Alangionosides G-M: Glycosides of Megastigmane Derivatives from the Leaves of Alangium premnifolium.

Otsuka, Hideaki; Yao, Masami; Kamada, Kenji; Takeda, Yoshio

doi:10.1248/cpb.43.754

Cited by 129 publications

(78 citation statements)

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“…The 13 C NMR together with DEPT mode measurement and H±H COSY revealed that the aglycone of compound 3 is (3S, 5S, 6R, 9R)-3-hydroxy-5,6-epoxy-b-ionol (Grayson, 1997). The attachment of the glucose moiety at C-9 of the aglycone was proved from the down®eld shift of this carbon to 75.3 when compared with closely similar megastigmanes (Otsuka et al, 1995). In order to establish the relative con®guration of the epoxy group, H±H NOESY experiment was carried out (Fig.…”

Section: Resultsmentioning

confidence: 97%

Iridoid and megastigmane glycosides from Phlomis aurea

et al. 2000

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Section: Resultsmentioning

confidence: 97%

Iridoid and megastigmane glycosides from Phlomis aurea

et al. 2000

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“…Structure elucidation of 1-7 Compounds 1-7 were identified as pyrroside B (Hori et al, 1988), swertisin (Fujita & Inoue, 1982), isovitexin (Harborne & Mabry, 1986), isoswertiajaponin (Fujita & Inoue, 1982), vomifoliol (blumenol A) (Fukui et al, 1977, Okamura et al, 1981, (6S,9R)-roseoside (Otsuka et al, 1995, Okamura et al, 1981 and angelicoidenol (Mahmood et al, 1983), respectively, on the bases of physical and spectral data (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Antioxidative, Antihyaluronidase and Antityrosinase Activities of Some Constituents from the Aerial Part of Piper elongatum VAHL.

Masuoka

Ono

Ito

et al. 2003

FSTR

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Seven known compounds, pyrroside B (1), swertisin (2), isovitexin (3), isoswertiajaponin (4), vomifoliol (blumenol A) (5), (6S,9R)-roseoside (6) and angelicoidenol (7) were isolated from the methanol (MeOH) extract of the aerial part of Piper elongatum VAHL. and their structures were identified on the basis of physical and spectral data. In addition, the antioxidative activity of 1-4 was evaluated by the ferric thiocyanate method. All these compounds showed stronger antioxidative activity than that of ␣-tocopherol. Furthermore, the scavenging effects on 1,1-diphenyl-2-picrylhydrazyl (DPPH), the antihyaluronidase and the antityrosinase activities of 1-4, asebogenin (8), 2¢ ¢ ¢ ¢,6¢ ¢ ¢ ¢-dihydroxy-4¢ ¢ ¢ ¢-methoxydihydrochalcone (9), 3-geranyl-4-methoxybenzoic acid (10), 3-geranyl-4-hydroxybenzoic acid (11), nervogenic acid (12) and 2,2-dimethyl-6-carboxyl-8-prenyl-chromene (13), which were previously isolated from the MeOH extract were evaluated. Compounds 4, 8 and 9 showed higher radical scavenging effect than that of L-cysteine, and 4, 8 and 11 exhibited stronger inhibition effect on the activation of hyaluronidase than that of tranilast. Compound 8 indicated almost the same antityrosinase activity as that of kojic acid.

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“…The fraction eluted with MeOH was repeatedly chromatographed on columns of silica gel, . Fifteen were identified as known compounds; verbascoside (1), isoverbascoside (2), leucosceptoside A (3) (Miyase et al, 1982), luteoside A (6), luteoside B (7) (Kernan et al, 1998), 2 00 -O-apiosylverbascoside (8) (Kanchanapoom et al, 2001), decaffeoylverbacoside (9) (Karasawa et al, 1986), seguinoside K (10) (Zhong et al, 1999) (Achenbach et al, 1992) (Binns et al, 1987), (6S,9R)-roseoside (17) (Otsuka et al, 1995) rengyoside B (18) (Seya et al, 1989) and stegioside III (19) (Nass and Rimpler, 1996) by comparison of physical data with literature values and from spectroscopic evidence.…”

Section: Resultsmentioning

confidence: 99%