ent-Kaurane diterpenoids from the plant Wedelia trilobata

Abstract

Abstract:Four new ent-kaurane diterpenoids, namely, 3α-tigloyloxypterokaurene L 3 (1), ent-17-hydroxy-kaura-9(11),15-dien-19-oic acid (2), and wedelobatins A (3) and B (4), together with 11 known ent-kaurane diterpenoids (5-15), were isolated from the ethanol extract of Wedelia trilobata. All the structures of 1-15 were elucidated on the basis of spectroscopic studies.

Two New Compounds from Wedelia chinensis and Their Anti‐inflammatory Activities

“…Thirteen known compounds were identified as 3 α ‐tigeloyloxy‐9 β ‐hydroxy‐ ent ‐ kaura ‐16‐ en ‐19‐oic aicd ( 3 ), 4, 5‐di‐ O ‐caffeoyl ‐ quinic acid methyl ester ( 4 ), 3,4‐di‐ O ‐caffeoylquinic acid methyl ester ( 5 ), 3,4‐di‐ O ‐caffeoylquinic acid butyl ester ( 6 ), 3‐ O ‐caffeoylquinic acid butyl ester ( 7 ), methyl caffeate ( 8 ), epifriedelanol ( 9 ), β ‐D‐glucopyranosyl‐3‐ O ‐[ β ‐D‐xylopyranosy‐l‐(1→2)‐ β ‐D‐glucuronopyranosyl] oleanolate ( 10 ), stigmasterol ( 11 ), stigmasterol‐3‐ O ‐ β ‐D‐glucopyranoside ( 12 ), kaempfer‐ ol‐3‐ O ‐ β ‐D‐glucopyranoside ( 13 ), 7‐methoxyl‐kaempferol‐3‐ O ‐ β ‐D‐glucopyranoside ( 14 ), isoquercetin‐3‐ O ‐ β ‐D‐glucoside ( 15 ) by comparing their MS, NMR, and specific rotation data with those of related compounds in literatures.…”

Absolute Structures of Wedelolide Derivatives and Structure–Activity Relationships of Protein Tyrosine Phosphatase 1B Inhibitory <i>ent</i>-Kaurene Diterpenes from Aerial Parts of <i>Wedelia</i> spp. Collected in Indonesia and Japan

“…12,13) In this study, the remaining fractions were further separated with an octadecyl silane (ODS) column followed by preparative HPLC (ODS) to give compounds 10 (3. The structures of compounds 10-19 were identified as ent-3β-angeloyloxykaur-16-en-19-oic acid, 18) ent-3βtigloyloxykaur-16-en-19-oic acid, 18) 3α-cinnamoyloxypterokaurene L 3 , 18) pterokaurene L 3 , 19) 3α-angeloyloxypterokaurene L 3 , 18) 3α-tigloyloxypterokaurene L 3 , 20) ent-kaur-9(11),16dien-19-oic acid, 21) ent-17-hydroxykaur-15-en-19-oic acid, 22) tetrachyrin, 23) and 15-hydroxykaur-9(11),16-dien-19-oic acid, 22) respectively, by comparing their spectroscopic data with reported values (Fig. 1).…”

“…1). Further bioassayguided separation afforded ten more ent-kaurene diterpene derivatives (10)(11)(12)(13)(14)(15)(16)(17)(18)(19) (Fig. 1) from the remaining fractions of the Indonesian W. prostrata.…”

Evaluation of Pharmacognostic, Phytochemical and Physicochemical Standards of Wedelia Trilobata (L.) Root

“…Seed production is low and generally does not reproduce prolifically via seed [4]. It really is utilized by Indians as traditionally in the treatment of backache, muscle cramp, rheumatism, stubborn wounds, sores, swelling and arthritic pain, fever and malaria [5][6][7]. So far, phytochemical studies have revealed some structurally diverse chemicals from this plant, including terpenoids (sesqui-, diter-, and triterpenoids), steroids, flavonoids and phenolics, some of which showed significant bioactivities [7][8][9][10][11][12][13].…”

“…It really is utilized by Indians as traditionally in the treatment of backache, muscle cramp, rheumatism, stubborn wounds, sores, swelling and arthritic pain, fever and malaria [5][6][7]. So far, phytochemical studies have revealed some structurally diverse chemicals from this plant, including terpenoids (sesqui-, diter-, and triterpenoids), steroids, flavonoids and phenolics, some of which showed significant bioactivities [7][8][9][10][11][12][13]. Numerous pharmacological activities of W. trilobata offers been reported such as antimicrobial [14], Antioxidant [15], Anti-inflammatory [15], wound healing [16], Anthelmintic [17] and anticancer [15].…”