Protosappanin A, a novel biphenyl compound from Sappan Lignum.

Nagai, Masahiro; Nagumo, Shinji; Lee, Shu-Mei; Eguchi, Ikuyo; Kawai, Ken‐ichi

doi:10.1248/cpb.34.1

Cited by 57 publications

(48 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In addition, its 13 Table 2). These data were similar to those of protosappanin A (7), 10) isolated from the same extract, but they were characterized by the appearance of signals of two methoxyl groups and an acetal carbon and disappearance of the signal of a ketone carbonyl carbon in 7. Thus, 3 was assumed to be protosappanin A dimethyl acetal, which was confirmed by the HMBC spectrum and the fact that an acid treatment of 3 gave 7.…”

supporting

confidence: 81%

“…6) The known compounds were identified by analysis of their spectroscopic data and comparison with literature data to be protosappanin E-2 (2), 7) protosappanin B (5), 8) protosappanin C dimethyl acetal (6), 9) protosappanin A (7), 10) brazilin (8), 11) 3Ј-O-methylbrazilin (9), 12) 3Ј-deoxysappanol (10), 13,14) 3Ј-deoxy-4-O-methylsappanol (11), 15) 4-O-methylsappanol (12), 12,16) sappanol (13), 15) 4-Omethylepisappanol (14), 12,16) sappanone B (15), 12,15) 3-deoxysappanone B (16), 12,16) and sappanchalcone (17). 17) Neoprotosappanin (1) This suggested that the two singlets in unit II should be para to each other.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Xanthine Oxidase Inhibitors from the Heartwood of Vietnamese Caesalpinia sappan

et al. 2005

View full text Add to dashboard Cite

From the MeOH extract of Vietnamese Caesalpinia sappan, a novel biogenetically exclusive benzindenopyran, with a new carbon framework, neoprotosappanin (1), and a new compound, protosappanin A dimethyl acetal (3), were isolated together with protosappanin E-2 (2), neosappanone A (4), and 13 previously reported phenolic compounds (5-17). Their structures were elucidated on the basis of spectroscopic data. Compounds 1-4, 7, 13, and 15-17 showed significant xanthine oxidase inhibitory activity in a concentration-dependent manner, and sappanchalcone (17) showed the most potent activity with an IC 50 value of 3.9 m mM, comparable to that of positive control allopurinol (IC 50 , 2.5 m mM). The kinetic study of these inhibitors indicated that they are competitive inhibitors, the same as allopurinol, except for 1 and 16 which are noncompetitive inhibitors.

show abstract

supporting

confidence: 81%

Section: Resultsmentioning

confidence: 99%

Xanthine Oxidase Inhibitors from the Heartwood of Vietnamese Caesalpinia sappan

et al. 2005

View full text Add to dashboard Cite

show abstract

“…1,[12][13][14][15] Brazilin, a phenolic oxygen heterocycle is found to be the major constituent of the heartwood and found to possess immuno stimulant, 6) hypoglycemic, 10) anticomplementary, 5) hepatoprotective 7) and vaso relaxation 27) properties. Free radical mediated processes have been implicated in the pathogenesis of most of these diseases.…”

Section: Resultsmentioning

confidence: 99%

“…1) Several triterpenoids, 11) flavonoids, 12,13) phenolics, 12,14,15) steroids 11) have been isolated from the heartwood.…”

mentioning

confidence: 99%

Antioxidant Activity of Caesalpinia sappan Heartwood

Badami¹,

Moorkoth²,

Rammanoharsingh³

et al. 2003

Biological & Pharmaceutical Bulletin

127

View full text Add to dashboard Cite

“…Their stimulation activity revealed that the fraction 4 exhibits the strongest activity in the osteoblastic cells by 200±2% at a concentration of 100 µg ml −1 . Finally, further purification of chemical constituents in this fraction afforded three compounds, a new biphenyl dimer, caesappanin C, (1) and two known compounds, protosappanin A (2) (Nagai et al 1986;Fu et al 2008) and sappanchalcone (3) (Namikoshi et al 1987) (Figure 1). Spectral data of the known compounds has been confirmed with the reported data.…”

Section: Resultsmentioning

confidence: 99%

Phytochemical investigation of the active constituents from <i>Caesalpinia sappan</i> on stimulation of osteoblastic cells

Subehan

Rifai

Mufidah

et al. 2014

Plant Biotechnology

View full text Add to dashboard Cite

Heartwood of Caesalpinia sappan L. has been traditionally used to many diseases such as homoptysis, syphilis, eye disease, dysentery, depurative and prevention of osteoporosis. Our previous in vitro screening of Indonesian plants revealed that an ethanolic extract of the heartwood of C. sappan exhibits a proliferation stimulating activity against primary osteoblastic cells. In our continued interest to this plant, we further fractionated the extract and isolated active constituents on the basis of the stimulating activity in the osteoblastic cells. The fractionation and isolation were carried out with various chromatography methods and the structure of isolated compounds was elucidated based on NMR, IR, UV and MS spectroscopic data. From an active fraction, a new biphenyl dimer, namely caesappanin C (1), along with two known compounds, protosappanin A (2) and sappanchalcone (3), were isolated. Among them, the new compound 1 exhibited the strongest activity and significantly increased the cell viability up to 276±5%. The other two compounds 2 and 3 also stimulated the cell proliferation and increased the cell viability up to 233±8% and 187±4%, respectively.

show abstract

Protosappanin A, a novel biphenyl compound from Sappan Lignum.

Cited by 57 publications

References 0 publications

Xanthine Oxidase Inhibitors from the Heartwood of Vietnamese Caesalpinia sappan

Xanthine Oxidase Inhibitors from the Heartwood of Vietnamese Caesalpinia sappan

Antioxidant Activity of Caesalpinia sappan Heartwood

Phytochemical investigation of the active constituents from <i>Caesalpinia sappan</i> on stimulation of osteoblastic cells

Contact Info

Product

Resources

About