Successful Structure Determination of Diverse Phenolic Compounds from a Minute Amount of Alpine Plant Flower Samples Using a Newly Developed Method
A joint research team including the National Museum of Nature and Science successfully analyzed over 10 phenolic compounds from just 2g of alpine plant flowers using a novel trace analysis method, paving the way for sustainable natural product discovery.
📋 Article Processing Timeline
- 📰 Published: March 31, 2026 at 23:00
- 🔍 Collected: April 1, 2026 at 13:39 (14h 39m after Published)
- 🤖 AI Analyzed: April 22, 2026 at 07:55 (498h 16m after Collected)
Hinata Hirano (United Graduate School of Agricultural Science, Tokyo University of Agriculture and Technology), a cooperative graduate student at the National Museum of Nature and Science (Director: Kenichi Shinoda), along with Takashi Kikuchi (Application Lab, Product Division, Rigaku Corporation, a group company of Rigaku Holdings), Futa Sakakibara (Technical Advisor, R&D Support Division, Asterism LLC), and Yoshinori Murai (Principal Investigator, Department of Botany), have successfully determined the structures of more than 10 phenolic compound glycosides in alpine plants, where the plants are small and securing research samples is difficult from licensing and ethical perspectives, by developing a trace component analysis method. Specifically, by isolating and crystallizing components from just 2 grams of flowers of the alpine plant Diapensia lapponica var. obovata (Diapensiaceae), and by appropriately utilizing analytical techniques such as Single Crystal X-Ray Diffraction (SC-XRD) and Microcrystal Electron Diffraction (MicroED), they succeeded in determining the structure of each contained component. This is a pioneering research example of determining numerous component structures from such a minute sample in wild plants, including alpine plants. This is a technology that can be applied to exploratory research of unutilized resources in a wide range of fields such as physical sciences, agriculture, and pharmacy, in addition to plant chemical components. The results of this research were published online in the international chemistry journal "Journal of Molecular Structure" on February 22, 2026. Furthermore, research results utilizing related technologies were published in the international biochemical journal "Biochemical Systematics and Ecology" and the domestic agricultural industry journal "AgriBio."
[Research Points]
- Established techniques for isolating and crystallizing trace components.
- Successfully analyzed structures by appropriately utilizing analytical techniques for the crystallized components, such as Single Crystal X-Ray Diffraction (SC-XRD) and Microcrystal Electron Diffraction (MicroED).
- Successfully analyzed the structures of phenolic compounds from alpine plants with limited sample amounts, revealing that Diapensia lapponica var. obovata flowers contain diverse phenolic compounds.
- During the development of the method, related research also discovered components related to the chemical adaptation mechanisms and phylogeny of the plants.
1. Background and Results of the Research
Alpine plants distributed in the alpine and subalpine zones of Japan are known to undergo environmental adaptation by synthesizing and accumulating chemical components called phenolic compounds to cope with severe environmental stress such as ultraviolet rays and low temperatures originating from the alpine environment. In addition, it is known that many of these phenolic compounds are components that can serve as natural product resources, and research is particularly expected in alpine plants where knowledge is limited compared to lowlands. On the other hand, because alpine plants grow in harsh environments, the plant bodies are small, and their distribution is limited to high-altitude areas, making them rare. Even for academic research, due to legal licensing and ethical perspectives, it is necessary to minimize anthropogenic disturbances associated with collection, so the amount of sample available for the structural analysis of the aforementioned components is limited. This research team has previously advanced the development of methods for analyzing components from trace samples. This time, using an extremely small amount of flowers of the alpine plant Diapensia lapponica var. obovata as a research sample, they developed a method to optimize the crystallization of each contained component after steps such as isolation and purification using existing analytical methods like High-Performance Liquid Chromatography (HPLC) and molecular weight measurement using a Quadrupole Time-of-Flight Mass Spectrometer (QTOF-MS). Furthermore, by utilizing analytical techniques such as Single Crystal X-Ray Diffraction (SC-XRD) and Microcrystal Electron Diffraction (MicroED), which can determine structures from crystals about 1/100 the size of conventional ones, they succeeded in structural analysis of trace components from extremely trace samples. Through this research, it was revealed that the flowers of Diapensia lapponica var. obovata growing in the harsh alpine environment contain diverse phenolic compounds, including flavonoids such as quercetin glycosides, which have recently attracted attention as functional components that provide health benefits.
In addition, during the process of the aforementioned technology development, they isolated numerous components from the leaves of Diapensia lapponica var. obovata and succeeded in their structural analysis, finding components contributing to UV protection and antioxidant activity. Furthermore, they discovered geographical differences in the accumulation of some of these components from central Honshu to Hokkaido in the Japanese archipelago, and these results were published in "Biochemical Systematics and Ecology." This time, it is a further improvement of this research. The domestic agricultural industry journal "AgriBio" also summarizes and introduces the points of this research in an article.
[Research Points]
- Established techniques for isolating and crystallizing trace components.
- Successfully analyzed structures by appropriately utilizing analytical techniques for the crystallized components, such as Single Crystal X-Ray Diffraction (SC-XRD) and Microcrystal Electron Diffraction (MicroED).
- Successfully analyzed the structures of phenolic compounds from alpine plants with limited sample amounts, revealing that Diapensia lapponica var. obovata flowers contain diverse phenolic compounds.
- During the development of the method, related research also discovered components related to the chemical adaptation mechanisms and phylogeny of the plants.
1. Background and Results of the Research
Alpine plants distributed in the alpine and subalpine zones of Japan are known to undergo environmental adaptation by synthesizing and accumulating chemical components called phenolic compounds to cope with severe environmental stress such as ultraviolet rays and low temperatures originating from the alpine environment. In addition, it is known that many of these phenolic compounds are components that can serve as natural product resources, and research is particularly expected in alpine plants where knowledge is limited compared to lowlands. On the other hand, because alpine plants grow in harsh environments, the plant bodies are small, and their distribution is limited to high-altitude areas, making them rare. Even for academic research, due to legal licensing and ethical perspectives, it is necessary to minimize anthropogenic disturbances associated with collection, so the amount of sample available for the structural analysis of the aforementioned components is limited. This research team has previously advanced the development of methods for analyzing components from trace samples. This time, using an extremely small amount of flowers of the alpine plant Diapensia lapponica var. obovata as a research sample, they developed a method to optimize the crystallization of each contained component after steps such as isolation and purification using existing analytical methods like High-Performance Liquid Chromatography (HPLC) and molecular weight measurement using a Quadrupole Time-of-Flight Mass Spectrometer (QTOF-MS). Furthermore, by utilizing analytical techniques such as Single Crystal X-Ray Diffraction (SC-XRD) and Microcrystal Electron Diffraction (MicroED), which can determine structures from crystals about 1/100 the size of conventional ones, they succeeded in structural analysis of trace components from extremely trace samples. Through this research, it was revealed that the flowers of Diapensia lapponica var. obovata growing in the harsh alpine environment contain diverse phenolic compounds, including flavonoids such as quercetin glycosides, which have recently attracted attention as functional components that provide health benefits.
In addition, during the process of the aforementioned technology development, they isolated numerous components from the leaves of Diapensia lapponica var. obovata and succeeded in their structural analysis, finding components contributing to UV protection and antioxidant activity. Furthermore, they discovered geographical differences in the accumulation of some of these components from central Honshu to Hokkaido in the Japanese archipelago, and these results were published in "Biochemical Systematics and Ecology." This time, it is a further improvement of this research. The domestic agricultural industry journal "AgriBio" also summarizes and introduces the points of this research in an article.