The Chemical Constituents of <i>Polypodium Niponicum</i>

Shen, Tong; Wen, Cheng-Wu; Zheng, Shengping

doi:10.1002/jccs.200900093

Cited by 4 publications

(1 citation statement)

References 11 publications

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“…The analysis of its aerial parts led to the isolation of active pregnane glycosides, including hoodistanal (228, structures see Figure 16), dehydrohoodistanal (230), and hoodistanalosides (229 and 231) [160]. An ethanolic extract of Polypodium niponicum (Chinese name "Shuilonggu", samples are shown in Figure 17) contained two steroids, shuilongguine II (232) and shuilongguine III (233) [161]. Viridinrelated B-norsteroids, B-norviridiol lactone (234), and B-norviridin enol (235), both with unique unprecedented carbon skeletons, were isolated from Hymenoscyphus pseudoalbidus, a fungus responsible for ash dieback.…”

Section: B-nor Steroids and Triterpenoids Derived From Terrestrial So...mentioning

confidence: 99%

Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application

Dembitsky

2024

Preprint

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The main focus of this review is to introduce readers to the fascinating class of lipid molecules known as norsteroids, exploring their distribution across various biotopes and their biological activities. The review provides an in-depth analysis of various modified steroids, including A, B, C, and D-norsteroids, each characterized by distinct structural alterations. These modifications, which range from the removal of specific methyl groups to changes in the steroid core, result in unique molecular architectures that significantly impact their biological activity and therapeutic potential. The discussion on A, B, C, and D-norsteroids sheds light on their unique configurations and how these structural modifications influence their pharmacological properties. The review also presents examples from natural sources that produce a diverse array of steroids with distinct structures, including the aforementioned A, B, C, and D-nor variants. These compounds, sourced from marine organisms like sponges, soft corals and starfish, as well as terrestrial entities such as plants, fungi, and bacteria. The exploration of these steroids encompasses their biosynthesis, ecological significance, and potential medical applications, highlighting a crucial area of interest in pharmacology and natural product chemistry. The review emphasizes the importance of researching these steroids for drug development, particularly in addressing diseases where conventional medications are inadequate or for conditions lacking sufficient therapeutic options. Examples of norsteroid synthesis are provided to illustrate the practical applications of this research.

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Section: B-nor Steroids and Triterpenoids Derived From Terrestrial So...mentioning

confidence: 99%

Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application

Dembitsky

2024

Preprint

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Coumaric Acid Glucosides from the Chinese Fern Polypodium hastatum

et al. 2016

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Phytochemical investigations on Polypodium hastatum have led to the isolation of three isomers of coumaric acid glucosides. Their structures were identified as trans-melilotoside (1), trans-coumaric acid-3-O-E-Dglucopyranoside (2), and trans-coumaric acid-4-O-E-D-glucopyranoside (3) by spectroscopic analysis. Compound 2 is a new natural product.Keywords: coumaric acid glucoside, structure elucidation, Polypodium. Polypodium hastatum Thunb. (Polypodiaceae) is a fern that belongs to the genus Polypodium and grows in most areas of China. In Chinese folk medicine, it is used as a phytomedicine for the treatment of urinary diseases. Previous phytochemical investigations on the genus revealed that there were triterpenoids [1], diterpenoids [2], steroids [2], flavonoids [2], polyphenols [2], and fatty acid derivatives [3]. But to the best of our knowledge, only a coumarin was identified by Suzuki from the leaves of P. hastatum growing in Japan [4] before our investigation. In our program to discover bioactive natural products from ferns, a phytochemical investigation of this plant was carried out, and some flavonoids have been obtained [5,6]. Herein we report the isolation and structure elucidation of coumaric acid glucosides from P. hastatum.Compound 2 was obtained as white crystals. The ferric chloride reaction showed a positive result. ESI-MS gave a molecular cation peak at m/z 349 [M + Na] + . The 1 H NMR spectrum (Table 1) showed two olefinic hydrogen signals at G 7.60 (1H, d, J = 16.2 Hz) and 6.40 (1H, d, J = 16.2 Hz), which indicated the presence a trans double bond. At the same time, the signals at G 7.55 (1H, s), 7.24 (1H, d, J = 7.8 Hz), 7.14 (1H, dd, J = 7.8, 8.3 Hz), and 6.98 (1H, d, J = 8.3 Hz) implied the presence of a meta-substituted benzene ring. In the 13 C NMR spectrum (Table 1), there was a carbonyl carbon signal at G 171.8. In the range of G 110-160, there were eight unsaturated carbon signals, which is in agreement with the 1 H NMR spectrum showing the occurrence of a double bond and a substituted benzene in the structure. Compared with the 13 C NMR spectra of compounds 1 and 3, it can be concluded that there was a glucoside moiety. The E-configuration of the anomeric carbon of the glucose was deduced from the coupling constant (J = 7.4 Hz) of the anomeric hydrogen signal at G 4.9. Based on the analysis and chemical reactions, it can be concluded that compound 2 was trans-coumaric acid-3-O-E-D-glucopyranoside. HMBC and HSQC further confirmed the proposed structure and assigned the 1 H and 13 C NMR data.The trans-coumaric acid-3-O-D-D-glucopyranoside was formerly synthesized by Funayama [7] through the catalysis of glucoside synthetase, but the E anomer is reported herein for the first time, and this investigation also revealed its presence in nature for the first time. In addition, as known phytochemicals, compounds 1 and 3 were indentified through comparison of the NMR data with the literature [8,9].

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Chemical constituents from a Chinese fern Polypodium hastatum Thunb.

Yao

Duan

et al. 2012

Biochemical Systematics and Ecology

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The Chemical Constituents of Polypodium Niponicum

Cited by 4 publications

References 11 publications

Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application

Naturally Occurring Nor-Steroids and Their Design and Pharmaceutical Application

Coumaric Acid Glucosides from the Chinese Fern Polypodium hastatum

Chemical constituents from a Chinese fern Polypodium hastatum Thunb.

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