Anthraquinone glycosides from rhynchotechum VESTITUMfn2fn2Part 3 in the series Chemical studies of Chinese medicinal plant Rhynchotechumvestitum. For part 2 see ref. [2].

Yang, Lü; Xu, Pei-Juan; Chen, Ze-Nai

doi:10.1016/s0031-9422(98)00079-x

Cited by 23 publications

(9 citation statements)

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“…3) Several significant differences involving the d C values of 1 were noted: 1) C-11 was shifted to a higher field (d C 52.66, cf. d C 59.2 for reference) and C-2 to a lower field (d C 132.31, cf.…”

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Three New and Antitumor Anthraquinone Glycosides from Lasianthus acuminatissimus MERR.

Zhang

Luo

et al. 2006

Chem. Pharm. Bull.

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Lasianthus acuminatissimus MERR. is a plant of the Rubiaceae family, distributed in the southern provinces of China. It is used in traditional Chinese folk medicine for the treatment of rheumatoid arthritis. However, the investigations on the chemical constituents of plant have been few, studies were limited to species taxonomy, and no compound was reported.1,2) In a search for the active constituents in the treatment of rheumatoid arthritis, the acetone extract of the roots was chromatographed on a silica gel column, and the obtained eluates were subjected to chemical investigation leading to the isolation and the structural elucidation of three new anthraquinone glycosides, lasianthuoside A (1), B (2), and C (3). Ten known compounds, damnacanthol (4), 3,4) damnacanthol 11-methyl ether (5),3) asperuloside (7), 6) asperulosidic acid (8), 6) deacetyl asperulosidic acid (9), 6) a nonglycosidic iridoid (10), 7) 2,6-dimethoxy-4-hydroxyphenol-1-O-b -D-glucopyranoside (11), 8) tachioside (12), 9) and isotachioside (13) 9) are also reported for the first time from this plant. In addition to a preliminary evaluation in treating rheumatoid arthritis, we found that the iridoid glycosides are the bioactive compounds of the plant. The antitumor activity of six anthraquinones against human 2780 cells was also evaluated, and the three new anthraquinone glycosides showed significant bioactivity.The HR-FAB mass spectrum of compound 1 showed a molecular ion at m/z 469.1087 (Calcd 469.1111) which corresponded to C 22 H 22 O 10 Na [MϩNa], while the UV maxima at 203.2, 267.0, and 358.0 nm and IR bands at 3510, 1670, and 1577 cm Ϫ1 suggested the presence of a hydroxyanthraquinone. A singlet signal at d H 3.87 (3H, s), an AB spin system at d H 4.58 and 4.67 (each H, d, Jϭ11.0 Hz), and the signals at d C 161.52 and 161.37 (two oxygenated aromatic carbons) and d C 52.66 (one oxygenated secondary aliphatic carbon) indicated an anthraquinone aglycone with three substituents, a methoxy, a phenolic hydroxyl, and a hydroxymethyl in the 1 H-NMR and 13 C-NMR spectra. Furthermore, the carbon signals of the glycosyl group suggested a glucose residue attached to one of the hydroxyls. Four aromatic protons in a symmetrical AAЈBBЈ-type pattern indicated that one aromatic ring in the anthraquinone was unsubstituted, and one isolated aromatic proton at d H 7.74 exhibited crosspeaks with the carbons at 132.31 (C-2), 161.52 (C-3), 121.19 (C-9a), and 182.77 (C-10) in HMBC, indicating that the other ring was unsubstituted at C-4 and substituted at C-1, C-2, and C-3.Most anthraquinones isolated from the Rubiaceae have no substituent in one aromactic ring and always have a carbon substituent at position 2 in the other ring.3) Therefore the hydroxymethyl group in 1 was placed at C-2 on comparative and biogenetic grounds, consistent with the HMBC data. The hydroxymethyl proton signals at d H 4.58 and 4.67 exhibited cross-peaks with the carbons at 161.37 (C-1), 132.31 (C-2), 161.52 (C-3), and 63.42 (MeO) further comfirming that they are linked to C-2. The si...

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Three New and Antitumor Anthraquinone Glycosides from Lasianthus acuminatissimus MERR.

Zhang

Luo

et al. 2006

Chem. Pharm. Bull.

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“…By comparison of these data with the published data of rubiadin 3-O-b-primeveroside, the sugar portion was deduced to be primeverosyl moiety (xylosyl-(1→6)-O-glucose). 18) This was supported by downfield shift of the glucosyl C-6Ј to d C 68.7. To further confirm this proposal, 2 was hydrolyzed with 2 N HCl (aq) to afforded 1,3-dihydroxy-2-hydroxymethyl anthraquinone 19) from an organic layer.…”

Section: Resultsmentioning

confidence: 88%

Anthraquinones from Ophiorrhiza hayatana OHWI

Chan

Damu

2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A combination of column chromatography followed by further purification led to the isolation of two new bis-iridoid glucosides (1 and 2) and a new iridoid glucoside (3) from the leaves, and seven new anthraquinones (4-10) from the stems, in addition to three known compounds identified as 6-O-acetylscandoside, 4) lucidin 3-O-b-primeveroside, 5) and damnacanthol 3-O-bprimeveroside. 6) The 1 H-and 13 C-NMR spectra (Table 1) of compound 1 showed two sets of almost superimposable signals (16 carbons each), including signals from two glucopyranosyl moieties attributable to two iridoid glucoside units, indicating that 1 was a bis-iridoid glucoside.…”

Section: Resultsmentioning

confidence: 99%

“…These assignments were in agreement with those published for the sugar moieties of lucidin 3-O-b-primeveroside and damnacanthol 3-O-bprimeveroside. 5,6) Therefore, the identity of 5 was established as 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b-primeveroside. Compound 6 had a very similar structure to 5 including the primeverosyl moiety.…”

Section: Iridoids and Anthraquinones From The Malaysian Medicinal Plamentioning

confidence: 99%

Iridoids and Anthraquinones from the Malaysian Medicinal Plant, Saprosma scortechinii(Rubiaceae).

Ling

Komorita

Tanaka

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Saprosma scortechinii BL. KING & GAMBLE, a rubiaceous plant endemic in the Malay Peninsula, 1) is also known as 'sekentut', a local name associated with the unpleasant and fetid odor emitted by the bruised plant tissues. In the traditional medicinal system of Malaysia, the roots are employed in decoctions to treat fever by the native communities, while the young leaves are also eaten as a vegetable.2) Our previous studies on the plant have resulted in the isolation of six sulfur-containing bis-iridoid glucosides (saprosmosides A-F) and 13 iridoid glucosides.3) On-going studies on the same plant materials have resulted in the isolation of two new bisiridoid glucosides, a new iridoid glucoside, and seven new anthraquinones, in addition to three known compounds. We wish to report herein the isolation and structural elucidation of these compounds. Results and DiscussionDried leaves and stems were separately extracted with methanol, and the resulting extracts were subjected to solvent-solvent partitioning. A combination of column chromatography followed by further purification led to the isolation of two new bis-iridoid glucosides (1 and 2) and a new iridoid glucoside (3) from the leaves, and seven new anthraquinones (4-10) from the stems, in addition to three known compounds identified as 6-O-acetylscandoside, The 1 H-and 13 C-NMR spectra ( ; 8-19-1 Nanakuma, Jyounanku, Fukuoka 814-0180, Japan. Received February 18, 2002; accepted May 8, 2002 A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b b-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-b b-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-b b-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.

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Anthraquinone glycosides from rhynchotechum VESTITUMfn2fn2Part 3 in the series Chemical studies of Chinese medicinal plant Rhynchotechumvestitum. For part 2 see ref. [2].

Cited by 23 publications

References 5 publications

Three New and Antitumor Anthraquinone Glycosides from Lasianthus acuminatissimus MERR.

Three New and Antitumor Anthraquinone Glycosides from Lasianthus acuminatissimus MERR.

Anthraquinones from Ophiorrhiza hayatana OHWI

Iridoids and Anthraquinones from the Malaysian Medicinal Plant, Saprosma scortechinii(Rubiaceae).

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