Bioactive Lignan Constituents from the Twigs of &lt;i&gt;Lindera glauca&lt;/i&gt;

Kim, Ki‐Hyun; Moon, Eunjung; Ha, Sang Keun; Suh, Won Se; Kim, Ho Kyung; Kim, Sun Yeou; Choi, Sang Un; Lee, Kang Ro

doi:10.1248/cpb.c14-00381

Cited by 17 publications

(7 citation statements)

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“…Its fruits are rich in fatty acids and aromatic oils, and they contain terpenoids, flavonoids, and alkaloids, which are used for various applications in traditional medicine. Fruits are also used as raw materials to produce medicines, lubricants, and biochemical products (Zheng, 1983;Wang et al, 1994;Kim et al, 2014;Suh et al, 2015;Qi et al, 2016). Some root extract components, like N-methyllaurotetanine, exhibit significant anti-tumor metastatic activity (Kim et al, 2014;Suh et al, 2015) and some volatile oils from the leaves are used in the industrial production pf spices (Qi et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

“…Fruits are also used as raw materials to produce medicines, lubricants, and biochemical products (Zheng, 1983;Wang et al, 1994;Kim et al, 2014;Suh et al, 2015;Qi et al, 2016). Some root extract components, like N-methyllaurotetanine, exhibit significant anti-tumor metastatic activity (Kim et al, 2014;Suh et al, 2015) and some volatile oils from the leaves are used in the industrial production pf spices (Qi et al, 2016). Additionally, the L. glauca species has emerged as a novel potential source of biodiesel in China due to the high quality and quantity of its fruit oil (Lin et al, 2017;Xiong, Dong & Zhang, 2018).…”

Section: Introductionmentioning

confidence: 99%

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Population genetic structure and variability inLindera glauca(Lauraceae) indicates low levels of genetic diversity and skewed sex ratios in natural populations in mainland China

Xiong

Zhang

Dong

et al. 2020

PeerJ

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Lindera glauca (Lauraceae) is a tree of economic and ecological significance that reproduces sexually and asexually via apomictic seeds. It is widely distributed in the low-altitude montane forests of East Asia. Despite the potential implications of a mixed reproductive system in terms of genetic diversity, few studies have focused on this aspect. In this study, the genetic structure of wild populations of L. glauca was investigated via genetic analyses. Overall, 13 nuclear microsatellites (nSSRs) and five chloroplast microsatellites (cpSSRs) were used to genotype 300 individual plants, taken from 20 wild populations (a small sample size in some wild populations is due to the limitation of its specific reproduction, leading to certain limitations in the results of this study) and two cultivated populations ranging across nearly the entire natural distribution of mainland China. The populations exhibited low levels of genetic diversity (nSSR: AR = 1.75, Ho = 0.32, He = 0.36; cpSSR: Nb = 2.01, Hrs = 0.40), and no significant effect of isolation by distance between populations existed, regardless of marker type (nSSR: R2 = 0.0401, P = 0.068; cpSSR: R2 = 0.033, P = 0.091). Haplotype networks showed complex relationships among populations, and the H12 haplotype was predominant in most populations. Analyses of molecular variance obtained with nuclear markers (Fsc = 0.293, FST = 0.362) and chloroplast markers (Fsc = 0.299, FST = 0.312) were similar. The migration ratio of pollen flow versus seed flow in this study was negative (r = −1.149). Results suggest that weak barriers of dispersal between populations and/or the similarity of founders shared between neighbors and distant populations are indicative of the gene flow between populations more likely involving seeds. Wild L. glauca in mainland China was inferred to have highly skewed sex ratios with predominant females. In addition, some populations experienced a recent bottleneck effect, especially in Gujianshan, Chongqing, and southwest China (population GJS). It is suggested that few wild male individuals should be conserved in order to maintain overall genetic diversity in the wild populations of this species. These findings provide important information for the sustainable utilization and preservation of the overall genetic diversity of L. glauca.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Population genetic structure and variability inLindera glauca(Lauraceae) indicates low levels of genetic diversity and skewed sex ratios in natural populations in mainland China

Xiong

Zhang

Dong

et al. 2020

PeerJ

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“…activity (Piao et al, 2008), superoxide anion scavenging activities (Sasaki et al, 2013), growth and differentiation of osteoblastic MC3T3-E1 (Kiem et al, 2008), anti-HIV-1 activities (Zhang et al, 2007;Warashima et al, 2008), downregulate cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS), and interleukin-1b (IL-1b) gene expressions in a dose-dependent manner in LPS-elicited mouse macrophages (Ma et al, 2007), inhibited NO production (Kim et al, 2014), anti-inflammatory activity (Wu et al, 2005), antimicrobial activities (Ding et al, 2014), antiproliferative activities against human cancer cell lines (Kim et al, 2011), and neurite-outgrowth promoting activity on PC12 cells (Kuroyanagi et al, 2008). On the other hands, biological activity of 1 has been documented as antiplasmodial activity (Abrantes et al, 2008) except for our reports, to date.…”

Section: Introductionmentioning

confidence: 99%

Chemistry and Neurotrophic Activities of (–)-Talaumidin and Its Derivatives

Harada

Kubo

2020

Front. Chem.

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Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan isolated from Aristolochia arcuata Masters, exhibits significant neurite-outgrowth promotion and neuroprotection in primary cultured rat cortical neurons and in NGF-differentiated PC12 cells. The first enantioselective total synthesis of 1 was achieved by a flexible and reliable synthetic pathway involving an Evans asymmetric aldol reaction, as well as a stereocontrolled hydroboration and Friedel-Crafts arylation, to construct the four contiguous chiral centers on the tetrahydrofuran (THF) ring of 1. In order to investigate the stereochemistry-activity relationship of 1, a systematic synthesis of all diastereomers of 1 was accomplished by applying the synthetic strategy used for natural product 1. The evaluation of neurite-outgrowth promotion by all of the synthesized diastereomers indicated that the (-)-(1S,2R,3S,4R)-isomer 1e was significantly more active than naturally occurring 1. Additionally, we established a synthetic methodology for talaumidin derivatives that could be used to prepare a variety of analogs in a few steps and on a large scale. The synthesized racemic analog rac-1e (56a) exhibited neurite-outgrowth promoting activity in NGF-differentiated PC12 cells to the same degree as the optically active (-)-1e, revealing that a relative configuration bearing all-cis-substituents is important for potent neurotrophic activity, whilst the absolute configuration does not affect activity. Fourteen analogs based on (±)-56a were prepared via the same synthetic methodology. Among them, 56b with a methylenedioxy group on both benzene rings was found to exhibit the most significant neurite outgrowth promotion. In addition, 56a and 56b induced regeneration of the mouse optic nerve in vivo, and their activity was higher than that of talaumidin, as well as their in vitro measured activity. Furthermore, the structure-activity relationship of 56b indicated that the two benzene rings were essential structures, and that the methyl groups on the THF ring could enhance the neurotrophic activity. This result suggests that the two benzene rings of the talaumidin derivatives are essential structures for neurotrophic activity, while the two methyl groups on the THF ring can enhance neurite-outgrowth activity. Finally, it was observed that 1 and derivatives 56a and 56b exhibited potent regenerative activity in the injured mouse optic nerve in vivo.

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The large amounts of fatty acids and aromatic oils in its fruit make it of a great economic plant, especially for the production of drugs and lubricants (Kim et al, 2014). The volatile oil of ripe Litsea mollis fruits is a biopreservative of low-cost in the dairy industry (Cai et al, 2019).Immature Litsea mollis fruit (ILMF) is generally pickled with soy sauce, vinegar, pepper, garlic, and ginger as a popular cold appetizer in southwestern China (Zhang, 2015).

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confidence: 99%

“…The large amounts of fatty acids and aromatic oils in its fruit make it of a great economic plant, especially for the production of drugs and lubricants (Kim et al, 2014). The volatile oil of ripe Litsea mollis fruits is a biopreservative of low-cost in the dairy industry (Cai et al, 2019).…”

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confidence: 99%

Comparison of free and bound volatile profiles of immature Litsea mollis fruits grown in five distinct regions of China

et al. 2022

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The large amounts of fatty acids and aromatic oils in its fruit make it of a great economic plant, especially for the production of drugs and lubricants (Kim et al., 2014). The volatile oil of ripe Litsea mollis fruits is a biopreservative of low-cost in the dairy industry (Cai et al., 2019).Immature Litsea mollis fruit (ILMF) is generally pickled with soy sauce, vinegar, pepper, garlic, and ginger as a popular cold appetizer in southwestern China (Zhang, 2015). People usually only pay attention to the aroma of free volatiles in fruits, but the studies on the bound aroma compounds of other fruits show that the hydrolysis of bound volatiles can improve the overall aroma of the fruits. The bound forms, mainly referring to the glycosidically bound alcohols, terpenes, dimethyl isoprene, volatile organic acids and shikimic acid derivatives, can be released by enzymatic or acid hydrolysis (Sánchez-Palomo et al., 2017), and thus they are also considered as important aroma components (Sarry & Gunata, 2004). The glycosides in the bound volatile compounds identified in fruits are mainly O-β-D-glucosides and O-diglycosides. O-glycoside hydrolases (EC 3.2.1.x) are a widespread group of enzymes of significant biological, biomedical and industrial importance. They, as well as fungal enzymes (usually from Aspergillus niger), can release the bound aroma (Davis & Croteau, 2000). Chen et al. (1984) extracted volatile oils from matureLitsea mollis fruits by steam distillation and found that the aroma of volatile oils mainly came from terpenoids. To the best of our knowledge, only one work has been reported on the free volatile compounds in ILMF (Yang et al., 2020), where six terpenoids are found to be responsible for the typical flavor of ILMF. Other than that, the aroma compounds of ILMF, either the free forms or bound forms, have been rarely studied.In the present work, the volatile components in the ILMFs collected from different regions of China were extracted by headspace solid phase microextraction (SPME), and the glycosidically bound volatiles were enzymatically hydrolyzed with the pectinase from Aspergillus niger (Dziadas & Jelen, 2016;Yang et al., 2019). SPME is a simple, low cost, solvent free and sensitive method for aroma compound extraction without heating required, and thus can minimize the loss of aroma. The volatile components were then identified and quantitatively analyzed by GC-MS, and the volatile profiles of the ILMFs were compared, aiming to provide a scientific foundation for understanding the

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Bioactive Lignan Constituents from the Twigs of <i>Lindera glauca</i>

Cited by 17 publications

References 20 publications

Population genetic structure and variability inLindera glauca(Lauraceae) indicates low levels of genetic diversity and skewed sex ratios in natural populations in mainland China

Population genetic structure and variability inLindera glauca(Lauraceae) indicates low levels of genetic diversity and skewed sex ratios in natural populations in mainland China

Chemistry and Neurotrophic Activities of (–)-Talaumidin and Its Derivatives

Comparison of free and bound volatile profiles of immature Litsea mollis fruits grown in five distinct regions of China

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