Protostane‐Type Triterpenoids from Alisma orientale

Abstract

Twenty-eight protostane triterpenoids, including a new degraded one (1), nine new ones (2 - 10), and two new natural ones (11 and 12), have been isolated from the dried rhizomes of Alisma orientale. Alisol R (1) was the first 20,21,22,23,24,25,26,27-octanorprotostane triterpenoid. The absolute configurations of 25-methoxyalisol F (2) and 16β-hydroperoxyalisol B 23-acetate (3) were determined by X-ray diffraction analysis. In addition, alismaketone-B 23-acetate (28) showed potent vasorelaxant activity on endothelium-intact thoracic aorta rings precontracted with KCl.

Triterpenoids from Alisma orientale and their NF-кB Inhibitory Activity

“…In this study, 15 protostane-type triterpenoids (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15), including a new triterpenoid, alismaketone B (1), and a new natural nortriterpene, noralisolic acid A (2), as well as a known fatty acid compound (16), were identified from A. orientale's rhizomes (▶ Fig. 1).…”

“…This plant's dried tubers (Rhizoma alismatis), known as "Zexie" in China [1], are often used in clinics for eliminating dampness, reducing edema, and promoting diuresis [2,3]. Triterpenes [4,5] and sesquiterpenes [6] are the major components in A. orientale tubes. Pharmacological studies showed that this plant's ethanol or water extracts have diuretic [7], lipid-lowering [8], liver-protecting [9], e114…”

Alisma genus: Phytochemical constituents, biosynthesis, and biological activities

“…Li et al also investigated A. orientale and identified 12 new triterpenes, including alisol R ( 34 ), 25‐methoxyalisol F ( 35 ), 16 β ‐hydroperoxyalisol B 23‐acetate ( 36 ), alisol S 23‐acetate ( 37 ), 16 β ‐hydroperoxyalisol B ( 38 ), 16 β ‐methoxyalisol B ( 39 ), 16 β ‐methoxyalisol E ( 40 ), 16 β ,25‐ dimethoxyalisol E ( 41 ), 16 β ‐hydroperoxyalisol E ( 42 ), alisol T ( 43 ), and two natural triterpenoids alisols U ( 43 ) and V ( 44 ). Among them, alisol R ( 34 ) was an unusual 20,21,22,23,24,25,26, 27‐octanorprotostane triterpenoid (Li et al, 2017b).…”

Triterpenoids From Alisma Species: Phytochemistry, Structure Modification, and Bioactivities

“…Carbonyl groups substitute at C-16 (8, 9) (Zhao et al, 2015), disubstitute at C-7/C-16 (41) (Mai et al, 2015) or C-16/C-23 (21) (Yoshikawa et al, 1999), or substitute at C-24 (37) (Xu et al, 2012) or C-23 (23) (Yi et al, 2019). Hydroxymethyl groups substitute at C-16 (18) (Li et al, 2017) or disubstitute at C-16/C-25 (19).…”