黄槿（Hibiscus tiliaceus）属于锦葵科（Malvaceae）木槿属（Hibiscus），是一种具有重要药用、生态和观赏价值的半红树植物，广泛分布于中国、越南、柬埔寨、缅甸、印度等热带地区；在我国主要分布于海南、广西、广东等省，现已被广泛种植栽培。据《全国中草药汇编》记载，黄槿具有清热止咳、解毒消肿等功效，在海南沿海地区作为药物用于治疗毒蛇咬伤、痈疮肿毒、支气管炎等。

本论文采用现代色谱等多种分离技术对黄槿二氯甲烷提取物进行了系统研究，结合波谱学手段（IR、UV、MS 、NMR、ECD和X-ray）以及量子化学计算法（DFT）从中鉴定77个单体化合物，主要包括杜松烷型倍半萜类化合物73个（1-70），木脂素类化合物3个（71-73）以及苯酚类化合物1个（74），其中27个新化合物，均为杜松烷型倍半萜类或其重排类化合物，命名为：hibisceusones A-C（1-3），hibisceusanols A-B（4-5），6S-hibisceusin A（6a），6R-hibisceusin A（6b），6S-hibisceusin B（7a），6R-hibisceusin B（7b），6R-hibisceusin C（8a），6S-hibisceusin C（8b），hibisceusins D-S（9-24），isohemigossypol-1-methyl ether（25），gossyvertin（26），isohemigossypol（27），parviflorals A-B（28，32），syriacusins A-C（29-31），7-hydroxycadalene（33），7-hydroxy-1,2-dihydrocadalene（34），7-hydroxycadalenal（35），7-hydroxy-3,4-dihydrocadalin（36），(1R, 4R)-7-hydroxycalamenene（37），inuloidin（38），(1R, 4R)-cis-5-hydroxycalamenene（39），isohemigossypolone（40），2-O-methyl-isohemigossypolone（41），11-nor-2-O-methyl-isohemigossypolone（42），7-hydroxy-14-cadalenal（43），virginicin（44），hibiscones A-D（45-48），hibiscusterpenes IV-V（49-50），hibiscoquinones A-D（51-54），mansonones C-F（55-58），dehydrooxoperezinone-6-methyl ether（59），hibiscolactone A（60），2,7-dimethoxy-5-isopropyl-3-methyl-8,1-naphthalene carbolactone（61），2-hydroxy-5-isopropyl-7-methoxy-3-methyl-8,1-naphthalene carbolactone（62），5-isopropyl-3-methyl-2,4,7-trimethoxy-8,1-naphthalene carbolactone（63），11-hydroxy-2-O-methylhibiscolactone A（64），bombamalone A（65），O-methylhibiscone D（66），thespesilactam（67），4-isopropyl-6-methyl-1-naphthalenemethanol（68），1,3,5-cadinatriene-(7R),(10S)-diol（69），gossypol（70），cleomiscosins A-C（71-73）和vanillin（74）。化合物1-24为新化合物，其中化合物1-3为1组非对映异构体，具有独特的1, 4-双氧六元桥环稠合的杜松烷型倍半萜二聚体；化合物4-5为稠合呋喃三环杜松烷型倍半萜碳连双环杜松烷型倍半萜二聚体；化合物6-8为通过手性柱色谱拆分得到的3组对映异构体，为缩环重排产生的杜松烷型倍半萜碳骨架；化合物9可由6通过Bayer-Villiger反应，重排产生的杜松烷型倍半萜内酯环骨架结构；化合物12为呋喃环质子氢异丙基取代产生的杜松烷型倍半萜类碳骨架结构；化合物10和17为甲基重排产生的双环杜松烷型倍半萜碳骨架结构。

同时，本论文采用体外MTT法和MIC法对黄槿提取物和部分单体化合物进行了肿瘤细胞毒活性以及病原菌抑制活性筛选，筛选结果显示：黄槿提取物对肝癌细胞及妇科肿瘤的细胞毒活性显著优于对肺癌和胃癌细胞毒活性，化合物2，6b，7b和9对人肝癌细胞以及三阴乳腺癌细胞具有显著的细胞毒活性，特别是化合物2对三阴乳腺癌细胞毒活性优于阳性药紫杉醇；化合物9，19，25-29，55-56对棉花黄萎病菌（V. dahliae），水稻纹枯病菌（T. cucumeris），棉花枯萎病菌（F. oxysporum）以及尖孢镰刀菌（F. oxysporum HK-27）均具有明显的抑制活性，与阳性药多菌灵活性相当。

除此之外，本论文对近十年天然杜松烷型倍半萜类成分及其药理活性的研究进行了总结和综述，为天然杜松烷型倍半萜类物质的研究与开发提供科学依据。

Hibiscus tiliaceus as a semi-mangrove, belongs to the genus of Hibiscus (Malvaceae family) with important medicinal, ecological and ornamental values. It is widely distributed in tropical regions of China, Vietnam, Cambodia, Myanmar, India and so on, and extensively planted cultivation at present. It has the functions of heat-clearing and detoxifying and as a stasis-dissipating and detumescence agent according to the "National Compilation of Chinese Herbal Medicine". Also, it is used traditionally as a folk medicine for treating venomous snake bite, carbunculosis and bronchitis in Hainan coastal residents.

In this paper, the dichloromethane extraction of from H. tiliaceus was systematically studied using modern chromatography and other separation techniques, and 77 compounds were obtained and their structures were elucidated by IR, UV, MS, NMR, ECD, X-ray spectroscopy and quantum chemical calculation (DFT). The identified structures contained seventy-three cadinane -type sesquiterpenoids (1-70), three lignans (71-73) and one phenol (74). Among them, twenty-seven ones were new compounds with cadinane -type sesquiterpenoids or their rearrangement structures. All compounds were named as hibisceusones A-C (1-3), hibisceusanols A-B (4-5), 6S-hibisceusin A (6a), 6R-hibisceusin A (6b), 6S-hibisceusin B (7a), 6R-hibisceusin B (7b), 6R-hibisceusin C (8a), 6S-hibisceusin C (8b), hibisceusins D-S (9-24), isohemigossypol-1-methyl ether (25), gossyvertin (26), isohemigossypol (27), parviflorals A-B (28，32), syriacusins A-C (29-31), 7-hydroxycadalene (33), 7-hydroxy-1,2-dihydrocadalene (34), 7-hydroxycadalenal (35), 7-hydroxy-3,4-dihydrocadalin (36), (1R, 4R)-7-hydroxycalamenene (37), inuloidin (38), (1R, 4R)-cis-5-hydroxycalamenene (39), isohemigossypolone (40), 2-O-methyl-isohemigossypolone (41), 11-nor-2-O-methyl-isohemigossypolone (42), 7-hydroxy-14-cadalenal (43), virginicin (44), hibiscones A-D (45-48), hibiscusterpenes IV-V (49-50), hibiscoquinones A-D (51-54), mansonones C-F (55-58), dehydrooxoperezinone-6-methyl ether (59), hibiscolactone A (60), 2,7-dimethoxy-5-isopropyl-3-methyl-8,1-naphthalene carbolactone (61), 2-hydroxy-5-isopropyl-7-methoxy-3-methyl-8,1-naphthalene carbolactone (62), 5-isopropyl-3-methyl-2,4,7-trimethoxy-8,1-naphthalene carbolactone (63), 11-hydroxy-2-O-methylhibiscolactone A (64), bombamalone A (65), O-methylhibiscone D (66), thespesilactam (67), 4-isopropyl-6-methyl-1-naphthalenemethanol (68), 1,3,5-cadinatriene-(7R),(10S)-diol (69), gossypol (70), cleomiscosins A-C (71-73) and vanillin (74)。Compounds 1-24 were new compounds, among which compounds 1-3 were diastereoisomers with a unique dimer framework of 1, 4-dioxane bridged ring fused to different cadinane-type polycyclic skeletons. Compounds 4-5 were incorporated a fused-furan tricyclic cadinane sesquiterpene with a dicyclic cadinane sesquiterpene dimers though carbon bonds linkage. Compounds 6-8 were three groups of enantiomers separated by chiral column chromatography, which were cadinane-type sesquiterpenoid carbon skeletons generated by ring contraction rearrangements. Compound 9 may be derived by a Bayer-Villiger rearrangement of 6. Compound 12 was the cadinane-type sesquiterpenoid carbon skeleton produced by the addition of an isopropyl replaced at furan ring proton. Compounds 10 and 17 were dicyclic cadinane-type sesquiterpene carbon skeleton structures formed by methyl rearrangement.

In this paper, in vitro MTT assay and MIC assay were used to evaluate anti-tumor cytotoxicity and anti-pathogen activities of the extracts and some monomer compounds from H. tiliaceus. The results showed that H. tiliaceus extract displayed more significant cytotoxicity against liver cancer cells and female cancer cells than the cytotoxic activity of lung cancer and stomach cancer. Compounds 2, 6b, 7b and 9 showed remarkable activities of human liver cancer cells and three female breast cancer cells, especially compound 2 with noteworthy anti-TNBC activity. Compounds 9, 19, 25-29, 55-56 exhibited broad-spectrum inhibitory activities against V. dahliae, T. oryzae, F. oxysporum and F. oxysporum HK-27 comparing with the that of positive drugs carbendazim.

In addition, the research on the natural cadinane sesquiterpenoids and their pharmacological activities were reviewed systematically in the past decade, which provided a reference for the research and development of natural cadinane sesquiterpenoids in this paper.