Iridoid and phenolic diglycosides from Canthium berberidifolium

Kanchanapoom, Tripetch; Kasai, Ryoji; Yamasaki, Kazuo

doi:10.1016/s0031-9422(02)00140-1

Cited by 52 publications

(36 citation statements)

References 9 publications

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“…The 9) The remaining carbon signals belonged to the sugar part, and were identified as b-apiofuranosyl-(1→6)-b-glucopyranosyl unit by comparing chemical shifts with the reported data. 9) All protonated carbons were assigned by the results from heteronuclear single quantum coherence (HSQC) and heteronuclear multiple-bond connectivity (HMBC) spectra. Enzymatic hydrolysis of 1 with crude hesperidinase gave 2,4-dihydroxy-6-methoxy-acetophenone (1a), identified by 1 H-and 13 C-NMR spectral analysis, 10) in addition to the sugar fraction from the aqueous layer.…”

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confidence: 99%

Acetophenone Diglycosides from Erythroxylum cambodianum

Kanchanapoom

Noiarsa

Tiengtham

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Erythroxylum cambodianum PIERRE (Erythroxylaceae, Thai name: Huun-Hai) is a shrub that grows up to 1.5 m high, distributed in Northeastern Thailand. It is used in Thai traditional medicine for anti-fever purposes, as well as an anti-inflammatory agent. In the course of our continuing studies on Thai medicinal plants, the constituents of this plant were investigated. To the best of our knowledge, no phytochemical study has been carried out on this species. However, previous phytochemical investigation of plants in this genus showed the presence of alkaloids, flavonoids and triterpenoids.1-4) The present paper deals with the isolation and structural determination of seven compounds, including two new acetophenone glycosides (1, 2), two known flavans (3, 4), one known flavonol glycoside (5), and two known megastigmane glucosides (6, 7) from the aerial portion of this plant. Results and DiscussionThe methanolic extract was suspended in H 2 O and defatted with Et 2 O. The n-BuOH soluble fraction was subjected to a Diaion HP-20 column, using H 2 O, 50% aqueous MeOH, MeOH and Me 2 CO successively. The portion eluted with MeOH was repeatedly chromatographed on columns of silica gel, RP-18, and preparative HPLC-ODS to afford 7 compounds. Five were identified as the known compounds (ϩ)-and citroside A (7), 8) by comparison of physical data with values reported in the literature and from spectroscopic evidence.Erythroxyloside A (1) was isolated as an amorphous powder, and determined to be C 20 H 28 O 13 by negative high-resolution (HR)-FAB mass spectrometry. The 9) The remaining carbon signals belonged to the sugar part, and were identified as b-apiofuranosyl-(1→6)-b-glucopyranosyl unit by comparing chemical shifts with the reported data. 9)All protonated carbons were assigned by the results from heteronuclear single quantum coherence (HSQC) and heteronuclear multiple-bond connectivity (HMBC) spectra. Enzymatic hydrolysis of 1 with crude hesperidinase gave 2,4-dihydroxy-6-methoxy-acetophenone (1a), identified by 1 H-and 13 C-NMR spectral analysis, 10) in addition to the sugar fraction from the aqueous layer. The stereochemistry of an apiose could be assigned as D-form by the coupling of H-5Љ at d H 3.54, which showed the magnetic equivalent.11) The absolute configuration of a glucose was determined as D-form by treating the sugar fraction with L-cysteine methyl ester in pyridine to provide the thiazolidine derivatives of sugars, and then comparing the Rf values with the standard sample of thiazolidine derivative of D-glucose [methyl 2-(D-gluco-pentahydroxypentyl)-thiazolidine-4(R)-carboxylate], which was prepared by the previously reported method (see Experimental).12,13) Two spots of the derivative from D-glucose were found on TLC (Rf: 0.42, 0.49), due to the C-2 epimers of thiazolidine derivatives. The location of the sugar moiety was Two new acetophenone diglycosides, erythroxylosides A and B, were isolated from the aerial portion of Erythroxylum cambodianum together with (؉)-catechin, (؊)-epicatechin, quercetin 3-O-rut...

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Acetophenone Diglycosides from Erythroxylum cambodianum

Kanchanapoom

Noiarsa

Tiengtham

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…(Rubiaceae, Thai name: Ya-Khamen) is a small herb found in the tropical regions of Asia. In the course of our continuing studies on Rubiaceous plants [1][2][3][4][5], the constituents of this plant were investigated, following plant collected from Khon Kaen University, Thailand. The phytochemical study has not been reported on this species.…”

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confidence: 99%

(Z)-3-Hexenyl diglycosides from Spermacoce laevis Roxb.

et al. 2007

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A new (Z)-3-hexenyl O-b-D-glucopyranosyl-(1 fi 6)-b-D-glucopyranoside was isolated from the aerial part of Spermacoce laevis, along with 17 known compounds:phenyethyl O-a-L-rhamnopyranosyl-(1 fi 6)-b-D-glucopyranoside, benzyl O-a-Larabinopyranosyl-(1 fi 6)-b-D-glucopyranoside, benzyl O-b-D-xylopyranosyl-(1 fi 6)-b-D-glucopyranoside, asperuloside, 6a-hydroxyadoxoside, asperulosidic acid, kaempferol 3-O-b-D-glucopyranoside, kaempferol 3-O-rutinoside, quercetin 3-O-b-D-galactopyranoside, quercetin 3-O-a-L-rhamnopyranosyl-(1 fi 6)-b-D-galactopyranoside, and rutin. The structure determinations were based on physical data and spectroscopic evidence.

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“…The bark is used in Thai traditional medicine for antipyretic purposes, as well as an antiinflammatory agent. In the part of our ongoing studies on Thai Rubiaceous plants [1][2][3][4], the constituents of this plant were investigated. In the previous study, anthraquinones have been reported [5].…”

Section: Introductionmentioning

confidence: 99%

A new iridoid glucoside from the Thai medicinal plant, Morinda elliptica Ridl

et al. 2006

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A new plumieride type iridoid glucoside, morinipticoside, was isolated from the leaves and branches of Morinda elliptica together with six known compounds; asperuloside, asperulosidic acid, yopaaoside A, yopaaoside B, benzyl a-L-arabinopyranosyl (1 fi 6)-b-D-glucopyranoside and phenyethyl a-L-arabinopyranosyl(1 fi 6)-b-D-glucopyranoside. The structure determinations were based on physical data and spectroscopic evidence.

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Iridoid and phenolic diglycosides from Canthium berberidifolium

Cited by 52 publications

References 9 publications

Acetophenone Diglycosides from Erythroxylum cambodianum

Acetophenone Diglycosides from Erythroxylum cambodianum

(Z)-3-Hexenyl diglycosides from Spermacoce laevis Roxb.

A new iridoid glucoside from the Thai medicinal plant, Morinda elliptica Ridl

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