Five New Homoisoflavonoids from the Tuber of Ophiopogon japonicus

Chang, Jin-Ming; Shen, Chien‐Chang; Huang, Yu‐Ling; Chien, Mei-Yin; Ou, Jun-Chih; Shieh, Bor‐Jinn; Chen, Chien-Chih

doi:10.1021/np020204o

Cited by 45 publications

(32 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These plants are ethnomedicinally important as the isolated homoisoflavonoid compounds have excreted antimutagenic and anticlastogenic properties. Accordingly, isolation of natural representatives [5][6][7][8][9][10] and synthesis of their analogues [11] are intensive fields of research due to the great pharmacological importance of the compounds. Earlier several derivatives have been synthesized to evaluate their structure-to-antiproliferative activity.…”

Section: Introductionmentioning

confidence: 99%

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

et al. 2011

View full text Add to dashboard Cite

1 H and 13 C NMR chemical shifts have been determined and assigned based on PFG 1 H, 13 C HMQC, and HMBC experiments for 3-(4 0 -X-benzyl)-4-chromenones (Ia, X = CN and Ib, X = NO 2 ), 3-(4 0 -X-benzyl)-4-thiochromenones (IIa, X = Cl and IIb, X = Br), (E)-3-(4 0 -Xbenzylidene)-4-chromanones (IIIa-IIIe, X = OCH 3 , CH 3 , Cl, N(CH 3 ) 2 , Br), (Z)-3-(4 0 -X-benzylidene)4-thiochromanones (IVa-IVd, X = Cl, Br, F, OCH 3 ), 2-benzyl-1,2,3, 4-tetrahydro-1-naphthol (V), 2-benzyl-and (E)-2-benzylidene-1-tetralones (VI and VII), and (E)-2-benzylidene-1-benzosuberol (VIII). The crystal structures have been determined for the following seven compounds: derivatives of 4-chromanones (IIIa-IIId), 1-tetrahydronaphtol (V), and 1-tetralones (VI and VII). The molecular features and intermolecular interactions in crystal state have been discussed.

show abstract

Section: Introductionmentioning

confidence: 99%

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

et al. 2011

View full text Add to dashboard Cite

show abstract

“…Liriope platyphylla Wang et Tang (LPWT) extract, Liliaceae, has also been used for diabetes and cardiovascular disease. Active components of LPWT has been identified as homoisoflavonoids (ophiopogone, methylopiogonone, etc), sterols (h-sistosterol etc), and steroidal glycosides (ruscogenin, ophiopogonin, etc) (Asano et al, 1993;Chang et al, 2002;Yu et al, 1996), but the functions have not been investigated. In the present study, the fractions of LPWT extracts were screened for their effects as an insulin sensitizer through insulin mediated glucose uptake in 3T3-L1 adipocytes, and the mechanism of action of the LPWT extract fractions as an insulin sensitizer was investigated.…”

Section: Introductionmentioning

confidence: 99%

The insulin sensitizing effect of homoisoflavone-enriched fraction in Liriope platyphylla Wang et Tang via PI3-kinase pathway

2004

View full text Add to dashboard Cite

“…Ophiopogon species (Liliaceae) are abundant in homoisoflavonoids. Up to now, at least 30 homoisoflavonoids have been isolated from these plants [13][14][15][16][17][18][19] (Figure 1). Recently, we isolated five pure homoisoflavonoids from O. japonicus, a traditional Chinese medicine (Mai-Dong) frequently used as a tonic drug in the clinic.…”

mentioning

confidence: 99%

Analysis of homoisoflavonoids in Ophiopogon japonicus by HPLC-DAD-ESI-MS

Guo

Guan

et al. 2005

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

The homoisoflavonoids in Ophiopogon japonicus (Thunb.) Ker-Gawler were analyzed by high-performance liquid chromatography-diode array detection-electrospray ion trap tandem mass spectrometry (HPLC-DAD-ESI-MS n ). Homoisoflavonoids gave prominent [M Ϫ H] Ϫ ions by electrospray ionization monitored in the negative ion mode. They could be classified into two types depending on the fragmentation behavior of their [M Ϫ H] Ϫ ions in the ion trap mass analyzer. The [M Ϫ H] Ϫ ions of homoisoflavonoids with a saturated C 2-3 bond underwent C 3-9 bond cleavage to lose the B-ring, which was followed by the loss of a molecule of CO. The [M Ϫ H] Ϫ ions of homoisoflavonoids with a C 2-3 double bond usually eliminated a CO molecule first, and then underwent the cleavage of C 3-9 or C 9-1= bonds. For homoisoflavonoids with a C-6 formyl group, however, the neutral loss of CO was the first fragmentation step; the presence of a methoxyl group at C-8 could lead to the cleavage of C-ring. No retro Diels-Alder (RDA) fragmentation characteristic for normal flavonoids was observed. The above fragmentation rules were reported for the first time, and were implemented for the analysis of homoisoflavonoids in O. japonicus. The CHCl 3 -MeOH extract was separated on a Zorbax Extend-C 18 column, eluting with a acetonitrile-0.3% acetic acid gradient. A total of 18 homoisoflavonoids, including seven new minor constituents, were identified or tentatively characterized based on the UV spectra and tandem mass spectra of the HPLC peaks. (J Am Soc Mass Spectrom 2005, 16, 234 -243)

show abstract

Five New Homoisoflavonoids from the Tuber of Ophiopogon japonicus

Cited by 45 publications

References 11 publications

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

Structural studies of seven homoisoflavonoids, six thiohomoisoflavonoids, and four structurally related compounds

The insulin sensitizing effect of homoisoflavone-enriched fraction in Liriope platyphylla Wang et Tang via PI3-kinase pathway

Analysis of homoisoflavonoids in Ophiopogon japonicus by HPLC-DAD-ESI-MS

Contact Info

Product

Resources

About