Two new ent-kaurane diterpenoids fromPteris semipinnata

Abstract

In this study, two new compounds and six known compounds were isolated from the aerial parts of Pteris semipinnata. The chemical structures of these two new compounds were elucidated as 6β,11α-dihydroxy-15-oxo-ent-kaur-16-en-19-oic acid (1) and 7α,11α-dihydroxy-15-oxo-ent-kaur-16-en-19-oic acid (2) by the extensive spectral methods including 2D NMR and HR-MS techniques.

Phytochemicals from fern species: potential for medicine applications

“…Phytochemical studies on this species have led to the isolation of over thirty terpenoids, including diterpenoids and sesquiterpenoids. Most of the novel diterpenoids from P. semipinnata are ent-kaurane derivatives such as 6β,11α-dihydroxy-15-oxo-ent-kaur-16-en-19-oic acid and 7α,11α-dihydroxy-15-oxo-ent-kaur-16-en-19oic acid (Bai et al 2013), 7 β-hydroxy-11β,16β-epoxyent-kauran-19-oic acid (Zhan et al 2009), and pterisolic acids A-F (Wang et al 2011a, b, c). In addition, a new ent-kaurane diterpenoid glucoside known as pteriside has been obtained from P. semipinnata (Shi and Bai Murakami et al (1985a, b), Murakami and Tanaka (1988) 2β,16α-Dihydroxy-ent-kaurane 2-O-β-Dglucoside P. angustipinna, P. cretica, P. dactylina, P. multifida Murakami et al (1985a, b), Murakami and Tanaka (1988) 2β,6β,16α-Trihydroxy-ent-kaurane P. cretica Murakami et al (1985a, b), Murakami and Tanaka (1988) 2β,6β,16α-Trihydroxy-ent-kaurane 2-O-β-Dglucoside P. cretica Murakami and Tanaka (1988) 2β,16α,18-Trihydroxy-ent-kaurane P. ryukyuensis Tanaka et al (1978) 2β,15α,16α,17-Tetrahydroxy-ent-kaurane P. cretica Murakami and Tanaka (1988) 2β,14β,15α,16α,17-pentahydroxy-entkaurane P. cretica Murakami and Tanaka (1988) 11β,16β-Epoxy-ent-kauran-19-oic acid P. longipes Murakami et al (1981) Murakami et al (1985a, b), Murakami and Tanaka (1988), Liu and Qin (2002) 2β,15α-Dihydmxy-ent-kant-16-ene 2-O-β-Dglucoside P. angustipinna, P. cretica, P. dactylina, P. multifida, P. plumbaea Murakami et al (1985a, b), Murakami and Tanaka (1988) 2β,16β,15α-Trihydroxy-ent-kaur-16-ene P. cretica, P. multifida Murakami and Tanaka (1988), Liu and Qin (2002) 2β,6β,15α-trihydroxy-ent-kaur-16-ene 2-O-β-D-glucoside P. cretica Murakami and Tanaka (1988) 2β,14β,15α-Trihydroxy-ent-kaur-16-ene P. plumbaea Murakami and Tanaka (1988) 2β,14β,15α-Trihydroxy-ent-kaur-16-ene 2-Oβ-D-glucoside P. plumbaea Murakami and Tanaka (1988) 2β,6β,14β,15α-Tetrahydroxy-ent-kaur-16-ene P. plumbaea Murakami and Tanaka (1988) 2β,13,14β,15α-Tetrahydroxy-ent-kaur-16-ene P. plumbaea Murakami and Tanaka (1988)…”

Diterpenoids of terrestrial origin

“…C, 48). 131 Further ent-kaurenes, including 49, have been obtained 132 from Pteris semipinnata, whilst the graecumosides A and B (e.g. A, 50) are glycosides which were isolated 133 from fenugreek seeds (Trigonella foenum-graecum, Fabaceae).…”

Medicinal pteridophytes: ethnopharmacological, phytochemical, and clinical attributes

“…The pharmacological applications of members of the Pteridaceae have been cited in tribal medicine. Researchers have isolated a variety of bioactive compounds from the family Pteridaceae, including alkaloids, flavonoids, and derivatives of their glucosides including kaurene, kauroic acid, apigenin, caffeic acid, rutin, luteolin, ptaquiloside, and pterosine [5,178]. The cognitive symptoms of Alzheimer's disease can be alleviated with acetylcholinesterase inhibitors.…”