Inhibitory effects of the ethyl acetate extract from bulbs of Scilla scilloides on lipoxygenase and hyaluronidase activities

Figures & data

Figure 1. Chemical structures of nine homoisoflavones from the bulbs of S. scilloides.

Table 1. List of the chemicals previously isolated by the authors and used in this study^a.

Chemical name (synonyms)	References
Homoisoflavones
1 Scillavone B ((3S)-3-(3,4-dihydroxybenzyl)-5-hydroxy-6,7-dimethoxychroman-4-one)	Nishida et al. (2008)
2 3,9-Dihydroeucomnalin	Nishida et al. (2008)
3 3-(3,4-Dihydroxybenzyl)-5,7-dihydroxy-6-methoxychroman-4-one	Nishida et al. (2008)
4 3-(4-Hydroxybenzylidene)-5,7-dihydroxychroman-4-one	Nishida et al. (2008)
5 3-(3,4-Dihydroxybenzylidene)-5,7-dihydroxy-6-methoxy-chroman-4-one	Nishida et al. (2008)
6 Scillavone A ((3 R)-5,7,2′-trihydroxy-3′,4′-dimethoxyspiro{2H-1-benzopyran-7′-bicyclo[4,2,0]octa[1,3,5]-trien}-4-one)	Nishida et al. (2008)
7 5,7,3′-Trihydroxy-4′- methoxyspiro{2H-1-benzopyran-7′-bicyclo[4,2,0]octa[1,3,5]-trien}-4-one	Nishida et al. (2008)
8 Scillascillin	Nishida et al. (2008)
9 2-Hydroxy-scillascillin	Nishida et al. (2008)
Others
4-Methylresveratrol (3,5,4′-trihydroxy-  4-methyl-trans-stilbene)	Nishida et al. (2008)
Scillabene A	Nishida et al. (2008)
1,6-Dihydroxy-3-methoxy-  8-methylxanthone	Nishida et al. (2008)
Pinoresinol	Nishida et al. (2008)
3-Dehydro-15-deoxoeucosterol	Nishida et al. (2008)
15-Deoxoeucosterol	Nishida et al. (2008)
30-Hydroxy-15-deoxoeucosterol	Nishida et al. (2008)
Scillanostaside A	Ono et al. (2011)
Scillanostaside B	Ono et al. (2011)
Scillanostaside C	Ono et al. (2011)
Scillanostaside D	Ono et al. (2011)
Scillanostaside E	Ono et al. (2011)
Scillascilloside G-1	Ono et al. (2011)
Scillanostaside F	Ono et al. (2012)
Scillanostaside G	Ono et al. (2012)
Demethyleugenol 4-O-β-d-xylopyranosyl-  (1→6)-O-β- d -glucopyranoside	Ono et al. (2012)
Narciclasine	Ono et al. (2012)
O-Methyllycorenine	Ono et al. (2012)
Scillanostaside H	Ono et al. (2013)
Scillanostaside I	Ono et al. (2013)
Scillanostaside J	Ono et al. (2013)
Scillanostaside K	Ono et al. (2013)
Scillanostaside L	Ono et al. (2013)

^aChemicals with a bold numeral are the compounds used in this study.

Figure 2. Effect of concentration of S. scilloides extract in lipoxygenase (A) and hyaluronidase assays (B). Data shown represent mean ± S.D. from four experiments. NDGA in (A) and tannic acid in (B) were used as the standard sample.

Table 2. Inhibitory effects of nine homoisoflavones (1–9) from S. scilloides in lipoxygenase and hyaluronidase assays^a.

Compound	500 µM	750 µM	1000 µM	IC50 (µM)
	Lipoxygenase inhibition (%) at various concentrations
1	97.7 ± 1.4	–^b	–	(35.8)^c
2	20.2 ± 1.4	34.6 ± 7.5	38.2 ± 3.6	1000<
3	89.0 ± 1.6	–	–	(26.9)
4	79.3 ± 4.5	–	–	(286)
5	92.1 ± 1.1	–	–	(15.8)
6	22.1 ± 12.8	26.1 ± 5.2	23.9 ± 8.5	1000<
7	32.7 ± 7.3	45.8 ± 8.2	51.7 ± 4.4	927
8	6.7 ± 1.7	21.6 ± 7.7	28.7 ± 13.3	1000<
9	25.7 ± 6.3	45.6 ± 11.8	74.9 ± 7.6	788
NDGA	97.9 ± 3.2	–	–	(9.61)
	Hyaluronidase inhibition (%) at various concentrations
1	23.8 ± 1.8	50.2 ± 0.8	52.4 ± 13.8	748
2	–	–	40.0 ± 8.3	1000<
3	–	–	40.5 ± 7.6	1000<
4	–	–	16.2 ± 4.5	1000<
5	26.9 ± 2.5	40.2 ± 1.2	58.0 ± 7.7	887
6	–	–	27.8 ± 5.9	1000<
7	–	–	28.0 ± 8.9	1000<
8	–	–	38.4 ± 4.3	1000<
9	–	–	39.1 ± 7.1	1000<
Tannic acid	99.8 ± 1.6	–	102.1 ± 0.3	<500

^aData shown represent mean ± S.D. from three determinations. The final concentrations of each sample tested were 500 µM, 750 µM or 1000 µM in lipoxygenase and hyaluronidase assays. NDGA and tannic acid were used as the standard samples.

^bA dash indicates not tested.

^cData shown in parentheses indicate IC₅₀ values calculated from the data obtained in Figure 3.

Figure 3. Effect of concentration of four homoisoflavones (1 and 3–5) from S. scilloides in lipoxygenase assay. Data shown represent mean ± S.D. from three experiments. NDGA was used as the standard sample.

Figure 4. Inhibitory effect of nine homoisoflavones (1–9) from S. scilloides on the NO production in LPS-stimulated RAW264.7 mouse macrophage-like cells. Cells were incubated in the presence of 10 µM (gray bar) or 50 µM (black bar) of individual compounds plus 100 ng/mL LPS for 24 h. The culture media were collected and analyzed for determination of NO level by the Griess method. Data shown represent mean ± S.D. from four experiments. #Significant differences from untreated cells (control), p < 0.001, and *Significant differences from LPS treated cells, p < 0.001. NO, nitric oxide; LPS, lipopolysaccharide.

Nishida Y, Eto M, Ikeda T, et al. (2008). A new homostilbene and two new homoisoflavones from the bulbs of Scilla scilloides. Chem Pharm Bull 56:1022–5

 PubMed Web of Science ®Google Scholar

Ono M, Toyohisa D, Morishita T, et al. (2011). Three new nortriterpene glycosides and two new triterpene glycosides from the bulbs of Scilla scilloides. Chem Pharm Bull (Tokyo) 59:1348–54

 PubMed Web of Science ®Google Scholar

Ono M, Takatsu Y, Ochiai T, et al. (2012). Two new nortriterpenoid glycosides and a new phenylpropanoid glycoside from the bulbs of Scilla scilloides. Chem Pharm Bull (Tokyo) 60:1314–19

 PubMed Web of Science ®Google Scholar

Ono M, Ochiai T, Yasuda S, et al. (2013). Five new nortriterpenoid glycosides from the bulbs of Scilla scilloides. Chem Pharm Bull (Tokyo) 61:592–8

 PubMed Web of Science ®Google Scholar