Abstract

Three new tuliposides H–J (1–3) and 11 known compounds were obtained from the methanolic extracts of the bulbs of Amana edulis for the first time. Their structures were elucidated by NMR, MS, and IR spectroscopic data, optical rotation, and Mosher’s method. The melanogenesis properties of all the isolates were evaluated in B16 melanoma cells. Consequently, tributyl citrate (9) had anti-melanogenesis activity but was cytotoxic toward B16. (+)-Pyroglutamic acid (4), (+)-butyl 5-oxopyrrolidine-2-carboxylate (6), (–)-3-hydroxy-2-methylbutyrolactone (10), and 5-(hydroxymethyl)furfural (12) had increased melanin productions and tyrosinase activities. Those active components could be further studied as the candidates against melanoma and vitiligo for skin diseases or whitening/hypopigmentation for hair.

Highlights

  • Amana edulis (A. edulis; Miq.) Honda, syn

  • In a research of new agents from natural products for skin disorders, we found that the MeOH extracts of the bulbs of A. edulis show potential melanogenesis regulation that has not yet been researched

  • The MeOH extract (TEM) of this species was separated into TEE, TEB, and TEW crude fractions, and the aforementioned four extracts were evaluated for cytotoxicity and melanogenesis effects in B16 melanoma cells at concentrations from 12.5 to 200 μg/mL (Figure S24)

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Summary

Introduction

In a research of new agents from natural products for skin disorders, we found that the MeOH extracts of the bulbs of A. edulis show potential melanogenesis regulation that has not yet been researched. The active components of A. edulis are worthy to be clarified for further medical applications. In this investigation, three new tuliposides H–J (1–3) and 11 known compounds (4–14) (Figure 1) were isolated from A. edulis and structurally identified by NMR, MS, and IR spectroscopic data, optical rotation, or Mosher ester reaction. Compounds 4, 6, 10, and 12 had increased melanin productions and tyrosinase activities. This work proved A. edulis and its active components could be new agents for mweolraknpinr-orveeladteAd. dedisueliassaens,dsuitcshacatsivmeecloamnopmonaeanntsdchoyupldopbiegmneewntaagtieonnts(sfkoirnmveitlialnigino-orerlahtaeidr wdihsietaesneisn,gs)u. This work proved A. edulis and its active components could be new agents for mweolraknpinr-orveeladteAd. dedisueliassaens,dsuitcshacatsivmeecloamnopmonaeanntsdchoyupldopbiegmneewntaagtieonnts(sfkoirnmveitlialnigino-orerlahtaeidr wdihsietaesneisn,gs)u. ch as melanoma and hypopigmentation (skin vitiligo or hair whitening)

Results and Discussion
Glc 1 2 3 4 5 n-butyl 1” 2” 3” 4”
Effects of Extracts and Isolates on Melanogenesis
Extraction and Isolation
Measurement of B16 Cell Viability
Measurement of Melanin Content in B16 Cells
Intracellular Tyrosinase Activity
Conclusions
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