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A new steroidal alkaloid, michainine (1), was isolated from Fritillaria michailovskyi Fomin, along with nine known compounds 2-10 of different classes, including ribonucleoside, steroids, and fatty acids, which were isolated for the first time from this plant. Their structures were elucidated through extensive spectroscopic techniques, as well as by comparing the data in the literature. Furthermore, the dichloromethane fraction of F. michailovskyi showed a positive butyrylcholinesterase inhibitory activity, along with noncytotoxicity against 3T3 cell line.

Fritillaria aurea, unlike other Fritillaria species, is a narrowly endemic species. It has a brown checkered speckled color on each tepal and also has regular yellow intense colors on the tepals. Its large bell-shaped appearance when the flower is open is one of its most striking ornamental features. However, F. aurea plant numbers are limited in their natural habitats, and their numbers are decreasing day by day; they are even confronted with the risk of extinction owing to the damage resulting from human activities. This detailed investigation of reproductive biology plays a vital role in determining the evolutionary success and survival of F. aurea, largely in determining the effectiveness of their reproductive performance. Our results indicate that the species exhibits a very low partial dichogamy and herkogamy structure, as well as self-incompatible pollination. The flowering period ranges from March to April. Average seed viability, average seed number, and seed germination were determined as 71%, 255, and 45%, respectively. The pollen viability, pollen grains, and stigma receptivity were found as 96%, 392.000, and 85%, respectively. The pollen/ovule ratio (P/O) and self-incompatibility index (SII) in the spontaneous cross-pollination were detected as 1537 and 0, respectively. Flowers of F. aurea were visited by several insect species, mostly honeybees (Apis mellifera); Bombus sp. and Vespa sp. also played a minor role in pollination. To sum up, these results not only lay a solid foundation for further reproductive biology investigations to more broadly reveal the mechanisms of F. aurea endangerment in the future but also provide a reliable theoretical basis for hybridization breeding of parents.

Fritillaria is highly endangered in their natural habitats, and these species are perennial bulbous plants with an important medicinal and ornamental value whose reproductive strategies and adaptive evolution mechanisms are still not fully clear. Therefore, the reproductive strategies of endemic species, like Fritillaria michailovskyi Fomin are important to detect the community structure and the diversity patterns of ornamental plants. The current paper on the reproductive strategy of F. michailovskyi, a rare endemic species, was carried out at the Erzincan Horticultural Research Institute, Turkey. Our results indicate that the flowering stages of F. michailovskyi may be divided into eight phases. According to pollination experiments and the pollen/ovule ratio, and the self-incompatibility index (SII) in an ex-situ population, F. michailovskyi indicated high levels of xenogamy and self-incompatibility. It was determined that the pollination of F. michailovskyi mostly depended on pollen vectors, and the effective pollinators of F. michailovskyi were Apis mellifera and Bombus terrestris. In addition, average seed number, seed germination, and average seed viability were found as 144, 46%, and 67%, respectively. The stigma receptivity, pollen grains, and pollen viability were detected as 83%, 252,000, and 95%, respectively. Our study is the first report providing a detailed explanation of the reproductive strategy of this rare endemic species, which could aid in the genetic evolution and conservation of this valuable taxa.

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