Match!

Chemical constituents of hybrids of Ligularia cyathiceps and L. lamarum/L. subspicata collected in China: Structures of subspicatins M, N, O1, and O2, and related compounds

Published on Aug 1, 2017in Phytochemistry2.90
· DOI :10.1016/j.phytochem.2017.04.015
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University),
Mayu Ichihara5
Estimated H-index: 5
(Tokushima Bunri University)
+ 5 AuthorsMotoo Tori31
Estimated H-index: 31
(Tokushima Bunri University)
Cite
Abstract
Abstract Three natural hybrids and an introgressed individual of Ligularia were evaluated based on a combination of morphology, root chemicals, and nucleotide sequences of evolutionally neutral regions to understand the chemical outcomes of hybridization and introgression. Six previously undescribed eremophilane sesquiterpenes were isolated from hybrids between L. cyathiceps and L. lamarum / L. subspicata , and benzofurans were isolated from L. subspicata for the first time. Their structures were elucidated based on spectroscopic analyses. Some compounds produced by hybrids have not been detected in either parental species, indicating that the metabolic profile was altered by hybridization and introgression.
Figures & Tables
  • References (38)
  • Citations (3)
Cite
References38
Newest
Published on Aug 1, 2016in Natural Product Communications0.55
Rye Hanai1
Estimated H-index: 1
(Rikkyo University),
Sayako Tanabe1
Estimated H-index: 1
(Rikkyo University)
+ 5 AuthorsChiaki Kuroda10
Estimated H-index: 10
(Rikkyo University)
The composition of root chemicals was examined for samples of L. cyathiceps x L. duciformis, L. duciformis x L. yunnanensis, and L. yunnanensis. Various furanoeremophilanes were isolated from a sample of L. cyathiceps x L. duciformis and found to be very similar to those isolated from L. cyathiceps. Lupeol and docosyl ferulate were isolated from L. yunnanensis, L. duciformis, and L. duciformis x L. yunnanensis.
Published on Jul 1, 2016in Chemistry & Biodiversity1.45
Anna Shimizu4
Estimated H-index: 4
(Rikkyo University),
Ryo Hanai17
Estimated H-index: 17
(Rikkyo University)
+ 4 AuthorsChiaki Kuroda10
Estimated H-index: 10
(Rikkyo University)
Two samples with morphologies intermediate between Ligularia tongolensis and L. cymbulifera were collected in Desha, Sichuan Province, and one, in Pachahai, Yunnan Province, P. R. China. The DNA sequencing confirmed that the samples were hybrids of the two species. Tetradymol (1), the major compound of L. cymbulifera not found in L. tongolensis, was isolated from the hybrid samples collected at both locations, while furanoeremophilan-15-oic acid derivative 4, a compound characteristic to L. tong...
Published on Jul 1, 2016in Natural Product Communications0.55
Yoshinori Saito12
Estimated H-index: 12
(Nagasaki University),
Yuriko Takashima4
Estimated H-index: 4
(Tokushima Bunri University)
+ 4 AuthorsMotoo Tori2
Estimated H-index: 2
(Tokushima Bunri University)
Published on Dec 31, 2014in PLOS ONE2.78
Jiao-Jun Yu3
Estimated H-index: 3
(CAS: Chinese Academy of Sciences),
Chiaki Kuroda10
Estimated H-index: 10
(Rikkyo University),
Xun Gong23
Estimated H-index: 23
(CAS: Chinese Academy of Sciences)
Natural hybridization has been considered to represent an important factor influencing the high diversity of the genus Ligularia Cass. in the Hengduan Mountains, China. Natural hybridization has been confirmed to occur frequently in Ligularia. To date, however, it has been demonstrated only within a single population. In this paper, we present evidence of natural hybridization in Ligularia from four different locations. The internal transcribed spacer (ITS) region of the nuclear ribosomal DNA an...
Published on Dec 1, 2012in Natural Product Communications0.55
Ryo Hanai17
Estimated H-index: 17
(Rikkyo University),
Hiroka Yamada4
Estimated H-index: 4
(Ochanomizu University)
+ 5 AuthorsChiaki Kuroda17
Estimated H-index: 17
(Rikkyo University)
Four Ligularia individuals possessing morphological characters of both L. nelumbifolia and L. subspicata were discovered in Shangrila County, Yunnan Province, China. DNA sequencing showed that the specimens were hybrids of the two species and their maternal parent was L. subspicata. The chemical composition of the root extract was examined for three of them as well as L. nelumbifolia and L. subspicata collected sympatrically. Nelumol was isolated from L. nelumbifolia, and furanoeremophilanes fro...
Published on Dec 1, 2012in Tetrahedron2.38
Yoshinori Saito12
Estimated H-index: 12
(Tokushima Bunri University),
Yuriko Takashima4
Estimated H-index: 4
(Tokushima Bunri University)
+ 9 AuthorsXun Gong23
Estimated H-index: 23
(CAS: Chinese Academy of Sciences)
Root chemicals and DNA sequences were analyzed for Ligularia virgaurea collected in the northern Sichuan Province and adjacent areas of China. Thirty-eight samples were found to contain five chemotypes, two known and three new ones. From samples of the new chemotypes, 13 new compounds were isolated, including 3 sesquiterpene dimers and some rearranged eremophilanes. The DNA sequences suggested that the chemotype differentiation had a genetic origin. (C) 2012 Elsevier Ltd. All rights reserved.
Published on Apr 1, 2012in Natural Product Communications0.55
Chiaki Kuroda17
Estimated H-index: 17
(Rikkyo University),
Ryo Hanai17
Estimated H-index: 17
(Rikkyo University)
+ 2 AuthorsXun Gong23
Estimated H-index: 23
(Kunming Institute of Botany)
The chemical and genetic diversity of Ligularia species in the Hengduan Mountains area of China is reviewed. A hypothesis that the production of furanoeremophilanes is ecologically advantageous is proposed.
Published on Nov 1, 2011in Tetrahedron Letters2.26
Yoshinori Saito12
Estimated H-index: 12
(Tokushima Bunri University),
Mayu Ichihara5
Estimated H-index: 5
(Tokushima Bunri University)
+ 3 AuthorsMotoo Tori31
Estimated H-index: 31
(Tokushima Bunri University)
Five new 1 beta-angeloyloxyeremophilanolides (subspicatins H-L) and 1 beta-angeloyloxytetranoreremophilanone (norsubspicatin A), were isolated from the EtOAc extracts of Parasenecio petasitoides and their structures established on the basis of spectroscopic analyses. They are biogenetically mutually related to each other and represent a new category in the Parasenecio group. These findings suggest that there is diversity in this species, too. (C) 2011 Elsevier Ltd. All rights reserved.
Published on Sep 1, 2011in Journal of Systematics and Evolution4.04
Jiao-Jun Yu1
Estimated H-index: 1
(CAS: Chinese Academy of Sciences),
Chiaki Kuroda10
Estimated H-index: 10
(Rikkyo University),
Xun Gong23
Estimated H-index: 23
(CAS: Chinese Academy of Sciences)
The difficulty in clarifying species of genus Ligularia Cass. has been attributed to rapid and continuous allopatric speciation in small and isolated populations, combined with interspecific diploid hybridization in the Qinghai-Tibetan Plateau and adjacent areas. However, no concrete example has been reported to prove this hypothesis. We studied a natural mixed population of six species of Ligularia in which some individuals were morphologically intermediate between L. subspicata and L. nelumbif...
Cited By3
Newest
Published on Aug 1, 2019in Phytochemistry Letters1.34
Hossam M. Abdallah14
Estimated H-index: 14
(Cairo University),
Ali M. El-Halawany14
Estimated H-index: 14
(Cairo University),
Hany M. El-Bassossy15
Estimated H-index: 15
(KAU: King Abdulaziz University)
Published on Jul 3, 2018in Frontiers in Pharmacology3.85
Xinlian Chen1
Estimated H-index: 1
(State Administration of Traditional Chinese Medicine of the People's Republic of China),
Jianguo Zhou1
Estimated H-index: 1
(State Administration of Traditional Chinese Medicine of the People's Republic of China)
+ 3 AuthorsHui Yao1
Estimated H-index: 1
(State Administration of Traditional Chinese Medicine of the People's Republic of China)
More than 30 Ligularia Cass. (Asteraceae) species have long been used in folk medicine in China. Morphological features and common DNA regions are both not ideal to identify Ligularia species. As some Ligularia species contain pyrrolizidine alkaloids (PAs), which are hazardous to human and animal health and are involved in metabolic toxification in the liver, it is important to find a better way to distinguish these species. Here, we report complete chloroplast (CP) genomes of six Ligularia spec...
Published on Apr 1, 2018in Natural Product Communications0.55
Chiaki Kuroda17
Estimated H-index: 17
(Rikkyo University),
Taketo Itoh (Rikkyo University)+ 5 AuthorsXun Gong23
Estimated H-index: 23
(Kunming Institute of Botany)