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

Abstract

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.

Chemical Constituents from Leaves of <i>Hydrangea serrata</i> and Their Anti-photoaging Effects on UVB-Irradiated Human Fibroblasts

“…10) To date, a number of bioactive compounds such as dihydroisocoumarins, secoiridoids, and stilbenes (hydrangenol, phyllodulcin, macrophylloside, and their glucosides) have been isolated from hydrangea plants. 11,12) Phyllodulcin has been identified as the compound responsible for the sweet taste of its infusion. 7) Hydrangea serrata (THUNB.)…”

Two New Cyanogenic Glucosides from the Leaves of Hydrangea macrophylla

“…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].…”

Oral Intake of Hydrangea serrata (Thunb.) Ser. Leaves Extract Improves Wrinkles, Hydration, Elasticity, Texture, and Roughness in Human Skin: A Randomized, Double-Blind, Placebo-Controlled Study

“…Hydrangea plants have a variety of bioactive compounds such as dihydroisocoumarins, secoiridoids, and stilbenes (hydrangenol, phyllodulcin, macrophylloside, and their glucosides) [5,6]. Among these compounds, we previously reported that hydrangenol, a dihydroisocoumarin, possesses potential protective effects on cell viability, production of procollagen type I, MMP-1, and pro-inflammatory cytokines [7].…”