Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

doi:10.1007/s13659-024-00475-7

应用天然产物 ›› 2024, Vol. 14 ›› Issue (6): 54-54.DOI: 10.1007/s13659-024-00475-7

Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

Phanruethai Pailee¹, Paratchata Batsomboon¹, Wiriya Yaosanit¹, Theerawat Thananthaisong², Chulabhorn Mahidol^1,3, Poonsakdi Ploypradith^1,3,4, Nanthawan Reuk-ngam¹, Panita Khlaychan¹, Supanna Techasakul¹, Somsak Ruchirawat^1,3,4, Vilailak Prachyawarakorn¹

1. Laboratory of Natural Products, Medicinal Chemistry and Organic Synthesis, Chulabhorn Research Institute, Bangkok, 10210, Thailand;
2. Department of National Parks, Wildlife and Plant Conservation, Forest Herbarium, Bangkok, 10900, Thailand;
3. Program in Chemical Sciences, Chulabhorn Graduate Institute, Bangkok, 10210, Thailand;
4. Center of Excellence on Environmental Health and Toxicology (EHT), Office of the Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), Bangkok, 10400, Thailand

收稿日期:2024-03-31 出版日期:2024-12-24 发布日期:2024-12-13
通讯作者: Vilailak Prachyawarakorn,E-mail:vilailak@cri.or.th
基金资助:
The grants from Thailand Science Research and Innovation (TSRI) and Chulabhorn Research Institute (grant numbers 48296/4691995) and Center of Excellence on Environmental Health and Toxicology (EHT), OPS, Ministry of Higher Education, Science, Research and Innovation were supported the research funding.

Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

1. Laboratory of Natural Products, Medicinal Chemistry and Organic Synthesis, Chulabhorn Research Institute, Bangkok, 10210, Thailand;
2. Department of National Parks, Wildlife and Plant Conservation, Forest Herbarium, Bangkok, 10900, Thailand;
3. Program in Chemical Sciences, Chulabhorn Graduate Institute, Bangkok, 10210, Thailand;
4. Center of Excellence on Environmental Health and Toxicology (EHT), Office of the Permanent Secretary (OPS), Ministry of Higher Education, Science, Research and Innovation (MHESI), Bangkok, 10400, Thailand

Received:2024-03-31 Online:2024-12-24 Published:2024-12-13
Contact: Vilailak Prachyawarakorn,E-mail:vilailak@cri.or.th
Supported by:
The grants from Thailand Science Research and Innovation (TSRI) and Chulabhorn Research Institute (grant numbers 48296/4691995) and Center of Excellence on Environmental Health and Toxicology (EHT), OPS, Ministry of Higher Education, Science, Research and Innovation were supported the research funding.

摘要/Abstract

摘要： Eleven novel clerodane-type diterpenoids, grewiifopenes A-K (1-4 and 12-18), along with nine known compounds (5-11, 19, and 20) were purified from the dichloromethane extract of the twigs and stems of Casearia grewiifolia Vent. (Salicaceae). Their spectroscopic data, including the NMR, HRESIMS, and electronic circular dichroism calculations were employed to completely characterize and elucidate the chemical structures and absolute configurations. The clerodane diterpenoids possessing a 6-OH group and no substitution at C-7 exhibited greater cytotoxic activity than others, with their IC₅₀ values ranging from 0.3 to 2.9 μM. Isocaseamembrin E (7) exhibited antibacterial activity against Staphylococcus aureus, while isocaseamembrin E (7), corymbulosin X (8), caseargrewiin A (9), kurzipene A (10), and balanspene F (11) exhibited antibacterial activity against Bacillus cereus.

关键词: Casearia grewiifolia Vent., Salicaceae, Clerodane diterpenoids, Cytotoxic activity, Antibacterial activity

Abstract: Eleven novel clerodane-type diterpenoids, grewiifopenes A-K (1-4 and 12-18), along with nine known compounds (5-11, 19, and 20) were purified from the dichloromethane extract of the twigs and stems of Casearia grewiifolia Vent. (Salicaceae). Their spectroscopic data, including the NMR, HRESIMS, and electronic circular dichroism calculations were employed to completely characterize and elucidate the chemical structures and absolute configurations. The clerodane diterpenoids possessing a 6-OH group and no substitution at C-7 exhibited greater cytotoxic activity than others, with their IC₅₀ values ranging from 0.3 to 2.9 μM. Isocaseamembrin E (7) exhibited antibacterial activity against Staphylococcus aureus, while isocaseamembrin E (7), corymbulosin X (8), caseargrewiin A (9), kurzipene A (10), and balanspene F (11) exhibited antibacterial activity against Bacillus cereus.

Key words: Clerodane diterpenoids, Cytotoxic activity, Antibacterial activity, Casearia grewiifolia Vent., Salicaceae

Phanruethai Pailee, Paratchata Batsomboon, Wiriya Yaosanit, Theerawat Thananthaisong, Chulabhorn Mahidol, Poonsakdi Ploypradith, Nanthawan Reuk-ngam, Panita Khlaychan, Supanna Techasakul, Somsak Ruchirawat, Vilailak Prachyawarakorn. Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.[J]. 应用天然产物, 2024, 14(6): 54-54.

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Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

Grewiifopenes A-K, bioactive clerodane diterpenoids from Casearia grewiifolia Vent.

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