A novel type secoiridoid glucoside, hydrangenoside a from Hydrangea macrophylla

Inouye, Hiroyuki; Takeda, Yoshio; Uesato, Shinichi; Uobe, Kenichi; Hashimoto, Tadanori; Shingu, Tetsuro

doi:10.1016/s0040-4039(00)78838-1

Cited by 20 publications

(16 citation statements)

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“…Next, to confirm the presumed structures of lactones 24 and 28, their syntheses were carried out in the following way [2]. The 7-bromohept-I-yl tetrahydropyran-2-yl ether (31) 1141 was converted, via 8-@-hydroxyphenyl)octan-l-o1(32), to 8-@-benzyloxyphenyl)octyl bromide (33).…”

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confidence: 99%

Studies on Monoterpene Glucosides and Related Natural Products Part 51. Absolute Structures of Hydrangenosides A, B, C, D, E, F, and G. Novel Type Secoiridoid Glucosides from Two Hydrangea Plants

Uesato

Takeda

Hashimoto

et al. 1984

Helvetica Chimica Acta

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SummaryFrom Hydrangea macrophylla var. macrophylla, four new secoiridoid glucosides, hydrangenosides A, B, C and D, were isolated, along with the known iridoid glucosides loganin, secologanin, secologanic acid and sweroside. Moreover, hydrangenosides E, F, and G, the glucosides of the same class, were isolated together with hydrangenosides C and D from Hydrangea scandens. Based on spectroscopic and chemical methods, the novel structures of the new glucosides consisting of secologanin and a shikimate-malonate-derived unit which are joined by a C-C bond were elucidated. However, seven other Hydrangea plants were tested and found not to contain hydrangenoside-type glucosides.In 1964, Plouvier reported the isolation of loganin (10) from Hydrangea aspera D. DON, H . bretschneideri DIPP., and H . xanthoneura DIELS. [5]. However, no other study has been recorded on iridoid constituents of Hydrangea species (Saxijiragaceae) since then. We thus examined glucoside constituents of H . macrophylla (THUNB.) Ser. var. macrophylla, which is known to contain hydrangenol (8) [6] and hydrangenol glucoside (9) [7], and isolated four new secoiridoid glucosides, hydrangenosides A (l), B (2), C (3), and D (4) along with the known iridoid glucosides. In addition to these, hydrangenosides E (5), F (6), and G (7) of the same type of secoiridoid glucosides were isolated together with hydrangenosides C (3) and D (4) from the congeneric plant, Hydrangea scandens (LINN. fil.) SERINGE. We have established that the seven new secoiridoid glucosides have novel structures consisting of secologanin (11) and a shikimate-malonatederived unit, which are joined by a C-C bond. This paper deals with the structure elucidation of these glucosides.

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confidence: 99%

Studies on Monoterpene Glucosides and Related Natural Products Part 51. Absolute Structures of Hydrangenosides A, B, C, D, E, F, and G. Novel Type Secoiridoid Glucosides from Two Hydrangea Plants

Uesato

Takeda

Hashimoto

et al. 1984

Helvetica Chimica Acta

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“…Ser., a Saxifragaceae plant, is widely cultivated in many countries, including China and Japan. Known biologically active components from the genus Hydrangea are dihydroisocoumarins and their glycosides [1,2,3], iridoid glycosides, secoiridoid glycosides [4,5,6], flavonoid glycoside [7] and cyanoglycosides. Pharmacology research has demonstrated that these compounds possessed many biological functions, such as antidiabetic [8], antiallergic, antimicrobial activities [2] and protective effect against rat liver injury induced by D-galactosamine [9].…”

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Two New Cyanogenic Glucosides from the Leaves of Hydrangea macrophylla

et al. 2012

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“…Plants of the genus Hydrangea (Saxifragaceae) are known to contain secoiridoid glycosides [2][3][4][5] and dihydroisocoumarins, 6,7) and some of them possess antiallergic and antimicrobial activities. 5,7) The constituents of the leaves of H. macrophylla subsp.…”

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“…8) In previous papers, we reported on the isolation of secoiridoid glycosides from the leaves of the plant. 1,9) Here, we report the isolation and structure elucidation of three new glycosides, 7-deoxyloganic acid b-D-glucopyranosyl ester (1), (3R)-hydrangenol 8,4Ј-di-O-b-D-glucopyranoside (2), and (6R,7E,9R)-megastigma-4,7-dien-3-one 9,13-di-O-b-D-glucopyranoside (3) from the leaves of the plant.…”

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confidence: 99%