Alangionosides CF, megastigmane glycosides from Alangium premnifolium

Otsuka, Hideaki; Kamada, Kenji; Yao, Masami; Yuasa, Kaori; Kida, Ikuko; Takeda, Yoshio

doi:10.1016/0031-9422(94)00830-m

Cited by 29 publications

(19 citation statements)

References 7 publications

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“…The absolute configuration at C-9 of 3 was assigned to be R from the chemical shifts at C-9 and C-10 (77.4 and 21.0, respectively) (Pabst et al, 1992;Takeda et al, 1997). Also, the absolute configurations at C-9 of 1 and 2, which could not be determined from the previous reports (Uchiyama et al, 1989;Otsuka et al, 1995), were concluded to be R. Consequently, the structure of compound 3 was elucidated as shown, named ebracteatoside A.…”

Section: Resultsmentioning

confidence: 90%

“…HPLC to afford 27 compounds. Twenty two were identified as known compounds; plucheoside B (1), alangionoside C (2) (Otsuka et al, 1995), premnaionoside (4) (Sudo et al, 2000), (2R)-2-O-b-d-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc, 8) (Tietze et al, 1991), (2R)-2-O-b-d-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA-Glc, 9) (Hartenstein and Sicker, 1994) (Ono et al, 1999) (Okamura et al, 1981), adenosine (13) (Otsuka et al, 1989), verbascoside (14), isoverbascoside (15), leucosceptoside A (16) (Miyase et al, 1982), martynoside (17) (Sasaki et al, 1978), b-hydroxyacteoside (18) (Kitakawa et al, 1984), vecenin-2 (19), schaftoside (20) (Markham and Chari, 1982) (Hase et al, 1995) (Achenbach et al, 1992) (Ida et al, 1994), magnolenin C (26) (Rao and Wu, 1978), and ( (Kinjo et al, 1991) by comparison of physical data with literature values and from spectroscopic evidence.…”

Section: Resultsmentioning

confidence: 99%

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Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

et al. 2001

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

et al. 2001

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“…All the spectroscopic and physical data suggested that 7 was also a megastigmane glucoside, whose ring system bore two hydroxy substitutents at C-3 and C-4 like plucheoside B (10), isolated from Pluchea indica 8) and Alangium premnifolium. 9) However, the double bond on the side chain was reduced to methylenes. The orientations of the two hydroxy substituents were deduced to be equatorial and axial, respectively, from the coupling constants of H-3 (d H 3.99, dt, J H2ax-H3 ϭ13 Hz and J H3-H4 and H2eq ϭ4 Hz) and H-4 (d H 4.05, br d, J H3-H4 ϭ4 Hz).…”

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confidence: 99%

Turpinionosides A-E: Megastigmane Glucosides from Leaves of Turpinia ternata Nakai.

Qian

Otsuka

Hirata

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Megastigmane glycosides are now an expanding class of compounds and their relatively wide distribution in plant kingdom has been reported. In a previous work, 1) a megastigmane was isolated as a non-glycosidic form from Euscaphis japonica and its absolute configuration was determined by the modified Mosher's method. Leaves of Turpinia ternate collected in Okinawa also afforded one megastigmane (1) and seven megastigmane glycosides (2-8). The structure of the megastigmane (1) was elucidated to be the same as that of that isolated from E. japonica, including absolute configurations. Compounds 2 and 3 were found to be known compounds, corchoionoside C 2) and icariside B 4 , 3) respectively. The structures of the remaining megastigmane glucosides were elucidated by NMR spectroscopic analyses and the absolute configurations of turpinionosides A-E (4-8) were elucidated in this work by the modified Mosher's method. Results and DiscussionMegastigamane (1) and megastigamane glucosides (2-8) were isolated from the n-BuOH-soluble fraction of a MeOH extract of leaves of Turpinia ternata by means of a combination of several kinds of chromatographic methods, and details being given in the experimental section. The structures of other known compounds (2, 3) were identified by comparison of spectroscopic data with those reported.Compound 1, C 13 H 24 O 4 , was isolated as a syrup and its planar structure was elucidated to be the same as that of the megastigamane isolated from a related plant, Euscaphis japonica.1) On comparison of the optical rotation values of 1 from both sources, the absolute configurations were presumed to be the same. This was confirmed by that compound 1 from the title plant was also determined with the modified Mosher's method 4) to have the 3S, 5R, 6R and 9S configurations (Fig. 1).Turpenionoside A (4), [a] D 22 Ϫ38.4°, was isolated as an amorphous powder and its elemental composition was determined to be C 19 H 34 O 8 by negative-ion high-resolution (HR) FAB-MS. The IR spectrum of 4 showed a strong absorption band at 3401 cm Ϫ1 suggestive of a glycosidic structure. The 1 H-and 13 C-NMR spectra of 4 showed signals attributable to a b-glucopyranosyl unit, and two tertiary methyls at a geminal position, two secondary methyls, two methylenes, one methine without and two methines with hydroxyl groups, one disubstituted trans double bond, and two quarternary carbon atoms with and without a hydroxyl group, respectively. These functionalities were the same as those of megastigmane glucoside, dendranthemoside A (9) ([a] D 22 Ϫ44.2°), isolated from Dendranthema shiwogiku, 5) and the NMR spectroscopic data of 4 and 9 were essentially indistinguishable from each other. The absolute structure for 9 has been determined by Xcrystallographic analysis of its pentaacetate to have the 3S, 5R, 6S and 9R configurations.6) Since most glucose in Nature is of the D-series, the b-D-glucosylation-induced shift-trend in the 13 C-NMR spectroscopy was applied for the elucidation of absolute configuration. 7) On b-D-glucosylation o...

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“…platanifolium (Fukuoka Prefecture, Japan) (141,142). The leaves of Alangium premnifolium (Japanese name: Shima-urinoki) from Nakagamigun (Okinawa Prefecture) were found to contain 191, 194-196, 241-243 (143), and 212-217 (144) glycosides. Myrsine seguinii (syn.…”

Section: Norisoprenoid Glycosidesmentioning

confidence: 98%

“…Otsuka and co-workers (141)(142)(143)(144)(145)(146) have studied Japanese plants belonging to several genera and have isolated many different norisoprenoid compounds. The megastigmane (ionol-type) glycosides 158-163, 164-166, 215, 218-221, 226-228, and 252 were identified from the butanol-soluble fraction of the leaves of Alangium platanifolium var.…”

Section: Norisoprenoid Glycosidesmentioning

confidence: 99%

Astonishing diversity of natural surfactants: 3. Carotenoid glycosides and isoprenoid glycolipids

Dembitsky

2005

Lipids

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Carotenoid glycosides and isoprenoid glycolipids are of great interest, especially for the medicinal, pharmaceutical, food, cosmetic, flavor, and fragrance industries. These biologically active natural surfactants have good prospects for the future chemical preparation of compounds useful as antimicrobial, antibacterial, and antitumor agents, or in industry. More than 300 unusual natural surfactants are described in this review article, including their chemical structures and biological activities.

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Alangionosides CF, megastigmane glycosides from Alangium premnifolium

Cited by 29 publications

References 7 publications

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

Megastigmane, aliphatic alcohol and benzoxazinoid glycosides from Acanthus ebracteatus

Turpinionosides A-E: Megastigmane Glucosides from Leaves of Turpinia ternata Nakai.

Astonishing diversity of natural surfactants: 3. Carotenoid glycosides and isoprenoid glycolipids

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