Premium
Inhibitory Effects of Alpinia speciosa K. SCHUM on the Porphyrin Photooxidative Reaction
Author(s) -
Liao MingChing,
Arakaki Hajime,
Li Yaping,
Takamiyagi Atsushi,
Tawata Shinkichi,
Aniya Yoko,
Sakurai Hiromu,
aka Shigeo
Publication year - 2000
Publication title -
the journal of dermatology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.9
H-Index - 65
eISSN - 1346-8138
pISSN - 0385-2407
DOI - 10.1111/j.1346-8138.2000.tb02173.x
Subject(s) - singlet oxygen , chemistry , alpinia , quenching (fluorescence) , photochemistry , oxygen , organic chemistry , botany , biology , fluorescence , physics , quantum mechanics
It is thought that the β‐carotene defense mechanism against photosensitivity involves the inhibition of singlet oxygen formation, a kind of active oxygen. When we screened chemical substances obtained from plants indigenous to Okinawa, known to have residents with the longest life span in Japan, we found that Alpinia speciosa K. SCHUM (Japanese name: gettou), which is used as a food preservative, has an activity similar to that of β‐carotene. We measured the amount of lipid peroxide (LPO) formed from a hematoporphyrin‐containing rat liver microsomal suspension irradiated with visible light. The inhibitory effect of Alpinia speciosa on LPO formation was confirmed when the addition of increasing concentrations of Alpinia speciosa extract led to a decrease in the amount of LPO formed. Moreover, the reaction mechanism that affects the amount of singlet oxygen formed was measured, and the effect of the extract was determined by the ESR trapping technique. It was found that the extract effectively inhibited the formation of singlet oxygen. The extract of Alpinia speciosa contains dihydro‐5,6‐dehydrokawain. It was confirmed that dihydro‐5,6‐dehydrokawain, which is a water‐soluble compound, has singlet oxygen quenching activity. We synthesized five derivatives of kawain and found that dimethyl [6‐(2‐phenylethyl)‐2‐oxo‐2H‐pyran‐4‐yl] phosphorothionate has the strongest singlet oxygen quenching activity. The use of the compound from Alpinia speciosa that exhibits singlet oxygen quenching activity as an inhibitory agent of the phototoxic reaction in porphyria is expected.