Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov

Suda Sananboonudom; Atchara Kaewnoi; Wilart Pompimon; Samroeng Narakaew; Suwadee Jiajaroen; Kittipong Chainok; Narong Nuntasaen; Kanoknetr Suksen; Arthit Chairoungdua; Jitra Limthongkul; Chanita Naparswad; Suttiporn Pikulthong; Puttinan Meepowpan; Boonthawan Wingwon; Nichapa Charoenphakinrattana; Phansuang Udomputtimekakul

doi:10.1186/s12906-023-03963-4

Study on the absolute configuration and biological activity of rotenoids from the leaves and twigs of Millettia pyrrhocarpa Mattapha, Forest & Hawkins, sp. Nov

BMC Complement Med Ther. 2023 May 4;23(1):147. doi: 10.1186/s12906-023-03963-4.

Authors

Suda Sananboonudom¹, Atchara Kaewnoi², Wilart Pompimon¹, Samroeng Narakaew¹, Suwadee Jiajaroen³, Kittipong Chainok³, Narong Nuntasaen⁴, Kanoknetr Suksen⁵, Arthit Chairoungdua^{5

6

7}, Jitra Limthongkul⁸, Chanita Naparswad⁸, Suttiporn Pikulthong⁹, Puttinan Meepowpan¹⁰, Boonthawan Wingwon¹¹, Nichapa Charoenphakinrattana¹², Phansuang Udomputtimekakul¹³

Affiliations

¹ Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, Lampang, 52100, Thailand.
² Department of Thai Traditionnal Medicine, Faculty of Science and Technology, Bansomdejchaopraya Rajabhat University, Bangkok, 10600, Thailand.
³ Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TUMcMa), Faculty of Science and Technology, Thammasat University, Pathum Thani, 12121, Thailand.
⁴ Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Mahidol University, Bangkok, 10400, Thailand.
⁵ Department of Physiology, Faculty of Science, Mahidol University, Bangkok, 10600, Thailand.
⁶ Excellent Center for Drug Discovery (ECDD), Mahidol University, Bangkok, 10600, Thailand.
⁷ Toxicology Graduate Program, Faculty of Science, Mahidol University, Bangkok, 10600, Thailand.
⁸ Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, 10600, Thailand.
⁹ Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, 10600, Thailand.
¹⁰ Department of Chemistry, and Center for Innovation in Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50300, Thailand.
¹¹ Department of Management Science, Faculty of Management Science, Lampang Rajabhat University, Lampang, 52100, Thailand.
¹² Life Group International, Khaochangum Subdistrict, Photharam District, Ratchaburi, 70120, Thailand.
¹³ Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, Lampang, 52100, Thailand. phansuang@g.lpru.ac.th.

Abstract

Background: M. pyrrhocarpa is a new plant in the Fabaceae: Faboideae family that is found in Thailand. A literature search revealed that the Milletia genus is rich in bioactive compounds possessing a wide range of biological activities. In this study, we aimed to isolate novel bioactive compounds and to study their bioactivities.

Methods: The hexane, ethyl acetate, and methanol extracts from the leaves and twigs of M. pyrrhocarpa were isolated and purified using chromatography techniques. These extracts and pure compounds were tested in vitro for their inhibitory activities against nine strains of bacteria, as well as their anti-HIV-1 virus activity and cytotoxicity against eight cancer cell lines.

Results: Three rotenoids, named 6aS, 12aS, 12S-elliptinol (1), 6aS, 12aS, 12S-munduserol (2), dehydromunduserone (3), and crude extracts were evaluated for antibacterial, anti-HIV, and cytotoxic activities. It was found that compounds 1-3 inhibited the growth of nine strains of bacteria, and the best MIC/MBC values were obtained at 3/ > 3 mg/mL. The hexane extract showed anti-HIV-1 RT with the highest %inhibition at 81.27 at 200 mg/mL, while 6aS, 12aS, 12S-elliptinol (1) reduced syncytium formation in 1A2 cells with a maximum EC₅₀ value of 4.48 μM. Furthermore, 6aS, 12aS, 12S-elliptinol (1) showed cytotoxicity against A549 and Hep G2 cells with maximum ED₅₀ values of 2.27 and 3.94 μg/mL.

Conclusion: This study led to the isolation of constituents with potential for medicinal application, providing compounds (1-3) as lead compounds against nine strains of bacteria. The hexane extract showed the highest %inhibition of HIV-1 virus, Compound 1 showed the best EC₅₀ in reducing syncytium formation in 1A2 cells, and it also showed the best ED₅₀ against human lung adenocarcinoma (A549) and human hepatocellular carcinoma (Hep G2). The isolated compounds from M. pyrrhocarpa offered significant potential for future medicinal application studies.

Keywords: Anti-HIV activity; Antibacterial activity; Cytotoxicity; Fabaceae: Faboideae; Millettia pyrrhocarpa; Rotenoids.

MeSH terms

Bacteria
Hexanes
Humans
Millettia*
Plant Extracts* / chemistry
Plant Extracts* / pharmacology

Substances

elliptinol
Plant Extracts
n-hexane
Hexanes