Dataset Information

Xuetonglactones A-F: Highly Oxidized Lanostane and Cycloartane Triterpenoids From Kadsura heteroclita Roxb. Craib.

ABSTRACT: Xuetonglactones A-F (1-6), six unreported highly oxidized lanostane- and cycloartane-type triterpenoids along with 22 known scaffolds (7-28) were isolated from the stems of Kadsura heteroclita (Roxb.) Craib. Compared with previous congeners, xuetonglactone A (1), possesses an unprecedented 20,21-?-epoxide, and xuetonglactone D (4) features an unusual 19-?-hydroperoxyl moiety. The structures and the absolute configurations of the compounds were established by extensive one- and two-dimensional NMR, and electronic circular dichroism (ECD) spectroscopic analysis, with those of 1 and 5 confirmed by single-crystal X-ray diffraction technique. Compounds 1 and 2 exhibited inhibition of iNOS activity in LPS-induced macrophages with IC50 values of 22.0, and 17.0 ?g/mL, respectively. While compounds 6, 7, 8, and 24 showed potent cytotoxic activities against human cervical cancer cell lines (HeLa) with the IC50 values of 4.0, 5.8, 5.0, and 6.4 ?M, and against human gastric cancer cells (BGC 823) with the IC50 values of 2.0, 5.0, 2.5, and 2.0 ?M, respectively. Moreover, plausible biogenetic pathways of (1-6) were also proposed.

SUBMITTER: Shehla N

PROVIDER: S-EPMC6990113 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Xuetonglactones A-F: Highly Oxidized Lanostane and Cycloartane Triterpenoids From Kadsura heteroclita Roxb. Craib.

Shehla Nuzhat N Li Bin B Cao Liang L Zhao Jianping J Jian Yuqing Y Daniyal Muhammad M Wahab Atia-Tul AT Khan Ikhlas A IA Liao Duan-Fang DF Rahman Atta-Ur AU Choudhary M Iqbal MI Wang Wei W

Frontiers in chemistry 20200121

Xuetonglactones A-F (1-6), six unreported highly oxidized lanostane- and cycloartane-type triterpenoids along with 22 known scaffolds (7-28) were isolated from the stems of Kadsura heteroclita (Roxb.) Craib. Compared with previous congeners, xuetonglactone A (1), possesses an unprecedented 20,21-α-epoxide, and xuetonglactone D (4) features an unusual 19-α-hydroperoxyl moiety. The structures and the absolute configurations of the compounds were est ...[more]

PMID: 32039154

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Project description:Kadsura spp. in the Schisandraceae family are woody vine plants, which produce edible red fruits that are rich in nutrients and antioxidant activities. Despite their valuable food applications, Kadsura spp. are only able to grow naturally in the forest, and reproduction handled by botanists is still in progress with a very low growth rate. Subsequently, Kadsura spp. were listed as endangered species by the International Union for Conservation of Nature and Natural Resources (IUCN) in 2011. Two different Kadsura spp., including Kadsura coccinea (Lem.) A.C. Sm. and Kadsura heteroclita (Roxb.) Craib, are mostly found in northern Thailand. These rare, wild fruits are unrecognizable to outsiders, and there have only been limited investigations into its biological properties. This study, therefore, aimed to comparatively investigate the phenolic profiles, antioxidant activities, and inhibitory activities against the key enzymes involved in diabetes (?-glucosidase and ?-amylase) and Alzheimer's disease (acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and beta-secretase 1 (BACE-1)) in different fruit parts (exocarp, mesocarp (edible part), seed, and core) of Kadsura coccinea (Lem.) A.C. Sm. and Kadsura heteroclita (Roxb.) Craib. The results suggested that Kadsura spp. extracts were rich in flavonol (quercetin), flavanone (naringenin), anthocyanidins (cyanidin and delphinidin), and anthocyanins (cyanidin 3-O-glucoside (kuromanin), cyanidin 3-O-galactoside (ideain), cyanidin 3-O-rutinoside (keracyanin), and cyanidin 3,5-di-O-glucoside (cyanin)). These flavonoids were found to be responsible for the high antioxidant activities and key enzyme inhibitions detected in Kadsura spp. extracts. The findings of the present study can support further development of Kadsura spp. as a potential source of phenolics and anti-oxidative agents with health benefits against diabetes and Alzheimer's disease. Besides, exocarp and the core of Kadsura spp. exhibited higher phenolic contents, antioxidant activities, and key enzyme inhibitory activities compared to the mesocarp and seeds, respectively. This information can promote the use of fruit parts other than the edible mesocarp for future food applications using Kadsura spp. rather than these being wasted.

Dataset Information

Xuetonglactones A-F: Highly Oxidized Lanostane and Cycloartane Triterpenoids From Kadsura heteroclita Roxb. Craib.

Publications

Xuetonglactones A-F: Highly Oxidized Lanostane and Cycloartane Triterpenoids From <i>Kadsura heteroclita</i> Roxb. Craib.

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