24-Dehydrohippuristanol, a cytotoxic spiroketal steroid from Isis hippuris

Yi Qi Huang; Amina M. Illias; Po Jen Chen; Su Ying Chien; Yueh Hsiung Kuo; Chou Yuan Ko; Chun Feng Chang; Zhi Hong Wen; Tsong Long Hwang; Ping Jyun Sung

doi:10.1016/j.tetlet.2023.154540

24-Dehydrohippuristanol, a cytotoxic spiroketal steroid from Isis hippuris

Yi Qi Huang, Amina M. Illias, Po Jen Chen, Su Ying Chien, Yueh Hsiung Kuo, Chou Yuan Ko, Chun Feng Chang, Zhi Hong Wen, Tsong Long Hwang^*, Ping Jyun Sung

^*Corresponding author for this work

School of Traditional Chinese Medicine

Research output: Contribution to journal › Journal Article › peer-review

2 Scopus citations

Abstract

Chemical screening of a Formosan sea bamboo octocoral Isis hippuris have led to the isolation of nine spiroketal steroids, including a new metabolite, 24-dehydrohippuristanol (1), a new natural product, hippuristanol 11-one (2), as well as seven known analogs, hippuristanol (3), 22-epi-hippuristanol (4), hippurin-1 (5), 22-epi-hippurin-1 (6), 3-acetyl-22-epi-hippurin-1 (7), 3α-acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lactone (8) and (22S)-3α-acetoxy-11β,18α-dihydroxy-24-methyl-18,20β;22,25-diepoxy-5α-furostane (9). The structures of steroids 1–9 were corroborated by 2D NMR experiments and comparison with literature data. The configurations of steroids 3, 4, 6 and 9, obtained in previous studies, were reported for the first time in this study by single-crystal X-ray diffraction analysis. Steroid 1 exhibited cytotoxic effects against DLD-1 and LoVo cancer cells with IC₅₀ values of 5.54 and 6.89 μM, respectively.

Original language	English
Article number	154540
Journal	Tetrahedron Letters
Volume	123
DOIs	https://doi.org/10.1016/j.tetlet.2023.154540
State	Published - 23 06 2023

Bibliographical note

Publisher Copyright:
© 2023 Elsevier Ltd

Keywords

Cytotoxicity
Hippuristanol
Isis hippuris
Spiroketal steroid
X-ray

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2023.154540

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title = "24-Dehydrohippuristanol, a cytotoxic spiroketal steroid from Isis hippuris",

abstract = "Chemical screening of a Formosan sea bamboo octocoral Isis hippuris have led to the isolation of nine spiroketal steroids, including a new metabolite, 24-dehydrohippuristanol (1), a new natural product, hippuristanol 11-one (2), as well as seven known analogs, hippuristanol (3), 22-epi-hippuristanol (4), hippurin-1 (5), 22-epi-hippurin-1 (6), 3-acetyl-22-epi-hippurin-1 (7), 3α-acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lactone (8) and (22S)-3α-acetoxy-11β,18α-dihydroxy-24-methyl-18,20β;22,25-diepoxy-5α-furostane (9). The structures of steroids 1–9 were corroborated by 2D NMR experiments and comparison with literature data. The configurations of steroids 3, 4, 6 and 9, obtained in previous studies, were reported for the first time in this study by single-crystal X-ray diffraction analysis. Steroid 1 exhibited cytotoxic effects against DLD-1 and LoVo cancer cells with IC50 values of 5.54 and 6.89 μM, respectively.",

keywords = "Cytotoxicity, Hippuristanol, Isis hippuris, Spiroketal steroid, X-ray",

author = "Huang, \{Yi Qi\} and Illias, \{Amina M.\} and Chen, \{Po Jen\} and Chien, \{Su Ying\} and Kuo, \{Yueh Hsiung\} and Ko, \{Chou Yuan\} and Chang, \{Chun Feng\} and Wen, \{Zhi Hong\} and Hwang, \{Tsong Long\} and Sung, \{Ping Jyun\}",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Ltd",

year = "2023",

month = jun,

day = "23",

doi = "10.1016/j.tetlet.2023.154540",

language = "英语",

volume = "123",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - 24-Dehydrohippuristanol, a cytotoxic spiroketal steroid from Isis hippuris

AU - Huang, Yi Qi

AU - Illias, Amina M.

AU - Chen, Po Jen

AU - Chien, Su Ying

AU - Kuo, Yueh Hsiung

AU - Ko, Chou Yuan

AU - Chang, Chun Feng

AU - Wen, Zhi Hong

AU - Hwang, Tsong Long

AU - Sung, Ping Jyun

PY - 2023/6/23

Y1 - 2023/6/23

N2 - Chemical screening of a Formosan sea bamboo octocoral Isis hippuris have led to the isolation of nine spiroketal steroids, including a new metabolite, 24-dehydrohippuristanol (1), a new natural product, hippuristanol 11-one (2), as well as seven known analogs, hippuristanol (3), 22-epi-hippuristanol (4), hippurin-1 (5), 22-epi-hippurin-1 (6), 3-acetyl-22-epi-hippurin-1 (7), 3α-acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lactone (8) and (22S)-3α-acetoxy-11β,18α-dihydroxy-24-methyl-18,20β;22,25-diepoxy-5α-furostane (9). The structures of steroids 1–9 were corroborated by 2D NMR experiments and comparison with literature data. The configurations of steroids 3, 4, 6 and 9, obtained in previous studies, were reported for the first time in this study by single-crystal X-ray diffraction analysis. Steroid 1 exhibited cytotoxic effects against DLD-1 and LoVo cancer cells with IC50 values of 5.54 and 6.89 μM, respectively.

AB - Chemical screening of a Formosan sea bamboo octocoral Isis hippuris have led to the isolation of nine spiroketal steroids, including a new metabolite, 24-dehydrohippuristanol (1), a new natural product, hippuristanol 11-one (2), as well as seven known analogs, hippuristanol (3), 22-epi-hippuristanol (4), hippurin-1 (5), 22-epi-hippurin-1 (6), 3-acetyl-22-epi-hippurin-1 (7), 3α-acetoxy-11β-hydroxy-24-methyl-22,25-epoxy-5α-furostan-18,20β-lactone (8) and (22S)-3α-acetoxy-11β,18α-dihydroxy-24-methyl-18,20β;22,25-diepoxy-5α-furostane (9). The structures of steroids 1–9 were corroborated by 2D NMR experiments and comparison with literature data. The configurations of steroids 3, 4, 6 and 9, obtained in previous studies, were reported for the first time in this study by single-crystal X-ray diffraction analysis. Steroid 1 exhibited cytotoxic effects against DLD-1 and LoVo cancer cells with IC50 values of 5.54 and 6.89 μM, respectively.

KW - Cytotoxicity

KW - Hippuristanol

KW - Isis hippuris

KW - Spiroketal steroid

KW - X-ray

UR - https://www.scopus.com/pages/publications/85159074506

U2 - 10.1016/j.tetlet.2023.154540

DO - 10.1016/j.tetlet.2023.154540

M3 - 文章

AN - SCOPUS:85159074506

SN - 0040-4039

VL - 123

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 154540

ER -

24-Dehydrohippuristanol, a cytotoxic spiroketal steroid from Isis hippuris

Abstract

Bibliographical note

Keywords

UN SDGs

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