C103).

Calabanones A-H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells

Sutin Kaennakam¹, Fadjar Mulya², Manussada Ratanasak³, Kitiya Rassamee⁴, Pongpun Siripong⁴, Yasuteru Shigeta³, Preecha Phuwapraisirisan⁵, Edwin R. Sukandar⁶

1. Department of Agro-Industrial, Food, and Environmental Technology, Faculty of Applied Science, King Mongkut's University of Technology North Bangkok (KMUTNB), Bangkok 10800, Thailand;
2. Nanotechnology Engineering, Faculty of Advanced Technology and Multidiscipline, Universitas Airlangga, Surabaya 60115, Indonesia;
3. Center for Computational Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8577, Japan;
4. Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, 10400, Thailand;
5. Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand;
6. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, Bandung 40132, Indonesia

通讯作者: Sutin Kaennakam,E-mail:sutin.k@sci.kmutnb.ac.th;Edwin R. Sukandar,E-mail:esukandar@itb.ac.id
基金资助:
This research was funded by National Science, Research and Innovation Fund (NSRF), and King Mongkut’s University of Technology North Bangkok (Project No. KMUTNB-FF-68-B-40). E.R.S acknowledges the funding by the Indonesian Endowment Fund for Education (LPDP) on behalf of the Indonesian Ministry of Higher Education, Science and Technology and managed under the EQUITY Program (Contract No. 4298/B3/DT.03.08/2025). M.R. and Y.S. acknowledge the MEXT Promotion of the Development of a Joint Usage/Research System Project: Coalition of Universities for Research Excellence (CURE) Program [Grant Number JPMXP1323015474] and the Multidisciplinary Cooperative Research Program at the Center for Computational Sciences, University of Tsukuba. Some of the computations were performed using computer facilities at the Research Center for Computational Science, Okazaki, Japan (Project: 25-IMS-C103).

Abstract

Abstract: The genus Calophyllum (Calophyllaceae), distributed mainly in tropical regions, is rich in chromanone derivatives with diverse molecular structures that exhibit potential antimicrobial and anticancer effects. Phytochemical investigation of the stem bark of C. calaba collected in Thailand led to the discovery of eight previously undescribed chromanones, calabanones A-H (1-8), and two known analogs, (-)-isocalomembranone P (9) and (-)-calomembranone P (10). The chemical structures of undescribed compounds were elucidated using spectroscopic analyses, particularly NMR and HRESIMS, while their absolute configurations were determined through ECD and NMR calculations combined with DP4+ probability analysis. Compounds 7 and 8 were identified as chromanone-steroid hybrids linked via an ester bond, representing the first report of such structures in plants. Cytotoxic evaluation of the isolated specialized metabolites revealed that compounds 6 and 9 displayed moderate activity against KB and HeLa S3 cancer cell lines, with IC₅₀ values ranging from 12.71 to 25.50 μM, while compounds 3-5 selectively inhibited the growth of KB cells, with IC₅₀ values in the range of 18.77-27.06 μM.

Key words: Calophyllum calaba, Calophyllaceae, Chromanone, Calabanone, Cytotoxic

摘要： The genus Calophyllum (Calophyllaceae), distributed mainly in tropical regions, is rich in chromanone derivatives with diverse molecular structures that exhibit potential antimicrobial and anticancer effects. Phytochemical investigation of the stem bark of C. calaba collected in Thailand led to the discovery of eight previously undescribed chromanones, calabanones A-H (1-8), and two known analogs, (-)-isocalomembranone P (9) and (-)-calomembranone P (10). The chemical structures of undescribed compounds were elucidated using spectroscopic analyses, particularly NMR and HRESIMS, while their absolute configurations were determined through ECD and NMR calculations combined with DP4+ probability analysis. Compounds 7 and 8 were identified as chromanone-steroid hybrids linked via an ester bond, representing the first report of such structures in plants. Cytotoxic evaluation of the isolated specialized metabolites revealed that compounds 6 and 9 displayed moderate activity against KB and HeLa S3 cancer cell lines, with IC₅₀ values ranging from 12.71 to 25.50 μM, while compounds 3-5 selectively inhibited the growth of KB cells, with IC₅₀ values in the range of 18.77-27.06 μM.

关键词: Calophyllum calaba, Calophyllaceae, Chromanone, Calabanone, Cytotoxic

Sutin Kaennakam, Fadjar Mulya, Manussada Ratanasak, Kitiya Rassamee, Pongpun Siripong, Yasuteru Shigeta, Preecha Phuwapraisirisan, Edwin R. Sukandar. Calabanones A-H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells[J]. Natural Products and Bioprospecting, 2026, 16(3): 43-43.

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Calabanones A-H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells

Calabanones A-H, chromanone derivatives from the stem bark of Calophyllum calaba and their cytotoxic activities against cancer cells

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